← Going Big! with Kevin Gentry
Going Big! with Kevin Gentry
Unlocking the World: How Travel Opens Doors and Creates Opportunities with Gary Leff
00:58:41
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- [00:01]
Gary Left
And you know what, for me, paying attention to these things did is it opened up the world, but it also allowed me to open the world up for people that I cared about. I mentioned family in Australia. My uncle moved there, my aunt. They had kids. Their kids have had kids. And my late grandparents would travel there to see their grandkids and kids. Right? And it got to the point where they were old. It was a difficult journey in economy. They could actually afford to travel in business class. But they grew up in the Depression. It just wasn't the kind of thing that they would do. They never saw themselves as the people who would spend that money in that way. And so they just wouldn't make the trip because it was too arduous for them and they wouldn't buy that. But I could use my points to send them in first class, and then they would actually go. And so I remember doing that, sending my grandmother on a trip in first class that she never would have been able to take to see her son and grandkids, and how meaningful it was to be able to do that for people that, you know, did things for me.
- [01:06]
Kevin Gentry
Hi there. I'm Kevin Gentry, and welcome to the Going Big Podcast, where we'll explore some of the strategies that can help you transform your effectiveness by 10xing your fundraising. Each week, we'll sit down with some of the most influential business leaders, CEOs and nonprofit visionaries to talk about leadership, the power of giving, and how you can make a real impact. If you want to make a transformational change to the cause you're working on, this is the place for that conversation. Also, take a Look at our website, 10xStrategies.com that's T E N X strategies.com for lots of free marketing and fundraising resources. And be sure to sign up for the free weekly fundraising tips. Now, let's dive in. Well, ladies and gentlemen, I am pleased to welcome to the Going Big podcast. Gary Left, one of the world's premier travel experts, founder of the highly popular travel blog View from the Wing. Gary, I just want to start right off the bat. How did you turn an interest in airplane travel into a website that gets millions and millions of views from around the world? How did it happen?
- [02:22]
Gary Left
You know, gosh, it was not something that I set out to do. I, 23 years ago had friends that were starting blogs. I lived in D.C. for 18 years. They were starting political blogs back around 2002. And look, I have. I certainly have my own opinions, but I didn't feel like I had anything to say that nobody else in the world was saying in that space. But because it was something that was kind of taking off, I said, well, what do I have to say that is somewhat unique? What did people ask ask me about? What do people come to me for? And I figured that that would be something that would be value I had to, you know, to add. And so I just started writing mostly because I had something to say and it was a way to tell the world. And that way I didn't have to bother everyone else around me with my thoughts. And you know, I write as though nobody is reading, which was the case more or less back in May of 20 of 2002 and not really thinking about the large number of people there who do. I'm certainly, you know, grateful and happy and I get to interact with some, some amazing people because of it. But, you know, I just write what I think all the time. And if people have, you know, value that I think that's great.
- [03:45]
Kevin Gentry
Well, it's a fascinating story and it's a great story of going big. You're clearly, I mean, you may be writing what you want to write, but there's an audience for it. So help our listeners today understand what, what do you do in terms of offering a benefit to travelers today? What do you, what kind of are they? Insights? Is it advice, suggestions? What are you offering?
- [04:08]
Gary Left
So there's, there's a few different things that I do. But I mean, starting with the blog and what I write about is I write about the travel experience. I write about frequent flyer programs. I write about airlines and their policies and changes that they make and how to approach problems when you travel, how to get the most value out of travel dollars. And so I write about, you know, also just as an interested observer in the airline industry, hotels, to a lesser extent, you know, rental cars and these other elements of it. But you know, I'm writing about the, the news of the day as well as opportunities that come along. So I'm going to write about, you know, gosh, I mean, these things don't come around very often. But three years ago, American Airlines at the holidays they have a website called simply Miles. It's a joint partnership with MasterCard. It's card linked offers. You link your credit card and then you, you add an offer and then you transact with a merchant and you'll earn American Airlines Miles. Well, at the holidays they were running a promotion of sex tuple, the usual points. And MasterCard was offering to give points for donating to a charity that they support and they were offering 40 miles per dollar. Well, sex toppled. That's 240 miles per dollar. And by the time the whole thing is, you know, in the end, you basically have an opportunity to buy effectively an unlimited number of American Airlines miles at around 40 basis points. Well, that's like pretty good, you know, considering, you know, that, I mean, they'll normally sell you points for, you know, two and a half cents. But I wouldn't be a buyer at price. But at, you know, 40 basis points, you're buying a business class ticket to Europe for around $325. So I wrote about how to take advantage of that. And look, I took advantage of it to a large degree to millions of miles, but I had readers that were buying tens of millions of miles. And look, it's not the first time that I wrote about how to get several million miles in a day. You know, we wrote about back before US Airways acquired American, US Airways had an offer also around the holidays and also for shopping with their partners, where what you did was if you made purchases from between five and 10 different partners, you would earn a 250% bonus on top of the normal miles that you earned. And, you know, I wrote about the ways of getting the cheapest transactions with their partners so that you could get to that bonus. And then what you wanted to do was make a purchase from a company called Track It Back. And what Track It Back sold were stickers. The idea was you put stickers on things that you cared about and if you lost them, they would help you find them and get reunited with your belongings. Like, you know, you'd call the number on the sticker and whoever found it and they'd get a reward for calling and then they would handle the shipping to get it back to you. Maybe you stick it on your laptop or your phone, but it only cost them to produce stickers. And it turns out even the reward that they would give to whoever found your thing was like more stickers. Very, very low cost thing. They were offering 40 miles per dollar. And what we did was talked about how to like get these points. In fact, I, for myself and others, wound up sitting down and picking up 16 million US Airways miles because crazy.
