Thomas Dowling

Yo, so you gotta hear about Thomas Dowling. This guy’s a straight-up legend in the startup and public service worlds. He jumped into YC’s S19 batch, yeah, the same one as some of the hottest startups lately, and since then, he’s been on a crazy ride.

Started out with some solid creds, he’s a Rhodes Scholar from Oxford, which is no joke, and he also has a BA from Illinois. But what really sets him apart is how he’s been crushing it in both tech and government. Like, he’s the guy who’s not just talking about change, he’s building it.

He co-founded TaxProper, a SaaS biz for managing property taxes, think big real estate players, managing hundreds of thousands of properties worth billions. He took this thing from zero to managing over 115,000 properties valued at more than $35 billion. That’s a monster portfolio. And he did it while raising over $2 million from heavy hitters like Khosla Ventures and YC itself. Basically, he proved you can build a legit startup that actually moves the needle.

Then, in 2022, Opendoor saw what he was doing and scooped him up as Director of TaxProper. He’s now plugged into one of the biggest players in real estate tech, shaping how they handle taxes at scale. This guy’s not just building startups, he’s shaping the future of real estate and property management tech.

But it’s not just startups. Thomas is also deep in public service. He was appointed by Illinois Governor JB Pritzker to the Illinois Student Assistance Commission. That’s a big deal, he helped increase student aid, making college more accessible. Plus, he was an advisor to Chicago Mayor Lori Lightfoot, focusing on municipal finance, pensions, and gaming issues. Basically, he’s been influencing city and state policies, bridging the gap between tech innovation and real-world impact.

What’s the story here? I think it’s pretty clear. Thomas is all about building solutions that matter, whether that’s in real estate, education, or city management. He’s driven by a desire to fix bullshit systems, make things more fast, and actually help people. His process shows that real impact comes from jumping into the deep end, taking risks, and using your skills to shake shit up.

So yeah, this dude’s a perfect blend of tech genius and public servant, the kind of guy who’s not afraid to get his hands dirty, whether that’s raising millions, advising city leaders, or launching startups. No Cap, he’s a mover and shaker who proves you don’t need to pick one path. You can do both, and crush it.