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

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

Author: Harry Stebbings January 19, 2026 Duration: 1:13:53
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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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

 


Hosted by Harry Stebbings, The Twenty Minute VC (20VC) pulls back the curtain on the high-stakes worlds of venture capital and startup building. Each episode is a compact, twenty-minute dive into the minds shaping the future of technology. You’ll hear candid conversations with legendary investors, the very individuals who fund and guide the next generation of companies, featuring voices like Sequoia's Doug Leone and Benchmark's Bill Gurley. Beyond the capital, this podcast dedicates time to the founders themselves. Weekly, Stebbings sits down with transformative entrepreneurs such as Spotify's Daniel Ek, LinkedIn's Reid Hoffman, and Snowflake's Frank Slootman, unpacking the real journeys behind their iconic companies. The format is direct and focused, cutting straight to the core insights on funding strategies, pitch dynamics, and the personal philosophies that drive success. Tuning into this podcast means gaining an unfiltered perspective from both sides of the table, all delivered in a concise and accessible style that fits into your day.
Author: Language: English Episodes: 100

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The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Podcast Episodes
20VC: Base44's Maor Shlomo on How Vibe Coding Will Kill SaaS and Salesforce | Why it is BS that Vibe Coding Platforms Do Not Have Defensibility and Bad Margins | Why He Worries About Google, Not Replit and Lovable | Why Long Anthropic, Not OpenAI? [not-audio_url] [/not-audio_url]

Duration: 1:11:43
Maor Shlomo is the Founder and CEO of Base44, the AI building platform that Maor built from idea to $80M acquisition by Wix, in just 8 months. Today the company serves millions of users and will hit $50M ARR by the end o…
20VC: Cursor Raises $2.3BN: Who Wins the Coding War | Peter Thiel and Softbank Sell NVIDIA: Analysed | Why Venture Capital Will Hit $1TRN and the Opening of Retail | Why Stripe and the Best Companies Will Never Go Public [not-audio_url] [/not-audio_url]

Duration: 1:22:38
AGENDA: 04:47 Cursor Raises $2.3BN at $29BN Valuation 11:36 What Gemini 3 Means for Lovable, Cursor and Replit 30:54 Peter Thiel and Softbank Sell NVIDIA: The Bubble Bursting? 48:54 Oracle Credit Default Swaps: The Risk…
20VC: Andrew NG on The Biggest Bottlenecks in AI | How LLMs Can Be Used as a Geopolitical Weapon | Do Margins Matter in a World of AI? | Is Defensibility Dead in a World of AI? | Will AI Deliver Masa Son's Predictions of 5% GDP Growth? [not-audio_url] [/not-audio_url]

Duration: 1:02:53
Dr. Andrew Ng is a globally recognized leader in AI. He is Founder of DeepLearning.AI, Executive Chairman of LandingAI, General Partner at AI Fund, Chairman and Co-Founder of Coursera. As a pioneer in machine learning An…
20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid [not-audio_url] [/not-audio_url]

Duration: 1:25:43
Ev Randle is a General Partner @ Benchmark, one of the best funds in venture capital. In their latest fund, they have Mercor ($10BN valuation), Sierra ($10BN valuation), Firework ($4BN valuation), Legora ($2Bn valuation)…
20VC: Cohere's Chief AI Officer on Why Scaling Laws Will Continue | Whether You Can Buy Success in AI with Talent Acquisitions | The Future of Synthetic Data & What It Means for Models | Why AI Coding is Akin to Image Generation in 2015 with Joelle Pineau [not-audio_url] [/not-audio_url]

Duration: 57:34
Joelle Pineau is the Chief AI Officer at Cohere, where she leads research on advancing large language models and practical AI systems. Before joining Cohere, she was VP of AI Research at Meta, where she founded and led M…

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