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From Technician to CEO: Building Systems, Culture, and Scale with Nick Jones of Alakai Capital
In this episode of Breaking New Ground, John Pugh and Rachel Walters sit down with Nick Jones, Founder of Alakai Capital, to unpack the evolution from hands-on real estate technician to company builder and venture investor. Nick shares how the rebrand to Alakai Capital reflects his shift to leadership, systemization, and team culture—and why that’s been essential to scaling his platform.
We explore how his team implements standard operating procedures (SOPs), project management tools like Asana, and AI-powered workflows to boost efficiency and performance. Nick also dives into Alakai’s LP investments in tech and hospitality startups and how AI is transforming lease abstracting, investor communication, and portfolio reporting.
He closes by sharing where he sees commercial real estate opportunities in the current market—especially around inflation-driven rent growth in under-managed assets.
🧭 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.
🔗 Connect with Nick Jones:
🌐 Website: www.alakai-capital.com
💼 LinkedIn: Nick Jones Real Estate
📩 Investor Portal: Available via website
View all episodes
By John Pugh and Rachel WaltersIn this episode of Breaking New Ground, John Pugh and Rachel Walters sit down with Nick Jones, Founder of Alakai Capital, to unpack the evolution from hands-on real estate technician to company builder and venture investor. Nick shares how the rebrand to Alakai Capital reflects his shift to leadership, systemization, and team culture—and why that’s been essential to scaling his platform.
We explore how his team implements standard operating procedures (SOPs), project management tools like Asana, and AI-powered workflows to boost efficiency and performance. Nick also dives into Alakai’s LP investments in tech and hospitality startups and how AI is transforming lease abstracting, investor communication, and portfolio reporting.
He closes by sharing where he sees commercial real estate opportunities in the current market—especially around inflation-driven rent growth in under-managed assets.
🧭 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.
🔗 Connect with Nick Jones:
🌐 Website: www.alakai-capital.com
💼 LinkedIn: Nick Jones Real Estate
📩 Investor Portal: Available via website