- [07:51]
Kevin Gentry
All right, well, okay, hold on. So we're going to get into a lot of stories like this. This is amazing. And I mean, full disclosure. You and I have known each other for a long time. We were working together just before you started your blog. And I remember then in our office you would say, hey, Air Tahiti, I must have an accident. Instead of a flight for $1,790 to Tahiti, it's $179, go get it. And I remember people in the office like, okay, I'll go to Tahiti for $179. So you've had this knack. Help us just understand. How did you build and scale something out of, out of, you know, you were working at the time. You're working at a non profit organization as the chief financial officer. How did you take this hobby and turn it into something much bigger?
- [08:41]
Gary Left
Right, so, so, so you remember this because of course, you know, before I was cfo, I worked for you. I did fundraising when you were at Mercatis and IHS and, you know, working. And one great thing about this was, you know, that could travel in development. That was great. And do, you know, visit supporters. But also, you know, it was work that I could, you know, do from anywhere. And you were just happy to see, you know, great work getting done. You were blind with my taking the trip. And so I come around and I would tell people in the office, you know, does anyone want to go? This was actually one. Right, right after you left, there was a deal that came up. I said, anyone want to go to Cyprus? Want to go to Cyprus? Well, Alitalia was trying to publish a discounted business class fare of $3,300 round trip, and they published it for $33 plus tax by mistake. And so we actually wound up issuing about 28 tickets in the office for business class to Cyprus. In fact, there was a woman in the office who told me the story where she was flying back and talking to the woman nearby her in the cabin about her trip and why did she choose to go to Cypr places? And her response was, and she's sitting in business class. Her response. Well, it was the cheapest, right? This is like, what are you, what are you, what are you doing? And so there, you know, there are these, there are these deals. And as I say, it was just something that I was, you know, talking to people about and, you know, they would ask me advice on. And so I would write about it thinking that this might be something people would be interested in reading about. And, you know, it's just something that I would do, you know, as a hobby and on the side. And I wasn't writing nearly as much back then because it was, it wasn't even intended initially as a, as a business. But as it began to grow, you know, I eventually, and I was always transparent with what I was, you know what I was doing and what I was writing about because I would do the travel for all the people that you know, around that I work with. And you know, I was transparent and said, look, this is something that I'm doing and I'm doing more of. And, and folks were generally happy as long as I was doing, you know, not just all the work, but you know, 110 or 120% of the work. And, and as long as everyone's happy with it, the particular time or hours that I was doing at the moment wasn't what mattered. But I did eventually move out of D.C. after living there for 18 years. And I said at the time, you know, look, I love working where I am at Mercato center and it' do for human studies. I care deeply about it. I would love to continue to do this, but I also need to pursue this other thing I suggested. Can we reduce my, you know, salary somewhat in recognition that I do have other things that I'm paying attention to. But my own personal approach is to basically do, you know, whatever needs to be done and however many hours that I need to do them. And, and, and this is this. When I write about travel, it's a passion. You know, some people watch football and I think that's great, or you know, baseball or hockey. Right. And I analyze frequent flyer programs. You know, I'm, I'm. One of the things I think, I hope, you know, makes me pretty good in the CFO role is really getting into the details and you know, nitty gritty and just diving into numbers, but also being able to pull back a lens. And I think I got much better at this, you know, especially in writing and communicating for development to be able to, you know, communicate at a higher level level, communicate clearly, especially for folks that are not specialists. So I become the specialist and offer the articulation, but in a way that is accessible to, you know, intelligent non specialists.
- [12:35]
Kevin Gentry
Well, it's an amazing story. It's a great example of a win win. But what an awesome story about taking your hobby, your passion and then making a business out of it. It's, it's really quite extraordinary. And I, and it's obvious that you enjoy it. You love it. Well, to help give folks a taste of what you do, how about we do speed round. I'm going to ask you some questions about travel and, and if you can treat us as though you're just, you're giving us some good counsel. So how about we start off, if I'm a young person, just maybe Just out of college, just going into, to work. And maybe my business, my occupation requires travel or maybe I'm anybody that says, hey, I need to be a smarter travel. Do I sign up for every major airline, frequent flyer program and hotel program? How do I start?
- [13:24]
Gary Left
Well, there's no reason to sign up in advance before there's a need per se, just for the, for the program. You know, I think you start with you. You certainly want to sign up for programs. Don't leave points on the table. If you're walking down the street, you see $20, $20 isn't worth what it once was, but it's still worth picking up. You know, the, the points are worth it. Even if you say, well, it's just a few points they eventually accumulate in a lot of programs, they don't even expire anymore. You know, you're going value that's useful eventually. If you're just starting out, you have a lot of years in which to accumulate enough for it to be valuable. And it's, you know, fairly low cost to do so. So absolutely, you want to accumulate the points. You know, one of the things that I do is I use a website called AwardWallet.com to track all the points. It can get pretty cumbersome if you're going to be signing up for all the programs. And eventually over a lot of years between all the hotel programs and airlines and rental cars. But I enter my account numbers there, my password there, with, you know, single click, I update all my account balances. I can log into any of the accounts. It's just a great place to store all that and, and keep it easy and organized.
- [14:37]
Kevin Gentry
Interesting. What's the, what's the website called Again?
- [14:39]
Gary Left
AwardWallet.com is AwardWallet.com.
- [14:42]
Kevin Gentry
Got it.
- [14:42]
Gary Left
There's a few like there, but that's the one that I use.
- [14:45]
Kevin Gentry
Excellent. Okay, so are there some airline programs and hotel programs in particular that are better than others in terms of value? I've gotten the impression maybe from you or others that, for instance, Hilton is really not the greatest from the standpoint of points, but it used to be Marriott was much stronger. I don't know. You tell us.
