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Today we have an exceptional episode featuring Eli Facenda, 
an expert in credit card points optimization and luxury travel hacking. Known as “The Travel Guy,” Eli has mastered the art of turning everyday credit card spending into luxurious travel experiences. His journey began in 2015 when he combined his passion for entrepreneurship with a knack for creating memorable trips, ultimately leading him to establish a successful travel hacking business.
In this fascinating episode, Eli shares how he helps entrepreneurs and business owners leverage their credit card spending to unlock incredible travel rewards. He discusses how the right credit card strategies can transform points into free first-class flights and five-star hotel stays, providing substantial value without the high price tag.
One of the key discussions is about maximizing value from credit card points through strategic transfers and reward programs, illustrating how savvy use of points can lead to unforgettable travel experiences. Eli also opens up about his role in designing custom travel solutions that cater to the specific needs of business owners.
Moreover, the episode explores Eli’s initiatives in organizing high-end travel events, such as his captivating ski trips, offering listeners a glimpse into the unparalleled experiences that one can achieve through proper points optimization.
In This Episode
- Eli’s journey from budding entrepreneur to travel hacking expert
- Strategies to maximize credit card points for luxury travel
- Tips on how flexibility and planning enhance travel value
- Insights into crafting personalized travel experiences and events
Eli, welcome to the show.
Dave, thanks for having me, man. Excited to be here.
Yeah, 100%. I know the audience is really gonna enjoy this one, as am I. One of the things I love to do is creative financing and financial hacking. And you bring that to us through the realm of luxury travel, experiential travel, which I think is really amazing because I think, especially as entrepreneurs or freedom seekers, that’s what it’s all about.
Right? We’re trying to use our financial capital to actually create amazing experiences in our life. We’re trying to travel to different destinations. And we want to do that in a way that really respects our time, right? Because time is your greatest asset. And so if you’re flying at the back of the bus, in economy, or you’re going through all these different transfers in different countries, I’ve now traveled to over 50 countries, I’ve been to six continents, and I can assure you, I’ve been through it all.
And it can be really demoralizing as well as frustrating to do that and wreck that experience. So really excited to have you on today and hear your wisdom about travel hacking, how we can do that, and take advantage of all of these cool things that there are that you’ve actually uncovered.
So why don’t we start with your story a little bit, Eli, and tell us how you became an entrepreneur and then eventually got into this kind of travel hacking business.
Mm-hmm.
Yeah, they coincided at really the same time. So I’ll take you back to 2015. I was graduating from college, and I had a finance degree at a school near New York City. Naturally, everyone goes to Wall Street, but I just never felt that pull. I was like, I’m more of an entrepreneur. I want to build a business. And I felt more excited about building a business than just going to the Wall Street world, managing money, and doing investment banking or whatever it was going to be.
It turned out that my former high school baseball coach had started this international tour company, and I ended up becoming the first employee. What we did there was take youth sports teams and families on international tours all over the world. What was amazing about it is I had a lot of freedom. My first assignment actually was, “Hey, you got like 2,500 bucks, go over to Europe for three weeks, make as many connections as you can.” So here I am, 23 years old, feeling on fire about what I get to do.
But I forgot to ask one big question before I was like, “Let’s do this,” which was, “How much are we gonna make?” I just took the job because I loved it and basically had no money. I really wanted to travel with a lot of my friends who were making a lot more money. So here I am with this problem: I want travel, I want these bucket list experiences, but I don’t have money. So it’s either I get what I want, or I have to find a smarter strategy.
Between that and the value that these credit card points could add to that company, there was this intersection that led me to be like, “If I can figure this out, this is going to kill a lot of birds with one stone. I’ll get the trips I want. I’ll save the company money, which will add a lot of value.” So it just started as this kind of side little exploration. It turned into a real hobby and then a passion. And then ultimately that passion turned into a full obsession and then a side business.
I launched my own company in this space about five years ago because there were so many business owners that needed help. I realized I could really serve them. I started as an entrepreneur on the business side. I was basically a number two and got equity in that company. Then I realized the need in the market. I had solved my own problem, and I was like, “I can help all these people too.” So I started a little side business, but then social media happened, all this stuff, and it really exploded and took on a life of its own.
