Unlocking Hidden Travel Perks | Dan Pascone with John Taylor Garner | Podcast #22

Posted on July 7, 2025 by Dan Pascone

Answer Box: TL;DR

You’re probably leaving serious travel value on the table. In this episode, Dan Pascone sits down with Odin founder & CEO John Taylor Garner to unpack how travel portals, loyalty programs, and credit card points actually work behind the scenes. John explains how Odin acts like a “Shopify for travel portals,” powering rewards platforms for banks, fintechs, and programs like Bilt so end users can turn scattered points into premium flights and hotel stays without becoming a full-time travel hacker. You’ll hear how dynamic award pricing, confusing rules, and poor tech cause people to hoard points or redeem them badly—and how better tools, smarter card strategy, and even simple retention-call scripts can unlock hidden perks and real-world trips, often at a fraction of the cash cost.

Key Takeaways

Odin is the “Shopify for travel portals.” Most banks and card issuers don’t build their own travel portals; they outsource to a small handful of large providers. Odin offers a modular, white-label platform so everyone from big banks to niche fintechs can launch highly customized travel and loyalty experiences without massive upfront spend.
Churn is the #1 problem for card issuers. Competition from niche cards and neobanks plus confusing redemption rules mean users often don’t unlock the value of their points. If a cardholder doesn’t understand or use a travel portal, they’re more likely to cancel the card—especially when annual fees climb.
Dynamic award pricing makes DIY “travel hacking” harder. Airlines and hotels have quietly moved from fixed award charts to opaque, dynamic pricing. That increases their profitability but makes it much harder for normal people to know what their points are worth or when they’re getting a good deal.
APIs + AI are reshaping how trips get booked. As airlines move toward NDC (New Distribution Capability) and API-based booking, platforms like Odin can plug directly into chatbots and AI tools to search, optimize, and book trips using both cash and points—something legacy portals struggle to do due to tech debt.
There are still powerful, practical hacks for individuals. John highlights strategies like using Aeroplan for Europe business-class redemptions, leveraging Marriott status with Amex transfers, and calling card issuers for “retention offers” right after an annual fee posts instead of canceling outright.

Key Moments

01:28 – What Odin actually is. John explains Odin as the “Shopify for travel portals,” powering white-label travel and loyalty platforms for banks, neobanks, and card issuers.
03:43 – Inside a flagship client partnership. How Odin powers key pieces of Bilt’s experience, from bonus-category logic to points transfer pricing and (soon) its travel portal.
05:35 – From volatility trader to travel-tech founder. John shares his background running a volatility trading book at Merrill Lynch and how his personal points hobby led to his first startup, Card Curator.
07:10 – Building a better way to use points. Why Card Curator started as a consumer super-app and how Odin emerged as a pure B2B/B2B2C infrastructure play.
09:20 – Why card issuers are bleeding customers. John breaks down how competition from niche cards and confusion around redemptions are hammering retention, and how Odin helps fix that.
11:46 – How end users actually benefit. Examples of how consumers indirectly access Odin through partners like Bilt, Monkey Miles, and FareDrop to get unbiased, optimal redemption recommendations.
15:25 – Case study: planning a points-heavy Italy trip. John walks Dan through a practical strategy using Aeroplan, Star Alliance airlines, and Marriott plus Amex transfers to fly business class and stay on points.
18:03 – The big headwinds in loyalty & travel. Why airlines and hotels are cutting value from loyalty programs, moving to dynamic award pricing, and how that impacts travelers.
20:29 – NDC, APIs, and AI’s impact on booking. How API-based airline content (NDC) positions newer platforms to plug into AI/chatbots, while legacy OTAs struggle with old infrastructure.
24:53 – A clever retention-offer hack. John shares his favorite timing and script for calling credit card companies after an annual fee hits to secure extra points or statement credits.
26:34 – A 5½-week Bali honeymoon on points. How John booked flights and hotels entirely on points and miles, paying cash only for food and drink.

Episode Summary

For many high-earning professionals, premium credit cards and airline status are just table stakes—but actually turning points and miles into outsized travel value is another story. In this episode, host Dan Pascone interviews John Taylor Garner, founder and CEO of Odin, a travel loyalty infrastructure company that quietly powers programs behind the scenes.

John explains how Odin functions as a “Shopify for travel portals,” giving banks, fintechs, and card issuers a modular, white-label platform to build modern travel and rewards experiences. Instead of each institution trying to negotiate directly with massive travel providers or build their own portal from scratch, Odin sits in the middle, tying together travel supply (via partners like Duffel) and loyalty logic (earn rates, transfer partners, redemption options) through APIs.

