Execution

#186 Adam Spector — Disrupt Yourself Before Your Boss Does It for You

Watch now | A 4x founder, 200+ company investor, and former Twitter PM explains why the employees who survive the AI era are the ones who build the…

Jun 4 • Caden Damiano

47:49

#185 Caden Damiano - Reinventing Your Career for the AI‑Native Era

Watch now | AI Didn’t Change the Game—It Changed Who Can Play

Jun 2 • Caden Damiano

54:54

#184 Adam Callinan: Operational Pain Creates Product Taste

Watch now | Adam Callinan didn’t set out to build a profitability platform. He set out to not go broke. The lessons he learned through operational pain…

May 28 • Caden Damiano

50:48

#182 - Tyler Wells: It’s Way More Expensive to Talk About Building Now

Watch now | The PM who spends a week in whiteboard sessions has already lost. Braingrid.ai whose agents act as both product manager and tech lead…

May 21 • Caden Damiano

50:18

#179 - Gal Ko: The Founder Is the Product Now

Watch now | As AI commoditizes software faster than ever, Gal Ko on why the most durable moat a founder can build is themselves — and why podcast…

May 11 • Caden Damiano

48:58

#177 - Marlena Sarunac: The One Phrase That Ended a Startup's Six-Month Sales Plateau

Watch now | Nobody was buying. Marlena Sarunac spent weeks with a clients team before they landed on three words — and the sales conversations started…

May 4 • Caden Damiano

43:48

#176 - Dean Phillips: The Cold Email That Became a Head of Product Strategy Job

Watch now | He built a 25-slide deck, emailed CEO Zeb Evans, and essentially said: you should build this. Zeb's reply was a job offer.

Apr 30 • Caden Damiano

1:13:05

#174 Pete Hunt: He Built a Better Sales Forecast on a Plane. That’s When He Knew Salesforce Was Broken.

Watch now | Pete Hunt, CEO of Dagster Labs and an early member of the React.js team at Facebook, reframed how I think about what “real” revenue…

Apr 23 • Caden Damiano

46:38

#173 - Yaron Schneider: The Most Valuable Thing an Engineer Can Do Now Isn’t to Write Code

Watch now | When AI can generate code faster than humans can review it, the bottleneck shifts to something harder to automate: thinking.

Apr 20 • Caden Damiano

44:01

#172 Ben Johnson: When The Cost of Writing Code Drops to Zero, What Are Engineers Paid For?

Watch now | Ben sold his company to LegalZoom and now runs a software factory powered by AI agents. He explains what changes, and what doesn't, when AI…

Apr 16 • Caden Damiano

52:11

#171 Karl Simon—What careers look like moving forward, why your data graph IS your AI competitive strategy & design AI systems that adapt to…

Watch now | How a strong data graph enables agentic decision-making, why your data graph IS your competitive strategy, and how AI is eliminating the…

Apr 13 • Caden Damiano

45:24

# 170 Jake Stauch, Co-Founder of Serval: Bet before the technology works, build infrastructure over raw models, and scale enterprise AI…

Watch now | The wireless communication analogy and infrastructure-first philosophy that helped Serval raise $125M at a billion-dollar valuation within…

Apr 9 • Caden Damiano

44:55

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