I was like, “I’m going all in on this thing.” That was about four years ago now. It’s been a fun ride, and a combination of things that I love, things I’m passionate about, and things that really add value to others has always kind of been the intersection of a business for me.
Yeah, awesome. So why don’t you tell us a little bit about the company now? How does it work? And who are your typical clients? What’s the process?
Yeah, I’ll start with the typical client. Typically, it’s a business owner that’s spending a decent amount of money every month, and our threshold is like $15k a month between personal cards and business cards. Now, the reason that’s important is because that’s what’s going to generate the points for us and help them leverage for trips. Okay, so that’s kind of criteria number one.
Then they also have to have a desire for bucket list travel. We can help get upgrades on domestic travel, better lounges, and hotel suite upgrades. That’s great, and I don’t want to downplay that—there’s a lot to be saved and optimized there. But that’s kind of a cherry on top. For us, the real driver of the business is when someone saves $30,000, $40,000, $50,000, or even $100,000 on a bucket list trip to Italy for two weeks. They take their grandparents and the grandkids, they all get business class, and they get to go first class.
That’s who we’re really trying to serve: the entrepreneur who wants luxury travel, wants the perks, but doesn’t want to spend the time figuring out all these points strategies, points arbitrage, where to transfer the points, and which cards they need. They also don’t want to overpay for something when there’s a much better way to get the same thing they’re already going to be spending money on.
So that’s really who we help. There are two main elements of the business. First, there’s optimizing the cards—getting the right cards and the right expenses so that you earn the most points and get the best status for upgrades. Then there’s using the points effectively. That means taking the points you currently have or continue to earn and getting double the value, triple the value, four, five, even 10x the value.
Or, another way of saying that is, you get the same flight to Italy. Let’s say it’s $5,000. Instead of paying 500,000 points to Amex Travel, you can get it for 60,000 points, 70,000 points, or 80,000 points—a fraction of what it would normally cost. So, we help entrepreneurs who want to travel optimize their credit card spend and use their points for their dream trips.
Yeah. Well, that so resonates for me because I love to travel to Italy, number one. Any chance we can go internationally, it’s so enriching to me. It’s really been such an amazing experience. I think a lot of people, if they don’t travel internationally, are really missing out, right? Learning about cultures, making new connections—it’s incredible.
I have some friends over there that I consider some of my best friends, and it’s just been an amazing experience. We’ve been able to bring our kids over there, and they’ve learned so much through that experience. It’s really great. But I know, in terms of what really hits home, what you’re talking about is just that frustration.
I mean, I’m definitely spending that and a lot more on credit cards because, let’s face it, we all do these days, right? It’s just so much easier to use your card and pay it off later. Maybe you’ve got airline points or something, but trying to figure out the system and how it works—you need a master’s degree and a lot of time, right? So yeah, okay.
Yeah. Well, we tend to compare it to accounting. As a business owner, you probably want to be able to look at your profit and loss and understand what’s happening, right? And your cash flow statements and stuff like that. But you don’t want to be doing your books.
You don’t want to be reading the IRS code, keeping up with all the changes the government makes, and figuring out every legal loophole on your own. That’s why you have a CPA. At a certain level, time becomes really valuable. That doesn’t mean you shouldn’t file your taxes effectively and play the tax game—you should. It just means maybe you shouldn’t be the one doing it.
That’s kind of the same thing we help with here—allowing people to save their time and still get the benefits. Yeah, you’re nailing it.
Yeah, okay. Now, awesome. So what are some of the strategies that you actually employ to do that?
Yeah, so I’ll kind of chunk it into three buckets, and this just makes it simple to understand the game. There are a lot of different tactics, like 100 little nuggets and strategies, so I like to give a broad overview. Here’s how to think about this, and then I’ll talk about the strategies within each bucket.
The first bucket is to maximize your points earnings. This means having the right credit cards for you because they’re different for everyone, depending on your expenses. For example, let’s say someone spends a lot on advertising for their business. If they have the Amex Business Platinum card, they’ll earn one point per dollar. But if they have the Amex Business Gold card, they’ll earn four points per dollar.
One card difference for someone spending $10,000 a month on ads could result in hundreds of thousands of points annually. That’s $30,000 to $50,000 a year in travel value—just from changing one credit card for one category of spend. So, we need to get the right credit cards aligned with the right expenses.
