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Every week, I write a deep dive into some aspect of AI, startups, and teams. Tech exec data storyteller, former CEO @Textio.
The surreal life My Textio journey was filled with surreal experiences. For instance: The time we got our sales team internet by running cables outside of a downtown Seattle high rise 19 floors up The time we pitched a famous VC firm with 40+ men (and only men) packed into a 10-person conference room The time we hired a con artist who was defrauding a non-profit hospital in Alaska at the same time as he was defrauding us (no, really) But among the many surreal experiences I had, none was more...
The best compliment I ever got When I was in middle school, I had an academic rival. Occasionally we were friendly, but our classroom dynamic was open combat. One time, after a particularly contentious debate in algebra, I overheard his best friend complaining how argumentative I was. I'll never forget what I heard my rival say next: "Look, even her greatest enemy would admit she's good at math." All these years later, it remains one of the most validating compliments I've ever received. If...
The startup anti-pattern Back when I was young and naive, like in 2024, I assumed that everything I’d learned a founder would apply to the current moment. After all, we did so much good early AI at Textio. While most software was stuck on workflows, Textio promised outcomes! Our customer success engineers were essentially FDEs! We built generative writing features in 2019! But while we broke ground in many respects, in most ways, we were SaaS 101. I literally ran a bootcamp for Textios that...