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Tech and Science

Why AI startups are selling the same equity at two different prices

Last updated: March 3, 2026 5:05 pm
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In the competitive landscape of AI startups, founders and venture capitalists are exploring innovative valuation strategies to establish a sense of market dominance. Traditionally, startups would undergo multiple funding rounds with increasing valuations. However, this constant fundraising can divert focus from product development. To streamline the funding process, leading VCs have introduced a new pricing model that combines two funding cycles into one.

An example of this approach is seen in Aaru’s Series A funding round. Redpoint led the investment, allocating a significant portion at a $450 million valuation, and a smaller portion at a $1 billion valuation, attracting other VCs to join at the higher price point. This tactic enables startups like Aaru to attain unicorn status, valued at over $1 billion, despite acquiring a substantial portion of equity at a lower price.

The inflated headline valuation serves as a strategic move to deter other VCs from investing in competitors. This tactic has been met with surprise by many investors, as it deviates from conventional funding practices. Wesley Chan of FPV Ventures views this strategy as indicative of bubble-like behavior, comparing it to selling the same product at different prices, a practice typically seen in the airline industry.

While top-tier VCs often receive discounted rates due to the signaling effect of their involvement, oversubscribed rounds have led startups to accommodate excess interest by offering premium prices to additional investors. This ensures a coveted position on the cap table and addresses the challenge of turning away eager investors.

Another example of preferential pricing is seen in Serval, an AI-powered IT help desk startup, where Sequoia invested at a lower valuation but announced a higher valuation for the Series B round. While the high headline valuation may attract talent and corporate clients, it also poses risks. Startups are expected to raise subsequent rounds at valuations higher than the headline price to avoid a punitive down round, which can impact ownership percentages and stakeholder confidence.

Jack Selby of Thiel Capital warns against chasing extreme valuations, citing the market reset of 2022 as a cautionary tale. Founders must tread carefully to maintain a balance between perceived value and sustainable growth. As the AI startup ecosystem evolves, innovative valuation mechanisms will continue to shape the investment landscape, emphasizing the importance of strategic decision-making in securing long-term success.

TAGGED:equityPricessellingStartups
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