
Relentless Growth Podcast
Should You Sell or Hold Your Rental Properties? | Real Estate Investing Strategy
Should you sell a rental property or hold it for the long term? For many real estate investors, the goal is to buy properties and never sell. But as your portfolio and business grow, the answer isn’t always that simple. In this episode of the Relentless Growth Podcast, Chase Calhoun and Jack Maher break down the sell vs. hold decision in real estate investing and why flexibility can be one of an investor’s biggest advantages. Chase and Jack discuss when it makes sense to hold through a slow market, when selling can free up capital for new opportunities, and why the right decision depends heavily on your long-term goals. They also cover: When selling a rental property can make sense Why Chase is selling some properties to fund new development Turning a property into a rental when it won’t sell Opportunity cost and trapped equity Cash-on-cash return vs. return on equity Why investors need realistic property valuations The costs of selling, including commissions, closing costs, and potential taxes Knowing when to shift into a different real estate asset class Why staying flexible can help you survive slower markets The goal isn’t necessarily to never sell or to constantly trade properties. It’s to understand what you’re trying to accomplish and make decisions that keep you in the game long enough to reach it. Chase and Jack also share updates from their businesses, including progress on a Middle Tennessee apartment development, Jack’s new HVAC company, and Apex Professional Construction’s growing commercial construction work. Subscribe to the Relentless Growth Podcast for weekly conversations about real estate investing, construction, entrepreneurship, business growth, and building for the long term.

