Sep 4, 2025 · 1h 14m · news
Anthropic Raises $13BN & OpenAI Buys Statsig for $1.1BN All Stock · 20VC with Harry Stebbings
Rory O'Driscoll · 26m spoken Cliff Obrecht · 22m spoken Jason Lemkin · 10m spoken Harry Stebbings · 8m spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
This episode of the 20VC podcast features a roundtable discussion analyzing massive tech valuations like Anthropic's fundraise and OpenAI's acquisition of Statsig, alongside Canva's operational playbook, IPO preparation, and the structural impacts of AI compute costs on SaaS business models.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 12.8% of the talking time here. How this is scored →
Harry as informed peer 4.8 Guest teaching 4.8 Guest disagreement 2.1 Harry pushing back 3.6
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 46:09 Cliff rejects Harry's push for a direct listing
Cliff directly counters Harry's enthusiastic suggestion that Canva is the perfect candidate for a direct listing, citing data that historic direct listings fail to succeed post-listing.
Hardest push from Harry ▶ 27:57 Harry pushes back on Jason's valuation skepticismHarry rejects Jason's argument that rapid valuation step-ups are irrational, citing undisclosed revenue numbers and accelerated growth trajectories to defend the valuation.
Biggest teaching moment ▶ 20:45 Rory explains the financial engineering and audit write-down risk in the Meta-Scale dealRory provides an advanced lesson on the structure of Meta's Scale acquisition, explaining how VC cash cash-outs left Scale an empty husk prone to upcoming audit write-downs.
Harry holds his own ▶ 27:57 Harry demonstrates deep ARR data knowledge on LovableHarry demonstrates technical domain expertise by providing precise undisclosed ARR numbers and forward revenue multiples to challenge the panel's valuation skepticism.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Analyzing Anthropic's $13 Billion Valuation and Multiples | 3 | 5 | 1 | 2 | Harry introduces the Anthropic $13B raise and prompts Rory, who delivers a comprehensive forward-revenue multiple calculation. Harry asks how founders select capital during 5x oversubscriptions, keeping the dynamic collaborative. | |
| Canva's $1B Secondary and Valuation Compounding | 4 | 3 | 1 | 2 | Cliff details Canva's strategy for employee secondaries and selecting long-term anchor investors like Fidelity. Harry references Brian Halligan's perspective on Fidelity, demonstrating good context while letting Cliff lead. | |
| AI Product-Market Fit and Canva's Integration Strategy | 1 | 4 | 2 | 1 | Rory leads the questioning around AI user retention and enterprise renewal rates. Harry remains quiet as Cliff explains Canva's strategy of creating workhorses rather than gimmicks and consolidating enterprise AI tools. | |
| OpenAI's $1.1 Billion Statsig Acquisition | 5 | 4 | 2 | 4 | Harry takes control of the topic structure to highlight OpenAI's $1.1B purchase of Statsig, arguing the price is cheap for $75M ARR. Rory and Jason reframe the deal mechanics, showing how flat-round rollovers satisfy growth investors. | |
| Meta, Scale AI, and Zuckerberg's Mercenary Strategy | 5 | 5 | 3 | 4 | Harry prompts the panel on Meta's Scale AI investment and team departures, citing portfolio news. Rory delivers an incisive critique of the deal's empty shell structure and impending audit write-downs. | |
| Decoupling Valuation from Canva's Organic Reacceleration | 7 | 4 | 3 | 6 | Harry forcefully pushes back against valuation skepticism regarding AI startups like Lovable, quoting undisclosed ARR metrics. The panel engages in spirited debate over rapid step-up rounds and market validation. | |
| The Impact of "Foie Gras" Funding and Capital Discipline | 5 | 4 | 2 | 3 | Harry initiates a conversation on overcapitalized startups and asks if funding excess harms companies. The guests discuss capital discipline and contrast public SaaS stock recoveries with private market expectations. | |
| Public vs. Private Capital Costs and the Direct Listing Debate | 6 | 6 | 3 | 6 | Harry directly challenges Cliff on why Canva does not pursue a direct listing given its retail brand strength. Cliff refutes the idea, citing empirical data on post-direct-listing performance and the necessity of building long-term institutional relationships. | |
| Nvidia's Capex Capex and Canva's AI Margin Management | 6 | 5 | 2 | 4 | Harry brings up Jensen Huang's $3-4T capex projection and Notion's margin compression. Cliff explains how Canva manages AI compute overhead through custom models and tiered usage limits. | |
| Developer Agents and the Death of Seat-Based Pricing | 5 | 5 | 2 | 3 | Harry asks Cliff whether Canva would spend $10,000 per engineer monthly on AI coding agents. Cliff responds by explaining why seat-based pricing models must transition toward consumption-based hybrids as individual productivity scales. | |
| The Rise of LLM SEO and ChatGPT Referrals | 5 | 6 | 2 | 4 | Harry notes Monday's stock decline caused by SEO dependency and asks Cliff about Canva's acquisition channels. Cliff educates the panel on Canva's dominant position in LLM SEO and ChatGPT referral traffic. | |
| Foundations of AI and the Green Energy Catalyst | 6 | 7 | 2 | 4 | Harry asks Cliff to choose between top foundation model providers before sharing his own VC deal miss regrets. Rory delivers a detailed masterclass on overcoming loss aversion and paying the tax on two positive data points. |
Statements from this episode (43)
O'Driscoll: Buyers make no money in a perfectly priced direct listing
“No one wants to say it, but if you get the direct listing totally successful, the people buying don't make any money, right?”
