How Frequent Miler Became a Points and Miles Powerhouse (The Greg Davis-Kean Story)
What happens when a tech-minded traveler gets obsessed with squeezing value out of every dollar and every mile? You get Frequent Miler, one of the most trusted names in points and miles, and a blueprint for how to play this hobby for both fun and long-term success.
This is the story of how Greg Davis-Kean went from regional road trips and casual work travel to business class flights, private island weeks with Richard Branson, and a full-time career teaching people how to use points and miles the right way, with trust at the center.
From Regional Drives to Sydney: Early Sparks for Travel
Greg always liked travel, but it started small. As a young adult, he and his wife mostly did regional drives, not epic international adventures. They talked about big trips like Hawaii and Australia, but there was a mental block.
They kept thinking, “We need 2–3 weeks” to make a long-haul trip worth it. With careers and limited vacation time, that window never seemed to appear.
Then his wife found a wild sale on flights to Sydney.
They checked their calendars and realized they could only carve out a single week. Flight time would eat up a chunk of that. Still, the fare was so cheap that they looked at each other and said:
“What the heck? This is so inexpensive.”
They went for it. They flew to Sydney, stayed in the city and surrounding region, and even with only about six real days on the ground, it was fantastic. That trip quietly rewired how they thought about travel.
Instead of waiting for the perfect multi-week window, they started using one-week breaks to do the trips they had always dreamed about. Hawaii was next, but they stopped trying to “do it all” in one go. They visited one island at a time over several years.
Big trips stopped being hypothetical and started being normal.
The Elite Status Wake-Up Call
The Hotel Check-In That Changed Everything
The turning point into points and miles started at a very ordinary place: a hotel check-in desk.
Greg was working in software development at Thomson Reuters and sometimes traveled to other offices. On one of those trips, he checked into a hotel alongside a coworker. The front desk agent handed his coworker a pile of goodies, announced an upgrade, and showered him with perks.
Greg got a normal room key.
He did a double take and asked his colleague what was going on. That is when he first heard about hotel elite status and how it unlocked upgrades, gifts, and special treatment.
Airline Status for the Whole Family
He already had a hint of airline status from earlier travel. That Sydney trip had actually pushed his whole family into silver status on Northwest (later Delta), including his 9‑year‑old son. Seeing his kid with elite status was pretty fun.
But seeing other people, especially people he knew, get upgraded when he did not left him kind of jealous. He wanted those perks too.
That feeling set off the next phase.
A No-Travel Decree and a New Obsession
In 2011, Thomson Reuters issued a strict rule: no more work travel unless you were going to see customers. Greg’s trips had been to internal offices, so his work flying stopped overnight.
He had climbed to Delta Gold and loved the upgrades when they appeared. Now he could see that status slipping away. Personal trips with his wife might sustain silver, but keeping Gold looked impossible.
So he did what many of us do at that moment. He went to Google and typed something like “how to earn elite status without flying.”
That search took him into FlyerTalk, MilePoint, and early points and miles blogs. It hit him right away:
- If you earn a lot of points and miles, you can skip chasing status and book first class and luxury hotels from the start.
- There are shortcuts to status through spend, promos, and partner deals if you still want it.
This mix of optimization, math, and tactics clicked perfectly with his tech brain. The hobby grabbed him fast and hard.
The First Redemption That Made It Real
Once he understood the basics, Greg did what many of us do. He started signing up for rewards cards and collecting welcome offers.
Very quickly, he booked a family trip to London:
- Business class flights
- A stay at an InterContinental hotel on points
He already knew, at a logical level, that this stuff worked. Seeing it play out in his own life changed everything. That trip was his proof of concept.
He came home thinking, “Everyone I know needs to understand this.”
But back then, social media was not what it is today. The only way to broadcast something to all your friends and family was email, and he knew that would explode into dozens of separate question threads.
So he came up with a simpler idea: start a small blog, write up what he was excited about, and send people links instead of long one-off explanations.
At that point, he had no plan to earn real money from it. If you had told him he might earn a dollar in a year from ads, he would have believed you.
Naming “Frequent Miler” and the Early Blog Days
When he picked a name, he thought small. He checked to see if “Frequent Miler” was available as a handle on FlyerTalk and Twitter. It was, which was all he cared about.
It did not even occur to him to check if frequentmiler.com was available. He was not thinking in terms of building a brand or owning a premium domain.
