Jack Dorsey: Square, Cryptocurrency, and Artificial Intelligence

Lex Fridman introduces Jack Dorsey as co-founder and CEO of Twitter and founder and CEO of Square. Because of events around Twitter's leadership at the time and the very limited time available, the conversation is deliberately focused on Square and broader philosophical topics. A deeper discussion of engineering and AI at Twitter is left for a possible second appearance.

Fridman notes that the conversation was recorded before the outbreak of the pandemic, and sends encouragement to listeners bearing the medical, psychological and financial burden of the crisis.

He also points out that Dorsey moved $1 billion of Square equity, which he describes as 28% of Dorsey's wealth, into an organization funding COVID-19 relief. Fridman, citing Andrew Yang's tweet, calls it a spectacular commitment, and praises the fact that it operates transparently by posting all donations to a single Google doc.

The remainder of the opening is the usual show format and a sponsor read for Masterclass, which Fridman presents with the promise that ads come only at the start and never in the middle of the conversation. His advice for the service is not to be overwhelmed by choice: pick three courses and watch each all the way through. The conversation with Dorsey begins at this point.

Fridman observes that Dorsey has appeared on several podcasts, including those of Joe Rogan and Sam Harris, but that some topics were not covered: machine learning and artificial intelligence (narrow and general), engineering at scale, cryptocurrency, blockchain, universal basic income, and philosophical questions about life, death, meaning and beauty.

Dorsey is involved in building some of the biggest network systems in the world, with trillions of interactions a day. Fridman asks how a programmer who started in C reaches that scale. Dorsey describes himself with an exact phrase.

I'm a hacker, I'm not really an engineer.

His first answer is to hire people he can learn from. His hacker approach is to do whatever it takes to make a thing work, so that he can see and feel it and learn what has to come next. Very often what comes next is bringing it to more people, which is what he means by scale.

He credits the open source community for most of what he learned about hacking, programming and engineering. In his account open source is slow but deliberate, and its pace lets you watch every mistake, success and problem laid bare, and see what it takes to build something meaningful. He stresses the generosity of people who give up their time with no expectation of return beyond being part of something larger than themselves.

Fridman presses on whether the challenge at Square's scale is fundamentally software, hardware, or the social problem of building large engineering teams. He notes that a system that rarely goes down, is secure and handles all of these transactions is rarely praised for how remarkable it is.

Dorsey says there is no single answer: you have to focus on all of them, and that depends on how you face problems and whether you can break them into parts. In his view the biggest mistake is trying to address too many things at once, not going deep enough with questions, not being critical of answers, or not forming hypotheses that can actually be tested. These all fall under critical thinking and problem solving, the one skill he wants to improve every day. He also resists categories: over-committing to a hardware explanation misses software solutions, and the reverse is true as well, since hardware solutions can multiply a result tenfold. The underlying systems appear only to someone with creative thinking, critical questions and the patience to go deep.