The Insight Partners diversification strategy has become a quiet point of distinction in a venture market where a handful of firms are staking enormous proportions of their new funds on OpenAI and Anthropic alone. Deven Parekh, who has co-run the firm for 26 years, sat down with TechCrunch at a StrictlyVC event in New York and was unusually candid about what that discipline looks like in practice, including the deals Insight lost, the ones it won bigger than expected, and why he thinks the math of extreme concentration simply does not work over time.
The Case Against Betting the Farm
OpenAI and Anthropic absorbed roughly half of all venture dollars in the first half of this year. Parekh has heard the pitch directly: he says he is an LP in two funds currently raising their entire vehicle in a month, with 35 to 40 per cent of each earmarked for one of those two companies. He is not dismissive of the underlying businesses, but he is sceptical of the strategy.
‘This business has always rewarded diversification over a long horizon,’ he said. ‘We’re on fund 13, so we have to think in terms of ten funds, not one.’ He acknowledged the short-term cost plainly: ‘In this particular moment, if 25% of our fund were in Anthropic, our returns would look better.’ The longer data series, in his view, does not support it.
Insight holds stakes in both OpenAI and Anthropic, a combination that would once have been considered a conflict of interest. Parekh frames it as a function of stage. Khosla led OpenAI’s Series A and could not then back Anthropic; had Insight led Anthropic’s Series A, the reverse would have applied. By the time Insight invested, neither company could any longer dictate exclusivity: they were raising between $30 billion and $100 billion at a time. ‘Once you’re at a later stage, off the board, not driving governance, you’re just buying a great stock,’ he said. Insight saw OpenAI as the dominant consumer play and Anthropic as having a clear enterprise strategy, though he notes that distinction is shifting.
The firm’s current fund cycle also reflects the cautious mood. In January 2025, Insight closed its thirteenth flagship fund alongside a dedicated buyout co-invest vehicle and a structured equity fund called Opportunities Fund II, raising a combined $12.5 billion, considerably smaller than the $20 billion Fund XII that preceded it. Insight’s own employees represent the largest aggregate commitment to the new funds. With $90 billion in assets under management across its history, the firm has backed more than 900 companies worldwide and seen over 55 reach a public listing.
On current valuations, Parekh is blunt. Follow-on rounds are moving so fast that investors are paying more without receiving the incremental data that normally justifies a higher price. His response is to go earlier, writing a $20 to $25 million cheque rather than $500 million, and compounding hard on the companies that prove themselves. ‘You can’t compound $40 billion at 50% every two months for two years without becoming the world economy,’ he said. ‘That math doesn’t work.’
Armis, Legora, and the Art of Staying Patient
The Insight Partners diversification strategy shows up most clearly in how the firm handles individual bets over time. The Armis story is the firm’s own best example. Insight lost the initial deal to Sequoia, but a partner kept the relationship alive with a $5 million cheque out of an $11 billion fund. Eighteen months later, the firm bought out the entire cap table, including Sequoia’s position, for a nine-figure sum.
ServiceNow has agreed to acquire Armis for $7.75 billion in cash, its largest acquisition to date, with the deal expected to close in the second half of 2026 subject to regulatory approvals. The snippet cited $7 billion; the definitive agreement figure is $7.75 billion. At the time of the announcement, Armis had surpassed $340 million in annual recurring revenue, with year-on-year growth exceeding 50%, and around 950 employees are expected to join ServiceNow on close.
Not every deal goes Insight’s way. Parekh volunteered the loss of Legora, the AI legal-tech company (formerly known as Leya, rebranded in February 2025) that counts General Catalyst as its lead backer. Jeff Horing flew to Stockholm to pitch the founders personally. Legora went on to raise an $80 million Series B co-led by ICONIQ Growth and General Catalyst at a $675 million valuation, following a $35 million Series A. General Catalyst co-led that round alongside ICONIQ Growth. Parekh’s assessment of why Insight lost was short: ‘I think they sold their value proposition better than we sold ours that time.’
Liquidity is the other pressure point. Over the past two years Insight has returned more than $20 billion to LPs through sales and IPOs, with more to come, and recorded a record year of exits with total realisations exceeding $8 billion including sales to Mastercard, Salesforce, and SAP. Parekh’s advice to other managers is consistent: even if a position looks set to triple, take your basis out. LPs need to see cash, not marks.
With Anthropic expected to file for an IPO soon and OpenAI likely to follow, Parekh thinks the public market will absorb both, alongside SpaceX, within six to eight months. The harder question, in his view, is what valuation bar those listings set for the tier of companies below them. For a public-market investor watching something go from zero to $65 billion in four years, ordinary compounding starts to look ordinary indeed.
