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...
8 days ago • 3 min read
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...
15 days ago • 3 min read
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...
22 days ago • 3 min read
People and money Many long-standing business systems are shifting out from under us right now. Content marketing started changing as soon as ChatGPT launched, not entirely for the better. Software development is changing for sure, at least if you're technical-ish; coding isn't even the right verb anymore. Companies are optimizing supply chains, using AI to interact with customers, and, at least in theory, changing how decisions get made. It's a lot of change. But whatever industry you're in,...
29 days ago • 3 min read
"But I'm not technical!" A few months back, I met with a mid-career person who pitched me on a new role: they wanted to spend time with AI product builders to figure out how the industry is changing. My immediate response was: Ok, but what is your experience building AI products? "But I'm not technical!" they protested. Well, I told them, that won't cut it for building an informed perspective on AI transformation. The state of play is changing too quickly. The best way to build an informed...
about 1 month ago • 3 min read
Tin can in the sky A few years ago, I was flying across the country for a business trip and counting on the flight to get some work done. Unfortunately, the wifi was out for the entire trip. When I landed, I complained about it to a coworker. "Yeah, that's annoying," he said. "On the other hand, you just spent a few hours inside a tin can in the sky, and now you're 3,000 miles away from where you had breakfast this morning. Technology is amazing!" Take two things from this story. One, it is...
about 1 month ago • 3 min read
The prompt industrial complex These days, AI can produce most common workplace artifacts. From emails to slide decks to financial models to working code, a workable first draft is often just one prompt away. Ok, maybe not one prompt away. It usually takes a few tries to describe exactly what you want. If you care about quality, getting a credible artifact typically involves several prompt <> production cycles. AI refines its output based on how you evolve your prompt, and you refine your...
about 2 months ago • 3 min read
Prognostication vs. reality I spent 2025 as Founder in Residence at Operator Collective, a venture firm whose LPs include many of the most successful tech leaders of the last decade. During that year, I spent time not only with hundreds of AI startups but also with these operators. For me, these discussions informed several predictions about AI that are now coming true, So I was extra interested in the data set that Operator Collective dropped last week. They surveyed the operators in tech...
about 2 months ago • 3 min read
I pretend to be a night owl so I can have interesting conversations I am a morning person. No matter what time I go to bed at night, I wake up before 6am. I don't plan it. It just is the way my body wants to work. It turns out that being a morning person is a lucky life hack: in theory, morning people are likely to be happier and healthier. I don't know how the science on that will bear out over time, but there's no doubt that it's an advantage to have your best energy just as your work or...
2 months ago • 3 min read