On the consumer side, Dan and John unpack why so many cardholders hoard points or redeem them for low-value options like gift cards. Airlines and hotels have moved to dynamic award pricing and opaque rules, making it harder for normal people to tell when a redemption is good. John walks through a concrete example—Dan’s hypothetical Italy trip—showing how to combine Amex Platinum points, Aeroplan for business-class flights, and Marriott Titanium Elite status into a high-end experience without paying high-end cash prices.

The conversation closes with a look at where the industry is heading: supplier-direct APIs (NDC), AI-powered trip planning, and why legacy portals struggle with tech debt. John also shares practical hacks, like asking for retention offers within 30 days of an annual fee posting and using signup bonuses strategically, underscoring that with the right tools and habits, your rewards can meaningfully enhance your lifestyle without blowing your financial plan.

Full Transcript

Dan Pascone: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Dan: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders to make smart, confident money decisions. Welcome to episode number 22 of the Making Sense of Your Money podcast.

Dan: I’m your host, Dan Pascone. I am the founder and CEO of Tailored Wealth. And each of our episodes features a trusted voice in the financial world—someone who works directly with high-level professionals to simplify the complex and turn strategy into action.

Dan: And today I’m excited to introduce our featured guest, and that is John Taylor Garner. John is the founder and CEO of Odin, and he and his team focus on, and have a great expertise in, the travel loyalty and reward space. So, this is a unique one for us and I’m excited to hear from John today. John, thanks so much for joining me on the Making Sense of Your Money podcast. Pumped to have you today.

John: Yeah, thank you. Excited to be here.

Dan: You bet, you bet. So, we’ve got a lot to cover. You certainly have a unique expertise and I’m really excited to kind of unpack that a little bit more and learn from you and what your firm is all about. But if you don’t mind, I know our audience would love to just hear a quick 90-second overview of what your business does—and maybe a little bit of background on how you got into it.

John: Yeah, sure. So, the way that we like to describe Odin is it’s the Shopify for travel portals and travel loyalty.

John: A lot of your listeners, and I’m sure a lot of your customers, probably have an ultra-premium credit card in their wallet—an Amex Platinum or Sapphire Reserve or Venture X, Capital One card. Those have travel portals associated with them: Amex Travel, Chase Travel, Capital One Travel.

John: The banks don’t build their own travel portals. They partner with other companies to build them because they’re not travel companies—they’re banks, right?

John: And so what we do is we actually are able to service those major banks, but also everyone else in the card-issuing space like a Bilt or a Ramp or a Brex, neobanks, credit unions, community banks, small guys, big guys, everywhere in between.

John: And there are tens of thousands of these institutions that are out there, and the vast majority of them don’t have travel portals. Why? Because they’re very expensive to set up, and they’re dominated by a few key players: Expedia, Booking, Hopper, and Ascenda—all multi-billion-dollar companies who can’t really service small players because they’re not going to get out of bed for anything less than, what, $10 million to start a contract.

John: And if you’re a community bank or credit union with 10,000 members or cardholders, it’s not worth the money to do that.

John: So that’s where we come in. We have a fully modularized, holistic, white-label travel portal that allows us to stand up a hyper-personalized experience for each one of our customers. So it’s tailored to their needs.

John: Or if you happen to have multiple customers—say you’re a card issuance company or you’re a major bank that has consumer cards and SMB cards and corporate cards and different tiers of cards within those cards—we can stand up a different version for each one of those types of customers, all with the same unified codebase. So the same team is running and managing all of them.

John: It cuts down on costs, makes things way more efficient, cuts down on implementation and also maintenance. It just makes it really easy to iterate, which the major players don’t allow for. So that’s really what we do in a nutshell.

Dan: Very, very cool. I’ve got a bunch of questions there. John, this is super interesting. So it seems like it’s got some variance to it, but tell us a little bit about your typical customers—like what makes them come to you, or how you find them—and then maybe give us a little bit of insight on them.

John: Yeah, for sure. So we’ll talk about a household name that a lot of people probably know: Bilt. They’re one of our first and one of our largest customers.

John: We started talking with them because they are now known—they’re synonymous—with a very high-quality rewards and loyalty program. You pay your rent on the card, you get points, you use the points for travel, right?

