Unicorn Founder Reacts to His Old Philosophy from Before His Success
The Most Meaningful Interview I've Done
Hey all, I wanted to share a piece on "authentic learning" and AI we published at the Cosmos Institute which I particularly enjoyed: the author weighs AI’s model of learning as optimization against Plato’s ideal of inquiry and Augustine’s view of inner recognition. The essay argues that learning is not only a matter of getting things right, but of being transformed into the kind of person for whom getting them right is not accidental.
This is the most meaningful interview I’ve done: seeing my friend Francis Pedraza react to conversations we had 8 years ago before his success.
Francis Pedraza now runs one of the fastest-growing AI unicorns worth $2 billion, but when I met him a decade ago he was at a low point: broke, recently single, having failed his first company, and struggling with his second. We became fast friends over our love of the Great Books and recorded 6 hours of conversations on philosophy, entrepreneurship, and God.
This summer, I invited Francis back to listen to his old self and see how success has changed his views. The first part of this video is our latest interview in 2025 where he reacts to our past conversations and the second audio-only part is the highlights from 2018.
What’s so cool is that Francis called his shot. Even when everything wasn’t working, even when he was a “failure” by all accounts, he boldly predicted his success and laid out a laughably ambitious plan that seemed impossible. I called him Don Quixote to his face, but boy am I happy that I was wrong!
What’s so beautiful, when you watch these two interviews together, is to see how Francis’ obsession with philosophy, which made him seem like a complete buffoon in 2018, became the cause of his success. It was because of his continued study of the Great Books that Francis was able to come up with ideas no one else saw, persevere through dire challenges, and finally share his newfound wealth in a dignified way.
Francis’ favorite book is The Once and Future King, the hero’s journey of King Arthur. He fell in love with this book as a kid and credits it with saving not just his company but his very soul as an adult. What you are about to witness in the next two hours then, is how Francis lived out this book. This is the hero’s journey of Francis Pedraza.
Topics We Cover:
4:47 The Purpose of Education Is Action
19:03 The Anti-Progress Tech Founder
35:05 Billionaires Have No Cultural Appetite
47:48 Turning Failure Into a Billion-Dollar Win
59:28 How Success Corrupts Entrepreneurs
1:06:52 Thinker-Doers: Where Ideas Meet Action
1:11:31 The Brutal Truth About Entrepreneurship
1:36:12 Heroism in an Anti-Heroic Age