Learn what you can expect from the TPG app with a senior product manager

On this week's "Talking Points," senior product manager Drew Macomber details what you can expect from our much-anticipated mobile app. Drew is a true points-and-miles enthusiast himself, and he and his team of developers are implementing tools to help you take your points further. His five years as a nomad may help inform your travel strategy, too, so you never miss a lucrative redemption again.

Based in Austin, Texas, TPG's product team has been developing the app for the past year with the goal of providing travelers with the right resources to optimize their points-and-miles strategy. The app is designed to help points-and-miles gurus and beginners alike maximize their loyalty by teaching them how to earn and burn, all while making the best use of their time. For example, you can expect more personalized content within the app. That means we'll provide you with content for your preferred airlines, home airport, preferred loyalty programs and more.

The app will also allow you to sync your credit cards and loyalty programs so you can view your points-and-miles portfolios in one place. You'll be able to track your balances, monthly limits, spend by category, and sign-up bonus progress. It's coming in summer 2020, so make sure to stay tuned for more updates.

In this episode, Macomber shares how he got his start in the loyalty space and identifies resources you can use on his website, Travel is Free. He reminisces with Brian, The Points Guy, about the early days of points and miles, and how finding a loophole within the 2005 U.S. Mint dollar coin-buying program brought him an opportunity to rack up airline miles. Without it, Macomber might not have been able to work remotely while traveling the globe with his wife for five years.

You can play this episode above, or wherever you choose to listen.

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Brian Kelly:
Welcome to Talking Points. I'm your host, Brian Kelly, The Points Guy, and we've got an interesting one for you today. We've got TPG's senior product manager, Drew Macomber, and he's gonna share all the cool ways the TPG app is gonna help you organize your points and miles and take some amazing trips. Yes, it's coming. I know we've been talking about it for a while, but we've been working on it to make sure it's extra amazing, so your patience will pay off. Plus, Drew is probably one of the most OG Points people in the world, he started the site Travel is Free, and is now a part of The Points Guy team. We're gonna get into his humble beginnings with, get this, cashing in coins for points and why his bank actually thought he was a scammer. So, get ready for the details on the TPG app. It's comin' y'all, in 2020. That's all coming up, right after this.

Brian Kelly:
Today, I'm coming to you from Austin, Texas, which happens to be the second largest TPG office. We've got a team of 15 engineers and product people working on the TPG app. And one of our newest hires here in Austin is a legend in the points world. He is the founder of travelisfree.com, which has been called the goat of all miles and points blogs. I'm really excited to announce that he is now a part of TPG and he's going to be leading development of tools, and we're gonna learn all about that today. So, Drew Macomber, thank you so much for joining us today.

Drew Macomber:
Yeah, man. Thank you.

Brian Kelly:
So, Drew, you're a foremost expert in points and miles, you know these programs in and out. Someone listening, what are some of the tools you've created? What are some of the other apps that you use? You know a lot of times, people are like, "Where do I begin becoming an expert?" What's your advice for that?

Drew Macomber:
I'd say first of all, just start earning, because it's hard. If I were just to explain to someone who's never heard of it, I'm sure you've seen this where their eyes -- like you can see what they're checking out. So, I just say start earning the points, and then once you have them and you go to use them, you'll really learn and you'll retain that information because you're going to book a trip. So, then it's about maximizing the miles you have. If you go to my resource page, so it's travelisfree.com/resources, there's a number of resources like this one is a chart that tells you which websites search for which airlines.

Brian Kelly:
So, for example, like on American Airlines, you know it kills me when people search for Hong Kong and you're going to pay peak pricing to fly on an American jet when the Cathay experience is so much better in any class of service and it's probably, if available, half the price or less, but people don't know because it doesn't show up online. So, your resource page, each currency that you have and where you're trying to redeem, you highlight what's not going to show online.

Drew Macomber:
Exactly.

Brian Kelly:
But teaching yourself how to use British Airways or Qantas, you can search for the availability, and then pick up and call. What are some of the other tools that you're particularly proud of for helping people maximize their points?

Drew Macomber:
Well definitely the one that is used the most or kind of brings people back are all the hotel maps. So, if you have Hyatt points or Marriott points or IHG points, you can look at where all the 5,000-point hotels are, and there are nice 5,000-point hotels across the world in each program, or whatever.