The domain was already taken, so for years he operated on less-than-ideal URLs and blog hosting setups. He even started on a simple WordPress address before moving to BoardingArea hosting.
During the pandemic, after many years of asking, he finally managed to buy Frequent Miler as a domain from the company that held it but was not using it.
The site that had started as a simple way to avoid sending long emails now had a real home.
BoardingArea, Kiva Microloans, and a Surprise Invite
Very early on, Greg found a strategy in another blog, Frugal Travel Guy, that let him earn Delta elite status through spend. It used microloans via Kiva, a platform that lets you fund small loans to borrowers around the world using a credit card.
- The card charges coded as purchases,
- The loans usually got paid back over time,
- And he generated huge amounts of spend safely.
He wrote about that in detail and joined online conversations about it. That caught the eye of Randy Petersen, the founder of BoardingArea, a leading host network for travel blogs.
Within a few weeks of starting his blog, Randy’s team emailed and asked if he wanted to join BoardingArea. At that time, many heavy hitters in the space were already there, so the invite felt surreal.
Of course he said yes.
You can still read Greg’s updated thoughts on that microloan strategy in his Kiva points-earning guide.
From Conference Curiosity to Full-Time Leap
Seeing the Business Side at BlogWorld
Soon after joining BoardingArea, Greg went to a conference in New York called BlogWorld. It was his first real look at blogging as a business.
He met other writers he had been reading for years, like the minds behind Mommy Points and Deals We Like. He also sat through sessions on topics he had not cared about before, like blog monetization and podcasting.
One key conversation stood out. Jen from Deals We Like explained credit card affiliate links and how bloggers earned a commission if readers applied through their links and were approved.
Greg thought, “If people are going to sign up anyway and want to support me, that seems fine.” He signed up for affiliate programs, but he did something unusual.
He put all his links on a separate page, did not push them aggressively, and rarely even linked to that page from his posts. He wanted a clean line between what he recommended and how he might get paid.
From a pure business perspective, that was not smart. From a trust perspective, it was the foundation of what came next.
A Reorg, a Severance, and a Big Bet on Himself
In early 2012, Thomson Reuters went through yet another reorganization, and Greg’s whole area was eliminated. He had two choices:
- Apply for a new role inside the company, or
- Take a severance package
He had been there 16 years, so the severance came out to about two weeks of pay for every year worked, close to eight months of salary.
It took him about a second to choose the severance.
He went home and told his wife, “I want to try being a full-time blogger.” At that moment, Frequent Miler was maybe earning a couple hundred dollars total. It sounded insane on paper.
But the traffic was growing quickly, and the severance gave him runway. He promised that if it was not working by the end of those eight months, he would look for another job.
He never had to make that search.
Trust First: How Frequent Miler Handles Credit Card Money
The biggest trust issue in the points and miles space sits right where Greg stepped in: credit card affiliate links.
Readers feel like they know the bloggers and podcasters they follow. That makes it easy to just say, “They say this is a great card, I’ll apply.” Some sites abuse that trust by pushing whatever pays them the most, even when better public offers are available elsewhere.
Greg drew a hard line early:
- If he showed a credit card offer, it had to be the best public offer he knew of,
- Even if he did not earn a commission on it,
- And he kept his content decisions separate from revenue.
At one travel show in New York, he gave a talk and pointed this out live. He told the audience they could go to Frequent Miler and see a 150,000‑point offer on a certain premium card, while almost every other site was still showing the inferior 100,000‑point affiliate offer.
He also built systems that push against bias. On pages where Frequent Miler lists many cards, they do not sort by commission. They estimate how much value a typical person can get in the first year and sort by that instead. Often, the top-ranked picks do not pay them anything.
When he started hiring, he kept that firewall in place. His first full-time hire, Nick Reyes in 2017, does not even see the affiliate payout data. Pay is not tied to which cards get written about. Greg wants his team writing about what is interesting and useful, not what happens to pay.
That approach built deep loyalty and made Frequent Miler a go-to resource for people who want honest recommendations.
If you like using tools to find strong deals and fair redemptions, you will probably also enjoy BoldlyGo’s own Point Redemption Calculator tool, which helps you see whether a specific booking is a smart use of your points.
Beginner Content vs Deep Nerdiness
Frequent Miler serves a funny mix of people:
- Brand-new travelers trying to book their first award
- Hardcore hobbyists juggling dozens of cards
Greg is honest that they do not always strike the perfect balance. The team does create starter guides and intro content, but on the podcast and the blog they usually talk at the level that excites them.