- [15:05]
Gary Left
Yeah, so I would say that different programs have different strengths that appeal to different guests. The first thing to understand is that every loyalty program just about is really two different things in one. There's recognition and there's reward. So recognition, taking care of your best customers with benefits that aren't available, everyone. And that's your elite program. And that's different than Accumulating points, redeeming points, getting free travel or other, you know, upgrades or something else out of, out of your redemptions. And you know, I would say that in general for recognition for the elite program, Hyatt's program is by far the best for their frequent customers.
- [15:48]
Kevin Gentry
Interesting.
- [15:49]
Gary Left
They are, you know, when you talk about their, you know, late checkout, it's, you know, guaranteed at the most, at the highest percentage of properties. Your, their breakfast isn' just continental, complimentary. They even specify, you know, what a breakfast is. So the hotel can't, you know, can't play any games with it. It's, you know, hot breakfast or the buffet, you know, their upgrades, you know, include suites, but they even let their top elites confirm the suite at the time of booking several times a year for up to a week at a time. You say, this is the time. It matters to me, you have the suite. So it's not just if it's available at check in. But I would say that the challenge with Hyatt is while they've grown a lot, you know, they are not nearly as Marriott and IHG and Hilton. They also especially don't have as many properties in the small towns across America. So they're going to be strong in more upscale segment and in major cities and major cities around the world. So does your travel patterns work with a Hyatt or not? And even if you decide you really like Hyatt because of their benefits, you might need a second program for those times when you aren't in a city that they serve very well. So, you know, then you say, well, you know, what Marriott has used to be the program that they didn't promise a lot, but they always delivered consistently. And that was really their, their San Quantitative were, that's, that's what they did. And since they acquired Starwood, they've kind of gone the opposite direction. They acquire, they promise the moon in terms of the program. And the actual experience is incredibly varied across their properties. Sometimes deliver, they frequently don't. So I find that often, you know, Hilton's customers are a little bit happier on average in part because they actually don't promise for it. Hilton's program doesn't, doesn't even promise, does not guarantee late checkout to their most frequent customers. They say they'll do it if it's available, it's really up to the hotel and they're asked to do it, but it's not a promise. And so everyone is usually pleasantly surprised by whatever they get from Hilton instead of being disappointed relative to the, to those promises, the commitments that have been made by Marriott. And so, and then you'd look at, well, you know, so who's got the footprint that you want for the hotel? Who has the property? Is that kind that you're going to stay at and value? Some people are just looking for a place to spend the night, right? And they say, well, if I'm going on vacation, I'm not going to be in the room. Other people say, I really want that luxurious room experience. Or I'm going to be at resorts or I'm going to stay on property and I want those nice, more expensive places. So whose property is it really appeal to you? And then you make sure that you sign up for the promotions that they have when they have them. When I get the email for a promotion from a program, I click the button to sign up immediately because I'm never going to remember to go back and do it later. Or I say, oh gosh, I'm not going to do it because I'm not staying with Hilton this quarter. Well, guess what? Then I'm on the road somewhere and I'm spending an extra day somewhere and it turns out that I'm at Hilton. I'm not going to go, oh, there was a promotion, I better go register for it. So I just click the button, right? And I want to sign up for all the promotions that I can.
- [19:04]
Kevin Gentry
That's great advice. What about airlines?
- [19:07]
Gary Left
So I, in terms of the airline programs, I would say that the first thing is, you know, where do you live and who has the most service, you know, there, right? And, and that's going to matter a lot. But the programs are, you know, fairly different. Delta sky miles is perfectly fine with their elites. Their miles are worth not worthless. They're worth less than other airlines. You know, 16 years ago, I believe I coined a phrase called sky pesos for their currency that seemed to have stuck. It's used quite broadly to describe their miles. Their vice president Charter Sky Miles will tell you that they are not trying to compete on value to their customers with their mileage program. In terms of redemptions that they view, look, they are moderately friendlier, a little bit more reliable as an airline. They're seen as a bit more premium and people are choosing them for that reason and that they're not investing as much redemptions and it seems to work for them in terms of attracting customers. But if what you want to know is whose miles are going to get you go farther? It's not going to be Deltas. Look, United's Miles are good in the sense that they have more part if, say you want to go business class to Europe, right? United just has a lot more airline partners than American Airlines does. That'll take you across the pond and so you're going to have a lot more opportunities. Americans, Miles, they've really leaned into the Advantage program relative to some of these other airlines in terms of their redemptions because they haven't had as much on the experiential side of the airline itself. It's been an opportunity for them to distinguish themselves. And that's what the mileage program is originally for, to distinguish what otherwise at the time was treated as a commodity product. And I mean, American still does that. American is the easiest to earn status with with activity other than flying, right? The most sorts of activity count from credit card spending to online shopping through their portal. I mentioned simply Miles card linked offers though that mileage earning counts towards the mileage requirement for status. So, you know, we can rent cars or fill up gas, you know, any of the activities with their partners will count towards that status. And so some folks say, look, I can earn a much higher status with them than I would with other airlines because I'm not flying, you know, the 100,000 miles, spending 24,000 or $25,000 in airline tickets in a year. But I can still be, you know, a top status by being all in with the mileage program program. And that works for American because it turns out that all the things that the airline partners with and sells their miles for is much higher margin than anything to do with flying. Flying is, you know, it's very expensive. Planes are costly, fuel is costly, their labor is costly. And it is for the most part the competitive commodity business. You know, the margins at the best end may approach 10%. It's not like a software business. And for many airlines, the margins on actually flying are either break even or negative. But selling miles while America, during the pandemic, the airlines went and leveraged their frequent flyer programs to borrow against. And the three largest US airlines borrowed between 6.5 and $10 billion each against the future revenue streams of their loyalty programs. But they also at the time had to disclose then a lot more information about the economics of the programs because they were going into public markets to borrow this money. American disclosed a 52% margin on the Advantage program. Now the, the accounting here gets a bit wonky, you know, between the programs and how much they charge themselves internally for flights. So Delta is only reporting a 37% margin. It doesn't Mean really that Americans is that much more profitable than Deltas. But the point being that the margins are, are orders of magnitude higher selling miles. Right. Than. Than. Than transporting passengers and planes.
