Harvey CEO Winston Weinberg: How to Make Mega Deals | Lessons from Rabois, Halligan & Grady

ℹ️ EPISODE INFO

Released

January 19, 2026

Duration

1h 13m

Channel

The Twenty Minute VC

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

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. ----------------------------------------------- Timestamps: 00:00 Intro 04:16 #1 Thing Every Founder Needs to Do Everyday 13:35 Why VCs Suck at Helping Companies Hire? 15:26 How to Get Sequoia and a16z Term Sheets 25:49 What No One Understands About Enterprise AI Adoption 38:21 AI's Impact on Professional Services 39:14 Future of Law Firms: Do They Die? 43:17 What Everyone Should Know That No One Tells You About Hiring in Europe 48:54 I Have Massive Trust Issues… 55:55 Biggest Lessons on Effective Deal-Making 01:01:30 Cold Emailing OpenAI and It Leading to a Term Sheet 01:05:10 Quick Fire Round ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on X: https://twitter.com/HarryStebbings Follow Winston Weinberg on X: https://twitter.com/winstonweinberg Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #winstonweinberg #ceo #keithrabois #aiadoption #founderadvice #patgrady

🎤 SPEAKERS

• Winston Weinberg

  guest

• Harry Stebbings

  host

🧾 EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Winston Weinberg and Harry Stebbings, Harvey CEO Winston Weinberg: How to Make Mega Deals | Lessons from Rabois, Halligan & Grady explores harvey CEO on scaling AI SaaS, enterprise adoption, mega-deal strategy Weinberg argues B2B SaaS value is set to become “astronomical” as AI drives massive ROI and spend shifts from human labor and professional services to software.

🔗 RELATED EPISODES

Inside Legora: Jude Law Generated $50M Pipeline | Are They Undervalued at $5.5BN? | Patrick Forquer

Cliff Weitzman: What I Learned from 100 of the World’s Top CEOs & Why Tokens Will Outspend Salaries

Shopify CEO on How AI is a Scapegoat for Mass Layoffs & Trump Derangement Syndrome in Canada

Inside Clay's Sales Playbook | Becca Lindquist

Jackie Reses: The Most Powerful Woman in Finance; Making $50BN for Yahoo on Alibaba | E996

Tom Hulme & Stan Boland: Lessons from Jensen Huang & How to Fix the UK Tech Ecosystem