Achievements
- Founded Gerald Technologies in 2018 to revolutionize personal finance
- Secured a spot in Y Combinator Winter 2021 batch (Y Combinator W21)
- Built fintech platform that rewards consumers for smart financial decisions
- Founded Quick.me, a B2B finance and insurance platform
- Founded Conduet-Med, a HIPAA-compliant healthcare tech company
- Former Vice President at Neuberger Berman
The deal with Ola Okeshola
Straight up, let me put you on to Ola Okeshola, this guy’s a straight-up boss in the fintech game. So, Ola’s the founder and CEO of Gerald Technologies, which he kicked off back in 2018. The dude’s all about changing how people handle their money, making it easier and more rewarding to make smart financial moves. Think of it like, he wants you to get paid for being financially smart, whether that’s paying bills on time or avoiding overdraft fees. No bullshit, he’s really about empowering folks, especially with tech that’s actually useful.
Now, the wild part? Ola’s no random startup guy. He’s got a solid background in finance and entrepreneurship, with over 7.5 years riding the industry wave. Before Gerald, he jumped into a bunch of different stuff, founded Quick.me, which was all about B2B finance and insurance, and also Conduet-Med, a healthcare tech platform that’s HIPAA-compliant. Basically, he’s been in the trenches, building stuff that actually matters. Plus, he was a Vice President at Neuberger Berman, so he’s not just talk, he’s been deep in the financial world, grinding at a high level.
And get this, Ola’s based in Brooklyn, NY, but his process started way before that. He went to Yale School of Management, so he’s got that solid business education backing him up. But what really jumps out is his drive. He jumped into Gerald after all that experience because he saw a real problem, people getting screwed over with fees and bad financial decisions, and he wanted to fix that. That’s the kind of motivation that separates the real deal from the bullshitters. He’s not just in it to make a quick buck; he genuinely wants to make a difference.
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Talk to herOh, and he’s part of YC’s Winter 2021 batch, so he crushed it enough to get into Y Combinator, which is basically startup heaven. That’s a big badge of honor, showing he’s got what it takes to scale and innovate on a serious level.
Bottom line? Ola Okeshola is a dude who’s been around the block, seen how the money game works, and decided to flip it on its head. He’s serious about using tech to enable regular folks and make finance fairer. That’s why he’s important, not just as a founder, but as someone genuinely trying to shake up the system and make it better for everyone.

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