Part of this is also making sure you earn the right points because they’re all worth different amounts. For instance, if I offered you $100 US dollars or 110 Mexican pesos, you’d obviously choose the dollars because they’re worth more, even if it’s a smaller number. The same principle applies with points. If you don’t know their value, you could end up earning tons of Delta miles or Hilton points that look like a big number but are worth much less than Amex or Chase points.
The second bucket is to maximize the value of the points, and this is done through transferring them. This is kind of the meat and potatoes of it. Basically, you convert your points from a bank program into an airline or hotel loyalty program. There’s a way to gamify this and find arbitrage opportunities because airlines are part of alliances, and some of these airlines partner with banks.
For example, I’m flying to Japan for a ski trip, and we’re going through Taipei on a new luxury airline called Starlux. I used Alaska Airlines points—converted from American Express—to book Starlux. I didn’t book directly with Starlux; instead, I used these partnerships to maximize the value. That’s the essence of it.
The third bucket is to upgrade and optimize your travel. This involves unlocking status, maximizing suite night certificates, getting TSA PreCheck and Clear, ensuring access to the best lounges, and getting perks like free bags, free first-class upgrades, early check-in, and late check-out. These things make travel more comfortable, seamless, and easy. Usually, these benefits come from having the right cards and achieving status.
So, those are the three buckets: maximize points earnings with the right cards, maximize the value of the points through strategic transfers, and maximize your upgrades.
Yeah, no, that makes sense. That really hits a pain point I have. For example, let’s say we want to fly to Italy. There are only certain airlines I can actually take from here. If I’ve been using the points system of another airline that doesn’t fly from here, it feels like, “What’s it worth?” Or the same thing with these lounges.
You join one lounge, and then you go travel somewhere, and I’m in Phoenix and like, “Hey, they don’t have a lounge here.” Right? So do you guys have all of that figured out? Because it seems like there’s just not enough flexibility in terms of lounges. Right?
Right. Yeah.
Yeah. So, like, when we work with someone, we’ll look at—we kind of create their travel DNA. We do a pretty extensive intake. We’re looking at what matters to you because what matters to you and to me may be very different when it comes to travel, our home airport, the amount we spend on different things. So that’s going to create a different plan, which will unlock different perks.
For some people, they don’t care about lounges. Like to me, I love a lounge. It’s my favorite thing. If I’m flying, I get four hours, I’ll show up early to airports on certain flights because I want to hang in the lounge for three hours. There are some that have a pool with a tarmac view. It’s crazy.
So, we always are looking at those specific nuances and making sure that it’s really custom to you. Another one— a lot of people are traveling more domestically for conferences and business events, and they’re like, “Hey, I do one trip a year to Europe or whatever. I want that. But man, if you can help me save on the hotel suite upgrades when I have business travel, because I’m paying a grand a night for these upgrades and I’d love to get these suites for free,” that’s an easy, low-hanging fruit opportunity. That may not be relevant for you, but super relevant for them.
So, it really is kind of a custom thing with that. But all those things are possible. Even to your point, where you’re talking about the airlines and the options that you have when you fly to Europe, that’s going to be custom to you too because everyone has different parameters.
Some people will say, “I only fly nonstop, non-negotiable.” And others will say, “Well, if it’s a great experience and I need to do a one-stop, I’ll do an hour hop to Atlanta or to Charlotte or maybe to New York to get the best business or first-class flight over to Italy.”
So, it’s preferential. When we’re doing stuff, we’re custom fitting it to the client because everyone has a different kind of taste.
Yeah, makes sense. And do you guys do any work for private flights? Because I know a lot of private charters also have a couple of seats that you can pick up at fractional cost. But the same thing—it’s trying to understand the system and make it work.
Yeah, unfortunately, there’s no real overlap with points and private travel. The closest thing would be JSX, JetSuiteX, which is like semi-private. Basically, the only benefit you get there is you earn JetBlue miles when you fly on them, but you can’t really use the points. There’s not a lot to gamify there.
That’s a great point I’ll just hit on real quick because people ask, “How far does this points game go? What can I use these for?” I’m happy to share good versus bad usages of these points, but overall, you’re looking for business and first-class international flights as your number one value driver. Luxury hotels are number two.
