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:
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.
Check out the full episode notes, transcripts, and all links on Substack:
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