“[My dad] took me down to Child Protective Services and dropped me off and said, you can't come home .… What it made me do was prove that he was fucking wrong about me.”
To say I was floored by my conversation with Martin Tobias, founder of Incisive Ventures, would be a mild understatement.In this episode, Martin tells this traumatic story, and how that chip on his shoulder became fuel: from teenage exile → Microsoft manager → IPO → prolific VC.
But this isn’t a fund-size story. It’s about what trauma does to us, why proving someone wrong only carries you so far, and how to find meaning after you already “won.
”We covered poker, tacos, watches, and girl-dad life — many things we both love and share. But what stuck with me most is Martin’s honesty about the full arc: from son, to entrepreneur, to VC, and back to father.
For founders, LPs, or anyone who still thinks success is a straight line, Martin’s story is a reminder: resilience is forged in pain, but sustained by curiosity and craft.
In this episode Martin and I dig into:
🚪 Getting kicked out at 16 and why chips on your shoulder put chips in your pocket.
🎲 Why poker is the best diligence tool for founders (and how CEOs vs. CFOs play differently).
🕰️ Watches, tacos, and the craftsmanship test for founders.
👨👧👧 Girl-dad stories and what parenting teaches us about investing (and vice versa)
.🌊 Surfing, longevity, and finding joy after you’ve already “made it.”
💸 The worst days in venture — and why dishonesty is the true deal-killer.
Martin’s vulnerability surprised me, and I think it will surprise you too.
Chapters
00:00 “You can’t come home” — teenage exile as fuel
04:33 Why Martin chose pre-seed after raising $550M as a founder
08:14 Politics vs. craft: why big-company life left him cold
09:43 Parenting, girl-dad moments, and startup curveballs
14:26 Longevity, biohacking, and investing in healthspan
21:05 Craftsmanship in founders (and why manual watches matter)
27:58 From duct tape to scalable cloud: Vega Cloud’s reinvention story
30:09 Procurable AI: solving your own customer pain
34:55 Poker as due diligence: math vs. psychology
41:20 Handling bad beats — in poker and in startups
44:10 Trauma, drive, and proving Dad wrong
47:32 The worst day in venture: backing a fraud
49:20 Gratitude for Ron Conway, the OG angel
50:08 Legacy and letting kids live their own lives