If you want to use points for rental cars, Airbnbs, private flying, or trains, technically, you can do it through the bank’s travel site, but it’s just worse value than what the points should be worth. So I don’t advise it. But if that’s the only thing someone’s going to do and the only way to use their points, they still can. Typically, though, I don’t recommend it.
Got it. Yeah, I was going to ask that too. Do you guys have any, maybe it’s partnerships or any other capabilities around travel itineraries once you get to destinations?
Yeah, we integrate with local travel agent partners that will help with that kind of stuff. For those that want it—you want the black car pickup, you want restaurants mapped out, you want tours, activities, and excursions—that stuff, our team will help advise on natively within our own services.
But for people who really want the “I just want the white glove” experience, we have partners that will handle that stuff on the ground. We actually have a client right now, a big real estate investor, who’s doing a family trip. They’re going to Hawaii, Japan, Sydney, and New Zealand for six weeks—a family of four, business and first class. They want the whole thing. They’re like, “We want bungee jumping here. We want to stay at The Peninsula here.”
Some of that stuff is not a points-related thing. For us, when we’re thinking about our business model, it’s about what the client wants. They want an easeful experience. So we always try to provide as many options as we can to make that happen, from card planning to using points to on-the-ground access.
Yeah, no, that really makes sense because if you can get on-the-ground access—one of the things I’ve struggled with is, you know, most tour operators, you talk about Italy, for instance, and people say, “Well, we’re going to Rome, Florence, and Venice.”
You talk about some small town in Liguria, and they have absolutely no idea. But there’s unbelievable experiences that are so authentic, like going to an olive vineyard somewhere or an orchard and just having that experience that’s totally local. No one would really know about it because it’s kind of a local thing.
Yeah, totally. I mean, fortunate for me, because I have that background with a tour company. What was really cool about that is we were taking sports teams to international countries. So we did a lot of Italy. We’d actually bring a lot of baseball teams to Italy.
What was cool about it is because you’re playing local teams in sports, it’s not like all the big teams are in Rome, right? In fact, one of the hotspots of baseball in Europe randomly is in Nettuno, Italy, which is like an hour and a half south of Rome.
This is a really cool historical spot because it’s where the US military, when they were stationed over in Europe for World War II, spent a lot of time. So baseball really picked up. It’s this beautiful small beach town, and one of, if not the biggest, American military cemeteries in Europe is there. You can go see these incredible grounds. It’s like this small town where you can get an entire pizza the size of the table for like four euros. Just an unbelievable experience.
Yeah.
No one, I’ve never heard anyone mention Nettuno who’s not Italian. So if you do go off the beaten path, that’s totally where the juice of the experience is to me.
I always say, “Hey, if you’re going for the first time, maybe do the starter kit.” Do the sampler—see Tuscany, Rome, and Northern Italy—and kind of get a flavor for what you like. But you’ve got to go deeper after that. To your point, there’s so much out there, and it’s just such a fun adventure every time.
Yeah, to that end, do you guys curate experiences or anything?
We haven’t done a lot of the experience side. Our lane is primarily getting the best value for the points and integrating that with the booking side for those that want it.
For individual experiences, what we’ve done is partnered with people who specialize in that. We actually have a really cool group your audience may love if they don’t know about it. We’ve partnered a lot with a group called Insider Expeditions.
They just did a sailing on the Ritz-Carlton yacht for three days off the coast of Portugal with high-level entrepreneurs, investors, and philanthropists. They then sail across the Atlantic and do all sorts of cruises, like luxury high-end trips to Antarctica or Greenland through the Arctic Circle.
We’ll partner with groups like that. Another group we work with is Maverick, which does really high-end things like Necker Island with Richard Branson. There’s a percentage of our clientele that loves this kind of stuff.
We help facilitate the best way to get there. For example, we’ll say, “Here’s the trip in Portugal. If you want to jump on this itinerary, sign up there and let us know. We’ll help you with the flights.” That’s how we integrate—giving them the best access while staying focused in our lane.
