20VC: Anthropic Raises $13BN | Why Canva Will Not Direct List | OpenAI Buys Statsig for $1.1BN All Stock | Lovable Raising at $4BN + Vercel at $9BN: Justified or Not | Quarterly Results from SNOW, Mongo, ZOOM and more
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this episode of 20 VC, Harry Stebbings hosts Rory O'Driscoll and Jason Lemkin alongside Canva co-founder Cliff Obrecht for their weekly roundup of tech's biggest moves. They dissect Anthropic's massive $13B raise at $183B valuation (03:54), OpenAI's $1.1B acquisition of Statsig (16:37), and the resurgence of B2B SaaS companies with stellar earnings from Snowflake, MongoDB, Box, and Zoom. Obrecht shares insights on Canva's AI-driven reacceleration to $4B ARR growing at 40% (08:01), their billion-dollar cash balance, and IPO readiness strategy. The discussion explores AI's infrastructure demands, with Jensen Huang's $3-4T market projection (47:51), while examining whether current AI economics can sustain such massive capital deployment through real enterprise value creation.
Speakers
Harry Stebbings (Host)
Host of 20VC, one of the world's top venture capital podcasts. Previously founded The Twenty Minute VC, which became a leading voice in venture capital media.
Rory O'Driscoll
Venture capitalist and frequent co-host on 20VC. Known for his analytical approach to growth stage investments and deep expertise in SaaS valuations.
Jason Lemkin
SaaS industry veteran and Managing Director at Storm Ventures. Founder of EchoSign (acquired by Adobe) and SaaStr, the world's largest community of SaaS executives.
Cliff Obrecht
Co-founder of Canva, the $42 billion design platform with 240 million monthly active users. Has led the company through 13 years of growth while maintaining profitability for 8 consecutive years.
Key Takeaways
Raise Capital When You Don't Need It
Strategic fundraising isn't about desperation—it's about relationship building for the long haul. Canva's approach of maintaining an oversubscribed round while choosing investors based on IPO cornerstones and eighteen-month partnerships demonstrates sophisticated capital strategy. (08:30) "We're seeing this not as a point in time deal, but a relationship building exercise through the next eighteen, twenty four month period."
Build Products, Not Gimmicks
AI integration should accelerate core mission delivery, not create flashy features that fade. Focus on "workhorses, not gimmicks" that solve real workflow problems for existing users. (14:15) Early AI adoption syndrome can trap companies in unsustainable revenue models—prioritize crossing the chasm to mainstream adoption over Twitter-sphere buzz.
Embrace Spray-and-Pray AI Strategy Early
Run company-wide AI hackathons and test everything initially, then ruthlessly consolidate to high-value features. (14:44) Provide teams with multiple AI tools without being "the arbiter"—let natural selection determine winners while maintaining security standards. This approach drives genuine productivity gains before optimization.
Master the Double-Bet on Winners
When you identify category leaders executing at scale, overcome early-stage investor ego and bet bigger in later rounds. (67:58) The best Canva investors raised SPVs and additional vehicles to compound positions rather than claiming "discipline" by staying small. Two data points over time provide infinitely more signal than one.
Price AI Usage Like Utility Infrastructure
Implement hybrid seat-plus-consumption models as AI enables single users to produce exponentially more output. (58:59) One marketer can now deploy tens of thousands of content pieces—traditional per-seat pricing breaks at this scale. Build credit systems that protect margins while enabling power users.
Statistics & Facts
- Anthropic's revenue trajectory: from $100 million two years ago to $1 billion run rate at start of year to approximately $5 billion now, potentially reaching $8-9 billion by year end (9x revenue growth). (04:25)
- Canva will close the year very close to, if not at, $4 billion in revenue while growing at close to 40% growth rate and reaccelerating. The company has been profitable for 8 years and has over $1 billion cash on balance sheet. (07:57)
- 90% of Canva's user acquisition is organic, with the company reaching 240 million monthly active users. They experience billions of AI usages in their product per month, with images uploaded from ChatGPT growing from 0.02% a year and a half ago to over 5% now. (60:09)
- OpenAI acquired Statsig for $1.1 billion in stock (matching the last round valuation) for a company doing $75 million in ARR, representing approximately 15x revenue multiple.
- IBM found that 97% of organizations reported an AI security breach in 2025 alone, highlighting the risks of shadow AI usage by employees. (02:57)
