20VC: a16z Raises $10BN in New Funds | Mercor Raises $350M at a $10BN Valuation | OpenAI Restructuring: Who Wins and Who Loses | Why IRR is a BS Metric and Three Ways to Win in VC Today artwork

20VC: a16z Raises $10BN in New Funds | Mercor Raises $350M at a $10BN Valuation | OpenAI Restructuring: Who Wins and Who Loses | Why IRR is a BS Metric and Three Ways to Win in VC Today

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

October 30, 2025

AGENDA: 05:17 OpenAI's Restructuring: Winners and Losers 17:17 Andreessen Horowitz's Raise $10BN in New Funds 26:38 Mercor Raises $350M at a $10BN Valuation 43:08 Spray and Pray: Does it Work: Data Breakdown 47:04 The Role of Option Checks Venture Capital 48:36 The Three Ways to Win in VC...
Speakers: Jason Calacanis, Rory O'Driscoll, Harry Stebbings
**Jason Calacanis** (0:00)
I just can't think of a retail IPO that would be more popular than OpenAI. To me, going from 23 billion to 30 billion, I don't even consider it an upround. It's not enough.

**Rory O'Driscoll** (0:10)
If they really have gone from 100 to 150 in less than six months, then I can make this conversation really quick. There's no way they should sell. Andreessen Horowitz is the red army of the venture industry. What you're basically saying is, Rory, you can win a deal, not because I've grafted for 30 years and returned, frankly, billions of dollars to my investors, but because I'm on a fucking pod. If that sentence is true, if that sentence isn't true, then a 100% Mark Andreessen was right all along.

**Jason Calacanis** (0:36)
I think Bezos would lay off half his company and in a fortnight, it was the right thing. I don't even care.

**Harry Stebbings** (0:41)
Andreessen Horowitz is the red army of the venture industry. I think that has to be the quote of this series. This is my favorite show of the week. How can you not listen to that intro and just be like, I want to listen to this show. This episode was so much fun to do.
We cover everything from OpenAI's structuring to Synthesia Rejecting The Round, to Ramp's New Potential Round, to many, many more. This was so much fun to do. I want to hear your feedback on the show, harry at 20vc.com. But before we dive into the show today, now most people who get scammed never talk about it. And if it can happen to tech savvy professionals, CEOs and investors, it can happen to anyone. But the problem isn't just losing money. It's that today's scams, they're built differently for a very new world. One where AI can generate convincing messages in seconds, and fake sites look more like real sites than the real thing. Traditional tools were not built for this future. And that's why Guardio exists. Guardio is this incredible predictive and proactive engine. It leverages advanced AI threat detection to block highly targeted, socially engineered scams before they ever reach you. From phishing emails and fake login pages to financial fraud, Guardio protects you across the ways people actually live and work online. And security shouldn't be complicated. Guardio continuously monitors across all your accounts and devices, uncovering risks in real time, and guiding you to close gaps before attackers exploit them. Trusted by over a million users, Guardio is setting the new standard for personal cybersecurity.
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