John: Pretty much anyone that has heard of Bilt knows that. We power their backend. So when you are linking your cards to your Bilt wallet and you see, “Hey, this card gives you 4x at restaurants,” that is one of our technology pieces—that’s one of our APIs.

John: When you are looking at the price in hotel points, transferring from Bilt to the Bilt partners like Marriott or Hyatt or Hilton, we display those pricings in the local hotel currency, how much that would cost in Bilt points to transfer, the facilitation of the transferring, and telling you when the optimal method is.

John: Now, not announced yet—people will see soon, I don’t know when that’s coming out—the previous provider of the Bilt travel portal is no longer going to be providing that.

Dan: Okay.

John: We will be. Again, not formally announced yet, so not naming any names, but that will be coming out very, very soon, which is quite exciting. And so that entire stack is powered by our APIs and our travel provider API.

John: So we ourselves are not a travel company, right? We don’t process bookings or issue tickets or any of that. That’s what our partner Duffel does. So Duffel handles—

Dan: You’re the SaaS platform, effectively.

John: Exactly. We’re the SaaS platform and Duffel plugs into us to provide the supply—the airlines, the hotels, and what have you. And so that’s what our customers allow us to build for them.

Dan: Super unique, super cool and interesting. How did you get into this, right? What prompted you to found this organization? How long have you been doing it for? And maybe tell us a little bit about your background and how you got started in this space.

John: Yeah. So it wasn’t straight into this. This isn’t an area of expertise that I had prior to my previous startup.

John: I used to be a volatility trader where I ran the international macro cross-asset volatility book at Merrill Lynch for about six years. It’s a very niche area, but the desk that I was on—the index desk—was the number one in the world for what we did. Pulled in about $350 million a year on average for a team of eight to nine people. So pretty serious revenues.

John: But I left that at the end of 2018 to start my first startup in the space, which was called Card Curator. It was a super app for credit cards—kind of like a NerdWallet or The Points Guy.

Dan: Sure.

John: And that was a B2C, direct-to-consumer play. The reason why I started that is it was a hobby of mine—opening credit cards, using points and miles to travel around the world in first class and business class and staying in five-star hotels. You know, not a bad hobby to have.

Dan: All right, so I don’t mean to cut you off, but let’s go there because I’ve got friends and colleagues like this. You sound like the guy that was always just maximizing and optimizing all of the credit card points, probably had it down to a science, probably built reports and spreadsheets on how to optimize all of that—and now the thought is, “Okay, let’s turn it into a tech company.”

John: Exactly.

Dan: Very cool. Very cool. All right. So when you started the firm, was the mission and the goal to set out to allow other consumers to travel as effectively, efficiently, and maybe lavishly as you did?

John: Yes, that was definitely when we started Card Curator—that was the idea, because that was straight-to-consumer. Odin was born from Card Curator, and Odin’s purely B2B and B2B2C, so it’s not a consumer play.

John: Hopefully, consumers are able to do that through our platform, and that is one of the benefits. But it’s much, much more than just that. The entire idea is to help give the user the optimal redemption for whatever they’re looking to do.

John: It could be first-class travel or business-class travel, but not everybody travels that way. There are plenty of people who, you know, take an RV and stay in motels or go to campgrounds, and they’re only flying because there’s a discounted economy fare or something.

John: So we cover the entire spectrum—from those ultra-premium cardholders, the wealthy and high earners, down to the average everyday American. We cover that entire spectrum.

Dan: Got it. Okay, makes a lot of sense. How did you get connected with—remind me the name of your partner that handles the travel obligations?

John: Duffel.

Dan: Duffel. How did you get connected with Duffel? Tell us a little bit about how that partnership began.

John: Yeah, so I know the founder and CEO, Steve. I’ve known him for quite some time—back to my Card Curator days. And there was nothing to do on the Card Curator end—there was no partnership or integration or anything. We just happened to get connected in the ecosystem of loyalty and travel.

John: It’s not a terribly large ecosystem. He’s based in London, I’m based in New York, but we got connected through a friend of a friend, met at a conference, and just from there, when I shut down Card Curator and started Odin, it took a little while—about a year and a half—before we were ready to do that integration with Duffel.

John: But three and a half, four years later after meeting him, we’ve now partnered and we’ve closed some really major names—a lot of which I cannot name here as of yet because they’re not publicly announced yet. But it’s been a very, very successful and great partnership.