O'Driscoll: Anthropic's valuation is 8-9x next year's revenue if growth persists
“The stunning thing with this growth rate, if it persists, big underline, is you're only buying in at eight to nine times next year's revenues if the growth lasts.”
Obrecht: Anthropic's $13B funding round was heavily oversubscribed and exclusive
“This round was also super oversubscribed. It was, I know folks in the industry have been clamoring over this and it was hard to get into.”
Obrecht: Canva at $42B Valuation Is Barely 10x Revenue
“Well, that's barely 10 X for us. We sound very cheap.”
Obrecht: Canva to hit $4B revenue at 40% growth rate
“We will close the year very close, if not at four billion growing, ah, close to 40% growth rate and re-accelerating growth.”
Obrecht: Fidelity is the largest check in Canva secondary round
“They're the anchor of the round. They're the largest check in this round.”
Obrecht: Canva holds over $1B cash and 8 years profitability
“We've got over a billion dollars cash in the bank. We don't need to raise money, primary funds. We've been a profitable company for eight years.”
Obrecht: Canva valuation dropped from $40B to $26B in 2022
“We in 20, 21 were worth forty billion dollars, which was a, I think it was a 50 X multiple on our revenue at the time. 20, 22, everything came crashing down. The market came crashing down and that took us down to 26.”
O'Driscoll: Sustained growth over 5-6 years rescues VC overvaluation
“In the end, the thing that bails out our incompetence is your growth rate, and that's the dirty little secret of the positive. If you get in these companies which can compound for five or six years, they can cover a multitude of cents.”
Rory O'Driscoll: Year-Two AI Renewal Rates Will Be Low
“Our nagging suspicion is that some of the year two ARR renewal rates for some of these AI products will be pretty low. In other words, that the AI product market fit is getting covered over a little bit by, you know, AI enthusiasm.”
Cliff Obrecht: Canva Uses Four Coding AI Tools, Led by Cursor
“We're running four coding tools at once, right? Cursor seems to be the one that's kind of leading the pack.”
Cliff Obrecht: Enterprise AI Tool Subscriptions Will Consolidate Within 24 Months
“Over the course of the next 12 to 24 months, we'll start consolidating down as the clear winners take charge, and so to answer your question that way, hundred percent there's going to be consolidation down from yeah, year two renewals.”
Lemkin: Late-stage investors do not care about small acquisition price changes
“You don't really care as a late stage investor. You don't care whether it's one or one Oh six or nine 84, because you're making the exact same amount.”
Lemkin: ICONIQ used Statsig acquisition as backdoor to invest in OpenAI
“Iconic rolls over a hundred million into open AI. They're not allowed to invest because they led the anthropic round. Right. So this is the only way they can put nine figures into it because they're soft band or hard band from the round.”
Obrecht: Canva has received acquisition offers but will remain independent
“I'm not doing it, but we love OpenAI. We love them, but there's just not, I mean, we're cutting our own course. We've had acquisition offers.”
Obrecht: Scaling companies must not treat user bases like wet tea towels
“One thing you need to buck the trend of as you become a larger company is insular thinking and treating your user base like a wet tea towel that you need to wring out.”
Lemkin: Anthropic revenue tripled in four months
“Anthropix revenue has tripled in four months, right?”
O'Driscoll: Anthropic grew revenue from $100M to $1B in 2024
“They went from a hundred to a billion last year.”
Lemkin: Replit raised at $3B valuation with similar $100M ARR to Lovable
“13 days later, the exact same company called Replit. That's the one I use. Same company closes at three billion. Basically the same ARR, basically the same company.”
Obrecht: Founders should stay overcapitalized rather than running ultra-lean
“This is a high risk maneuver and I don't recommend this to founders anymore. I say be a bit over capitalized, but we would run it kind of to the bones in order to take as little money as possible.”
