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 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 him below 50% ownership. The founder turned down Cuban's offer. That "no" to Mark Cuban kicked off Season 4 of Shark Tank and generated publicity that proved more valuable than the deal itself. The company continued growing without the investment.
CULTIVATION VERSUS CONSUMPTION:
One of Gerry's most powerful insights addresses how society trains people for consumption rather than cultivation. We've made sports betting legal. Prediction markets are booming. We're training young people about fast-moving money and dopamine hits. But venture investing is a cultivation game. You're dropping seeds into the ground and watching what the universe brings back.
He gave a student $5,000 who wanted to build something in the travel industry. The founder pivoted to AI and Shopify and just raised $8 million at a $55 million valuation. That $5,000 investment is now worth over $200,000. The bet wasn't on the idea. It was on a founder who wouldn't quit. That's something you discover by playing the game, getting yourself into wealth-building activities where you're patient, watching, and learning.
FREEDOM FROM SCARCITY:
When asked about freedom, Gerry's answer cut to something fundamental. Being free from a scarcity mindset is profoundly important. Everything around us reinforces scarcity. But when you let go of that and realize how abundant things really are, it changes how you see opportunities. You can afford to be patient. You can take calculated risks. You can help others succeed knowing there's enough to go around.
This mindset applies to venture capital, to dealmaking, to entrepreneurship, and to life. When you operate from abundance rather than scarcity, you see opportunities differently. Capital formation is evolving. The question is whether that evolution will democratize opportunity or concentrate it further. Gerry's betting on democratization.
Perfect for investors curious about venture capital but feeling locked out of traditional opportunities, founders outside coastal tech hubs seeking capital, university administrators exploring venture ecosystem development, and anyone interested in how capital formation is evolving to become more accessible while maintaining sophisticated portfolio construction principles.
FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/gerryhays
FOR MORE ON GERRY HAYS:
https://www.linkedin.com/in/gerryhays/
https://doriot.com
FOR MORE ON COREY KUPFER
https://www.linkedin.com/in/coreykupfer/
https://www.coreykupfer.com/
Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.
Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Episode Highlights with Timestamps
[00:00] - Introduction to Gerry Hays and the VentureStaking model
[02:15] - Growing up around real estate and finding it boring initially
[04:30] - The $25,000 first investment loss and avoiding the fool's tax
[07:45] - Launching HomeYeah.com during the dot-com boom and growing to $1.8 million
[10:20] - Capital raising challenges outside traditional tech hubs
[12:30] - Selling HomeYeah.com to Help-U-Sell Real Estate in 2003
[14:15] - Teaching venture capital at Indiana University since 2004
[16:45] - Building Charlie Biggs Food Company from zero to $10 million in revenue
[19:30] - The VentureStaking model explained with $10 minimum investments
[22:15] - Why venture investing is poker, not roulette
[25:00] - The collapsing cost of starting companies from millions to dollars
[27:30] - Tokenization and the ownership economy vision
[30:45] - The $5,000 investment now worth $200,000 after founder pivoted to AI
[33:20] - Sam Altman's $15,000 Stripe investment now worth $650 million
[36:00] - Building venture ecosystems within universities
[39:15] - The Shark Tank story where student turned down Mark Cuban
[42:00] - Cultivation versus consumption mindset for wealth building
[44:30] - Warren Buffett creating 99% of wealth after age 65
[46:45] - Freedom from scarcity mindset in dealmaking and life
Guest Bio
Gerry Hays is the founder and CEO of Doriot, a platform focused on democratizing venture capital by expanding access for entrepreneurs outside traditional coastal hubs. He is also a Senior Lecturer at Indiana University's Kelley School of Business, where he has taught Venture Capital and Entrepreneurial Finance since 2004.
Gerry began his career in politics and law before founding HomeYeah.com, an online real estate platform that grew from zero to $1.8 million in revenue in 20-24 months and became the 11th largest real estate company in Indianapolis by transactions. The company was acquired by the private equity firm behind Help-U-Sell Real Estate in 2003. He co-founded Charlie Biggs Food Company, growing it to over $10 million in annual revenue with distribution in over 1,000 retail locations before exiting through a private equity deal. He also co-founded Apparel Media Group, later acquired by Custom Ink.
An active investor, Gerry has backed 75+ early-stage companies, several of which have raised over $20 million or achieved profitability. He has been investing in Bitcoin and Bitcoin Layer 2 infrastructure since 2013. Gerry is the author of The First-Time Founders Equity Bible and has led student venture immersion trips to Asia for over a decade.
Host Bio
Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast.
Show Description
Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster.
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Social Media
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Company: https://doriot.com
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Keywords/Tags
venture capital democratization, VentureStaking model, early stage investing, startup funding alternatives, university venture ecosystems, tokenization investing, accredited investor alternatives, cultivation mindset wealth building, venture capital accessibility, startup investment diversification, capital raising strategies, founder backing strategies, angel investing, entrepreneurship education, blockchain tokenization, ownership economy, portfolio diversification, founder selection strategies, dealmaking strategies