Dan: Very cool. Very cool. All right, let’s talk a little bit about your customers. Let’s start with the B2B. Let’s talk about the businesses. Tell us a little bit about the challenges that the businesses that use Odin face and how you help them to overcome those.

John: Yeah. So the number one issue plaguing the card-issuing space today is churn. Their retention is awful, and it’s only going down—and this has been happening since COVID, really.

John: There are a variety of reasons. The first and most obvious one is competition. There are way more entrants in the space than ever before. The likes of Bilt and Brex and Ramp—they weren’t really around pre-COVID. And then there’s not just them, but the lookalikes.

John: There are credit cards—one of our customers, it’s a credit card for car payments. Another card; it’s a credit card for mortgages—another one of our customers. There’s a credit card for everything these days. And so they’re getting really specific because they’re tailoring specific needs and desires and wants of consumers and corporates and SMBs and what have you.

John: And this didn’t exist before. Everyone’s like, “Oh, what are my options? Amex, Chase, or Capital One”—basically the only options.

John: So you have a lot more competition. But then also there’s the not understanding of how to redeem loyalty. There’s confusion around this. That’s because the airlines and hotels during COVID changed their rules.

John: There’s no more award charts or published fares or how much a hotel costs. It’s dynamic. So you don’t know how much anything costs. And if you don’t know how much anything costs, then you’re not going to redeem and you’re not going to use your points or your miles, because you don’t understand it. It’s confusing.

John: So ultimately, you’re going to ask yourself, “Why am I paying a $500, $800 annual fee for something I don’t understand?” You’re going to cancel.

John: So it’s those two reasons that are the main factors. And we solve both of those reasons. We add a massive value-add, massive differentiating tool that allows our customers in the card-issuance space to offer a solution that is attractive for their cardholders, their customers, their users—to engage with their platform, to use their card, to drive spend on that card, to drive behavior, to redeem the points and miles that they’ve already earned.

John: And as you redeem, you use it more. And as you’re using the card more, you’re getting value out of it. You earn more. Your retention goes up over time.

John: And then we also allow them to incentivize the users by providing kickbacks like more points and miles, rewards, other things. And so it’s a great flywheel effect to fix this broken issue of losing customers.

Dan: Got it. Makes sense. All right, so let’s take that a level further. Now, you started to kind of explain this, but I want to unpack. A lot of our clients are sort of high-earning professionals that love to take advantage of points and travel perks and higher-end cards, as you mentioned.

Dan: Tell us a little bit about how the end user, how the consumer can benefit from your platform—albeit maybe in some cases indirectly.

John: Yeah, of course. So some of your members might have a Bilt card. They’re one of our largest customers here in the US.

John: We also power the likes of Monkey Miles and FareDrop, which are points-and-miles blogs that talk about redeeming points and miles and which credit cards to get—be it the Sapphire Reserve or Amex Platinum.

John: So they can access us through them. What we do for them, unlike the likes of Bilt which is tailored just to Bilt’s partners—so just their airline and hotel partners—the likes of Monkey Miles, for example, it’s everything. So all banks, all airlines, all hotels. It’s not limited to anything because they don’t have any relationships. So your customers and your listeners can access that, and that’s going to give them completely unbiased recommendations of how to spend their points and miles optimally.

John: How to fly to Tokyo in first class or stay in five-star hotels in the Maldives or the overwater bungalows, if that’s what they’re looking to do—that’s exactly what our platform allows for. And we can help them plan it and not just plan it but book it. It’s all done on the platform, it’s all native, and it takes all the guesswork, all the legwork, all the studying and research. You don’t have to do any of it; it’s all done for you.

Dan: And if that’s the case—because I know what you just mentioned is intriguing to me and I know it is for many of our listeners and users—do you recommend that folks like that have a dedicated relationship with an Amex or a Chase or a Marriott or whatever the case may be, or are they just sort of finding the opportunities as they come through your platform?

John: That’s a great question. So it depends on how quickly you’re looking to book said trip. Because generally, the easiest way to get points and miles is not actually flying and staying in hotels—it’s getting credit cards. The signup bonus is the fastest and easiest way to get them. But it does still take time. You need to hit the minimum spend, and then it takes a statement to close, and then they hit.

John: So it can take two to three months to get your signup bonus. So if you’re looking to do a trip in very short notice, it takes time to do that. Though I assume most of your customers already have existing relationships with a major bank, so they probably are sitting on a bunch of points and miles already.

