Achievements
- Part of Y Combinator W22 with Serif Health
- Built and scaled tech teams at Dropbox, Microsoft, Truepic
- Contributed to Sold., acquired by Dropbox
- Held engineering leadership roles at Dropbox and One Medical, both unicorns
- Co-founded Serif Health, focused on healthcare price transparency APIs
- Serif Health participated in Y Combinator Winter 2022 batch
Ever heard of Matthew Robben
Major props to Matthew Robben, this guy’s a straight-up tech hustle legend. He’s part of YC W22, but his story’s way deeper than just that. Started his career diving into the startup world as an early engineer and engineering manager at some heavy hitters like Dropbox, Microsoft, and Truepic. Dude’s been in the trenches, building stuff from the ground up, which explains why he’s so damn sharp at understanding what really moves the needle.
He’s not just grinding at big companies though. He was at Truepic and Microsoft, but what really stands out is his stint at Dropbox and One Medical, both of which crushed it and went public as unicorns. That’s no small feat. Plus, he helped build Sold., which was later acquired by Dropbox. The guy’s got a nose for what’s useful and knows how to scale tech and teams.
Then, in 2020, he jumps into the founder game for real. Co-founds Serif Health with Rafiq Ahmed, and bam, YC W22. Serif is all about healthcare price transparency APIs and data, which is some advanced shit. It’s about making healthcare costs clear and accessible, which honestly is a huge deal considering how fucked up the system is. Starting Serif wasn’t just a hobby, it’s like his mission to shake up healthcare with tech. And you can tell he’s all about building things that actually matter, not just chasing quick wins.
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Talk to herWhat does all this say about him? It’s clear Matthew’s super driven by having an effect. He’s not just riding the wave of tech trends, he’s jumped into problems he cares about, like healthcare, and pushed through the bullshit to create real solutions. His process shows he’s passionate, relentless, and knows how to build stuff that lasts. He’s the kind of guy who’s been through the grind at big startups, learned the ropes, and now he’s using that knowledge to do something big on his own.
Bottom line? Matthew Robben is that rare mix of hardcore engineer and visionary founder. He’s been in the trenches, crushed it at big companies, and now he’s out here trying to change healthcare for the better. No Cap, this guy’s the real deal.

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