How to Win at Travel with “The Points Guy” Brian Kelly

10 snips

Mar 11, 2025

Brian Kelly, the Founder of The Points Guy and bestselling author, dives into the art of maximizing travel rewards and loyalty programs. He shares insights on turning travel into a financial strategy, revealing hidden perks and personal anecdotes from his travels and LGBTQ+ journey. Kelly emphasizes the significance of understanding points as more than just freebies but as a lifestyle tool. Listeners also get tips on smart spending, the importance of travel insurance, and an adventure-filled road trip through beautiful Colorado.

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ANECDOTE

Bucks County Roots

Jason and Brian Kelly discover they both grew up in Bucks County, Pennsylvania.
They reminisce about the area's unique blend of funkiness and affluence.

ANECDOTE

Coming Out Story

Brian Kelly shares his experience growing up gay in Bucks County and coming out after college.
He discusses the challenges and the relief he felt after sharing his truth with his parents.

INSIGHT

Authenticity Reigns Supreme

Authenticity is crucial for building trust and engagement with an audience.
Sharing personal stories, even if controversial, can strengthen connections and foster a loyal following.

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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

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