- [23:06]
Kevin Gentry
Amazing. Well, you know, I've shared the story. It's a, I, I think it's a funny story, my own experience. I started flying 1986 right out of college. I had a job that had a lot of flights. I signed up for, you know, United America, all the flights, airlines at the time. But United has become my airline of choice because I live in the Washington D.C. area and Dulles is a significant hub for United. And so. And it used to be with the partnership with USAir, I could dovetail with stuff at Reagan national as well, but hit the 2 million mile mark a couple years ago. I reached out to you at the time to tell you the story. United missed the actual flight where I crossed 2 million miles because I was tracking it with, through my app. They have a great app, by the way, I think. But on the next flight, they thought that was the 2 million mile mark. So the pilot was a small, short flight, came out with the manifestation and he had the whole crew sign it and give it to me because that's the only thing we could come up with that was creative to give to you. I'm like, well, that's very nice. So the next flight I was on, they thought that was the 2 million mile mark. So I'm trying to be a good sport, neck surprised. And they did some funny things and they got like a napkin and covered up a sparkling wine bottle and used the little plastic wings to hold it together, kind of like a diaper. And then that was kind of funny and got my picture taken. And then next flight, I was flying from Denver to somewhere and we were getting ready to take off and the head of operations for United at Denver comes on board and says, ladies and gentlemen, we have a special announcement. We have a special guest on our flight tonight, someone who's about to cross the 2 million mile mark. So I act surprised came up, got to sit in the cockpit, got a picture taken. It was all kind of fun and nice. It was kind of funny. When I went back to my seat, an older lady asked me, she said, what did you win? And I explained what had happened. And she goes, well, that doesn't sound like a very good price having flown 2 million miles. But anyway, you publicized that. I thought that was really neat. And I didn't know whether you had any comment. I thought that United's recognition, though, was special and I'm talking about it still today.
- [25:25]
Gary Left
Yeah, well, look, I mean, and it was actually really helpful when you flagged this for me because it was early on in noticing that United had gotten very good at in flight recognition of milestones. And they are good at it in a way that no other airline is. And you mentioned their app. They actually do have the best airline app in the world. This is, they're generally regarded within the industry as that being the case. But I do think that that milestone recognition is something that is seemingly hard to do, but once you do it and create a process around it, it's not and it's not that burdensome because you don' that many people on a daily basis crossing, you know, 2 and 4 million miles. I mean these, these milestones are incredibly significant to the customer and, and really worth it. As you say, you know, you, you, you, it's, it was, it's your, you know, George Clooney up in the air moment, right? I mean this, in the, you know, in, in the, in this film, right, where George Clooney is on this quest for 10 is 10 million miles. And it's based on the, a book up in the Air where it was back then only 1 million mil. He's, he's on the flight and when this happens, the chief pilot of the airline comes out, right, played by Sam Elliott, sits down in the empty first class seat next to him to have the conversation. But it's this thing that he had been imagining in his mind for a really long time. 2 million miles happens over, over a career. And it's a career of, you know, spending tremendous amount of time in the air making choice after choice after choice to stay with the airline through good times. Had, you know, I had a conversation one time with a former, former CEO of, of Marriott shortly after he purchased, after they purchased Starwood. And we're talking about loyalty. And he says, you know, loyalty to me is, you know, we're going to have for the best, you know, value to the customer on every trip. I said, no, it's actually the opposite. I, I told Arnie Sorensen, you know, late, you know, late head of the company. I said, look, loyalty means that the customer is going to choose you even on those individual trips where you don't offer the best value, right? It's the overall value proposition over time. It's a trust relationship that you build and when you take steps to recognize it, not just in a programmed sort of a way, but in a very personal way when you're a big corporation that Actually personalizes it and creates moments that is often more powerful than, you know, the given upgrade. Right. One of a million flights.
- [28:18]
Kevin Gentry
Well said, Gary. And you know, I think very few people appreciate the enormous power of lifetime value. And whether it's the, you know, whatever they say, the $14,000 value of a, of a Starbucks customer or like, you know, I'm going to keep flying United at the margin every time I am for a variety of reasons. And my next goal goal is to get to 3 million lifetime miles because at that point I'll be 1k for life, which means I get priority boarding and other benefits and things like that. Now, I may be 80 years old when I get to 3 million miles, but it does give me a reason to keep doing it. All right, well, let's. This is awesome.
- [28:56]
Gary Left
I'll tell you one other thing that, one other thing that they do with lifetime that I think is really smart is that the lifetime members, spouse, spouse get is, can be conferred that status. In fact, it's not just the lifetime status, it's whatever status that member holds at that time. So if you're a 1k but only a lifetime goal, the spouse is a 1k as well. Taking care of the people who matter most to the valuable customer is often more important than how you treat them.
- [29:28]
Kevin Gentry
That's a great point. And yes, my wife is 1k for as long as I'm 1k and she doesn't fly as much. But when she does, she has that benefit that she probably otherwise wouldn't have because she doesn't fly enough to get that status. All right, well, let's keep going on and some of the advice that you would give. Let's say I'm going to get ready, I need to travel somewhere in the United States. I need to travel to San Francisco or Dallas in two weeks. How should I think about booking the right flight and think about that trip? And let's say it's probably a business trip, but I have the power and the authority to choose the trip, travel and, and to book it.
