Helaine Knapp | CITYROW

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Helaine has always been a go-getter. Directly out of college, she joined the Conde Nast team before moving to Buddy Media (which was acquired and is now under the Salesforce umbrella). Roughly five years ago, while working full-time at Olapic, she found herself in search of a good workout and fell in love with rowing. After a long year and pulling double-duty at a day job and hardcore side hustle, she finally left to make CITYROW a full-time reality.

I met her at her Upper East Side studio where she told me her journey so far, including all the highs and lows along the way, from accidentally locking a customer inside the studio (the patron was in the shower, she found out when the security company called her to report a break-in) to not being able to actually do the workout for the first several months of the business’s opening because she was awaiting back surgery.

 cITYROW's WATER ROWERS, all photos by jay sullivan

cITYROW's WATER ROWERS, all photos by jay sullivan

How did you get started, both as an entrepreneur and more specifically within the fitness industry? 

I was actually brought up with a YOLO attitude (laughs). My mom lost her father and her brother in a tragic plane crash. She had been doing financial sales for many years and then gave it all up to become a rabbi just like that. I think it was ingrained in me to go for things.

In terms of fitness, I was a little bit of a chubby kid growing up.  Then I went to Michigan for undergrad and definitely wasn’t healthy there… at all (laughs). At the same time, though, I was always one of those people who craved balance. It’s kind of why I chose Michigan, a very ‘work hard, play hard’ kind of place. I became a working adult and, partially because I worked in the media world, found myself going out several times a week.  I realized you can’t really go out for burgers and beers every single night without something to balance it out.

In looking for that balance, I discovered boutique fitness. I got introduced to Soul Cycle, Barry’s, Pilates, and others, and I realized that all of the sudden there’s an option to do a class, then go to dinner, and be in leggings the whole time! I thought, “This sounds great.”

Also, signing up for classes held me accountable. When you make a sweat-date with a friend, you get to see them but you also get to check off a box, whatever your number is for the week, those 3 – 4 workouts will happen.

Why Rowing? 

The reason I got into rowing was that I’d been injured from doing so many classes all the time. I had a herniated disc and was told by my doctor that I needed a low impact workout. But there was nothing that existed that was low impact and still delivered the serious sweat I was craving.

At first, I completely wrote off rowing as something my dad did in college or something exclusively for Ivy league-ers… then when I saw the WaterRower in a Details Magazine article being recommended by trainers for being low impact and providing a sweat, I had to give it a shot.

So you found your workout. Were you still working at Olapic when CITYROW launched? Was it stressful working two jobs at once?  When did you make the leap full time?

The anxiety of being found out was starting to rise a few months in. I ended up keeping the secret for over a year. It was hard to focus on two things and feel like I wasn't giving 100% to my job, but the reality was, I was giving way more than 100% and still crushing it at Olapic.

What moment did you realize, OK this is happening?

I have a few press friends and the story got picked up.  Then Well & Good did a story about the rowing trend (we were going as Row NY at that time). I spoke to them and said I was opening in the fall of 2013, a total lie, I just thought that could be an option!

Were you scared?

When it came to investors, I was worried about not knowing the lingo; I felt really out of my league sometimes and had to fake it until I made it. You’ve got to turn it on and you’ve got to sell it all the time. That can be tough.

How did you find your first studio space?

Real estate in NY was hard. My dad is a residential real estate attorney but it turns out that residential is totally different than commercial real estate.

Once we found our space, we started negotiating.  The guy was older and somewhat bullying me, this 20-something who knew nothing about commercial real estate, just as the lease needed to get signed.

I was at a wedding in the Berkshires, totally stressed out, and I just looked around and asked everyone, “Does anyone here do commercial real estate?!” And this friend of a friend turned out to be a commercial estate attorney! So we went for a beer before the wedding and he helped me write back with seven questions and it all worked out. He gets free classes for life!

So let’s cut to launch, you have the class, you have the space, what’s next?

We had generated close to twelve or fifteen-hundred emails before we launched. We emailed that list, set up a booking email and by January 3rd or 4th, we’d made about $7,000.00.  That was crazy!

A lot of my team still had day jobs then, so when we first started one of us would do the early class before work, then Alex, who I worked with at Olapic, would leave the office at lunch and go work the desk for our 12:30pm class.

Also, in the beginning, our neighbors hated us. Our music went directly into their conference room through the air vents. We had to re-do the flooring and we spent a ton on soundproofing.

There aren't any showers or locker rooms and there’s no place to change. It’s janky but people keep coming back!

There’s always something! Besides real estate and soundproofing, were there any other dark nights of the soul along the way?

For our second studio, I signed a lease when I wasn’t really funded to do that and it was a disaster. I had to see a lawyer, and to fix the problem we had to put together a loan with the contractor who was building out the space.  There were some very hard conversations, lost sleep and a lot of crying, but in the end we did a lot of value engineering on the space and we’re excited for how everything turned out.

One thing that really helped me with attracting investors was bringing on someone with a finance background. He believes in our vision in a way that I don’t have to explain and that makes things a lot easier.

How do you define success for CITYROW?

We are successful! We have built, launched and are sustaining a business in New York City. I’m always striving for more and we haven’t hit our projections yet, but I know we will do 30 – 60% more revenue.

Further than that, I’d like to try to get this thing everywhere and be first in other markets. We have copycats like crazy.  They copy our website word for word. I try not to take it personally but it does hurt me.

To put it simply, I’d like to see expansion, both from a retail perspective and also digitally.

What do you see trend wise next five years/ the future?

Part of the reason I started CITYROW is that people are getting smarter about their bodies these days. Fifteen years ago people were just like, “OK, so do I have to work out?” but now everyone’s working out, and people are smarter about what they are doing and why. Now people understand words like HIIT (high intensity interval training) and low-impact and why they’re healthy for you. Those two things are a big part of what CITYROW is all about.

You have this great product, what’s been the most effective marketing initiative?

I’d say marketing is where we have room for growth. I think we naturally capture a wide audience from PR and having a great product that works. People love to tell our story and people love a new concept, so early on we did really well from word of mouth. Education and trial is our biggest challenge, which is why PR is so helpful, because it helps tell our story.

Do you have any advice for people starting their own company?

One of the founders of Buddy Media told me to jump in when the water is cold. People will never get it unless you do it. It’s fucking terrifying and there is always someone there to take your idea once it has found success, so you have to be first.

You have to believe in it; top to bottom and bottom to top. You must be O.K. with rejection and have that drive that will get you through the lows. There have been times where I wasn’t sure we could get through the day but you have to put on a smile and just keep going.

Jesse Israel | The Big Quiet & Mediclub

I met Jesse at a wellness retreat outside of Austin, TX this past spring.  He and I were on the same hotel shuttle from the airport and I remember liking him right off the bat.  He was an interesting character who was very open, and he seemed more enlightened than most people I knew.  Over the course of the trip, we had some great conversations and got paired up to practice yoga together.  By the end of it, I felt like I’d found a new great friend.

Jesse has a story I find inspiring on a soulful level.  A successful music industry vet, Jesse co-founded Cantora in his early 20s before he decided to leave almost a decade later in order to pursue his true passion of bringing meditation and community to a wider audience.

Leaving his record company took no small amount of guts.  He walked away from what many would consider to be an entrepreneur’s dream actualized – a successful record label, and the money and lifestyle that goes along with it. 

But that’s part of what makes Jesse’s story so interesting. Why did he walk away when he’d achieved so much?  As challenging as it was, Jesse talks about the wisdom of following his heart, and how ultimately trusting his intuition led him to a place where he feels more aligned with himself and his purpose.  Jesse now runs two new ventures: Mediclub and The Big Quiet, both of which revolve around meditation and help people become more connected with their self and their communities. 

Both businesses are doing well and making a big impact, but it wasn’t always easy getting to this point.  Through his experience, Jesse encountered many challenging trials and dark days, yet he’s learned from them and persevered in finding his way.  

It’s an inspiring story, and for those seeking rich entrepreneurial and cultural insight that you can only get from the story of someone who has experienced it, here is Jesse Israel’s By the Bootstraps.

 photo by  felix Kunze

photo by felix Kunze

You co-founded Cantora when you were still in school and things were going pretty well.  Why did you decide to change paths when, from an outsider’s perspective anyway, nothing was wrong business-wise?

It was in my heart. I’d had this incredible nine-year run that I was deeply connected to at another point in my life, but around year eight I started to get this feeling and my intuition was just to move on.

I tried to address it logically; what if I change my role?; what if we go to business partner therapy?; etc. I’m so glad we tried all those things because it was not a logistical thing or a simple change or tweak, it made me realize I was meant to move on to the next thing in my life.

I made a list of pros and cons. Pros: incredible business partners, we were making money, sick office space, etc. So many good things! The cons were just that my heart was not in it. That’s it.

I’d learned meditation in my twenties, and I can point to that as a tool that gave me clarity and taught me how to trust my intuition. With that, I could make the leap. I’ve got to say that as emotional and tough as it was, it was like an amicable divorce, and acting on opening myself up to what was next was so affirming to me. 

After that period, the genesis of Mediclub seems very organic.

I left the company, traveled to Africa and dedicated myself to Cyclones, a side project that I’d been working on (Cyclones is a bike club helping students in rural Africa become better students by cutting down their commute time walking by giving them access to bikes.) 

It helped me realize that it is one thing to build a community through a shared interest in riding bikes and discovery, but it is a very different thing to have a deeper purpose within that shared community.

I was so moved by the growth of that Cyclones community, but by then I was maybe six months into my process of transitioning out of the Cantora business and it was too cold to ride bikes in New York (December 2014) so I wanted to find something else I could commit myself to.

Using my gifts of bringing people together was always my passion, and, at the time meditation was the most consistent thing in my life, as well as something I was finding myself increasingly passionate about. Also, I was noticing all of these colleagues and friends that I knew from nightlife and music and tech that were starting to learn meditation and practice it but that didn’t have a place to do it together. 

We started MediClub in my buddy’s beautifully designed loft in Soho.  We told everyone to come over and for 20 minutes, whatever style of meditation you want to do, let’s just do it together and then we’ll have a conversation. Basically, “we can put on a cool Spotify playlist and have some food and a little party that’s centered around meditation and discussion.”

And that really resonated. I realized at that first event how powerful it was to share quiet with people, especially those who are typically very busy. Also, I noticed that people who come together and share meditation as a common thread tend to be deeper in how they communicate, socialize and speak about the self.

After twenty minutes in a safe space, important topics would come up: inner relationships, money, fear and intuition, and career changes. In the past, these were topics I would only talk about with my therapist yet here I was talking about this stuff with my peers - my equals - and there was something so powerful about being heard; hearing people and knowing that other people were going through the same things.

And it grew from there. The Mediclub experience continued to attract people to our community and I heard many people say, “I’ve been looking for something like this, a place where I can really go and open up.” 

After five months, it was time to share our value system with the rest of the city, and that’s when The Big Quiet was born. To build the experience we brought in DJs and food, we received support from the brands that our friends were involved with and in turn, we supported them as well. We added some ice breakers and tried to get guests out of their comfort zones a little bit.

As I hear it, it’s almost like there were no struggles. The way you presented the growth of the business to me it’s almost as if it was meant to be. Were there any challenges you faced? Or, anyone that guided you along the way? 

This whole process has been full of challenges and fear. I’ve never experienced so much fear. I wasn’t able to commit to this work for so many reasons: who I am; who I am as a “working man” in this world. I’m still processing those challenges. I’ve come to learn that the work I’m doing now sits right at my biggest trigger points and greatest fears.

Taking it back a few years, when I first left my company, I was elated for a few weeks, but then I went into a dark hole of comparison for several months where it felt pretty much impossible to enjoy anything. I was 29 and I was watching all my friends around me at the highest points in their careers. Meanwhile, I had minimal savings and a lifestyle I’d just walked away from.

I had supportive parents but no friends going through that process, so it was very lonely. On top of that, I’d speak about the work that I was (and am) doing as “little group meditations.” I allowed myself to see it from this one lens of, “this is some soft, lame shit to be doing as a grown man…” Basically, I was thinking, “Good for you dude, but how are you going to make a living at this?” There is an entrepreneur in me that wants to build something big and I never thought Mediclub would or could be that.  

During that time, I would give a share after every meditation and reveal the fears that I was going through and that gave people the permission to say their fears. I was willing to share my process and I still do. Fear, challenges, and adversity are all critical pieces to my process and what we do in our groups. 

Like I said, where Mediclub and The Big Quiet sit right now is on one of my biggest triggers; The Big Quiet has grown to thousands of people! I’m positioning myself talking about meditation in non-denominational ways… that’s something that a lot of people aren’t going to agree with or appreciate, especially compared to what I was doing before which was something they could understand.

So much of my energy has gone into making sure that everybody “likes” it, “likes” me and wants to come back. It’s been draining to try and create that for everyone especially when my biggest fear is to be un-liked.

To be honest, I was at a low point when you saw me at the last Big Quiet in Central park. (Editors’ note, It was this past Summer, I went with my team and loved the experience.) The need to please every person was so strong, I was barely able to show up and host that event. It was a turning point for me. I felt so uninspired and drained but I was able to spend time with (mentor and friend) Jonni who helped me understand why I was experiencing the shutdown and why I wasn’t able to enjoy what should’ve been a positive night.

It’s so important to me to be seen as ‘liked’ and ‘cool’ and operating on this very safe plane. And my biggest learning over the past two months has been to connect with my core and put my faith in the fact that I’m doing it because I believe it’s what I’m meant to do. I need to do what feels right to me and that’s OK whether people like it or not.

That’s powerful stuff.

I’m still going through it, ya know?

In truth, we’re always in the middle of it. I’ve just turned 40 so that may have something to do with it. Also, running a company with 17 people is a challenge, but on the other hand, you can see these things as opportunities. When you do commit to pushing your business in a new direction, it gives you an opportunity to figure out yourself and there is an actualization that happens.

The dark periods or low days are awesome opportunities to learn about the self. The more that I’ve learned to not fight those days and just accept them has made the whole thing more enjoyable.

Tell me more about mentors and Jonni.

My mentor is named Jonni Pollard; I met him through the Vedic meditation community. He’s renowned and is essentially an empowerment coach, a personal consultant for CEOs and political figures and icons, and a very meaningful guy. He’s been studying under masters for twenty years but is also this cool modern guy and he blends these worlds together in a solid way. He had been doing mass meditations in Australia, so when we were going to do it here in the U.S. I got in touch and he started advising me on how to build out Big Quiet.

And after he did that, he started counseling me as an individual. I was going to him with fears and relationship stuff and I found him to be this incredibly meaningful sounding board with refreshing wisdom. I felt fully heard and he helped me make sense of going through things without ever forcing or trying to “fix” me. He has experience with similar work in meditation, creating safe spaces and meaningful conversation. I don’t know if I could’ve done this without him, the universe really allowed for that to happen.

There’s a Jeff Bridges quote I like where he describes intimacy as "the main high in life.”  It seems like MediClub and The Big Quiet are really aimed at facilitating that connection. What’s the vision/hope for your businesses moving forward?

Mediclub gatherings are a few hundred people, the first Wednesday of every month. Then, we have our circles program, about 45 people who are trained to facilitate conversations in small group settings in their homes. As you alluded to earlier when we were discussing the Andrew Sullivan piece, people are lonelier as a whole, as a people. Research shows that we are lonelier and more disconnected than ever before; especially those under 35 who are more digitally connected.  We are hungrier for a connection of the communal type that we no longer find useful to us, like religion. A large percentage of millennials don’t consider themselves religious but I think they’re mistaking social and digital for that type of connection. I think a lot of the issues that we’re seeing in the world come from that rampant disconnect now present between humans, and now we’re seeing a lot of young people starving for more ways to connect. I love creating solutions to that problem.

Whether it's creating a cheeseburger club for men to connect and bond; a bike club to have adventures and feel alive; or safe spaces for people to share meditation and talk about what is going on in their lives; I love creating solutions in ways that have a big impact.

You never sketched out a business plan. Not to take us off the higher purpose but since this blog is a resource for other entrepreneurs, have you thought about your business model?

The vision is to do what we’re doing here all over the world. Fulfilling that need and hunger that we’re talking about; our circles model could be meeting in lots of cities and, eventually, lots of towns.

That’s the first part of the vision because right now, what we’re really focused on is creating spaces for people to come out and talk about what’s going on in their lives and discover their truth.

The circle groups are the baby steps to people finding connections and I want a global community of empowered people living their truth. It sounds like a cliché but there is a real power in this, and there are lots of people that want that. 

Right now, we are an events business. We charge for everything from a circle to a ticket for a Big Quiet event. There is a 4-person team, including me, so that’s how we make it work: the event fee. This thing we created over a year ago is supporting itself (though my lifestyle is very different than when I was running my own label) and there are tons of ways that we can create revenue but those things will become clear to us as we keep kicking ass and coming from the heart.

Our team will talk about goals but I always say at the top of all those documents, ‘this will shift’ and ‘it’s only in pencil’. We create the space for how things will naturally evolve.

As a business owner, that’s so counter-intuitive to what you typically hear.

That’s the magical thing; I spoke to one passion problem I want to find a solution for, but there are a lot of problems that need to be solved that will come from acting from faith and following your gut and your heart. And that’s different from what we’ve been raised on, at least in the West.

Any advice for people starting their own business?

Find a style of meditation that fits and then practice it for ten minutes a day. Having a tool that will allow you stay somewhat grounded, somewhat clear, somewhat less reactive to all the things you have ahead of you will be your first step.

Step two? Get into the habit of listening to, and then acting on your gut. Like a muscle; the more you use your gut, the easier it becomes to make decisions from it and it will become an invaluable compass as you enter into the unknown. It really is our true nature, our ability to connect with something deeper and guide us in the right direction.

The third thing is being O.K. with some people not liking or not responding to what you’re doing. My advice would be to question yourself first, then give yourself fully to what you’re here to do and not listen to others’ insecurities.

Why I Decided to Produce a Spirit That No One’s Ever Heard Of

Applejack. Ever heard of it? Not the cereal, not some cloying, flavored vodka cocktail and definitely not the My Little Pony doll. (to be clear, I’m not a Brony; I just have two children under the age of 6.)

The applejack I’m referring to is the original American Spirit. Still sound unfamiliar? I can relate. 

When I first discovered applejack, roughly five years ago, I hadn’t heard of it either but what I learned has since changed my life.

America’s oldest spirit, applejack, was produced and consumed by George Washington himself. A delicious, high-proof, brown spirit, it is (depending on the brand) made from 100% apples. Yet, very few people know about it.

That’s because applejack, for most of the 20th century, was a forgotten spirit.  A quaff never called for.  After being one of our country’s most popular drinks for over 200 years, applejack was pretty well snuffed out, first by the popularity of other spirits, and second, by the temperance movement.  With the exception of Laird’s (the country’s oldest operating distillery in New Jersey, who somehow kept applejack alive all those years), applejack was history.

A few years ago, my business partner Casey and I decided applejack needed a comeback.  At that point in our careers we both had great experience marketing spirits, and with applejack we felt we could do something special.  Even so, to a lot of people that concept might’ve made us seem naïve. Creating a product that has little demand  isn't normally considered particularly savvy.  Applejack is a category that, in the US, sells in the tens of thousands of cases per year (as opposed to the tens of millions in the whiskey category) so, from a scale standpoint there’s a pretty low ceiling.  It’s a product that we would have to explain most of the time when introducing it to people, and I’d also guess that well more than half of NYC’s bars and restaurants don’t carry it. 

All this is to say, if I were an investor seeing our plan for the first time, I’m not sure I would have placed a bet on us.  But Casey and I saw this as the time for a big swing…  

Applejack may not be the most popular spirit around, but it has so much going for it that is just waiting to be discovered.  It is an authentic American spirit that few people are familiar with, yet is undeniably tasty.  True, it’s a small category, but it’s also a sleepy one with few players in the market in terms of competition. And, while the world can’t seem to get enough of authentic brown spirits, our feeling is that the back bars and liquor store shelves already have more than their fair share of small batch whiskeys and ryes.

