The Points Guy: Growing a Side Hustle into a 140-Person Business

24:48Were you ever afraid to reinvest that money back into the company? Was there a part of you that wanted to save it, to put it into a 401k, to just call it good? No, I knew I had to reinvest it because I mean, and I didn't even know how to spend it. I was making six figures a month. You know, it was like when you're making 200K a month, it was, I didn't, I don't even really know what I was doing. And I bought like a used BMW when I could have like gotten a fancy new car. I was still like pretty, I rented an apartment. So I really knew what I wanted. I was reinvesting in it, but the amount that I was investing was so small, you know, like it was like a rounding error.

25:23You know, even hiring a couple more freelancers for a thousand or two, there's 200K a month coming in. Like that 1500 and an invoice from a contributor wasn't really. but then we started to invest more and more but then that's when i sold it it was may of 2012 that bank rate which was a publicly traded company they owned creditcards.com i was not even on the market to sell my company but a friend who knew the ceo bank rate was like you should meet tom evans and i was like i'll go in and meet this guy in madison having this stuffy office and like the next day he just texted me hey brian great meeting i want to buy your website and it was like come on It's only been profitable for a year.

25:59I did it myself, so I didn't even have bankers. I negotiated my own exit with a great team of attorneys, but I never even had to pay a banker and I had no investors. So for me, that was my taking money off the table. And that's when I got Goldman Sachs advisors day one, invested most of it. I put a lot in private equity deals that I knew I couldn't even take money out if I wanted to. So I still had to work. I was very much like, okay, I hit this good and I want to be smart. Now, that process, I think Goldman was charging me a point and a half, which was ridiculous in hindsight, how much they were charging to basically put my money in their own specialty products, which I'm sure they made quite a bit on.

26:39So my advice to people who exit, don't just go for the most expensive financial advisors. There's plenty out there that will do it far cheaper. Would you do the same thing again? Put your money in private equity using a team of Goldman advisors? No. I would, frankly, I sold in 2012. If I would have just put my money in index funds and called it a day and focused on, I'm still in Goldman PE funds and it's 2024. And the PE funds make it actually really hard. They did well over time, but it's almost impossible to calculate the return. And when I invested in them in 2012, they were all like, yeah, six, seven year return, then you'll get it all back usually.

27:19Right. But I truly, there's a not insignificant amount of money still tied up in all these random funds that have no due date to get returned. So luckily I don't need that cash. But if things would have turned around eight years ago, I would have lost my job. The points guy got acquired again in 2017 by another acquire red ventures. I'm still on with them. But there are many things where I'm like, I've been fortunate to not have to access that capital, but I would not recommend to a young founder to just tie their money up in illiquid assets with like unclear returns, like keep it simple is my advice.

27:52And you could probably manage most of it yourself. You know, it's the financial advisors have helped over the years, get apartments financing. They make your life easier, like when you're with the bank, but, you know, paying over a point is ridiculous in my opinion. What has the experience been transitioning from running the company that you founded to working for the company that you founded under a different owner? I think I have one of the most unique experiences out there because I started it, sold it in 2012 to a publicly traded company, Bankrate. But they, at the time, the points got was like this niche tuck-in acquisition.

28:28It didn't even make their financials, but it grew wildly. We had about 40 employees, and then in 2017, we got acquired Red Venture. So I have sold twice, basically, because I was CEO up until 2020. So I had to do the transition into this publicly traded company, but they let us do whatever. They got us our own office. We had Frenchies running around. We were like the startup part of this kind of stodgy financial content company. And then in 2017, Red Ventures, which is an amazing performance marketing company, they came in. I mean, we had no tech people on the Point Sky in 2017 when they were great at content, social, brand.

29:11We had built this loyal audience, but our website was literally cobbled together, like duct taped together. We never had tech help. We wanted to create an app that would actually work. So Red Ventures came in and helped revolutionize the whole backend. And they're very good marketers. So I had to do two transitions with the company into different cultures. You know, Red Ventures based in Charlotte, North Carolina has been fascinating. In 2020, I realized my skill in life is not managing 100 plus people. That was not for me. And it was just kind of one of those things where I just did it for so long and I'm proud of the brand that I built.

