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This week on Breaking New Ground, we’re featuring a conversation that hits on something I think a lot of us in real estate eventually wrestle with: the shift from doing deals to building a company.
Nick Jones is a former professional wakeboarder who made the leap into real estate investing—first as a solo entrepreneur, then as the founder and CEO of Alakai Capital. What makes his story compelling isn’t just the athletic-to-entrepreneur path (although that part is fascinating), it’s how he’s intentionally built a real estate investment platform that blends discipline, systems, and culture to scale sustainably.
We talk about:
The rebranding of Alakai Capital and what it signals
How tech and AI are shaping real estate operations
The importance of syndication, investor relationships, and communication
What it really takes to go from “doing deals” to running a company with long-term vision
If you're in the business of building—not just investing—you'll get a lot from this one.
Listen now on The LineUp or wherever you get your podcasts.
—John
🚨 New Mini-Series Launch: Private Capital Perspectives
We're excited to launch a new mini-series on The LineUp — Private Capital Perspectives — where we sit down with private investors, family offices, and capital allocators to explore where they’re seeing opportunity, what challenges they’re navigating, and most importantly, how they’re overcoming them in today’s uncertain market.
Confirmed guests include:
A family office investor and former investment banker
A partner at a family office that focuses on real estate investment & development
An attorney specializing in structuring real estate joint venture partnerships and complex transactions
These are real conversations with real capital players — no fluff, just practical insights.
Stay tuned for the first episode — and let us know what topics you'd like to see covered. Shoot us a DM or note by responding to this email.
🔍 Summary
In this episode, Nick Jones, former professional wakeboarder turned real estate entrepreneur, shares his journey from elite athlete to the founder of Alakai Capital—a commercial real estate firm navigating the intersection of technology, investing, and company building. Nick reflects on his evolution from technician to CEO, emphasizing the importance of mindset, process, and culture in scaling a business. He discusses the rebranding of Alakai Capital to reflect its broader vision, the parallels between athletic discipline and entrepreneurial grit, and the increasing role of AI and technology in real estate operations. This conversation dives into capital raising, syndication, market navigation in today’s inflationary environment, and how investing in tech ventures compares with traditional real estate assets.
🧠 Key Takeaways
From Athlete to CEO: Discipline, motivation, and consistency from pro sports translate directly into entrepreneurship.
Rebranding Alakai Capital: Reflects a shift from solo investing to a team-oriented, growth-driven business model.
Technician to Business Owner: Transitioning roles requires learning new skills—delegation, leadership, and operational efficiency.
Company Culture Matters: Celebrating wins and building cohesion drives long-term success.
SOPs and Checklists: Implementing structure and systems reduces errors and enables scale.
Tech + Real Estate: AI and automation are reshaping how real estate companies operate and communicate.
Syndication as a Growth Tool: Raising capital from aligned investors allows for larger and more diverse deal execution.
Commercial Market Insights: Inflation and macro pressures create strategic investment windows.
Mentorship and Learning: Ongoing education and guidance are essential to adapt and thrive.
Investor Relations: Transparent communication builds trust and long-term investor partnerships.
🧭 Key Topics & Timestamps:
00:00 – Intro & Alakai Rebrand Nick discusses the mindset shift from investor to company builder and why a rebrand was necessary to embody their values of trust, expertise, and community leadership.
03:00 – Scaling with Systems Why hitting 5+ employees forced him to systematize—and how checklists, SOPs, and Asana transformed operations.
07:00 – Culture as Strategy Nick shares how predictive indexing helps build a performance-focused, authentic culture, and why he views team members more like athletes than family.
12:30 – Celebrating Wins Why high-performing teams need to take time to recognize achievements to reinforce vision and morale.
15:30 – Tech + AI in Real Estate How Nick's team uses AI (ChatGPT and others) to handle communications, lease abstracts, and investor reporting—and why human oversight still matters.
21:00 – Investing Beyond Real Estate A look at Alakai Ventures: LP investments in fintech, online marketplaces, and AI startups—and why Nick believes some of these bets can return 50–100x.
26:00 – CRE Market Outlook Nick discusses where he’s finding opportunity in CRE today—including value creation via rent growth in overlooked industrial and retail assets.
Keywords
Alakai Capital, entrepreneurship, company culture, technology in real estate, investing, commercial real estate, AI, business growth, team dynamics, leadership
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