Sequoia Capital Part II (with Doug Leone)

The episode opens by dedicating itself to Don Valentine, then picks up Sequoia's history in 1996, when Valentine handed the firm to Michael Moritz and Doug Leone. Leone's own account of how he arrived is a story about acculturation rather than credentials: the family left Italy when he was eleven and reached New York on August 1, 1968, on the Michelangelo, after roughly two years in which he and his mother did not see his father, who had gone ahead and worked as a service engineer for a marine equipment company at a peak income Leone recalls as $25,000.

The detail that carries the rest of the interview is the contrast he draws between an over-loved only child in Italy — aunts and uncles with no children of their own, "lots of trust, lots of love" — and a New York high school where, in his words, you got "the hell beaten out of you, crap beaten out of you, emotionally, physically". He presents that as the source of his two modes, the very warm side and the side that "just don't give an inch", rather than as a grievance.

The academic record he volunteers is not the one in the bio. He says he was thrown out of Cornell after his first year, with semester grades of 134 and 122, having skipped so many classes that he never met half his professors. His explanation is relief rather than rebellion: once he could speak English he became "one of the very accepted kids" and lost his head. He insists the episode cost him learning but restored him to normality, which is a stranger claim than the standard redemption arc and is the version he chooses to tell.

His account of personal change is unusually specific for this genre. Tested early as process-driven — a mind he describes as a tree structure — he says the 2012 transition, with Moritz stepping back, forced him to rely on intuition, and he reports the tester's reaction that only he and Michael Dell had made that shift. He also places himself exactly halfway between introvert and extrovert and dates the charm to roughly the last five years.

His route into technology sales runs through an accident. At Hewlett-Packard in 1979 two senior salesmen split Manhattan into thirds and he, knowing nothing, trusted them and took the worst share — north of 96th Street, in a city where he says it was not safe to walk north of 79th. That territory happened to contain Columbia, and a dean of engineering who explained ARPANET and open systems to him; he then went to Prime for a year and a half specifically to sell on Wall Street because "that's where the money was".