Skip to content
The Twenty Minute VCThe Twenty Minute VC

Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160

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? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Jason Lemkin on Twitter: https://twitter.com/jasonlk Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #jasonlemkin #saastr #saas #founder #ceo #venturecapital #startup #salesforce #pluralsight #mongodb #dropbox #twilio #notion

Jason LemkinguestHarry Stebbingshost
Jun 3, 20241h 20mWatch on YouTube ↗

Episode Details

EPISODE INFO

Released
June 3, 2024
Duration
1h 20m
Channel
The Twenty Minute VC
Watch on YouTube
▶ Open ↗

EPISODE DESCRIPTION

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?

1. 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?

1. 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?

1. 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? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Jason Lemkin on Twitter: https://twitter.com/jasonlk Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #jasonlemkin #saastr #saas #founder #ceo #venturecapital #startup #salesforce #pluralsight #mongodb #dropbox #twilio #notion

SPEAKERS

  • Jason Lemkin

    guest
  • Harry Stebbings

    host

EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Jason Lemkin and Harry Stebbings, Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 explores saaS Turbulence: PE Wipeouts, Slowing Giants, But New Winners Rising Harry Stebbings and Jason Lemkin dissect a brutal but revealing week in SaaS: Vista’s Pluralsight write‑off, Salesforce and Mongo’s growth resets, and compressed public market multiples. They argue that the private equity ‘savior’ narrative is cracking, liquidity is scarce, and public markets are demanding profitability at the expense of R&D. At the same time, a cohort of non‑tech, vertical, and B2B2C SaaS companies—like Canva, Toast, Samsara, Zscaler, and Klaviyo—are still growing 30–40%+ at scale, showing SaaS is not universally “broken.” The conversation also covers AI as largely substitutional spend, venture dynamics (TVPI vs DPI, secondaries, fund strategy), and the future IPO pipeline, alongside Lemkin’s candid reflections on being both an investor and SaaStr operator.

RELATED EPISODES

Inside Legora: Jude Law Generated $50M Pipeline | Are They Undervalued at $5.5BN? | Patrick Forquer

Inside Legora: Jude Law Generated $50M Pipeline | Are They Undervalued at $5.5BN? | Patrick Forquer

Cliff Weitzman: What I Learned from 100 of the World’s Top CEOs & Why Tokens Will Outspend Salaries

Cliff Weitzman: What I Learned from 100 of the World’s Top CEOs & Why Tokens Will Outspend Salaries

Shopify CEO on How AI is a Scapegoat for Mass Layoffs & Trump Derangement Syndrome in Canada

Shopify CEO on How AI is a Scapegoat for Mass Layoffs & Trump Derangement Syndrome in Canada

Inside Clay's Sales Playbook | Becca Lindquist

Inside Clay's Sales Playbook | Becca Lindquist

Jackie Reses: The Most Powerful Woman in Finance; Making $50BN for Yahoo on Alibaba | E996

Jackie Reses: The Most Powerful Woman in Finance; Making $50BN for Yahoo on Alibaba | E996

Tom Hulme & Stan Boland:  Lessons from Jensen Huang & How to Fix the UK Tech Ecosystem

Tom Hulme & Stan Boland: Lessons from Jensen Huang & How to Fix the UK Tech Ecosystem

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

Add to Chrome