Yeah, no, that makes a lot of sense. Some of the experiences are just amazing that I’ve seen. I’ve literally seen like the whole James Bond experience where, you know, you can drive one of the old Aston Martins. It starts out in the UK. You get one of the vodka martinis that Bond used to hang out with. And then you kind of travel across Montenegro and some other great places. But yeah, these are some epic things.
So cool, epic.
I highly recommend to folks to just really start thinking about some experiences like this that you can create in life. Because when you think about it, when you’re 90, when you’re 100, these are the things that you’re going to remember. It isn’t going to be the size of your bank account. It’s these memorable experiences with your family, your friends, your colleagues that you created. So it’s really fantastic.
How about from a corporate standpoint? Do you guys help with this also? Let’s say we’re hosting our Mastermind event at the Ritz here coming up. Do you guys help set those kinds of things up too?
We don’t really help specifically with that. We’ll help make sure that when you’re planning, it’s optimized from a points-earning standpoint. So you’re at the Ritz, right? You definitely want to have a Marriott card for that one because you put that spend on that card.
If you unlock status, you’re going from earning, you know, maybe one, two, or three points per dollar on certain cards to 11, 15, or 20 points per dollar. So you throw an event like that, and all of a sudden, after the event, you’re sitting on a mountain of points.
We’d help with that. And then there are certain VIPs and stuff like that, that you’re flying in to maybe speak—like my Japan trip. I have two speakers that are coming to present. What I’ll do is I’ll often use points to bring them in. I can write it off for the event as an event cost, but when I can use points for that kind of thing, I’ll sometimes opt for that.
So that’s more of what you would want to look at this from—a vantage point of card optimization and points optimization. We don’t go into the travel planning or event planning side of that. That’s a lot of scope for us, but yeah, it’s more focused on how to leverage the point side.
Yeah, got it. Tell us about your Japan trip.
Yeah, so, I mean, you were kind of hitting the nail on the head. For me, this perspective came from a very personal place. When I was growing up, I had a near-death experience that really shaped how I think. At a young age, I started asking bigger questions: What are we doing here? What do I want my life to be about? What’s important?
For me, it always came back to meaningful experiences with people I care about—doing bucket list things. These trips and moments that make you come alive. I’ve found that they are consistently the most fulfilling and memorable parts of my life.
I’ve always thought about this idea of “rocking chair philosophy.” I picture myself as 90-year-old Eli and ask: What would he want me to do in this moment? The goal is to make sure that guy has no regrets. That mindset has led me to create these experiences.
I started combining things I already love—like skiing—with opportunities for growth and connection. I’m an entrepreneur, so naturally, I want to grow my business too. I developed this formula. Honestly, though, the most impactful conversations often happen on the ski lift. It’s this perfect blend of fun, relaxation, and deeper connection outside of a traditional business setting.
The first event I ran was a huge success. Afterward, people who regularly attend masterminds told me it was one of the best experiences they’d ever had. They asked if I could do more, and I thought, Why not?
The next year, we went to Chamonix, France. That trip was incredible. We flew into Milan on an Emirates A380 flight from JFK to Milan. That flight is wild—it’s a double-decker with an in-flight bar, showers in first class, Dom Perignon, caviar—the works. Out-of-pocket, it would’ve cost $20,000 for two people, but I used just 200,000 points and $200. That’s nothing compared to the experience.
For that trip, we had 45 people in the group, and 25 of them flew business class together. Picture this: 10 minutes after takeoff, the seatbelt sign goes off, and 20 guys stand up to head to the in-flight bar for a cocktail party in the sky.
It’s always been about creating these once-in-a-lifetime, cherished memories. That’s the essence of these trips—whether it’s the Japan trip or the ski trips. That’s why I create them.
If you can start thinking bigger about travel, it’s not just a vacation-it’s an investment in experiences that last a lifetime.
Yeah, totally love it. Really good.
What about from a productivity standpoint? You know, personal productivity. We’re big into professional development and biohacking here. As a big traveler yourself, what are some of your top tips for staying healthy and productive while traveling internationally?
