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!

[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

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.

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.

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.

Episode 350 - Tom Dillon on Fractional CFOs and Alternative Funding Sources: Learn how fractional CFO services help companies explore diverse funding options beyond traditional venture capital.

Episode 351 - Solocast on Deal Structures Beyond M&A and Capital Raising: Explore joint ventures, strategic alliances, licensing agreements, and other creative partnership models that expand growth options.

Episode 89 - Sherisse Hawkins on the Capital Raising Journey: Discover the practical realities of securing investment as a founder and navigating the funding landscape.

Episode 85 - Nick Adams on Seed Stage Venture Capital Funds: Understand how traditional VCs evaluate early-stage deals and what metrics matter most to institutional investors.

Episode 175 - Natasha Miller on Developing Strategic Partnerships: Master the concepts of shared risk, shared resources, and creative collaboration structures that bring communities together.

Episode 185 - Maximilian Rast on How to Raise Capital for Your Company: Build the fundamentals of capital raising that apply across venture, real estate, and business growth strategies.

Follow DealQuest Podcast:
LinkedIn: https://www.linkedin.com/in/coreykupfer/
Website: https://www.coreykupfer.com/

Follow Gerry Hays:
LinkedIn: https://www.linkedin.com/in/gerryhays/ 
Company: https://doriot.com  
Twitter: @gerryhays

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

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 TRENDS:

Interest rate movements create near-term positivity while inflation continues hitting sectors unevenly, creating inefficiencies and opportunities. The retail apocalypse predictions following Covid haven't materialized because people still crave experiences. Drive-throughs represent a clear trend as efficiency becomes paramount - almost every concept has figured out how to use them successfully, including Chipotle proving the model works for food types that seemed ill-suited initially.

Perfect for real estate investors considering raising outside capital, operators building broker networks, and anyone interested in how successful commercial real estate investors structure deals and protect investor capital.

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

FOR MORE ON NICK JONES:
https://www.alakai-capital.com
https://www.linkedin.com/company/alakaicapital/
https://www.linkedin.com/in/nickjonesrealestate/
https://www.instagram.com/alakaicapital/

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!

[00:00] - Introduction: Nick Jones' journey from professional wakeboarder to real estate CEO
[02:21] - Growing up around real estate near Microsoft and Nintendo in Redmond, Washington
[04:21] - Pivoting from professional sports to commercial real estate after family tragedy
[06:09] - The first deal: A vacant Taco Bell property that set the foundation
[07:44] - Why Nick started with commercial properties instead of residential real estate
[09:17] - Evolution of financing and capital raising strategies across 70+ deals
[11:44] - Syndication vs funds: Why individual deal syndication works better
[13:26] - The decision to raise outside capital and the weight of investor responsibility
[14:15] - How grandfather and father approached real estate differently without raising capital
[16:15] - Learning from deals that didn't go as planned: Contracts and people both matter
[19:05] - Due diligence challenges with high-credit tenants who won't share financials
[20:23] - Covid revelation: Mom and pop tenants paid while credit tenants had attorneys advise stopping rent
[22:28] - How to source properties and build broker relationships that generate deal flow
[25:52] - The truth about "off-market" deals in today's transparent commercial real estate market
[27:59] - Balancing commercial real estate with selective angel investing for asymmetric returns
[31:09] - Relying on specialized partners for angel investing due diligence
[34:10] - Current market trends: Interest rates, inflation, drive-through retail, and efficiency plays
[37:52] - Whether Nick's investor pool is set and how new investors can learn more
[40:00] - What freedom means beyond financial independence: Physical, mental, and relationship dimensions
[41:22] - The danger of gaining financial freedom while losing physical health or relationships
[42:25] - Corey's "ideal life now" philosophy versus waiting for retirement

Nick Jones has been involved in commercial real estate management, investment, development, and brokerage for over 20 years. Each role has added valuable perspective, introducing various angles and strategies to evaluate every opportunity Alakai Capital pursues. Currently, he serves as CEO managing acquisitions, development, and capital markets. Throughout his career, Nick has underwritten and acquired over 70 commercial investments and developments representing more than $250 million in value. He currently oversees 800,000+ square feet of industrial, retail, office, and medical office assets.

Nick graduated summa cum laude from the University of Central Florida while simultaneously competing on the World Tour as a professional wakeboarder, earning a podium finish at the World Championships in 2011. He is an active member of ULI, ICSC, and NAIOP.

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.

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.

