Building a rental portfolio while keeping his career.

Choosing a market he could build in

Garrison began investing outside California with a duplex in Michigan City, Indiana, where he had a trusted local connection. After owning it for several years, he sold and focused his efforts on Lexington, Kentucky.

Related reading: San Diego to Lexington: Garrison Haddon's Out-of-State Playbook

He wanted steady growth while continuing his W2 career, which provided capital for purchases. His first Lexington acquisition was a pair of neighboring duplexes. He also tried house flipping from across the country, but contractor problems and capital tied up in renovations slowed his rental purchases.

From small rentals to commercial multifamily

Garrison says he had about seven rentals when he began looking for help to grow. He joined Multifamily Strategy in early 2025, built relationships with local apartment owners, and bought a 9-unit building near a college campus that August.

Those relationships became central to his next opportunity. His realtor brought him an off-market 26-unit property. They worked through the operating information and negotiated terms, only for the owner to accept another buyer. Garrison stayed in contact. When that buyer could not complete the financing, he returned to the deal.

Putting the next purchase together

At the time of the interview, the 26-unit property was under contract. The proposed financing combined a bank loan, a seller-held portion, and Garrison’s own down payment. The local credit union he had used for the 9-unit building was willing to consider that structure.

Related reading: Inside My 44-Unit Section 42 Building: $1.8M, $0 Out of Pocket

Garrison reported 16 units owned at recording. The additional purchases discussed in the episode were still ahead of him. His story is one of patient expansion: keep earning, concentrate on a market, build local relationships, and continue the conversation when a deal takes longer than expected.

A 28-unit purchase in Louisville

In a separate community update, Garrison reported that his company, Haddon Capital, had purchased 28 units in Louisville, Kentucky. He described it as the largest deal of his career after ten weeks in escrow, and thanked his wife, partners, broker, and Christian for their support.

That post documents a completed Louisville acquisition. It is a different property from the 26-unit Lexington transaction discussed in the interview, so the two accounts are presented separately here.