It’s a fantastic question because it’s really important if you take a trip and you’re dead after and it takes four days off of your, you know, your working day, like work week, that’s a problem. So firstly, I mean, for me, you know, really basics, sweat, workout, like before I travel, I’m always trying to work out. When I go over there, tend to, like if I’m going overseas, I tend to build in a day for like a recovery day. So in Europe, there’s so many really awesome like spas, you know, like big spa complexes that have like
You have 20 saunas and the cold plunge and there’s like these things where can go hang out for whole day, read a book and relax. And so I always try to build in a day like that. Cause if I have one day like that, where I just rehydrate and all that stuff, usually I’ve had a few champagnes on the way over. It’s how I tend to travel for business class. So that’s, that’s, that’s another thing. So building in a day, I think another piece is setting proper expectations. I can be really hard on myself if I’m not producing at a hundred percent. And the reality is, is like when I go to Europe, those first few days might be 80%. Like
It’s not gonna be a hundred percent, but that’s part of the trade. mean, that’s having to me like a whole life too. It’s like not every day is gonna be all about business production. Sometimes it’s about having enriching experiences too. So that trade off is worth it, but it’s proper expectations saying that at least for me helps me not be upset with myself about that. And then the third thing I’ll say is there’s a really cool product actually that just came out from a guy named Andrew Herr. It’s called FlyKit. And so what this is, it’s basically an app that’s synced with a protocol based on your travel and your circadian rhythm.
And so he’s a guy I met at an event a couple of years back and he was like a former military ops guy and helped with like high performance there. And so what it does is it basically gives you certain doses of like vitamin D and blue light blockers and caffeine and certain sleeping kind of like melatonin type things. So when you travel, you follow this sequence and if you follow it correctly, the jet lag is like way minimized.
And basically it custom fits to you. So FlyKit is a pretty cool little program out there that will help with the jet lag side. I tested it once, quite candidly. It didn’t work for me because I had a bunch of friends on the flight and I was having a few too many drinks anyways. My other friend who just stuck to the plan, he woke up and he was like, I was like, tell me about it. How do you feel? He’s like, a hundred percent feel great. I was like, that’s awesome. So those are a couple. But yeah, it is definitely a challenge that a lot of people face.
And I think it’s one that’s well worth it if you can just optimize a little bit because that experience is still to me where the juice is.
Most people work hard but don’t reward themselves in ways that truly enrich their lives. Travel is one of the best investments in yourself.
Yeah, I think that’s a big opportunity for people out there because you spend all this money, effort, and resources to go on this trip, and you don’t want to feel exhausted when you get there. My protocol recently has been, yeah, definitely, blue light blockers are key. It’s all about getting your circadian rhythm adapted to that new schedule. On my last trip, I tried high-dose melatonin and also NAD upon arrival, which made a significant impact. It was pretty good.
Yeah, I mean, I think the optimal way to do it is definitely not to drink. You should fly business class for sure, so you can lay flat and sleep. Hydrate like crazy, wear compression socks, and ideally fast a little bit too. For me, my current values are about enjoying the experience a little more, but for someone who’s like, “I really need to maximize recovery,” I would say cut all that stuff out and treat the flight like you’re going to sleep. On those long flights, that will definitely change the experience for you.
Yeah, right. Eli, give us a couple of other examples of people who’ve benefited from the program.
Yeah, I mean, there are a lot of folks we’ve worked with. I mentioned Amber Spears, who runs a big mastermind and is a major figure in the marketing and online entrepreneur space. For her, like many of our clients, it’s not that money is the issue—they could pay for these trips, and many people do. It’s that it feels kind of silly to overpay for something when you don’t have to. It feels a little wasteful, maybe even a little guilty.
For some people, the psychology of spending can be funny. I talked to a client of ours about a month ago. He had just made half a million dollars that day in a video stock trade, so he was doing fine. But he was still flying economy. I asked him, “Why? What are you doing? You have 10 million points—what are you doing?” He said, “I don’t know. I just never figured out how to get the value.” When I showed him how to move the points around, he said, “Now I can justify it.” It was a justification piece for him. He said, “Now it makes sense. Now I feel good about doing it.”
If your values are set around not overspending, you might have a $10 million net worth and still fly economy because that’s how you’ve always operated. Anyway, long story short, Amber wanted to take her grandma to Turkey along with her partner and parents. We put the whole trip together for five of them with lay-flat business class flights. Her grandma had never experienced that before, so she got to show her 87-year-old grandma the lay-flat bed experience. It was mind-blowing for her. She was super elated. For Amber, the ability to make that kind of impact on her grandma while feeling good financially was what made it so special.
