20VC: Why It Is BS That You Never Regret Paying A High Price To Get Into A Good Company, Why There Are Only 2 Price Points That Work in SaaS and Why eSports Will Be Bigger Than Traditional Sports in 5 Years Time with Jason Pressman @ Shasta Ventures

20VC: Why It Is BS That You Never Regret Paying A High Price To Get Into A Good Company, Why There Are Only 2 Price Points That Work in SaaS and Why eSports Will Be Bigger Than Traditional Sports in 5 Years Time with Jason Pressman @ Shasta Ventures

Jason Pressman is a Managing Director @ Shasta Ventures who have made investments in the likes of Nest, Dollar Shave Club, Smule, Class Dojo and more. With 10 portfolio company investments under his belt, Jason invests in both enterprise and consumer, currently serving on the boards of Crittercism, subscription billing unicorn Zuora, as well as Nextdoor and mobile music platform Smule. Prior to joining Shasta, Jason was Vice President, Strategy and Operations at venture-backed Walmart.com, where he took the online retailer from zero to large scale revenue in five years.

In Today's Episode You Will Learn:

1.) How Jason made his way into the world of venture from Walmart? What were the big takeaways from seeing Walmart enter their hyper-growth phase?

2.) Why does Jason believe it is bullshit to say, "you never regret paying a high price for getting into a good company"? How does Jason evaluate entry point? What makes one entry point attractive and another not?

3.) What does Jason see as the catalysts for the opening of public markets to tech companies? How long does he think this will continue? Is he concerned by the likes of Yext, IPOing with less than aggressive growth rates?

4.) Why does Jason believe there are only 2 price points that work in SaaS? What are they? How does this affect the structure and operations of your SaaS startup? What are the circumstances in which these price points do not apply?

5.) Why does Jason believe that eSports will be bigger than the NBA in 5 years? What are the catalysts driving this change? What needs to be formulated within eSports for this to happen?

Items Mentioned In Today's Show:

Jason's Fave Book: First, Break All The Rules

Jason's Most Recent Investment: Plays.tv

As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

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20Growth: Meta CMO Alex Schultz on How All Founders Have to Change Their Marketing Playbook in a World of AI | Is AI Plateauing, What it Means if China Wins the AI Race and Why Zuck is a Generational Leader

20Growth: Meta CMO Alex Schultz on How All Founders Have to Change Their Marketing Playbook in a World of AI | Is AI Plateauing, What it Means if China Wins the AI Race and Why Zuck is a Generational Leader

Alex Schultz is the Chief Marketing Officer and VP of Analytics at Meta, where he has spent nearly two decades shaping the company's growth and marketing strategy. He has been instrumental in scaling Facebook, Instagram, and WhatsApp to billions of users worldwide. Alex is is also the author of Click Here: The New Rules of Marketing, the definitive guide to modern growth — available now on Amazon. AGENDA: 00:00 – Is All Marketing Actually Performance Marketing? 04:00 – When Did Facebook Have the Wrong North Star? What Did They Learn? 16:00 – Will AI Create Companies Run by Just ONE Person? 27:00 – Is AI About to Hit the Biggest Plateau Since Self-Driving Cars? 30:00 – Is China Secretly Winning the Global AI Arms Race? 38:00 – Does AI Kill Content or Supercharge It? 44:00 – Why Brand Marketing Is Harder (and More Important) Than You Think 47:00 – Will Glasses Replace Phones Forever? 51:00 – What Would Alex Do If He Were Sundar at Google Today? 59:00 – What is the Greatest Strength and the Greatest Weakness of Zuck?

5 Sep 1h 10min

20VC: Anthropic Raises $13BN | Why Canva Will Not Direct List | OpenAI Buys Statsig for $1.1BN All Stock | Lovable Raising at $4BN + Vercel at $9BN: Justified or Not | Quarterly Results from SNOW, Mongo, ZOOM and more

20VC: Anthropic Raises $13BN | Why Canva Will Not Direct List | OpenAI Buys Statsig for $1.1BN All Stock | Lovable Raising at $4BN + Vercel at $9BN: Justified or Not | Quarterly Results from SNOW, Mongo, ZOOM and more

Agenda: 04:00 – Anthropic Raises $13BN: The Analysis? 19:00 – Is Zuck's $14BN Scale bet the biggest blunder in AI? 27:00 – Lovable Raising at $4BN and Vercel at $9BN: Justified or Madness? 36:00 – Quarterly Results for Snowflake, Mongo, Okta, Zoom Skyrocket: Is B2B SaaS back from the dead? 48:00 – Is Jensen Huang right there will be $4TRN in AI gains? 57:00 – Will AI wipe out SaaS margins with 10% GPU taxes? Or is Notion the exception? Items Mentioned in Today's Episode: Try NEXOS.AI for yourself with a 14-day free trial: https://nexos.ai/20vc