That might mean an episode full of Japan Airlines mileage sweet spots or the right way to use obscure programs.
Yet plenty of beginners listen anyway. Greg compares it to reading an article about a medical breakthrough. You might not understand every term, but you can still appreciate the story and the results. Over time, listeners and readers start to connect more dots, and some of them go from “no cards” to “20, 30, or more cards” as they gain confidence.
If you enjoy learning by listening, the Revolutionizing Your Journey podcast is another place to hear these stories from both sides, with Greg appearing as a guest in this very episode.
How Greg Judges a “Good” Deal
When something new pops up, Greg usually does not need an elaborate spreadsheet to know if it is newsworthy. After more than a decade in the hobby, he has a strong sense of what “normal” looks like.
If a hotel chain runs a promo where a segment of members can earn, say, 50 points per dollar for the rest of the year, that sounds nice, but it might take a bit of math and fine print reading to realize how strong it really is. He will often break down:
- What the points are worth per dollar of spend,
- Who can actually qualify based on status requirements,
- And whether it is worth shifting behavior to chase it.
For his own travel, he uses a mix of intuition and rough valuation.
Frequent Miler publishes Reasonable Redemption Values (RRVs), which are their estimates of what is fair value for each currency, usually in cents per point. For example, if an RRV is 1.5 cents per point and a flight only gives you 1 cent per point, that is not a great use for most readers.
Greg uses RRVs to guide the content, but personally, he is more flexible. If he has a giant balance of Amex points, he is okay redeeming slightly under the RRV for a trip he really wants. With currencies that are harder to earn, like some Citi points, he holds out for redemptions that are well above the RRV.
Cents Per Point vs Experiences You Would Never Buy
People love to brag about getting “10 cents per point” on an Emirates first class ticket. That math usually comes from comparing the retail cash price of first class to the number of points used.
Greg does not obsess over the exact penny value on every redemption anymore. Often he just knows it is good enough.
His key insight is simple: the cash difference between economy and international first class is often 10 to 1. The points difference is often closer to 2 to 1.
That gap is where the magic lives. You can use your miles to buy a $10,000 experience you would never pay cash for. In his view, you value that at what the first class cabin actually costs, not at the economy fare you would have bought.
If you want help spotting good deals and planning those kinds of trips yourself, BoldlyGo’s comprehensive points & miles toolkit is a handy collection of award search and planning tools that pairs nicely with Greg’s philosophy.
Unforgettable Trips: From NYC with Family to Necker Island
A Hyatt Takeover in New York City
One of Greg’s favorite uses of points was not about flying at all. When his niece graduated high school, she wanted to celebrate with a trip to New York City.
Instead of just paying for his own room, Greg used Hyatt points to book around eight rooms at a nice Hyatt for the extended family for several nights.
Even when Hyatt prices were lower than they are now, that was a serious chunk of points. It is the sort of thing he never would have done with cash, but points made it feel natural to be generous.
A Week on Richard Branson’s Necker Island
The most legendary redemption in his life is easy to name.
Back when it was possible, Greg redeemed 1.2 million Virgin Atlantic miles for a week on Richard Branson’s Necker Island for two people, all inclusive.
It took seven months of grinding out points and miles to get there, using every trick he knew.
The experience started before they even reached the island. They flew into a small nearby airport, where Necker staff met them, loaded them onto a speedboat, and handed out champagne. As they pulled up to the island, Richard Branson himself came out to welcome the small group of guests.
There were maybe 15 or 16 guests total and close to 100 staff. Activities, meals, and outings created a house-party feel, not a typical resort vibe.
The wildest part is that the trip did not just create memories, it created friendships. Greg and his wife still visit a couple from London they met there and have seen another couple from Grand Cayman multiple times. That week on points literally changed the circle of people in their lives.
You can find more of Greg’s stories and strategies on the main Frequent Miler site and on the Frequent Miler on the Air podcast.
Mistakes Happen, Even for Experts
Greg likes to compare learning points and miles to opening a new complex board game. You spread out the pieces, skim the rules, and everything feels confusing until you start playing and making mistakes.
Those mistakes are how you learn.
Recently, he booked a Preferred Hotels stay using Choice Privileges points. The booking path did not clearly show cancellation rules. After booking, the hotel’s confirmation email said he could cancel up to 24 hours before arrival, so he set a reminder.
