エピソード

  • Episode 379: Democratizing Venture Capital Through VentureStaking with Gerry Hays

    Episode 379: Democratizing Venture Capital Through VentureStaking with Gerry Hays
    2025/11/26
    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 ...
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    42 分
  • Episode 378: Building Commercial Real Estate Success Through Strategic Partnerships with Nick Jones

    Episode 378: Building Commercial Real Estate Success Through Strategic Partnerships with Nick Jones
    2025/11/19
    From professional wakeboarder to CEO managing $250M+ in commercial real estate investments, Nick Jones shares proven strategies for building successful real estate businesses through strategic partnerships, effective capital raising, and protecting investor interests. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Nick Jones, CEO of Alakai Capital, who has underwritten and acquired over 70 commercial investments and developments representing more than $250 million in value. Nick currently oversees 800,000+ square feet of industrial, retail, office, and medical assets across multiple states. WHAT YOU'LL LEARN: In this episode, you'll discover how to raise outside capital for your first commercial real estate deal while protecting downside risk, why syndication can work better than funds when you can close deals quickly with trusted investors, and the surprising truth about "off-market" deals versus listed properties in today's transparent market. Nick shares how to build broker relationships that generate consistent deal flow without constantly hunting for opportunities, due diligence strategies when high-credit tenants won't share financial information, and why Covid flipped conventional wisdom about credit tenants versus mom and pop operators. You'll also learn about the strategic value of balancing consistent real estate returns with selective angel investments, how to navigate market trends including drive-through retail and efficiency-focused opportunities, and what freedom means beyond just financial independence. NICK'S JOURNEY: Nick's path wasn't linear. Growing up near Microsoft and Nintendo in Redmond, Washington, he found real estate "incredibly boring" until witnessing how it connected to fascinating industries. After his father and grandfather passed away during his senior year of high school, Nick moved to Florida to pursue professional wakeboarding, eventually earning a podium finish at the World Championships in 2011 while graduating summa cum laude from the University of Central Florida. The dean of UCF's real estate program, whose son was also a professional athlete, reignited Nick's interest in commercial real estate investment and development. Nick started in land brokerage during 2011-2012 when Florida land was worth less than the buildings next to it, learning through challenging cold calls to developers. FIRST DEAL LESSONS: Nick's entry into investing came through a vacant Taco Bell property. Working with a broker partner, they secured the building, signed a 10-year lease with a new tenant, and only had to replace the HVAC and roof. The timing proved fortunate - securing 80% loan to value at 2% interest on an interest-only basis during the post-financial crisis recovery. That first deal taught valuable lessons about protecting downside risk and building tenant relationships while delivering one of his strongest returns ever. CAPITAL RAISING EVOLUTION: For his first capital raise, Nick bought an old bank branch all cash with plans to tear it down and build a quick service restaurant. To protect downside risk as a new sponsor, he structured it with no debt and two years of interest and tax reserves. After approaching friends' parents, fellow brokers, and creating a detailed investment memorandum, a tenant approached wanting to lease the existing building as-is with a 10-year lease. Nick refinanced at 50% LTV, pulled equity out, and used those proceeds to buy a second deal. That snowball effect has grown to approximately 100 investors making about 500 investments with his company. KEY INSIGHTS: Nick continues syndicating individual deals instead of raising funds because his deals follow similar patterns with consistent return theses. This approach gives investors freedom to select which markets and property types align with their preferences while maintaining speed to close. Managing investor capital creates heightened responsibility that sharpens every aspect of deal execution. Nick approaches it similarly to personally guaranteeing loans - while losing your own capital is unfortunate, losing someone else's carries profound implications for relationships and reputation. The biggest lesson from deals that didn't go as planned: contracts matter, but people matter just as much. When tenants respond unusually quickly to lease documents without redlines for 10-15 year commitments, it raises red flags. During Covid, high-credit tenants had attorneys advising them to stop paying rent while small bay industrial mom and pop tenants maintained perfect payment records. BROKER RELATIONSHIPS: The majority of Nick's deals come through brokers he's built long-term relationships with over years. These relationships prove valuable because brokers trust Nick will maintain confidentiality, move quickly through underwriting, and they understand his investment criteria. After years of exchanging deals and feedback, brokers know which opportunities match his thesis. MARKET ...
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    43 分
  • Episode 377: From Wall Street to Coffee Farms: Building Social Impact Businesses with Bob Bush

    Episode 377: From Wall Street to Coffee Farms: Building Social Impact Businesses with Bob Bush
    2025/11/12

    Think making money and making impact are mutually exclusive?