The more we thought about applejack, the more we thought of it as a big opportunity.  A chance to offer people something truly unique, authentically American, and without question delicious, that brought new value to a consumer who was curious about new experiences and cared about things made locally.  And while it was a small category, we did note that applejack was (ahem) cropping up on some very interesting menus; places where the staff cared about their guests’ spirits experience as much as their food.

The more we learned, the more the opportunity just made sense.  And with our agency's experience helping brands (especially spirits brands) connect with people, we decided to take the plunge.

It took a few years but we found great local partners within New York (Black Dirt Distillery & Van Brunt Stillhouse) to help us source the apple juice, distill, age and bottle our spirit. And through a lot of hard work, including hand-labeling and numbering every bottle in our initial run of four hundred cases, we’re up and running in one of the world’s most exciting and competitive spirits markets, NYC.

Both Casey and I grew up in and around the New York area our entire lives, so for us, applejack isn’t only a way to develop a successful business, it is also a way for us to become engaged in the local economy by making a product we’re proud of that’s true to where we came from.  

As of last fall, we’re officially on the market and things are going really well; we’re in over eighty accounts, people are more interested in applejack than we’d thought they’d be, and we’ve received a good amount of coverage and accolades from respected spirits writers. Charles Passy, of the Wall Street Journal even asked, “Is applejack poised to become the next bourbon or rye?”


It’s an exciting time to be involved in the craft spirits market.  No doubt we’ve got a long way to go to achieve the goals we’ve set for ourselves, but the opportunity to be part of something this big is thrilling and the ride is half the fun.

Let me know what you’re drinking. What undiscovered spirit should Barking Irons Distilling & Imports Co. try to revive next? 

Ten Books For Entrepreneurs

I read. A lot. And the reason I love a physical book over the internet (though I read both) is that it gives me a chance to consider and take notes on the types of big ideas that just aren’t found in click-bait. When a book has a good big idea in it, that new perspective inspires me to think about my life and business in a completely new way, finding insights and perspectives that reframe the way I think about my life and business. Ultimately, those ideas help me focus on what really matters so I can say ‘no’ to the rest of it.

For me, the path to personal and professional growth is a great read. Here are ten that have impacted me over the last few years...

  Eight books I love, with two on loan. 

Eight books I love, with two on loan. 

The One Thing

Business owners have constant demands placed on their time - cash flow, hiring, management, new business, operations, and plenty of emails. When I head home to my family each night, I often wonder where the day went and how it flew by so quickly.  The idea behind this book is that we can do less, but achieve more by constantly prioritizing the one thing that is most important and letting the rest go. If you’re spending your time reacting and not achieving the things in life you’d like to, this book can help you recognize your big picture goal and establish a path to get there.

Double Your Profits in Six Months or Less

I got this recommendation from Jamie Dimon’s reading list. His interns had requested his favorite books and he gave 25.

I’m a creative person who started a company with zero business background and this book gave me the crash course I needed of practical business advice. The author, Bob Fifer, says that having a profit is the ultimate measure of the health of your business (personally, I think good cash flow, diversified revenue, and a good company culture are right up there too) and gives great tips on how to increase revenue and decrease costs.  For entrepreneurs looking for Cliff’s Notes on how to build a healthy business, this book is a great resource.  

The E Myth: Why Most Businesses Don't Work and What To Do About It

E-Myth is another great crash-course in business education. The big idea here is that business owners need to work ON their business, not IN their business.  Michael Gerber gives step-by-step instructions on how to build a healthy business that can be scaled and sold.  He says the big myth is that entrepreneurs need to play an outsize role in the operations of their business, when, in fact, we need to step back and build something that runs without us.  It’s an especially insightful book for those just starting out.

Eleven Rings: The Soul of Success

Phil Jackson, the basketball coach that led the Lakers and the Bulls to a combined eleven NBA championships, writes about his innovative and sometimes controversial approach to leadership.  If you like basketball, you’ll love hearing about the dramatic journeys his teams embarked upon to win.  And if you run a company, you’ll find inspired approaches to management.  Jackson covers ways to help talent realize their potential, how to build trust and camaraderie, and how to unite the team while still allowing individual team members to flourish.

Quiet – The Power of Introverts in a World That Can't Stop Talking

The introvert/extrovert divide is one of the few things the clinical psychology world agrees is a “real” thing. Through research and her own experiences, Susan Cain shares the challenges and opportunities of being an introvert in a culture that generally celebrates extroversion.  She asserts that the world needs introverts now more than ever for their perception, intelligence, and determination, and then provides ideas on how introverts can thrive in a business culture of extroversion.

Wherever You Go, There You Are

I started meditating a few years ago as a way to manage stress and learn more about myself. It’s been a rewarding experience that has been beneficial both to my health and that of my company.  This book helps explain why a meditation practice is helpful and also gives practical insights on how to integrate meditation into your daily life.

The Power of Habit

Charles Duhigg wrote an excellent book on how habits are the things that define us.  If we are what we do then how can we create the habits that will help us become who we want to be?  Duhigg asserts that, whether on a personal or organizational level, beginning with one habit can lead to big transformations.

The Untethered Soul: The Journey Beyond Yourself

This is a big idea book from Michael Singer that gives new perspectives on how we view life and our definition of success.  I loved it because it helped me redefine my personal vision and the vision for our agency.

Pathways to Bliss: Mythology and Personal Transformation

Joseph Campbell is often cited as one of the most influential thinkers of the 20th century.  He was gifted in his ability to examine cultures, psychology, and spirituality and convey their meaning in a way that’s relevant to how we live our everyday lives.  If that sounds like too much for you, consider this:  If life is about discovering who you are as a person, Campbell provides the signposts along the way.  If you’re an entrepreneur, this is the big picture question and nothing could be more relevant.

Mandela’s Way: Lessons on Life, Love, and Courage

Nelson Mandela was (and is) a leader worth looking up to.  Ricard Stengel chronicles the ten core principles Mandela maintained through his life that guided who he was as a person and leader.  Business can be tricky and your integrity will inevitably be tested.  Having principles to stick to in your darker hours will help you make it without compromising your values.  


Considering the big ideas they contain, books are some of the cheapest investments available for both yourself and your business.

Got any recommendations you think I'd love?  Send them my way!

The Entrepreneurial Life – The Hero’s Journey

Joseph Campbell is a favorite of mine.  At any point in your life, if you’re feeling confused about your direction, you can turn to Campbell and find new insights and inspiration about discovering your path (I highly recommend Pathways to Bliss to any aspiring entrepreneur).

One of my favorite theories of Campbell’s - and perhaps what he is best known for - is his concept of what he calls "The Hero’s Journey".  The Hero’s Journey is the culmination of years of Campbell’s research of different cultures, civilizations and religions, and it presents the idea that all myths and stories essentially share the same narrative.  It’s an insightful and powerful theory that plays a huge role in today’s pop culture and entertainment, and one that I think also influences the way we view entrepreneurs in America.

In this By the Bootstraps feature, based on my interviews to date as well as some outside research, I propose that the entrepreneur’s story (and life) inevitably takes on the character of the Hero’s Journey. And, in my follow up, I’ll write about how this story becomes a big part of what wins over the hearts and minds of the entrepreneur’s customer. Note: I’ve included a picture of Campbell’s model below, but for those interested in a more in-depth background on the Hero’s Journey, you can find different interpretations in many places. 

Today, I’ll approach the idea of entrepreneur as "Hero".  

Stages 1 – 4 (Ordinary World, Call to Adventure, Resistance and Meeting the Mentor)

In the early stages of Campbell’s twelve-step model, our entrepreneur’s journey is set in motion with a calling. 

Often an entrepreneur is living a pretty regular life when they’re struck with the realization that their passion is something they truly want to pursue.  Perhaps they’ve always been fascinated with making their own beer, and they decide to launch a craft brewery. Perhaps they’ve always loved the artistry of great clothing, so they start their own label. Or, perhaps their passion is wine, so they quit their job to become a sommelier and launch their own wine label

Whatever their dream may be, in my short experience, entrepreneurs are often "called" by a passion that they may initially resist (e.g. keep the day job until the night job pays, like my friends at The Infatuation), but eventually submit to. (There are certainly other entrepreneurs who launch a company based on an opportunity they see in the market, but I would suggest these folks are just as passionate and that their "calling" is the opportunity they see in the market, which then becomes their passion). 

Early resistance can be for many reasons but they are all related to our greatest fear – the fear of the unknown.  For me, I had trouble sleeping in the nights leading up to the moment when I quit my job as a successful television producer to "take the plunge" and start our agency.  Knowing how little I knew about running a company was daunting - and I was leaving a secure and successful career to do something completely untested - but ultimately I knew that following my heart was the only choice. That is true for anyone who starts a business. 

That hesitance can also persist and require a mentor to help coax the entrepreneur through their fear and onto their path.  The mentor might be anyone from a successful friend in the industry to a supportive investor or family friend who ultimately helps the aspiring entrepreneur believe in their personal potential (investors often say they invest in people more than ideas)  to commit fully to their vision. 

These first four steps on Campbell’s journey are critical because together they represent a commitment that takes the entrepreneur past the point of no return.  At this point, they will either succeed or fail.  In our culture we often see this initial decision to start a business as a noble one... the American Dream! And, because they’ve gone "all-in", we root for their success.

Stages 5 – 9 (Crossing the Threshold; Tests, Allies and Enemies; Approach to the Inmost Cave; The Supreme Ordeal; Seizing the Sword, Reward)

At this point our hero-entrepreneur enters the fifth stage: crossing the threshold.  Now, their business is "real" and they’re putting a product out into the world that they hope connects with consumers.  They have yanked their safety net and are now wondering if it will succeed. 

But this is just the beginning. So many businesses fail within the first five years that very few entrepreneurs ever get the happy ending made popular by some of our favorite iconic characters like Luke Skywalker, Rocky, Frodo, and many more here

The road to success is littered with ‘’A for efforts" and once an entrepreneur enters this new and foreign world (stage six), they’re quickly met with a gauntlet of trials: financing, hiring, taxes, sales(!), cash flow, management, legal, and regulatory issues, to name a few.

Luckily, they’ll also discover allies (e.g. advisors, buyers and partners) but unluckily, they’ll bump into enemies too (e.g. competition).  If they survive the challenges of stage six, our entrepreneur will continue on to what is known as the supreme ordeal, stages seven and eight. 

This sounds dramatic because it often is.  Many businesses don’t ultimately succeed without a significant trial, one that ultimately sets the business on course for long-term success.  This may be a transformative sale or acquisition, a key round of funding, or the development of a breakthrough product; what’s important is that passing this test liberates the entrepreneur, freeing them up for sustainability in the long-term.  To get there, the entrepreneur must steer their ship through dangerous straits.  This is an important time for the both entrepreneur and the business because it represents a big opportunity for growth.  And though it may be daunting, to paraphrase another writer, you’re never more alive than when you’re close to death.

At this point the entrepreneur undergoes a personal transformation, shedding their old skin and becoming a newer version of their self.  They’ve passed the supreme ordeal and in the process been transformed into a new person.  They understand, and perhaps even have mastery, of the world and industry they work in.  Few businesses achieve this level of success or go this far in the journey, but for some of those that do, their business has become "larger than the founder", and may be capable of survival without the founder at the helm.

Stages 10 – 12 (The Road Back, Resurrection, Return with the Elixir)

In steps ten, eleven and twelve, our hero/entrepreneur takes the long journey home, facing more trials along the way, but ultimately succeeding and bringing back a reward or boon along with them.  I think a great example of this might be the Chobani story, where founder Hamdi Ulukaya  (who started out ten years ago with an $800,000.00 loan from the SBA) recently decided to give his 2,000 full-time employees a 10% stock in the company now that Chobani is valued at several billion dollars.  (Mr Ulukaya, who said his goal was to pass on some of the wealth his employees helped create, had, himself, just faced an incredible "supreme ordeal" when Chobani, after attempting to open the world’s largest yogurt plant, endured product recalls and production challenges that forced them to obtain funding from an outside investor).

Not all businesses make it to this point, and different entrepreneurs have different views of success (the success of companies can’t be measured on size, revenue or profits alone), but I’ve heard more than a few entrepreneurs talk about the moment that they "made it", and arriving in this promised land is certainly the aspiration of many a bootstrapper.

As Mr. Campbell demonstrated in his books and lectures, the hero’s journey is a story deeply ingrained in our collective and individual unconscious from the time we’re young, and the stories we experience during our lifetime reinforce our belief in the truth and beauty of this myth. 

Perhaps these stories become the kindling of inspiration that, consciously or unconsciously, gives entrepreneurs the courage to "start their own thing" (after all, it’s an exciting narrative to be part of) and if so, we should be grateful, as small businesses support almost half (49.2%) of our nation’s private sector workforce (amongst many other amazing stats).

No one’s life or business follows an exact script (and uniqueness is what defines their beauty), but what’s interesting about applying The Hero’s Journey to the life of a entrepreneur is that it gives us a lens to uncover new layers of meaning and depth. 

Maybe the next time you hear a story about a founder launching a business in their garage, you’ll have a new perspective on the myth that’s about to unfold…

Stay tuned for the next edition of By The Bootstraps, where I’ll write about how the myth of the Hero’s Journey plays a big role in giving small businesses an advantage by giving customers a story to latch on to and evangelize. For examples, look no further than the craft beer, tech or beauty markets... 

Starr Hout & Laura Cramer | Apiece Apart

Apiece Apart is a women’s clothing line started by two friends, Starr Hout & Laura Cramer, who were inspired by the idea of a simplified wardrobe - essentially a “go bag” – for everyday life.  Over the past few years the brand has really taken off, and I met them for a conversation at their downtown office above the Apiece Apart pop-up store on Broome St.

When I arrived at their space, I walked into a studio full of inspiration boards, swatches of new fabrics, drawings of their latest collection and plenty of fresh flowers.  Although the space was humming with activity, when we sat down Starr and Laura exuded a calm centeredness, and I suspect this plays a big role in their success.  As partners, they have an easy way with each other and a nice harmony in the way they tell their story.

And their story is nothing short of a hero’s journey.  From explosive beginnings on the side of a road in Texas, through launching the business in a recession, to finding the perfect financing partner, theirs has all the makings of a true Bootstraps adventure.  We discussed everything, and through the course our talk they revealed all sorts of insights about starting from scratch, the importance of having supportive family and friends, grassroots marketing v. traditional PR, and scaling up once you’ve established your brand.  It’s a tale that will leave you inspired by their efforts and creativity.

And one discovery I personally enjoyed was that my mission for By The Bootstraps is similar to the reason they decided to start documenting the women wearing their clothing in their content series: Those that have been fortunate enough to cultivate a modern life while pursuing their creative passions should impart the wisdom from their journeys on the next generation.

Scroll down, aspiring bootstrapper, and discover how these intrepid women made their mark on the fashion industry on their own terms!

Photo courtesy of Apiece Apart

Starting at the beginning… How did you guys meet? Did you have a similar vision?

SH: We met in this computer programing course at ITP, which is basically MIT meets NYU. We met in a computer programming class for graduate students but we had talked ourselves in as undergraduates…

That enough is a bond!

LC: Yes. It also says something about our inter-disciplinary interests. At the beginning of the class they asked everyone why they were there. We were the only women and Starr went first and said, “I’m interested in melding art and technology together” and I was like, “Damn, she just stole my bit.” (Laughs)

Best friends.

SH: Well yes, but we also had different lives. We were studying and had our own worlds up until the week after September 11th when we ran into one another on the street and realized how much our circles of friends overlapped. Then we really clicked… at this moment where things were going well but also everything is falling apart.

Disaster does that to you.

LC: It was scary taking the subway and not knowing what was happening but we were in this circle of people that were just like “live baby live” and it all came together.

That was fifteen years ago.  Then we started a clothing line, just for our pleasure. I was in Austin sewing these dresses very poorly at my kitchen table but people were saying, “There’s something here,” and that same thing was happening to Starr with her project.

That was 2003 but we didn’t really start until 2008. We were both celebrating our 30th birthdays and we decided to go out to West Texas, to Marfa. The next day we got into my car. I had this old Mercedes and the engine was just smoking and smoking and what was meant to be an 8-hour journey turned into 16 hours. In that amazing landscape, the two of us, our boyfriends at the time and my dog Lola were all together...

SH: And we were ripe for inspiration and letting things in.

LC: We had this spark of an idea – a bag that you could pack and go anywhere that had all of your key pieces in it.

And then being in Marfa, seeing these Judd pieces and being so off the grid, that really inspired us. I think that ‘off the grid’ idea and doing things on your own terms really appealed to us. It’s also kind of how we put the company together, without too many outsiders.

We weren’t too sure how to break into fashion but things just started rolling from there. There was interest in the pieces, we had our collection and then we got our first Vogue write-up.

How did you guys decide to go from your day jobs to this? At one point did you feel like you could fully commit to it?

LC: We would’ve committed heartily at that point but still had to work. I was in Austin and would come up for six week stretches to stay where they (Starr and her husband Tim) live, in a closet basically.

There are a lot of closets in these Bootstrap stories!

LC: (Laughs) It was a long slog. We had all this success but had someone told me how hard it would’ve been early on, I’m not sure I would’ve stayed with it.

SH: We were financing the whole thing and it was really scary. We borrowed money from parents, grandparents, aunts, uncles, cousins and friends.

LC: Our first round was the “friends and family” funding round.

Did you guys think of getting investors or was it all credit cards and family?  

LC: Both of us were always thinking we needed a backer. But we didn’t really have any business doing what we were doing and didn’t have that infrastructure in place yet. That was 2008 and the whole economy had also just crashed.

All the people that might have been interested before that crash had dropped out completely because they had just lost all of their money. Stores were closing and it was just not a good time. In retrospect it was also a great time because what we were really doing was product development but we didn’t know it. We were working really hard and had supporters telling us to keep going but sales were not there.

Also, the more success we had, the harder it was on our personal bank accounts, because you have to invest to make money back. That was a period when every weekend was work and every night was work, up until 2am talking about patterns.

SH: With the growth that was happening, we couldn’t grow without investment. And there was no money available then.

LC: Ethan and I had eloped and I was pregnant and I was looking at our numbers and I was like, we can’t keep going. We could borrow $30,000 here or there but we can’t do this until we have a true financial partner.

It was a philosophical conversation – do you redouble your efforts or pivot and try another path?

So we made the decision to stop what we were doing. And we shifted our focus from the collection and making new pieces to the business plan. We would meet with anyone we could to get answers but no one had all of them.

What we thought would be a six-month business plan turned into a two-year journey.

Then, in December of 2011, we found an investor, an angel, and that was the moment it was back on. We drove down to Philly to meet with him and we were tired, really tired, and I think we decided that if this didn’t work, it would be over.

SH: I don’t even think we ever discussed that. It was just an unspoken thing that we both understood.

LC: Up until that point we had meetings with all of these top people telling us that online sales were never going to happen and our darkest days were ahead (Editor’s note: how you like them now?! J )

SH: We’d had this business plan as well as this pitch that we’d practice for hours. It was so dark. Why can’t we just take normal jobs and be happy like everyone else? But we just couldn’t let this go.

LC: By the time we met our financial partner - who is an amazing partner and a dream come true in every way - we’d been through so much, that aside from having our children and meeting the loves of our lives, our best moment in both of our lives has really been meeting this person who helped us turn our business into what it has become.


SH: Had anyone told us, like Laura said, had we known how hard it would have been, we may not have done this. You will push yourself further than you ever think you will.

LC:  Yes. So back to our angel – we went to that Philly meeting and it went well but we’d also been through enough of those meetings where people had been kind to us but weren’t really interested so we weren’t sure what to expect.

We were on the drive back at nine or ten at night from Philly and got the text, “I’m in”. Not some of the way in, all of the way in.  We didn’t even have to split up investors across 20 or 30 people like we were anticipating. I was actually pumping breast milk in the backseat when the news came in (laughs).  

That’s amazing. After all this hard work, you guys must have been so excited.

LC: We were still living in Austin and Eva (my daughter) was just about to turn one. We were passing through New Jersey when that news came in and there was this, “yes, amazing” moment but also an “everything is about to change” feeling.

