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Private Equity Market Splits Between AI Company Premiums and Discounts for Older Software Companies

Phil Haslett of EquityZen says the private equity market has split between companies built around artificial intelligence, which sometimes command premiums, and older companies carrying 2021 financing rounds that trade at steep discounts. The secondary market, he says, offers an indicator closer to the realizable price than the valuations announced in financing rounds.

2026-08-25
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Private Equity Market Splits Between AI Company Premiums and Discounts for Older Software Companies

The secondary market for private-company shares has become more influential in the startup ecosystem as venture-backed companies remain private for longer periods. In an interview with Crunchbase News, Phil Haslett, EquityZen’s co-founder and head of strategy, explained how the prices of these transactions reveal a clear divide between newer AI companies and older software companies.

EquityZen, founded in 2013 and headquartered in New York, operates a marketplace for buying and selling shares in private companies, allowing employees and other shareholders to sell their stakes before an initial public offering or acquisition. Morgan Stanley announced plans to acquire the company in October 2025, before completing the transaction in January 2026.

The IPO Market Is Improving, but Success Is Not Guaranteed

Haslett describes the IPO market for late-stage technology companies as better than it was three or six months ago, benefiting from stronger technology stocks and an overall rising market. But he cautions that the picture remains mixed; some IPOs experienced initial enthusiasm followed by a slowdown, and he cites Cerebras as an example of a company whose performance declined after its listing.

The strength of IPO activity in the second quarter was also heavily tied to SpaceX, making it more difficult to assess how open the market is to the typical technology company. Nevertheless, Haslett believes artificial intelligence is creating opportunities across the production chain, from the energy needed for data centers and chips to coordinating computing resources and improving the cost of training and inference.

Why Do Some Companies Command a Premium?

EquityZen says the average transaction in the secondary market was completed at a 38% discount to the last financing round, while many transactions involving AI companies traded at premiums. Haslett attributes this to the existence of two different generations of private companies.

The first generation includes companies founded before the AI wave or forced to adapt to it. Many raised financing in 2021 at high valuations and then did not raise another round. Slower growth or a rebuilding of strategy affects the secondary price. By contrast, companies founded in 2023 and afterward with a mindset that places AI at the core of the product and operations may appear more efficient and clearer to investors, particularly when they raise successive rounds at higher valuations.

Haslett cites Airtable, which raised financing at a valuation of approximately more than $10 billion and was later sold for far less. This does not mean, in his account, that the company is bad, but its 20% growth appears less attractive when compared with newer companies that went from zero to hundreds of millions of dollars in revenue within a few years. He concludes that more companies from the 2021 era may be sold for less than their valuations from that period.

Financing, Time and Risk in Capital-Intensive Companies

The rise of AI infrastructure, robotics and space-technology companies reflects a substantive shift in investor interests, according to Haslett, rather than merely a pursuit of a limited number of rare stocks. But these companies generally need more capital and may take longer to reach predictable revenue, especially if they have to build a factory or obtain regulatory approvals.

Investors therefore discount the price to account for the cost of waiting and the need for additional financing. Haslett notes that the financing options available in 2026 have become broader than before, including credit and asset-based financing. However, these options introduce a different kind of risk: if performance weakens or assets are sold under pressure, creditors and lenders receive their claims before secondary-equity investors.

What Is Changing in Practice for Shareholders and Companies?

Liquidity programs are no longer limited to companies that were founded five, six or seven years ago. Smaller companies have begun using limited offers and structured share-buyback programs to reward employees and retain talent, particularly engineers and data scientists. Haslett believes that the availability of more tools, along with Morgan Stanley’s expansion in tender offers, has made secondary liquidity more acceptable to companies and investors.

But this balance could change if markets decline. The current environment, according to the interview, favors founders and employees, while investors are pursuing these transactions to gain stakes in companies they consider promising. A company’s ability to manage the program, find buyers and provide shares for sale remain practical factors that are not settled by the announced valuation.

For investors, the importance of the secondary price lies in the fact that it reflects what can actually be obtained at present, rather than merely the value of a previous financing round. The base valuation in a round measures investors’ willingness to purchase preferred shares that may include additional rights and liquidation preferences, whereas a secondary share does not necessarily offer the same advantages.

As for older software companies, Haslett links the return of some of them to premium trading to their ability to execute: using AI internally, integrating it into products, and leveraging customer loyalty and accumulated industry expertise. This is his view, not a proven rule for every company. But what the data presented in the article confirms is that the market no longer rewards a company’s name or previous valuation alone; instead, it tests the speed of adaptation, the clarity of the growth path, and the scale of financing and execution risks.

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