Brian Kelly:
So, you can filter by category on the map?

Drew Macomber:
Exactly.

Brian Kelly:
What are some of those hotels that are low categories that you've been really impressed by? Are there any ones in particular that you loved?

Drew Macomber:
Well, you know they always change but -- so some of them have probably changed a lot. One is in India, they have a Park Hyatt, I think, in Chennai that's 5,000 points. So, where else are you going to stay at a Park Hyatt for 5,000 points? It's just not going to happen. So, honestly, anywhere in India, in China, you're always going to get those deals. So, if you're really wanting to chase deals, you could do that.

Brian Kelly:
So, Delta notoriously took away award charts, so when you go to Delta.com, from my perspective, it's always kind of random pricing. You've kind of created a tool that sniffs out the cheapest ways to redeem Delta miles, explain that one a little bit and how does someone use it?

Drew Macomber:
So the crazy thing is, if you're looking for a domestic flight, using Delta miles, or if you're looking for a flight to the Caribbean or Mexico, the prices are different based on every city pairing. So, depending on if you're coming from Chicago or D.C., doesn't matter. Wherever you're going, each example is going to be different, and what I've created is a tool that allows you to type in your airport code and get all the cheapest prices so it's sorted in order of price. And, believe it or not, there are tons and tons of really cheap but cool or high-value Delta flights. So, lots of people found that they could fly to Mexico City or Cancun for 6,000 miles, or somewhere domestic for 5,000 miles. They have lots of good deals and it's hard to find because you don't know which cities to search. I'm just letting you show and find those cheapest deals.

Brian Kelly:
You are not the first person to extol the virtues of SkyMiles, even though they've been criticized by some for jacking up the prices on premium tickets. I know Richard Kerr on this podcast has talked extensively about how he gets huge value for him and his family from SkyMiles. So, that's what I like about this game of points and miles is if you just go with the conventional wisdom of group think, you often miss those really juicy redemptions. Not everyone is going to the Maldives in first class, that's not necessarily winning in points and miles. So, in general, people will say to me, "You've been in this game for a while now since the heyday, the recent heyday ... ;" some people will say that it's over, or there's naysayers saying that airlines are just increasing the amount of points and it's no longer worth it. What would you say to someone like that?

Drew Macomber:
You know I heard an interview with Randy Petersen, who created FlyerTalk, and he's been around for the miles space for, I don't know, 30 years. He says his entire career, people are always saying -- always saying -- that the miles game is over, and then you know there's the next thing to come along. That was way before the $1, the [U.S.] Mint [promotion, see below]. So, if that's the heyday, then like why was it dying before that? It just always changes. There's more card offers now. I told you I wanted to do a blog post showing how much the prices have increased over time, I just wanted a data-driven answer and wanted to show a cool chart, and I scrapped it because the chart looked flat. It was not interesting data visualization.

Brian Kelly:
There was no smoking gun that these loyalty programs are shot.

Drew Macomber:
The availability, I would say, has gone down, but other than that, there's way more opportunities, there's way more resources.

Brian Kelly:
This is the golden age of earning points. And yes, these cards have fees, but the perks are insane, too. So, not only are you earning points, there are crazy perks and protections and benefits. In terms of loyalty programs, the major programs aren't sometimes not the most lucrative. What are some of the off-beat loyalty programs that you would recommend people looking into for outsize value? Are you a LifeMiles fan? I know the LifeMiles program used to be ultra lucrative, and then it sort of changed the rules, but there's still sweet spots.

Drew Macomber:
So, the way I view it is almost every program has a sweet spot, and I ignored Delta for a long time because I listened to the chatter, and so I missed out on 5,000-mile flights to Cancun when really, I've probably paid 17 and a half thousand many other times. So, similarly with LifeMiles, there are huge value adds. There are huge deals to be had. So, I really like to keep my points in a transferable currency like Chase or American Express Membership Rewards, and then I can kind of look at all the award charts, and then kind of decide where do I want to transfer. Luckily, we're making an app that will instantly sort all the prices and show you if you have American Express points, these are all the best deals on this route. That's the way I like to view it.

Brian Kelly:
In 2014, we launched the first-ever TPG To Go app, which we had partnered up with Wallaby before buying them.

Drew Macomber:
I remember that.