29:49But I was miserable. Like I was traveling nonstop. The company's expanding. Plus, you know, the demands of me being in front of the camera doing as much press. So it's like, you know, it's just I was burnt out. And the pandemic for me was like, oh, my gosh, I actually was not able to travel. I, you know, went home. I actually got to spend time in the beautiful house that I have that I never actually spent time in because I was always traveling. That was like the conundrum of the silliness of my life is I have all these beautiful friends and family, but I was just always traveling. So it's almost like I was addicted to travel to addicted to just being busy.

30:22And then I had that moment, you know, and that's when I realized I wanted to be a dad. I started riding horses. I spent more time with family. I just like spent time reconnecting with the things that I never had the time to realize that I loved. So the pandemic for me was a very special time. And I went to Red Ventures and was like, I don't think I'm supposed to be managing people. They're like, Brian, we've been waiting for you to say that. And I was like, wait, it's okay for me to switch my roles? They're like, yes, you're so talented. You don't have to be the CEO. There's plenty of people that can manage these large and ever-growing teams.

30:57You can be you. You can be our core voice in media. Do more of that. And that's been really fun. And of course, it's vulnerable to when you all of a sudden you're not in those strategy meetings all the time. I mean, I can still join whatever meeting I want. I'm still on our Slack, but not being so obsessed with the day to day. It's been a transition, but now I think I've really finally like eased into it, especially since about a year and a half ago, I had a baby. So figuring out my new normal, I turned 40 last year. I had a baby. I'm in this new role at work where it's not about just doing as much every day, but it's doing like more quality.

31:35So it's kind of like getting back to the basics, like creating content, coming up with new avenues for the point sky, potentially doing a TV show we're exploring. So it's like really exciting things for me to push myself in different ways. And 14 years after starting the site, two different acquisitions, I keep asking, like, I'm still here, but because I'm still at the core level, so proud of what we do. And we help people save money. We help people travel. And I do believe people are better people. Your life has changed dramatically from your epic trip around the world. So in this divided world where everything is so divisive, I just, I do know deep down that the more people travel, get out there and you realize that humans, we are one human race.

32:19This other ism we have with everything. You're like, you know, like just those moments where you're like, you can be in Cambodia or Johannesburg. Like people just love a good meal. People love to dance. People want security. Like we have so much more in common. So being a facilitator of that, I think is like such a huge honor. That's beautiful. I have two other questions from behind the scenes and then we'll turn the topic to two points. Let's give the people what they really want. The two questions that I have from behind the scenes, one is when I hear you describe your role, particularly in those early days, 2011, 2012, it strikes me that you were doing a lot of relationship management, right?

33:01You were going and meeting with the banks. So a big part of your role was managing relationships. A big part of your role was managing and growing the content side of the business, which especially in the early days means a lot of quality control when people are writing in your voice. You need to make sure that the content is quality and reflects the brand. And so there's the part of you that is the maker. There's the part of you that's the manager. There's the part of you that's the relationship builder. There's the part of you that's on press tour, being in front of the camera. And I guess microphones were not quite as popular back then, but giving all of the interviews.

33:44How did you balance all of those roles? I didn't balance it well. And I look back and I was a tough, tough boss because, you know, the team was growing. and on the editorial side that was one thing i like we had a lot of editorial directors that came from really amazing institutions but travel and points is a niche thing and i will lie and say that there wasn't conflict between i was never quite satisfied even with the quality of journalism managers like and i was obsessed i mean i was reading every comment on the site and like and I would get DMS and I've sure it annoyed my employees. I know it did in the aviation world.

34:24If you're talking about a certain airline and then the creative team, which is if they're not points people and they put a picture of a plane, that's different. That's bad. That was happening a lot. So it was playing like whack-a-mole and that was more just like there needed to be more of the points people. So that was always the hard point balance. Cause there's just not that many top level journalists who get this niche world. So that is always going to be a struggle. You have to grow. and also like it can't just be like white privileged male perspective points guy like i always knew we had to expand this so we acquired one of the fellow bloggers mommy points summer hole she's still with the points guy today but she had a point all about family travel so we i knew we had to expand it but people come to expect the points guys like in the know and i love that because we really did build this and still have amazing experts from cruising gene Sloan, who's like the top cruise writer in the world.

