Why Insight Partners won't bet the farm on OpenAI

Devin Parekh on writing small checks early, selling into froth, and why funds stuffing 40% into one AI lab worry him.

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Sep 13, 2026

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Why Insight Partners won't bet the farm on OpenAI

Devin Parekh on writing small checks early, selling into froth, and why funds stuffing 40% into one AI lab worry him.

In brief

Devin Parekh on writing small checks early, selling into froth, and why funds stuffing 40% into one AI lab worry him. Diversification and liquidity beat concentration over a ten-fund horizon, even when concentration looks smarter this quarter. Originally reported by TechCrunch.

The quiet $90 billion firm

The quiet $90 billion firm

Devin Parekh has co-run Insight Partners for 26 years. While other VCs live on X and podcasts, Insight stays off the stage and lets the portfolio speak.

“Let the portfolio do the talking.”

AI risk, weighed honestly

Parekh grants that a non-state actor could misuse an open-source model to build a bioweapon. He thinks faster drug discovery is the more likely outcome, and he'll take that trade.

“There's a risk... But there's an even higher probability we get a massive decrease in the time it takes to develop new drugs.”

Fifty million patient records

On the NYU Langone board, he watched AI read 50 million records and flag a patient walking in for something unrelated with a 25% heart attack risk.

Aging population, too few doctors

He frames AI in medicine as a capacity problem, not a luxury. There aren't enough medical professionals to serve an aging population, so scale has to come from somewhere.

“We're going to need AI to scale healthcare.”

Not everyone is an expert

Parekh's read on VC noise: the same people became epidemiologists during COVID and geopolitics analysts during the Iran war. Insight communicates enough to be known, and stops there.

“Every venture capitalist thinks they're an expert on everything now.”

No fixed allocation

Early stage, growth, buyout and secondaries shift fund to fund. Look across Insight's last seven funds and the percentages never repeat.

“It's temporal, not fixed.”

Buyouts are cold

High rates, debt markets that won't touch software, and compressed exit multiples have shut the window. Insight hasn't done a major buyout since 2024.

Paying more for the same risk

Normally a follow-on round buys you more data, so a higher price reduces risk. Rounds now move so fast there's almost no new data, so you pay up and the risk stays put.

“you're paying more without reducing risk”

Go earlier, write smaller

The answer to frothy late rounds is a $20 to $25 million check instead of $500 million, then doubling down on the ones that work. That's where returns have clustered.

“That's where our returns have disproportionately come from.”

The Wiz math

Insight wrote Wiz's Series A and kept writing checks, multiplying the gain. Had it failed, the loss would have barely registered against a fund that size.

Talent went flat, mostly

A partner flew to Stockholm to pitch Legora because that's where the founder lived. But AI infrastructure talent still clusters in San Francisco, and fintech talent in New York.

“Talent has gone flat globally.”

Losing Legora, and shrugging

General Catalyst won that deal. Parekh's read is simply that they sold their value proposition better that time, and he doesn't need every win.

“It's a big world; we don't need to win every deal.”

Owning both OpenAI and Anthropic

Once you're late-stage, off the board and not touching governance, you're buying a great stock. At Series A or B, Insight still bars directly competing bets.

“Once you're at a later stage, off the board, not driving governance, you're just buying a great stock.”

Exclusivity died at $30 billion

When labs needed to raise $30 to $100 billion, they lost the power to demand exclusivity from investors. The consumer-versus-enterprise split between OpenAI and Anthropic is blurring too.

Robots are still science projects

Physical AI means betting on whether robotics adoption happens and then on when. Insight is watching, not buying. His 23-year-old VC son thinks that's crazy.

“you're making a bet on when robotics adoption happens, layered on top of a bet on whether it happens at all”

Funds with one holding

Funds with one holding

Parekh knows two funds raising their entire vehicle in a month on a pitch of putting 35 to 40% into a single AI lab. He's on fund 13 and thinks in terms of ten funds, not one.

“this business has always rewarded diversification over a long horizon”

Take your basis out

Many first and second-time funds won't raise again because they never returned cash. Insight sent back over $20 billion in two years through sales and IPOs.

“LPs want to know you can turn positions into cash; that's the job.”

De-risk 10 or 20 percent

When a founder gets a frothy offer, Parekh asks what happens at the correction he can't time. You don't have to sell everything to be sensible.

“you can't compound $40 billion at 50% every two months for two years without becoming the world economy”

Three trillion-dollar IPOs

SpaceX, Anthropic and OpenAI could all list within six to eight months. The real test is the next tier, and what bar a four-year run to $65 billion sets for everyone else.

“Eventually even these companies become normal-growth companies.”

The Armis $5 million check

Insight lost the deal to Sequoia but kept the relationship warm with a small check. Eighteen months later it bought out the whole cap table, then sold to ServiceNow for $7 billion.

“The goal is finding the best founders in the best markets.”

The takeaway

Diversification and liquidity beat concentration over a ten-fund horizon, even when concentration looks smarter this quarter.

Read the original on TechCrunch

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