
Jason Lemkin
Frontier Insights
Frontier Thesis: AI unlocks a software golden era but destroys the permanence of recurring revenue. Product-market fit has compressed from years to weeks, rendering legacy growth extrapolation and traditional SaaS defensibility obsolete.
Strategic Decisions: Double down on proprietary distribution, deep workflow entrenchment, and ruthlessly capital-efficient paths to profitability. In late-stage markets, bypass speculative mega-rounds in favor of bolt-on M&A and rightsized liquidity events.
Risks & Warnings: Thin wrapper products generate rapid yet ephemeral ARR, while hyperscalers cannibalize incumbent prosumer tools (e.g., Canva). Massive private valuations face violent multiple compression and severe debt-dilution overhangs.
Key Views & Dialogues
Canva Slahes Growth | Talent Exodus at Google | Revolut’s $50B CEO Package | Musk’s $55B Terrafab
- 🗓️ Date:
2026-08-13| 🎙️ Show:20VC
Canva’s 2026 growth outlook has fallen from 30% to roughly 20%, while agents may bypass prosumer tools without user churn, exposing a structural distribution risk. At roughly $4B ARR, Jason Lemkin sees $12B fair value if growth does not decelerate, but proving ChatGPT-cannibalization wrong—and monitoring AI serving costs—remains decisive.
View Dialogue Notes & Key Takeaways
Canva’s reported 2026 growth cut — from 30% entering the year to likely 20% by year-end, partly attributed by CEO Melanie Perkins to AI serving costs — reframes the prosumer-SaaS complex, because the real question isn’t margin compression but “are you thirty on the way to twenty on the way to ten?” Jason Lemkin pegs fair value at ~$12B for ~$4B ARR growing 20% and not decelerating; Rory O’Driscoll notes comparable infrastructure names at mid-20s growth trade at 15–17x NTM because they carry no existential question, so Canva could be $12B or less while exposed, and “$12B and up” only if it disproves the ChatGPT-cannibalization narrative by growing.
The scariest datapoint isn’t user churn — it’s agentic distribution quietly disappearing. Lemkin’s SaaStr churned both Canva and Notion (“Canva and Notion did nothing wrong at all. Nothing, and we didn’t need them” in the agentic era), and the ad-creative network SaaStr built on its own agent “never once occurred” to use Canva. Layer on Amjad’s line about Airtable — “the era of no-code is over” — and the prosumer tier looks structurally exposed, while Gartner-type data Jason believes puts successful enterprise agentic deployment below 10%.
The Jeff Dean exit (with three others) and Demis Hassabis stepping back to chairman is a compute-allocation story, not palace intrigue. O’Driscoll’s mechanism: compute given to Google Cloud “turns into 30% operating margins in a day,” compute to Gemini might work, while compute to science is a 5–7-year moonshot that might be indulged “at the 10% level” — so the scientists left. His grade: “Google’s efforts so far are B+, A-. They’re not A+,” with “no impact whatsoever in coding, which is the mother lode that’s feeding the Anthropic beast.”
Rory urges Anthropic to sprint to an IPO; Jason says an IPO within roughly 60 days would make the AI bets tangible. O’Driscoll: “You’ve pulled ahead of ChatGPT comfortably… to a point where it’s embarrassing. It’s never going to be better… You should go now. You should go fast.” Lemkin says an IPO would make Canva and friends “a distant memory of a bygone era of software.”
Revolut’s reported CEO package — ratcheting toward ~40% ownership at a $500B valuation — would give roughly 16% of the $200B→$500B value creation, which O’Driscoll calls “abnormally high,” while Lemkin reads it primarily as control and incentive, not merely money. Rory would probably approve this particular package, but only against operational metrics (“If you’re going to give someone 50 fucking billion dollars, you owe it to yourself to spend more time thinking about what you’re getting”); Jason’s categorical counter: “Any investment I’ve made that is not run by a founder is a zero. It’s gonna be a zero in this age” — the baby Elons will get these packages regardless.
Musk’s Terrafab — $16.8B, with a reported first installment — is vertical integration forced by a decade of supply constraint: “I can’t even get TSMC on the phone ‘cause Jensen’s out there all the time.” O’Driscoll flags it as the position most exposed to any AI-spend slowdown (“the all-in bet is the one that slows down the most the fastest”), with Intel — part of the consortium — reportedly completing its first equity raise since it went public around 1979.
