We’re back on 20VC+SaaStr, and its a great one as Canva Co-Founder and COO Cliff Obrecht joins Harry, Rory and Jason for a deep dive into this week’s biggest venture deals, AI infrastructure spending, and the return of public SaaS valuations. And why Canva won’t direct list.
Bottom Line Up Front
Cliff Obrecht (Canva COO): “Wall Street is the madman in the back seat. In the end, the thing that bails out our incompetence is your growth rate. We’ve had a billion sitting on our balance sheet for ages — that’s a flex, people.”
Jason Lemkin (SaaStr): “If you have a billion dollar installed base, you have a distribution channel. It’s kind of sinful if you haven’t reaccelerated by the end of 2025 — you kind of failed as a founder because you have no excuse. You had 18 months.”
Rory O’Driscoll (Scale Venture Partners): “Even if Anthropic goes from $9B ARR to $30B (3x growth down from 10x), that’s 8x next year’s revenues. High absolute number? Absolutely. Does it make sense if the growth persists? It’s not crazy.”
Harry Stebbings (20VC): “Most VCs should have had Anthropic’s trajectory in their model 47 days ago. These companies are out-accelerating plan, but you’re always valuing future growth.”
The $13B Anthropic Round: Math That Actually Works
Anthropic’s latest funding round grabbed headlines not just for its size — $13 billion at a $183 billion post-money valuation — but for what the math reveals about AI company valuations when you dig deeper.
“I went into the analysis expecting to say ‘aren’t those guys so silly paying so much?'” admits Rory O’Driscoll. “But when you look at the numbers, maybe those guys are being quite smart.”
The trajectory is staggering: from $100 million two years ago to a $1 billion run rate at the start of this year, now approaching $8-9 billion by year-end. If accurate, this represents roughly 9x revenue growth in a single year.
O’Driscoll’s forward-looking analysis reveals why investors were fighting to get in: “Even if they decelerate from 10x to 3x growth next year — going from $9B to $30B ARR — the average revenue would be around $20B. That’s 8x next year’s revenues if the growth persists.”
The round was massively oversubscribed, with demand reportedly 5-10x the amount raised. For growth-stage investors, sitting out seemed impossible. “If you’re a growth stage investor, it’s hard to imagine a world where you say ‘well, we’re growth stage investors but the two largest market cap companies in the last 3-5 years are the two LLM models and we don’t have a piece of that,'” notes O’Driscoll.
OpenAI’s Strategic Statsig Acquisition
On the same day, OpenAI announced its acquisition of Statsig for $1.1 billion in stock — exactly matching the company’s last funding round valuation from Iconic Ventures. With Statsig generating $75 million ARR, the deal represents roughly 15x revenue multiple.
The acquisition makes strategic sense beyond the numbers. Statsig’s CEO now ranks as #3 at OpenAI, and with Figma’s CEO joining OpenAI’s leadership, the company is assembling serious product talent.
“The fact that it was exactly the price of the last round shows this was something that everyone wanted to roll into,” observes O’Driscoll. For Iconic, which led Anthropic’s previous round and was blocked from OpenAI’s direct investment, this provided a backdoor into the OpenAI ecosystem.
The Return of Public SaaS: Snowflake, Zoom, and the AI Tailwind
Public SaaS companies delivered a surprise comeback this quarter, with Snowflake leading the charge with a 45% stock jump after reporting 24% year-over-year growth — a significant reacceleration from previous quarters.
“It’s the Mark Twain reports of my debt were greatly exaggerated,” quips Rory. “Well, it turns out reports of the death of SaaS and software were greatly exaggerated.”
The winners weren’t universal — MongoDB, Box, Elastic, Okta, and Zoom all posted strong results, while others like Salesforce haven’t yet seen the AI benefit flow through to revenue.
“Some folks, about half of the public B2B leaders, are finally getting an AI tailwind,” says Lemkin. “Box should be crushing it because every time I spin up a new AI app, I need like two or three databases.”
The market reaction reveals how beaten down expectations had become. When companies like Snowflake delivered even modest beats against lowered expectations, investors responded dramatically.
AI Infrastructure: The $4 Trillion Question
Jensen Huang’s prediction of $3-4 trillion in AI infrastructure spending over the next five years sparked intense debate about whether such capex levels can generate sufficient returns.
“Look at $4 trillion — you want a 20% return on equity, you’ve got to be generating $800 billion of profit,” calculates O’Driscoll. “That’s a lot of profit when Facebook and Meta combined make a couple hundred billion a year. You’ve got to believe you’re going to create another four Microsofts, another four Facebooks to justify that kind of spend.”
The discussion revealed how AI costs are already impacting SaaS margins. Notion famously went from 90% to 80% gross margins, effectively paying a 10% “GPU tax” on their revenue.
Canva’s Obrecht confirmed similar impacts: “100% yes, it already is [10% of revenue]. If you look at Lovable, their pass-through to Anthropic or model providers will be way more than 10%.”
