







The ask was to reward safe drivers. What that actually required was designing for two people with completely different definitions of winning.
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Over five years we grew to a team of six, generated $1.5M in total revenue, and worked with clients from early-stage startups to Meta and Indeed. We expanded internationally. And then we closed.
This isn't a project case study, it's what I learned about leadership when the stakes were my own.
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Stylists needed a way to express who they were. Salon owners needed to evaluate something nearly impossible to quantify: fit. Building for both at once was the real design problem.
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(Acquired by Cedar in 2021)
Patients were billed by people they'd never spoken to, for amounts no one could explain, through a process built around insurers and providers, not them. OODAPay flipped that.
Read the storyMy curiosity about tech goes back to willing a Napster download to survive overnight. What I loved wasn't just the technology, it was that someone had built something millions of people were actually using. I ended up in product design chasing that same thing.
These days most of that points at AI and what it means for how design teams think and make decisions together. When I'm not doing that: co-hosting a podcast, riding motorcycles, spinning vinyl, and losing arguments with two senior dogs.
I build with AI the way I've always approached new technology — test it before putting it to work. In practice that takes form in using tools like Claude or v0 to pressure-test ideas early, before they become assumptions harden into the wrong thing to build.