Brian Kelly:
It was kind of clever. We had "pay with this" functionality, which we would help people choose which ... in 2014, Sapphire Reserve wasn't out, there were far fewer earn categories, and it was still confusing back then. A better blog reader and tracking spend, making sure you didn't get hit with any interest fees. We wanted to make it more simple. We pulled that about a year and a half ago in order to really regroup. I mentioned earlier in the podcast, we've got 15 full-time developers, not all on the app. Some of them are working on the site as well. The future of The Points Guy, you know, we're a media platform today, it's content. But the future is in tools, because it is dizzying. The logistics and the nitty-gritty details and keeping track of programs and redemptions and who shows on what, even for experts, it's very, very hard. So, your main role right now is helping our product and tech teams make sure that this tool is going to really work.

Brian Kelly:
So, I know we are going to be partnering up API-wise to some partners, but in general, we've got a team of building the logic behind these ... you know, when you think about the number of transfer partners and partners of partners, the amount of possibilities when redeeming and earning miles is crazy. You want to talk through a little bit about what you're excited about in the first version of the release?

Drew Macomber:
Yeah, I think it's exactly what I was trying to say earlier all in an app. If someone was getting started, or even if they're an expert, they have to look up: Where they can transfer. What are the prices? What are the got-yous like, fuel surcharges? Then look up where to search for award availability, and then figure out where to book. What if you could just do a search and it told you all that stuff? That's what I'm excited about and that's why I'm here. I love building consumer products, in general. I'm passionate about product and I'm passionate about travel. So, I got excited about coming here and working on this and I think that -- that out of the gate, is going to be immensely valuable. And I don't think people realize how hard it is to program all the routing rules into this thing, and then having that base allows us to do really cool things, take your balance ... if you have American Express points, it'll tell you what the best transfer partner is. If you have enough points, make recommendations based on that. I mean it will be pretty cool.

Brian Kelly:
There is this epidemic of points hoarding. A lot of people have tons of points, but then they get trigger shy like, should I redeem for this? Should I not? Is this the best transfer partner? I still get a lot of our reader emails and diatribes, people writing, "I've been reading the blog for five years and here's my life story. I want to go these dates to these destinations." And I'm excited to have technology that's going to help people and also help work to the goal. As you mentioned before, when people are like, "Oh, this sounds too complicated," but when you put the simple decisions like putting your lunch on this certain card every day, will actually help get you to the goal of going to Paris on your honeymoon, or whatever it is. We also acquired ExpertFlyer last year, I'm really excited to integrate ExpertFlyer so people can do alerts. So, say you want to go to Paris over a certain October 2020, there's nothing available today, but you can set alerts and we'll automatically push-alert you when that availability opens up.

Brian Kelly:
I mean there's so many things, I really am excited about the app. It's been a Herculean task to do and I know people are getting a little impatient, but trust me, it's going to be worth the wait. What advice would you give to someone who is just starting out in miles and points today?

Drew Macomber:
Definitely I'll reiterate exactly what I said earlier, it is a lot easier to learn when you're doing it as opposed to just, you can read a million blog posts and still have only surface-level understanding because you've read one of each program. Just apply for a card that earns Chase and American Express points, and I'm telling you, once you Google or look up -- how to -- what's the best use of these points, or I have a page of award charts and transfer partners on the resource page. Now you have American Express points, you can look up what are the transfer partners, and then you can look up award charts. Then, once you're playing around with it, it will make a lot more sense.

Brian Kelly:
All right. Coming up after the break, hear how Drew got into the points and miles game and some of his travel inspirations and tips. Keep it locked.

Brian Kelly:
Welcome back to Talking Points and my conversation with TPG's senior product manager, Drew Macomber, who is helping to build the TPG app coming summer 2020. Let's jump back into it. So, Drew, let's skip to the basics. How did you get into this crazy miles and points world? What was that first draw that got you in?

Drew Macomber:
Yeah, actually, I read a book that talked about miles and points being earned by buying $1 coins, it was actually Chris Guillebeau's book. It came out in 2009.

Brian Kelly:
I was in one of his books, he interviewed me. I remember when I first started blogging, he had a paid community where you had to pay to get tips in the loyalty world. So, what did you do after reading the book?

