20VC Newsletter - 25th October 2026
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20VC Newsletter - 25th October 2026
Here are the transcripts and top takeaways from 20VC episodes released this last week.
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Monday’s episode with Sameer Dholakia, Partner @ Bessemer:
Download the full transcript:
My 7 key takeaways:
This Is a Supercycle Like Never Before
Sameer has spent 31 years in software and has felt magic only a handful of times. A trillion-dollar supercycle followed every one of those moments, and he notes that it does not happen very often.
Capital Is a Moat Today
Markets pick winners and the choice becomes a self-fulfilling prophecy, as it did when developers settled on SendGrid and Twilio. In legal AI, big law firms name just two major providers. Capital lets leaders scale at an extraordinary pace and build a brand, which draws talent and customers in a reinforcing flywheel.
Who Wins and Who Loses in the Future of Venture Capital?
As industries professionalize, firms must be either a giant global platform that consolidates or an extreme specialist, such as an early-stage AI investor in San Francisco. Sameer counts Bessemer as a big global platform. Firms caught in between face a hard world to make money.
The Rationale for Why Anthropic Would Compete With the Hyperscalers and Why We Invested
As in the cloud era, AI would be massively capital intensive, so it would consolidate to a handful of players with hundreds of apps on top. Microsoft had partnered with OpenAI and Google was building Gemini, while AWS had an undistinctive internal model and had just invested heavily in Anthropic.
Why Price Does Not Matter in a World of AI and the Metric That Truly Determines Value
Bessemer invested in Abridge at $5M of ARR for a $700M to $800M valuation, in Anthropic at roughly 150 times current ARR, and led Legora’s $1.8B round at $20M of ARR. Sameer judges these deals on what the company can become in the next twelve months.
Why the Rise of Open Models Does Not Denigrate the Market for Closed Models
In a market this large, predicting the mix between closed and open tokens with any precision is irrelevant. Consumers, enterprises and governments will all want different flavors of intelligence. Bessemer has invested in both Anthropic and Fireworks to hold exposure to closed and open tokens.
Why It Is a Permanent Structural Shift That Companies Will Stay Private for Longer, but Why It Will Open in 2028
With more dollars and more firms in private venture, companies will stay private longer, and most of the run-up in this boom will happen in private markets. Sameer still expects an unlock in IPOs later next year and in 2028.
Thursday’s episode with Rory O’Driscoll, GP @ Scale, Jason Lemkin, Founder @ SaaStr:
Download the full transcript:
My 7 key takeaways:
Why Fundraising Is Back to Being a Numbers Game
Founders with top-decile numbers now have to meet 100 VCs, as in the old days. It will not be Benchmark, Index, Andreessen or Bessemer, but other growth investors will take the bet at a reasonable but still elevated valuation because it is the best deal they have seen that quarter.
Why the Big Funds Have to Have Billion-Dollar Positions to Make It Worthwhile?
A $5B plus fund needs $BN positions in everything. Without 51% ownership, which most founders will not accept, a $2B Listen Labs is not good enough, while 1% of Anthropic could still get there even with dilution.
Why Are CoreWeave and Oracle B-Tier and What Does That Mean for Their Price Volatility?
With massive debt loads, CoreWeave and Oracle should be hypersensitive to any bump at Anthropic or OpenAI. CoreWeave exists because NVIDIA needs it for now, and Oracle rents out excess capacity because it cannot sell enough enterprise software.
Why the Best Markets for App Layer Companies Compete Directly With the Models
The fastest-growing AI apps, such as code generation, code review and legal, sit closest to the foundation models. That brings a moment of terror every six months, but it is also why companies like CodeRabbit are growing faster than ever.
Why Code Review Is the Single Most Important Category in Software
AI-generated code is pretty good but never production-ready, and reviewing it takes an order of magnitude more time than building it. Getting code into production matters more than generating it, so the best code review teams would be worth 10 bets.
How Big Is the Market for Inference Truly?
The key inference providers add up to roughly $5B to $6B in run-rate revenue, under 5% of OpenAI and Anthropic combined. If tokens are roughly the same, Replit would rather pay Modal a 30% gross margin than give Claude Code 70%.
Why Bending Spoons Is a Berkshire Hathaway of Software
Bending Spoons buys software to hold, the way Warren Buffett wanted to hold See’s Candy forever. It made Vimeo and Evernote work with price increases, and with Miro and Airtable the quality of its assets is improving.
Saturday’s episode with Naveen Rao, CEO @ Unconventional AI:
Download the full transcript:
Let us know what your big takeaways from this week’s shows were in the comments below!
Thank you for reading, and don’t miss the great guests we have next week:
Monday episode: Satya Nadella, CEO & Chairman @ Microsoft
Thursday episode: Jason Lemkin & Rory O’Driscoll
Saturday episode: The Memo
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