20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg artwork

20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

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

January 19, 2026

Winston Weinberg is the CEO and Co-Founder of Harvey, the leading professional services platform engineered with AI for law, tax, and finance. Winston has raised over $980M for Harvey from Sequoia, a16z, GV, Elad Gil and more with a last round price of $9.2BN post-money.
Speakers: Winston Weinberg, Harry Stebbings
**Winston Weinberg** (0:00)
I think the value of B2B SaaS is about to become astronomical. I think that we're seeing a plateau in performance for consumer use cases. Probably what's gonna happen is the economy is gonna explode. I think a lot of people in deals, they think that movement is action. Not true. The second piece is know when to not negotiate. There are certain deals where you want one thing from the deal and nothing else matters. If you wanna hire somebody, hire them whatever they want to be hired and put them in the position that they want.

**Harry Stebbings** (0:32)
This is 20VC with me, Harry Stebbings, and I'm so excited for the show today. So I've been sitting back watching the legal AI space really in awe, specifically at the speed with which these companies are growing. And today we have the front runner, Harvey. They announced last week they hit 190 million in annual recurring revenue, 500 team members, over a thousand customers. The scaling is unprecedented. And today, I sit down with their co-founder and CEO, Winston Weinberg. But before we dive into the show today, as an investor, I'm always on the lookout for tools that really transform how I work, tools that don't just save time but fundamentally change how I uncover insights. That's exactly what AlphaSense does. With the acquisition of Tegas, AlphaSense is now the ultimate research platform built for professionals who need insights they can trust, fast. I've used Tegas before for company deep dives right here on the podcast. It's been an incredible resource for expert insights. But now with AlphaSense leading the way, it combines those insights with premium content, top broker research and cutting edge generative AI. The result, a platform that works like a supercharged junior analyst, delivering trusted insights and analysis on demand. AlphaSense has completely reimagined fundamental research, helping you uncover opportunities from perspectives you didn't even know how they existed. It's faster, it's smarter, and it's built to give you the edge in every decision you make. Twenty VC listeners don't miss your chance to try AlphaSense for free. Visit alphasense.com/twozero to unlock your trial. That's alphasense.com/twozero.
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**Winston Weinberg** (4:21)
You have now arrived at your destination.

**Harry Stebbings** (4:24)
Winston, dude, it is so good to finally meet in person. It's so great to have you in the studio. I've heard many great things for a while because it was Sarah Guo that found you first, before Pat, I heard.

**Winston Weinberg** (4:36)
I know, if Pat's listening, he definitely needs to give some credit to Sarah here. Yeah, Sarah actually was our first investor was OpenAI, and then our first two angel investors were Sarah Guo and Elad Gil.

**Harry Stebbings** (4:48)
One, I love the way that under 30 seconds, we've already done a sucker punch to Pat. But two, I just want to start on something that shows a little bit about your character. It was a story that Pat told me. He said, ask him about running a mile, the time that he did it first and how that progressed, because it's very revealing of his character.

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