    THINK AGAIN.

    Bob Bush went from working on the RJR Nabisco LBO to advising Dubai's government to co-founding a coffee company with NBA legend Dikembe Mutombo.

    His approach? Commerce, not charity.

    After 30+ years structuring deals across Wall Street, Africa, and the Middle East, Bob discovered that sustainable social impact requires sustainable economics.

    Now he's disrupting coffee supply chains where farmers get just 6 cents of your $5 latte.

    Key Takeaways:

    • Why crossing cultural bridges creates the best deal opportunities
    • How to build "shock absorbers" into social enterprises
    • The power of democratizing investment through crowdfunding
    • Why alignment beats optimization in building meaningful businesses

    Tune in to this episode to hear Bob Bush share his journey from Wall Street to creating social impact businesses across continents. From his insights on the RJR Nabisco deal to building sustainable supply chains in Africa, this conversation offers invaluable perspectives for business leaders seeking to create both financial value and social impact.

    FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/bobbush

    FOR MORE ON BOB BUSH:
    https://www.linkedin.com/in/robertcbushjr/
    https://www.instagram.com/mutombocoffee/?hl=en

    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!
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    55 分
  • Episode 367: Building a Dealmaker Community: Lessons from Leading the EO Deal Exchange Conference

    Episode 367: Building a Dealmaker Community: Lessons from Leading the EO Deal Exchange Conference
    2025/11/05

    Just wrapped my second year chairing the EO Deal Exchange Conference, and the lessons were off the charts.

    Here's what happens when you put hundreds of entrepreneurs in a room focused on one thing: growing through deals.

    Three insights that stood out:

    The wisdom is already in the room. We ran deal speed networking sessions where members shared their specific needs (buying companies, seeking JV partners, raising capital). The collective knowledge and connections in that room solved problems in minutes that could take months to crack alone. Stop looking outside your network for every answer.

    Exit satisfaction is shockingly low. Dave Hirsch shared that only about 13% of entrepreneurs who successfully exit are actually happy afterward. His "Inner Board Meeting" concept helps you identify all the different voices and aspects of your personality that need to be satisfied by any deal you pursue. Powerful framework for avoiding founder depression.

    Lifestyle business isn't an insult. Silicon Valley prodigy Fallon Fatemi, who co-founded an AI company with Mark Cuban, shared that she'll never raise capital again. Not because capital is bad, but because her priorities have shifted. Build the business and life YOU want, not what others expect.

    • • •
    FOR MORE ON THIS EPISODE:
    https://www.coreykupfer.com/blog/kraftheinz
    • • •

    FOR MORE ON COREY KUPFER:
    https://www.linkedin.com/in/coreykupfer/
    http://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!
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    32 分
  • Episode 366: Founder Regret, Exit Clarity & What Money Can't Buy with Jodi Hume

    Episode 366: Founder Regret, Exit Clarity & What Money Can't Buy with Jodi Hume
    2025/10/29

    85% of founders have regrets about their exits. The research is clear. But here's what surprised me most about this statistic: almost none of them regret leaving money on the table.

    They regret the clarity work they didn't do beforehand.

    In my latest conversation with Jodi Hume, an advisor who works exclusively with founders and CEOs navigating acquisitions and exits, we explored what that clarity actually looks like:

    How to distinguish between what you can compromise on and what will keep you awake at night years later.

    Why energy management during due diligence directly impacts the quality of your decision-making.

    The identity piece nobody talks about: who you are after the company is no longer yours.

    How to protect yourself from making decisions born of depletion rather than strategy.

    The uncomfortable truth about founder burnout and when an exit might be the right call precisely because you've hit your limit.

    Jodi's approach is unusual. She's less interested in maximizing valuations than in ensuring founders actually get what they came for—and that they don't regret it afterward.

    Listen to the full episode if you're even thinking about an exit in the next few years.

    FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jodihume

    FOR MORE ON JODI HUME:
    https://www.linkedin.com/in/joditurnerhume/
    https://atthecore.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!
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    52 分
  • Episode 365: How One Stock Tripled to Fund a Real Estate Empire With Jaden Sterling

    Episode 365: How One Stock Tripled to Fund a Real Estate Empire With Jaden Sterling
    2025/10/22

    Concentration beats diversification. One stock. That's all Jaden Sterling bought during the 1990s. It tripled, became capital for 125 real estate deals, and eventually funded Sterling Stock Picker, a stock-picking platform now serving 3,000 investors.