SH: One thing we haven’t noted yet is that our better halves, our husbands, have been these amazing supporters. Ethan was our cheerleader and Tim would make us these amazing meals and be this wonderful supportive person.

LC: When we called them to tell them, I think both of them started crying too.

SH: Also, Ethan had to uproot his business from Austin and move to New York to support our dream now.

LC: We had discussed it and thought maybe there is a way we can do both but he made the decision that we were moving and about six months later, we were here.

So now you have financing and a collection to build, what next?

LC: We had forgotten how to design (laughs).

No, not really, but we had learned so much over that break that we joked that this was really Apiece Apart 2.0, evolving from all of our missteps along the way. 

Things were going great, we hit our numbers and we had a great season. That was proof to everyone, including our investor that everything was on the right track. That said, we still didn’t have an office and we still were doing everything ourselves.

It was funny, two full years later that we debuted our product again and people didn’t even realize we’d went away.

SH: I had felt like a big failure but people didn’t even know that we’d left which made us feel better. You go straight into the failure, then you feel it and then you’re on the other side. You learn to live with that fear and learn from it.

How did it grow from there?

LC: We had a great season then a bad season right after, ups and downs. All the money was going towards product so there was no office, no team, no infrastructure, just Starr and I working our asses off.

And it was a year from that disastrous season that we came back with another great one, with more of our learning incorporated. And with that great season, we had the benefit of adding our first full time hire, who is still with us.

With both of us being parents at that point (2014), we had to grow the company sustainably for our families, for our selves and for our health. It couldn’t just be the two of us alone anymore.

I was just talking to a woman this morning that was like, how do you do it? And I said the team has so much to do with it.

SH: Both of our moms own their own businesses so I think it’s in our blood; creating a sustainable and warm, yet passionate, hardworking environment that will take care of you because you’re being your best self in it. That is something we know we wanted to do. We are a bit more progressive in the way we do things, we don’t want a stressed out work environment just to have one.

LC: Our moms are such hard working people but they also took care of us. You can do good work and not have to be there 12 hours a day forever; you can get help that believes in the company just as much as you do.

There is a romance to putting your business together and working late nights, but as you have your family and the business develops, at some point you have to delegate.  What are the bigger dreams for Apiece Apart? What is your vision?

LC: Both Starr and I want to be at the helm of this business while growing it. The idea has always been there and we’ve always felt so strongly about it. We want it to be a large American clothing brand and we want to expand into menswear and housewares. Our wholesale business is very significant for us at the moment, but we’d like to shift to more direct sales and also grow the e-commerce.

So the pop-up is also a big opportunity, how’s that been?

LC: The pop-up is great because it’s the straight to customer stuff.

SH: Our brand is atmospheric and we can use Instagram and the website to tell that story but now we have an actual space to tell it.

I like that you bring the brand to life on Instagram through more than just product shots. Are there other ways that you guys have found to connect to your consumers without a big media spend?

The biggest story of the past year for us has been launching all of those pieces of content with Apiece Apart stories and building that following. With normal PR, we’d get in the pages of Vogue or the NY Times and nothing would happen.

In the very early days, we used to think that if we were getting coverage in the Times we had to have people waiting by the phone to take orders.  But more recently, we’re seeing the real way that people engage.

They’re not looking in a magazine and seeing it and going to buy it. They’re not engaging with the clothes right away when they see them on Instagram necessarily but it’s more like inspiration. If we put a woman in a dress, we get very few hits. But if we show a beautiful corner of someone’s home, that’s when we see people connecting.  

With PR and marketing, once we started to say, we’re going to take it grassroots style, who we are and what we actually really like, that’s when we saw it grow. What do we believe in? Once you start talking from the heart and you’re authentic, that’s when people engage with you.

That’s great, thanks so much. Final questions, for the upcoming election, any things you guys would hope for related to the business?

SH: One thing that’s been on my mind lately is thinking how we can all be more sustainable - ways we can all come together to be more green.

We can have an impact just by saying, we care about plastic bags - every business has a voice in those small ways. But then bigger picture, we had a great meeting with Eileen Fisher recently where she wanted to share their secrets of sustainable fabrics and dyes and relationships with their workers. Most companies wouldn’t share their secrets of success but she’s so progressive and really just opening up to everyone everything they’ve learned for the greater good.

LC: Another thing we’ve talked about is access. So often we’ll think, we’re pricing this beyond what people we know could personally afford. There is a cost of things that people have been ignorant of to date. In the past 10 to 15 years especially, clothing prices have been driven so far down and that drives wages down around the world and also has an environmental impact. In an ideal world we’d love to manufacture everything in New York and use only organics but the real cost of doing that makes things unaffordable to most. 

There is a reckoning now in the world and people are talking about the cost to the environment of this unsustainable model but I think only people in the position to be able to afford the higher priced items have the luxury of making some of those better choices unfortunately. Until the masses are made a little more equal in income, their impact can be felt in that way as well.

I really love Bernie Sanders – I really love Hillary as well – but I identify with his thoughts on that inequality when it comes to thinking about politics and the business.

What would I like to see happen? Obviously it is more complicated than this but… Firstly, that people start to make more money, relative to the world that we live in. Then, that there is a tax on the types of things that are really hurting the environment more. And then, that there is a credit to companies that are starting to think along green terms to incentive them. We’d need to have a long-term vision to really go full in that direction. Even someone larger like Eileen Fisher, their sustainable line is still just a passion project. It would take everyone involved to make a big change.

Last question, any advice for anyone starting out?

LC: Don’t listen to advice.

SH: Yes, I would agree with that. Also, protect your credit score if you can.  That’s something I didn’t pay attention to much when I was younger but when you are business owners, your fiscal profile is monitored so it should look good.

What I Learned At Lululemon's "The Immersion"

This past week I was one of the fortunate 50 or so “influencers” invited to the first ever The Immersion, a five-day experience hosted and paid for by Lululemon that included plenty of yoga, meditation and leadership development.

It was an incredible experience on so many levels (who knew I could do handstands?!), and I’m sure it will have a profound effect on me for a long time to come.

This being By The Bootstraps, I thought I’d take a minute to reflect on some of the things I learned about entrepreneurship while I was there.  The attendees of The Immersion were all creative people testing what’s possible in their field, and perhaps because of that, many of the people I met were entrepreneurs, including those who had their own dance companies, fitness studios, nutritional start-ups, fitness media outlets, meditation events, creative agencies, farms, wellness practices and non-profits, as well as plenty of authors with their own successful books, websites or both...

From the minute our “five-day moment” kicked off, you could sense it was an enlightened community.  People cared a great deal about health, about spirituality, about the earth and our environment, and maybe most of all, about other people.  We practiced yoga together (led by yoga master, author and founder of the Baptiste Institute, Baron Baptiste, and motivational speaker, life coach and author, Gabrielle Bernstein), meditated together, ate together, danced together and definitely had some “big talks” together.  I left feeling inspired and connected and thought I’d share some of the traits I noticed were common to the many good folks I met.

Curiosity – Entering an environment where you know no one (and Lululemon gave us no agenda or attendee list in advance) can be daunting, especially if you’re not Type A.  But from the very start I noticed that everyone was open and genuine.  In fact, not having an agenda or attendee list allowed us to see each other as people first (as opposed to our titles or accomplishments) and within the first twenty minutes I’d already made three new friends.  I think this curiosity and openness allows entrepreneurs to find new insights, which are always the spark of inspiration and innovation.

Passion – Joseph Campbell said that life is about finding our bliss, and the people I met at the Immersion knew this to be true.  Whether they were passionate about music or conservation, justice or wellness, nutrition or art, they championed their beliefs and ideas with a fire in their belly (aided, I’m sure, by the “breath of fire” that we practiced).  Everyone had something; a cause they believed in, a product they knew could help people, or a practice they’d devoted their life to; and they all shared a strong desire to connect with people through the work they were doing.  Over lunch one day, one person I met said, “Life is one big transformation.” If that’s true, then I think passion helps give us resolve when the transformation presents challenges. 

Being Grounded – The CEO of one successful company told me he tells his employees at the office, “If you can’t remember the last time you did dishes, it’s time to do the dishes.” I know for a fact this person cares a great deal about spending his time wisely but he also recognizes the power in being humble, in being part of a team and in making sure everyone feels they have a right to be there.  At The Immersion, this grounded attitude was the rule, not the exception.  When you leave your ego at the door, you become accessible and like-able in so many ways, and from a leadership perspective, nothing could be more important.

Optimism – Sure, practicing yoga all day and eating organic food can leave anyone “feeling Zen.” However, this was more than that.  Over the entire event I don’t think I heard a negative word uttered.  And although there were sessions every day from morning to night that could often be physically and emotionally demanding, everyone showed up with a positive attitude, both willing to work and willing to share.  Starting and growing a business will test your limits.  Believing you can achieve success will help you get through your challenges and discover what’s possible.

A Sense of Humor – As much yoga as we practiced and as many “big talks” as we had, every night ended with cranked-up beats, a dance party and a lot of laughs.  This says a lot about the path of the entrepreneur: Sure, success requires determination and grit, but not at the expense of your joy.  I’ve found the best things in life tend to happen when I’m not forcing them. Our yoga teacher, Baron Baptiste, gave us a word that stuck with me: Santosha.  It means content, but curious.  For me, this idea implies that the root of discovering what’s possible is your contentment, acceptance, and even happiness with the way things are.

Overall, The Immersion was an incredible experience that I know will have a lasting impact on me.  It was also a reminder that to be successful as an entrepreneur, I need to remember to give myself the time and space to recharge, get inspired and discover new perspectives.  At the opening reception Gabby told us all that over the course of the event we should take some time to “lean back.”  With all the tasks a growing business (and a family!) requires, I’m often so focused on making things happen that I forget to “lean back” and give myself the space needed for growth.  But every time I do, I discover fresh ideas and renewed energy, which is just the thing a growing business needs.

What Small Business Owners Want From Their Next President

As most of you know, the NY primaries are happening today, April 19th (and if not, consider this your reminder to get out and vote). 

As small business plays such a big role in our economy (the SBA estimates small businesses generate approximately 64% of all new jobs) I’ve been asking my bootstrapping subjects what their hopes are when the new POTUS takes office and what role owning a business plays in their voting decisions.

The answers varied, from Kerry Diamond of Cherry Bombe Magazine seeking a flat tax for businesses, to Chris Stang of The Infatuation making a spirited case for nationalized healthcare.  And while Forbes Fisher of Steve’s ice cream is pro-Hillary and Shana Tabor of In God We Trust is feeling the Bern, nearly everyone I spoke to felt that small businesses are an important part of the American economy and deserve the attention of our elected leaders.

Read the full answers from the people behind Cherry Bombe, The Infatuation, In God We Trust and Steve’s Ice Cream in the excerpts below.

Despite the media frenzy, no matter the results the Tuesday or this November, Forbes Fisher isn’t worried, “even with Trump, honestly.”

He thinks the notion of luxury items – like his company’s ice cream – dipping in sales because of leaner times is outdated and that, these days, “people are prioritizing their food purchases and making responsible selections, both environmentally and socially” no matter the cost.

We can all agree on that.

From Shana Tabor, In God We Trust:

As a business owner, the upcoming election, anything that you’re hoping to see happen?
I think most of the stuff I want to see is more personally driven. I’m not sure I’ve thought of it that much from a business-owner point of view. I probably should (laughs). I will come out and say that I’m a Bernie Sanders supporter. I think everything that he has to say is great and it would be awesome if it all actually happened.
There is a lot of shit you have to deal with as a business owner. It’s so stupid and crazy with the government. The healthcare stuff we’ve been dealing with is such a nightmare. I do find myself sort of torn because I want this to be awesome and great and I want to be supportive of it but it is actually a nightmare. They should make it all easier to deal with. 

Read her full interview here

From Chris Stang & Andrew Steinthal, The Infatuation: 

Finally, the upcoming election, you guys are business owners, is there anything from a legislation standpoint that you guys would like to see happen?
Stang: Nationalized healthcare. Not kidding. I'll get into this because it makes me angry. This is not just a political issue. Certain politicians will preach about how small business is what drives the economy and how we have to empower small businesses but a huge portion of our monthly expense is mandated healthcare for employees…to the point where if that wasn't there, we could hire two more people, today. I'm feeling the burden.
Steinthal: It's more complicated than just nationalized or not but I do think that at some point, someone has to figure out how to actually start to solve the problem. It may not be right or left but someone has got to seriously say, “How do we make it cheaper to take care of people?” There are companies out there that are hiring people on contract as opposed to full time just because they don't want to pay their benefits, which is also unfair. It's only happening more and more and yet no one has any good answers for it yet.

Read their full interview here

From Kerry Diamond, Cherry Bombe Magazine:

Anything you’d like to see happen in the upcoming election that would benefit small business owners?
I’d love for one of the candidates I’m rooting for to propose a flat tax for businesses. The tax system is so complicated I can’t wrap my head around it. As a small businessperson, you have no choice but to hire bookkeepers and accountants and muddle your way through it if you don’t have a finance or business background, which I don’t. It’s almost impossible to do it on your own.
I don’t mind paying taxes. But I want to see something good happen with that tax money—good schools, the unfortunate being taken care of… I want a candidate focused on the right things, not just making the rich richer.
The system today favors corporations, not small businesses. We’re the backbone of all these communities. It would be awesome to have all of our elected officials be super pro-small business and talk them up all the time. Can you imagine?

Read her full interview here

From Forbes Fisher, Steve's Ice Cream:

Any hopes for the upcoming election?  
Business wise. I don’t think so. Personally I am a Hillary supporter. Bernie has a great message and I think it would be nice if some of that could be incorporated into the next President’s platform but on the democratic side, I think it would be good for a woman to be president. Trump would be a disaster (laughs).
For me, I see people fighting on Facebook - if Bernie gets elected, we’ll have to pay too much in taxes, Trump will do this, etc. - but whoever is elected, I don’t see there being a huge impact on business. Even with Trump honestly.
There’s that argument that luxury items are the first to go when times are tough but I think that is a really outdated way of thinking. I think people are prioritizing their food purchases, even in ice cream, and making responsible selections, both environmentally and socially. Even if we were going to go into slow economic growth, I don’t think that would affect our market share.

Read his full interview here

Forbes Fisher | Steve's Ice Cream

How do two philosophy majors that wanted to become architects end up in the ice cream business? I found the answer recently when I met with Forbes Fisher, Co-Founder of Steve’s Ice Cream. 

In 2010, Forbes co-founded the company with David Stein, who had worked with the original Steve’s shops back in the day and was interested in re-launching the brand for today’s new, millennial consumers. Today, Forbes is both Co-Founder and President for Steve’s but his journey has involved covering nearly every position in the company from marketing to packaging.

I met Forbes in his shop at the old Pfizer factory building out in Bushwick.  The building is massive and it’s become sort of a mothership for Brooklyn food startups.  Considering Steve’s credibility and longevity, they feel a bit like a wise older brother to some of the younger upstarts.  Between sales calls and and a flavor development session, Steve squeezed in an hour to break down his personal journey and shed light on how to make it in ice cream.

Tell me about how you got started?

Dave and I met in 2010 and got along.

I liked his view of taking this older brand, the essence of that brand which is mixing things together, and thinking, what are some of the revolutionary mix-in’s today that are changing the way people think about ice cream? Or, what are some of those trends like dairy-free that we can hit on that will appeal to people today?

Early successes for us were Strawberry Ricotta and Mexican Chili Chocolate. And some more traditional ones like Salty Caramel or Southern Banana Pudding that we just put our own touches on. Our Southern Banana Pudding for example we start with banana ice cream then swirl in banana pudding.

Anyway, we saw this opportunity where people were moving away from Haagen Daaz or Ben & Jerry’s and wanted to see what we could do next in ice cream.

I lived in Brooklyn at the time but we actually launched on Long Island using one machine and just grew from there. It’s been an interesting six years, but it feels like twelve. (Laughs)

Was there a spark moment? One night where the idea came together?

I worked at Pure Food & Wine / Lucky Duck in the city and was in a CFO/COO role there and through mutual friends and colleagues met Dave. I was working on this juice bar concept and we did a deal where I licensed some dairy-free ice cream we were making for the juice bar to him to potentially manufacture. In doing that deal, we hit it off. We both were not lawyers but played that deal-making role, both were philosophy majors, both wanted to be architects in another life, it clicked.

I stayed at that job for another six months, finished the project I was working on and then approached Dave and wanted to see what his next step was when he brought up the Steve’s re-launch idea to me. We were at the original Milk Bar location behind Ssam bar and I was on board right away. We had launched it within a year.

Did you have funding and investors?

Dave had worked at the original Steve’s and that company went out of business to Ben & Jerry’s in the 90’s but before it happened, they’d taken Steve’s public so they took that infrastructure and pivoted it to a different company. That company ended up becoming the third largest ice cream company in the United States, just licensing the product out to various other companies, and Dave was the CEO, so he’d made some money to provide the initial seed investment.

The seed money was fun to play around with at the beginning but in some ways it also made it harder. I think some of it was wasted, frankly. When you have to fully bootstrap without any seed money, you have to go one way, you can’t try multiple avenues.

After that, we did a crowd-funding campaign that brought in about a million and a half dollars for round one. It was through Circle-Up and we were only the 6th or 7th brand to use that, now you look and there are hundreds of brands on the platform but I think at our time there were only a handful.

We’re focused on round two of fundraising now, aiming for about five or six million to promote growth.

 One of the original Steve's Ice Cream stores

One of the original Steve's Ice Cream stores

What about some of your early challenges?

There is the hard road we decided to take early on, which was to own our own production.  That is really hard to do - to own 100% of your production and scale.

These days, we manufacture about 25% ourselves but utilize others for about 75%. We had the money we invested in equipment and the people which is all necessary to our success but when you have to make electricity and rent on a facility 100% every week, it makes a start-up much harder. Paying a co-packer once a month is do-able if you can still ensure the production is going to be up to your standards. Doing it all yourself though, that’s tough.  Rent is not a variable cost.

What were your early wins? Some moment where you felt, we’re doing this, it’s happening?

There are a few. One is definitely Whole Foods locally bringing it in. We didn’t want to wait for the regional approach so we approached them at a store level with Tribeca, Chelsea and Bowery along with a few others in the city, and were successful. We put a lot of effort in but it’s not like we were doing sampling every week in every store but it was turning and moving off shelves at a great pace. Then that success moved us up to the regional sales level.

That was a good sign to us that it was not only appealing to consumers but also to a retailer like Whole Foods. It was validation for us on the product from a quality standpoint and from an interest level that the flavors were resonating with our New York / Brooklyn consumer base.

Our investors make fun of us but we have the opposite problem of most start-ups. We always outsell what we can produce. In this industry, if you have enough money and are spending on sampling and deep sales every week, you can sell anything.

We didn’t have that luxury so whatever our sales and marketing budget would have been went into the product. But a product that was still at an affordable price. You can look at Jeni’s selling for $12 on the shelf next to us and we have a comparable (if not better) product selling for $6.99.

We also had farm stands in the summer in the Hamptons selling fifty cases a week. That was just incredible. It was validating to us and its what has kept us going, each year a new milestone has been reached.

Outside of a great product, what marketing efforts did you utilize?

Product demos were a key thing for both this market and northern California to grow us. We didn’t really do sales promotions to drive volume like a lot of new brands; we have promotions more for sampling purposes. They’ll try us for $5.99 but then they’ll like it and come back the next week for a full price because they’ve tried it.  Largely, a big part of the brand was also partnering with local brands. For Strawberry Ricotta we partnered with Salvatore in Brooklyn. We partnered with Ovenly, Blue Bottle, Taza Chocolate and a lot more. A huge part of our strategy was partnering with these brands that already have some credibility in the market.

We didn’t have street teams or anything like that though because we didn’t have budget for it, and most of our time and energy went into production. Being so close to the product taught us a lot about it, but with food and beverage, you know, for example, its really hard to have your own bottling line (editor’s note – The Barking Irons team knows!). It’s really hard to scale when you are doing all the production, but on the other hand it taught us so much early on.

