Bet on yourself. Don't be someone's option bet.
In this solo episode of Very True, Alex talks about how venture math actually works and why it looks completely different depending on your fund size, the stage you invest at, and the company you are building.
Over the last few years, the venture market has gotten increasingly distorted. Between massive headline valuations, intense liquidation preferences, and a setup where VCs can get rich purely on guaranteed management fees, founders are frequently pushed into a moon or bust game. Even if you build a great company with real technology and real revenue, you can easily wind up walking away from a successful mid-market acquisition with nothing.
Alex breaks down the financial friction between early-stage and late-stage investing, why paper wealth metrics like MOIC are misleading, and why founders need a clean secondary strategy to protect their equity. It all comes down to one question: Are you running your own option bet, or are you somebody else’s?
Episode Highlights:
The management fee game. How venture capital mechanics can misalign a VC’s incentives with a founder’s outcome, allowing partners to build massive wealth on fees regardless of fund performance.
Clean slates vs recaps. A look at why the market aggressively floods money into unproven startups while leaving existing, operationally solid companies stranded if they carry historical valuation baggage.
The entry valuation trap. A breakdown of how over-paying on entry valuation or over-raising downstream triggers brutal liquidation preferences that wipe out founders and early seed investors at exit.
MOIC vs DPI. The critical difference between parading paper wealth and waiting for cold hard cash to hit the bank, and why great early-stage managers care about returning realized capital.
Running your own option bet. Why optimizing the middle path of $50M to $250M exits, focusing on sustainable revenue growth, and leveraging early secondary sales is the real playbook for building true generational wealth.
Links & Resources:
Medium Essay: https://medium.com/@Alexoppenheimer/are-recent-valuation-hits-as-unreasonable-as-they-seem-88f5ae789e92
LinkedIn Essay: https://www.linkedin.com/pulse/how-mess-up-good-company-make-any-money-along-way-alex-oppenheimer/
Verissimo Ventures: https://verissimo.vc/
About Very True:
Hosted by Alex, Very True by Verissimo Ventures explores the honest, unvarnished stories of founders and the real problems they are solving. We look past the hype to find the truth in technology and entrepreneurship.
Creators and Guests