- [30:10]
Gary Left
Yeah. So I mean, there's a bunch of things that go into it. Say, say it is a cross country trip. So you're going, it's long enough that you're going to care about the in flight experience, the comfort or the, and having enough space to work. So it's different than maybe a, you know, 50 minute flight on a regional jet. And so there I'm going to say, well, where can I get the, you know, maybe extra legroom economy seat so that I can Open my laptop. That's going to matter to me probably more. Is it going to be on an airline that has functional WI fi? Because that matters to me. Different people, you know, different. Some people want to be. To escape when they're on the aircraft. For me, I want to make sure that I have functional WI fi. That's not just going to work, but it's going to be fast. Now, United has been an airline I've not wanted to fly because their WI fi hasn't been up to industry standard. That's about to change, right? I mean, United is. Is starting to install Starlink WI fi that's f. Faster than what anyone else has. The satellites are in low earth orbit. What you have is basically no latency when you're in the air. And so they're making a big leap. But, you know, I say, okay, who do I want to fly? Where can I get the. The space that I need to work and the tools that I need? So the WI fi. I'm also going to care about your reliability. People often choose, you know, Delta because they're going to be on time a little bit more, you know, often than, Than American. Um, that. So it's. What are the elements of the trip then that matter the most to you in terms of, you know, choosing the schedule? Obviously, you know, price matters and when you need to travel matters and how much you can trust whether they're going to get you there at that time. But look, how important is that trip and making it, you know, on that day, it's there. There's some trips where, you know, if my trip doesn't go the way that I plan, I could bag the thing and go home and we do it again a different time time, or we wind up, you know, on a zoom. I've made my effort and that works. And there are other trips that, you know, are, you know, it's life and death that you're there. You, you just can't get those people, same people in a room any other time. And opportunities are going to go away that are really significant if you're not there. And I say, okay, at that point, how do I make sure I've got backup options right? Or even think, you know, forget that it's two weeks from now. A San Francisco trip. Maybe it's the holiday holidays. And, you know, it's really important to you that you make it to your family over the holidays. And you know that planes are going to be full if your flight cancels, the ability to get on another flight is going to Be really limited in time to make it for, you know, for the events that you want to be there, there. I actually might book two itineraries and this sounds crazy. What are you going to spend extra money for? No, two things. First of all, what I might do is I might buy one ticket and I might redeem miles for ticket on a different airline, say four hours later. And if my first flight goes off without a hitch, great. While I'm on the plane, I'm on my phone, I cancel the other itinerary. Most programs will now let you cancel an award, redeposit your miles at no cost, right? So you get a free backup option. If you've got miles in your account, say that you don't have the miles to do that, you do have the option. Most tickets now don't have change Feees in the US so you would be buying another ticket, but you cancel it and retain a credit to use in the future. You want to make sure that it's on an airline that you're going to use the credit. But look, you know, the rules of different airlines are sometimes more generous than they used to be. Southwest Airlines credits, for instance, never expire anymore. So you're not saying, okay, do I have to use it in a year? If it's a Southwest ticket, that's your backup. I will often buy sometimes a ticket from Southwest or Delta as a backup on the day of travel when my airline won't put me on the other, on that other carrier. They're delayed and I don't know if I'm going to, to make it because both Southwest and Delta will honor 24 hour, no penalty cancellation, full refund even on the same day of travel. American won't, you've got to, you've got to book you, you've got to be buying at least a week in advance to take advantage of the 24 hour free, free refund from American. But I have, you know, say, okay, I need my backup. Delta's a backup. I'm buying that ticket. And if my American flight cancels and they're not going to get me there, I've got this other one and I canceled ticket on American. Well, that one gets refunded. And you know, look, it used to be when I started traveling for business, those last minute tickets were excruciatingly expensive. That's not always true anymore. You know, the advanced purchase requirements as a way of differentiating leisure from business travelers aren't a thing for the most part anymore. Saturday night stays aren't either. That's something that changed or ran 18 years ago with as the low cost carriers really came to the fore and forced the major airlines to change their own pricing policies. That's why we get basic economy fares, by the way. It's not to get people to buy up for $40 more. It's really to continue to differentiate business and leisure travelers because they can no longer use the Saturday night Stay and the 14 day advance purchase to do that differentiation. It's the ability to, you know, price discriminate. You know, some people will pay a small amount for the flight and others will pay a lot. Well, how do we do? Well, we do it with these other restrictions of basic economy now. So these are some of the things that go into my, to my mind. But as the travel day, well, go ahead.
- [35:51]
Kevin Gentry
Well, so, so okay. The key point here is though, there's a lot and nobody knows as much as you know about all of this. So how do we become a better informed traveler? I'm better informed today than I was 10 years ago, 20 years ago from experience. And the more I do and the more I try, the more I learn. But I'm going to also learn a heck of a lot more from somebody like you. How do we all become better informed travelers? Do we look at you go to your blog frequently And I don't mean for you to, you know, pick selfishly the route that is best for you. What I mean is, what is your advice to help us? And maybe it is to go to your blog. How do we become better informed?
