DealQuest Podcast with Corey Kupfer Podcast By Corey Kupfer cover art

DealQuest Podcast with Corey Kupfer

DealQuest Podcast with Corey Kupfer

By: Corey Kupfer
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Why do some companies grow by leaps and bounds while others only inch forward? Simple. They embrace Deal-Driven Growth in addition to organic growth! DealQuest is where you learn how to strategize, prepare for, find, and complete deals to grow your company faster. Listen in as host Corey Kupfer takes you behind the scenes with some of the world’s most fascinating deal-savvy business leaders. This is the one place where they can share openly the secret to deals they have done (or failed to do) and the issues, opportunities, benefits, pitfalls and lessons learned. Here you learn first-hand all about: Powerful deals that require little capital, mergers, acquisitions, and tuck-ins, Joint ventures, partnerships, and strategic alliances, licensing, raising capital and onboarding key employees, negotiating, structuring, finding, valuing, closing and integrating deals. Don’t be the one at the table who doesn’t grasp the power of Deal-Driven Growth!© 2025 014078 Economics Leadership Management & Leadership Politics & Government
Episodes
  • 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
    Nov 19 2025
    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 mins
  • 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
    Nov 12 2025

    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 mins
  • 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
    Nov 5 2025

    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!
    Show more Show less
    32 mins
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