How He Pulled Off a $25K Maldives Trip Using Just Credit Card Points (ft. Dr. Roshan Kalra)

In this episode of Just a Couple of Dentists, we’re joined by Dr. Roshan Kalra — a dentist turned real estate investor who figured out how to turn everyday practice spending into a luxury, $25,000 trip to the Maldives… completely on points. Roshan walks us through his exact playbook, including what cards to use, how to stack bonuses, and why the Chase + Amex ecosystems are the best options for practice owners. Whether you’re brand new to points or already sitting on a stash you haven’t touched, this episode is a goldmine. You’ll learn: The “one-two punch” that turns $10K of spend into $225 of travel How to get 5 nights at the Waldorf Astoria for 800,000 Hilton points (instead of 5 million) Why paying taxes with a credit card can actually make you money The real story behind gift cards, IRS rules, and which cards dentists should never use If you're enjoying the podcast, please SUBSCRIBE on your favorite platform. We love putting out content for you...and your support means the world to us!