Are you leaving free travel on the table?

Brian Kelly, aka The Points Guy, is one of the world’s leading experts on travel and loyalty programs. What started as a blog in 2010 has become a massive platform helping millions of travelers maximize rewards and travel smarter.

In his new book How to Win at Travel, Brian shares everything he’s learned about the game of travel, from leveraging airline and credit card points to planning your dream itinerary so you can experience the world in ways you never thought possible.

Brian joins me to talk about why playing the points game is about more than just free flights—it’s a strategy for life. He also shares how he turned a side hustle into a travel empire and opens up about his experience growing up in a small town and coming out after college.

Whether you're a travel hacking pro or just getting started, this episode will reframe how you think about points and miles as a financial tool. Brian breaks it all down in a way that makes sense, showing you how to turn travel into a strategic investment while revealing lesser-known perks and insider tips that will allow you to travel smarter and truly win at travel.

PLUS, you’re going to hear the 5th and final installment of our Five Best Road Trips in the USA mini-series. I saved the best for last!

What’s your biggest travel hack or points win? I'd love to hear about it, and I hope you’ll share by sending me an audio message.

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Tune In To Learn:

Why being authentic will always reign supreme in life and business
Why Brian is passionate about Peace Jam and giving back through travel
Why points are not only an extremely powerful tool but an important safety net
The biggest mistakes people make with points and miles and how to avoid wasting your rewards
How to reframe stressful travel with a “karma points” mindset and have better experiences
The four main loyalty program structures and how understanding them can help you redeem points for maximum value
The one travel insurance mistake that could cost you big time
Hidden gem destinations you should add to your bucket list
And so much more

Resources:

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