4 Sep 1h 14min

20VC: Cohere Founder on How Cohere Compete with OpenAI and Anthropic $BNs | Why Counties Should Fund Their Own Models & the Need for Model Sovereignty | How Sam Altman Has Done a Disservice to AI with Nick Frosst

20VC: Cohere Founder on How Cohere Compete with OpenAI and Anthropic $BNs | Why Counties Should Fund Their Own Models & the Need for Model Sovereignty | How Sam Altman Has Done a Disservice to AI with Nick Frosst

Nick Frosst is a Canadian AI researcher and entrepreneur, best known as co-founder of Cohere, the enterprise-focused LLM. Cohere has raised over $900 million, most recently a $500 million round, bringing its valuation to $6.8 billion. Under his leadership, Cohere hit $100M in ARR. Prior to founding Cohere, Nick was a researcher at Google Brain and a protégé of Geoffrey Hinton. AGENDA: 00:00 – Biggest lessons from Geoff Hinton at Google Brain? 02:10 – Did Google completely sleep at the wheel and miss ChatGPT? 05:45 – Is data or compute the real bottleneck in AI's future? 07:20 – Does GPT5 Prove That Scaling Laws are BS? 13:30 – Are AI benchmarks just total BS? 17:00 – Would Cohere spend $5M on a single AI researcher? 19:40 – What is nonsense in AI that everyone is talking about? 25:30 – What is no one talking about in AI that everyone should be talking about? 33:00 – How do Cohere compete with OpenAI and Anthropic's billions? 44:30 – Why does being American actually hurt tech companies today? 45:10 – Should countries fund their own models? Is model sovereignty the future? 52:00 – Why has Sam Altman actually done a disservice to AI?

1 Sep 1h 7min

20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi

20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi

Jason James is the Co-Founder of Tezi and one of the leading product minds in the valley. Prior to Tezi, Jason was the VP Product at Instacart and before that was Head of Product and Design at Thumbtack. AGENDA: 00:00 Product lessons scaling Instacart to $40B – what really moves the needle 02:15 Why "quick optimizations" won't build billion-dollar products 04:30 MVPs are dead? How AI is reshaping product development 07:00 Do startups even need PMs anymore in the age of AI? 11:30 The biggest product mistake Jason made building Tezi 16:30 Why most hiring managers fail at recruiting 20:00 The resume trap: how to spot if someone was just "on the elevator up" 26:00 The three roles founders always end up firing 28:00 Are most CPOs actually terrible? 36:30 The myth of startup "culture" – why growth is the only thing that matters 43:00 Did DoorDash actually beat Instacart? The inside take 48:00 Fundraising secrets founders never realize until it's too late

29 Aug 53min

20VC: Anthropic's $10BN Round | Klarna's IPO Broken Down | Inside a16z's 72 Deal Seed Investment Machine | Martin Casado: Is Consensus Investing the Only Game | Why Satya is Chatting S*** on SaaS Apps Disappearing featuring Marc Benioff

20VC: Anthropic's $10BN Round | Klarna's IPO Broken Down | Inside a16z's 72 Deal Seed Investment Machine | Martin Casado: Is Consensus Investing the Only Game | Why Satya is Chatting S*** on SaaS Apps Disappearing featuring Marc Benioff

AGENDA: ​​00:00 – Marc Benioff vs Snowflake, Databricks & Palantir: Who Wins the Data Cloud War? 05:10 – Does Benioff Feel The Need to Buy AI Talent Like Zuck Is? 09:00 – What Salesforce has Learned From Palantir on Forward Deployed Engineers? 18:00 – Will SaaS apps disappear in an AI world? Why Satya is Chatting S*** 23:40 – Are SDRs really screwed by AI… or just evolving? 26:10 – Benioff on Who Wins: OpenAI or Anthropic? 30:00 – Nat Friedman reports to Alex Wang: Genius move or career downgrade? 34:00 – Anthropic's $10B round: Have we hit peak AI hype? 47:00 – Klarna's wild ride: From $45B to $6B to IPO at $15B 55:00 – Inside a16z's seed machine: 72 bets vs Sequoia's 27 57:45 – Martìn Casado: Is consensus investing dangerous—or the only game? 01:05:00 – The big lesson: consensus, contrarian, and why investing is harder than ever

28 Aug 1h 11min

20VC: Do Margins Matter in AI? | Is Defensibility Gone For Good? | Is Vertical SaaS Dead in a World of AI | What SaaS Rules Are BS and No Longer Apply in a World of AI | The Future of Venture: Why Chanel vs Walmart is BS with Byron Deeter

