Why I Left Fortune 500s and Unicorn Startups to Start WorkHoodie

My dad had a talk with me before I left for college. The kind fathers give when they want their kid to understand how the world works. Get serious, dress the part, show up like you mean it.

I listened. Then I said: “I’m going to go to work every day in a hoodie.”

It was a joke. But it stuck, not as a fashion thing, more as a promise I made to myself somewhere in that conversation. Work hard, build real things, but on your own terms. I didn’t really know what that meant yet. It took me about fifteen years and two pretty different kinds of burnout to figure it out.

Fortune 500

I joined Mastercard and I was good at it. I learned how systems hold up at real scale, how to make architecture decisions that have to outlive a sprint or a quarter, how to navigate a regulated environment where breaking things has consequences measured in billions of dollars. I led the Next Edge initiative, which was about reimagining how Mastercard processed card transactions for a cloud-native world. Real work with real stakes.

But I also felt something I kept trying to talk myself out of. The organization was slow. Not because anyone was lazy or incompetent, but because at that scale, with those stakes, slowness is a feature. Every decision gets reviewed. Every change has a process. Every process has an owner who has a manager who has a director who has a VP. I kept telling myself that was fine, that this was how serious companies operate, that I should feel lucky to be doing work at this level.

Then 2020 happened and the machine slowed down even more. And I stopped being able to talk myself out of it.

Unicorn Startup

I jumped to Dapper Labs and thought I’d found the answer. We were building things that genuinely had never been built before, NBA Top Shot, CryptoKitties, the infrastructure for a whole new category of digital ownership. I owned the wallet and payments platform, millions of users, over a billion dollars in transaction volume. We weren’t theorizing about scale, we were living it.

When Dapper spun out Flow Foundation I moved into something even broader, running the whole developer ecosystem across marketing, business development, product, and developer experience. I took the monthly active developer count from 250 to over 600 during a bear market while navigating a major network upgrade that broke nearly every smart contract on the chain. I was wearing every hat, having real impact, and had full autonomy to do things the way I thought they should be done.

And I still burned out. Different kind this time. No constraints, just fully consumed and exhausted. There’s always a higher number to hit, always a fire that feels more urgent than whatever personal thing you were about to do, always a reason to keep going that feels more important than the cost of going. I started asking myself whether that was just the price of doing meaningful work. Maybe this was what real impact felt like. I held that belief for longer than I should have.

Burnout

Mastercard broke me because I had too little room to move. Dapper and Flow broke me because I had no room to stop.

Once I was out of both of them long enough to actually think, I started seeing what I’d been looking for the whole time. I wanted the rigor I had at Mastercard without the bureaucracy. I wanted the autonomy I had at Dapper without the machine. Then with the trend of AI tooling and development a whole new world opened up. These two things shouldn’t be mutually exclusive, it should be possible to do serious, technically excellent work in a way that’s sustainable and directly impactful on real problems.

I found the writings of 37signals, met a lot of entrepreneurs at St. Louis Startup Week, and decided it was time to build something of my own.

WorkHoodie

The name came from that conversation with my dad. A joke that turned into a thesis.

You can be casual and competent. You can do technically rigorous work, bring genuine depth and experience, without the Fortune 500 bureaucracy or the VC grind. Working directly with people, staying small enough that quality stays high, and still showing up with the kind of capability that founders usually only get by hiring someone they can’t really afford yet.

That’s what WorkHoodie is. No agency, no handoffs, just me working directly with a small number of founders and teams at a time. I bring the architecture discipline and the execution speed because I’ve had to develop both. I embed in your team, review your PRs, make the hard calls on tech stack and hiring, translate between your engineers and your co-founder, and I’ll tell you when you’re building the wrong thing. The fractional model isn’t a compromise or a stepping stone to something bigger. It’s the point. Limited by design, deep over wide.

Why I’m Telling You This

WorkHoodie is new. I don’t have a long client list to show you.

What I have is a career that forced me to really understand both worlds, and a pretty clear sense of what the alternative could look like. Not another agency. Not a $300K hire most founders can’t justify yet. Just someone who’s been in the room when things break, knows how to fix it, and isn’t going to burn you out or burn themselves out doing it.

I built this because I needed it to exist. I’m betting other people do too.

Hoodies are for serious work.