However, Obrecht expects optimization over time: “We’re betting on distilling these models down, understanding user queries and where I need the frontier model versus where I can deploy the model that’s on-device or self-hosted. Companies will get better at picking the right model for the right job.”
Canva’s Path to IPO: Billion-Dollar Balance Sheet, 40% Growth at Scale
Obrecht provided rare insights into Canva’s current trajectory and IPO preparations. The company will close the year “very close if not at $4 billion” in revenue, growing at nearly 40% and reaccelerating.
“We have a lot of long-term partners and you want to pay loyalty to people that have supported you along the way, but we’re also thinking through what an IPO looks like,” Obrecht explained about their current secondary round approach.
With over a billion in cash and eight years of profitability, Canva doesn’t need primary capital. The challenge became managing a supply-demand imbalance when employees wanted to sell after seeing Figma’s public debut.
On timing, Obrecht noted: “We’re gearing up to be an IPO ready company. When we actually go out is another question, but we want to be ready.”
The company faces the classic late-stage private company dilemma. “What is the real difference?” asks Obrecht about staying private versus going public. “As a late stage private company with all the big institutions already invested and continuing to do so, our reporting obligations and expectations to beat and raise are pretty much the same.”
The Liquidity Challenge
Obrecht was candid about the limitations of private market liquidity solutions: “There’s availability to capital which we have access to. I think it’s probably liquidity and there are restrictions particularly around employee liquidity and what you can do in the US and whatnot around that piece.”
The 13-year-old company recognizes the fairness issue: “We’re 13 years old as a company. Our employees should have liquidity. They’ve created all this value. How can we make it easy for them to access that wealth that’s built up?”
But secondary markets aren’t a perfect substitute for public liquidity: “While secondaries, annual secondaries are a mechanism for that, it’s pretty janky and particularly in some jurisdictions, it’s downright impossible.”
This creates the awkward dynamic where employees need permission from their employer to access liquidity they’ve earned through years of value creation. “Having to get permission from your employer to get liquidity as a secondary after 13 years — it’s better than no liquidity but it’s a little bit serf-like,” notes one participant. “When you’re public you can make your own choices.”
The AI Integration Reality
Canva’s AI integration offers a window into how established SaaS companies are navigating the transition. “AI is just accelerating [our mission] massively, making it quicker, faster, and better for customers to achieve their goals,” says Obrecht.
The company is moving to a unified credit model for AI features, with free users getting limited credits, premium subscribers getting more, and heavy users paying usage-based pricing beyond certain thresholds.
“We’ve got 240 million users. We’re about to launch in October a whole slew of new AI products deeply integrating it into every part of the workflow. We need to seriously run the math on if 20%, 50%, 80% of our users use this 10 times a month — the costs can look pretty big and eat into margins very significantly.”
The VC Psychology of Missing Out
The conversation revealed fascinating insights about venture capital psychology around “the ones that got away.” Multiple participants shared examples of passing on companies early, then struggling to invest at higher valuations later.
“Many of my most successful deals I’ve passed on prior,” admits O’Driscoll. “When you see the company say they’ll do A, B, and C, you pass because you don’t believe they’ll do A, B, and C, and then they do A, B, and even C prime — you have what you need to know.”
The key insight: “The difference in information content between two data points over time, both of which are positive, and one data point where you have no calibration is almost infinite.”
Obrecht observed this pattern with Canva investors: “The best investors that have done best out of Canva 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, going later and later stage and compounded their position.”
Key Takeaways
1. AI Valuations Aren’t As Crazy As They Look Forward revenue multiples for companies like Anthropic become reasonable when you factor in sustained hypergrowth trajectories.
2. Public SaaS Is Back, But Selectively. Companies with distribution advantages and AI integration are seeing real reacceleration (Snowflake, Datadog, Box, Okta, GitLab even Zoom), while others remain stuck.
3. The 10% GPU Tax Is Real SaaS companies are already spending 10%+ of revenue on AI inference, but optimization will bring costs down over time.
4. Private-to-Public Arbitrage Exists Again Public markets are now valuing companies higher than late-stage private markets in many cases.
5. Don’t Let Pride Stop Follow-On Investments The biggest VC returns often come from doubling down on companies you initially passed on after seeing execution.
Quotable Moments
“If Zuck’s not feeling great about his AI strategy, he can cry into his $200 billion and get over it on his own, right? Take it up with a therapist.” — Rory O’Driscoll on Zuck’s Meta challenges
“We’ve had a billion sitting on our balance sheet for ages — that’s a flex, people.” — Cliff Obrecht on Canva’s financial position
“Wall Street is the madman in the back seat. In the end, the thing that bails out our incompetence is your growth rate.” — Cliff Obrecht on market volatility vs execution
“If you have a billion dollar installed base, you have a distribution channel. It’s kind of sinful if you haven’t reaccelerated by the end of 2025.” — Jason Lemkin on AI tailwinds for established SaaS companies
“It’s a bit embarrassing as an early stage investor to buy Revolut off Goldman Sachs. That’s when you really fuck up as an early stage investor.” — Harry Stebbings on VC regret psychology
