3 quotes from 1 episode on 20VC with Harry Stebbings, each with a timestamped link to the source.
3 quotes1 episode
The short version
Evaluating AI startups requires strict limits on revenue projection horizons. Sameer Dholakia caps valuation models at 12 months, refusing to pay for 18 or 24 months of future growth even when companies command 15 times forward revenue.
Most interesting insights
A larger check for the Anthropic funding round remains a missed opportunity for Sameer Dholakia.
“I wish I had the ability to convince us all to do a bigger check that round.”
Sameer Dholakia, 20VC with Harry Stebbings · October 2026 · Watch at 8:07 ↗
Future revenue projections hit a wall at 12 months
Valuation models hit a strict 12-month cap during the diligence process. The underwriting framework refuses to pay forward 18 or 24 months for startups priced at 10 to 15 times forward revenue.
“I'll go NTM next 12 months. And yeah, depending on the business, next 12 months only. Because you know, depending on where you are in the year and that could be more like 18 or 24 months and I won't pay that far forward.”
Sameer Dholakia, 20VC with Harry Stebbings · October 2026 · Watch at 17:35 ↗
Frontier models resemble the early cloud hyperscaler market
The diligence process for Anthropic relied on comparing AI development to the cloud era. The analogy anticipates the market narrowing to a few heavily capitalized winners partnered with major platforms.
“This is going to be a cloud redux was my analogy. In the cloud era, you had a handful of hyperscalers. You have AWS and Azure and GCP.”
Sameer Dholakia, 20VC with Harry Stebbings · October 2026 · Watch at 5:57 ↗
Bessemer Venture Partners invested in Anthropic's Series D at a valuation of $15 billion pre-money and $18 billion post-money.
Partner Byron Deeter told Sameer Dholakia that Anthropic was the lowest-voted deal in his history at the firm, proving that top venture returns require backing unconsensus convictions.
Bessemer raised $5.75 billion on the thesis that artificial intelligence represents a larger supercycle than the internet and cloud combined.
Backward ARR multiples make early rounds look impossible, such as paying 150x ARR for Anthropic or pricing Legora at $1.8 billion on $20 million in ARR.
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