Data-center NIMBYism, including Ro Khanna’s proposed “data center bill of rights,” may self-resolve through 50-state regulatory competition — but tech earned the hostility. O’Driscoll says locals mostly ask, “I don’t know what I’m getting here,” so developers should guarantee no electricity-cost increase plus a $5K–$10K local dividend; and “if you spend three years saying AI’s gonna kill you all, you shouldn’t be surprised we hate it.”
Post-Airtable (~$6B blended exit) and post-Canva, Lemkin says it’s “time to be a little extra skeptical of marks,” while the trimming debate stays unresolved. O’Driscoll says statistics would suggest you probably should have sold roughly 70% of the time, “but the holders compound forever and the ones you sell don’t compound at all” — citing Hendrik Bessembinder’s research that less than 1% of companies generate 90% of public-market capital gains. Meanwhile Whatnot ($545M at $20B, GMV doubling toward $16B at a 12% take) shows “there’s gold in the things that aren’t going to be destroyed by AI.”
🔗 Original source & video: Canva Slahes Growth | Talent Exodus at Google | Revolut’s $50B CEO Package | Musk’s $55B Terrafab
20VC: Why Seed is for Suckers | a16z’s $20BN Fund & Founders Fund’s $4.6BN: What Makes Them So Good | Why Josh Kushner Is the Master of Venture Capital Strategy | Why Extended Private Markets Screw US Citizens with Jason Lemkin and Rory O’Driscoll
- 🗓️ Date:
2025-04-17| 🎙️ Show:20VC
Late-stage capital can skip years of seed execution when outcomes reach $20-100BN, but AI now makes product-market fit vulnerable to a five-week collapse and increases risk per dollar of revenue. With roughly $3 trillion in private venture assets, including $2 trillion of mature SaaS, investors face prolonged profitability drives, private-to-private mergers, fee pressure, and potentially bimodal fund returns.
View Dialogue Notes & Key Takeaways
Jason Lemkin’s provocation names the episode: when outcomes are $20-100BN, “seed is for suckers.” A late-stage fund just put almost nine figures into one of his unicorns and owns as much as he does — “they skip years of work and stress,” get a 1X worst case, and “achieve liquidity in a quarter of the time.” Rory O’Driscoll concedes the math but adds the catch: that game is only open to those handed large, forgiving capital — “no one offered me a billion dollars in 2009.”
Spreadsheet SaaS investing is dead. Rory’s Box position was “the exact same in 2010 as 2024”; for 20 years the direction was obvious and only the math needed analyzing. Now the installed market is saturated (“anyone who needed a DocuSign account got it in COVID”) while AI startups “acquire and lose product market fit two or three times in a two-year period.” Jason’s compression: “it used to take you five years to fall out of product market fit. Now it can be five weeks.” Every check today buys more risk per dollar of revenue — expect bimodal fund results.
The $3 trillion question: that’s the fair market value of private venture assets, and roughly $2 trillion of it is mature, slower-growth SaaS with no IPO trajectory. PE isn’t tire-kicking much — it wants “a boring-ass software company in a teeny-tiny vertical with 40% market share,” the opposite of venture’s sub-scale horizontal companies with no pricing power. “You can’t walk away from $2 trillion”: expect grim, case-by-case grinding — private-to-private mergers, profitability slogs, small IPOs.
Andreessen Horowitz’s $20BN rationale: Jason’s hypothetical spreadsheet of every S-tier deal they passed on (the whole Databricks round at $27BN in 2021 would already be 2.5X). Rory’s caveat: the game stops only “when the LPs’ bosses, the overall CIOs, stop allocating capital to venture” — the 2022 crash was merely “a pause for breath.” The buried risk is correlated multiple compression: a Nifty-50-style regime turns marquee-asset strategies into a 0.5-0.7X, versus 1.5X for conventional venture.
Founders Fund is idiosyncratic, not replicable. The leaked numbers show exactly what they advertised — 10-15-year holds (SpaceX from ~‘07-‘08) compounding 30-40% gross into 8-10X funds, plus the stones to take massive concentration. Rory now says “my Bayesian prior on financial matters in venture should be checking what Peter Thiel does.” But an LP funding ten funds to be “just like Founders Fund” makes no sense — “they’re not the same people with the same approach.”
Extended private markets screw US citizens — Rory’s public-policy indictment: the same Stripe compounding used to reach savers through Fidelity at 70bps; now it reaches them through Thrive at 2-and-20, cutting a 15% gross to ~10% net instead of 14.3%. “A monstrously stupid outcome” that ends only when late-stage privates underperform equivalent publics by the amount of the fees — then capital reallocates.