We had another client, Glenn Leadwell, who’s Australian. He created a cool site called Mind Movies. If you’re into the Joe Dispenza world, he references that a lot. Glenn’s a killer entrepreneur. He travels frequently from Florida to Australia to Barcelona, so for him, it’s not all vacations but a lot of long-haul international business class travel.
In the first year, we saved him about $130,000 on travel. Compared to what he would have done—13 million Amex points—we got it for 1.2 million points. We saved him an exorbitant amount of money and points while making it easy for him.
There are tons of other examples, like honeymoons and special trips. One of the philosophies I have is especially for the guys out there: Most people do a honeymoon once in their lifetime. I say, do a honeymoon once a year.
Pick a different place each year. Maldives, African safari, Japan, Thailand, a castle in Scotland, the Northern Lights, or sipping wine at a vineyard in Italy. Create a bucket list and commit to a 7-to-14-day mini honeymoon each year. Make it about the relationship. It adds depth and richness.
We encourage people to take this approach. You did Bora Bora for your honeymoon? Great. What about the Greek Islands next year for a celebration trip? You can. That’s part of why we build businesses—to have the freedom to fully enjoy life. That’s what happens for those willing to embark on this journey.
Yeah, totally love that, Eli. It’s so great for people to start thinking that way. And we talk a lot about that on the show—mindset, right? Everything is mindset. But when you start to get some of those different ideas, I think it’s hard because we’re all kind of doing our daily grind, moving through things, and it’s hard to think about these bigger ideas.
But when you can be intentional, now is a great time of year to think about your next 12 months. What’s that bucket list trip you’re going to do? Or that next 90-day trip to actually get away? Those are just great ideas to think about. It also really resonated with me—the mindset of how you’re thinking about it. It’s kind of like if you go into a mall, you’re paying retail for everything at the absolute max price.
So when you go on an airline and click business class, you know you’re paying the absolute retail price for that, and you want a good deal. I love the fact that you can kind of hack your way into getting the experience while also getting great value.
Right, 100%. And if I can, I’d love to give one tip for people listening in terms of getting the best value and thinking about how to set up their travel and planning.
There are really two key things to unlock the best value and experience for points: planning ahead properly and being flexible. With planning ahead, the best time to book—though not the only time—is around 10 to 11 months out. That’s when airlines release their seats for routes, and there’s the most availability for good deals.
Now, if you’re six months or four months out, it doesn’t mean you won’t find a deal. You will. There are just more options when booking earlier. This is a game of stacking the deck in your favor. So, the ideal windows are really far out, like 8 to 11 months, and very close in, like two weeks, one week, or a month out. Airlines tend to open up more seats close to the flight because if they haven’t sold them, they’d rather get points than leave them empty.
Here’s a cool part: points are refundable. If you book a business class flight to Europe 10 months out and aren’t sure if you’re going, but you find a great deal, just book it. If you need to cancel, you get your points back. You’re not stuck with a $5,000 airline credit for a random airline you’ll never use. You just get your points back.
The second piece is flexibility. This is important, and I really recommend it for big international trips where you’re saving five figures. For shorter domestic flights, like Sarasota to Vegas for a conference, just book the easiest direct option. But for trips like a month-long vacation or two weeks in Italy, flexibility opens up a lot of options.
For example, if you can fly out of New York and take a hop from Sarasota to New York or Atlanta, you’ll have a world of options. If you insist on flying direct from Tampa, there may only be two flights that day. If you’re flexible with your dates—say, early June instead of June 9th—you go from two flight options to potentially 300. That drastically increases the odds of getting a great deal.
So, for big flights—like trips across the pond or around the world—flexibility is absolutely key. It doesn’t mean it won’t work if you’re rigid, but it’s much harder to stack the deck in your favor. This is a big tip most people miss. If you can expand your flexibility a bit, it helps a lot.
Yeah, great tips. Are there any search engines you’re preferable to, like Kayak or Google Flights?
Yeah, so for cash bookings, definitely Google Flights is the best. There’s some really cool stuff you can do with how you can set filters and multi-city airports. It’s kind of advanced—there’s an advanced mode in Google Flights, let’s say. So if you’re trying to figure out what flights you have available, that would be a good starting point. But that’s actually not going to be great for showing you points deals. It’s just good for showing you what airlines are operating.
