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In this episode of Revolutionizing Your Journey, DeAndre Coke sits down with points-and-miles legend Greg Davis Keene (Greg the Frequent Miler) for an inspiring conversation about his evolution from tech professional to one of the most respected voices in the award travel world. Greg reflects on the early travel moments that ignited his passion, the accidental beginnings of the Frequent Miler blog, and the turning points that transformed a hobby into a full-time career.
The episode dives deep into Greg’s philosophy on trust, transparency, and evaluating deals with both intuition and data. He recounts some of his most memorable redemptions — including an extraordinary week on Richard Branson’s Necker Island, booked for 1.2 million Virgin Atlantic points — and shares what it felt like to be greeted by Branson himself upon arrival.
Greg also offers practical advice for newcomers, emphasizing the power of transferable currencies, learning from inevitable mistakes, and staying curious as the loyalty landscape evolves. This episode blends wisdom, storytelling, and strategy — a masterclass from one of the best in the game.
Key Highlights:
Resources:
Interested in Financial Planning?
Some of Our Favorite Tools For Elevating Your Points & Miles Game:
Note: Contains affiliate/sponsored links
Connect with DeAndre & Taryn:
Connect with Greg - The Frequent Miler:
Mentioned in this episode:
Check out this month's sponsor and support our show
Join the loyalty program for renters at joinbilt.com/journey
https://joinbilt.com/journey
By DeAndre Coke4.8
6565 ratings
In this episode of Revolutionizing Your Journey, DeAndre Coke sits down with points-and-miles legend Greg Davis Keene (Greg the Frequent Miler) for an inspiring conversation about his evolution from tech professional to one of the most respected voices in the award travel world. Greg reflects on the early travel moments that ignited his passion, the accidental beginnings of the Frequent Miler blog, and the turning points that transformed a hobby into a full-time career.
The episode dives deep into Greg’s philosophy on trust, transparency, and evaluating deals with both intuition and data. He recounts some of his most memorable redemptions — including an extraordinary week on Richard Branson’s Necker Island, booked for 1.2 million Virgin Atlantic points — and shares what it felt like to be greeted by Branson himself upon arrival.
Greg also offers practical advice for newcomers, emphasizing the power of transferable currencies, learning from inevitable mistakes, and staying curious as the loyalty landscape evolves. This episode blends wisdom, storytelling, and strategy — a masterclass from one of the best in the game.
Key Highlights:
Resources:
Interested in Financial Planning?
Some of Our Favorite Tools For Elevating Your Points & Miles Game:
Note: Contains affiliate/sponsored links
Connect with DeAndre & Taryn:
Connect with Greg - The Frequent Miler:
Mentioned in this episode:
Check out this month's sponsor and support our show
Join the loyalty program for renters at joinbilt.com/journey
https://joinbilt.com/journey

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