

#425: From Accidental Landlord to 7 Rentals - Here’s How
7 snips Jul 7, 2025
In this insightful talk, real estate investor O'Shea Gordon shares his journey from accidental landlord to building a seven-property portfolio while managing a full-time job. He discusses his early renovation challenges and the lessons learned about market dynamics and managing finances. O'Shea dives into the differences between long-term and short-term rentals, the importance of location, and innovative financing strategies like cash-out refinancing. His experiences underscore the significance of informed decision-making and balancing personal life with real estate ambitions.
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First Home Turned Rental
- O'Shea bought his first home as a primary residence but it turned into a rental later.
- He overran his renovation budget significantly but ended up happy with the outcome.
Living Cheap To Save Big
- O'Shea saved aggressively by living cheaply without a car for about six years.
- He invested in the stock market before using savings for a down payment.
Fixer Rental With Family Help
- O'Shea bought a 2008-2009 built rental near downtown St. Pete and renovated it with his dad.
- The property had roaches and needed cleanup but rented quickly at $1,400-$1,500 initially.