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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 2, 20241h 20mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

SaaS Turbulence: PE Wipeouts, Slowing Giants, But New Winners Rising

  1. 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.

IDEAS WORTH REMEMBERING

5 ideas

Private equity is no guaranteed exit path for SaaS anymore.

Vista writing Pluralsight down from a $3.5B buyout to zero—despite strong margins—shows that levered PE deals can fail when debt service outruns cash generation; if similar issues hit other big PE SaaS deals (Zendesk, Anaplan, etc.), LPs may rethink allocations and founders lose a major liquidity avenue.

Classic B2B SaaS selling into tech is in a structural downcycle.

Salesforce, Mongo, Workday, and others are ratcheting down growth expectations, with Salesforce projecting mid‑single‑digit growth and weak NRR as customers cut seats and shrink deal sizes; selling B2B software to tech buyers (“B2B2B”) remains brutal, even as broader macro indicators are fine.

Non‑tech, vertical, and B2B2C SaaS are still growing aggressively.

Canva (~$2.3B revenue, ~40% growth), Toast, Samsara, Zscaler, Monday.com, and Klaviyo are all growing ~30–50% at high scale by selling into SMBs, traditional industries, or consumers, demonstrating that the pain is concentrated in tech‑buyer segments, not SaaS as a whole.

AI spend is largely substitutional, not net‑new budget—yet.

Enterprises are funding AI by killing existing tools (e.g., churning a dozen apps to buy one AI solution), and Gartner data suggests GenAI’s boost to SaaS is mostly reallocation; incumbents like Salesforce, Dell, and ServiceNow talk up AI products, but none credibly show material revenue uplift so far.

Founders must know exactly where their budget comes from and ask.

In a world of constrained and reallocated spend, strong enterprise sellers explicitly ask early in discovery whether a project is budgeted and from which line; founders who don’t understand the budget source—and what must be cut to fund them—risk being swapped out to free up AI or other priorities.

WORDS WORTH SAVING

5 quotes

“If a lot of these big PE deals can’t service their debt, we’re writing off tens of billions. This is not a trillion‑dollar industry.”

Jason Lemkin

“Everyone on Twitter thinks there’s one root cause. But if Canva’s at $2.3 billion growing 40%, Samsara’s growing 40% at over a billion, and Zscaler’s growing 40% at two billion, you can’t say all is bad.”

Jason Lemkin

“So far the evidence is no: incumbents will build great AI products, but it’s not clear they’ll get any revenue boost from it.”

Jason Lemkin

“I think we’ve made a terrible pact with the devil in public SaaS: the market wants 30–40% margins, but there’s no money left for R&D.”

Jason Lemkin

“One large accidental mistake founders make in fundraising is asking for too much money.”

Jason Lemkin

Vista’s Pluralsight write‑down and the fragility of the PE model in SaaSSalesforce, Mongo, and other incumbents falling to low double or single‑digit growthWhere SaaS is still thriving: B2B2C, vertical SaaS, SMB and non‑tech buyersAI economics: substitution vs net‑new spend, and impact on incumbentsValuation compression, sparse IPOs, and the liquidity crunch for VCs and LPsFounder and VC behavior: fundraising mistakes, risk appetite, and markupsLemkin’s SaaStr/venture tradeoffs, events economics, and personal operating lessons

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