Lemkin: SaaS founders without AI re-acceleration by late 2025 failed
“It's kind of sinful if you haven't re-accelerated by the end of twenty-twenty-five. You kind of failed as a founder because, yeah, you may miss some of the cool kids, right? They may not, they may be using, but you have a billion plus of distribution. You have…”
Obrecht: Canva is actively gearing up to be IPO-ready
“I mean, we're gearing up to be ready to IPO. We want to be an IPO ready company. We recently, you mentioned Zoom. We brought in Kelly, who led their IPO, and she's been a fantastic addition to the team. She was their CFO. So, so our goal is to be ready. When w…”
Obrecht: Employee liquidity is Canva's primary motivation for an IPO
“I think it's probably liquidity, and there are restrictions, particularly around employee liquidity and what you can do in the U.S. And whatnot around that piece. And so, We do believe in, we're 13 years old as a company. Our employees should have liquidity. T…”
O'Driscoll: Public markets offer cheaper capital than private markets
“The public markets now are giving me cheaper capital than the private markets, because if you're, if all the numbers are as reported, you're getting roughly 10 X revenues, and the fine folks at Figma are getting between 17 and 30, depending on how available yo…”
Obrecht: Canva has 240 million monthly active users
“We got two hundred and forty million monthly active users.”
Obrecht: No historical direct listing has succeeded in the short term
“And if you look at all the historic direct listings and how they've gone over time, I believe the data proves that none of them have been greatly successful. A lot of them have been really successful companies Over a long period of time, but that period post d…”
O'Driscoll: $4T AI infrastructure investment requires impossible $800B annual profit
“Four, let's do four billion dollars. You want a 20% return on equity. You gotta be generating eight hundred billion of profit a year. That's a lot of profit when, you know, Facebook met, all these guys make a couple hundred billion a year, right? So you've got…”
Obrecht: 90% of AI Queries Will Shift On-Device or Self-Hosted
“For the most premium queries where you need that answer, but 90% of it will be run on device or be self-hosted.”
Obrecht: Canva's AI Widget Generator Has 20 Million Active Users
“So, so we've got the equivalent of Lovable, it's more for creating widgets and for education purposes, et cetera. It's got twenty million active users already it's going really, really well.”
Obrecht: Canva Is Transitioning to a Unified AI Credit Model
“We're moving to a unified credit model around AI. So your premium subscription, free gets a certain amount, premium subscription gets you a certain amount. And then if you're a super active user, and so that means it can't eat into our margins too much. So you…”
Obrecht: Canva Is Price-Insensitive on AI Coding Tools for Engineers
“We encourage all our engineers to use the best security certified Coding tools that can increase the efficiency and we're not price sensitive around that at all.”
Obrecht: AI SaaS Pricing Must Shift to Hybrid Seat and Consumption Models
“You can't charge 20 bucks a seat for that level of breadth. So, so then it hits a certain, you give that functionality for a per seat price, but then over that, it needs to be based on consumption. So it's a hybrid seat and consumption based model.”
Obrecht: SEO now accounts for 15% of Canva organic acquisition
“SEO is about 50, 15% of the 90% organic to date, so it used to be our number one channel, but now our sort of like user flywheel, word of mouth, and people sharing designs are our biggest.”
Obrecht: Canva is ChatGPT's fifth most referred domain overall
“We're the number one productivity app on ChatGPT, and we're the fifth Highest domain that ChatGPT refers to.”
Obrecht: ChatGPT-generated images on Canva rose from 0.2% to over 5%
“A year and a half ago.2%, I think it was, of the images uploaded to Canva were from ChatGPT. That's now over five percent.”
Lemkin: SEO is only dead for companies without brand or value
“This whole thing about SEO being dead is, is stupid. It's dead for folks that don't have a brand, don't add value and don't have reach.”
O'Driscoll: AI search threatens media sites, not product companies
“In fairness, the kind of, the SEO, I think you have to distinguish between people like Canva where they have a product to sell and they're totally happy to sell it via ChatGPT, and then media companies where the only product they have is their content, where i…”
Obrecht: AI Energy Demand Will Accelerate Transition to Nuclear Power
“And so while I see AI pessimists and environmental pessimists saying, oh, so much more energy, it's going to be bad for the environment. I actually think it's going to rapidly accelerate our shift to green energy, particularly nuclear which we're just going to…”
O'Driscoll: I passed on Box in 2010 before investing nine months later
“Same thing on Box. I passed at the start of 2010. The round didn't even get done, and nine months later, I literally woke up and said, what's the dumbest thing I did all year? I didn't do that deal, and I went down and did it.”
Obrecht: Early investors who raised SPVs for late rounds saw highest returns
“And the best investors that have done best out of Canva, like they were early stage funds, but they realized, holy shit, we're onto something here. So they raised SPVs or additional vehicles to move further up the value chain, like going later and later stage …”