What role did the legacy of the Steve’s brand play?

In terms of the legacy of Steve’s, it wasn’t so much that there was name recognition but we liked the story behind it. When we’re targeting – for better or worse – millennials or, well, me, there wasn’t going to be that name recognition. There were three hundred Steve’s shops in the mid 1980’s but the last one closed in the early 90’s, I was born in 1986.

People have bought into the product itself and the story is a secondary element. And, to be honest, marketing is something that I feel we are probably lacking the most. Now that we’re starting to have more time and I can step away from production however, we can start to tell the story of each flavor and start to take on our competition over the next five years.  

I think it will still be product driven but it has to be a little deeper in terms of story.

What about packaging? Were you the first with the clear carton?

We weren’t (laughs). I’ll be honest. Talenti was really the first to go clear and had that unique screw top. And Jeni’s and us came out around the same time but they’ve since gone back to cardboard.

I think the packaging was essential to our early success in terms of people seeing the product and the swirls and what actually goes into each pint. But, it was a huge design challenge because every flavor is a different color and we’ve had to go really simple with bold lettering and black to keep consistency across a shelf.

The other thing we decided to do from the start was to focus on flavor name over brand. If you look at the hierarchy of our packaging, flavor is the first thing you see. The second thing we’d like you to see is the base, either dairy or dairy-free. We differentiate that between white labels and black labels. And then, the third thing is brand. It’s not that we want to downplay the brand but right now people are choosing on flavor. Eventually as we build the brand awareness, we’ll bring the brand up to the forefront. For right now, we’re keeping flavor first.

There is a huge downside to clear packaging in terms of production but the upside is the true transparency of the product, from the finished product through to the whole supply chain and our sourcing ethos.  

A physical manifestation that is also a philosophy…  

Well, yes. That has also been a production issue though. If you are going to have that window, it better look good.

For example, one of the first people we outsourced our production to, we had an issue where they were short filling the pints. With cardboard, you’ll find a 1 to 2 oz. gap at the bottom with every brand, you just never know that because it melts by the time you get down there. Everyone fills the carton and then flips it so it freezes to a flat surface when you open the container. We don’t flip it to get that gap; we just do it because the lid is a sturdier base for freezing.

It took us months to figure out how not to have that gap in the bottom though, getting the entire product down to the bottom with the filler and then freezing it quicker to lose the gap.

Anyway, that’s the issue a lot of artisanal brands have, nailing those little production issues.

What types of things keep you up at night?

 I think the execution piece is huge. On both sides really, when we used to make it ourselves - you can’t make ice cream and not think about the recalls of the last year – as well as outsourcing.

Dairy, it’s not like a lot of other products, it’s a very volatile in the sense that it goes bad quickly and it is friendly to microbes, like listeria.  

That is one major thing that kept me up a lot last year.

But one of the reasons we decided to outsource some of our production was quality and consistency. Some things are out of our control like if something melts and re-freezes, you get a grainy pint of ice cream. We have a great staff that executes things properly but with a larger team, you make bigger batches, and you can be more consistent.

There are stricter product safety rules as well with these larger manufacturers that help me sleep better.

The downside of that is that we lose out on some of our smaller partners. An organic product like Taza chocolate won’t meet the standards of a larger manufacturer but, for us, it’s about working with them to grow along with us so we can continue our relationship.

It really comes down to product when it comes to what I worry about. This year, we’ll likely sell two to three million pints. I know that there are some bad pints in there – that is uncontrollable - but it’s hard to accept when you’re a control freak like me.

So, I try to tamper those inevitable disappointments with really great customer service and making sure that we’re taking care of people that may have had a bad experience, whether or not it was in our control.

That leads me to another question, with social media, how do you stay connected with your consumers?

We were scooping at Brooklyn Flea to get feedback on flavors, etc. initially. Early on, we did a lot of events to stay face to face with customers and hear their thoughts but that is waning a bit now.

In terms of social media, we’ve always had Twitter and Facebook but I think Instagram has been the primary driver for us. That’s how we mostly stay in touch and speak to consumers. We get a lot of feedback with Facebook as well though; people messaging us there with any negative experiences they may have had.  

How do you handle product development, innovation and new flavors?

Well, we have a smaller group of people, not focus groups because it’s not formal like that, but a smaller group of people that give us feedback in terms of flavors and new mix-ins that we’re working on.

Surveys are another thing we use, especially in regards to new flavors. This is a great example, we made a malted ice cream with mission figs in it and we did tastings with friends and family and contacts in the food industry and hands down it was the favorite. And then we send out a survey of “What would you buy of the following?” and that flavor came in dead last. Surveys are interesting because it gives us insights into what people will actually pick up.

 Strawberry ricotta is another good example. It got written up as the best ice cream in New York and had great press but we took it national and it just didn’t stick. Strawberry is a tough sell anyway which people don’t realize but on top of that, people “get” ricotta here but it’s not going to be as popular in the Pacific Northwest and the West Coast. It just didn’t sell well.

 It taught us that you need to be innovative but you need to stay with something that people can identify and are still somewhat comfortable with. Twists on classics instead of going super crazy, at least in packaged pints. I think that’s a real key.

This year we plan on adding some brand ambassadors and we’re launching a 4 oz. cup, so we can easily get into some non-traditional sampling venues and do more events with those cups as well. The cups are really more of a self-funded marketing vehicle for us, not as much about revenue stream.

We’re in talks with JetBlue to make something happen, college campuses, tech company kitchens; those are sampling opportunities for us. If we can break even but get in front of those audiences, that is what’s important.

Sampling in our focus cities – NY, SF, LA, Boston and Chicago are our key five markets –and getting people on the ground there to do sampling is going to be a priority. And then, connecting with our small demographic whether that’s at Outside Lands or Coachella or even a small greenmarket, the focus is going to be getting to our people that identify with our values.

We have a great team but we’re all based here and I can only fly out so much. We need people on the ground in those markets to really build.

So, two people, you and Dave, any challenges you find working together?

Oh yeah! (Laughs) All the time. I think tension is a good thing. Dave and I are very similar in a lot of ways which is great but can also cause it’s own set of problems. I don’t think we balance each other out as much as two business partners probably should. We have a lot of the same positives and a lot of the same negatives as opposed to if you had two business partners that were more complementary.

Dave is older and has more experience in the industry. I’m younger and am more tied in to the so-called “Brooklyn” market that really just means our target demographic. Packaging is one thing where we butt heads a lot. I think a lot of times it’s positive tension where the end product is something better than one of us would’ve done individually though.

I’m not married, I’m getting married next year but I imagine that having a business partner is harder than a marriage. I think my business problems cause more of my relationship problems than vice versa. (Laughs) 

To Dave’s credit though, he gives me a lot of latitude to try what I want to do. And there’s definitely more positives to our partnership than negatives.  

It all depends on what challenges the business faces and how you grow. There are times now, because we know that packaging is something we’ll disagree on, we’ll bring in a third party to weigh in and then it turns out even better.

You come to these realizations that you view the world and prioritize things differently so you will disagree. To me, I prioritize fairness. If someone isn’t pulling his or her weight, it is putting everyone else’s job in jeopardy. Dave for example, would probably cherish kindness at the top. From a moral standpoint, I can respect that but from a business standpoint, I’m like, you can’t be kind all the time. You can be kind to an extent but not to these people that aren’t being fair.

You learn a lot about yourself from all the stress. I think if nothing else, if it doesn’t make you a better person, it gives you much better personal awareness of strengths, weaknesses and what you prioritize what you personally value.  

You alluded to the fact that six years of business feels like twelve. I think entrepreneurship is an inherently intense experience, what have you learned about yourself in the past six years?

I would hope that what most people would learn is just resilience. I think most people are far more resilient than what they give themselves credit for. I know I’ve learned that.

Also, you learn what you cherish most. It’s an intense process that puts you under extreme stress. There are plenty of times where you are like, what the fuck am I doing? Why am I doing this? Ice cream is great but I’m being pushed to the brink over ice cream?!

It’s this absurdist thing. I hope that people take a step back and think when they’re having those overwhelming moments.  

It’s this Sisyphean thing. You’re not in it for the end result but you’re in it for the process of it and seeing where the process goes. Take a step back, take a deep breath and things will just happen.
You’re always wondering, what are my competitors doing? Are we winning? Is everyone happy?

You have all these worries and stressors and you’re not necessarily even paying yourself. Our problems haven’t diminished; we’re in a stage of growth where it’s almost scarier now. If we have big mistakes, it can put us out of business. When you’re little and mess up a batch, it will cost you a small amount, if you mess up when you’re big, you lose millions of dollars.

We’re in this scary time but I think that you have to let go a little bit and think strategically but also know that, yes, things will go wrong and you just have to cherish what’s going on in the day to day.

I used to spend eighty hours a week working. Now, I spent more time with my fiancée and only do sixty hours a week but have a clearer head and that’s better for the business and worth one hundred hours or more, in the end.  

This also teaches you how to take care of yourself. If you don’t, you’ll go out of business.

And you’ll ruin your health.

I’ve just started getting healthy again personally. I probably put on sixty pounds since I started here. Not from eating ice cream but from stress. The last six to twelve months, I’ve had a slow revelation that taking care of yourself is not only something you should do personally but it’s also a responsibility to your staff. If I am burnt out and don’t deliver for our people, well, it all comes back to that fairness thing.


It’s all about balance. Balance in taking care of yourself, balance in being “in it” versus stepping back. For six years I’ve been so tactical, fighting it out in the trenches. It’s hard but you have to step back, look at things strategically and put the right people in the right places in order to execute those things if we’re going to succeed and become a bigger brand.

Your business goes through different stages. It’s like a child. Your business is two and you figure out what it wants and then it turns three and everything is different.  


Did you have any mentors when you were younger that played a really significant role in shaping who you are today?

When I was in fifth or sixth grade, I was tutored by an old physicist; an older gentleman that had retired, Murray. Oddly, when I was younger, I was more of a math and science person. He definitely had a huge impact on my life and into what I became. I studied so much in physics and math. Had it not been for this, I think I’d probably be an aerospace engineer or something like that.

Then, in college, I ended up working at my first real job. My boss there was a young guy, Eli. He was probably the best professional mentor. I went to a very progressive boarding school in Colorado and was at Columbia at the time. He guided me how to have fun at work but be professional at the same time and navigate that transition of coming from the academic world to the professional world. Eli gave me the professional confidence to start something as a co-founder.


Any advice for someone that is just starting out?  

Don’t get into the food and beverage industry (laughs).  

Everyone says that same joke; I love it.  

If you look back and think, would I do this all over again? I would definitely say yes. I think the biggest advice is to go slow. A good example is People’s Pops, who are down the hall. They want to expand and my advice was, pick 50 retail customers and do a really good job with them. Don’t just take on every one. If you focus on a few things and do it really well, that’s a better recipe for success than doing too much and doing things in a mediocre way. That’s something we learned the hard way by trying to grow too fast.

Success in the food and beverage business and maybe more broadly, I think it is the 40/40/10/10 rule. 40% is tenacity. When we were about to go out of business, we just stuck in there. I think a lot of people go out of business because they’re just tired of dealing with things.

The other 40% is serendipity. Timing is huge. We have certainly been a part of a renaissance of new ice cream. Had we launched in the mid-90’s we would’ve gone out of business in a year. People were only buying Haagen Daaz and Ben & Jerry’s but lucky for us the average Ben & Jerry’s eater is now over the age of 55.  

Then, another 10% is strategy. All those things that go into have a good plan and a good product.

And the final 10% is listening. Listening with a discerning ear but listening to buyers, consumers, retailers, and the people with something valuable to share. Distributors as well, I actively solicit feedback from our distributors. A lot of times you can drink your own Kool-Aid and think you have the best product on the market that can’t be improved and that is a recipe for disaster. I know we have a great product if it is executed correctly but I always am looking to be more innovative.

Any hopes for the upcoming election?  

Business wise. I don’t think so. Personally I am a Hillary supporter. Bernie has a great message and I think it would be nice if some of that could be incorporated into the next President’s platform but on the democratic side, I think it would be good for a woman to be president. Trump would be a disaster (laughs).

For me, I see people fighting on Facebook - if Bernie gets elected, we’ll have to pay too much in taxes, Trump will do this, etc. - but whoever is elected, I don’t see there being a huge impact on business. Even with Trump honestly.

There’s that argument that luxury items are the first to go when times are tough but I think that is a really outdated way of thinking. I think people are prioritizing their food purchases, even in ice cream, and making responsible selections, both environmentally and socially. Even if we were going to go into slow economic growth, I don’t think that would affect our market share.

Final question, what’s the vision for the company?

We’d love to open a factory store here in Brooklyn where we could innovate and have the one-on-one face-to-face connection with consumers. I don’t think we’d go heavily into the retail space but maybe one here and one in LA to balance out the coasts.

We’re also coming out with regional flavors that appeal to the southwest or the northeast with local partners. Once our new production model of outsourcing some production is fully figured out, we’ll work on expanding that line of catering to more regional and niche taste.

I also think cups are going to be a huge thing for getting into those alternative spaces I mentioned for sampling. And not in the near future but we’ve also played around with a novelty item like an ice cream sandwich or a cake. My personal dream is to do a small packaged ice cream cake, not like Carvel but just a small cake. Maybe no one else wants it but I do.

And really just coming up on new flavors, take matcha for example. You’ve seen matcha shops popping up all over the coasts in the last few years. We’ve tried a few variations but one we’re working on now is a matcha mint chip; black sesame chocolate chips and a matcha mint base. That’s taking something that people recognize but partnering it with something on trend that is exciting to try.

In general, new flavors, new packaging and finally, building our brand story. There is such a story behind each flavor and each creation that will help tell the Steve’s story more. And in that, with our co-brands, as we grow, we’ll help our partners to scale with us.

Shana Tabor | In God We Trust

From the moment I stepped into In God We Trust’s Shop and studio in Brooklyn I knew I was in a special place.  Brooke, the long time friend of founder Shana Tabor, greeted me with a disarming charm and from then on I was swept up in the unique energy of this creative studio.  At a time when ‘culture’ is the buzzword on the cover of every business magazine, In God We Trust seems to have found a way of being, a vibe, all its own, and not easily summed up in words.  It’s a testament to Shana’s vision, and the community of people she works with every day.

Shana’s story is the story of an artist, and it begins when, as a kid, she discovered a passion for making clothes with her grandmother’s sewing machine. Later, inspired by two art teachers from her youth, she followed her passion for design to the city where she graduated from FIT before opening In God We Trust’s first shop in 2005. 

Over the past decade her brand has evolved to include clothing, jewelry, men's and women's accessories and a burgeoning wedding band collection, all made locally in the US. There are currently three stand-alone locations in New York and Shana and her team manage a successful e-commerce site while supplying other retailers with their goods as well.  

I thought Shana would be perfect for By The Bootstraps based on a recommendation from previous Bootstrap subjects, David and Kavi Moltz of D.S. and Durga. David worked at St. Helen’s Café on Williamsburg’s Wythe Avenue, across the street from In God We Trust’s initial store, back when the neighborhood looked and felt a lot different than it does today.

I sat down with Shana in her Greenpoint Avenue location last week to discuss everything from the growing pains of a brand, to her creative process, to her hopes for the upcoming election.

First things first, how did you find your passion?

It actually stems from an internal conversation, which was based on something I felt from my parents and a lot of other adults that I was around when I was a child...it seemed that these adults were all miserable with their work and lifestyle. Meanwhile, that work was where they spent most of their waking hours. I came to the early conclusion that I wanted to choose a path that would make me happier – something that wouldn’t have to be this life-long drudgery of, “Work? Blech”! Or, worse, waiting to be your true self until after you’d left work every day.

I asked myself, what are some things that I enjoy doing? More than design it was attached to construction. I learned how to sew when I was really young. Being able to take my mother’s old clothing or things I’d find at thrift stores and turn it into something I wanted to wear, that was really exciting to me.

I was also really fortunate that my public school in New Hampshire, starting at 12 years old, had a jewelry program.  I’m pretty sure in hindsight that one of my teachers must have been a jeweler and fought to have a studio in our high school as well as basic metalsmith-ing in the junior high school.

I was so lucky and I also loved her so I think that made me want to follow a design path as well.  

My parents were also really supportive to both my brother and I. I actually didn’t realize that was abnormal until I was in college and my roommate told me that her parents were upset with her for pursuing fashion design. It never even occurred to me that having parents like that was a thing.

You started at FIT, how did that lead to In God We Trust?  

I actually went to school for apparel-making at first. Then, being in New York and being immersed in that culture a little bit more, I thought it wasn’t as much for me. I knew I’d come back to it eventually but I didn’t want to spend my life wholly in that industry. Now I know that anything can be what you make of it yourself, but at that time anyway, it all felt pretty toxic… the schedule, the environment, etc.

Jewelry making was always something I enjoyed doing, but didn’t realize it was a career path until that time. As opposed to fashion, jewelry design wasn’t an art that required you to live in only one of three major cities or that you work at a fashion company, and there were options: you could be a bench jeweler, or be the only jeweler in a small city. There were endless possibilities.  I committed to the jewelry design program and graduated, and then I did a handful of jobs working in accessories and jewelry. These jobs were all at bigger “fashion companies” making costume jewelry, and it was exactly like working in fashion, so that’s when I realized something was still wrong.  That world is a weird world – I was in an office Monday through Friday, 9am to 5pm, which is really 9am to 8 or 9pm, and emotionally, I was slipping away and not enjoying myself.

I had a really good friend who I was complaining to one night and he bluntly told me, “Stop doing this, this is your choice. There is an element here that you love or else you would stop completely”.

For some reason that really resonated with me. The very next day I quit my job and just said, “Fuck it”, I’ll figure it out.

Then I spent two years just kind of…

Figuring it out? (Laughs).

Well, this was 2002/2003, New York was a lot cheaper then and it’s not like I was making great salaries anyway so spending a couple years of being really broke? That was OK. As long as I could make enough money to pay my rent, I was good.

The whole DIY/customizing stuff was really a thing then so I got a lot of random event-based projects. Teen Vogue would hire me to show up with paint and a sewing machine and ruin your jeans (laughs).

Based on the success of one event, I’d get a recommendation for another brand or magazine to come and ruin their customer’s jeans and that was enough work to get me through and scrape by.

Fun times?

Yeah it was awesome! I’m so pleased that I even allowed myself that time to have freedom and figure out who I was.

Of course there was too much partying, too much working, all that stuff… but it was all on my own terms and that’s what was great. I could choose what I wanted to do.

I read that a few friends’ shops picked up your custom pieces, then you found some success and you had your brother’s support as well. Was there a moment where you thought this could be bigger than supplying for other people? How did the shop first come about?

I thought of the first shop as a baby step. I was merely taking my studio out of my bedroom and moving it into somewhere else. I also had a handful of friends that had small businesses and when you’re in your mid-20’s, trying to figure it all out that type of stuff is really important. Aside from myself having any entrepreneurial spirit, it was in my community and all around me.

I had also been selling jewelry to this store called The Good, The Bad & The Ugly.  The designer’s name was Judi Rosen and she had a shop on North 9th between First Avenue and A back then. She had a small studio space and a shop in the front and I thought she was so cool and that inspired what I wanted to do for me. (Editor’s note, that shop later moved onto Kenmare and Rosen found some success in the late 2000’s before eventually shuttering in an epic closing party.)

I got that space on Wythe between N.7th and N.8th in Williamsburg and just figured I’ll try it. I thought, “Can I make it work? I don’t know but I’ll give it a shot.”

There is this other interesting element about running a business. In hindsight, this is kind of an apology to a friend…  I had a roommate that had this shop with one-of-a-kind, small objects, art, etc. She was awesome and continues to be awesome, but when we lived together I always gave her a bazillion opinions of what I thought could work for her shop. Then, when I actually had to deal with those challenges myself I was like, “OK, now I understand what you were talking about and dealing with all those years and I’m sorry.”