Drew Macomber:
So, I think I just Googled what this $1 coin thing was about, earning miles for free sounded pretty appealing. I was kind of thinking about getting married and I wanted to keep traveling, but you know didn't have a lot of money, but I knew I wanted to travel the world. I just absolutely knew that was a thing.

Brian Kelly:
So, the U.S. Mint thing was probably one of the most epic points-earning opportunities of all time. For those listening, there have been NPR and Wall Street Journal stories about it, but basically, the gist is you could buy them with free shipping. So, basically, you could put them on a credit card with no fee, earn, let's say $10,000, get those coins, and then go straight to the bank, deposit them, and then pay off your credit card bill, earning you almost free points.

Drew Macomber:
Yeah, exactly. We did that very hardcore, we were buying-

Brian Kelly:
So, you found out about it while it was still going on?

Drew Macomber:
Oh, yeah, definitely.

Brian Kelly:
Today, people will ask me, "Hey, is it still possible to get millions of free points by getting truck loads of coins?" And I'm like, "That ship has long sailed."

Drew Macomber:
Oh yeah, it died in I think, 2011 or 2012. But yeah, at the time, it was awesome, and because I was getting credit cards that had high spend requirements that I couldn't meet at the time, so I bought $1 coins, originally just to meet the $3,000 requirement. So, I'd have $3,000 of coins show up and take them to the bank. And then, I don't know if you remember this, but there was a cashback portal offer to get cashback on American Express gift cards, so then I could buy $1,000 gift cards, and then that helped me get around the [rule of] one card number per thousand dollars of coins. So, then I was getting cashback to buy thousands of dollars-

Brian Kelly:
So, you took it to an extreme. So, you started off slow, and then did you get addicted?

Drew Macomber:
Well, yeah. How can you not? So-

Brian Kelly:
Were you renting U-Haul trucks to take in your coins to the bank?

Drew Macomber:
No, but the car was slanted.

Brian Kelly:
Had the sparks coming out from behind you as you're driving to your local bank.

Drew Macomber:
Not good for suspension and they are that heavy, I'm totally serious.

Brian Kelly:
What was the amount that you could carry? Was it 1,000?

Drew Macomber:
No, maybe 10,000, but we wouldn't carry them. We'd put them in rolling bags, and then we just looked like troublemakers rolling up to the bank and-

Brian Kelly:
Did the banks ever give you a hard time?

Drew Macomber:
Totally. So, one time, we went into the bank and the bank manager told us no. Instantly, I could see this skepticism. I had $20,000 in coins and they've never been unwrapped, and they're like, "I've never seen these Native American coins," and I was like, "They're U.S. Mint and you're a banker, like you should know this."

Brian Kelly:
Oh, so he thought it was full fraud. He wasn't sick of other people doing it, he was just like, this is shady?

Drew Macomber:
Yeah. It probably had a lot more to do with me than the coins. So-

Brian Kelly:
You do look pretty shady.

Drew Macomber:
So I looked up where another bank was and we went down to the next bank, I deposited all the coins and went home and went on with my day. About an hour later, I got a phone call from the same bank manager, apparently manager of both branches, and the bank manager actually debited my account. So, all the coins are gone, and I still owe 20k on my card, you know. And so all the coins were gone. I called up the bank, the support line, and they instantly took care of it. They called the bank.

Brian Kelly:
So, luckily, that got turned around and you were able to pay off your bill?

Drew Macomber:
It got turned around instantly.

Brian Kelly:
So, how much did you do total in the coins? 100,000?

Drew Macomber:
Oh, yeah, for sure.

Brian Kelly:
So, you get all these points, and then you start reading FlyerTalk and blogs, and just getting wrapped up in this whole community, down the rabbit hole pretty quickly.

Drew Macomber:
Immediately, because I knew I wanted to travel, and actually, I wanted to travel full-time. My goal was to get married, take a year off, and by the time we were thinking about that, I had millions of miles. So, then we booked a one-way ticket and away we went.

Brian Kelly:
So, if your wife, then girlfriend, she was on the fence then, now with millions of points. She was going to have to say yes. I'm going to Bali-

Drew Macomber:
No, we-

Brian Kelly:
The points obsession is real. So, you get married, and then you lived in hotels for a while, right? So, you did do the travel?

Drew Macomber:
Mm-hmm (affirmative).

