From Prison to Property Development with Kolaiah “Fuzzy” Jardine, Ep. 756

Kolaiah “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

• Fuzzy’s transformation from prison to property developer shows the power of mindset and purpose.

• “The crab in a bucket” mentality, surrounding yourself with the wrong people, keeps you stuck.

• Taking bold, decisive action (even when broke) can change your trajectory.

• Investing education is priceless when you’re ready to implement it.

• “The Pono Way” means people before profit—help others first, and wealth follows.

Topics

From Prison to Property Developer

• Fuzzy grew up in Oahu’s multigenerational households, surrounded by love but also by poverty and addiction.

• After a prison sentence for drug-related charges, he discovered real estate through a white-collar inmate who taught classes on investing.

• Determined to change his life, Fuzzy came out of prison with a new mindset and a mission.

Finding Purpose and Building Mindset

• Initial jobs included window washing, surfing instruction, and valet parking—three jobs just to survive in Hawaii.

• Realized hard work alone wasn’t enough; financial education was key.

• Discovered Rich Dad Poor Dad and began pursuing real estate investing as a way to create generational wealth.

The Turning Point: Fortune Builders

• While preparing to become a pilot, he heard a radio ad for a real estate training event and pivoted immediately.

• Borrowed $20K through a native Hawaiian loan and maxed out credit cards to join the program.

• His conviction came from being “sick and tired of working three jobs” and seeing his parents face foreclosure.

• 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

• Now leading 60+ projects focused on affordable housing on Hawaii’s Big Island.

• Emphasizes integrity and “The Pono Way”: helping families in distress before thinking of profits.

• Sees real estate as a means to restore opportunity for locals priced out of their own communities.

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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

• Get Fuzzy’s book Priced Out of Paradise on Amazon.com

• Visit fuzzyjardine.com to learn about his projects and mentorship opportunities

• Follow him on Instagram for real estate education and community impact stories

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