Eric Wroolie

About

I grew up in San Diego. Not the nice part — the part where you learn early that nobody’s coming to save you. Montgomery High School. I was the kid who got picked last for teams in PE. On a good day, second to last. That sticks with you. Decades later, thousands of miles away, it still sticks with you.

When I was eighteen I joined the United States Army, which is exactly the kind of decision you make when you don’t know what else to do with yourself. Here’s the part that surprises people: they made me a Chinese Mandarin linguist. I spent months at the Defence Language Institute in Monterey, California, learning to read, write, and speak Mandarin Chinese. Then they taught me Vietnamese too. A kid from San Diego who couldn’t get picked for dodgeball was now working in military intelligence. Life is strange.

I did well in the Army. I got promoted, went through PLDC, and for the first time in my life I felt like I was good at something. The Army taught me that confidence isn’t something you’re born with — it’s something you build, one terrifying experience at a time. I still think about that.

After the Army, I took a hard left. I became a narrator at Sea World of Texas. Yes, really. The guy who used to sit alone in the barracks reading language flashcards was now standing in front of crowds, talking about dolphins. It was a stepping stone I didn’t know I needed — learning to hold a room, learning that my voice could actually be worth something.

I taught school for a while after that. Then, in a move that made sense to absolutely nobody, I packed up and moved to England. I’d met someone. Love will make you do unreasonable things, like trade Southern California sunshine for Birmingham rain.

In the UK, I fell into investment banking. BNP Paribas first, then Deutsche Bank, then Barclays Capital. I did a stint at BBC Worldwide too. I was a contractor — decent money, interesting work, but I was building someone else’s thing. Every morning on the train to London I’d think: there has to be more than this.

So in 2004, I started Overpass. A mobile development company. Just me, a laptop, and the probably-delusional belief that I could make a living building apps. I wrote my first blog post that August. I had no clients, no reputation, and no plan. I had momentum, and momentum beats standing still every time.

Twenty-plus years later, Overpass has built apps that have been downloaded tens of millions of times. I started a YouTube channel called A Minute of Overpass and somehow made over a thousand videos about app development, business, and whatever else was rattling around in my head. I’m not sure anyone expected that. I definitely didn’t.

In 2023, at the age of fifty, I started doing stand-up comedy. I’d never performed comedy before. I had no material, no stage presence, and absolutely no business being up there. My first gig was terrifying. My second gig was also terrifying. Someone asked me beforehand, “Are you one of the comics?” and I said yes, even though every cell in my body was screaming that I was a fraud. I did the gig anyway. And it was awesome. What a rush.

In 2025, I made a decision that changed everything about how I work. I let go of my last human developer and started building exclusively with AI. No more offshore teams, no more miscommunication, no more managing people across time zones. Just me and the machines. It’s lonely sometimes — AI doesn’t push back, it doesn’t argue, it doesn’t surprise you with a better idea over lunch. But it works. And I’m still learning what that means.

I’m 53 now. I’m still a work in progress. I don’t have it figured out. I’m an introvert who forces himself to be an extrovert. I’m a solo founder who misses collaboration. I’m an American who says “colour” and “realise” but still thinks in dollars. I’m a father of three who sometimes wonders if his kids know how much of this was for them.

If my life is a day at Disneyland, I want to leave saying I’ve been on all the rides.

I’m not done.

Find me elsewhere