35:16So we did it right, but it was always challenging. It was always, I think there was always like heartburn around people wanting to make me happy, but me being so stretched that I couldn't give them the time. And of course, scaling any business, you have to trust your managers in the ground. So I was a Spanish major in college. I was an assistant buyer when I first graduated, got into HR, then went to the bank. So So I did not have a management degree, business degree. So I went from being, you know, individual blogger to like media CEO of one of the most profitable media sites out there. So it was a challenge for sure.

35:55If I could go back and do a lot of things over, I would absolutely carve out even more time for like getting teams together. And people always said they wanted more time with me. So being a little bit more thinking about my time and how I used it, I probably should should have reallocated, traveled a little bit less, spent more time with the team. Because when we did do those, you know, I had the whole team out to my house in the country one year for Christmas, you know, our holiday party, which was amazing. People still talk about it, like just getting to know people more. Because I think when people really know each other, you can trust someone more in a work environment.

36:29So it was a struggle. I look back and I'm like, it was a really fun run, but, you know, I'm definitely in a role I'm more supposed to be in now. Right. And then the final question, what were the most important no's that you said? What were the most important decisions to not do something? Well, I think there were very tempting times to just start writing viral content, you know, and we dabbled with it for a little bit, but I just didn't sit right, you know, because they're in during the BuzzFeed days, you know, there would be like a cocktail bar in the Bahamas where you can swim up with margaritas and sharks, right?

37:09Like that's what the algorithm was favoring. Plane crashes, negative things would get a lot of traffic. But what we did and when Red Ventures took over, we actually got a lot more analytics. So I think by paying attention to analytics and not using the metrics everyone else uses, like social follows. Like we all know there's so many accounts with fake followings. So like looking at engagement, like I was fine with this, not having a million, uh, Instagram followers if our content was really good. So I think during that whole viral craze of like deciding not to sell the soul of the brand just to spike our traffic.

37:48Cause I remember thinking, um, all the darlings, refinery 29 vice Buzzfeed, bam there. But the funny thing is I knew at the time, I'm like, we're making more money than all of them. Like we've been profitable. So it's like, yes, it's tempting to have vanity metrics, but like just focusing on the core and really just going back to just being deeply attuned with all of our advertisers and knowing them all personally and spending time with them and going to events with them. And I would do stuff for them even when they couldn't pay us or their, you know, times when I probably should have been punitive to our customers, like if they are clients, like if they dropped our how much they're paying us.

38:25But I had like long-term relations that I still have today with them. And I think you build those strong trust-based relationships. They stayed with us through the pandemic. And so I think that just taking the long-term approach, that's the biggest thing. Like turning down the temptations to hop on those short-term trends that you know are not in line with your brand can be very challenging. If you're someone who's been meaning to get a real handle on your retirement plan, I want to point you to something that I think is genuinely worth your time. Bolden. It's a modern retirement planning tool that takes all the confusion out of figuring out your financial future.

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41:11turning our attention to points so to uh to people listening actually let's first sort of address the the elephant in the room you've touched on this you have a baby a 16 month old dean kelly he's been to i think 13 countries we're about to do three more in the next couple weeks He's the best thing I've ever done in my life. He is my mini me. He loves travel. He eats everything. He's like in the 90th percentile, like height, weight, head. I'm six, seven. So for people who know me, and he's just a joy. Like he, and I've started day three. We flew home from the West Coast because I had him via surrogacy as a single gay dad.

41:54I made the decision. I've always wanted to be a dad. So during the pandemic, I started the process. I was like, my dating life is non-existent. I'm like, hold up in the countryside. But I'm like, who says I can't have a kid? And I have some friends who have done it. So started the process, had the most amazing surrogate, changed my life and healthy baby. It's just been such a game changer for me and still being able to travel. In full disclosure, I have the most amazing nanny in the world. I got a nanny who her kids are all grown. She's divorced and she's like, let's go. She hasn't traveled the world, but she loves my son.

42:29She loves me. We're like a little family. Truly, even when my son's sleeping, I hang out with her and we talk about life and she meets the guys that I'm dating. So it's like this really, it's fun. So I'm in a really good spot. Granted, I'm single, so I really do need the help. I'm not going to try to paint it that I'm doing this all solo because I'm not. But traveling and now seeing the world through his eyes. I just took them to Tokyo last week and Disney parks in Tokyo are incredible. And by the way, so cheap. It's like 50 bucks a ticket and the food's amazing. Have you ever done like a Disney Tokyo or?

