He nearly lost a term sheet because his own accounting was a mess.
So he built the fix, and sold it to every founder who's ever made the same mistake.
The company is Puzzle, founded by Sasha Orloff, a repeat founder who grew up in the Bay Area, studied in Europe, worked at the World Bank while getting his MBA, then joined Citigroup's venture capital team. On a whim, on the way to the airport, he applied to Y Combinator. He got in.
That idea became Mission Lane and LendUp, two fintech companies he built and ran at the same time. Together they raised more than $1 billion
But Orloff has talked openly about nearly losing a critical term sheet because his own data room and books weren't ready when investors came looking.
He built Puzzle to fix that specific failure for the next founder. AI-native accounting software, meant to replace the version of QuickBooks most startups outgrow within a year.
The pitch: books that update continuously instead of arriving three weeks late. AI agents draft the categorization, the reconciliation, the month-end close, but nothing posts to the ledger without a human signing off. "95% accurate books," Orloff has said, "are 100% useless."
They launched publicly in July 2023. Growth was double-digit, month over month, immediately.
In November 2023, they raised a $30 million round, backed by investors including S32, bringing total funding to $50 million. By their most recent disclosed round, total funding reached $66.5 million.
Over 7,000 startups, small businesses, and accounting firms ended up running their books on it.
Then, on September 2, 2026, Accrual, an accounting-intelligence platform that had only existed since February, announced it was acquiring Puzzle's entire accounting-firm business: the ledger, the AI Close product, the technology behind it, and Orloff himself, along with his team.
Accrual had been running its own internal books on Puzzle since early in its own existence. The buyer was already a customer.
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