Bootstrapped, Profitable, and Proud: The Huckberry Origin Story

BACK IN 2010,
Rich and I were freezing our butts off on a rickety chairlift on the backside of Palisades Tahoe when we decided to go for it.
Looking back, we were far too naive to know exactly what it was, but we definitely knew what it wasn’t – cranking out spreadsheets for 90 hours each week for the rest of our lives. Still, gaining the courage to leave our safe, lucrative jobs wasn’t easy. As Jerry Seinfeld might say, it was like tipping over a vending machine— you don’t just push it over, you have to rock it back and forth a few times.
Having discussed our idea over countless beers after work, we knew in our bones that Huckberry needed to exist. There were men’s stores, sure. Adventure magazines, too. Yet nothing out there spoke directly to us – young guys who lived in the city but lived for adventure, and we envisioned a brand that was equal parts store, magazine, and inspiration to help guys suck the marrow out of life.
So in the summer of 2010, we left our jobs, invested $10,000 each from our savings to form Huckberry LLC, and set out to scratch our own itch.

WE CHOSE THE NAME HUCKBERRY
because we both loved Mark Twain’s Adventures of Huckleberry Finn and thought Huckberry was the perfect totem for the spirit of adventure we wanted our brand to embody. More practically speaking, Huckberry.sbs was available on GoDaddy for $9.98 and Huckleberry.com was not.
We hit the trade show circuit in search of other Davids taking on Goliath. Most brands looked at our self-designed business cards, smiled with amusement, and said no. But enough said yes—people like Dan at FlyLow, Mark and Jedd at Topo Designs, and Jason McCarthy at GORUCK. F*cking love those guys to this day.

We decided not to pursue venture capital. We wanted to build our business on our terms. Towards Patagonia and its organic Let My People Go Surfing brand, and away from the VC-fueled boom-or-bust brands that were chasing it.
So we hustled. Working out of our apartments, we read Photoshop for Dummies cover to cover, and designed Huckberry 1.0. Our friend’s younger brother, Jimmy, helped code it between classes during his junior year at UC Berkeley. Our first website wasn’t pretty, but it worked, and as a mentor once told us, you always throw out your first pancake.
In April 2011, we flipped the switch, and huckberry.sbs| New Window| Redirects to homepage went live.

OUR COMMUNITY
began to grow…slowly. We couldn’t afford to advertise so we got creative and partnered with the Art of Manliness (thanks again, Brett 👊) and Outside. Brands began to ask how they could get featured on Huckberry. When our apartments started to overflow with inventory and cardboard boxes, our roommates and the local barista suggested we get an office. So we rented one in San Francisco’s North Beach neighborhood for $600 a month. We felt like kings; it didn’t matter that our castle was only 296 square feet (well, ~350 square feet if you include the bathroom).
We built our team. Ali joined. Jeff. Ben. Even our local barista Eli joined as our first “head of operations.” No prima donnas in that group. Every day at 4pm it was pencils down and packages out in a blitz of boxes, beer and tape. At 5:25pm, we’d carry each box down to the street, grab a mail cart, and push it uphill both ways in a blizzard to the post office. If you’ve ever lived in San Francisco, you know the uphill both ways part is true.

WHEN THE INVENTORY BEGAN TO OVERFLOW
into our bathroom, we started looking for a warehouse. When we had to store inventory on our roof overnight, we really started looking for a warehouse. In the spring of 2012, we found one in San Francisco’s SOMA neighborhood, and not long after moving in, Ali decided it could use a 12-foot rock wall.
The days were long but the years were short. Time raced ahead and our community grew. And grew. And grew some more. By late 2015, our warehouse was bursting at the seams and we were in need of more space. We ran a national search but quickly zeroed in on Columbus, Ohio — Richard’s love of the Buckeyes may have had something to do with it.
Later that year we purchased Flint and Tinder| New Window and saw the power of making products directly for our customers. We kept Flint and Tinder’s brand ethos and maniacal focus on quality but tailored the fit and fabric to our customers. With those changes in place, FNT started to earn higher average customer reviews and lower return rates compared to our third party brands.

NOT LONG AFTER,
we had the opportunity to acquire another brand, but to do it we’d need to raise our first outside capital. We had grown Huckberry to tens of millions of revenue on our initial $20,000 investment, yet despite all of the growth, it often felt like we were flying too close to the sun on wings of cardboard boxes. Thankfully, by this time, we had a solid rolodex of angel investors who were already VIP customers, and so we were able to raise our first outside capital while maintaining control of the company.
By 2019, Huckberry was humming and we had millions of guys reading our newsletter each week. Because we never had money in the early aughts to pour into Facebook ads, we invested all of our marketing might into creating the most inspiring newsletter in the inbox. We explored Chicago with Jeff Tweedy of Wilco. Kelly Slater showed us his secret spots in Kauai. Matthew McConaughey got philosophical with Ben about fatherhood. We’ve always said that Huckberry isn’t just a gear company, it’s an inspiration company, but around this time we realized that we had pretty much organically created a new business model that combined the best of the retail and media industries. Others took note too, with big spirits and lifestyle brands investing into the Huckberry platform. And Huckberry Media was born.

WE WERE ROLLING.
And then March 2020 coughed its way into the picture. Rich and I had a great run in the Bay Area, but we’d been itching for a change in scenery for a few years at that point. Austin had always been the sister city for Huckberry, and over the years we had worked with tons of artists, musicians, and brands from ATX. We loved the young, active culture and the rich arts scene, and the low and slow style of living.

RICHARD AND I OFTEN GET ASKED
what the end game with Huckberry is, and every time I hear that question, I think about that scene in the movie Heat, where Robert De Niro and his crew say that they don’t rob banks for the money — “the action is the juice.”

As I type these very words 30,000 feet in the air, our creative team is in Iceland shooting our holiday campaign, our media studio in Austin is interviewing a famous musician, our buying team is in Tokyo scouting new brands, and our product team is in Portland searching for technical fabrics.
This is our action. This is our juice.
Our vision is to build the most loved and influential men’s lifestyle brand. We want to be the one stop men’s shop for guys, to pioneer the everyday adventure lifestyle category, and to serve it with an innovative new business model that blends the best of retail, media, and community.
It’s why in the following years you’ll see us open up Huckberry stores, expand our product portfolio, double down on inspiring media shows like DIRT, and maybe even launch a four-season Huckberry Adventure Resort (think cat skiing, mountain biking, fly fishing etc. mixed with concerts and live shows — this is Huckberry nirvana).
We’ve always believed that a Jedi draws his strength from the Force — that you all are Huckberry, and we’re just the stewards. So in perhaps one of the greatest understatements of all-time, we’d like to say thank you for supporting us on this journey. Thank you for bearing with us through our growing pains, false starts, and the time I accidentally Instagrammed six pictures of the inside of my pocket on the Huckberry Instagram while dancing with my wife at a concert.
We promise that everything about the Huckberry experience — the gear, storytelling, customer experiences et al. — is going to get radically better in the years ahead.
And, lastly, if you’re reading this and currently rocking back and forth a vending machine of your own, know that with all of the entrepreneurs we’ve advised over the years, no one has ever said, “I’m going to give up on my dreams.” They just say, “not now” or “first, I just need to.” If we’ve learned anything about entrepreneurship, it’s that there is no playbook and no “right time” to start a company.
Life is short. We only get 4,000 weeks — at best. So let it rip.
See you out there.
