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Harry Stebbings

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. 

If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.

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

AGENDA:
 
00:00 - SpaceX Completes Acquisition of xAI in $1.25 Trillion Merger
 
08:44 - The Rehabilitation of the IPO and the End of "State Private Forever"
 
15:53 - The 2026 SaaS Massacre: Public Market Collapse 
 
31:20 - Next-Gen CRM War: Hubspot Down 50%+ vs Next Gen Heavily Funded
 
45:30 - Microsoft's $360 Billion Market Cap Loss and the Shift in AI Narrative
 
52:45 - Nvidia's Strategic Retreat: The Dispute Over the $100 Billion OpenAI Investment
 
01:03:30 - Waymo Raises $16 Billion at a $110 Billion Valuation
 
01:17:30 - The Launch of OpenClaw and Moltbook: 1.5 Million Agents Join a Social Network

20VC: SpaceX Completes Acquisition of xAI | The 2026 SaaS Massacre: Public Market Collapse | Microsoft's $360 Billion Market Cap Loss | NVIDIA's $100BN Investment Dispute with OpenAI | Waymo Raises $16 Billion at a $110 Billion Valuation

Oren Zeev is one of the most prominent solo capitalists in venture. He is one of the most no BS investors of our time. Oren manages over $1BN in AUM and is known for his "radical alignment" approach, often taking $0 in management fees. His track record includes massive successes like Navan, Audible, and Houzz.
 
AGENDA:
 
03:11 – Why the Best Investments Always Look "Wrong" at the Start
 
05:58 – The AI Tsunami: How to Spot Beneficiaries vs. Victims
 
10:43 – The Death of Incumbents? Why Most AI Predictions Are Wrong
 
14:12 – Why Chasing Hyper-Growth is a "Disaster Waiting to Happen"
 
19:41 – The Biggest Mistakes From 2021 and Investing Lessons From It?
 
25:52 – Is the Future of Venture Boutique or Mega Fund: Does the Middle Die?
 
32:00 – The Great VC Shakeout: Why 50% of Funds Will Slowly Die
 
38:52 – Why Oren Zeev Takes $0 in Management Fees
 
50:48 – Why VCs Should Never Tell Their LPs What They Are Doing?
 
59:11 – How I Missed Investing in Facebook and Lessons Learned

20VC: 50% of Funds Will Go Out of Business | Why Growth Expectations Today are BS and Will Not Last | Why Oren Zeev Takes $0 Management Fees But 30% Carry | Why GPs Should Not Tell LPs Their Strategy

Omer Shai serves as the CMO at Wix. Shai leads a team of over 400 people and is responsible for the company's global online and offline marketing activity, which boasts an incredible growth of approximately 3 million new users every month. Under Shai, the marketing department has executed hundreds of worldwide campaigns for television and social including 5 Super Bowl commercials, creative videos, podcasts and more.
 
AGENDA:
 
00:00 — The AI Agent Revolution: 93% Automation?
 
03:55 — Why I'm Buying TWO Super Bowl Ads This Year
 
08:58 — The $100M Marketing Secret: Brand vs. Performance
 
13:28 — Why LTV is Bullshit (and What You Should Use Instead)
 
18:52 — 10x Your Growth: How to Find Tomorrow's Arbitrage
 
27:10 — SEO is Dying? Why I'm Increasing My Ad Spend Anyway
 
31:14 — The TikTok Fail: Why Even Big Brands Can't Crack It
 
36:11 — Stop Selling the "Why": Put the Product in the Center
 
47:57 — Will AI Make You Unemployed? A Warning for Marketers
 
52:27 — Why Celebrity Endorsements Never Work

20Growth: How Wix Built a $100M Marketing Machine | Why LTV is BS and Why Time Return On Investment is the Most Important Metric | How to 10x Your Growth: What is the Next Great Channel with Omer Shai, CMO @ Wix

AGENDA:
 
03:36 Brex Acquisition by Capital One for $5.15BN
 
10:54 Does Brex's Acquisition Help or Hurt Ramp?
 
16:28 TikTok Deal Completed: Who Won & Who Lost: Analysis
 
19:30 Anthropic Inference Costs Higher Than Expected
 
37:50 Open Evidence Raises at $12BN from Thrive and DST
 
53:56 Wealthront IPO Disaster: Is $1.5BN IPO Too Small?
 
01:07:27 Salesforce Wins $5BN Army Contract: The Last Laugh for SaaS

20VC: Brex Acquired for $5.15BN | a16z Companies are 2/3 AI Revenues | Anthropic Inference Costs Skyrocket | OpenEvidence Raises at $12BN Valuation | The IPO Market: EquipmentShare, Wealthfront and Ethos Insurance

Max Junestrand is the Co-Founder and CEO @ Legora, the legal AI company that has scaled to 750 of the world's leading law firms as customers and over 300 employees in just 2 years. They have raised over $200M from some of the best in the business including Benchmark, General Catalyst, Redpoint and ICONIQ. 
 
AGENDA:
 
04:16 Why Does Everyone Think Harvey When They Hear Legal AI?
 
07:35 Why OpenAI is Toast? Switching to Anthropic!
 