43:06I've been to Tokyo twice, but I've never gone to Disney. It's like 25 minute Uber from Ginza. So easy, so clean, so orderly, great snacks are known for their popcorn. So Disney Sea is the really unique one. And all I'll say is like I took him on his first ride and Triton's kingdom is like Little mermaid themed underwater. And he sat on my lap in a little jellyfish as we popped up in the air. And when he went, Ooh, I just like, I just almost started crying. I was like, this is it. There's nothing sweeter than like now getting this, even though people are like, he's not going to remember it. But I'm like, but I, well, you know, I remember that moment.

43:42So it's amazing. Wow. Wow. What would you say to people? There are so many people who say, well, I have kids, so I can't travel or I have kids, so it's harder to travel. Yeah. I mean, look, I'm not going to lie, especially when kids are in school, you're locked to school schedules. And a lot of those weeks, it's expensive. I also, I have frequent flyer miles. So we fly first class and even going to Tokyo, we had the New Japan Airlines suite with the closing door. So even though my son decided not to sleep for nine hours, having this first class suite where we're laying down, playing toys, coloring book, it's amazing.

44:15And I realized how privileged I am, but I pay less than a coach seat for that. So what I'll tell people is if you play your points right, you can fly in business class. It's a lot better. I wouldn't be going to Asia and economy with my son. I'll be on it. But when you have points and can fly, and I fly my nanny in business or first class with me, so that's a help as well. It makes it so much better. And you don't need to be rich to do that. And infants until two years old, they fly free domestically. you have to pay 10 % of the ticket price when they're, which for me going to Tokyo in first class, it was actually$2 ,300 to bring them on my lap, which was insane because it's a$23 ,000 paid ticket.

44:55So they put the price of like what a paid ticket would be. But most of the time you're paying it like even a business class, a couple hundred bucks, but yeah, so it's really just all about the points. And, but there are loyalty programs out there. Um, arrow plan air Canada's program, which is one of the best loyalty programs out there. You can transfer Amex chase city, built points, they only charge 20 bucks to add an infant to any seat. So that's actually the best program. If you're using points from your credit cards, transferring to Aeroplan and adding an infant is$20. You don't have to worry about hundreds or thousands in fees.

45:28So on that topic, there's a lot of information out there about how to accumulate points. The internet is saturated with accumulation because that's where the money is, right? The money is in conversions and getting people to sign up for credit cards. There's not a lot out They're about redemption. Yeah. And that's when so many people get tripped up. So many people are points hoarders. I know. Guilty. Guilty. Guilty. I have points psychic ability. I can sense it from her. Okay. So the beauty of this. So yeah, it is tricky trying to find how to use your points, right? And so just back to earning, I will just say, while the airlines are increasing the amount of miles needed to travel, like 10 years ago, you could go for 100 ,000 points on most programs.

46:13business class to Europe. That's not, at least with the U S programs, you're looking at two, three, 400 ,000 points. So some people will say, Oh, the inflation in points, it's not even worth it anymore. I rebut that because there's now so much competition that you can get a hundred thousand points, signup bonuses left and right, just for getting a card. And then plus the U S is the, the, the golden goose of global points that you can earn so much by making sure you use the right credit cards for the right expenses. Like so many of my friends have the platinum card by Amex. Great card. I have it.

46:45You can get into lounges, but it's really not the best for points. It's a Perks credit card. I only put my airfare 5X on air from the platinum. You want to get the gold card by Amex. It's less than half the annual fee and you get four points per dollar on all dining and groceries. So when you start getting 4X for dining and groceries, triple points for travel, parking tolls, you know, built is a new credit card. I'm going to help to found that company, no annual fee, no fee in paying your rent. You get up to 100 ,000 bill points a year just by paying your rent. And it takes it out of your dev account.

47:19You're not going to go into debt paying rent. It literally pulls it from your bank account as if you'd cut a check, but instead you earn points. It's an absolute no-brainer. Especially in New York. It's an absolute no-brainer. Even if your landlord only takes check through bill, you can actually cut a check to your landlord and still earn points. Absolute no-brainer. So the goal is to maximize every dollar you spend and get cards that really reward you for that. So you're getting some signup bonuses here. So all of a sudden, it's really easy to get points. And what I recommend, get transferable points so that this is like the points that you accrue with a credit card company are better than just any one airline or hotel.