- [36:32]
Gary Left
Well, you know, the funny thing about your mentioning the need to just have the experience, right, is there's this need. Nietzsche quote. He says that, you know, he who would one day learn to fly must first learn to stand and walk and run and climb and dance. One cannot fly into flying. So he uses flying as the example of having to engage in the world. Of course, we didn't have modern air travel in the same way when he was writing, but I think that I, I will tell you that travel is incredibly complicated. It is too complicated. And that I always thought that technology would solve for a lot of this. That, you know, Google Travel would tell you not just what flights exist and what their prices are, but offer advice that says, you know, maybe you don't want to take the short connection in Chicago in the wintertime or it would learn from your past behaviors. You know, they've got all your itineraries in your email with Gmail. You know, usually you book long connections. This is a short one, is are you sure, you to do this and ask you these kinds of things, and we haven't gotten there. And surely AI is going to help with all of this, both learning about what is likely to happen and learning about your preferences and flagging issues and how to fix them. So maybe, you know, maybe this is all going to be a moot issue in a few years, but in the meantime, you know, yes, travel, yes, read if you're interested. But not everyone's going to invest that money because often in reading about it, you're investing, investing more than your, you know, up front. You're going to get and pay back. Right? And so you've got to enjoy that, that investment, too. For the sport of it, you can outsource some of this. Look, there's a, a guy that I know, Brett Snyder, has a company called Cranky Concierge. No travel agency likes to do air anymore. There's no money in just air. All the agencies like to do, you know, big tours. They like to do hotels. There's money in booking those. So he's got a company that really does pretty much just air, and it's.
- [38:43]
Kevin Gentry
Called the cranky concierge.
- [38:44]
Gary Left
Cranky concierge.com. and what they're really good at is you book through them and then something goes wrong and they, in your travels and they're with you to fix it. You know, figure out what your alternatives are and work with the airlines to get you where you're trying to go. They're also pretty good at finding, you know, good, you know, good fares, you know, good. And all of these things that can be worth it as well. They can even tell you, you know, where, eat in the terminal area that you're going to be, you know, be in. Because, yeah, look, people ask me, right? And I'll tell you, you know, where I think you should eat. There's only one good restaurant in any airport in the United States, by the way, and it's not one flu south in Atlanta. It's tortoise frontera at Chicago O'Hare. Although there's multiple locations, you know, I, I will occasionally say, you know what, at the margin, I'll choose to connect in O'Hare because I can pick up a, a cherry queso sandwich from, from the Rick Bayless sandwich place there. The interesting thing is, you know, when, when you go to an airport, you say, oh, there's this brand that I know and I like that restaurant. I'm going to go there. It's usually not the restaurant or any of the people. Don't Work for the restaurant. They work for a big concessions company that has the concession at the airport, and they're licensing the brand. You know, if you go to National Airport, it's. They've got the only remaining Taylor Gourmet in the country. It used to be a sandwich shop. They grew too fast. They went bank. The concept was licensed by the concessions company, so it's still in the airport. So I can still get their meatball sandwich. But, but, but, but the point being is that usually they're. They're creating awful food for, you know, lowest common denominator for every. For the median traveler to serve quick. They can't, you know, in most places, you've got knives that have to be chained to the wall, right? Because you can't just have loose knives in the airport for security. And they're inventoried every hour and there's no storage space. And you can't bring stuff through the airport in the middle of the day because of. People are having to go through security as you got to bring them in like once a day at night through, you know, one vendor, what you can get. So airport food is awful. Except Rick Bayless said, if you want me in this airport, you know, I need to have a separate prep kitchen and not just these, like, spaces, right? And we have to solve this problem, and I won't do it otherwise. And I think it was HMS Host, but I have to check that says, you know, you're crazy, you know, and making the food this way, you know, is not what people want. And he said, well, this is the only way I'll do it. And so they make decent foods anyway. If you're going through Chicago O'Hare, you pick up a Rick Bayless sandwich at Tortoise Frontera, either in the American or the. The United terminal.
- [41:20]
Kevin Gentry
Yes, I agree with you. It's a great sandwich. All right. Another quick question. Different question. Let's say we want to plan a vacation and we've got time. It could be a year from now, six months from now. We've got flexibility. We don't know where we want to go. Just some quick things we should think about with respect to our airline miles, hotel points about planning something like that.
- [41:44]
Gary Left
Well, if it's a year away, you could potentially even earn some more miles, right? For, you know, for the trip. And you say, gosh, you know, what points do I have? You know what, you know, what does a trip usually cost? Do I not quite have enough? Maybe I have enough for economy, but I want to go in business class. You Know, maybe So then I, I say, well, there's a great offer from this credit card that has a hundred thousand points. If I take it meets the minimum, minimum spend. So maybe I'll get that card and if I'm going to do it, it makes sense for me. Then maybe it makes sense for my spouse also. Maybe I have a small business, maybe I'll get the personal card and the small business card. Well, now I've got not, you know, 100,000, but I've got two and 300,000 new points with credit card offers. If I'm willing to, if I'm able to, you know, spend enough within the assigned period to earn those points, you know, I will usually start, start with, you know, I mean, I have some idea of places in the world I might want to go. I don't have a bucket list. It'll often be determined serendipitously by, you know, deals. I, I, we talked earlier about anyone want to go to Cyprus. But by the same, you know, token there I've had plenty of mistake rates over time. You know, I once got a, a three dollar. Well, the, the tilt in Tokyo was offering two dollar rooms instead of two hundred rooms. Three dollars if you wanted the executive executive floor. I knew people who booked the year. Someone who had a, had a office nearby, he would stop by in the morning for breakfast, stop by in the evening for cocktails and sometimes decided to stay in the city instead of going home. He had a, he had his room. And so, you know, these things do come about serendipitously. But in terms of picking, you know, where to go, obviously. Do you, are you looking for your, you know, beach vacation, much more activity. Do you like museums? You'd be much more active. But in terms of when to go, I really like to go during shoulder season and you know, that's, you know, I don't want to go when everyone else is going. Right, because you're not going to get the best deals, you're not going to get upgrades, you're going to pay more and stand in long lines. I don't want to go to Rome when it's nothing but American teenagers. That's not why I'm there. I would much rather go to say France during the Christmas markets than over the summer when it's predominantly Americans. You're going to get upgrades, you're going to get better deals and not wait in line. And by the same token, beach resorts or you want deals at the spa or an ability to get the beach chairs and not have to Stick your book out on a chair at 8 o'clock in the morning. So shoulder season is something. Where is it shoulder season? It's still a good time. I don't necessarily want to be in the middle of hurricane season in the Caribbean, but when it's not peak of peak of peak, you know, when it's not Christmas and New Year's where everyone else is trying to go and you're, you know, paying more, it's by the same token, I don't want to go out to dinner if I can avoid it on Valentine's Day. Right. When everyone's going out to dinner, all the food is pre made on sheet trays. You're paying a premium and you know, they're just trying to, you know, churn through the service.