John: The average person who has an ultra-premium card is sitting on over a million points and miles across the platforms. And this is because they know that there’s value there—they just don’t know how to extract it, which is actually good, because it’s better than redeeming it for like iPads or toasters or gift cards. That’s a horrible redemption.

Dan: Got it. Not a lot of value in redeeming for those items. Okay, got it.

John: Exactly. So they might already have a lot, but we can help them get more. Obviously, if they’re looking to plan six months out or a year out, we can help them plan that really awesome family vacation for four, you know, for a multi-week trip.

John: And that’s what we allow for. We can tell them exactly which cards to get, how to get the signup bonus, and then how to transfer from those bank programs into the airlines or hotels that they partner with to then make that booking.

John: But if they already have AA miles because they’re Exec Platinum on American, or they already have Marriott points because they’re Ambassador or Titanium Elite—that’s great. We factor in all existing programs that you have, be it an airline or hotel program or bank programs, and we factor that into the decisions in the recommendation system. So it’s tailored to each person.

Dan: Got it. All right, so I’m going to use my own personal situation. I want you to kind of coach me through this, and I think this will be a good example for our listeners.

Dan: So this is somewhat of a hypothetical, but a lot of it is accurate. I am Titanium Elite with Marriott and I have an Amex Platinum. I want to go to Italy next winter—or let’s call it February/March time frame. Six, eight months out, something like that.

Dan: What do you recommend? Guide me through that experience to get the most out of that trip based on what I already have.

John: Yeah, okay, great question. Generally, one of the easiest airlines to book for flights to continental Europe, particularly Italy, is going to be Aeroplan—so that’s Air Canada. Air Canada is a transfer partner of American Express.

John: They tend to run transfer bonuses. If not, it’s just going to be 1:1. But if there’s a bonus, which they do have, you can get like 1:1.2 or 1:1.35 sometimes, which is pretty nice. So if you can target that bonus, that’s great. We tell you when they are as well, so that’s in the system.

John: But Aeroplan is part of Star Alliance. The reason why I’m saying Aeroplan is going to be great for continental Europe is because Star Alliance dominates it. You have Lufthansa, you have Swiss Air. They just bought Air Italia or whatever the ITA Airways, I guess, rebrand is, so that’s part of Star Alliance now. So if you’re flying into there, connecting on, or flying direct, it’s going to be easy on Aeroplan.

John: So you can use that to book any one of those airlines that I just mentioned and then some—like there’s a dozen more that they own. They have quite a few. And that means that you have a better shot of getting business class.

John: Aeroplan also limits the taxes and fees that you have to pay. So you’re going to be looking at roughly 70,000 miles for that one-way business class, and the taxes and fees are going to be like about 110 Canadian, which is, what, like 75 bucks US?

Dan: Yep.

John: Not bad. So you’re doing that round-trip, I assume, for at least two people. So you’re looking at 140–280k miles. If you get a discount because Amex has a transfer bonus, you could do it for as little as like 220k Amex points.

John: And then for the hotels, there are tons of great Marriott hotels in Italy, depending on where you are. So you can stay at any of the Marriott hotels themselves or any of their third-party partners like the Design Hotels, which are like little independents.

John: Or if you’re redeeming Marriott points, if you’re looking to top up, Amex also transfers to Marriott. So if you’re short a few Marriott points for whatever hotel stay you’re looking to do, you can transfer from Amex to Marriott. And they also run transfer bonuses.

John: An example is Chase has a transfer bonus to Marriott right now at 60%. So one Chase point equals 1.6 Marriott points, which is pretty generous.

John: So you can just use your Amex points with your Marriott to book that full trip for the flights and hotels. You don’t need to go get any new credit cards or anything.

Dan: Very cool. Very cool. I learned something there for sure. All right. I appreciate that. Thanks for the guidance there.

Dan: All right, let’s switch gears a little bit. Let’s talk about the industry. What are the biggest factors that impact the travel perks industry? And tell us a little bit about what you and your firm do to kind of stay ahead of that.

John: Yeah. So the biggest impact that’s afflicting them today is cost cutting on the airlines and hotels, because they are concerned that their loyalty programs are costing them too much money.

John: Now, this is short-sighted, to say the least, because their loyalty programs are the single most profitable part of all their businesses, period. So cutting cost there, I think, is awfully short-sighted—but it is what they’re doing.

John: What they’re doing is the likes of, we discussed earlier, dynamic loyalty pricing. So getting rid of award charts, getting rid of transparency so that they can obfuscate what they’re doing to increase prices without getting negative ramifications.