When he went to cancel, the Preferred site showed a 72‑hour cancellation rule instead. The hotel and the booking system disagreed. He cancelled anyway and was lucky that the points came back.
The lesson is simple: when you book through a partner, always double check the hotel’s own site or a dummy paid booking to confirm the real cancellation policy.
He has dealt with other headaches too, like tight positioning flights, phantom award space, and points ending up stranded in hard-to-use programs. None of that means you are failing. It means you are learning.
If you would rather have help with the trickier bookings or complex itineraries, BoldlyGo offers points‑based travel assistance to plan and book trips using your rewards.
Where Greg Thinks Points and Miles Are Heading
Looking back over the last decade, Greg sees a few clear shifts:
- Earning points through spend is much easier
- Back then, 1x on everything and 2x in a few categories was standard
- Today, 3x to 6x multipliers on popular categories are common
- Welcome bonuses are far bigger
- 25,000 points used to be normal
- Now people hardly blink at 80,000 or 100,000 point offers
At the same time, banks have gotten smarter about blocking heavy churners. It is harder to repeatedly hit the same bonus, and card families have more rules.
On the premium side, issuers try to make cards “sticky” by packing them with credits and coupons tied to specific brands. The annual fees get higher, and you feel pressure to use the benefits constantly to justify keeping the card.
Greg increasingly prefers simpler long-term cards where the math is cleaner. For many travelers, that means focusing on strong earn rates and easy-to-use credits, instead of chasing every coupon.
Greg’s Core Advice for Beginners
If you are just getting started, Greg’s advice is straightforward:
- Just start. You will make mistakes. That is okay.
- Always pay your credit card bills in full. Interest and late fees wipe out any rewards gain.
- Focus on cards that earn transferable points, such as:
- American Express Membership Rewards
- Chase Ultimate Rewards
- Capital One miles
- Citi ThankYou points
- Some Wells Fargo points
If all else is equal, and you can pick between 100,000 miles with one specific airline or 100,000 transferable points, he would choose transferable every time.
Why? Because one day you will hear about a crazy deal that requires a niche program like Air France Flying Blue. You may think you have none of those miles, but in reality, you can likely move Amex, Chase, Citi, or Capital One points into that program when you need them.
That flexibility is where long-term value lives.
Favorite Flights, Hotels, and Places He Would Gladly Repeat
Best Flights
Two flights stand above the rest for Greg:
- Etihad First Apartment from Paris to Abu Dhabi on a daytime flight.
He had a private “room” with a separate recliner and bed, access to a shower, and enough time to enjoy the full food and drink service without rushing to sleep. - Japan Airlines First Class, also on a daytime route.
The hard product was not the flashiest in the sky, but the service and catering were out of this world. Every course and drink felt special.
Favorite U.S. Hotel
In the United States, one property has his heart:
- Alila Ventana Big Sur in California
It is a Hyatt all-inclusive tucked into the cliffs of Big Sur, one of the most beautiful stretches of coastline anywhere. Even if you never stay there, that region is worth a visit, but combining it with points at Ventana is next level.
Places He Wants to Go Back To
Two regions stay near the top of his “repeat” list:
- Lake Taupo, New Zealand, which he and his wife visited for the first time recently and loved
- The southwest of New Zealand’s South Island, around Milford Sound, Doubtful Sound, and Queenstown
He especially raves about an overnight cruise in Doubtful Sound. To get there, you take a boat across a lake, then a bus over a mountain, and by the time you reach the fjord, you have zero cell service.
You sleep on the boat in small cabins, share meals with fellow guests, kayak in quiet inlets, and watch dolphins and seals play nearby. It was one of the most memorable single experiences of his travel life.
Bringing It All Together
Greg Davis-Kean did not set out to build a business or a brand. He just wanted to keep elite status, then to share what he was learning with friends and family. Over time, his curiosity, love of optimization, and insistence on trustworthy recommendations turned Frequent Miler into a backbone of the points and miles community.
The big takeaways are simple:
- Use points to create experiences you would never buy with cash
- Value flexibility by focusing on transferable currencies
- Expect to make mistakes and learn from them
- Follow people and platforms who put your best interest ahead of quick commissions
If you want to hear the full conversation in Greg’s own words, watch the episode above and explore more stories and strategies on both Frequent Miler and BoldlyGo. Then start planning your own “Necker Island” moment, whatever that looks like for you.
