This Week in SaaS: PluralSight Goes to Zero, Salesforce and Mongo Hit Hard, The Next IPO Candidates and How Do We Solve the Problem of Liquidity in Venture Capital

This Week in SaaS: PluralSight Goes to Zero, Salesforce and Mongo Hit Hard, The Next IPO Candidates and How Do We Solve the Problem of Liquidity in Venture Capital

Jason Lemkin is one of the OG SaaS investors with all of his first five investments turning into unicorns with Pipedrive, Algolia, Talkdesk, Salesloft and RevenueCat all in his portfolio. SaaStr is the largest global community in SaaS and he has taught a generation the fundamentals of SaaS on saastr.com.

In Our First Ever Episode of This Week in SaaS

1. PluralSight Goes to Zero:

  • WTF happened to PluralSight? How did it go from $3.5BN to $0?
  • Will this have a wider impact on the willingness of PE to buy tech companies?
  • Who are the next contenders to go from hero to zero? Zendesk? Anaplan?
  • Will this generation of PE funds be let off by their LPs for a poor vintage?

2. Salesforce's Worst Stock Market Drop Since 2004 + Mongo Takes a 23% Hit:

  • Why did Salesforce lose $50BN of market cap in a single day?
  • Is the same true for MongoDB taking a 23% hit in one day?
  • What does it mean when the new normal is these once hyper-growth companies now growing only 6% per annum?

3. The Settlers into Slow Growth:

  • Why does Jason believe that Dropbox and Box have both settled into a world of slow growth?
  • What happens to Twilio from here in a world post Jeff Lawson?
  • What happens to Retool from this point on?
  • Would Jason be a buyer of Notion at $10BN?

4. Venture Capital is Broken:

  • Why does Jason believe that we need to see a relation of public multiples for the math in venture capital to work again?
  • Why does Jason believe that the way we mark portfolios with TVPI leads to corrupt and bad behaviour?
  • How does Jason think we will solve the problem of liquidity with IPOs being shut, M&A being out of the window and now PE being a doubt as the source of buyers?

Episoder(1436)

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 F...

28 Aug 20251h 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, B...

25 Aug 20251h 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 An...

21 Aug 20251h 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...

18 Aug 20251h 8min

20VC: 15 Term Sheets in 7 Days and Choosing Benchmark | Harvey vs Legora: Who Wins Legal and How to Play When You Have $600M Less Funding | Are AI Models Plateauing Today | Building a 9-9-6 Culture From Stockholm with Max Junestrand

20VC: 15 Term Sheets in 7 Days and Choosing Benchmark | Harvey vs Legora: Who Wins Legal and How to Play When You Have $600M Less Funding | Are AI Models Plateauing Today | Building a 9-9-6 Culture From Stockholm with Max Junestrand

Max Junestrand is the Co-Founder and CEO @ Legora, the collaborative AI powering the next generation of lawyers. Now this is an insane story for many reasons; first, Max turned down a multi-million do...

15 Aug 20251h 20min

20VC: GPT5: Sam Altman's Masterplan or a Gift To Anthropic | Palantir & Shopify Crush Earnings | Monday & Datadog Perform But Hit Hard by Wall St | Should Perplexity Buy Chrome for $34.5BN |

20VC: GPT5: Sam Altman's Masterplan or a Gift To Anthropic | Palantir & Shopify Crush Earnings | Monday & Datadog Perform But Hit Hard by Wall St | Should Perplexity Buy Chrome for $34.5BN |

AGENDA: 00:04 – Was GPT-5 the Biggest AI Letdown Yet? 00:17 – Is OpenAI's Real Target Anthropic's $6B Revenue? 00:22 – Why Anthropic Might Secretly Be Worried 00:28 – The Hidden Business Strategy Behi...

14 Aug 20251h 22min

20VC: Figma, Scale, Wiz: Inside Index's Decacorn Factory | Decision-Making, Investment Process, Biggest Lessons, Biggest Misses | Why Gross Margin is a Fallacy at Seed | Never Turn Down a Deal on Price with Martin Mignot, Partner @ Index Ventures

20VC: Figma, Scale, Wiz: Inside Index's Decacorn Factory | Decision-Making, Investment Process, Biggest Lessons, Biggest Misses | Why Gross Margin is a Fallacy at Seed | Never Turn Down a Deal on Price with Martin Mignot, Partner @ Index Ventures

Martin Mignot is a Partner at Index Ventures, the best-performing fund in the world right now. In the last three months, they have sold Wiz for $ 32 billion, sold Scale for $14.9 billion, and IPO'd Fi...

11 Aug 20251h 19min

20VC: The $BN Greenoaks Backed Protein Bar | Hitting $100M Revenues in David's First Year: Lessons & Mistakes | $0 to $600M: The Untold RXBAR Story | Product-Market-Fit, Pricing, Branding: What Every Founder Gets Wrong Today with Peter Rahal

20VC: The $BN Greenoaks Backed Protein Bar | Hitting $100M Revenues in David's First Year: Lessons & Mistakes | $0 to $600M: The Untold RXBAR Story | Product-Market-Fit, Pricing, Branding: What Every Founder Gets Wrong Today with Peter Rahal

Peter Rahal is the Co‑Founder & CEO of David Protein, the highest protein‑to‑calorie ratio for any protein bar on the market. Peter has raised over $85M from Greenoaks, Dr. Peter Attia and Dr. Andrew ...

8 Aug 20251h 6min

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