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Stories from the edge of entrepreneurship, adventure, and unmapped places

The real adventure begins when something goes wrong. A lot like entrepreneurship.

Building a more inclusive future for startups

“Everything starts with story,” Santiago says. “Your greatest asset is not AI. It’s not Claude code. It’s your story.” For entrepreneurs trying to build companies in the middle of an AI boom, that remains his clearest advice.

That time Pussy Riot opened for the Creative Business Cup

Afterward she leaned over and handed me a small box. Inside was a pair of Donald Trump underwear. White cotton with fuzzy blond hair stitched on top. It was equal parts satire and warning. She looked at me and said quietly, “Americans are not going to like having a dictator.”

Be so damn good they can’t ignore you

She is a woman in sports and media and branding, which means she has spent plenty of time in rooms where a man doing the exact same things would be called driven while she gets called “too much, too loud, too aggressive, too confident.”

The Shoe Dogs

Some founders arrive with pitch decks and market analysis. Tammy and Ludo arrived with a camper van, a few decades in the footwear business, and the suspicion that the industry had drifted too far into disposable fashion.

Starr Hall never learned to sit still

Starr Hall has this formula and it repeats like clockwork: She builds things. She makes a shit ton of money. She exits. She gets bored. She moves on. “I know after two years, I’m out,” she says. “I’ve done what I can do. I need something new.”

Living the Wahoo Way

Before Wahoo’s Fish Taco became a global brand, Wing Lam was handing out tacos to starving surfers in Costa Mesa parking lots.

Drink the fucking wine

Scott Halford on leadership, clarity, the human brain, and how great founders learn to slow down and question assumptions.

Lunch With David Granger

The machinery of media looks very different now. But, we both agree, editorial judgment still has a place. Maybe now more than ever.

The Ducati didn't make it

The city of Fort Collins mailed the ticket to my husband’s ex-wife, who does not live in Fort Collins, nor does she ride a Ducati. She was furious. To this day, none of us understands how that happened. But who cares? It was fantastic and she’s still pissed. I call that a win.

Barbara Brooks is not invisible

Up until that point, she hadn’t thought much about her age. It wasn’t part of how she moved through the world or how she understood her value. But as the rejections accumulated, it became clear that it was part of someone else’s calculation she could no longer control.

The Sparrow in the Razor Wire

Inside prison he devoured books on entrepreneurship, spirituality, mindfulness, and personal development. One idea kept circling in his mind. What if prison was not the end of his life? “I asked myself why do I have to view prison as punishment. Why can’t this be a place where I remake myself.”

In L.A., people trust one guy with their pricey supercars

A lot of founders start companies because they want to build. Others start them because they get tired of waiting around inside systems they don’t control. Elrod sounds like the second kind.

Entrepreneur, Seeker, Vagabond

For a stretch of time he lived in a converted Volkswagen bus parked on the beach in Tulum. Everything he owned fit inside the van and he smiles as he remembers it as one of the most liberating periods of his life. “It was the freedom of not having anything.”