Brian Kelly:
Was it a full year? Were you gone longer than that?

Drew Macomber:
We were gone a lot longer than that, but originally, it was supposed to be a year. It was just, let's take off and travel. I started the blog, Travel is Free.

Brian Kelly:
What year was that?

Drew Macomber:
Early 2011, maybe 2010, but we started traveling mid-2011.

Brian Kelly:
If you have never been to his site, go to travelisfree.com. Even though he's now part of the TPG family of companies, he's still going to be writing in his free time for Travel is Free. Really interesting stuff, and we're looking to bring over some of the cool tools that he's created to the site and app. So, what did you learn? So, you went out on the road, you lived in hotels. How did you do it, living and working from the road and earning and redeeming points?

Drew Macomber:
Well, one year turned into five years, first of all.

Brian Kelly:
I didn't realize it was five years.

Drew Macomber:
Definitely, we very quickly transitioned to a points-hotels kind of strategy. So, I'll say this. I first discovered IHG promotions where it was kind of like the Accelerate promotion where you complete these tasks and you got, I don't remember, maybe 60,000 points. So, there was a cheap hotel, and I think in Bangkok or something, where we complete the promotion, both of us. We would alternate check-ins and we'd get-

Brian Kelly:
Mattress Run.

Drew Macomber:
One day in Vienna, we checked into almost every IHG hotel in Vienna, because there was a big sale and that was when they gave a free night for completing the promotion. I redeemed those free nights in Bora Bora, so it was well worth it.

Brian Kelly:
As you do. Earn cheap. Redeem expensive. For someone who wants to sell everything and just live as a nomad for three months, a year, what do you recommend, based on your experience? What was the easiest and cheapest place to live?

Drew Macomber:
Well, first of all, almost every country is cheaper than the U.S. If you go to anywhere in Asia-

Brian Kelly:
Especially nowadays with the U.S. dollar being pretty strong. So, do you recommend Southeast Asia? Is that-

Drew Macomber:
I love Southeast Asia. I love everywhere that's kind of different, but I really love Southeast Asia. I guess if you're working, you do need good internet, so places like Bangkok have that. Eastern Europe is the Asia of Europe where it's really cheap, they have really good internet and things like that.

Brian Kelly:
I haven't done too much of Eastern Europe, where have you been?

Drew Macomber:
Almost everywhere.

Brian Kelly:
Where do you like, I guess?

Drew Macomber:
Albania, I love Albania, and Bulgaria and Bosnia. Those are some of my favorites.

Brian Kelly:
Have you been to Slovakia?

Drew Macomber:
Yeah, only a little bit. I've been to Bratislava, but one time, I did a motorcycle trip down the Danube. So, that was cool.

Brian Kelly:
You got to write a book about these experiences. Final question. You're in coach on an airplane, three seats. Do you choose the window or the aisle?

Drew Macomber:
I like the window. I think it depends on-

Brian Kelly:
Yessss! Team window.

Drew Macomber:
If I feel like I have to get up for any reason, or the person on the inside is going to get up.

Brian Kelly:
You have to do the assessment.

Drew Macomber:
Yeah, I don't want to have to get up the whole time, but definitely, I'd much rather look out the window and see the landscape. Even if it's a long flight and you're going over the Arctic, it's still cool. I still enjoy it, looking out the window.

Brian Kelly:
Same. Drew Macomber, thanks so much for joining us. It's awesome to have you as a part of the TPG team, especially as we are about to change the way people use technology to maximize their loyalty. So, awesome having you and safe travels, my friend.

Drew Macomber:
Yeah, thank you very much.

Brian Kelly:
That's all for this episode of Talking Points. Thanks again to Drew Macomber. More details on the TPG app on our website and sneak peeks soon. We're so excited, it's going to be game- and life-changing for those of us who love to travel. If you liked this episode or if you hated it and want something else, let us know. Email podcast@thepointsguy.com. What topics do you want to hear more of and who do you want on the show? The sky is the limit, people: podcast@thepointsguy.com. Get in the know with the TPG daily newsletter. It's where you can get all your latest news, tips and limited offers delivered straight to your inbox every morning. Text: "Talking Points" to 33777 to subscribe. That's, "Talking Points" to 33777 to subscribe. This episode was produced by Margaret Kelley and Caroline Schagrin. Safe travels, y'all.