Bessemer's Dholakia: Anthropic Was Our Least-Loved Deal

Sameer Dholakia, a partner at Bessemer Venture Partners, says Anthropic was the least-loved deal in his firm's portfolio — and that the venture capital industry is now splitting in two.

Dholakia made the remarks in an interview published by BigGo Finance under the headline "Bessemer's Sameer Dholakia: Anthropic Was Our Least-Loved Deal, and Venture Is Splitting in Two." The claim is striking precisely because of who makes it. Bessemer is one of venture capital's oldest firms, and Anthropic has become one of the most valuable private companies in the world.

The takeaway: even a winning position can rank last on an investor's own affection scale. Dholakia's framing separates how a deal performs from how a firm feels about it — a distinction he draws deliberately.

What did Dholakia actually say about Anthropic?

He called Anthropic Bessemer's "least-loved" deal. That is the quote, and it carries the story.

The phrasing matters. He did not say Anthropic was the worst-performing investment. He said it was the least loved. In venture-speak, that gap is the whole point: a firm can hold a stake in a category-defining company and still feel ambivalent about how the position came together, what it cost, or the terms attached to it.

Dholakia did not elaborate, according to the published interview, on which of those factors drove the ranking. What readers get is the verdict, not the anatomy.

The one-line version: Bessemer's own partner puts Anthropic at the bottom of his firm's affection list, and that's the headline fact.

Why does "venture is splitting in two" matter?

Dholakia's second claim is structural. He argues venture capital is dividing into two businesses — not drifting, splitting.

That thesis fits a pattern the industry has debated for several years. Mega-funds raise ever-larger pools and write ever-bigger checks into late-stage and AI companies. Smaller funds concentrate on early rounds, where ownership stakes are cheaper and dilution is the enemy. The middle — firms trying to do both — gets squeezed.

Dholakia's contribution is to sharpen that observation into a binary. Two businesses, not one industry with a spread of strategies. If he's right, the operational implications are concrete:

• Fund sizes diverge rather than cluster
• Team structures and compensation follow the strategy, not the brand
• Exit expectations — timeline, return multiple, route to liquidity — reset around each model

The interview headline doesn't spell out which side Dholakia thinks wins. It states the split.

The one-line version: the industry's middle ground is disappearing, and Dholakia is calling the break explicitly.

What should Bessemer's LPs and founders take from this?

For limited partners, the comment is a signal about how one of venture's established firms reads its own book. A partner publicly ranking a high-profile AI position as least-loved suggests internal conviction about deal quality that doesn't track headline valuations.

For founders, the message is subtler. Capital from a marquee firm doesn't guarantee that firm's enthusiasm. If Bessemer grades Anthropic — Anthropic — low on its own love scale, then founder-investor fit deserves as much diligence as the term sheet.

For the broader market, Dholakia's two-ventures thesis sets a test. Watch whether firms keep splitting their strategies, or whether the bifurcation he describes forces consolidations, spinouts and repositioning across the next fund cycle.

The one-line version: affection and performance aren't the same line item, and the industry that funds them is coming apart at the middle.