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(1434)

20VC: Inside Carnegie Mellon's $4BN Endowment | Why 90% of LPs Shouldn't Invest in VC | The $140BN Problem with Multi-Stage Funds | The Hidden Math Behind DPI, TVPI, and Illiquidity with Miles Dieffenbach

20VC: Inside Carnegie Mellon's $4BN Endowment | Why 90% of LPs Shouldn't Invest in VC | The $140BN Problem with Multi-Stage Funds | The Hidden Math Behind DPI, TVPI, and Illiquidity with Miles Dieffenbach

Miles Dieffenbach is Managing Director of Investments at Carnegie Mellon University, where he helps oversee a $4 billion endowment with a focus on venture capital, private equity, and alternative inve...

4 Aug 20251h 27min

20VC: Benchmark Loses Another Partner | Elad Gil Raises a Monster $1.5BN Solo GP Fund | Why Apple Need a Management Overhaul | Why Google is the Best Performing Hyperscaler | Will Cursor Hit $4BN ARR & Lovable $400M ARR by EOY 2026?

20VC: Benchmark Loses Another Partner | Elad Gil Raises a Monster $1.5BN Solo GP Fund | Why Apple Need a Management Overhaul | Why Google is the Best Performing Hyperscaler | Will Cursor Hit $4BN ARR & Lovable $400M ARR by EOY 2026?

Agenda: 00:00 - Why Benchmark Is Bleeding Partners (and Why That's the New Normal) 04:57 - "I Wouldn't Leave Benchmark… Unless I Had THIS" — Jason on Brand vs Autonomy 09:01 - The Rise of the Solo GP ...

31 Jul 20251h 21min

20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China

20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China

Martin Casado is a General Partner @ a16z where he leads the firms $1.25BN infrastructure fund. At a16z, Martin has led investments in companies like Cursor, dbt Labs, and Fivetran to name a few. Befo...

28 Jul 20251h 10min

20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

Fernando Fanton is one of the most respected product leaders in Europe, having held Chief Product Officer roles at Monzo and Just Eat. He previously led product and tech at Rappi, one of Latin America...

27 Jul 20251h 7min

20VC: Lovable Raises at $2BN & Hits $100M ARR | Is Cursor Worth $28BN at $1BN in ARR | How Do All Providers Deal with Anthropic Dependency Risk | Are Seed Funds F******: Have Mega Funds Won | Figma IPO Breakdown: Where Does it Price?

20VC: Lovable Raises at $2BN & Hits $100M ARR | Is Cursor Worth $28BN at $1BN in ARR | How Do All Providers Deal with Anthropic Dependency Risk | Are Seed Funds F******: Have Mega Funds Won | Figma IPO Breakdown: Where Does it Price?

Agenda: 00:00 – Did Jason Just Kill Replit? 03:45 – Why Claude Lies To You and Cannot Be Trusted 06:50 – You Cannot Trust Agents. Period. 10:20 – Why Windsurf Was Dead Without Claude 12:30 – Cursor v...

24 Jul 20251h 21min

20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |

20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |

Edwin Chen is the Founder and CEO of Surge. Founded in 2020, Surge has scaled to $1BN+ in revenue with zero external funding. At the same time, their competitor, Scale.ai raised over $1.3BN to reach $...

21 Jul 20251h 6min

20VC: Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale | Did Google Overlook a Goldmine in the Core Asset and Did Founders Leave a Sinking Ship | How Cursor and Cognition Deal with Ever Increasing Reliance on Anthropic

20VC: Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale | Did Google Overlook a Goldmine in the Core Asset and Did Founders Leave a Sinking Ship | How Cursor and Cognition Deal with Ever Increasing Reliance on Anthropic

Scott Wu is the co-founder and CEO of Cognition, the company behind Devin, the world's first AI software engineer. On Friday last week they pulled off the acquisition of the year, acquiring Windsurf, ...

18 Jul 202548min

20VC: Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not | Lovable vs Replit: Will These Be $100BN Businesses | Why Elon Could Beat Sam Altman with the New Grok | Why Every S&P 500 Company Will Buy Bitcoin?

20VC: Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not | Lovable vs Replit: Will These Be $100BN Businesses | Why Elon Could Beat Sam Altman with the New Grok | Why Every S&P 500 Company Will Buy Bitcoin?

Agenda: 00:00 Windsurf was dead—then this deal changed everything 05:00 The Windsurf x Google x Cognition saga explained 09:00 The OpenAI deal collapsed—what really happened 15:00 FTC rules forced a b...

17 Jul 20251h 21min

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