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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

John McMahon is widely regarded as one of the greatest enterprise-software sales leaders of all time. He's the only person to have served as Chief Revenue Officer at five public software companies: PTC, GeoTel, Ariba, BladeLogic and BMC Software. He helped scale BladeLogic from a startup into a public company — ultimately leading to its ~$880M sale to BMC — and drove GeoTel into a multi-billion dollar acquisition. Today he sits on the boards of top names such as Snowflake and MongoDB, while also mentoring and influencing a who's-who of modern SaaS sales leaders.
 
AGENDA:
 
03:33 The Art and Science of Sales: Insights from a Veteran
 
04:29 Adapting Sales Strategies in the Age of AI and PLG
 
07:47 The Ultimate Framework to do Deal Qualification
 
14:13 How to Drive Urgency and Maintain Sales Process
 
20:06 How to Hire the Best Sales Reps
 
25:11 Step-by-Step Guide to Training Sales Reps
 
45:22 The Mindset of the Best Sales Reps
 
54:55 Single Most Important Skill to Win in Sales

20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

AGENDA:
 
04:06 Anthropic's $30BN Investment from Microsoft and NVIDIA
 
07:01 Google vs. OpenAI: Sam Altman's "War Mode" Memo
 
15:27 NVIDIA's Customer Concentration: Bull or Bear
 
22:12 Is "War Mode" BS: Does Hyper-Aggressive Ever Work?
 
36:12 Sierra Hits $100M ARR: Justify $10BN Price?
 
46:14 Implementation is the Biggest Barrier to Enterprise AI Growth
 
01:04:04 Is LLM Search Optimisation (GEO) Selling Snake Oil? What AI is a Fraud vs Real?
 
01:14:27 Figma Market Cap: Is the IPO Market F****** for 2026

20VC: Anthropic Raises $30BN from Microsoft and NVIDIA | NVIDIA Core Business Threatened by TPU | Sam Altman's "War Mode" Analysed | Sierra Hits $100M ARR: Justifies $10BN Price? | Lovable Hits $200M ARR & Rumoured $6BN Round

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 of the year. Before Base44, Maor was the Co-Founder and CTO of Explorium.
 
AGENDA:
 
00:05 – 00:10: How Vibe Coding is Going to Kill Salesforce and SaaS
 

 
00:13 – 00:15: Do Vibe Coding platforms have any defensibility?
 

 
00:22 – 00:24: I am not worried about Replit and Lovable, I am worried about Google…
 

 
00:28 – 00:29: Margins do not matter, the price of the models will go to zero
 

 
00:31 – 00:32: Speed to copy has never been lower; has the technical moat been eroded?
 

 
00:47 – 00:48: How does Base44 beat Cursor?
 

 
00:56 – 00:57: Do not pay attention to competition: focus on your business
 

 
00:57 – 00:58: How Base44 is helped, not hurt by not being in Silicon Valley?
 

 
00:58 – 00:59: What percent of code will be written by AI in 12 months?
 

 
01:01 – 01:02: OpenAI or Anthropic: Why Maor is Long Anthropic?
 

 
01:03 – 01:04: If I could have any board member in the world it would be Jack Dorsey

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?

Max Altman is Co‑Founder & Managing Partner at Saga Ventures, a US$125 M early‑stage fund. Before Saga Max was an investor with Apollo Projects, Hydrazine Capital and Altman Capital (where he helped deploy over US$500 M) into breakout names such as Rippling and Reddit.
 
AGENDA:
 
03:55 – Venture Capital Is FULL of Tourists With Single-Digit IQs
 
06:20 – Inside the Madness of Parker Conrad: Genius, Chaos, and WTF Emails
 
10:35 – The Rippling Deal That Changed Everything
 
12:40 – Living in Sam Altman's Shadow: The Confession
 
17:30 – $200M Fund Mistakes: Max's Brutal Lessons From Hydrazine
 
22:05 – The $2B Reddit Return… and the $2B Left on the Table
 
25:00 – Why Climate Tech Is a Total VC Mirage
 
28:40 – The New Seed War: Can Anyone Survive Sequoia & Andreessen?
 
46:55 – Max's Boldest Predictions

20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster

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 is Increasing
 
01:07:22 Stripe Does Tender at All-Time High: Why the Best Companies Will Never IPO
 
01:19:18 Why Retail WIll Cause a Surge of Capital into VC Funds

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

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 Andrew has authored or co-authored over 200 research papers in machine learning, robotics and related fields. In 2023, he was named to the Time100 AI list of the most influential AI persons in the world.
 
Agenda:
 
03:19 What are the Biggest Bottlenecks in AI Today? 
 
08:51 How LLMs Can Be Used as a Geopolitical Weapon
 
15:48 Should AI Talent Really Be Paid Billions?
 
29:07 Why is the Application Layer the Most Exciting Layer?
 
36:22 Do Margins Matter in a World of AI?
 
38:02 Is Defensibility Dead in a World of AI?
 
45:29 Will AI Deliver Masa Son's Predictions of 5% GDP Growth?
 
49:39 Are We in an AI Bubble?
 
57:31 Will Human Labour Budgets Shift to AI Spend?

