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

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.

Whether you’re a founder, investor, LP or operator in Web3, this conversation provides:

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

VNTR is building the world’s largest investor community by sharing lessons, hosting events, and offering opportunities. Active VC investors can join by claiming a free investor account at https://app.vntr.vc/

Timestamps:

00:00 Intro

01:02 Welcome Michael Terpin

02:40 Angel Investing with Equity Compensation: Wins, Losses, and a 100x Return

09:13 Early Money Is the Most Expensive Money

14:43 Bitcoin Cycles vs. Altcoin Narratives: A Decade of Patterns

24:13 The Token Flood Problem

26:09 Visionary Founder + AI-Enhanced Coder

29:46 The New Token Reality: Why Most Web3 Projects Need Equity

36:58 Why Banking Will Shrink When Stablecoins Scale

40:20 Stablecoins as Payments: Why Banks Don’t Need Circle or Tether

41:43 GBTC, Premiums, Discounts and the Birth of DATs

46:44 The DAT Bubble: Overvaluations and Regulation

50:50 The Power of Community-Led Deal Flow

53:43 Deal Flow, Community, and the Birth of CoinAgenda

59:16 The Four Seasons of Bitcoin

01:11:24 Supply Shock, Capitulation & the Long Game

01:16:30 Personal Passions: Reading, Lifting & Collecting Wine

🔹 VNTR Website: https://app.vntr.vc/

🔹 VNTR Instagram: https://www.instagram.com/vntrcapital/

🔹 VNTR Linkedin: https://www.linkedin.com/company/vntrcap/

Host:

Yuri G. Rabinovich

https://www.linkedin.com/in/byuric/

Guest:

Michael Terpin

https://www.linkedin.com/in/michaelterpin/