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 startupsHow Google, Facebook, Uber, and Datadog exploited moments incumbents couldn’t modelThe investor’s job: identify the unknowable, not the comfortableThe founder’s job: make the idea bigger—big enough to scare youWhy 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 companyHow to separate your identity from your startup—without losing your nerveAI 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 agencyIf 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: 👉 https://aggaeus.com CONNECT WITH JERRY NEUMANN LinkedIn Reaction Wheel Book – Founder vs Investor CONNECT WITH HAGGAI LinkedIn FOLLOW AGGAEUS Instagram TikTok YouTube SUBSCRIBE TO THE PODCAST Substack Apple Podcasts SPONSORS Kardz.Biz — “A business card too good to give away.” INQUIRIES 💼 Sponsorships / Business: talktous@aggaeus.com 🎙 Podcast: DM via Instagram Some links may earn affiliate commissions. Offers, terms, and availability may change without notice. Aggaeus content is for informational and educational purposes only and should not be considered legal, business, investment, or tax advice. You should conduct your own research and consult qualified professionals before making any decisions. We may feature companies, products, or entities in which Aggaeus, its affiliates, or the author have invested or may invest, or with which they have had, have, or may have a financial, professional, or other relationship.