John: Now, obviously, there’s still blowback. We’ve seen this in the news all the time—back in, what was it, 2023 October when Delta got in a world of hurt for all the changes that they made to SkyMiles program and their credit cards and status and all that. ITA Airways is going through that right now. There’s been a multi-month—since April, I think—real slog. People are unhappy about it.

John: And so what we are doing to stay ahead of this is our systems are natural-language-processing-based. So they are a unique type of AI to aggregate all this loyalty pricing for the airlines and hotels. Anytime they’re making changes, we are staying dynamic and are able to pull in those changes, those updates to rules and policies, the updates to pricing—whatever it is—we are able to still see that and push that information on to the user.

John: And then as they are making their systems more complicated and difficult to use, the user is being negatively impacted. That drives the need for what we do even more, because now the user is even more confused and doesn’t know what’s going on. So then they come to us to help solve that.

John: So inherently it’s kind of a double-edged sword, if you will. We are trying to make the best of it and make it as useful for the consumer as possible. But it’s not a long-term sustainable path. Ultimately, the airlines and hotels could strangle their golden goose. If you keep cutting away, then there’s not going to be anything left.

Dan: Yeah. Sure, sure. And where do you see the industry going moving forward? Obviously these are trends that have been arising as of late. Where do you see the industry going? And then the second part of that question is: How is technology like AI impacting this?

John: Yeah. Great question. So this is a very cyclical industry. So the cuts—they happen all the time, every, call it, 5 to 10 years. And that’s because travel is booming right now, and so the airlines and hotels are feeling confident that they can cut costs to further increase profits.

John: Now, once travel starts to slump—because it eventually will; travel does slump—then they’re going to start giving a bunch of perks and benefits back to people to try and incentivize them to travel again. So it just goes in cycles. This is what happens.

John: But the longer-term cycle in terms of where things are going and how they’re looking—AI is definitely a big, big concern. But the airlines and hotels are actually pretty well-positioned for it. Why? Because they are looking at expanding ways to drive supplier-direct bookings—i.e., booking direct with airlines, hotels, not going through third parties like Expedia or Booking.

John: This, for airlines, is called NDC content versus the traditional third parties—GDS, which is global distribution systems. That’s what Expedia and Booking run on. There are companies like Sabre, Amadeus, which you’ve probably heard of—technology companies that have been around since the ’70s, basically.

Dan: Yep.

John: So what is NDC? NDC allows booking via API. Why are APIs so critical in the AI phase? Well, you can plug an API into a chatbot. You can’t plug Expedia into a chatbot. You can’t plug Booking into a chatbot. You can’t plug AmericanAirlines.com into a chatbot. You can plug an API.

John: So any of the airlines—which we have natively in our platform because of Duffel. So we have supplier-direct content via APIs. And so we can put our entire system into a chatbot and have somebody book purely through that, or we can plug it all into ChatGPT or whatever your favorite chatbot is.

John: It doesn’t matter; we can facilitate all that because we are using the latest technology for that. This is something that the Expedias and Bookings of the world are struggling massively with because they have very dirty, outdated data systems and data lakes and databases and whatever. And they’ve spent billions and billions of dollars trying to clean it up in a way that’s actually readable and usable.

John: And there’s just too much tech debt—which is why what the airlines have done, and hotels are working on this too, is so smart: don’t try to fix all that other crap, just do something new. And that’s what NDC is. It’s an entirely new booking system. So you’re starting from scratch, which is kind of the best thing to do with AI, because cleaning up old systems, you’re just going to run in circles and just waste a whole bunch of money and get nowhere.

Dan: Got it. Makes a lot of sense. Really, really good breakdown there.

Dan: All right, we’re going to switch gears completely now and learn a little bit about you, John. So we’re going to enter into what we call the lightning round. So our guests never know about this ahead of time.

Dan: All I want you to do is give me the first thought that comes to your mind. Could be a one-word answer, could be a long, drawn-out thought—whatever makes sense for that question. You ready to go?

John: Yeah, let’s go.

Dan: All right, let’s do it. Coffee or tea?

John: Coffee.

Dan: One meal for the rest of your life?

John: Branzino with grilled vegetables.

Dan: All right, sounds good. I like it, I like it. This will be a good one for you. One tool or piece of technology—could be hardware or software—other than your computer or your phone that you can’t live without?

John: Apple TV.