People still do that to me now, “Oh, what if you just did this?” “I’m sorry but do you take care of your three stores better than I am taking care of my three stores right now? Oh, that’s right, you don’t have three stores, shut the fuck up.” (Laughs)

It was a huge personal learning moment though, owning my own place, you just don’t know. Even to me the smallest mundane things were the ones you don’t think about: I have to make sure the toilet paper is here. I have to make sure the receipt paper is in. I have to make sure the lights are on and the light bulbs work. Not even the cooler, bigger picture creative stuff, just the day to day.

So that mundane stuff, were those the early struggles? If not, what were the early struggles?

I get bored easily so the different, jack-of-all-trades, master-of-none tasks?  The stress of those things helps me thrive.

I’m also sort of terrified by the government and being up to date on taxes and stuff, so I’d rather just play by the books and have everything taken care of. I have a great bookkeeper/accountant whom I’ve worked with since the beginning who has really helped with that.

That’s great. Any early wins that you remember that made it feel like you were on the right path? Any time when you felt like you were ready to think about next steps?

I still am humbled to this day when I see people in my jewelry or clothing in the real world.

I do remember a time when the store was open for a year and a half and other acquaintances I knew that were business owners were opening second locations.  I thought to myself, “Is this something I want?  Am I supposed to want this to get bigger?” Or, “Should I be working towards something more?”

So that turned into me finding a space in the city, and that point was eye opening for me because it meant I was taking this real, but not really real business into – well, this is how you run a business… You need to get a business loan. You need to sign a release. You need to do a build-out a space. It was very real and very scary. What if it doesn’t go well?

But, as cheesy as it is, I like to believe that if people are being honest with themselves and their work is honest, then it will be successful. If you work hard and you’re honest, then you’ll be successful. Whether that is Donald Trump’s version of success or not, I don’t know. I think I’ve always been that way though.

You trusted your gut and believed in yourself!

I think that people can get in their own way. They overthink things and obsess, but you have to just go for it. No one is going to turn around and say, “Well, you failed and I’m not going to be friends with you or love you anymore” (laughs) and if they do, then you don’t want them around anyway!

Did you have any major setbacks then? It seemed like your model to grow was incremental rather than massive and ‘all-in’.

I think personally and professionally, if you can’t afford something then you shouldn’t have it, and emotionally, if you can’t handle something then you shouldn’t try it. For us, it’s always been baby steps. This is our size and it’s good for us, and we do it in steps that make sense for us.

I always feel bad for people that have investors that have a shit ton of money put into a space and then they sat on a space for 6 to 12 months and then they finally open and no one is buying things. What are you going to do when that closes? Get a design job somewhere and pay off $500,000 worth of debt? I guess people think, “Go big or go home.”  But that’s just not me.

As you grow, how do you adapt your business?

I think it’s about understanding your customer but also about trusting yourself. This business has changed so much, aesthetic wise… interest wise. In the past 11 years, I’m not thinking, “Oh, we still have to appeal to this set of people.”  But in my personal life, I’ve changed a lot, so my personal tastes have changed and the business goes with that. I’ve got kids now, you know?

I’d like to think that my people and customers are growing with us. I opened the store when I was 27 and I’m 38 now. Look at our wedding and engagement rings; if I had tried to sell those then, I probably would’ve gone out of business.

It seems like family and community are important to you.

I’m actually starting to feel less rooted in this community. We certainly have our network and friends but I live in Williamsburg and I work here, but looking around here lately it’s like, what is going on here? And quite frankly, do I even care?

That could just be that I’m getting old though.

It’s funny, I live in Carroll Gardens and can’t believe how much change is happening and how many buildings are going up…still.

Yes, in New York, especially in Brooklyn, but it seems to be happening everywhere. There is this crazy momentum in Austin and Portland and everywhere and I don’t really know what’s driving that… at one point can people just not afford to live anymore? And at what point does it just bottom out and go back to normal?

I think a huge success of our business was timing. When we opened, there wasn’t a lot of competition. And I never would’ve considered our ‘competition’ our competition because we were just community. That’s just not how we functioned. We were one of four boutiques in Williamsburg, now we’re one of four on the block. What, where, who are all these people?

Jewelry, specifically, when I started there were maybe 3 other people who I’d consider my contemporaries - speaking to my audience, around my price point - and we were all friends.

Now, everybody and their goddamned mom has a jewelry line. I’d like to continue to believe that our stuff is unique and persevere but it makes me doubt how our stuff is different than this person’s stuff or this person's stuff. We’ve had our name and been around for 10 years but does the average 24 to 30 year old consumer care about that? They only care about how many Instagram followers you have. I think we’re living in a weird, very transitional time. How old are you?


I think we’re at a very fortunate and interesting age where, up until this point, half of our lives have been manual.

You mean offline.

Yeah, and the other half has been automatic. Basically, we’re fortunate enough to understand what life is like without email, the Internet, without a cell phone… but still know how to use and harness all this technology. We also appreciate how fortunate we are to have it. Sometimes we forget.

I was saying at the beginning of our conversation. To work in fashion, you had to be in NY, LA (maybe), Milan, or Paris if you wanted a career. But now you can live in Ohio and have a dope fashion brand and have followers all over the place and everyone knows what you ate for breakfast.

Even fast fashion, when I was a kid, I couldn’t go to Bradley’s and buy fashionable leggings with a zipper on the side. You wore dorky kids clothes because that’s what was there.

Now, everyone is cool, and nothing means anything. I’m not bitter, I don’t want it to seem like I’m being super negative.  It’s just weird.

There was an exclusivity thing, growing up, if you were into The Smiths or Stone Roses, you would see a t-shirt and connect to a person.

You could see that person on the street. Growing up, for me to buy a pair of fishnets or a pair of Doc Martens, I had to lie to my parents, save enough money to get on a bus, and then figure out how to get to Boston to Newbury Street to seek out those places to buy stuff. Or figure out cool mix tapes to get from weird bands.  If you were out on the street you might see someone skateboarding with a Minor Threat t-shirt on and that meant something, whereas now, you could say to someone, “I like your shirt.”  and they might just say, “I don’t know who this is.” If you want to be cool now, you don’t even have to try. You can walk into Forever 21 and buy a Nirvana t-shirt; there is zero credibility and a lack of authenticity in things.

It does make things less special now that everything is available everywhere.  At the same time those passions are more available for people who don’t have access to those major hubs. How do you operate in that environment? You said you worry but do you worry in a broader sense about the world, or is it more of a business sense of how do you stay relevant?

I think we have to be aware. Not to pull out some Dazed and Confused shit but I keep getting older and the people I work with stay the same age, 22 through 27. And, I very much, to a flaw even, assume everyone is the same age as me. Not where I think everyone is 38, but where we’re all just existing at the same mindset.  But the truth is that I actually could be your mother. You are 22, if I decided to not go to college, I could’ve been your mom. Like, “How old is my coworker’s mom?” And, “When are we going to drinks?” (Just kidding).

I’m not going to say that all millennials are horrible, because that’s not true.  It’s all comes down to the person. One of my favorite people that I work with is 23. She acts older than I do and she listens to real music and is just an awesome person. It doesn’t matter how old she is or when she was born.

So that’s a good point with the kids. Now you have a team. In the beginning, you were doing things on your own and you were creating all the designs yourself. At some point, you shift from being the sole creative energy and you bring people in and…

I still do believe that I’m the sole creative energy for the overall brand, but I do work with other people on stuff.

On apparel, the woman I work with on apparel, I definitely let her take as much creative freedom as she wants.  I need her to feel that this is just as much hers as it is mine, so it’s a collaboration.

But generally speaking, I really like working as part of a team but I always bring ideas to the table as, “This is open for conversation.” I like working with people.

I try as much as possible creatively to include people and work as a team so that people have ownership and feel invested. This isn’t just about me. I think that’s partly why people that have chosen to work here over somewhere else.

I noticed that you use the term co-worker rather than employee.

I think it’s gross. I don’t feel comfortable with using employee. I hate it if I’m out in the real world with one of my co-workers and they introduce me as their boss. It’s just so loaded. Now all of the sudden you can’t have fun, you can’t swear, you can’t say something stupid. Even if they don’t mean it that way, I can almost see it on their friend’s face.

Like, “Oh we won’t talk about last night.” :/

Like Lumbergh from Office Space…”Boss” does have a bad connotation. I like that. Ok, final few questions. From an aesthetic/artistic side, do you have a vision? Do you ever have dreams about that stuff?

Sometimes. I wish I could turn it on more but I think I’m more attracted to shapes/silhouettes that I want to be wearing. When I do have those a-ha moments, my favorite is when I think I’m seeing something but it’s actually totally different. But what I thought I saw was what I wanted to make. One day I was talking to a friend and I saw her amazing earrings but I made this thing up in my head of what it was because it was actually just two earrings in a weird position, and now I can make it because I saw the final product in my head. I wish I could have that all the time.  Then I could rule the world! (just kidding).

Inspiration comes from a constant conversation in your head.

You just have to make notes of it when it happens so when you dry up you have something to go to.

Most of my emails are from myself because I’m constantly sending ideas to myself. Almost the last question:  As a business owner, the upcoming election, anything that you’re hoping to see happen?

I think most of the stuff I want to see is more personally driven. I’m not sure I’ve thought of it that much from a business-owner point of view. I probably should (laughs). I will come out and say that I’m a Bernie Sanders supporter. I think everything that he has to say is great and it would be awesome if it all actually happened.

There is a lot of shit you have to deal with as a business owner. It’s so stupid and crazy with the government. The healthcare stuff we’ve been dealing with is such a nightmare. I do find myself sort of torn because I want this to be awesome and great and I want to be supportive of it but it is actually a nightmare. They should make it all easier to deal with.

What are you most proud of?

My daughters. Is that cheesy? They’re twins, they’re 15 months old.

What advice would you have for someone starting out?

Work your buns off. Work a shit ton. Buy something proper the first time around, especially as far as tools are concerned. Buy a nice drill or buy the pliers that work properly so you don’t spend more money buying that same item ten times over.

Invest in yourself?

Yes! Except some people may take that the wrong way and think they should get a manicure or something. (Laughs)

Andrew Steinthal & Chris Stang | The Infatuation

Chris Stang and Andrew Steinthal met on the set of TRL in 2000. The two were in town for CMJ; both working for their college radio stations, and Destiny’s Child was the guest, promoting their new single “Jumpin Jumpin”. On the show they stood directly behind Carson Daly, but they were quickly moved off-screen for not being enthusiastic enough.

I was actually a producer at TRL, but I didn’t meet the guys until several years later through a mutual friend of ours in the music industry (shout out @Kennys_Liver).  We hit it off immediately and Phear Creative helped them edit one of the Infatuation’s first video’s -  “Cookies Across The City."

That was back in the early days of The Infatuation, when both Stang and Steinthal were in the middle of successful music careers and The Infatuation was a project they did on the side.  But since then The Infatuation has become a global community of unpretentious food explorers, connecting millions of people through a shared passion for ‘food for the people’.

I sat down with Stang and Steinthal at their downtown NY office space (unfortunately not over any #EEEEEATS) to learn about how they made it all happen.  It was a real conversation; for topics (media, food, entertainment) that are often riddled with jargon and BS, the insights these guys shared are refreshingly honest and incisive.

So tell me about the beginnings right after your TRL-based friendship (you’re welcome), how did things start?

Stang: We graduated in 2002, moved to New York and began ascending in the music ranks together.

Steinthal: That was 14 years ago. We started the site in 2009, but we were still working in music up until April 2014.

So a full five years where you guys were doing the day and night job thing, wow. Before we get into that though, when you started in 2009, what was the initial inspiration?

Stang: We felt like there wasn't a voice for the average diner as it pertained to restaurant discovery. We were 20-somethings with corporate cards and loved going out to eat but the closest thing that was useful was New York magazine, which didn’t really strike a nerve at the time for us. We wound up as the guys in our crew of friends who were always getting phone calls being like, “Hey you know the city well, where should I go take my girl out to eat?” Or, “I want to go for some late night food.”  Maybe, “I want to go scope some hot girls” or “My parents are in town.” We had a lot of different business ideas over the years but had never settled on something until this.

Steinthal: It was either this or a t-shirt company. This seemed like a better idea.

Stang: We felt like there was an opportunity. There was a hole in the market. We looked around and Zagat didn't really matter any more and there was an opening for a restaurant review resource that was useful, fun, and entertaining. Also we wanted to make something that was for everybody as opposed to just this super niche group of people who subscribe to Bon Apetit and read the New York Times and consider themselves super foodies. We were just regular guys who loved to go out to eat. We weren't experts by any means, but I think that most people related to that. We decided to start writing restaurant reviews, categorize everything by “perfect fors” and made the site something of a utility that would help people find different restaurants for different needs and experiences.

Steinthal: The concept wasn't new. It wasn't like there weren’t places covering restaurants. It was really just about the voice and the way we approached it, which was to come from a much more relatable point of view.

When you started it you said it was either a t-shirt company or this. Was there a grand vision, you guys wanted to start a business for the long term? Or were you like lets just do this and see how it goes?

Stang: I think we’ve always had an entrepreneurial spirit. We would tinker around with different things, but it was never that serious. I think we made one t-shirt. (Laughs) Around the time we started talking about this, I was going to be in this NY Post bachelor column and I made the ultimatum. I was like we have to launch this thing before that runs.  (Editor’s note, we found the article, you had great hair in 1999!)

Steinthal: Once we had a few reviews up and people started getting back to us, it was like, cool, this is actually something that people want.

Your partnership seems important. Do you think your friendship played a role in this being successful?

Steinthal: Yeah. This kid right here is my best friend. It was obvious from the first night that we ever hung out that we were going to go do shit together.

Stang: We obviously connected immediately as people but I also remember from day one thinking that if we put our heads together, we could make stuff happen. Probably something to do with being 19 or 20 years old sipping Bud Lights and us being cocky (laughs) but that persistence was always there. For whatever reason, we felt like if we tackle problems together, we could make it work.

Steinthal: That's why the analogy about the t-shirt company is relevant. Had we really pursued the t-shirt company seriously, we probably would have made something out of that. I don't know what it would have resulted in but knowing our personality types we wouldn't have just half-assed it.  

After five years of doubling up, but how did you guys decide to sync up in leaving your day jobs? Did that happen at the same time for both of you?

Steinthal: Our first Turkey Leg Ball was the real eye opening moment for both of us.  We sold $20,000 worth of sponsorships, which is insane to look at now (it has since grown considerably), but it was the most memorable one. We were able to put tickets on sale for $25 so that people could come. We put a few hundred tickets on sale, went into a meeting, and the thing was sold out by the time we finished.

Stang: That was a very important moment. Also, around that time, we were sitting in a restaurant with a filmmaker friend of ours debating the merits of Twitter or something for our businesses. The woman sitting next to us was like; I just over heard the conversation, what do you guys do? We mentioned the website and she’d heard of us. It was like, do you know my mom? Turns out she’s a journalist from the New York Times and she ends up writing a story that had us on the front page of the dining section. When that got published we went from having a couple of hundred visits a day to the site to thousands, overnight. Anyway, the reality is we got to grow The Infatuation because we had great jobs and great salaries and the support of the people we worked for. Not a lot of people get that luxury of being able to do both.

Steinthal: Building an authentic voice is what we wanted to do and still are. That takes time so having the luxury that Chris was talking about, having full time jobs, having people that supported us gave us the opportunity to slow play this and build over the course of 5 years. That time was a Godsend for us because it really helped us establish ourselves.

And were there any tough moments? Dark nights of the soul where you wanted to throw in the towel?

Steinthal: We have not bottomed out ever. You have good days; you have bad days.

Stang: I don't think either of us has seriously considered giving up. It's not easy, that's for sure. From my perspective, the fundraising stuff has been tough. Raising money, especially from the venture capital world, is just an insane process. It's a lot like the A&R industry in music. There are a couple visionaries that see stuff coming and they really do have an eye for the things that are disruptive (or whatever the key words are) but there are also lots of people that are just following or chasing those trends.


Stang: Yeah, let’s find the Skrillex or whatever it is and you see all these other guys just chasing it, when the visionaries are three steps ahead of them anyway. We’ve been told creating high quality content and scaling it is way too hard, and we were just sitting there like, “Watch us.”

A lot of people say that the big factor is determination. There are plenty of businesses that wouldn't have made it if they didn't hang in there during the tough times…

Steinthal: If you have the determination, yes, but you also have to have differentiation.  

Stang: I think adaptation is required too. That’s something we've felt probably more in the last few years. You got to keep your head up, look around and see what the world is telling you to invest in.

I would think that in your space, there is a lot of that. The media landscape has certainly changed quite a bit. We deal with that in our agency but what are some of the other platforms or opportunities that you’ve embraced or taken a chance on?

Steinthal: I think we have always been very early adopters on whatever the new social platforms are where there are community-building opportunities. In 2009, we started on Twitter. We started butting into conversations, very music-based style grassroots marketing. We even got kicked off Yelp because we would post little sections of our reviews just to try to get some eye balls and drive people back to the website… every opportunity to tap into other communities and bring them back to ours.

Stang: Instagram was the huge thing for us. We didn't know at the beginning how big it was going to be and very easily could have missed it because we didn’t think it was exactly right for us at the start. Others waited and then saw it explode and now they're chasing it, trying to catch up to everybody else.

Steinthal: We were definitely one of the first brands on there with a branded hash tag. We’ve done almost two million globally now with #EEEEEATS. It's become this crazy thing, now everybody has their own hash tag and wants you to use theirs for a re-gram but we were one of the firsts to blaze that trail.

Now, we have sixteen Instagram accounts across all different markets - @pizza which we run with @fuckjerry, @pasta, @tacos, @icecream, @coffee, etc. - and we have all these accounts that are growing that give us more inventory to sell against. We have a nice presence on the web but we are not massive in the way that…

Stang: We are not Buzzfeed and we will never be. We are never going to be considered in that way in the way digital ad dollars flow now but we can go in and pitch because we can beat some of our competitors in social reach. Quite frankly, the social reach is more valuable than banners and things like that now. And we are doing 60 million impressions on Instagram a month.

Steinthal: Yeah, when you add up all of our accounts and everything that's going on, we can go and compete but its still the Wild West out there. First, a lot of the money that was in TV flowed into display and banner advertising and now, that money is flowing more towards social and engaging niche communities. The struggle is everybody is trying to figure out what the metrics are to show success but everybody has different KPIs right now. You cannot fit the current state of social impressions into the old model of web impressions but that’s what people are trying to do. Something new has to be created for this new world. We are in that place right now, did work with your client Jameson, did something with Budweiser, Burton snowboards, Paige denim…it is fun to be working in this space and using Instagram as our big reach but then powering campaigns with great content as well.

Food has become much more of a passion for people than ever before, and your name, The Infatuation, speaks to the passion that people have for food. If people care about food so much, how are you seeing that passion manifest itself?

Steinthal:  Now you just start an Instagram. That's the new version of food blogging. All these kids that we see… there's a million of them. It's awesome because all these people feel like they can have a voice and express themselves and participate and seeing that happening is just amazing.

We hear from people all the time, and that's been really cool and gratifying. We get emails from people that are like, “You guys inspired me to start a food blog in Instagram!” or whatever it is.  It's so much easier now to start an Instagram and put up a blog on medium or something and post recipes. There's nothing stopping you from doing that and building an audience. It's only becoming more and more easy.

Stang: It's crazy how young the kids are when they start. You think 14 year olds are into One Direction or whatever, but no they're taking pictures of ice cream cones and are obsessed with food.  We did an influencer event recently.  This one kid rolls in with his mom and the door person was giving the mom a hard time. I went there and he's like I don't have this woman on the list and the she is like no, this is my son. He is @EatingNewYork; he's got 70k+ followers. He's literally 14, maybe 13.  

Steinthal: My old boss sent me a link to his daughter's Instagram saying, “Do you see what you've done?” It's his 14-year-old daughter and her friend taking pictures of their ice cream.

Stang: Now what we are really starting to think about is how can we then be the people that help these kids who are just now discovering their passion for food. We want to be the brand that they know and turn to when they are finally living in a major city. We want to get to them early and be that brand that they trust but also how can we then help them to further pursue that passion?

