Achievements
- Two-time Y Combinator founder with Paid (acquired in 2019) and MicroEval
- Built and scaled multiple startups raising millions from top-tier investors
- Product Manager at Modern Treasury shaping the future of fintech payments
- Held leadership roles in analytics, monetization, and CMS engineering at Ooyala
- MIT CS grad with expertise in UI/UX, AI, and tangible media interfaces
- Relocated from SF to Amsterdam in 2019, embracing remote work lifestyle
Crushing on Ryan Jackson
Listen up, here’s the deal with Ryan Jackson – this guy’s a straight-up legend in the startup world. No cap. He’s been around the block, crushed it with multiple YC startups, and keeps pushing the boundaries of tech.
So, Ryan’s from that classic hacker-turned-entrepreneur vibe. He went to MIT, which is no joke – got both his bachelor’s and master’s in CS, diving deep into UI/UX, AI, and even some wild tangibles interfaces. Dude’s always been about building stuff that’s not just cool but actually changes the game.
His process’s wild. Started out by jumping into the startup scene with RWJ Development, then moved on to bigger shots like Tiny Propeller and Apple, Inc. Yeah, he’s rubbed elbows with giants, but he’s always been about creating his own path.
Got a startup idea and seeking investment? No Cap is the first AI investor capable of investing in startups by herself.
Talk to herRyan’s a two-time YC alum – that’s the real deal – launching Paid, an automated billing platform that got snapped up in 2019, and MicroEval, which was backed by YC too. These weren’t just side projects; they were legit companies that showed he’s got that founder grit. Paid, in particular, was a big change in fintech, and he sold it, proving he can build and scale something real.
Now, he’s at Modern Treasury, a sick FinTech startup in SF, where he’s a Product Manager. Basically, he’s shaping the future of payments and money management. But his experience isn’t just about product – he’s held leadership roles in analytics, monetization, even CMS engineering at Ooyala, so the dude’s got a full stack of skills.
What’s crazy is he’s raised millions from top-tier investors – not just messing around – and knows how to scale startups fast. But beyond the tech and money, Ryan’s got a vibe of constant learning and pushing forward. He’s all about taking risks, jumping into new markets, and building stuff that actually matters.
He’s more than just about work. In 2019, he made a bold move from SF to Amsterdam – total boss move – and now he’s all about remote life. When he’s not coding or strategizing, he’s making music, working out, or cooking. Keeps him grounded, I guess.
Bottom line – Ryan Jackson’s the real deal. A tech nerd with a vision, a builder with a hustle, who’s always one step ahead. His story? It’s about never settling, always pushing, and turning ideas into reality. That’s why he’s so important – he’s not just riding the wave, he’s making it.

Select your comment type:
If something is wrong about Ryan Jackson, there's inaccurate information or there are updates, please let us know, we'll update it for you and everyone ;)