Dan: Okay, I love it, love it. Got an Apple TV in my office right here.

Dan: Favorite quote or phrase about money or success?

John: “It’s about the journey, not the destination.” I know that’s not directly about money, but if you set goals and you achieve them, once you achieve them, you’re like, “Now what?” You need to enjoy the process along the way.

Dan: That’s right. I couldn’t agree more. Couldn’t agree more.

Dan: Do you have a favorite book on finance or business?

John: Definitely not related to what I do, but I have quite a few of them just from an interest standpoint. So Freakonomics I always thoroughly enjoyed; Barbarians at the Gate—it’s a classic; Liar’s Poker. I’m not into the self-help books or the entrepreneurship books, those kinds of things, but I’ve always enjoyed the Malcolm Gladwells and the sort of statistics-y, economics side of things.

Dan: Makes sense based on what you do and what you’ve built.

Dan: Do you have a personal hack you can share with our audience?

John: Outside of the travel hacks?

Dan: Yeah, you kind of already gave us that already, I guess.

John: Yes, I definitely have one. So the Chase Sapphire Reserve cards were just revamped. The rate has gone up from $550 to like $800 a year or something—a massive, massive jump.

John: So if you’re thinking about canceling your Chase credit card, wait until the annual fee hits on your card. Then you can call up Chase—and this applies to any credit card, by the way—within 30 days. It has to be within 30 days of the annual fee hitting your account. Call them up and ask for a retention offer. What are they going to give you so that you keep the card?

John: It might be a pretty decent offer. It could be hundreds of dollars, could be tens of thousands of points, or some combination thereof.

Dan: So just tell them you’re going to cancel essentially.

John: Exactly. But don’t say, “I want to cancel.” Say, “I’m thinking about canceling my card. What retention offer can you give me?” Because if you say, “I want to cancel,” they’re just going to cancel it. So you have to play this game.

John: If they give you something great, then keep the card, and you now just earned a bunch of free money and free points. If they don’t give you anything good, then you can still cancel the card and they will refund you your annual fee. They can do that up to 30 days after it hits. But doing it at this moment in time is the optimal time to get that retention offer because they are legally required to refund you, and they don’t want to refund that money.

Dan: Got it. Okay. Timing is everything on that one. All right, I like it.

Dan: What’s one financial milestone—either personally or business-wise—that you’re working towards?

John: We are working towards cash-flow positivity at Odin. We are getting there. We are on track to clear it by year-end—knock on wood. So that’s the real goal for the year.

Dan: Awesome. Wish you the best on that journey, and I’m confident you’ll get there.

Dan: What’s one bucket list item that you’ve already accomplished?

John: I guess I’ll pick my honeymoon. I was recently there over Christmas and New Year’s, so about six months ago. We stayed in Bali, went all over the island, but was there for a full five and a half weeks.

John: And I did the entire thing on points and miles—all flights, all hotels. The only thing I used cash for was food and drink. So I was pretty proud of that.

Dan: Well, congratulations on that, and good to hear you’re practicing what you preach. I love it.

Dan: All right, last one. If you could give one piece of advice to your younger self, what would it be?

John: So, it took me a while to learn this one. From my days at Merrill, it’s way more important who you work with than what you’re doing. I loved what I was doing over there. I was a weird kid—I always wanted to be a volatility trader since I read Market Wizards (another book for you), and I was like, “I want to be a prop trader.”

John: Dodd-Frank came around; prop trading was made illegal. What’s the next best thing? Volatility trading. I loved it for six years. Ultimately, I ended up trading the exact book I wanted: international macro cross-asset volatility. But I just wasn’t loving the people I was doing it with.

John: And so after six years, I finally realized that who you’re working with matters way more than anything else.

Dan: That’s a powerful one. That’s the first we’ve heard on that—the power of who. Spot on.

Dan: All right, excellent. So John, if our listeners want to connect with you, with Odin, collaborate, work with you, learn more—what’s the best way to reach out to you or follow?

John: Feel free to email me at jtg@odin.com—that’s J-T-G, and then Garner, G-A-R-N-E-R, at odin.com. You can reach out on our website, www.odin.com—O-D-Y-N is how we spell Odin. Or you can connect with me on LinkedIn, follow us on our LinkedIn page. We’re all over it.

John: So yeah, we are very, very responsive and always happy to partner.

Dan: Awesome. Very good stuff. Thanks so much for sharing your time and your insights today. I know I learned a lot. I know our listeners will, and this is certainly a fun category to learn and become very fluent in.

