In this episode of the Relentless Growth Podcast, Chase Calhoun and Jack Maher break down one of the biggest questions real estate investors face: when to sell a rental property, when to do a cash-out refinance, and when to hold long-term.

They discuss how your end goal changes the math (10 paid-off rentals vs scaling a company), why today’s interest rate environment makes recycling capital harder, and the key mindset shifts that help investors stay active without getting forced into bad decisions. You’ll also hear practical rules of thumb like “the best time to sell is when someone wants to buy” and “the best time to borrow is when you don’t need it,” plus why taxes and depreciation recapture matter more than most investors realize.

Topics covered:

• Sell vs refi vs hold: how to choose the right move

• Building wealth vs building a business (different strategies)

• How higher rates changed deal structure and cash-out refis

• Avoiding “forced sales” and planning ahead for liquidity

• Capital gains, flips, cost seg, and depreciation recapture basics

• Staying in the game: flexibility, action, and long-term positioning

Perfect for new and experienced investors navigating rentals, portfolios, and growth in a changing market.