20VC: Do Margins Matter in AI? | Is Defensibility Gone For Good? | Is Vertical SaaS Dead in a World of AI | What SaaS Rules Are BS and No Longer Apply in a World of AI | The Future of Venture: Why Chanel vs Walmart is BS with Byron Deeter

Byron Deeter is a Partner at Bessemer Venture Partners, and one of the most renowned SaaS investors. Byron has led 19 unicorn investments, including IPO successes like ServiceTitan, Procore, Twilio, Box, Gainsight, Intercom, DocuSign, SendGrid. His portfolio includes eight companies that have gone public. Insane. Agenda: 00:00 – Why are the stakes in AI higher than ever before? 05:20 – Is defensibility in AI gone for good? 07:40 – Do margins even matter when backing the next Anthropic or Perplexity? 09:50 – How does Byron think about future dilution when investing in AI today? 12:10 – With 40% of venture money going to 10 deals, is there any point investing elsewhere? 13:40 – Is vertical SaaS dead? Is there any point when the large players can own it? 18:00 – Will AI shift from the tech budget to the human labor budget and unlock trillions? 21:10 – Are we entering the era of billion-dollar businesses built by 10 people? 25:20 – Is treble-treble-double-double now too slow for AI companies? 33:10 – In today's AI gold rush, is it better to scream the loudest or just build the best product? 41:10 – What specific growth rates are best in class, good and not good enough today? 55:00 – Is venture now just a game of scale — Chanel vs. Walmart?

25 Aug 1h 21min

20VC: Databricks at $100BN | Chamath's SPAC Revival: Peak Mania? | OpenAI Staff Cash Out Billions & Sam Altman Will Spend Trillions | CoreWeave's $11B Debt Bet & Nubank's $2.5B Profit Shocker

20VC: Databricks at $100BN | Chamath's SPAC Revival: Peak Mania? | OpenAI Staff Cash Out Billions & Sam Altman Will Spend Trillions | CoreWeave's $11B Debt Bet & Nubank's $2.5B Profit Shocker

Agenda: 00:00 – Databricks hits $100B: Bubble or just the beginning? 03:15 – Is Databricks actually undervalued at 25x revenue? 07:40 – Are we on the verge of the biggest IPO wave ever? 11:30 – Can Andreessen's Databricks bet return $30B+? 18:10 – Who really gets rich when mega-unicorns IPO? 19:30 – Is the return of Chamath's SPACs the ultimate bubble signal? 28:00 – Should OpenAI staff be cashing out billions in secondaries? 33:30 – Founder raises $130M… then walks away. Is this the new normal? 36:30 – Nubank's $2.5B profit: The best FinTech in the world? 48:00 – On Running at $15B: Can consumer brands still be VC-backed rockets? 52:00 – CoreWeave takes on $11B in debt: smart bet or ticking time bomb? 1:11:00 – Will AI spend really hit trillions—or is it all hype?

21 Aug 1h 27min

20VC: Lovable CEO Anton Osika on $120M in ARR in 7 Months | The Honest Truth About Defensibility and Unit Economics for AI Startups | The State of Foundation Models: Long Grok, Short OpenAI, Why | Replit vs Lovable vs Bolt: What Happens

20VC: Lovable CEO Anton Osika on $120M in ARR in 7 Months | The Honest Truth About Defensibility and Unit Economics for AI Startups | The State of Foundation Models: Long Grok, Short OpenAI, Why | Replit vs Lovable vs Bolt: What Happens

Anton Osika is the Co-Founder and CEO @ Lovable, the fastest growing company on the planet. In just 7 months, they have scaled from $0 to $120M in ARR. They have raised over $200M in funding from some of the best including Accel, Creandum and 20VC. Their latest round priced the company at a whopping $2BN. Agenda for Today: 00:00 – Is AI an Arms Race… Or Just a Talent War? 03:45 – How Does Anton Compete with Zuck's $100M Packages for Talent 07:30 – Founder Mode vs. Structure: Can Chaos Scale? 10:15 – The Brutal Truth About Defensibility in AI Startups 13:20 – Unit Economics: Are AI Companies Doomed to Bleed Cash? 17:00 – GPT-5: Game-Changer or Overhyped Disappointment? 20:10 – How Lovable Hit $100M ARR in Just 7 Months? 25:15 – Replit, Figma, Bolt: Which Competitor is the Best? 30:00 – The Security Bombshells No One Talks About 36:40 – Should Anyone Still Study Computer Science? 40:30 – Work-Life Balance Is Dead: Inside Anton's 10x Culture 56:00 – OpenAI, Anthropic, or Grok: Who Wins the AI Wars?

18 Aug 1h 8min

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