How to Win in Web3: Cycles, Tokens, Traction | Michael Terpin

About this episode

In this episode of the VNTR Podcast, we sit down with legendary crypto investor and industry pioneer Michael Terpin to break down one of the most misunderstood forces in the digital asset market — the 4-year Bitcoin supercycle.

With 30+ years in tech, a Sequoia-backed exit, early investments in Ethereum and Tether, and a decade building crypto communities and conferences, Michael brings a rare combination of historical context, data, narrative intuition, and cycle theory.

This conversation goes far beyond price predictions — it reveals how the structure of Bitcoin itself shapes market behavior and why, cycle after cycle, most investors still get it wrong.

What you’ll learn

• Clear frameworks
• Real cycle data
• Hard-won investor lessons
• Insider perspective on trends shaping 2025 and beyond

Chapters

1. 00:00Intro
2. 01:02Welcome Michael Terpin
3. 02:40Angel Investing with Equity Compensation: Wins, Losses, and a 100x Return
4. 09:13Early Money Is the Most Expensive Money
5. 14:43Bitcoin Cycles vs. Altcoin Narratives: A Decade of Patterns
6. 24:13The Token Flood Problem
7. 26:09Visionary Founder + AI-Enhanced Coder
8. 29:46The New Token Reality: Why Most Web3 Projects Need Equity
9. 36:58Why Banking Will Shrink When Stablecoins Scale
10. 40:20Stablecoins as Payments: Why Banks Don’t Need Circle or Tether
11. 41:43GBTC, Premiums, Discounts and the Birth of DATs
12. 46:44The DAT Bubble: Overvaluations and Regulation
13. 50:50The Power of Community-Led Deal Flow
14. 53:43Deal Flow, Community, and the Birth of CoinAgenda
15. 59:16The Four Seasons of Bitcoin
16. 1:11:24Supply Shock, Capitulation & the Long Game
17. 1:16:30Personal Passions: Reading, Lifting & Collecting Wine