    What most financial advisors don't tell you: diversification is what you do when you don't know what you're doing. When Jaden's clients at Merrill Lynch held 4-6 solid companies, they were pressured to sell and diversify into mutual funds. The math later showed holding those original positions would've beaten all the churn.

    The path to real wealth isn't about spreading money thin. It's about focused conviction in what you actually understand.

    I sat down with Jaden to talk about deal structures across real estate, concentrated stock investing, raising capital from customers instead of VCs, and why your relationship with money mirrors your relationship with yourself.

    FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jadensterling

    FOR MORE ON JADEN STERLING:
    https://www.sterlingstockpicker.com/jaden_sterling

    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!
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    41 分
  • Episode 367: Building Wealth Through Strategic Group Home Investments with Jon Wells

    Episode 367: Building Wealth Through Strategic Group Home Investments with Jon Wells
    2025/10/15

    I just had an incredible conversation with Jon Wells on the DealQuest Podcast about a real estate niche that most investors have never even considered.

    After 25 years in Denver real estate, Jon discovered something remarkable: group homes for mental health and sobriety programs that generate 6%+ cap rates with almost zero landlord responsibilities.

    Here's what struck me most from our discussion:

    1. Jon's "fix and flop" philosophy completely changed my perspective. "My best deals were the ones that didn't sell," he told me. Those failed flips that he couldn't unload? They became his most profitable long-term holdings and led him to this overlooked niche.
    2. The economics are compelling. While everyone fights over compressed margins in traditional real estate (Jon watched fix-and-flip profits shrink from 25% to barely 10%), group homes maintain 6-13% cap rates even in high interest rate environments. His mentor has accumulated 1,000 beds. Jon manages 30-40 beds that provide what he calls "a great living."
    3. The structure is brilliantly simple. Operators funded by Medicaid and grants handle everything - maintenance, tenants, daily management. Property owners collect rent. It's "as close to a triple net deal as you can do" in residential real estate.
    4. The vetting process Jon shared was eye-opening. Drawing from his 1990s experience helping people save properties from foreclosure, he applies rigorous financial analysis to operators. The key: finding those with grant funding, solid track records, and willingness to accept purchase options so they treat the property like their own.

    What impressed me most was Jon's disciplined approach to avoiding shiny object syndrome. After a syndication advisor told him "I wouldn't touch that with a ten foot pole," he pivoted back to what he knows works - paying off mortgages and creating owner-carry notes for stable, predictable income.

    The lesson? While everyone chases the same crowded strategies, the best opportunities often hide in markets others don't even know exist. Sometimes the path to financial freedom isn't about following the crowd, but about finding overlooked niches that match your values and expertise.

    Listen to our full conversation on the DealQuest Podcast where Jon reveals his complete framework for evaluating group home opportunities.

    FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jonwells

    FOR MORE ON JON WELLS:
    https://www.linkedin.com/in/jonwellsrealtor/
    https://abetterwayrealty.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!
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    38 分
  • Episode 363: When Mega-Mergers Go Wrong: Lessons from the Kraft Heinz Deal

    Episode 363: When Mega-Mergers Go Wrong: Lessons from the Kraft Heinz Deal
    2025/10/08

    Warren Buffett called it one of his biggest investment mistakes.

    The 2015 Kraft Heinz merger destroyed $63 billion in shareholder value while the broader market doubled.

    Key lessons for M&A professionals:
    • Consumer behavior trend analysis is critical for food industry due diligence
    • Aggressive cost reduction can eliminate innovation capacity in consumer products
    • Post-merger integration strategies must balance efficiency with brand development
    • Market research capabilities become essential during rapid cultural shifts
    • Strategic exit planning requires objective assessment of recovery prospects

    The complete merger failure analysis reveals why sophisticated investors missed consumer preference shifts toward natural foods and how 3G Capital's cost optimization strategy backfired in processed food markets.

    Essential listening for dealmakers in consumer products industries.

    • • •
    FOR MORE ON THIS EPISODE:
    https://www.coreykupfer.com/blog/kraftheinz
    • • •

    FOR MORE ON COREY KUPFER:
    https://www.linkedin.com/in/coreykupfer/
    http://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!
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    14 分