Webinar
Masterclass: Inside the Deal—Why We Said Yes to Circle
Join Alumni Ventures Managing Partner Chris Sklarin for an exclusive masterclass exploring how our team sourced, evaluated, and ultimately invested in Circle—a rising star in the fintech and digital currency infrastructure space that recently completed a successful IPO.
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Circle, the company behind the USDC stablecoin, is backed by top-tier investors including BlackRock, Fidelity, and Goldman Sachs. As a pioneer in regulated digital payments, Circle is shaping the future of global finance and enabling secure, scalable crypto transactions across the internet economy.
In this behind-the-scenes session, Chris will break down the sourcing process, outline key diligence criteria, and explain how Circle stood out among a crowded fintech landscape. Attendees will get an inside look at how venture capitalists evaluate disruptive opportunities and build conviction around transformational companies.
Whether you’re already investing in crypto or just exploring the fintech frontier, this webinar offers real-world insights into backing bold innovation. Don’t miss this deep dive into one of the most consequential bets in financial infrastructure.
Why Attend?
- HomeDeal Breakdown: Get an inside look at the full sourcing and diligence process behind our investment in Circle.
- HomeVC Best Practices: Learn how top venture firms evaluate innovation in highly regulated, fast-moving markets.
- HomeReal-World Insights: Hear directly from Managing Partner Chris Sklarin about what it takes to back a fintech disruptor.
Alumni Ventures is America’s largest venture capital firm for individual investors.
About your presenter
Overview
Chris Sklarin is Managing Partner of the Castor Fund at Alumni Ventures, where for over seven years he has led investments in transformative technology companies redefining how we compute, communicate, and cure. He has deployed more than $120 million across all stages—from seed to growth—building Castor Ventures and expanding the portfolio to over 150 companies. The Castor portfolio features industry leaders such as Algorand, Boldin, Capital RX, Enable, Groq, Ocient, Qedma, RapidSOS, Synchron, and Unlearn AI, each tackling high-impact problems with ambitious solutions.
With over 20 years in venture capital and more than a decade in product development and sales engineering, Chris has also held venture roles focused on enterprise and mobile investments, served as Director of Business Development at a biomedical venture accelerator and an early-stage firm, and sourced seed-stage deals at JumpStart, a nationally recognized venture development organization in Cleveland. Chris holds an SB in Electrical Engineering from MIT and an MBA from the Haas School of Business at UC Berkeley.
Funds actively worked on
- Castor Ventures
- Syndications
Investment Areas of Focus:
Chris targets companies at the forefront of software, AI, data infrastructure, and connectivity, backing teams that are not just innovating but reengineering the physical and digital infrastructure powering the modern world. He believes the next generation of breakthrough companies will emerge from foundational shifts in technology and is committed to supporting the leaders driving that transformation.
A core component of Chris’s strategy is leveraging the powerful innovation engine of the MIT ecosystem. As an MIT alumnus, he taps this network to source compelling investment opportunities and connect with top-tier investors. Chris’s investment approach is informed by his early career as a software and sales engineer, with technical expertise in databases, telecom systems, and software architecture. This hands-on background sharpens his diligence and ability to assess technical complexity and market viability.