Stang: To say that we saw [Instagram] coming in as our biggest platform would be false.  We followed it and it has evolved into being this incredible platform for us.

Let’s talk about vision a little bit. Instagram became a success for you, what else are you looking at as being something big down the line? I know you launched your messaging service [Text Rex] last year…

Steinthal: Snapchat is also really interesting to us but in terms of the way our business will develop, I think messaging is going to probably have a lot to do with how we grow as well as how we make money. Right now our business model is brand partnerships. We do integrated partnerships that are powered by content and usually involve some form of social activation and potentially some influencer strategy, events offline that create a moment. The excitement around text and how that could look in terms of future business though… we have already heard from a bunch of our clients that they are interested in that so we’re excited to see where it goes.  

That’s great about messaging, seems like you guys can innovate within that space. Where do you see this going otherwise? How big you want it to grow?

Stang: The nice thing for us is that people identify with us, our story and the fact that we are two people with a passion about food who simply started expressing that, built a following and found credibility without having any credentials. It would be harder for us to go out and find seasoned food writers to train into our mold. We are uncovering all these people who are amazing, creative and smart with a passion for food and then we just polish them into our voice. What we are trying to do is build a machine, find these people and help them grow with us. We literally get emails every single day from people all around the world saying “Can you please start Infatuation in Berlin?” or “Can I please start Infatuation in Houston?” We’d love to be able to set up a system where, “You know what, you're the right person. Here are the resources. Go run with it!”

Last two questions, any advice for people starting out?

Stang: You have to be passionate about it and you have to care. A lot of people get into stuff because they want to be entrepreneurial by solving some market problem. But if you have this thing inside of you, there is no reason you cannot do it, just start on some level.

Steinthal: And you need some kind of an idea that's different. So many people start so many things that are exactly the same, which is very confusing to me. You can see all these delivery services now. . I'm like how many more delivery services can there possibly be for food? How do you differentiate? Only some of them are successful and ultimately only one or two of them are going to win. Even if you’re just writing your own blog, it just needs to have a voice that's a little different to stick out from the crowd. If it's not, nobody is going to care. Those are my thoughts.

Thanks so much. That was great. Finally, the upcoming election, you guys are business owners, is there anything from a legislation standpoint that you guys would like to see happen?

Stang: Nationalized healthcare. Not kidding. I'll get into this because it makes me angry. This is not just a political issue. Certain politicians will preach about how small business is what drives the economy and how we have to empower small businesses but a huge portion of our monthly expense is mandated healthcare for employees…to the point where if that wasn't there, we could hire two more people, today. I'm feeling the burden.

Steinthal: It's more complicated than just nationalized or not but I do think that at some point, someone has to figure out how to actually start to solve the problem. It may not be right or left but someone has got to seriously say, “How do we make it cheaper to take care of people?” There are companies out there that are hiring people on contract as opposed to full time just because they don't want to pay their benefits, which is also unfair. It's only happening more and more and yet no one has any good answers for it yet.

Casey Elsass | Bushwick Kitchen

Casey Elsass, founder of Bushwick Kitchen, was always passionate about food. From picking herbs to play sous chef in his mother’s kitchen to making his own hot sauce as gifts for friends and family, if he can make something from scratch, he will.  

When approached by his friend Morgen a few years ago with an experimental idea to try and launch a business in only thirty days, he was intrigued but never intended on becoming a full time entrepreneur.

Heading into the third year of business while launching six new products, a custom line for Williams-Sonoma and a cookbook, we met recently to talk about everything from his early struggles to his profound respect for bees. 

“It’s important to me that we are aligning ourselves with producers that are taking this as seriously as we are.”

Let’s start at the beginning. Where did your passion for food come from?

I grew up in a family that loved to cook. We had a vegetable garden in the backyard. Some of my happiest childhood memories are being in the kitchen with my mom and her asking me to run out and grab some herbs or pull a carrot or pick a tomato… having that real connection to food. 

That’s a trickier thing to do in New York, I’ve learned over the years, but I’ve always liked the process of cooking, especially starting from scratch. If I can make my own ricotta, I will. Or making my own bread and making my own jams.

Enter Bees Knees. But, stepping back from the honey for a moment, what about launching a business in 30 days was appealing to you?

Morgen, who had the initial idea for the project, was moving to Europe and I was very happy at my job. We had a thought that if we could automate some of the business, maybe we could earn a little pocket change on the side but that of course didn’t work out. Four months in, I couldn’t keep up with the demand and by trying to just stay afloat, I was sacrificing so much at my day job that I had to quit. 

I didn’t go to business school and don’t have any sort of business background. I was working at the Metropolitan Opera and never fantasized about being an entrepreneur so I think my naiveté might’ve helped there because probably anyone would’ve said I made a bad decision by leaving my salaried, health-insured day job.  

But, when I hit that crossroads, I thought, “I don’t have kids, I don’t have a mortgage, when else in my life am I going to make that sort of reckless decision?” To just walk away from a very comfortable life to go and do something that half-thrilled me and half-terrified me at the same time turned out to be the right decision.

In those first 10 months, we did $170,000 in revenue and that first December, we’d sold 9,500 bottles.

I do think a big part of starting a business is that you need to listen to your intuition. I think that’s a common thread that most entrepreneurs have with one another. To the outside world it might not look like the right decision but we see that potential.

So talk to me about 30 days – the idea of starting a company rather than starting a company.  

Yeah it was kind of meta. (Laughs)

But then you really did start a company! The idea was an experiment but your passion is what kept you invested. You are the cook and the creative; during hard times, how were you inspired to keep going, can you define that?  

I should be clear, it was a long road from our $5,000 investment to the $170,000 in revenue. Most of that road was dark and terrible and grueling and without sleep with a sore back; all of those things that come with starting a business.

But I’ve always been someone who was very decisive. Once I’ve decided on something there is nothing turning me back from that decision. I think in my head, just in those early months, in that early response that we got, I felt something.

As soon as I made the decision, the idea of what it could be became so alluring to me, that even when I was hauling honey, I could see what this could eventually become.

Inevitably we romanticize that early hardship.  

Well, I should also say, I can just now barely start romanticizing it. It was so traumatic that first year. Especially that first Christmas, for months and months after I couldn’t even talk about it. It was so terrible but I do think you have to go through that and it gives me appreciation for everything we achieved because I really put every particle of myself into achieving it.  

No free passes, I did this with my blood, sweat and tears and I can be proud of that.  

What are some of the other struggles you’ve had over time and how have you overcome them?  

Well, we’re about to celebrate two years of being a business and we’ve made it this far without taking a credit card, a loan or any outside investors. And we’ve been able to because the business was profitable almost immediately. However, that came at an enormous sacrifice, including me prioritizing many things over giving myself a salary.  

Up until this month, I’ve been living on just enough to pay my rent, my student loan, my phone bill and a very small stipend for food. It was important to me to build this way and we were able to move into a new space and launch two new products purely through a self-funded business.  

Now, going into this year, my wonderful production assistant is now finally full time, my newer partner out in San Francisco is handling wholesale, we’ve added a few additional employees and we’re launching 6 new products still just on that self-funded account.  

A dark day was when that self-funded account, fairly recently, literally got down to $250 two days before the rent was due. It was scary, heart stopping and one of those moments when you understand why people scramble for funding. But then, the pendulum swung back and we had $50,000 in the bank.

That’s been the trickiest thing to figure out is how to balance a bank account while you’re trying to expand but you’re also figuring out when your retailers are actually going to get around to paying their checks. Are we spacing out when we’re buying bottles and raw materials correctly? Now I’m learning to not do big orders near the end of the month because that’s when rents and salaries are due.

The money is ephemeral and it flows in and out so a big goal for this year is to try and maintain an even chunk at all times. We want to look at $40,000 as our zero this year. If we try to stay above that and maintain our emergency fund, instead of walking on a high-line without a net, we’ll be covered in case of… well, who knows what happens? A product recall, God forbid, or sickness if one of us needs a replacement. Just the idea of having it in place ourselves for those emergencies that hopefully won’t happen.

Tell me more about the early days, how did you land on Bees Knees and what was the process like of developing the first product?  

Probably the greatest piece of advice I have maybe ever gotten in my life was from one of our friends, a really brilliant designer who has worked with a lot of app companies, etc. He said, “just simplify.” Don’t do two products if you can just do one.

In retrospect, that was totally correct because one product was journey enough.  There were some spicy honeys out there before we launched but no clear leaders in the category.  

We wanted to bring in a honey that was really well defined and really thoughtful in its ingredients. And again, it was an experiment but one that we took seriously so we sought the best in the Hudson Valley for our honey.

We’ve been with the same supplier from the very start, Honeybrook Farms in Pine Bush, NY, and they are incredible. It’s a husband and wife team with their daughter and their daughter’s boyfriend and they are so deeply responsible with how they take care of their bees.

I’ve gone up to help Todd, the husband, build hives and they live in this crazy field of wildflowers that used to be an orchard. Their full radius is mountains so they don’t hit any pesticides or herbicides and they don’t use sugar water. He’ll sacrifice his yield if it means the bees don’t have enough honey…all of these things that are contributing to the demise of the honey bee’s health, they just don’t participate in that.  

And, to be honest, it’s at a great cost to us. We pay a lot for that honey, but it’s just not something I’m willing to compromise on.

People that know honey and taste ours can tell its something really special. Even looking at the number of our colonies, the national average for colonies last year was 50 – 60% drop-off and ours was only 5% drop-off.

It was important to me that we were aligning ourselves with people doing things right; the same with our maple syrup provider. They are a multi-generational business made up of a father and son that run it up in the Catskills. Their family were early settlers to the area and started out as tanners then moved into the maple syrup business. We have centuries and centuries of knowledge of maple syrup going into each bottle by working with them.

It’s really important to me that we are aligning ourselves with producers that are taking this as seriously as we are.

How has that affected your price point?

It’s been tough. We are a high-priced product. I think e-commerce is a very different thing and people are willing to spend a little bit more online. At retail, we’ve done incredibly well, we’re already in 500 locations and we’re only two years old.  

But certainly if we had a cheaper product, we could have had conversations with national grocery chains sooner than we are now.  

We don’t make a huge margin on the honey or the syrup and that’s why it was important to launch the Weak Knees. It’s still got great ingredients but a lot cheaper so we can get a higher margin and make up the difference that we’re not getting on the honey and the syrup.

I’m sure that our price point slowed what could’ve been an explosive first year of retail to a really great second year but delaying that success for one year because we chose to have better honey is fine by me.

Also, you’ve built brand equity. You’ve instilled the premium nature of your product in people’s minds. The market responds to local and quality and history.  

Well the allure of national distribution is thrilling but are we going to buy some boiled, filtered, mass-produced honey just to meet the price point of a grocery store? Absolutely not! No, thank you.  

We’ve never tried to make this an urban product. We are Bushwick Kitchen and we operate in Brooklyn but our ties are really upstate with our producers.

It’s something that I’m just starting to appreciate now that I have more time to think about it but I think telling a story can do more for your company than having a great sale price. That does more in the customer mind than a price point.

You have a real passion for honey. Do you think you found your calling?  

My favorite day by far was the first time I built beehives. I’d never worked with bees before and it changed my life and my perspective so much. It is absolutely the most meditative thing. Collecting honey can be a little treacherous but building the hives is incredible.

The bees come in these crates and the queens come in these little boxes with a sugar cube at the tip of it. You build their hive and you put all their frames in then you take a box of bees and pop the top off. They are so psyched to get out of that box and you dump them into their hive. They are such funny creatures because they are just programmed to work. They get out and immediately start swarming the whole area.

Then, with the queen’s box, you poke a little hole in the sugar cube and the nurses start chewing their way through slowly so by the time the bees have gotten through, the hive is used to the queen’s pheromones and recognize her as the queen.   

The process of creating a hive is absolutely a set in stone, multi-step process with no shortcuts and no going out of order. As the human element of building these hives, you kind of lose yourself in it because there is no thinking about it. You do this part then you do this part and you do this part and so on.

The sound of all the bees buzzing around you becomes melodic. You start hearing the variances in their flight patterns or in their movements and the bees in the hives starting sounding different than the ones flying around you. I felt so lucky to be able to do that and have that relationship with my supplier where I was invited to do that and those hives were only for us.

From the hive directly into our bottles, having that was really special. That’s the kind of stuff that no matter how big the business gets I’ll always be able to do. That’s what I enjoy.  

Besides the ingredients, what do people love about your product?

I think, actually I know, because we’ve gotten this feedback over and over, the packaging design really won people over for us. We owe so much of our success to having a really well thought out and well designed bottle. Ras is a friend, a great friend and will hopefully always be our designer. He just envisioned a really clean, beautiful looking honey product that doesn’t look like – you know the honey bear or those really opaque squeeze bottle things. I think that helped a lot but of course our customers wouldn’t come back if they didn’t enjoy what was inside too.  

Quality packaging and ingredients are a great start. From a marketing perspective, what are some things you have found effective to raise awareness of the brand? Did you have a plan going in?  

Our first year was I would say, 90% press driven.  

That was also me with a lot of hard work and pitching. And it was ultimately a numbers game. I pitched 70 publications for gifts guides and we ended up in 3. Granted, great outlets - Vanity Fair, Esquire and Bon Appétit - but that was a roll of a dice. And two weeks before Christmas, we were on The Today Show but that was 5 emails to a producer into the abyss and her first words when she finally called me were, “you are quite persistent.”

And then it turned out we got almost no press in the second year, a huge swing in the opposite direction.

Our margin is so much better in e-commerce over wholesale. We have to ask ourselves: How do we catch a customer? How do we contain a customer? How do we make sure we are catching more customers?  

We wanted to embrace education and entice people to find ways to use it all day everyday through beautiful imagery and recipes. We also started with Facebook ads, then trying trailing ads. Investing a little bit more money in these basic forms of advertising, the ROI has been great.

Any one thing that gave you the best return?  

Probably the trailing ads, I’m interested to watch that progress. We’re only five or six months into it so I’m interested to see if it works out in the long term. The click through rate leading into holidays was great, that was without any discount, purely an ad so that was incredible.  

You seem to have your process down and put so much of yourself into the business, why bring on a partner?

Ted came in as Morgen was planning his exit. He’s awesome and, unlike me, he did go to business school, which is nice. As much ownership as I feel over the business because I started it and physically make the products, it is so welcome to me to have someone I view as an equal to collaborate with. 

Some people love flying solo but I think it’s very important to have that other set of eyes, or brain or an ear to talk to that you can really lean on. I appreciate my time with Ted so much; he’s a really great partner.  

Anything that keeps you up at night now; times you want to throw in the towel?

The things that keep me up at night are all the really small little things that I forgot to do. Its never big picture, I feel enormously confident in the direction of the brand we’ve built in two years. Its more like did I remember to turn the honey machine off to tell Nicole not to do that thing or did I include that customer’s note in the box that they’d ask for…I’ve been able to relax and have confidence in the business so now it’s the naggy things versus big.

That first year, I was alone in a commercial kitchen at 2:00 AM and miserable thinking of hauling and shipping and sure, the thought of throwing in the towel crossed my mind, but there has never been a moment where I seriously considered doing something else. I absolutely would not go back to a desk job and work for someone else.

What’s your vision for the future?

Coming into our third year, we’re starting to think, what are the next 5 years going to look like and starting to make branding decisions that work towards that.  

We feel it’s important that while we’re gaining steam with retailers, we expand horizontally on their shelves, launching products under the Bees Knees, Trees Knees and Weak Knees lines, where each name starts to be become synonymous with honey, syrup and hot sauce sections. 

Then, after this year, we’ll start moving away from that and start exploring other ideas that aren’t necessarily condiments but still fall into food. All still things that can be found in the grocery aisles but we’ve got plenty of ideas that aren’t limited to a squeeze bottle.

OK last two questions, any mentors?

Does it sound egotistical to say no? No, not really. I don’t know if this is good or bad but this is just my way. I sort of insulate myself from the business world and the food world.

For me, at least, the most deadly thing is comparison so I try to avoid that at all costs. For me, its better to just see what’s going on right in front of me. I don’t get too much into the philosophy of things; I’m a pretty straightforward type of person.  

Ted and I talk about something, workshop it and then if it gets to a good place, we try it. Sometimes it works, sometimes it doesn’t then we adjust from there.

Finally, any advice for others?

I can’t give universal advice about starting a business but I would say that it’s great to have a great idea and great to be excited about that idea but you need to understand what you’re going to be sacrificing.

If that doesn’t scare you then yeah, go for it. If you are ok giving up your social life, giving up an income, giving up a full night’s sleep and giving up your weekends then, absolutely, do it, why not?

There’s never going to be an ideal time. Don’t wait for two years to save up paychecks, just do it right now.

Insights From The Bootstrappers So Far: The Long Game

It’s been a couple months since I launched By The Bootstraps, and it’s been a great reception (thank you!).  I thought I’d take a day to reflect on what I’ve learned since launching the project.  Although there are many insights, today I want to focus on just one – The Long Game.

The Long Game is a phrase you often hear used in business meetings, and when used casually, it can lose its meaning.  But if you really consider the true meaning of "the long game", to me it means this – "I have discovered what I’m passionate about and I’m going to commit to it, good or bad, for the unforeseeable future because I care about it that much."

Whether it was Brian Smith nearly losing his mind as he studied to become a sommelier, Scott Lapatine, who still routinely works till 1am, not because he has to, but because he wants to, or Kerry Diamond, who distributed her print magazine by hand to stores to get her project launched, everyone I’ve spoken to cares so deeply about what they’re doing that they do the things most folks wouldn’t dare do, in order to win in the long term.

And that’s just cool.  And inspiring.  What I love most about the people I’ve spoken with to date is that they are all brave souls, with unique approaches, but united by the fact that they are willing to risk failure for the thing that brings them the most joy.

There is a lot more to uncover, and I’m looking forward to the conversations that unfold in the coming weeks and months with new entrepreneurs. 

A big thanks to those who have participated to date and a reminder to sign up for the newsletter to receive the latest from By The Bootstraps and Phear Creative. 

Kerry Diamond | Cherry Bombe

Kerry Diamond has been a fan of journalism since she started her own newspaper in the third grade. After years of success in the beauty and fashion editorial space, she tapped into a latent passion for food and along with her partner, Chef Rob Newton, Kerry helped create the Brooklyn restaurants Wilma Jean, Nightingale 9 and Smith Canteen.

She also, with co-founder Claudia Wu, launched Cherry Bombe, an annual magazine that is a sort of love letter to both food and girl power. 

Currently serving as the Editor in Chief of Yahoo Food, Kerry talked to me last week about being an entrepreneur, intra-preneurism within larger organizations and the joys of lugging boxes of magazines around our shared neighborhood of Carroll Gardens.

“If I’d thought too hard about any of this stuff, I never would’ve done it.”

You and I have been in this neighborhood for about ten years.  A lot has changed since then.

I recently re-read the first book in the Little House on the Prairie series. They were churning their own butter, making their own bread, building their own furniture, and my first thought was, “Oh my god, it’s Brooklyn” (Laughs).

But seriously, it’s not just Brooklyn. It’s a really exciting time to be a maker, a do-er, an entrepreneur right now. This thing, this movement, is happening everywhere.

Where else are you seeing it, and why do you think it’s happening?

Rob is Southern and a chef, so we’ve spend a fair amount of time on the road going to different food events. We’ve stopped in a lot of these secondary and tertiary cities, places like Little Rock and Memphis and Birmingham, and people are re-claiming these abandoned downtowns and opening businesses, breathing life back into these places. There’s more opportunity in these cities than in a place like New York, where it’s so expensive and difficult. A lot of these new businesses we’ve seen happen to be food related.  

Why do you think that is?  Why is food playing such a big role in these cities?

Number one, food is easier to get into than other categories, relatively. If you want to make, say, handbags, it takes a lot of time, expensive materials, and a lot of skill to get to a finished product. On the other hand, if you want to make, say, vegan baked goods, you can do that by yourself at a low cost of entry and sell at a local market or pop-up. In that way, food is easier than other fields. It doesn’t take an army, it just takes time and dedication and a tasty product. Also, everyone eats.

