From Prison to Property Development with Kolaiah “Fuzzy” Jardine, Ep. 756
Release Date: 10/14/2025
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info_outlineKolaiah “Fuzzy” Jardine is a real estate developer, author, and co-founder of Hui Mastermind, a Hawaii-based community focused on empowering Native Hawaiians to build generational wealth. His journey took him from serving time in federal prison to creating a multimillion-dollar real estate portfolio and developing affordable housing for local families. As the author of Priced Out of Paradise, Fuzzy is on a mission to teach others how to invest “the Pono way”—with integrity, community, and purpose.
Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.
Key Takeaways
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Fuzzy’s transformation from prison to property developer shows the power of mindset and purpose.
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“The crab in a bucket” mentality, surrounding yourself with the wrong people, keeps you stuck.
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Taking bold, decisive action (even when broke) can change your trajectory.
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Investing education is priceless when you’re ready to implement it.
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“The Pono Way” means people before profit—help others first, and wealth follows.
Topics
From Prison to Property Developer
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Fuzzy grew up in Oahu’s multigenerational households, surrounded by love but also by poverty and addiction.
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After a prison sentence for drug-related charges, he discovered real estate through a white-collar inmate who taught classes on investing.
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Determined to change his life, Fuzzy came out of prison with a new mindset and a mission.
Finding Purpose and Building Mindset
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Initial jobs included window washing, surfing instruction, and valet parking—three jobs just to survive in Hawaii.
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Realized hard work alone wasn’t enough; financial education was key.
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Discovered Rich Dad Poor Dad and began pursuing real estate investing as a way to create generational wealth.
The Turning Point: Fortune Builders
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While preparing to become a pilot, he heard a radio ad for a real estate training event and pivoted immediately.
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Borrowed $20K through a native Hawaiian loan and maxed out credit cards to join the program.
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His conviction came from being “sick and tired of working three jobs” and seeing his parents face foreclosure.
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Worked for free to gain hands-on experience and eventually became the go-to construction and development partner for other investors.
Building Affordable Homes and a Legacy
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Now leading 60+ projects focused on affordable housing on Hawaii’s Big Island.
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Emphasizes integrity and “The Pono Way”: helping families in distress before thinking of profits.
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Sees real estate as a means to restore opportunity for locals priced out of their own communities.
📢 Announcement: Learn about our Apartment Investing Mastermind here.
Round of Insights
Failure that set Kolaiah up for success: Going to prison—being forced to reevaluate his life gave him clarity and purpose.
Digital or mobile resource: TruePeopleSearch.com. Great for finding owners of distressed properties to connect directly.
Book recommendation: Rich Dad Poor Dad by Robert Kiyosaki.
Daily habit: Prayer, expressing gratitude daily for where he is and the opportunities ahead.
#1 insight for building generational wealth: Dial in your “why.” Once you know it, nothing can stop you from achieving success.
Favorite restaurant in Honolulu, HI: Zippy’s.
Next Steps
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Get Fuzzy’s book Priced Out of Paradise on Amazon.com
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Visit fuzzyjardine.com to learn about his projects and mentorship opportunities
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Follow him on Instagram for real estate education and community impact stories
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