Revolutionizing Your Journey: Travel With Points & Miles How Greg the Frequent Miler Rewrote the Playbook on Points, Miles, & Travel Strategy (Ep. 104)
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:
- Greg’s beginnings: A spontaneous trip to Australia sparked his lifelong love of travel and his curiosity about maximizing rewards.
- Discovering elite status: A work trip that included surprising perks changed everything and led Greg deeper into points and miles.
- Starting Frequent Miler: What began as a simple resource for friends became one of the industry’s most trusted blogs.
- Authenticity first: Greg prioritizes consumer value over affiliate incentives — the foundation of his community’s trust.
- Evaluating opportunities: His approach blends intuition with analysis to identify real-world value.
- Memorable redemption: Greg booked a whole week on Richard Branson’s Necker Island for 1.2 million Virgin Atlantic points.
- Once-in-a-lifetime arrival: The Necker Island team greeted them with champagne on a speedboat, followed by Richard Branson welcoming them personally.
- Learning from mistakes: Missteps are part of the journey; each provides insight into better strategies.
- Advice for beginners: Focus on transferable points, start small, and take action even if you don’t feel entirely ready.
Resources:
- Book a Free 30 minute points & miles consultation
- Start here to learn how to unlock nearly free travel
- Sign up for our newsletter!
- BoldlyGo Travel With Points & Miles Facebook Group
Interested in Financial Planning?
Some of Our Favorite Tools For Elevating Your Points & Miles Game:
Note: Contains affiliate/sponsored links
- Card Pointers (Saves the average user $750 per year)
- Zil Money (For Payroll on Credit Card)
- Travel Freely
- Point.me
- FlightConnections.com
- Thrifty Traveler Premium
- LTH Online Points & Miles In Depth Course:
- Use coupon code "BOLDYGO" for a 50% discount!
Connect with DeAndre & Taryn:
- Instagram: BoldlyGo.world
- TikTok: BoldlyGo.world
- Website: BoldlyGo.world
- YouTube: BoldlyGoWorld
- YouTube: BoldlyGo.Travels
Connect with Greg - The Frequent Miler:
- Website: https://frequentmiler.com/
- Kiva Loans: www.frequentmiler.com/kiva
- Podcast: Frequent Miler on the Air Podcast
- Instagram: frequent_miler
- Facebook Group: Frequent Miler Insiders
Mentioned in this episode:
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