And then you have millennials, who are changing everything. There was this fascinating research that said 50% of all college graduates today identify themselves as foodies. That wasn’t even a word that existed when you and I were coming of age. So they care about and think about food in a way that my generation didn’t.

How else are millennials changing food?

Young people aren’t interested in old school, unhealthy products anymore, and the big consumer packaged goods companies are responding by bringing out healthier products. Things like big soda are taking a beating.

The research also says millennials don’t want to buy as much stuff as previous generations. That whole sharing economy of Uber and Airbnb is make us rethink things that meant so much to us previously—“I’m going to grow up and have a car” or “I’m going to grow up and own a home.” But one thing people will always need is food.

Part of this blog is about where innovation comes from; I want to believe that a lot of it comes from people who are doing it on their own. But you’ve worked for larger companies while still running your own businesses separately.

It doesn’t matter if you work on your own or you work for a big company. Innovation always starts with one person with a good idea. You just need to be brave enough or crazy enough to share your idea or bring it to life. Some big companies don’t want individuals who think like entrepreneurs, but some really embrace those kinds of people. Not every idea I lobbied for or executed turned out great or was given the green light. One of my bosses, Glenda Bailey at Harper’s Bazaar, gave me the best piece of advice I ever received. She said, “Don’t bring me problems. Bring me solutions.” So if one of my maybe-not-so-brilliant ideas wasn’t working, I would go to my boss and own up. But I always had a backup idea! It’s good to operate that way if you work for yourself or someone else.

Let’s talk about Kickstarter; I haven’t interviewed anyone that’s gone that route yet. Why did you decide to go that route?

I’d rather cut my own arm off than ask someone for money. Some people are fine asking for money but I’m just not that way. Getting investors comes with certain obligations. You have to be comfortable with people telling you what to do. I still haven’t taken any outside money for my projects. Maybe one day. I didn’t feel bad about taking people’s money through Kickstarter because I knew they would get something in return.

 So what was the inspiration for Cherry Bombe initially?

When Rob and I opened our first restaurant, I realized pretty quickly I had no mentors or support system in the food world. I had a pretty long career in beauty and fashion with a lot of mentors and mentees, but in food I didn’t. At the same time, I thought, “Where are all the girls?” There were no female chefs or restaurant owners in my neighborhood at that time. Now there are some, Zahra Tangorra at Brucie, Alex Raij at La Vara, our sous chef Morgan Jarrett, but it’s still mostly guys, especially in Carroll Gardens.

It was a crazy venture to launch a print magazine. When I look back, I’m like, “What were we thinking?” We’re just super fortunate that not only did we find an audience with Cherry Bombe, but our timing happened to be pretty good because there was this thing simmering under the surface of the food world among women. Resentment maybe? (Laughs)

Women were just tired of being passed over and left out of the conversation. Cherry Bombe has helped shift the conversation a bit and put a spotlight on some amazing women in this industry who are doing great things.

What do you see as the future?

I’m not sure! I do know the universe will push you towards things that you weren’t anticipating. You have to be open-minded enough to accept those things. I never thought I’d have a magazine or restaurants. I definitely would like to do something in the social enterprise area. Every business should be a social enterprise. Create jobs, make people’s lives better, make good products people actually need. Why not?

With all the challenges and hard work running your own thing entails, why do it?  What makes it worthwhile?

Good question. There’s a ton of hard work you don’t anticipate. The schlepping of boxes filled with magazines; the working 24 hours a day. Most entrepreneurs are pretty driven people. They have an idea that means so much to them, they’re willing to put in all that time, risk their finances, etc. But most people have to work hard regardless of what they do. If you can do something you love that makes a tiny difference in people’s lives, you’re lucky.

What were some of the things that helped you get momentum?  Did social media play a role?

Social media is such a blessing for a small business. It makes it so much easier to get the word out and to find an audience. It’s definitely contributed to how many new small projects and enterprises we’re seeing around the country, don’t you think? Our Kickstarter campaign was a big help for Cherry Bombe. We got huge momentum from that. As for the restaurants, media in general was extremely helpful in terms of momentum. We always received a lot of nice press for each location that we opened and that is so critical in a place like New York City. It’s easier to open your doors when people already know about you and get what you’re trying to do.

Was it a learned process for you, or did it come naturally?  

I took to social media pretty naturally. I remember years ago when I worked at Lancôme and I put the brand on Facebook before any luxury beauty brand was on there. I got in big trouble for doing that. Things are very different today.

I like doing social media for my different businesses, but it is a time suck. If you’re successful enough to have your own social media person, I envy you!

What have been some of the big milestones for you?

I’m a big Francophile so seeing the magazine at the Colette boutique in Paris was a big deal for me. 

Honestly though… everything has been a milestone. It’s a miracle to put something out into the world and find an audience. Cherry Bombe has been mentioned in a few New York Times stories. Knowing we’re part of the bigger cultural conversation and that people take us seriously means a lot. Someone told me that Smith Canteen, our coffee shop, was the center of her universe. I think she was half joking, but still. That made my year. And just any time someone walks through the door of one of our restaurants, I consider that a milestone. You have a lot of choice in New York, especially when it comes to eating out.

Anything that you haven’t achieved that you’re hoping for?

A day off! (Laughs)

Anything you’d like to see happen in the upcoming election that would benefit small business owners?

I’d love for one of the candidates I’m rooting for to propose a flat tax for businesses. The tax system is so complicated I can’t wrap my head around it. As a small businessperson, you have no choice but to hire bookkeepers and accountants and muddle your way through it if you don’t have a finance or business background, which I don’t. It’s almost impossible to do it on your own.

I don’t mind paying taxes. But I want to see something good happen with that tax money—good schools, the unfortunate being taken care of… I want a candidate focused on the right things, not just making the rich richer.

The system today favors corporations, not small businesses. We’re the backbone of all these communities. It would be awesome to have all of our elected officials be super pro-small business and talk them up all the time. Can you imagine?

Brian Smith | Loca Linda & Club W

Brian Smith is an affable guy whose easy demeanor belies a character full of conviction and passion.  He has a fierce independent streak and as a serial entrepreneur, Brian’s ideas have taken him from professional snowboarder, to sommelier at one of the finest restaurants in the country, to wine maker (Loca Linda), and now, tech entrepreneur (Club W/WINC).   

I met Brian ten years ago through mutual friends and he and I have kept in touch ever since, often exchanging bootstrapping war stories.  Now based in California, I sat down with him when he was recently in New York to talk about the grit it takes to make it and his passion for wine and the people who drink it.

“You can never fully master wine.  If you tasted it two years ago and open a new bottle today, it will evolve over times. And at the same time, there’s someone in a garage working with an obscure grape that will change everything. You can spend your whole life exploring and tasting wine but you can never really master all of it. That was exciting to me.”


You started as a professional snowboarder, tell me that story.   

It was kind of a lifestyle job. I’ve always been into lifestyle jobs. (Laughs)

It was much different than it is today. Being sponsored, you’d get very little money but you got paid to travel around and shoot different photos and videos and basically couch surf the entire winter.  Somehow, I was able to finish college before I did that but snowboarding was really what I dedicated my life to for several years.  

But as I continued, I got more interested in personal challenges than filming and taking photos and playing that sponsor game and as a result the sponsors weren’t around as much anymore to support me.

So how did you move from snowboarding to wine? Was there a linear path or did you experience a particular calling?

It was really by chance. After my snowboarding sponsorships dried up, I needed a way to pay for my lift pass and found that through a local liquor store.  I could work there nights but still spend days snowboarding as my passion so it was the perfect way just to maintain my lifestyle.

Back then I was a Pabst Blue Ribbon or Crown-drinking guy and I didn’t know anything about wine.  I maybe drank some to try and impress a girl but I was basically clueless. So in the downtime of the shop, I’d sit around reading wine magazines. I had absorbed a little but not enough to answer customers wanting to know the difference between a $14 bottle and a $150 bottle.  So I read more just because I wanted to be able to answer their questions.

The more I read, the more I wanted to taste and that research became this vicious, passion-driven cycle.

For example, early on I learned that to find great wine in Bordeaux you have to be within a certain distance from a river.  If you can see the river from the vineyard it’s gonna be a better Cabernet.  I remember thinking that wine had all these great things about it, it’s geographically diverse, it’s historically and culturally rich – there’s so much behind every bottle of wine.

And how did light reading for your retail job turn into you wanting to be a Master Sommelier?

I remember reading about a sommelier. Someone who could hold a glass of wine, look at it, smell it, taste it and tell you where it came from in the world, what the vintage was like, how old it was, how it was made, what the grapes were…. that was amazing to me.   After reading about wine, being asked questions I couldn’t answer at the store, taking a trip to Napa, I knew this is what I wanted to do.

So what were the first steps you took on that path?

Well, I got super fired up after learning that being a sommelier was actually a job so I got back from Napa and set up my first tasting group in Jackson Hole. TWR: Teton Wine Research. We got a really diverse group of people, some collectors, some restaurateurs, some ski bums and held monthly tastings.

I was also studying for my sommelier exam so I set up a study group for that. I even convinced the local paper to give me a weekly column (laughs). Basically, I did everything I possibly could to learn about wine so that I could answer any question I was asked while also getting other people excited about wine whenever possible.

My goal was to be a master sommelier and instead of partying every night with my friends, I would be studying and drawing maps.  It ended up totally taking my life over.

So you pursued your master sommelier license, was there a degree? How does it work?  

It’s all self-study but there is a community of mentors, some great people that can help you to accelerate your learning.

There are four tests to get to the master level.  Pre-certificate, certificate, advanced sommelier (which I am) then the masters, which you can only take twice a year and is invite only.

At some point I decided to quit my job in Jackson Hole and I drove to Vegas and volunteered in restaurants around Vegas learning.  That’s how I ended up getting a job at Aureole – one of the best jobs in the country, as a sommelier.

For anyone that’s interested, there is a great film called Somm that is worth watching. It follows people losing their minds as they go for the master test. 

Were you losing your mind?

If you ask my wife, she’d tell you I was crazy.  I basically wrote my own wine book that I still have today, the big black binder of wine. 

I would orally record details of different regions and then listen to those tapes in the car and before bed.  I would hand draw maps and then post them all over the house, studying them when I took a shower. It was sick, twisted stuff.

You became a sommelier and then moved to Vegas to work in the fine dining scene – when did you get the courage to start Local Linda?

Well, there was nowhere to go in Vegas - Vegas is owned, and there’s very little entrepreneurship - so I took a break from wine and worked in finance in the Virgin Islands for a while, which worked out, but after a while I missed the States and wanted to get back into wine and found some buddies with whom I started a very high end wine bar called Clo.

It was a very ambitious project that was ahead of its time, and we got stuck waiting for permits for the wine bar. I started going crazy again, so I took a trip to Argentina and as soon as I got there I fell in love with the place. 

I wasn’t really thinking about making wine, but a friend invited me to Argentina.  I went down and as soon as I got down there I fell in love with the place.  It was like Jackson, but instead of the Tetons you had the Andes, and at the foot of the Andes were the vineyards.  And I was taken.

And I learned that they had really old vines – which are not usually available to someone without money.  Also, there was a lot of sharing of tank resources, because capital is hard to get down there, so everyone there was trying to help each other out.  On top of that, it was a strong US dollar.  So all these things kind of came together and I realized, “This is my shot.  I’m never gonna have the pearly gates opportunity.  I’m never gonna be in Napa – I don’t come from that family.” But I knew that I could be everything.  I knew the market, I knew the wines and the vineyards, I had a footprint in NYC, and I thought I could make something that might resonate with people.  Something that would be different, something that I would want to buy, or my friends would.  So I thought I’d go for it.

Any rough times in the early days? Dark nights of the soul?  

Well my wife is also an entrepreneur and we were kind of in a similar situation where we were both getting off the ground. I worked out of a closet / office in our house, we called it the “cloffice”.

It was five months before we were having our first kid, Loca Linda was going but not really bringing in anything and yeah, it was hard. But, I just kept cranking, really cranking locally while trying to open new markets.

It was scary as hell but I believed in it.  I believed in willing it to succeed and ultimately, it did. 

I remember talking to a distributor who just didn’t get it.  And I remember feeling great, telling this high level executive, “I know in my heart that this is going to happen and you can either be a part of it or not.”

When did you feel it clicked?

I took every opportunity to sponsor and connect locally at events and at tastings.  But I remember walking in my neighborhood in Brooklyn and seeing 4 empty bottles in a recycling bag on a curb and I was like, “YEAH, someone is getting after it.” That was great.

The other thing was trying to go after the most discerning sommeliers to get them to pour by the glass while also being approachable for people to consume at home.  We were adopted by sommeliers and restaurants that normally wouldn’t serve our wine, and that really informed our momentum.  We sell it for $16/liter in the store, and Thomas Keller sells it at $16/glass in Bouchon.  That’s really cool.

Those things are great from an ego and validation perspective and they really help build momentum for your product.

Greatest reward?

Producing something that people touch, interact with or consume and that are enjoyed around great times in their life…. there is something really special and intimate about that between you, the maker of the product, and the consumer.  

What opportunities came from Loca Linda, how did Club W come about?  

Club W came about when my sommelier buddies introduced me to these really smart people that had some great ideas but maybe didn’t know as much about the wine side. The “directy-ness “ of their idea was super fascinating to me.

It was a culmination of all of my experiences. I’d served wine as a sommelier, sold wine as a wholesaler, I’d imported wine and I’d made wine internationally. I had a 360 view of how things worked and what could be done in a space that was stagnant and it was a perfect fit for helping them find a better way to buy wine.

I became a co-founder 3 ½ years ago. I’d always been a lone wolf so being a part of a dynamic team, the mission, the culture… Loca Linda was just a grind trying to convert palates on the reg. But these are great partners that I’m lucky to have, pushing each other, pushing our teams, it’s something I’ve never done but I find it really fascinating!

Our shared goal is to change the landscape and make it better for wine drinkers.

Lessons learned with Club W?

We’re learning so much because we have this constant feedback loop of so many customers.  And looking at data versus to just face-to-face, we have these new insights that you wouldn’t expect and is contrary to current trends/ what the market would expect.

For example, most people think that you can’t sell a Syrah unless it’s French.  But our California Syrahs sell really well.

Everyone says Chardonnay is the Queen of whites.  We sell very little.  And that’s contrary to Nielsen data, which is interesting.  And people like Merlot.  They don’t know it, but they do.

What are the big opportunities in the wine market?

There’s an access problem for people that don’t live in major markets.  Outside of major cities, all the wines available are made by about four or five different wine companies.  You may see 50 or 60 labels/SKUs in the store, but they’re all made by the same companies.  Because distribution is pretty locked up.

The way alcoholic beverages are sold is really the same as it was right after prohibition.  It’s a push model.  Suppliers push wine to their distributors, and distributors push it to retail, and retail pushes it to their consumers.  The business is so big with these big guys that there’s a lot of pressure to deliver on sales and that trickles down the market.  And I think that for the consumer’s sake we need to move toward more of a pull model.

And on the flip side, some of the most exciting things that are happening in wine are happening on a much smaller scale.  The people with the least resources are doing the most interesting things.

But because they don’t have the resources to compete with that big push function that’s happening, that’s hard.  Replacing push with pull, that’s a big picture thing that’s really interesting to me.

What’s the future for Club W?

Club W is a huge undertaking with a huge amount of risk.  Are we going to do it? We said, “Fuck it, let’s go.”  By creating our own wine, we’ve ripped everything up and we’ve developed these core competencies that we never envisioned when we set up the company.  We think there is value in the product we are building and we just want to remain super curious. Initiate, innovate and continue to delight our customers.

Any advice for other entrepreneurs looking to start up their own business?  

Don’t! Just kidding. I feel like everyone’s an entrepreneur now, you kind of have to be.  If you’re not cut out to work for someone else, start your own thing.  It’s all about diligence.  It takes a lot of work and a lot of planning, but it starts with an interest, it turns into a passion, and then you follow that down and that becomes your story, that becomes part of your brand, it’s really the origin story.

Do something where you can truly be an evangelist, and so much so where you turn other people into evangelists.

Never take no for an answer.  CHISEL!

Combining a long view while rewarding yourselves in the small victories of the day-to-day leads to less stress.  I mean, I don’t do it, I freak out but I have to remind myself that its just today’s disaster, it’s not the end. 

Scott Lapatine | Stereogum

Scott Lapatine has loved music since he can remember.  In fact, listening to music is such a fundamental part of his being there isn’t a moment in Scott’s day that goes un-soundtracked (he has speakers in his tub for when he’s giving his daughter a bath). A devout student of music writing, Scott developed his chops as an intern at MTV when he was in college, and he took subsequent writing posts on the .com team at MTVi and VH1.com.

In early 2002, he started Stereogum as a hobby to champion bands he liked – everything from pop to the ultra obscure. Now, 13 years later, a husband and father, his passion for music has only become larger and Stereogum has blossomed into a deeply engaged music community of millions of fans a month.

Scott and I caught up a few weeks ago and he shared his candid thoughts about the rapidly shifting music and publishing industries, as well as what Phil Collins songs he thinks are truly essential.

“You should be sound tracking every minute of your life.”

How did Stereogum start?  

In the beginning of 2002, I started Stereogum as a hobby. We didn’t call it blogging back then, it was LiveJournaling or an “online diary” - though I would never say “online diary.”

Going out to shows, reviewing music, posting music gossip… It was anonymous for a few years before I put my name on it, but I was just trying to distribute mp3s of bands I thought weren’t getting enough attention.  

I was working at MTVi, specifically for VH1.com, at the time and I was giving 110% at my job but me working on Stereogum simultaneously was the worst kept secret at the company. I think it helped inform my work at Vh1 so it was OK - I created MTV Networks’ first blog, made their first ringtone… On-air, I’d have them throw to this extra online content. Back then, that was something new.

The time was right for blogs and small publishers to get more attention and I was starting to get some feedback that I could make some money through a third party blog ads company.  

I was essentially working two full-time jobs for a few years at that point and was desperate for someone else to take it over, really burning the candle at both ends and working until midnight or 1am. No one wanted to acquire it without me staying on.

How did you make the jump? 

I met with a few venture capitalists and flew out to San Francisco for another meeting with a company interested in the blog. I was about to sell Stereogum when I got a call from Jason Hirschhorn from MTV who introduced me to Bob Pittman, one of the founders of MTV. They believed in the site and wanted to invest.

I left VH1 in April and by the fall of 2006, I was incorporated and hiring a small staff. 

What were those early days like? Were you scared?

I went from being a producer at VH1 to being the CEO of Stereogum. I was a CEO of something?

I had to learn about KPIs, making sure my investors were getting something in return and I had to learn a lot about content and how it worked.  

When I have to fill out forms where they ask my job, to this day, I list a different one every time. I’m an editor, producer, music critic, blogger (though that doesn’t sound very cool)… it’s a little bit of everything. 

Now that it’s your work, do you still love music as much as you did as a kid? 

I was a kid who would spend a hundred hours making a mixtape.  

My closest friends all stopped really listening to music 20 years ago, but the internet has afforded me this opportunity to reach other fans. I’ve also been able to hire people to keep me informed, maybe I’ve been lucky, but they’ve all been really great. 

How do you hire? How do you ensure your voice and vision stay enact both in the past and now?

I hired a sales person and a writer and one operations guy and for many years, through 2010/2011, it was that small an operation.  

The first writer I hired (editor’s note: Amrit Singh, now a filmmaker and on-air host on Revolt TV) was a lawyer and emailed me a review he’d written and it was solid. He also took really great photos and would even record parts of the show to make sure he could go back and figure out the set list. I’ve actually met a lot of my writers by them emailing me their work.

I have two senior writers in Virginia and Ohio. But in being remote, they don’t waste time commuting. And news is such a big part of our business now. My hours are 7am to 1am every day.  It’s an insane workload but I love it. 

Some entrepreneurs want to pass it over to a staff but it seems like you want to keep it yourself. 

