Leveraging AI for Automated Travel Planning with Credit Card Points

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

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