Cycle-top warning lights: term sheets with “every box checked to the maximum” in one-day hot deals, sell-5%-get-7% founder secondary refreshes, Galbraith’s “bezel” growing unseen in the boom, 93% of more than 2,000 SaaStr respondents admitting they lie to win deals, and ARR that is “neither A nor R, nor R” — Rory has shifted underwriting to GAAP because “ARR is a made-up number and GAAP is a fact.”
The buy-or-not-buy game splits the panel: OpenAI at $300BN — Rory no, Jason out of anything north of $100BN (“all my decisions are bad”), Harry “I would buy the shit out of this. Escape velocity reached.” Cursor at $10BN hangs entirely on durability: “if it’s SaaS, take my money” (140-200% NRR, competitors destroyed) — but users switch IDEs in a week.
20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia’s 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech
- 🗓️ Date:
2025-04-03| 🎙️ Show:20VC
AI is creating a golden age of software and extraordinary revenue growth, but thin wrappers, dilution, and uncertain recurring revenue are exposing the limits of the old scale-equals-durability model. Moveworks’ $2.85B sale shows the value of enterprise distribution and workflow integration, while CoreWeave’s IPO, a possible $2B put obligation, and constrained M&A make execution and liquidity the next catalysts.
View Dialogue Notes & Key Takeaways
Jason Lemkin’s central call is that AI is opening a “golden age of software” while destroying the old assumption that scaled revenue is durable. If software expands from 2% to 4% of GDP, he sees 100 or more decacorns. Harry’s framing was that every VC has five or ten unicorns that are no longer unicorns, now growing in the single digits or teens; Lemkin expects late-stage slowdowns to become commonplace by 2026 and those stranded assets to become less attractive to acquire.
Hot AI rounds can look cheap at roughly 20x forward ARR only because investors extrapolate extraordinary slopes while remaining uncertain whether the “R” is recurring and durable. Lemkin says markups still grade VCs and some LPs, while Harry notes that entering at $200M ARR can shorten duration; the counterweights are dilution that Lemkin estimates might approach 10% annually and a venture cash cycle stretching toward 20 years.
“Triple-triple, double-double” remains elite operating performance but is currently “silver in a gold rush” to perhaps 80% of B2B investors. Lemkin’s prescription is a year-long, relationship-led process with roughly 50 investors and honest monthly updates: “It only takes one.” Founders without Cursor-like heat should avoid artificial Friday deadlines and may be better off accepting a valuation 30% lower if that gets the round closed.
AI demand is producing real revenue faster than technical substance, while investors remain “addicted to top-line growth.” Lemkin has seen companies reach $2M in 60 days or eight figures inside a year with humans running prompts behind thin wrappers; yet AI efficiency does not necessarily reduce capital needs, because RevenueCat took a 2x productivity gain and “plowed it all into new hiring.”
Moveworks accepted ServiceNow’s $2.85B offer after years of deep integration and accelerating demand made ServiceNow’s distribution especially compelling. Bhavin Shah said 250 of 350 customers already used ServiceNow, while Moveworks had five million users against ServiceNow’s 150M-plus; he concluded that Moveworks could not match the market’s scale and speed independently. The strongest ROI was not saving an employee three hours, but automating core workflows across systems such as SAP, Workday, Salesforce, Concur and Jira.
Lemkin expects an IPO and M&A “gold rush” within roughly 18 months, but sees little evidence that PE will rescue slow-growth unicorns. He expects large private companies such as Stripe, Figma, Chime and Canva may list, yet says cash-flow-positive assets at $20M, $50M or even $100M are not attracting the “tire kicking” he once saw; PE instead appears to be combining holdings into “Frankensteins” such as SalesLoft with Drift and Gainsight with Skilljar.
CoreWeave getting public was a major entrepreneurial achievement, but its real scorecard begins on days 180, 365 and 450. Andrew Feldman called an IPO “the beginning of adulthood”; Lemkin nevertheless worries that, as he understands the structure, last-round investors can put back almost $2B of stock if shares fail to trade 70% above the IPO price within two years. That deadline could invite shorts and sacrifice long-term decision-making to a fixed date.
Feldman’s warning on fashionable hardware and defense investing is that accumulated experience still matters. A chip tape-out can consume $20M-$30M in non-recurring engineering costs—and a bug means paying again—while defense requires trusted relationships, cleared personnel, specialized facilities and patience with “Bible-sized contracts.” Commercial technology can still reshape warfare, but procurement and cost-plus incentives remain the constraint.
🔗 Original source & video: 20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia’s 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech