A podcast · hosted by Martin Tobias · Incisive Ventures
Conviction
before proof.
Founders, professional investors, poker players — and anyone deploying capital under low information and huge uncertainty. The bets that pay off the most are the ones that sound stupid at the time. The First Bet drags them back to the moment before they knew — what they had to go on, why they bet anyway, and what they saw that everyone else missed.
The Test
Every great capital allocation sounds stupid before it works.
Couch-surfing for strangers.
Buttons that summon cars.
A check into three slides.
The First Bet sits with the people who pushed chips in anyway — and pulls apart what they saw that nobody else did.
The Lens
Every guest has one rule they carry into every bet.
Not a story — a portable heuristic. The thing they reach for when the information is thin and the chips are already in.
You can make these relatively cheap asymmetric bets over and over and over again… any one of the individual ones failing is not catastrophic.
This wasn’t a reckless leap, it was an asymmetric bet — with capped downside and massive upside.
Intuition—the tool most investors treat as a superpower—is demonstrably unreliable in early-stage VC. Intuition only works in environments with clear feedback loops. Early-stage ventures? Not exactly that environment.
Everyone's a gangster until they gotta wire the money.
I'm not a risk taker. I'm a risk trader.
The Feed
Latest episodes
EP15 Mahesh Narayanan: Finding mission driven Founders
nvestor Mahesh Narayanan shares how founder conviction, coachability, and customer demand helped Improve on Health evolve from an early idea.
Listen →EP14 Eric Jorgenson: Idea Guy
Eric Jorgenson and Martin Tobias unpack asymmetric bets, power-law outcomes, and how a side-project book became a career-changing breakout.
Listen →EP13: Greg Raiz - Data driven Founder Selection
Discover the founder traits, execution signals, and research-backed insights that help investors make better startup bets.
Listen →EP12: Kirby Winfield - Founders first VC
Investor Kirby Winfield on backing contrarian founders, defense tech, and the high-conviction bets that shape early-stage venture.
Listen →EP11: Sohun Sanka - How an Entrepreneur thinks about going All In
Martin Tobias and Sohun Sanka explore smarter startup bets, capped downside, AI-powered software, and the decision to build without raising money.
Listen →EP10: Howard Lindzon - Investing in the "Degen Thesis"
Howard backed Robinhood and Alpaca when almost everyone else thought trading was a bad bet, and how “low information” to opportunity changed everything.
Listen →The Newsletter
Never miss a bet.
Each episode: the bet, the Lens, and the transcript — the book, serialized.
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