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!

Episode Highlights with Timestamps

[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 ] - Evol