Some people might call it micro-managing (laughs). But yes, I like the details. My staff could totally handle it, but I enjoy being involved as much as I can.

How do you consume information? 

There was something on a Buzzfeed writer’s Twitter a little while ago, people comparing their numbers of unread emails. I have over a half a million unread emails right now.

I’ve kept the same email address since early on so I get a lot… Pitches from publicists, pitches from bands, newsletters, it’s a lot to sort through but I have my filters.

If I was starting a music publication now, it would probably just be a playlist or an Instagram account.  Between the dominance of Facebook and ad blocking on mobile, it’s rough out there on small publishers. 

We’re small so we can be nimble as publishing changes but the blog format can seem archaic. 

So no blog/site? Great, because that’s what I’m launching with By The Bootstraps! (Laughs)

It depends what your goals are. It’s difficult because young people may not use RSS but they are on Instagram or Snapchat… but right now those are not going to drive any traffic to a website that has advertisements on it. Banner ads are certainly starting to go away.  

There is a revolution happening in both publishing in music. I’m happy to be writing about as well as observing it rather than working at a record label though.  

Speaking of the music industry, where do you think it’s headed? What does a band have to do now to succeed?

Well, we started as an mp3 blog but labels don’t even put them out anymore.  It’s all streaming. 

Touring, merch, and syncs are how they make money and I think the most successful ones are those that engage with their audience every day and take fans on their journey. 

Maybe that doesn’t turn them into superstars but whether it’s a patron model or fans are paying for exclusive content, they need to make that connection.  

I think smaller bands can get more notoriety than in the past because of the big audience online. There is a huge opportunity there. It’s an exciting time and there’s more than one right way to do it.  

From the publishing end, any thoughts on what the future is there? Clickbait for all? 

I feel very passionate about this.  Any decent online publisher is going to get accused of doing clickbait now, the way it is too broadly defined.

Stereogum has very high standards of what and how we share. Most people come to us from social. You see a lot of publishers there exploiting the curiosity gap -- “Kanye attended this awards show, you’ll never guess what happened next.” I’m not going to trick someone into clicking on a Grimes mp3! 

I write all the headlines - maybe that’s why I don’t get any sleep - but it’s because I want people to know what they’re getting when they come to us. 

We also have internal discussions about anything we think may not be right for Stereogum. There are a lot of things I can do to increase traffic, some unscrupulous things or just things that would be lame that would be good for traffic.  

I also don’t make my writing team look at traffic at all. My managing editor and I are aware of traffic but my writers just have to write, listen to music and be critics.  We don’t have a social media person, we all sort of do that. (Talk to me in a year and we might.)

It’s really interesting right now because it’s so competitive. You have a small window to get someone to click on your link before someone else’s. You just have to cross your fingers and hope your message works on Facebook.  We’re not as dependent on Facebook as other sites are though which is good because no one really understands their algorithm.

We actually get a lot of traffic straight to our site; a lot of publishers don’t. Our traffic is higher than it’s ever been. If it wasn’t, I’d be worried and thinking that I should be doing something else. 

Also, a lot of big sites these days don’t have comments. We have a community of people who genuinely like to talk to one another about music. I moderate it, get in the comments and engage. It would be boring without any feedback. 

How do you do it differently? 

We don’t have traditional meetings. Meetings are a waste of time. We’re just going to blog. We weren’t going to have an office initially. We have an office now but we still have remote people. We also did things differently content wise. We don’t really have traditional reviews. Everything is sort of a review. We don’t give scores or grades. A news story may have some opinion in it. We do long form.

We’ve also maintained a certain aesthetic, an irreverence and a core interest in certain types of genres. A lot of music publications have expanded into movies and pop culture, that is not part of the plan and I don’t have interest in that. There is still so much we can do with music.  

We’re growing but we’re still a small operation. We compete with some of the big operations out there but they have ten times the number of people working for them so we really just have to hustle and focus. 

What do you love about your job? 

I have a 6 year old, so I don’t go to as many shows as I used to, but the excitement about discovering a new band has never gotten old for me.  You hear a song that you love and you play it on a loop, you find out when are they coming to town, when you can get the album…  How are we going to support them? 

I don’t have any hobbies outside of music. I would be doing this sort of stuff on some level even if this weren’t my job. Even going back to high school, I would always have music on.  We’d drive around and my friends would turn down the radio, like, ‘Can’t we talk?”

“No!, Why wouldn’t you want music on all the time?”

These days there are so many things that you can discover from reissues or things that you can find on streaming that you didn’t catch on to the first time around. It’s a great time. 

You mentioned inefficiencies and taste earlier, what differentiates Stereogum? 

We like to consider ourselves authoritative and irreverent but also interactive because we have comments. We get a lot of reader tips.  

We also cover everything.  The editorial intentions are very pure.

When I was starting Stereogum, there was a backlash against places like MTV and boomer music publications because there was a perception that the editorial was dishonest.  Was it driven by sales or cronies of the publisher?  I don’t socialize with bands or PR people, really. I go to work and then hang out with my family. If we endorse bands, it’s because we want to.  I think people sense that and know they can trust us. 

At the same time, Stereogum is a really small team. I haven’t taken a day off in 5 years and we work on holidays, but its ok because we’re passionate about it and I think people know that too. 

It’s also different in a business sense.  In so many other music publications, that’s just one sort of aspect of their business.  Maybe they have a print magazine or a festival or they do marketing, but for us, we’re just a website.  Again, that may change in the future but that’s where our focus is right now.  On one hand, we’re limited in what we offer, but that also allows us to make it the best it can be. 

Did you ever have any dark nights of the soul where you just wanted to throw in the towel? Either in the early days or even recently as you’ve grown?

Stereogum had a spinoff called Videogum for many years, a separate site and separate team dedicated to television, movies and online video.  It was supposed to be funny, astute commentary about prestige TV dramas, viral videos … live blogging of award shows.  People really loved it and the writers were great.  

The unfortunate thing was Videogum was never supported by SPINMedia. It was a small operation down to one person and then they axed that one person.  It was profitable and they shut it down very abruptly. 

By the way, it’s OK for me to say this now because there is no one at the company now that was there during that dark period.  

I’ve been with this company for 8 years, longer than almost anyone else there. 

What’s the vision for Stereogum? 

We’re reaching about 5M people per month now. We’re often first with news, early with our version of ‘reviews,’ but we were so late on a social network presence we don’t have the reach that some of our competitors have. There is a bigger audience out there for us and I’d like to grow the Stereogum community and empower the readers so that they’re contributing, have more of a voice and can share with each other.  

We’re just at the start. I’d love to do more events, it’d be very cool to do a Stereogum festival at some point. We’ve produced original albums over the years, comps of bands covering classic albums – the Strokes, Radiohead, etc. and I’d love to do more projects like that.

Any advice? 

I’ve been helped over the years by people who love what they’re doing and are so knowledgeable about music, I couldn’t do this by myself. I’d recommend surrounding yourself with intelligent people. 

Favorite Phil Collins songs? [It is his Twitter avatar: twitter.com/scottgum]

“I Don’t Care Anymore” or “Take Me Home.” He’s due for a reassessment, he doesn’t get enough respect these days.

Michael Williams | A Continuous Lean & Paul+Williams

As you walk through the offices of Paul + Williams, a narrow hallway opens up into one of the coolest showrooms of men’s clothing I’ve ever seen.  It’s been carefully developed over years, and is a reflection not only of Michael’s good taste, but his attunement to his own personal vision.  We sat in the back at a round table surrounded by racks of Patagonia gear, rows of Red Wing Boots and stacks of limited edition Levi’s.  The perfect backdrop for his story…

“Our philosophy with everything is no turnover. No turnover with our clients. No turnover with our staff.”

A little background…

Eight years ago Michael Williams and Ali Paul began Paul + Williams as a boutique PR agency.  Over time the agency has evolved, and their current client list now is comprised mostly of men’s fashion brands.  Despite the agency’s success, Michael is probably best known for his popular blog, A Continuous Lean, which features and examines style and some of the American-made products that Michael admires. He and Ali have developed a robust and focused business, and have become sought after for their sharp instincts and deep expertise by the media, his clients and his blogging audience.

This place is amazing.

Thanks.  It's kind of like a dream closet of mine.  

So, rewinding about eight years, why did you start?

I started because I didn't want to work for someone else.  I wanted to be the one who decided what was the best use of my time, and how I structured my day. 

There's that thing, on Sunday, if you have a job you hate, where you dread going into work. I had a job like that.  But if you do something that you really love, and if you work for yourself you never think like that.

When you started out, what were some of the bigger challenges? 

There were two things that were the most vexing. Number one is that there are no guidebooks to this. You just have to make the mistakes on your own.

Number two is good people. Without good people you can't scale. You can but it’s unsustainable.

Were your parents an influence on you?

I’m very much my father’s son.  He owned a bunch of businesses, and I remember in kindergarten I would have a half-day of school and the second half of the day I would ride around in the car with him as he visited his different businesses and took care of what he had to do.  I always saw how he worked, and I guess I’m very similar, and eventually I started my own businesses. 

Why did you think people would want to work with an agency like yours?

I think I was just naive enough to think that I could do it. I don't know what I was thinking.  I got my first two clients in a round about sort of way and then I added another client and another. But I didn't think to take that first jump until someone offered me a freelance job.

What makes Paul + Williams special?

We're unique in that we understand the brands we work with really well. We understand what our niche is and we like those brands that have a history, substance and that make things a certain way.  When selecting brands, our litmus test is:  Do we wanna wear this stuff?  Do we want to take this stuff home?  That's why our relationships are so genuine.

The whole concept of our company is that we only work with a certain type of client and don't water down the work.  Just because it can pay us, doesn’t mean we're going to take it. We want to be passionate about what we work on.

Sometimes the partners (at bigger agencies) will just sign (any kind of) business because they're not on the front lines. From the beginning, we decided that we didn't want to communicate about things that we didn't like and didn't care about.

Agencies often talk about their how important culture is to a healthy business – how do you do things differently at Paul + Williams?

You can get a lot out of this world by being nice to deal with and good to have around. We saw how the agency world can be catty and cutthroat and we just thought, ‘we don't want to be that way.’ 

This isn't Google. We don't have a cafeteria and tons of amenities. But, when people come to work here, they don't have to sit in meetings twenty hours a day. Everyone is friendly. There are no politics or backstabbing. We all sit in one room.

It's not for everyone though.  Some people want (that structure) that big companies offer. 

How do you hire?

Our philosophy with everything is no turnover. No turnover with our clients. No turnover with our staff.  It may not be the most lucrative approach, but you get better things done, you have a better time.  It's another reason we don't want to grow really quickly.

Were there ever any times when you thought you might want to throw in the towel?

At the end of 2009 it felt like the world was ending and it was really difficult for us. Our business wasn't as developed as it is now. When the economy crashed all of our clients cut their marketing budgets and we lost 75% of our business. And the remaining business wasn't paying.  We got to the point where we had no employees. We had to fight as hard as we could just to get work. We lost people. It was tough. It was dark. We didn't think we were going to make it.  But one by one we were able to get work.  And because of that we changed our perspective on things like efficiency and waste. Making decisions based on the long-term. Saving up. 

This has not been all easy. For a time, we almost sold the business.  Now we're so glad that didn't happen. I think I went all of 2010 without getting paid.

As someone who works in marketing, what’s your view on content, and where it’s headed?

I saw someone with the title “content creator” as their social media bio, as if that’s a badge of honor.  The whole idea of “content” doesn’t imply quality; it just implies something to be consumed.  Content has changed so much and is still changing. Blogs are becoming less relevant and things are moving to social media. But I think a brand having a direct line of communication to their consumer is important and very empowering.

The whole online world, like the things that Buzzfeed does, it's crazy and incredible. There is a lot of science and data to it to get the most clicks. On one hand, it's interesting and cool, but on the other hand, it sucks.

Nothing is ever going to be like it was. But I’m not one of those people who wish it would stay the same, believing that print is better, for example. The world changes, this is what happens.

What do you think brands get wrong in marketing?

Social. It's so disingenuous sometimes, robotic, saccharine -y and fake. Asking questions that don’t matter just to try and engage. I hate marketing for the sake of marketing.   I see a lot of really bad fake marketing.

The reason so many people connect with Patagonia is because they have a lot of real core values. They actively pursue those values genuinely. They incorporate it into their product. They stay true to that and then all they do is highlight what they're doing. And so people connect with it.  And almost everywhere I go people say, “I love Patagonia.”  Because it's real, it's not made up.

A lot of brands, you see what they do is so fake. Because they don't have it. It's just a marketing story.  I want it to be good product, good marketing, and good story for a good reason. That's what I'm into.

What are consumers looking for in a brand?

Everyone is looking for something different in clothing. Certain people look for price. Certain people look for design. Certain people look for brand name. Everyone makes that decision differently. Some people don't want to spend time and energy thinking about clothes at all.

I don't judge people by how they dress but when someone puts time and care in what they wear, that can help enhance people’s perspective of you.

 What's the vision?

We'd like to be able to continue to stay connected to the business.  We want to stay involved with our clients and find a way to teach the people we work with, clients and the people that work here. I’d like to be able to pass knowledge down to the people who work here and help them grow.

We never saw the value of being huge just to be huge. Why have a huge company and a complicated life just to make more money?  Not to say I wouldn't want to be rich but I'd rather have a comfortable life.  I want to feel challenged and do good work, and add value to our clients.  Just getting big, it doesn’t seem that fun.

Finally, any advice for someone interested in starting his or her own business?

I see a lot of people who start businesses and start with office space and a phone number first then worry about clients. Get the business first, be working on that business and then get all the other stuff done.

Scott Vaccaro | Captain Lawrence Brewery

The thing I’ve always found most interesting about entrepreneurs is the dichotomy between excitement and fear that exists when you’re building something on your own. Once you have the vision, how do you push through all the times of uncertainty to make something great happen? When I sat down with Scott Vaccaro, the owner and founder of Captain Lawrence Brewing Co to ask him why he had the nerve to strike out on his own in the first place, his response was as charismatic as he is, “Fuck it, why not?”. 

Knowing he would be the perfect interviewee for the first By The Bootstraps (and leveraging an excuse to spend the afternoon of a workday having a few beers), I visited his brewery in Elmsford, NY where he took time off from fixing a broken centrifuge to talk to me about how he got started, the roadblocks he faced along the way, and the threat of corporate beer to the little guys.

1980s & 1990’s B.C. (Before Captain/A quick background on Scott)
Scott’s pioneer batch of beer was made when he was a sophomore in high school and by the time he opened his brewery in 2006 he had over ten years of experience brewing his own beer. He had also traveled the globe to learn about different brewing techniques and served as a brewer at Sierra Nevada brewing company, along with many other formative brewing experiences. His acumen and expertise have earned him a reputation amongst his peers as a craft beer authority. 

2006 A.D. (Always in Debt a.k.a. The Early Years)
As big as Captain Lawrence is now (they’ll produce approximately 28,000 barrels this year), his early days were as humble as any bootstrapping start-up’s. In the tough market of craft beer I asked Scott why he did it, and if there were any dark nights of the soul in those initial years.

By 2006 you’d developed enough of a reputation that you could’ve had a successful career as a brewer in any number of places. What gave you nerve to open your own place? 
“Youthful exuberance and stupidity? I don’t know… It’s like being a chef. To cook your own food you have to open your own restaurant. To make your own beer you have to have your own brewery. I said fuck it, why not.”

And were there any dark nights of the soul starting out?
“There’s never been a time when I wanted to throw it all in. I’ve never once said, “Shit, I want to go home.” I love what I do… [But] there are plenty of times when I was nervous about making payroll on Monday, [thinking] I’ve got no money left to pay my bills with.”

Any specific times when you were feeling uncertain?
“When we first started out - the first account I walked into said ‘no’. I walked outta there with such a knot in my stomach. I was like, “I thought this was gonna be a little easier.” It was 30 minutes of, “What did I just do? Is this gonna work?” Luckily the next three accounts said yes.”

Why did you think that people would be interested in the beer you wanted to make?
“I figured if I made a product that people could get behind, and have a sense of pride in, than it would work. I had a business plan and like any business plan a lot of it was crap, just regurgitated crap on paper, but the one key point in my plan was ‘without a local following we’ll never survive’. Without the consumer we’re nothing. You can’t survive without that.”

What were some early marketing successes?
“Early on the most successful thing was growlers. Our tasting room has been our biggest asset since day one.”

Do you want to grow? Do you want Captain Lawrence to someday be in, say, San Diego? 
“We’re focused on New York. I’d love to sell every last drop of beer in New York, but that’s not feasible. (I’m interested in) getting to a point where we can run efficiently and run a sustainable business, not just growing for the sake of growth.” 

David vs. Goliath
As the craft beer industry booms and the larger players lose market share, companies like AB-InBev (Anheuser Busch) and Miller Coors are snapping up smaller brands left and right. I wanted to know Vaccaro’s experience with interest from outsiders, which, as it turns out, has been considerable.

 Is there any interest from outside investors in a brewery like yours?
“I got a guy calling me up at 1 o’clock in the morning, from San Francisco, saying we’re worth a ten or twenty million dollar check… any brewery over fifteen thousand barrels is getting approached…it’s insane”. 

And what do you think of that?
“I’m against selling to AB, to the big corporations. [Up streaming] taints the craft beer pool. It brings in another unsavory element, but you know, if people want to get out and make money, I guess this is a business.”

What do the big guys get wrong?
“What the big guys get wrong is... Craft beer as a whole is a very personal thing. So I don’t think it’s possible for a company that large to connect with people the way a small company can. They can never be that and that’s why they’re buying small breweries. They’re trying to buy authenticity.”

How have consumer tastes evolved since you’ve started?
“The taste change has gone to hoppier stuff. The IPA growth is insane. People want hoppy beers. Which is the exact opposite of what big beer makes. It’s like anything. You eat a lot of spicy food and then it’s not that spicy anymore. And then you want to try something else. I honestly think that’s why people drink craft beer. Because people want flavor. And so next week we’re making a new flavor. A grapefruit IPA. We’re gonna try it out. And then maybe we decide, shit, that’s our new beer brand.”

(NB - Scott has a dedicated area in his brewery for piloting new ideas and new flavors. Friends, family, and employees have all tried their hand at making new flavors, many with great results. It’s a very ‘open-source’ way of doing innovation, and it also engages his fans to become part of the brand.)

What do you think is the biggest threat to the craft beer industry?
The biggest threat to this industry is truth in labeling. Blue Moon is made by Coors, Blue Point is made by Anheuser Busch, Goose Island is made by Anheuser Busch - Forget about the quality of the beer, I’m not knocking that, they can make the best beer in the world but I feel strongly that the consumer very much wants to know or has the right to know that every dollar that they spend on Goose Island or Blue Moon is going to Coors or AB InBev’s bottom line, not to some guy like me that’s sitting here working on the centrifuge, it’s going to some massive conglomerate… The consumer has the RIGHT to know... [A company] can brew 90% of their beer in Tennessee, but as long as they brew 10% in Brooklyn, they can put ‘Brewed in Brooklyn’ on every can.” 

What’s the future of the market?
“That’s the million dollar question right there… I think the change is permanent. People have found a new product that they like and they’re not going back to drinking bud light all the time. Craft beer volumes will continue to grow.

If private equity keeps flooding in it’s gonna drive prices down. And the bar owners are gonna love it. But that’s gonna hurt people like me. Goose Island is a great example. You know Goose Island? A number of years ago before Anheuser Busch bought them - a keg of Goose Island IPA cost $160 bucks. Now they’re selling $90 kegs of Goose Island here and trying to steal [tap] lines from someone like me who’s selling a $160 keg of IPA. They’re going to a bar and saying, why not pay $90?”

(Often, Captain Lawrence, or any craft beer brand operating at the cost of small business, loses a tap at their local pub to a ‘craft beer’ made by ‘big beer’)

Any last advice for someone who wants to start their own brewery?
When I started this place I had no wife, no kids, no mortgage.
I got nothin’, I got nothin’ to lose. 

It takes a long time to get to positive cash flow; start with a lot of money and make it somebody else’s.