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?

Carl Rivera is the Chief Design Officer at Shopify, where he previously led both Merchant Services and the Shop App as VP of Product. Before joining Shopify through its acquisition of Tictail, Carl was the co-founder and CEO of Tictail, the "Tumblr for e-commerce," where he built one of the most beloved design-forward commerce platforms of its era.
 
AGENDA:
 
05:05 Biggest Lessons from Selling My Company to Shopify
 
09:55 Where Does Shopify Suck at Product: Lessons from that?
 
17:37 What makes Truly Great product Design: The Five Pillars
 
31:02 The Future of Design in an AI-Driven World
 
36:00 Do We Skip the Design Phase in AI: Figma's Evolving Role in Design
 
40:09 Remote Work vs. In-Person Collaboration: Where Remote Loses?
 
42:43 What Happens to the Vibe Coding Market
 
47:06 Product Management and Team Dynamics
 
59:48 Does AI Favour Incumbents or Startups

20Product: How AI Changes Product Design | Does the Design Phase Become Irrelevant in a World of Vibe Coding | The Five Pillars of Truly Great Product Design with Carl Rivera, Chief Design Officer at Shopify

AGENDA:
 
04:22 Sequoia's Leadership Transition
 
09:46 Michael Burry's Big Short on Nvidia and Palantir
 
17:41 Gamma Raises $100M at a $2BN Valuation
 
32:34 Does Defensibility Exist Today When Copying is Easy
 
40:31 Should All Funds Be Way More Diversified
 
47:12 How to Run a Fundraising Process & What Not To Do
 
57:57 Datadog Surges 20% and Duolingo Crashes: What Happened

20VC: Sequoia's Leadership Transition | Michael Burry Shorts NVIDIA and Palantir | Gamma Raises $100M at $2BN | Has Defensibility Died in a World of AI | Datadog Surges as Duolingo Plummets: What is Happening

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) and Langchain ($1.4Bn valuation). To put this in multiples on invested capital, that is a 60x, two 30x and two 20x. Before Benchmark, Ev was a Partner @ Kleiner Perkins and before Kleiner, Ev was an investor at Founders Fund and Bond. 
 
AGENDA:
 
05:25 Biggest Investing Lessons from Peter Thiel, Mary Meeker and Mamoon Hamid
 
14:36 OpenAI Will Be a $TRN Company & OpenAI or Anthropic: Who Wins Coding?
 
22:27 Why We Should Not Focus on Margin But Gross Dollar Per Customer
 
30:25 Why AI Labs are the Biggest Threat to AI App Companies
 
44:26 Do Benchmark Fire Founders? If so… Truly the Best Partner?
 
54:38 People, Product, Market: Rank 1-3 and Why?
 
57:36 Why the Mega Funds Have Just Replaced Tiger
 
01:04:08 GC, Lightspeed and a16z Cannot Do 5x on Their Funds… 
 
01:14:09 Single Biggest Threat to Benchmark

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

Chad Peets is one of the greatest sales leaders and recruiters of the last 25 years. From 2018 to 2023, Chad was a Managing Director at Sutter Hill Ventures. Chad has worked with the world's best CEOs and CROs to build world-class go-to-market organizations. Chad is currently a member of the Board of Directors for Lacework and Luminary Cloud and on the boards of Clumio and Sigma Computing. He previously served as a board member for Astronomer, Transposit, and others. He was an early-stage investor at Snowflake, Sigma, Observe, Lacework, and Clumio.
 
In Today's Discussion with Chad Peet's We Discuss:
 
1. You Need a CRO Pre-Product:
 
 • 

Why does Chad believe that SaaS companies need a CRO pre-product?
 • 
 • 

Should the founder not be the right person to create the sales playbook?
 • 
 • 

What should the founder look for in their first CRO hire?
 • 
 • 

Does any great CRO really want to go back to an early startup and do it again?
 • 
 
2. What Everyone Gets Wrong in Building Sales Teams:
 
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Why are most sales reps not performing?
 • 
 • 

How long does it take for sales teams to ramp? How does this change with PLG and enterprise?
 • 
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What are the benchmarks of good vs great for average sales reps?
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How do founders and VCs most often hurt their sales teams and performance?
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3. How to Build a Hiring Machine:
 
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What are the single biggest mistakes people make when hiring sales reps and teams?
 • 
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Are sales people money motivated? How to create comp plans that incentivise and align?
 • 
 • 

Why does Chad believe that any sales rep that does not want to be in the office, is not putting their career and development first?
 • 
 • 

Why is it harder than ever to recruit great sales leaders today?
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4. Lessons from Scaling Sales at Snowflake:
 
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What are the single biggest lessons of what worked from scaling Snowflake's sales team?
 • 
 • 

What did not work? What would he do differently with the team again?
 • 
 • 

What did Snowflake teach Chad about success and culture and how they interplay together?
 •

20VC: Anthropic Raises $30BN from Microsoft and NVIDIA | NVIDIA Core Business Threatened by TPU | Sam Altman's "War Mode" Analysed | Sierra Hits $100M ARR: Justifies $10BN Price? | Lovable Hits $200M ARR & Rumoured $6BN Round

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