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

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

The Twenty Minute VC

Business, Investing, Tech News, News

4.4693 Ratings

🗓️ 19 January 2026

⏱️ 74 minutes

🧾️ Download transcript

Summary

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. Before founding Harvey in August 2022, Winston was an attorney at O'Melveny & Myers LLP, specializing in antitrust and securities litigation. 

AGENDA:

04:10 #1 Thing Every Founder Needs to Do Everyday

05:33 Must Do Daily Routines and Productivity Tips for CEOs

12:45 How to Get Sequoia and a16z Term Sheets

15:06 Why VCs Suck at Helping Companies Hire?

27:01 What No One Understands About Enterprise AI Adoption

38:06 AI's Impact on Professional Services

39:26 Future of Law Firms: Do They Die?

43:38 What Everyone Should Know That No One Tells You About Hiring in Europe

47:08 I Have Massive Trust Issues…

54:17 Biggest Lessons on Effective Deal-Making 

59:20 Cold Emailing OpenAI and It Leading to a Term Sheet

01:02:33 Quick Fire Round

Try NEXOS.AI for yourself with a 14-day free trial: https://nexos.ai/20vc

 

Transcript

Click on a timestamp to play from that location

0:00.0

I think the value of B2B SaaS is about to become astronomical.

0:04.7

I think that we're seeing a plateau in performance for consumer use cases.

0:08.5

Probably what's going to happen is the economy is going to explode.

0:11.0

I think a lot of people in deals, they think that movement is action.

0:16.3

Not true.

0:16.9

The second piece is know when to not negotiate.

0:23.4

There are certain deals where you want one thing from the deal and nothing else matters. If you want to hire somebody, hire them, whatever they

0:29.7

want to be hired, and put them in the position that they want. This is 20 VC with me, Harry Stubbings,

0:34.6

and I'm so excited for the show's day. So I've been sitting back watching the legal AI space really in awe, specifically at the speed with which these companies

0:43.1

are growing. And today we have the frontrunner, Harvey. They announced last week they hit

0:47.7

190 million in annual recurring revenue, 500 team members, over 1 thousand customers, the scaling is unprecedented.

0:56.0

And today I sit down with their co-found and CEO, Winston Weinberg.

1:00.0

But before we dive into the show today, as an investor, I'm always on the lookout for tools

1:04.0

that really transform how I work, tools that don't just save time but fundamentally change how I uncover insights.

1:10.0

That's exactly what AlphaSense does.

1:11.9

With the acquisition of Tegas, AlphaSense is now the ultimate research platform built for

1:16.6

professionals who need insights they can trust fast. I've used Teegas before for company deep dives

1:22.6

right here on the podcast. It's been an incredible resource for expert insights. But now with

1:26.8

AlphaSense leading the way,

1:28.8

it combines those insights with premium content, top broker research and cutting edge generative

1:34.0

AI. The result? A platform that works like a supercharged junior analyst delivering trusted

1:39.2

insights and analysis on demand. AlphaSense has completely reimagined fundamental research, helping you uncover

...

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