11:47 24 Months: Which Foundation Models Will Win? 
 
23:53 Lessons Scaling from Europe into the US
 
28:53 Do Americans Work As Hard As They Say?
 
32:20 Why Seat Models Are Not Dead in SaaS?
 
36:17 How to Use Competition To Drive a Fire in Your Team?
 
40:59 Is Legal AI a Winner-Take-All Market? How Does It End?
 
47:18 The Future of Law Firms: Do Juniors Get Fired?
 
53:19 How We Raised $200M and 3 Rounds with No Deck
 
57:21 Quickfire Round: Best Advice, Closest Mentor, Biggest Mindset Shift

20VC: From Only OpenAI to Die-Hard Anthropic: The Downfall of OpenAI in Enterprise | Harvey vs Legora: Legal AI is a Winner Take All | $7M ARR in a Single Day and Raising $200M Across 3 Rounds with No Deck with Max Junestrand, CEO @ Legora

AGENDA:
 
00:03:00 – Harry's Wild Start: Making £1.75M at 19 in 36 Hours
 
00:06:00 – How Harry Got Marc Benioff on 20VC with Cold Emailing Alone
 
00:07:30 – Raising $70M on WhatsApp – Relationship Building Secrets
 
00:12:00 – Decision Framework: What Would Pat Grady (Sequoia) Do?
 
00:15:00 – Chase Your First Million – It Unlocks Everything
 
00:16:30 – Advice for 19-Year-Olds Today: Niche Down, Interview Leaders, Publish
 
00:18:00 – University Is a Waste for Most | Leverage Youth & Risk
 
00:22:30 – How Getting Kicked Out of School Changed Everything
 
00:30:00 – Why Should Everyone Be Creating Content Today and How to Start
 
00:35:30 – 7 Lessons from Billionaires
 
 • 

00:36:00 – #1: Never Accept No (The $12M Turnaround Story)
 • 
 • 

00:37:30 – #2: Beat Down the Door (53 Emails to Marc Benioff)
 • 
 • 

00:39:00 – #3: Just Start – 99% Never Do
 • 
 • 

00:40:30 – #4: Use a Role Model Framework for Hard Decisions
 • 
 • 

00:42:00 – #5: Chasing Money Won't Make You Happy – Enjoy the Art
 • 
 • 

00:44:00 – #6: Break Big Visions into Achievable Milestones
 • 
 • 

00:45:30 – #7: Win Over the Partner (Power of Pillow Talk)
 •

20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)

Chad Peets is one of the great sales leaders of our time. Previously, he was the sales saviour at Snowflake and was an advisor to the CEO there. He was also an MD at Sutter Hill where he sat on the board of companies like Sigma Computing and Augment Code. 
 
AGENDA:
 
04:53 How to Recruit the Best Sales Talent Today 
 
06:27 Why Europe is a Nightmare for Recruitment in Sales
 
11:29 How to Evaluate Sales Talent: Green and Red Flags
 
21:58 Why Remote Work is BS and You Have to be in Office
 
23:43 How to Improve Sales Team Performance in Just 24 Hours
 
27:45 When to Fire vs When to Give More Time
 
32:10 How to Set Sales Quotas Effectively
 
34:39 Adjusting Compensation Plans for Better Performance
 
37:50 Why Work Life Balance is Total BS
 
41:08 Biggest Lessons on Leading Sales Teams
 
50:37 What is The Future of Enterprise Sales with AI
 
58:40 Quick Fire Questions and Final Thoughts

20Sales: Why the Best Sales People are F***** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets

AGENDA:
 
03:30 Can VC Survive With Public Market Prices Today
 
15:20 The Implosion of Thinking Machines
 
21:13 Elon Musk vs. OpenAI: The Legal Battle
 
40:50 Can OpenAI Win Ads?
 
55:50 ClickHouse's $15BN Deal: Analysed
 
58:55 Replit's $9BN Deal: Analysed
 
01:08:35 There Are Only Two Types of Deals VCs Want To Do Today

20VC: Sam Altman vs Elon Musk: The $100BN Battle | The Implosion of Thinking Machines | Can VC Survive Public Market Pricing Today? | ClickHouse and Replit's New Rounds: Analysed

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

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

Noam Lovinsky is the CPO @ Superhuman (formerly Grammarly). Prior to Superhuman he was a Senior Director of Product Management at Facebook. In his earlier years, he was CPO @ Thumbtack and spent 5 years as a Director of Product Management at Google where he was responsible for all of Youtube's applications. 
 
AGENDA:
 
03:43 What is Great Product Leadership in a World of AI
 
07:45 Does the Design Phase Die in a World of Vibe Coding
 
12:21 How AI Changes Product Development Most
 
22:23 Accelerating Product Development
 
29:32 AI's Impact on Product Building
 
34:19 Predictions for 2026
 
34:45 Quick Fire Round
 
38:41 Reflections and Future Plans

20Product: Is the Design Phase Dead in a World of AI | Has Claude Code Crushed Anthropic Already | What Roles of a PM Are Less and More Important with AI | How the Best Product Leaders Tell Stories with Noam Lovinsky, CPO @ Superhuman

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

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