About Charles Cascarilla
Charles Cascarilla is the CEO of Liberty City Ventures, a New York City-based investment firm focused on technology companies across fintech, blockchain, enterprise software, and consumer internet. He is also widely recognized as a co-founder of Paxos, a regulated blockchain infrastructure company that has become a cornerstone of institutional crypto adoption, powering stablecoin and settlement solutions for major financial institutions worldwide.
Cascarilla's dual identity as both a venture investor and a fintech company builder gives him a rare perspective in the investment world. Through Liberty City Ventures, he deploys capital into high-growth technology companies, while his experience building Paxos from the ground up provides him with deep operational understanding of what it takes to scale a technology company in a heavily regulated environment. This combination of investor and operator expertise is at the core of his investment approach.
Among Liberty City Ventures' most notable recent investments is the co-lead of Cloaked's $375 million funding round. Cloaked, a privacy and identity management platform, represents the kind of company that Cascarilla finds compelling: a technology-forward business addressing a growing consumer need with strong regulatory tailwinds. His ability to identify and support companies at the intersection of technology, privacy, and financial infrastructure has made Liberty City Ventures a respected name in NYC's vibrant tech investment scene.
Net Worth
Charles Cascarilla's net worth is derived from multiple sources: his equity stake in Paxos, his ownership and carried interest in Liberty City Ventures, and his personal investment portfolio spanning fintech, blockchain, and enterprise technology companies.
Charles Cascarilla's net worth is not publicly disclosed but is estimated to be substantial given his co-founding stake in Paxos, which has raised significant venture funding and powers stablecoin infrastructure for major financial institutions, and his ownership of Liberty City Ventures.
Cascarilla's earnings come from multiple streams: his role at Liberty City Ventures (management fees and carried interest), his position as co-founder of Paxos, and returns from his personal investment portfolio across the technology sector.
Investment Strategy
Charles Cascarilla's investment strategy at Liberty City Ventures reflects his deep roots in fintech and blockchain combined with a broader technology thesis. He invests in companies building foundational infrastructure and platforms across fintech, blockchain, enterprise software, privacy technology, and consumer internet. His approach is informed by his experience as a company builder — he understands the challenges of scaling technology businesses in regulated environments and actively seeks founders navigating similar paths.
Cascarilla places particular emphasis on companies operating at the intersection of technology and regulation. His experience co-founding Paxos, which required navigating complex regulatory frameworks to build trusted financial infrastructure, gives him a keen eye for opportunities where regulatory clarity creates competitive advantages. He looks for businesses with strong technical foundations, clear regulatory strategies, and the ability to earn trust from institutional customers and consumers alike.
The co-lead of Cloaked's $375 million round illustrates Cascarilla's thesis in action. As privacy regulation expands globally and consumer demand for data protection grows, Cloaked sits at the intersection of technology and regulatory tailwinds — precisely the kind of positioning that Liberty City Ventures targets. Cascarilla's portfolio construction balances high-growth consumer plays with infrastructure-level investments, reflecting a conviction that the most durable technology companies often operate at the platform layer.
Notable Quotes
“The most important technology companies are the ones you don't see — the infrastructure layer that makes everything else possible. That's what we built with Paxos and what we invest in at Liberty City.”
— Fintech Conference Keynote
“Regulation isn't an obstacle — it's a moat. Companies that figure out how to build trusted, compliant infrastructure will be the lasting winners in fintech and beyond.”
— Interview, 2025
“Privacy is the next great technology platform. As consumers demand control over their digital identities, the companies enabling that control will create enormous value.”
— NYC Tech Summit
Contact Information
For inquiries related to Liberty City Ventures or Charles Cascarilla, please visit the official Liberty City Ventures website. For inquiries related to Paxos, visit paxos.com.
Charles Cascarilla is active on LinkedIn and Twitter, where he shares perspectives on fintech, blockchain, privacy technology, and the venture landscape.
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Contact via LessieFrequently Asked Questions
Who is Charles Cascarilla?
What is Liberty City Ventures?
Liberty City Ventures is a New York City-based investment firm led by Charles Cascarilla. The firm invests in technology companies across fintech, blockchain, enterprise software, privacy technology, and consumer internet.
What is Paxos?
Paxos is a regulated blockchain infrastructure company co-founded by Charles Cascarilla. It provides stablecoin and settlement solutions for major financial institutions worldwide and has become a cornerstone of institutional crypto adoption.
What is the Cloaked investment?
Liberty City Ventures, under Cascarilla's leadership, co-led Cloaked's $375 million funding round. Cloaked is a privacy and identity management platform that sits at the intersection of growing consumer privacy demand and expanding global privacy regulation.
What is Charles Cascarilla's investment strategy?
Cascarilla invests in companies at the intersection of technology and regulation, particularly in fintech, blockchain, enterprise software, and privacy technology. His approach is informed by his experience building Paxos in a heavily regulated environment.
What is Charles Cascarilla's net worth?
Charles Cascarilla's net worth is not publicly disclosed but is considered substantial, derived from his co-founding stake in Paxos, ownership and carried interest in Liberty City Ventures, and a personal investment portfolio across the technology sector.
How can I contact Charles Cascarilla or Liberty City Ventures?
Charles Cascarilla can be reached through Liberty City Ventures' official website at libertycityventures.com or through his LinkedIn and Twitter profiles. For Paxos-related inquiries, visit paxos.com.
What is Charles Cascarilla's educational background?
Charles Cascarilla holds a BA from Duke University and an MBA from Columbia Business School. His business education, combined with hands-on experience building Paxos, informs his approach to technology investing at Liberty City Ventures.