Dan: So thanks for sharing the time and the insights. That’s it for the episode. As always, keep your strategy sharp, your goals clear, and your money working as hard as you do. Cheers to everybody.

Resources & Citations

Air Canada Aeroplan Program. Official information on earning and redeeming Aeroplan points, partner airlines, and award charts.
Star Alliance. Overview of Star Alliance member airlines, routes, and benefits for international travel.
Marriott Bonvoy Elite Status Benefits. Details on Titanium Elite and other status tiers, including perks that can enhance points-based hotel stays.
Basics of Airline & Hotel Loyalty Economics. Educational resources explaining why loyalty programs are often the most profitable part of travel companies.
IATA – New Distribution Capability (NDC). Industry background on API-based airline content and how it differs from legacy GDS systems.
Guides to Credit Card Retention Offers. Consumer-focused articles outlining how and when to ask issuers for bonus points or credits when annual fees hit.

FAQs

How does a platform like Odin actually help me as a traveler?

Odin sits behind the scenes powering travel portals and loyalty tools for banks, fintechs, and rewards programs. When you see smarter suggestions about which points to use, get clear pricing in hotel or airline currencies, or have an integrated way to transfer and redeem points across partners, there’s a good chance that infrastructure is built on something like Odin. You typically access it indirectly through your card issuer’s portal or through partners like Bilt, Monkey Miles, or FareDrop.

Is it still worth collecting airline and hotel points with all the dynamic pricing and devaluations?

Yes—but how you use them matters more than ever. Dynamic award pricing makes it harder to know what a “good” redemption looks like, which is why tools that benchmark value and compare options are becoming essential. For many high-earning professionals, points are still one of the most tax-efficient ways to upgrade travel experiences, especially for premium cabins and high-end hotels, as long as you avoid low-value redemptions like gift cards or merchandise.

Should I focus on one bank (like Amex or Chase) or one airline/hotel program?

There’s no one-size-fits-all answer. Many people benefit from having a primary transferable-points ecosystem (e.g., Amex, Chase, or Capital One) plus one or two core airline/hotel relationships that match their actual travel patterns. The key is flexibility: transferable points can be directed to whichever partner offers the best value for a specific trip, which is exactly where optimization tools and APIs shine.

What’s the big deal about NDC and APIs in the travel world?

NDC (New Distribution Capability) is an industry-standard that lets airlines sell flights and ancillaries through modern APIs instead of legacy systems. For travelers, this means newer platforms can search, price, and book flights more intelligently—and in the future, AI-powered agents will likely be able to plan and book trips across multiple airlines and hotels in a single conversation, using both cash and points.

How do I use John’s retention-offer hack with my own credit cards?

When your annual fee posts on a card (especially a premium one), note the date. Within about 30 days, call the issuer and say something like, “I’m thinking about canceling this card because of the annual fee—are there any retention offers to keep me as a customer?” If the offer is strong (points, statement credit, or both), great—you can keep the card and enjoy the perks. If it’s weak or nonexistent, you can still downgrade or cancel and typically get the fee refunded within that window.

Where should I start if I want to plan a big trip mostly on points?

Start by listing the points and miles you already have across banks and travel programs. Then choose a realistic time frame (often 6–12 months out), and a target region or trip (e.g., Italy, Japan, or a beach destination). From there, you can look at which alliances and hotel brands serve that destination and plan backwards: earn or transfer into those programs, watch for transfer bonuses, and use a tool or advisor to compare cash vs. points options for flights and hotels.

Disclaimer

This episode and page are for educational and informational purposes only and do not constitute financial, tax, legal, or travel advice. Any credit card products, loyalty programs, or companies mentioned are for illustrative purposes only and are not endorsements or recommendations. Card terms, loyalty program rules, and redemption values change frequently—always review current terms and consult your own financial advisor before making decisions related to credit cards, points, miles, or large travel purchases.

Next Steps

If you’re a high-earning professional or executive, your points and miles are part of your total compensation picture. Take 20–30 minutes this week to inventory your cards, points balances, and status levels, then identify one future trip you’d like to fund primarily with rewards.

From there, you can start aligning your card strategy, signup bonuses, and transfer partners with that goal—or, if you’d like more help integrating rewards into your broader wealth plan, explore more episodes and resources at Making Sense of Your Money, or learn how Tailored Wealth partners with equity-rich professionals and leaders at yourtailoredwealth.com.