Castelion, founded by ex-SpaceX executives in 2022, just raised a $1B Series C at a $13B valuation, led by a16z, Carlyle, and J.P. Morgan. The startup has already secured $500M in U.S. military contracts by betting it can make hypersonic weapons faster and cheaper than the Pentagon's traditional primes. The cash goes toward its Blackbeard missiles and a new Mexico production facility, as the U.S. races to close a stockpile gap with China.
NeXT was bleeding cash and its university sales flopped, until the CIA's classified "Program B" showed up in 1986 with custom orders fit for spy-satellite image analysis. The classified revenue helped keep Jobs' company afloat long enough for Apple to buy it back. That's why the code that would become the foundations of macOS and iOS was born, partly on the intelligence community's dime.
Sasha Orloff has raised more than $1 billion across his companies, and his hardest-won lesson is that fundraising is won in the financials, not the pitch. VCs don't expect perfection, they expect founders who know their runway, margins, and revenue quality cold. He admits he once nearly lost a term sheet because his data room wasn't ready, and says waiting until you're almost out of cash destroys leverage. That frustration is exactly what led him to build Puzzle.