In the high-stakes world of AI fundraising, speed and headline numbers matter more than ever. A new tactic is emerging that lets founders announce eye-popping “unicorn” valuations while quietly giving lead investors a sweetheart deal.
The playbook: structure the same funding round with multiple valuations — a lower one for the lead investor (often a top-tier firm), and a significantly higher “headline” valuation for everyone else who joins shortly after.
Two high-profile examples from late 2025 illustrate exactly how it works.
Case 1: Serval — From $235M to $1B in Months
Serval, an AI-native platform for enterprise automation and service management (starting in IT support and expanding to HR, finance, legal, and more), was valued at around $235 million in August 2025.
By December 11, 2025, the company announced a $75 million Series B led by Sequoia Capital at a $1 billion valuation — making it an instant unicorn less than two years after founding in 2024.
But according to The Wall Street Journal, Sequoia did not invest at $1 billion. Sources told WSJ the firm bought in at a $400 million valuation. Just days later, other investors joined the round at the much higher $1B mark.
Result: Sequoia gets immediate paper gains, the company gets a shiny unicorn headline to attract talent and future capital, and follow-on investors pay a premium for the “hot” status.
Case 2: Aaru — Headline Unicorn with a Split Reality
Aaru, an AI startup founded in March 2024 that simulates user research with synthetic AI agents (replacing surveys and focus groups for clients like Accenture, EY, and political campaigns), followed a similar path.
In early December 2025, TechCrunch reported a Series A round led by Redpoint Ventures that achieved a $1 billion “headline” valuation — with the round size above $50 million.
Again, WSJ sources revealed the split: roughly half the investors bought in at $1 billion, while the other half invested at around $450 million. The blended valuation ended up well below unicorn level, but the public announcement screamed unicorn.
Carta Data: ~20 Deals in the Last 6–12 Months, Accelerating in Q4 2025
According to private-market data platform Carta, there have been roughly 20 such multi-valuation deals in the past 6–12 months, with the frequency spiking sharply in the final quarter of 2025.
The tactic is gaining traction precisely because the AI market has cooled from its 2023–2024 frenzy. Back then, founders held the power — VCs raced to deploy capital into anything with “AI” in the pitch. Now, with more caution in the air, founders need creative structures to keep momentum and attract top talent.
Is It Legal? Mostly Yes — But It Raises Questions
Lawyers consulted by WSJ say the practice is generally permissible under U.S. securities law, as long as disclosures are handled properly and no fraud occurs. Different classes of shares or side letters can legally create varied pricing in the same round.
The bigger issue is optics and fairness: how many investors will happily join when they know the lead got a 2–3× better deal just days earlier? And what happens if the company doesn’t live up to the headline number?
Silver Lining: It Helps Employees (a Lot)
One undeniable upside: rapid valuation jumps boost the paper value of employee stock options. In a talent war for AI engineers and researchers, the ability to say “we’re a unicorn” and show quickly appreciating equity makes hiring much easier.
Founders argue it’s a win-win: lead investors get rewarded for taking early risk, the company gets better recruiting power, and follow-on capital flows in at a premium that reflects perceived momentum.
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Normal Evolution of Deal Structuring — or Shady Valuation Gaming?
The tactic is dividing the ecosystem. Some see it as smart financial engineering in a tougher market. Others call it artificial price inflation that distorts true price discovery and risks creating misaligned incentives.
Whatever side you’re on, one thing is clear: in the current AI fundraising environment, the path to a billion-dollar headline is getting more creative — and more stratified — than ever before.
