From Gut Punch to Exit

or "Do You know how to skate?"

Some moments in your career come gently, like a tap on the shoulder. Others hit like a knockout punch.

I talked with Kara Weber about this on my podcast Critical Moments, and her story is a perfect example of how the worst moments can set you up for something even better—if you’re willing to stay open to change.

Kara and I met almost 30 years ago when she was helping build Tripod, one of the first online communities and website builders. This was before anyone really knew what a personal website was, and long before social media made it easy to put yourself online. She was one of the people shaping the early internet, and I was… well, trying to keep up. We’ve stayed friends ever since, watching each other’s careers take shape in ways neither of us could have predicted back then.

Fast forward a couple of decades, and Kara was stepping into her first President role at Brud, a high-flying, venture-backed startup. (Lil Miquela, anyone?!) It was one of those companies that had everything—big-name investors, a celebrity-infused business model, and a shot at being the next big thing in media. It had all the buzzwords—AI, virtual influencers, storytelling 2.0. It was ambitious and had the potential to be massive.

And then March 2020 hit.

The world shut down overnight. The strategy she’d spent months building? Gone. Revenue? Stalled. The business model? No longer viable. She had 60 employees looking to her for leadership, a board expecting her to navigate the chaos, and a family to take care of in the middle of a global crisis.

No roadmap. No playbook. No certainty.

It would’ve been easy to panic. Most people would have. But Kara had been here before.

Years earlier, as a freshman at Williams College, she walked onto campus fully expecting to play soccer. It had been her identity for years—she was a captain, a top scorer, the kind of player who lived and breathed the sport. Then she got injured and cut from the team. Just like that, everything she thought she was—gone. It was a gut punch. But instead of sulking or giving up sports altogether, she did something unexpected.

She went to a party, met a guy, and in the middle of small talk, he asked, Do you know how to skate?

Turns out, she did. And a few months later, she wasn’t just playing a new sport—she was leading it. She became the first varsity captain of the women’s ice hockey team at Williams.

That experience—the moment when your identity gets ripped away, and you have to decide what now?—turned out to be exactly what she needed when the pandemic flipped her world upside down.

At first, she did what every leader in that moment did: tried to stabilize the team, reassure employees, keep the business alive. But the reality set in quickly—there was no way forward on the path they had been on. Every deal was either paused or canceled. The vision of building out a media empire around virtual influencers and real world experiences was suddenly impossible.

Instead of fighting to hold onto a plan that no longer made sense, Kara did something few leaders are willing to do.

She let go.

She threw out every assumption about what the business was supposed to be and started listening—really listening—to her team. They were younger, creative, and looking at the world differently. They challenged old-school ideas about content, media, and audience engagement. They weren’t just building for fans—they were building with them.

And that’s when everything changed.

Instead of trying to survive with a broken business model, they flipped the script. They leaned into blockchain, NFTs, and decentralized ownership. Instead of treating fans as passive consumers, they turned them into active participants. They weren’t just building a company; they were rethinking what ownership and engagement could look like in media.

It was a huge risk. It felt too early, too radical, too uncertain.

But it worked.

A year and a half after that March 2020 punch to the gut, Kara and her team sold Brud to Dapper Labs, one of the biggest players in the space. What could have been the end of the road turned into a successful exit, driven by a willingness to rethink everything.

The thing about leadership is that we like to believe it’s about having the answers. In reality, it’s often about knowing when to let go of the answers you thought you had.

Kara didn’t force a failing plan to work. She let go, listened, adapted. That’s what great leaders do.

Her story is a reminder that the best opportunities don’t always come when you’re ready. They don’t arrive on a neat timeline or fit within the plan you had for yourself. Sometimes, they show up disguised as failures, gut punches, and moments that feel like everything is falling apart.

The trick is knowing that these aren’t the moments to back down. They’re the moments to step up, skate onto the ice, and build something new.

Listen to Kara’s full story on Critical Moments on Spotify, Apple, Amazon, or wherever you listen to your podcasts. And, seriously, if you listen on platforms other than these three, let me know.

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