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Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging”

Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others. Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more. ----------------------------------------------- In Today’s Episode We Discuss: 00:00 Intro 00:59 Figma's IPO: Rule of 80, $1.5B in cash, 40% margins 02:48 Adobe Screwed the Deal: Should They Have Just Bought Canva? 14:17 Pay-to-Play Deals: Heroic Hail Mary or Guaranteed Write-Off? 19:01 How Index Is Returning $3.5B on 2 Deals 24:22 Melio’s $2.5B Exit: Insane Growth… So Why Did They Sell?! 33:08 Massive Penthouses and the Death of Focus: AI Founders Beware 40:14 Chime, Anthropic, Menlo & The Art of Selling LPs the Future 43:06 Couchbase Acquired: PE Buyers Are Back… Or Are They? 46:45 Why No One’s Buying These 9-Figure SaaS Zombies 52:02 If You Didn’t Grow from AI By June 30, You’re Already Dead 53:42 Superhuman vs The AI-Natives: Who Wins the Replatforming War? 58:52 Oracle's $30B AI Deal: Larry Did It Before You Even Started 01:01:01 Scale Is Dead. Long Live Surge. The AI Data War Gets Bloody. 01:05:34 Asana CEO Move & the Great Founder Exodus of 2025 01:12:14 Kalshi Quick-Fire Round ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: / harrystebbings Follow Jason Lemkin on X: / jasonlk Follow Rory O’Driscoll on X: / rodriscoll Follow 20VC on Instagram: / 20vchq Follow 20VC on TikTok: / 20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #ai #figma #oracle #adobe #aistartup #melio

Jason LemkinguestRory O’DriscollguestHarry Stebbingshost
Jul 2, 20251h 15mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Figma’s IPO, Melio’s sale, and AI’s brutal new venture math

  1. The episode dissects Figma’s S-1, arguing it’s a rare billion‑dollar ARR, rule‑of‑80 SaaS asset that validates Adobe’s aborted $20B acquisition and will strongly reward early investors like Index. They contrast this with Melio’s $2.5B sale to Xero, seeing it as strategically logical yet discouraging on a revenue multiple basis and a warning about late‑stage valuations and preferences. The conversation then widens into how AI, massive capex, and winner‑take‑most dynamics are reshaping venture: reserves, down rounds, PE exits, roll‑ups, founder secondaries, and why being “AI native” (or at least AI‑relevant by mid‑2024) is now existential. They close on the surge of CEO turnover, mega‑funds like Menlo’s, the hollowing out of mid‑tier outcomes, and examples like Oracle and Vlex showing who is actually making the AI transition versus who is getting left behind.

IDEAS WORTH REMEMBERING

5 ideas

Figma is a once‑in‑a‑cycle SaaS IPO that retroactively justifies Adobe’s ‘overpriced’ bid.

With ~$821M revenue, ~46% growth, strong free cash flow, and rule‑of‑80 performance, Figma could list near or above the prior $20B Adobe deal, validating Scott Belsky’s push to buy it and showing how high-quality, scaled SaaS can still command premium multiples.

Melio’s $2.5B exit looks strategic but is worrying as a benchmark multiple.

At roughly $150–200M ARR and triple‑digit historical growth, selling for ~13–15x revenue is not a blowout in today’s AI‑inflated world; it highlights how crowded, slower‑growth fintech categories and heavy pref stacks compress returns and challenge assumptions about $1–3B ‘mid-tier’ outcomes.

Reserves and down‑round ‘rescues’ rarely create home runs; time is the real opportunity cost.

They argue follow‑ons disproportionately go to fastest growers, but ex‑post many expected fund‑returners aren’t; pay‑to‑plays and messy down situations generally cap upside at modest multiples while consuming huge partner time that could be better spent on new winners.

AI is driving an extreme winner‑take‑most regime—both in startups and in venture funds.

LPs understand the math: jumbo funds now require multiple multi‑billion‑dollar outcomes, and capital is concentrating into a tiny set of AI leaders (Anthropic, Cursor, etc.), making missing those deals far more damaging than overpaying at seed or Series A to get in.

Being AI-native—or at least AI‑relevant by mid‑2024—is increasingly a survival threshold.

Their heuristic: if your product and growth haven’t materially improved from AI by now, you’ve effectively failed; examples like Intercom, Airtable, Vlex, and even Oracle show legacy players can adapt quickly, but many SaaS companies are already past their window.

WORDS WORTH SAVING

5 quotes

If you haven’t grown because of AI, you’ve failed.

Jason Lemkin

If Oracle can get AI native by June 30th and your startup can’t, I mean, I’ll smile, but I’d give up.

Jason Lemkin

Everything goes back in life to incentives… if your board member can’t speak to the money anymore, they’re basically useless.

Rory O’Driscoll

The late‑stage business is a lovely rigged game: if you always get a 1x on your losers and have enough winners, by definition you have a positive IRR.

Rory O’Driscoll

Pessimists sound smart and optimists make money.

Rory O’Driscoll

Figma’s S-1, valuation debate, and Adobe’s failed $20B acquisitionMelio’s $2.5B sale to Xero and implications for M&A and late-stage investingVenture reserves strategy, down rounds, pay‑to‑play and bridge financingFund sizes, LP expectations, and the winner‑take‑most dynamics in AIPrivate equity, roll‑ups, and the thin exit market for mid‑scale SaaSAI-native vs legacy software: who adapted in time and who failedFounder/CEO burnout, secondaries, incentives, and rising executive turnover

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