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Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157

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. ----------------------------------------------- Timestamps: (00:00) Intro (01:27) The Science & Art of Successful Deals (05:03) Lessons from the Best & Worst Deals (15:54) The Qualities of Great CTOs (19:28) Investing in Competitive Markets (31:13) Founder-Led Companies & Product Expansion (34:43) Investing Mistakes (52:28) Acceptable Churn Rates for SMB & Enterprise Companies (59:00) Assessing Burn Rates & Revenue Projections (01:13:04) Quick-Fire Round ----------------------------------------------- In Today’s Episode with Jason Lemkin We Discuss: 1. Growth Rates and Churn Rates: Average/Good/Great: What is a growth rate that would excite Jason in a SaaS company? What is average? What levels of churn would worry Jason to see? What would excite him to see? What does Jason never tolerate when it comes to either growth rate or retention? 2. What Founder Combination Always Wins: Why does Jason believe you cannot lose money on a CEO salesperson and a technical CTO founding partnership? Why does Jason always meet the CTO for a second meeting in the diligence process? What questions does he ask? What do the best CTOs do or say? Why does Jason always want to sell his shares when the founders want to sell? Why does Jason believe that a company is never the same when the founders leave? 3. WTF is Happening in the World of VC: Why does Jason believe that pricing is worse than it has ever been in venture? Why does Jason believe that traditional seed VC is systemically broken? Why are companies getting stuffed with more cash than ever before? What does Jason know now about dilution that he wishes he had known when he started? Why does Jason believe that you should always recycle everything? 4. WTF is Happening in PE and Later Stage Markets: What happens to all the overpriced acquisitions like Zendesk and Salesloft where private equity way overpaid for them, they have no growth and no product innovation? What happens to the generation of public companies like Box, Dropbox and Twilio, all with low growth and little product innovation in the single-digit market caps? Why does Jason believe that Klaviyo is the most undervalued public company today? What does Jason believe will happen to Anaplan with Pigment eating their lunch? ----------------------------------------------- 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 #ceo #venturecapital #startup #deals

Jason LemkinguestHarry Stebbingshost
May 26, 20241h 24mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Jason Lemkin Dissects Broken Seed Investing, Dilution, and Founder Grit

  1. Jason Lemkin joins Harry Stebbings to deconstruct his best and worst SaaS investments, what actually drove returns, and why today’s seed market is structurally broken for most funds.
  2. He centers on founder quality—especially a hyper-committed CEO/CTO “binary pair”—alongside brutal standards on growth, churn, and product velocity as the non‑negotiables of venture‑scale outcomes.
  3. Lemkin argues that pricing and round dynamics are worse than ever: too much capital is flooding into too few truly fast‑growing companies, with insiders inflating valuations and obscuring weak fundamentals.
  4. He also lays out practical heuristics for evaluating CTOs, financial integrity, product quality, and SMB churn, while warning against holding too long after founders leave or doubling down reflexively on follow‑on rounds.

IDEAS WORTH REMEMBERING

5 ideas

Prioritize ultra‑committed founder pairs over everything else.

Lemkin’s best outcomes all share a CEO/CTO (or equivalent) pair who are 110% committed, technically strong, and relentlessly product‑ and sales‑oriented; without that, even strong early metrics rarely compound into fund‑returners.

Do early, deep diligence on the CTO and the product.

He now insists on a second call with the CTO immediately, asking them to demo, show what delights and frustrates them, and expose feature gaps; world‑class CTOs are proud, hyper‑transparent, and visibly obsessed with shipping better, faster software.

Use strict growth and churn thresholds to screen for venture scale.

For SaaS to IPO, he still expects “triple, triple, double, double” growth; at ~$1M ARR, 8–10% monthly growth is the bar, enterprise NRR must be >110%, and SMB churn above ~3–4% per month means it’s effectively not recurring software.

Avoid overfunded, insider‑inflated and structurally bad follow‑ons.

Lemkin’s largest cash loss came from reflexively writing a third check based only on top‑line growth; he now treats follow‑ons like new investments—re‑underwriting finances, customers, and integrity rather than assuming momentum equals quality.

Sell when founders leave or strongly want to sell.

He’s concluded that when founders exit or push hard for a sale (as at SalesLoft or Pipedrive), investors should largely follow; professional CEOs rarely sustain founder‑level agility and intensity, and holding for “one more card” often destroys optionality.

WORDS WORTH SAVING

5 quotes

Seed investing is systemically broken today. There's just as much capital, chasing fewer and fewer folks that can grow at triple-digit rates.

Jason Lemkin

If the churn is anything more than three or four percent a month, it's not even software anymore.

Jason Lemkin

The best investments go one to ten million in five quarters or less… You can't IPO unless you triple, triple, double, double.

Jason Lemkin

When the founders leave, I'm pretty much out. I would like to sell when the founders leave. Always.

Jason Lemkin

I don't think the best founders bullshit. You can build a unicorn bullshitting, but I don't think the best founders bullshit.

Jason Lemkin

Best vs. worst investments: SalesLoft, Pipedrive, Logikall, RevenueCat and big lossesFounder quality and the CEO/CTO “binary pair” as core investment filterSeed market structure, dilution math, and why many seed funds can’t make moneyDiligence evolution: early CTO calls, bank statements, customer references, product quality checksGrowth, churn, and revenue benchmarks (triple–triple–double–double; SMB vs enterprise churn)Competitive markets, founder‑led incumbents, and timing of expansion/second productsInsider rounds, overfunding, structured deals, and PE buyouts of slower‑growth SaaS

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