I moderate a lot of firesides. Part of the job is sitting next to someone brilliant and asking the questions our Builders are too nervous to ask themselves. Every so often, though, a guest walks in and answers the question before I've even finished asking it. That's what happened with Ken Chenault.
I said as much to the room, half joking, because I couldn't help it. Ken opened with his own story. Finance, then an early HR tech startup, then General Catalyst, then Benchstrength. By the time he finished, he'd already walked through the exact structure we drill into our Builders every single day. What was the problem. How did you think about it. How did you feel. Why did you act. Nobody coached him through it. He just told the truth about his path, cleanly, and it turned into a masterclass on how to introduce yourself. No list of degrees. Just a thesis.
And the thesis was blunt. Venture is the most network-driven industry there is, and that network has never reached everyone it should. Groups that make up 75 percent of the world's population receive about 5 percent of global capital. One percent goes to Black founders. He didn't cushion it. If you keep eating at the same five restaurants, he said, you never try new food. I've been chewing on that line for days. It's such a simple way of saying something we say all the time at Pursuit in far more complicated language. Access is the whole game.
Then AI came up, and this is the part I keep replaying. Not because it was flashy, but because it gave our Builders something real to hold onto. Ken called it the "flashlight test." Remember flashlight apps? For about a year they were among the most downloaded things in the App Store. Then Apple put a flashlight into the iPhone itself, and the whole category disappeared overnight. So here's the question, for a founder or for someone applying to a role: does what you're building get better as the models get better, or does it just get replaced by the model? Uber doesn't get flashlit. Better models make its matching and pricing sharper. That's the target. Build the thing that improves when the tools improve. Not the thing the tools eventually swallow.
He tied that straight back to something we say in every classroom here. AI is a tool, not a solution. What can't be automated out of a person is their creativity, their hunger, their curiosity. When I asked what he actually looks for in founders, he didn't say pedigree. He said curiosity. Boundless curiosity, was how he put it. Because things move too fast now for anyone to stay still and still be valuable.
Then there was the Lookbook. I'll admit, I set him up a little. I knew what was coming. He'd looked at six projects our Builders shipped in six weeks, and told the room, plainly, that he's evaluated real estate startups doing the same thing one of our Fellows built as a class project. Interviewing is dead. You're auditioning now. Showing up with something you built, unprompted, wins the audition before you open your mouth. He compared it to what GitHub became for engineers. Not a resume. Proof. If you were planning to spend five hours on your Lookbook profile, he told them, spend ten.
What stayed with me walking out wasn't a single line. It was watching a room full of career switchers, people who came to Pursuit because the traditional path either closed on them or was never built for them, hear a legendary investor confirm what we tell them on day one. Your background is not the barrier you think it is. The barrier was always access. And access is exactly what this room, this program, this network, exists to rebuild. Ken said he wants New York to be on par with the Valley. After watching that room, so do I.
Thank you to Ken and the Benchstrength team for spending real time with our Builders, and for reading through their commitment statements before ever walking in the door. That mattered more than you know.
If you're hiring right now and want AI-native talent who can actually transform how your org works, or if you'd like to join us for a fireside and share what you know with our Builders, reach out.
Devika Gopal Agge
Chief Development and Employer Services Officer, Pursuit
devika@pursuit.org
