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 than roulette. You play many hands with small amounts. You fold most of them. But when you spot real winners, you bet heavy. This is cultivation versus consumption, a long-term wealth-building game that Warren Buffett exemplifies, having created 99% of his wealth after age 65.

THE COLLAPSING COST OF STARTING:

One of the most profound shifts Gerry identifies is how startup costs have collapsed. What required $5 million to build ten years ago can now be created in a day for $50 thanks to AI agents, no-code platforms, and cloud services. This changes everything about capital requirements and who can be a founder.

This trend combines with tokenization to create what Gerry calls an ownership economy. Instead of owning a few stocks generating passive income, people could hold tokens in 150 companies, each generating small amounts of passive income without traditional barriers to entry. The infrastructure for this future is being built now through blockchain technology and regulatory evolution.

UNIVERSITY VENTURE ECOSYSTEMS:

Gerry's work brings the VentureStaking model to universities, creating ecosystems where students, alumni, and faculty can participate in funding and building the next generation of startups. Indiana University has 70,000 students and 800,000 alumni. Imagine creating an arena where students pitch ideas, alumni back them with small stakes, and the community participates in the upside when founders succeed. Shared information, shared risk, shared prosperity.

This approach captures innovation traditional VCs miss entirely. Founders outside coastal hubs gain access to capital. Alumni gain access to investment opportunities typically reserved for accredited investors with six-figure minimums. Students learn by doing rather than just studying theory. The model scales to any university willing to build the infrastructure.

KEY INSIGHTS:

Geographic location shouldn't determine access to capital. Gerry experienced this firsthand with HomeYeah.com in Indianapolis. He wasn't in California. He didn't have the right connections. That challenge drives his current work at Doriot, focused on democratizing venture capital for founders and investors outside traditional hubs.

The Sam Altman example illustrates how network effects compound. Altman invested $15,000 in Stripe in 2009, now worth $650 million. That wealth creates access to more deals. Those deals create more wealth. The rich get richer not because they're smarter but because they have access. VentureStaking aims to expand that access.

Contracts matter, but people matter just as much. Gerry's experience shows that when something seems too easy, like tenants responding unusually quickly to lease documents without redlines for 10-15 year commitments, it raises red flags. You can have perfect legal documents but still face challenges if you're working with the wrong people.

THE SHARK TANK STORY:

Gerry shares his Shark Tank experience where his former student pitched a business and received a $250,000 offer from Mark Cuban for 35% equity. Gerry advised him that existing SAFEs would push