The 100 Year Conversation continues with Vlad Tenev. Vlad was born in Bulgaria and moved to the United States as a child. When he was ten or eleven, he was figuring out investing on dial-up with a pretend portfolio on Yahoo Finance. At twelve, he made a deal with his father. If he scored above 1300 on the SAT, he’d get his score in dollars to invest. He scored 1370. You can see the beginnings of Robinhood in that story. Owning stocks felt like collecting to Vlad. He read the shareholder materials he got in the mail and was proud to be an owner. Years later, he helped millions of other people become owners too. Vlad has a fondness for difficult things. He talks about Robinhood’s toughest moments with a warmth I didn’t expect. “Those are memories I cherish,” he told me. “My only regret was that I didn’t enjoy it more at the time.” @vladtenev

Nikesh Arora is the Chairman and CEO of Palo Alto Networks. Before that, he ran Google’s European business and was handpicked by Masayoshi Son to one day lead SoftBank. He came to America with $2,000 from his father, planning to go home once he had saved $100,000. In 2018, Nikesh took over Palo Alto Networks despite knowing almost nothing about cybersecurity. Since then, its revenue had quadrupled and its stock has risen ~10x. Nikesh is the operator’s operator. He walks into industries as an outsider, sees the game more clearly than the people inside it, and makes very big companies move very fast. Eric Schmidt once called him “the finest analytical businessman” he had ever worked with. Nikesh says he has had “limited success” and “just runs a normal business.” My conversation with @nikesharora:

A small update to the 100 Year Conversation we’re excited about: We’ve added tooltip companions to our interviews: archival findings, rare images, napkin sketches, and other context for the curious reader. The idea is simple: make each conversation more enjoyable and informative, without forcing you to leave the page and disappear into a maze of tabs. Live on all conversations. Let us know what you think!