Another cool tool if you want to figure out what airlines even fly certain routes: most people, for example, have you ever flown that Emirates flight into Milan? Did you know about that one?
I know about it, I haven’t taken it.
Okay, cool, cool. Oh, it’s a well-worth-it experience, especially if you think about maybe stopping in New York for a day or two. You can parlay some meetings and stuff—I tend to do it like that. But most people don’t know that Emirates flies that route because they typically fly to Dubai since that’s where the airline’s based out of. So there’s a cool tool called flightconnections.com. What this will do is show you, you just punch in the city you’re flying to or from, and it will show you all the nonstop routes on all airlines across the world. You’re like, “Oh, I didn’t know that Emirates flew that route from New York to Milan. Who knew?”
So you can start to see how you can piece together an itinerary if you want to get creative with it. That’s a cool tool for that.
For the points deals, this is where things get really interesting because there are a lot of new search engine points tools coming out. There’s point.me, Roam Travel, Points, Expert Flyer, and Seats.arrow. These are all different tools, but they’re built for different types of trips. So there’s not really one to recommend. Some of them work all the time for certain things, and some don’t work at all for others.
It’s very situational. Our team uses all these tools to set alerts and track deals. For the average user, Seats.arrow is a good one. Point.me is okay, but it really depends on the kind of trip you’re looking for. You need to know how to use them effectively to get the best deals. So there’s not really one robust option yet. Maybe in a couple of years that will happen, but for now, you have to manually know how to search through and find the gold.
Yeah, are you guys using any AI tools for this?
So the ones I mentioned have AI integrated into them. But right now, again, there’s not a lot out there that’s great with AI yet. There are a lot of challenges with that. Besides from the couple I mentioned, there’s a lot of challenges because of the API structures with these bank programs and airlines and the way they work. I’m not in that world of development, but I do understand from afar that’s one of the complexities. There’s a lot of real-time data that has to be updated and stuff. So not a lot out there yet.
Okay.
We’ll see as it continues to evolve. I think there are a couple of people trying to solve it, but those that I’ve talked to in the AI world are like, “That’s like step three. There needs to be a step one and two first.” I think it’s still going to be a little while.
Yeah, makes sense. Eli, if you could give just one piece of advice to the audience about how they could really take their travel to the next level, what would it be?
It would actually be to get the right credit cards. Most business owners are way overlooking the card, how important it is, and how much they’re leaving on the table. It is the easiest single thing you could do to unlock more travel. Even if you don’t use the points well, if you just tripled the amount of points you got and went from getting a million a year to three million a year, even if you don’t optimize how you use them and just use them ineffectively, you still just got three times as many free trips from what? Applying for a credit card that took 45 seconds.
So, think about the time of inputs for return. If you figure out how to get the right credit cards or get help from someone like us or someone else online, that’s highly worth it. And that would actually be my biggest tip. There’s a lot of other things, but if we’re thinking about highest leverage, that’s the one.
Yeah, awesome. Well, this has been really eye-opening. I really appreciate your time and wisdom today. If people want to learn more about your system or connect with you, what’s the best place?
Yeah, so I’ll give you a couple different options depending on what you’re looking for. If you’re just like, “I like this guy, I wanna follow him more and engage more,” Instagram is the spot. So I’m Eli Travel Guy. That’s just Instagram.
Then we have a playbook. If you’re like, “I kinda wanna get into the, you know, figure out my game plan here,” you can go to freedomtravelsystems.com. That’s our company. Freedom Travel Systems, forward slash playbook. You can grab that. It’s basically the CEO points playbook that walks you through the foundations of picking the right card for you, creating your own travel DNA, figuring out what airlines are relevant, how to get your hotel suite upgrades, and it goes a little deeper into some of these core concepts.
And if you’re like, “Hey, I just want to talk to someone from your team to potentially have you guys just help do this,” you can just go to freedomtravelassistance.com and set up a call with myself or one of our team members, and we’ll see what we can do to help you out.
Awesome, really appreciate it. Thanks again, Eli.
Cool, thank you, Dave. Appreciate it.