- [44:52]
Kevin Gentry
Well said. Okay, all right, we should wrap up. But, but people need to go to your website, view from the window. Really just google you and follow you and then your recommendations of others to follow. If you're a serious traveler or if you want to plan a good vacation, there's a lot of benefit to following what you're talking about. All right, You've helped a lot of people put together interesting trips with miles points, all sorts of different things, special deals. Is there, is there a one that just stands out as really memorable to you? That, that was like. Well, that turned out pretty cool.
- [45:27]
Gary Left
Well, look, there have been a lot because I've been able to help people plan honeymoons, 50th anniversary trips. I've been able to help people, you know, travel at the last minute to see loved ones before, you know, sort of end of life kinds of events. And that's been really special. But you know, something that was really touching to me, the very first customer that I had for an award booking business, what I was doing, basically acting as a travel agent, only using miles. The very first paying customer I had, you know, was people who used to contact me and ask for help and I would help them. And I had finally decided I, that I was going to charge for this. And mostly because people often wouldn't even appreciate like I do it for them. But I learned that when you charge them, they're actually valuing it more than if you're giving it away for free. And you know, and I felt like, oh, maybe I'm not always getting the appreciation when I was doing it for free. And so I, I was contacted by these folks and I offered them the service. They thought this was great. I got them exactly what they were looking for. It was for business class tickets to Europe to meet up with a cruise exactly when they needed to go with the miles they had. And they thought that this was amazing. And so I didn't ask them for this, but they, unbeknownst to me, wrote a letter to the editor of Conde Nast Traveler. And that's what prompted Conde Nast to secret shop me at this and write an article about me every year after year after that in their World's top Travel specialists kind of Rolodex. And it was just these folks who appreciated me and wanted to share that experience unprompted. And it meant so much to me because I didn't even ask and I didn't even know until I later, you know, saw this letter published in, in their magazine and then heard from folks there, well, that's what, what prompted. Because they had never heard of such a thing and they sounded interesting. So it was just a, something that was done very generously towards me, you know, and I try to be as, as generous as I can be. Look at me. I answer questions from readers all day long. I mean, I try to answer every email and in any of the things that I've done, I always try to make sure that whoever is engaging me in anything that's fee based, they're always getting, you know, viewing it as the best money they could possibly be spending or I, I don't want, you know, their, their dollars. How can I provide value to, to folks? And then that has always, you know, rebounded itself to, you know, to my benefit.
- [48:07]
Kevin Gentry
Wow, what a great, great story. Well, you, you know the story. I think I've shared this with you. Oh, maybe almost 15 years ago, my family, we did a, a safari in East Africa. We booked the travel. We used a travel company, though, to book the safaris. It was awesome. We were in some remote spot one night there about, I'd say, 15 or 20 people around a campfire, and a new couple came in. And as what you would do is say, well, you know, how did you get here? And they were for the United States, and I think they flew through like Brussels and then Istanbul and then down to Nairobi. And we kind of laughed at that journey. They said, yeah, but it was business class. We got this deal on points and miles, and it was incredible. How did you do it? Because it says guy named Gary that did the trip. And I'm like, whoa, wait a minute. It's not Gary left, is it? And they said, yeah, do you know him? I'm like, yes, I know him. I used to work with him this is crazy. We're talking about you in the middle of nowhere in, at some, some camp in, in Kenya. So pretty, pretty cool, Gary. All right, this is my, my favorite question. I like to ask and wrap up. So you've been doing this for a while. You've been doing this almost 25 years. What advice would you give your younger self if you, you could, that you would do differently based on what you started doing back in 2002?
- [49:28]
Gary Left
Look, you know, I'm the luckiest guy in the world, right? I mean, I am able to work at a nonprofit that I care about tremendously, and I can still do that. I'm able to have, you know, businesses and travel that I care passionately about that have been very good to me. I have, I have 5 million people a month read my blog and for whatever reason are interested in the things that I have to say. So I'm incredibly fortunate. So I don't know that I would change something, but I would go back and tell myself about the specific trade off decisions that I was making. So I have this tendency. I do everything myself. I'm, I'm, I. There are, you know, there's a website, sim, that's sort of similar in some sense to mine. I have 5 million readers. It has 10 million. They have 120 employees. Right. I have, me, you know, I read everything myself. People think that's like a little bit crazy. And I wouldn't do it differently because it's my voice and I have this need to say the things that I'm saying. But I would have been more intentional. I think about making the choices that brought me there, done my own business development, haven't brought in somebody else to do that and manage it. Other folks have sold their similar sorts of sites. I haven't because then I just wouldn't have the outlet I need to be saying the things that I say out into the world. And so I don't think I would have made those decisions different, differently, but I don't think I made the decisions that I made especially consciously. And I think that I would, you know, be much more intentional along the way had I realized what I was doing kind of other than more seated pants.
