Mike Tyson Said It Best

A crash course in entrepreneurship from our co-founders, Andy and Richard.

Over 15 years ago, 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—staring at spreadsheets 90 hours a week for the rest of our lives.

Still, gaining the courage to leave our jobs wasn’t easy. But in the summer of 2010, we quit them and invested $10,000 each from our savings to form Huckberry LLC. The rest, as they say, is our history.

Since then, we’ve skied volcanoes in the southern hemisphere and explored Kauai with Kelly Slater, but the most fun and rewarding adventure of our lives has been founding and leading Huckberry. Fifteen years in, here are 15 hard-won lessons we’ve learned along the way.

Andy and Richard,  
Huckberry Co-Founders

1. Burn the Boats on the Beach

You play differently when you go all in and have everything to lose. For us, that moment occurred on a ski lift when we made a blood-brother pact to quit our jobs.

To this day, we still love playing with our backs against the wall, as we’ve turned down a lot of money for a small percentage of our shares—multiple times. —Richard

2. Pray for Rain

One of my favorite Huckberry memories is shooting a catalog with Kelly Slater in Kauai in 2017. We were still a small company, and it felt surreal picking him up from the airport. On that trip, something he said stuck with me. When conditions are miserable and the waves are terrible, most guys complain. Kelly did the opposite. He leaned into the rain and saw the bad conditions as an edge.

The best don’t wait for perfect conditions—they weaponize imperfect ones. As Ayrton Senna famously put it: “You cannot overtake 15 cars in sunny weather… but you can when it’s raining.” —Andy

3. Momentum Builds Momentum

What’s the hardest part of waking up early in the morning? Putting your feet on the ground.

It’s incredible how small actions and forward progress can inspire and open up more progress. When you're stuck in a rut, the best thing is to just try something, anything. Take that first step, put your feet on the ground, and GO! I have a banner in my office with “Action This Day” on it to constantly remind me of this. —Richard

4. Everyone Has a Plan Until They Get Punched in the Face

Our original plan was to sell adventure travel experiences along with the gear you needed for each adventure. I say “original” because one week before launch, we learned that our payment processor wouldn’t handle travel transactions unless we forked over a $250k deposit. We obviously didn’t have the cash, so we quickly (and painfully) changed our strategy.

Mike Tyson had it right. “Everyone has a plan until they get punched in the face.” From there, it’s that next moment that defines you. How do you respond? How do you improvise? —Andy

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See You Out There

Stopping for food nearly 7,000 feet up at Hidden Lake Lookout, one of the last remaining Washington lookouts still open for overnight stays.
📸 @a_souza_photo
📍North Cascades, WA

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Mike Tyson Said It Best

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