A Father’s Hustle, a Shrimp Tank Seat, and a Bet on Connection
There’s something different about Jason R. Hill. You hear it in his voice. You see it in the way he describes what most people miss: that in a noisy world, real connection is a rare currency.
He didn’t start out with an app. He started with a father who sold nautical treasures at a cluttered New York storefront called Captain Hooks. From a young age, Jason learned how to make an experience, not just a sale.
Years later, he’d become a successful financial advisor. Then a podcast host on The Shrimp Tank. Then the guy everyone called for a referral. Eventually, the dots connected. What if there were a faster way for people to help each other? What if someone could pick up their phone, tap a button, and actually talk?
That question became Owwll, a platform for one-on-one advice calls between professionals. But as Jason explains to host Keith Costello, building a tech startup wasn’t just a professional leap. It was personal.
“I mortgaged my house, sold my properties, drained my retirement. I went all in,” Jason says, his voice cracking with emotion. “Because I believe in this. I believe people still want to talk to each other.”
His honesty cuts through. He talks about the stress, the judgment, the quiet fears, and why he still shows up every day. Not because it’s easy. Because it matters.
From startup realities to the IKEA effect, from South Florida roots to national ambition, Jason R. Hill’s story is a masterclass in persistence. But more than that, it’s a story about what it means to really care.
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