Before venture debt became a familiar line on a startup’s balance sheet, Jim Labe was helping build the business of it. His career runs from equipment leases to public markets, with one question following him: how much time can borrowed money buy?

For more than two decades, Sajal Srivastava has worked at the junction of startup ambition and repayment schedules. As the TriplePoint Capital co-founder prepares to leave at the end of 2026, his career offers a close look at the machinery behind venture lending.