Kevin Hollingsworth

Backstory

I began my career nearly 30 years ago at Lehman Brothers, where early exposure to Y2K and innovations like Cantor Fitzgerald’s eSpeed sparked my interest in the intersection of finance and technology. I spent the next 14 years at Advent Software helping RIAs, asset managers, and hedge funds scale through automation of core back-office and trading systems—well before fintech was a common term.

I later worked at Salesforce driving digital transformation for large financial institutions, then at Envestnet | Yodlee, a pioneer of open banking and financial data connectivity. Most recently, as Head of Sales at Deserve, I helped modernize the credit industry with a mobile-first platform enabling fintechs and community institutions to compete with national banks.

I studied Economics and History at Villanova University and am a graduate of the Chicago Booth CRO Program.

Bitcoin Story

I was first exposed to Bitcoin at Money 20/20 in 2016, where a crypto exchange handed out satoshis to anyone who onboarded. Like many at the time, I didn’t follow through.  In late 2019, while running sales at Yodlee, I was researching companies with high volumes of new account openings—work that led me from online gambling platforms to crypto exchanges like eToro. That month, I opened an account and started buying Bitcoin. I went down the broader crypto rabbit hole—altcoins, Crypto Twitter, and glossy “earnings reports” that ultimately felt like noise. Bitcoin was the only thing that made sense. Still, distracted by everything else, I rode the market up and back down and exited in mid-2020.

Bitcoin re-entered my life in 2024 through Deserve, where I was Head of Sales. Many of our customers were fintechs, including Swan Bitcoin, and I got to know the Swan team well. In June 2025, Jeremy urged me to read Yan Pritzker’s Inventing Bitcoin and consider a role on Swan’s Private team. That book changed everything. I was struck by Bitcoin’s elegance, clarity, and design—and by how deeply it connected technology, economics, and the history of money. Three weeks later, I called Jeremy and said I was all in.

After 25 years in fintech and wealth technology, I realized I’d had a blind spot. I only wish I’d read Yan’s book sooner.