We love grabbing drinks with our entrepreneur friends because they always have the craziest stories. Sometimes it’s a big, unexpected win. Other times it’s a problem that came out of nowhere and couldn’t possibly have been foreseen. There is so much to learn from these stories and so we asked some of the brightest entrepreneurs and creatives in the community to share some of those stories below.

Tyler Kuwamoto

One of the most powerful stories I’ve experienced in this field wasn’t “crazy” in the dramatic sense—it didn’t involve a wild procedure or some once-in-a-career emergency. But emotionally? It hit me harder than I ever expected.

A woman came into our office who hadn’t smiled in what looked like years. You could see it all over her—she was ashamed, anxious, withdrawn. She barely looked up when she talked. She apologized for her teeth before I even had a chance to look. And as a dentist, you start to realize—people often carry emotional weight around their dental health. It’s not just about function or aesthetics. It’s about identity, confidence, how you show up in the world. Read more>>

Madison Daube

One of the wildest moments I’ve had as a photographer was at a Jaripeo—a traditional Mexican rodeo—where I captured a serious rodeo wreck mid-ride.

It was one of those moments I never expected to experience behind the lens. As photographers, we prepare for dust, chaos, and emotion—but I wasn’t prepared to potentially document someone’s last moments. The bull rider was thrown violently and trampled, and I kept shooting out of instinct. Read more>>