
The Lanai Purchase
Paperback

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5,564 words · no email, no account
No. 109 · Technology & Money · Technology
a biography of Jack Patrick Dorsey
Two companies, two firings, and one message of four words: "just setting up my twttr," sent from a San Francisco office at 9:50 p.m. Pacific Time on March 21, 2006.
Jack Patrick Dorsey, born in St. Louis, Missouri, on November 19, 1976, co-founded Twitter with Biz Stone, Evan Williams and Noah Glass. He was fired as chief executive in October 2008, returned in 2015, and was fired again in November 2021. In between he founded Square, now Block, with Jim McKelvey in 2009 and carried the public-company chief executive's job twice over. Since 2021 his work has gone into the open-protocol social network Nostr and into Block, the Bitcoin-Lightning payments company.
Sterling Aldridge's biography follows the whole arc: the St. Louis childhood as eldest of three sons of a mass-spectrometer machinist and a homemaker, the early obsession with dispatch software, the New York University dropout, the web cab-dispatch work in Oakland, and the Odeo podcasting startup that produced Twitter as a side project. Then the 2007 SXSW launch and the long ascent through the social-media decade, the November 2013 IPO, the years of Elliott Management's activist pressure and its 2020 challenge to his job, the Square founding and the double duty, the 2021 exit from the Twitter chief executive's chair, the Elon Musk acquisition of October 2022 that Dorsey publicly approved, the Twitter Files release that December, the Bluesky board departure of May 2024, and the Nostr and Lightning infrastructure investments that have defined the years since.
What emerges is a portrait of a founder whose two-decade career has held the seat at the center of two of the most consequential developments in twenty-first-century communications and payments — and whose investments since Twitter suggest he is working on a third.
The opening chapter is published in full — read it here.
Jack Patrick Dorsey. The title never carries the subject's name: it names one concrete thing out of the life — in this case The Two Companies — and the name goes on the line underneath.
No. No subject, estate, label or foundation had approval over the text, and none paid for a word of it. The cost of that independence is that no new interviews were conducted for the book; it is built from the public record, and it says on the page where a scene is reconstructed rather than documented.
Yes — the whole opening chapter and the writer's foreword, free and in full, with no email address and no account. That is 5,564 words of the book.
About 63,000 words, 19 chapters, 206 pages in the paperback.