Episode 191 - Jack Gibson: Achieving Financial Stability Through Real Estate

Episode 183 - How To Invest In Real Estate with Kent Ritter: Explore different approaches to real estate investing and building investor relationships.

Episode 353 - Build Community-Driven Real Estate Ventures with Ryan Andrews: Discover how community-focused approaches can enhance real estate investment strategies.

Episode 185 - How To Raise Capital For Your Company with Maximilian Rast: Master the fundamentals of capital raising that apply across real estate and business ventures.

Episode 352 - Proven Strategies for Scaling Companies Through Strategic Partnerships with Nahed Khairallah: Learn how strategic partnerships drive business growth beyond traditional capital raising.

Episode 213 - A Discussion on Business Partnerships with Corey Kupfer: Understand the legal and strategic foundations of creating successful business partnerships.

Follow DealQuest Podcast:
LinkedIn: https://www.linkedin.com/in/coreykupfer/
Website: https://www.coreykupfer.com/

Follow Nick Jones:
LinkedIn: https://www.linkedin.com/in/nickjonesrealestate/
Company: https://www.alakai-capital.com
Instagram: https://www.instagram.com/alakaicapital/

commercial real estate investing, capital raising strategies, real estate syndication, syndication vs funds, broker relationships, tenant due diligence, credit tenant analysis, angel investing, real estate investment strategy, property investment, commercial property management, real estate financing, investor relations, deal sourcing, off-market deals, real estate partnerships, building wealth through real estate, entrepreneurship, business growth strategies, dealmaking

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:

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!

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!

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!

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!

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:

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!

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!

Think great communication in deals is about having the right words or perfect hand gestures?

After 35 years of negotiating deals, I can tell you this: all the tactical training in the world won't help if you haven't done the internal work to understand who you are and what you bring to the table.

In this episode, Dia Bondi breaks down why your leadership voice matters more than any communication skill. She turned a $30,000 project into over a million dollars by structuring it as a mix of cash and equity. She helped a client maneuver a complex secondary deal by crafting a multi-layered ask that positioned him as an equal partner. And she showed a founder how to create $10 million in value by painting a picture that helped an entire room recognize the moment they were in.

Dia shares her six attributes of clutch communicators, including how to:
Make strategic asks that create value for everyone (not just get you what you want)
Use killer setups that feel natural to your voice
Bridge your unique perspective to whatever you're building
Show up big in big moments even when it feels uncomfortable

This conversation reveals why "be authentic" is useless advice and what to focus on instead.

Perfect for founders heading into funding rounds, executives negotiating partnerships, or anyone who needs to speak powerfully when stakes are high.

• • •

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

• • •

FOR MORE ON DIA BONDI
LinkedIn: https://www.linkedin.com/in/dia-bondi/
Company: https://www.diabondi.com/
The Book: https://www.asklikeanauctioneer.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!

"Every time I get off the phone with you, I feel better... but I don't call because I don't want to pay the billable hour."

Alexandria Seydel heard this from clients constantly when she was practicing M&A law. So she made a simple offer: "What about once a month you buy me lunch and we go for 90 minutes and you get my brain."

Those lunch conversations changed everything. Alexandria realized she was more energized talking business strategy than drafting legal documents. Now as founder of Ripples Edge Advisors, she helps business owners prepare for exits before they're forced to sell.

Most owners think exit planning means getting financials in order and hoping for the best. Alexandria starts differently. She has clients close their eyes and picture life five years after selling: What does your typical day look like? Who are you spending time with? What gives you purpose?

Those answers determine whether you should target private equity (focused on returns) or strategic buyers (who care about legacy and team). The visioning exercise prevents what Alexandria sees constantly: post-exit depression, even among sellers who make life-changing money.

Right now she's watching clients in tech-adjacent industries get multiple serious offers in the same week. Legal tech, agricultural tech, climate tech - traditional industries adding technology are hot. But success isn't just about timing the market.

"If you were to go to Bali for three weeks, would your business run without you?" That's Alexandria's test for exit readiness. Most entrepreneurs think they're prepared until they actually try stepping away.

In our conversation, Alexandria breaks down her exit readiness assessment, explains why the visioning exercise matters more than most tactical work, and shares what's driving current M&A activity in her clients' industries.

• • •

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

• • •

FOR MORE ON ALEXANDRIA SEYDEL
LinkedIn: https://www.linkedin.com/in/alexandria-seydel/
Company: https://www.linkedin.com/company/ripples-edge-advisors/
Website: https://www.ripplesedgeadvisors.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!