Episode 379: Democratizing Venture Capital Through VentureStaking with Gerry Hays

From losing his $25,000 life savings on his first startup investment to democratizing venture capital for everyday investors, Gerry Hays shares proven strategies for making early-stage investing accessible through VentureStaking while teaching founders outside traditional tech hubs how to raise capital and build sustainable businesses. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Gerry Hays, founder and CEO of Doriot and Senior Lecturer at Indiana University's Kelley School of Business. Gerry has made 75+ startup investments, taught venture capital for 20 years, and built multiple companies from zero to exit, including HomeYeah.com and Charlie Biggs Food Company. His current mission focuses on expanding venture capital access beyond coastal hubs through innovative funding models. WHAT YOU'LL LEARN: In this episode, you'll discover how to participate in early-stage startup investing with as little as $10 through the VentureStaking model, why the right to invest later in winning companies proves more valuable than over-investing today, and how collapsing startup costs are fundamentally changing capital requirements for founders. Gerry shares strategies for avoiding what he calls "the fool's tax" when making your first investments, the critical importance of backing founders over ideas, and why venture investing resembles poker more than roulette. You'll also learn about building venture ecosystems within universities where students and alumni can collaborate on funding and growth, navigating the decision between raising capital versus bootstrapping your business, and the difference between venture-appropriate businesses versus lifestyle companies. The conversation explores tokenization's potential to create an ownership economy, why cultivation mindset beats consumption thinking for long-term wealth building, and what freedom from scarcity truly means in both dealmaking and life. GERRY'S JOURNEY: Gerry's path into venture capital came through painful education. After leaving law practice after just six months, he made his first investment at age 27, putting his entire life savings of $25,000 into a hazardous waste processing technology. He knew the space intimately from running lobbying for Indiana's Department of Environmental Management. The technology made sense. The market opportunity was clear. But the founder couldn't execute, and Gerry lost everything. That lesson kept him away from startup investing for a decade. Instead, he became a founder himself, launching HomeYeah.com during the dot-com boom. He acquired a small Indianapolis company with 25 lawn signs and built it into the 11th largest real estate company in Indianapolis by transactions, growing from zero to $1.8 million in revenue in just 20 to 24 months. The company sold to Help-U-Sell Real Estate in 2003, but not before Gerry experienced the challenge of raising capital outside traditional tech hubs. After the HomeYeah.com exit, Indiana University invited him to teach a new venture capital course. He's been there since 2004, creating what he calls a bridge between academic theory and real-world startup practice. Meanwhile, he co-founded Charlie Biggs Food Company, scaling it from zero to $10 million in revenue with distribution in over 1,000 retail locations before exiting through a private equity deal. FIRST INVESTMENT LESSONS: That initial $25,000 loss taught Gerry what he calls "avoiding the fool's tax." The fundamental insight was simple but profound. When you invest, you're really investing in founders more than ideas. He was simply a bad picker of founders at that point. The technology expertise didn't matter. Market knowledge didn't matter. What mattered was identifying founders who could execute through inevitable obstacles and pivots. This lesson shaped everything that followed. Gerry wouldn't touch startup investing again for ten years after that loss. When he did return, his approach centered on cultivating relationships with founders over time, watching how they respond to challenges, and building diversified portfolios that acknowledge most investments will fail. VENTURESTAKING MODEL: The VentureStaking approach emerged from Gerry's years of teaching and investing. The model allows investors to participate with as little as $10 in early-stage founders. Instead of writing large checks for immediate equity, venture stakers provide small grants to founders just getting started. If those founders break out and raise a real equity round, the stakers get invited to invest at 10 times their initial stake. The math works elegantly. Out of 25 investments of $10 each totaling $250, you might only see three worth backing in a real round. But when winners emerge, you've earned the right to participate in meaningful equity rounds without the traditional barriers to entry. This democratizes access while maintaining sophisticated portfolio construction principles. Gerry likens venture investing to poker rather ...