Bill Bryson once worked out that if you go back 25 generations, there are no fewer than 33 million men and women whose lives had to collide in precisely the right order for you to exist. I read that passage the night before this conversation with Dave Finnegan, and something about it felt like the right way to open a new season. Not with a take. Not with a prediction about agentic commerce or the latest platform shakedown. With a reminder that none of us got here by ourselves.
That’s Finn. If you know him, you already understand. If you don’t, this episode is about to fix that.
Dave Finnegan, Finn to his friends, and now to you, is an operating partner at BlackFinn, an advisory board member for NRF’s CIO and CMO Councils, a member of the Explorers Club, a man currently pursuing a master’s in anthropology at Harvard, and the kind of person who makes you feel like a better version of yourself just by being in the room. He helped launch Build-A-Bear. He ran the show at Orvis during their best years. In 2022, he took a year out to visit every continent and interview indigenous leaders, scientists, and, his favourite story, the librarian of the world’s oldest library at the Monastery of St. Catherine. He’s the Ross Geller of our industry, and I mean that as the highest compliment.
We started with ancestry. His dad, a quiet cowboy poet from a mining town in Western Montana. His mum, a driven Scot. A handful of aunties who made sure he could get away with nothing. That combination, quiet resilience and entrepreneurial steel, runs through everything he does. When I asked him about the strong women who shaped him, he traced a direct line from those aunties to Maxine Clark at Build-A-Bear, to Vicky Cantrell, to the women throughout his career who matched the energy he was raised with. Not many people draw that line so clearly, or so generously.
As always when speaking with him, came a moment I didn’t expect. Finn told me about sitting fireside at the Explorers Club with some young engineers who were working on the first anthropomorphic robot for the International Space Station. Two arms, no torso. And the thing that had consumed their research wasn’t power or processing. It was likeability. They’d learned that if a robot moves too fast, gets too close, acts too mechanically, humans reject it. The unwritten rules of what makes us human, our comfort with proximity, our response to rhythm and pace, had to be programmed in. I asked him if the tools are changing the humans. His answer was better than my question: the tools are teaching us about ourselves.
This is where the conversation turned into something I’ll be thinking about for weeks. I’d sent Finn a story about Canvass White, a 21-year-old engineer who, in 1817, walked over 2,000 miles across England on his own dollar, studying how the British built their canals. He came back with drawings, surveying instruments, and, crucially, knowledge of hydraulic cement that would waterproof the locks of the Erie Canal and save what was being called Clinton’s Folly from becoming a hundred-year money pit. Bill Bryson wrote that Canvass White didn’t just make New York rich, he helped make America. And nobody paid him for the cement. Over 500,000 bushels used, not a penny honoured.
Finn’s read on it was characteristically sharp: real progress happens when someone takes responsibility for a problem that no one owns yet. Everyone saw the water leaking out of the canal. Only one person went to do something about it. That’s the line between observation and action, and it’s the line most of our industry is still standing on the wrong side of.
And then he said the thing that I think defines this episode: “They learned how to build the canal by building the canal.” No playbook. No case study. No five-year-old proof point to benchmark against. They figured it out in the doing. His argument, and I think he’s right, is that being early with AI is less about being right than it is about being willing. Jefferson called the Erie Canal project “near madness.” They built it in eight years. Willingness beats certainty. It always has.
What I love about Finn is that this isn’t just philosophy for him. Through BlackFinn, he evaluates companies for investment, and he told me that at least half of what they assess is the person, not the product. Can they attract others? Will they own problems nobody else will touch? Do they build rockstar teams? In a market where every investment target is months old, not years, the human part of the equation isn’t soft skills. It’s the whole game.
We talked about how anthropology gets miscast as old stuff. It’s not. It’s the study of human meaning, and human meaning didn’t stop being relevant when we started building large language models. The people who understand why humans do what they do are going to be the ones who build the things humans actually want. That’s not a prediction. That’s a pattern.
Finn’s song pick was Temple of the Dog, “Hunger Strike.” About remembering where you’re from as you become successful. About the people who got you there. It couldn’t have fit more perfectly if he’d written it for this episode.
And yes, I did ask about what goes on under the kilt. A Scottish gentleman never tells.
This is Season 3 of the Struggle Bus. We’ve changed the look but not the soul. The conversations are still about the beautiful friction of building, the humans behind the hype, and the belief that shared empathy isn’t a soft skill, it’s the fuel that drives innovation. Finn was the perfect guest to open with because he embodies all of it. Pour a large one. We’re just getting started.
Season 3 of The Struggle Bus is brought to you by Sumo Blue and Omnisend. There’s still room for one more at the table, if you’re interested, you know where to find me.
