Jerry Neumann is a Columbia University professor, author, and retired investor who was named one of the “100 Best Early-Stage Investors” and one of the “Most Important VCs in New York” by Business Insider. He co-wrote Founder vs Investor, runs the iconic blog Reaction Wheel, and has spent decades dissecting how startups really win—not in theory, but in the messy, unpredictable reality of markets, psychology, and human behavior.

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Uncertainty Is Your Moat: Jerry Neumann on How Real Breakthroughs (and Great Investments) Are Made

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Uncertainty Is Your Moat: Jerry Neumann on How Real Breakthroughs (and Great Investments) Are Made

Haggai Klorman Eraqi

Dec 10, 2025

🎙 Listen to the full episode on Spotify, Apple, and YouTube.

Jerry Neumann is a Columbia University professor, author, and retired investor who was named one of the “100 Best Early-Stage Investors” and one of the “Most Important VCs in New York” by Business Insider. He co-wrote Founder vs Investor, runs the iconic blog Reaction Wheel, and has spent decades dissecting how startups really win—not in theory, but in the messy, unpredictable reality of markets, psychology, and human behavior.

This episode is a field guide for founders and investors who want to understand the only force that consistently produces breakout companies: UNCERTAINTY.

Jerry argues that when the future is knowable, incumbents win. When it’s unpredictable, founders have a shot—because uncertainty is the brief window where giants hesitate and entrepreneurs can sprint. But that window closes fast, and what you do inside it determines everything.

Haggai and Jerry go deep into:

Why uncertainty—not risk—is the raw material of billion-dollar startups
How Google, Facebook, Uber, and Datadog exploited moments incumbents couldn’t model
The investor’s job: identify the unknowable, not the comfortable
The founder’s job: make the idea bigger—big enough to scare you
Why valuation math is a fantasy (and when walking backwards actually helps)
The emotional violence of building: ego, failure, board politics, and being pushed out of your own company
How to separate your identity from your startup—without losing your nerve
AI as the final stage of the computing wave (and why most AI startups won’t capture the value)
Why entrepreneurship is ultimately the purest expression of human agency

If you’re a founder wrestling with conviction, an investor sharpening your judgment, or someone who wants to understand how innovation actually moves societies—this conversation is for you.