- [51:25]
Kevin Gentry
Well, you're a great example of going big. The whole idea behind this podcast, to inspire others to think big. It's extraordinary. I remember you've told the story about even, you know, how you first discovered airline travel because of necessity growing up and how you viewed that first class cabin. I'd love for you just to share that. And then Conclude with what advice would you give to listeners about how they should think big and go big?
- [51:53]
Gary Left
So, look, I grew up, my parents were divorced, I lived in New York, my father in California. So I was a frequent traveler as a young child. I would travel as an unaccompanied minor, 7, 8 years old. And it was always exciting. And this was. I'm old enough now is back when people dressed up to fly, you know, still. And I just, I remember, you know, this is even at the very advent of frequent flyer programs. And I, They. They didn't even have upgrades yet when, you know, 1981, and they didn't have status, I should say. And so I would be sitting in. In. In economy. And I remember looking at this idea of first, first class. Never occurred to me that I would ever sit there, right? Because, number one, I'd never be in a position to pay for such. I had no idea. I'm like 7 years old. I have no idea what it costs, right? I'd never be in a position to pay for such a thing. But even if I did, I pay so much more money to get to the same place. This would never be me. And I never saw myself as somebody who would travel the world. Although when I was five, I had an uncle and aunt who moved to Australia. And so that became where I probably traveled the most. But, you know, growing up, it would be, of course, in back of the plane, right? I, you know, remember flying American Airlines when they flew the last time to Australia, DC 10 via Honolulu. And you just, you know, luck out and you get like a couple extra empty seats and go to sleep curled up across them. But I also remember flying in, in economy with every seat taken in the cabin. And this is before you had streaming entertainment or personal, you know, TVs. The only, you know, movie on the. The plane was King Ralph. It was like, this is on this. This trip and, and, you know, John Goodman. And they kept playing it over and over and over. And I think I watched King Ralph four times and it like, you know, pull my hair out. And you know, what for me, you know, paying attention to these things did, is it opened up the world. You know, it meant that I could go somewhere and not see it as the only time than I'd ever go. And I would, you know, I wouldn't have to try to pack everything in. And so the trip would be more enjoyable. If I felt I didn't get enough of it, I'd go back. There was so much less pressure on an individual trip because the world really opened up, but it also allowed me to open the world up for people that I cared about. You know, I mentioned family in Australia, my uncle moved there, my aunt. They had kids, their kids have had kids. And you know, my late grandparents would travel there to see their grandkids and, and kids. Right. And it got to the point where, you know, they were old, it was a difficult journey in economy. They could actually afford to travel in business class. But they grew up in the Depression. It just wasn't the kind of thing that they would do. They never saw themselves as the people who would spend that, you know, money in that way. And so they just wouldn't make the trip because it was too arduous for them and they wouldn't buy that. But I could use my points to send them in first class and then they would actually go. And so I remember doing that, sending my grandmother on a trip in first class that she never would have been able to take to see her son and grandkids and how meaningful it was to be able to do that for people that did things for me. And so I guess my view is on that it's been not just good to me as an outlet for my voice, but it's genuinely as a consumer, consumer of the, of the programs is that they've opened up the world for me and for the people that I care about. And that's what the. They do really well. Going big for me has been opening my eyes to the world of what's possible in the world and be able to, you know, see things and get on a plane and, you know, go wherever I want to go or need to go and not have it be a stressful or limited experience and then to see the opportunity to keep a job that I care about because I care about it and also pursue something else to take to make the most of every moment. Now for me, a real turning point. I used to have this long commute. I used to live in South Alexandria and I'd go to work in Arlington and It would be 50 minutes each way. And then I moved a 10 minute walk from work. And so I was saving a good hour and a half or more of commuting time every day. What am I going to do with this newfound time time? And I really put it into driving on, you know, the, the endeavors that I had in travel. And I think that's what really sparked the growth is you have, is taking, you know, this newfound time. But I also realized that I have a lot of time and you know, and you're choosing intentionally what to do with it. Well, for me, because I have a passion. It's not giving up the, you know, leisure time. It is leisure time. It's what I want to be doing. There's not a difference between, you know, work and non work. But I get up in the morning and I want to, I want to both be doing, you know, my day job even. It's, you know, 4 or 5 o'clock in the morning, drinking my coffee. But also, you know, reading about and writing and doing this. And so, you know, I'm not one of these folks that would be on that D.C. metro, you know, maybe reading the free paper, maybe listening to music, probably not just staring out, you know, you've got this one life. Let's just like make the most of it, see the world, you know, make, make a go of, you know, of whatever the passion or opportunity.
- [57:27]
Kevin Gentry
Well, thank you, Gary. And what a great story too, by the way, the origin story. But Gary Left Googling View from the Wing is his blog. You'll learn a lot. You'll benefit tremendously. It's been great having you with us today, Gary.
- [57:40]
Gary Left
Good to be here, Kevin. Thank you for having me and good to talk with you.
- [57:44]
Kevin Gentry
All the best. Thank you. Thanks for listening to today's Going Big podcast. Hopefully you were inspired to go big, big for your cause. Remember, this is all about transforming your effectiveness by 10xing your fundraising. If you enjoyed today's episode, be sure to subscribe or leave us a review at iTunes, Spotify, iHeartRadio or wherever you listen to podcasts. You can also catch this episode on YouTube and also there are lots of resources available to you at my website, which is 10x, that's t e n x strategies dot com. You can sign up also for our free weekly fundraising tips. This is all about helping you get to the root causes of some of the biggest problems in society today by transforming your fundraising and your effectiveness. Thanks again. We'll see you again soon. Bye.