47:57I know so many people are like, oh, I fly Delta or American. They'll come to me and be like, oh, I want to fly Emirates to Dubai. How do I do that with my 3 million American miles? I'm like, you can't. You know, you can fly Qatar Q suites if you can find it. The goal is to accrue into these transferable programs so that you can transfer to all sorts of partners. That's where the real value comes in. The only reason I have like the co-brand airline hotel cards is for perks. So free check bags. If you need elite status, it can make sense because all those cards now give you elite perks. But if you don't care about elite status, even if you want the free check bags, have an airline credit card, but don't put all your spend on it.

48:35only spend on cards that give you transferable points. There's one thing you take from this whole podcast. Make sure you have a transferable points credit card. That's going to give you the maximum flexibility. Back to redeeming. This is where most people trip up, where they log on. They'll get overwhelmed with choice and they go away. So the exciting thing I have to share today is that there's so many new tools. There's a bunch of different websites I'm going to recommend. And the first one is seats.aero. Seats.aero is this incredible tool. And what it allows you to do as a pro member. So tonight, I'm actually flying Emirates first class from New York to Milan.

49:16It's an$8 ,000 ticket. And it's only 100 ,000 Emirates points if you can find the availability. So seats.aero, it takes a little bit getting used to. There's blog posts that will explain it. So what it does is there's probably 15 different loyalty programs. You can choose Emirates. And you can filter over the next year and you can write Emirates nonstop flights from JFK to Milan because they fly from New York to Milan and Athens and as well as Dubai. So you can put JFK to Milan nonstop and then you can sort by first class. And this is the A380, which has the onboard bar showers. And it'll actually just show you all the dates in 2024 where you can instantly book for 100 ,000 points.

50:01So this is why if you have Chase points, Amex points, Capital One, you transfer 100 ,000 points to Emirates for first class and$8 ,000 ticket. Right. And a lot of times they'll only have one first class seat, but they have much more business class and it's only$100 in fees. Well, and even if you have a co-branded card, you could still search for that. Correct. So United. So say you only have United points. So you want to go United from JFK to London to visit family. you can actually go in and then search for business class availability sort. But here's the thing. The U.S. frequent flyer programs are the ones you do not want to put all your eggs in their basket because they're raising the amount of miles wildly.

50:43They're all what we call dynamic pricing. Here's the trick. You want to accrue points in these transferable points programs, and then you transfer them to foreign frequent flyer programs. Because in France, for example, they don't have the credit card offers we have in the U.S. So they still keep their redemptions at 50 ,000 points each way for business class because their French customers can't earn the bonanza that we do in the U.S. So if they raise their redemptions to 400 ,000 points, they would literally have a mutiny because French people would be like, we'll never, ever be able to redeem.

51:16So these foreign programs have to keep their prices low for their local customers. But in the U.S., we can earn insane amounts of points. So here are the programs that Air France Flying Blue is one of the best. I mean, you can fly business class on KLM, Virgin, Delta for 50 ,000 points each way. And by the way, 50 ,000 points in a cash back program is 500 bucks. So what I'll say to you is, would you rather have$500 or business class to Europe one way? Most people would probably say business class. And by the way, if you want cash back, that's totally fine. But just make sure you're getting at least one and a half to 2%.

51:51That's like the gold standard. So many people will use an Amex Platinum and then try to use those points for cash back. and you're getting less than 1 % value back. So if you want cash back, do not use Chase, like Sapphire, Amex, Platinum. Those are travel cards that are best reading for travel. Get a Citi Double Cash, Chase Freedom Unlimited. Those are the best cash back cards. But don't try to take a really valuable currency, like Capital One Venture, and then try to turn it into statement credit. You lose so much value. So each of these credit card ecosystems are better. If you want Amazon, get an Amazon.

52:27card. Using Amex points for Amazon credit is horrible, horrible. You're throwing money out the window. You want to align the credit cards that you have with how you want to redeem. But so Seats.Aero is an amazing tool. Say you want to go to JFK to Milan, there's no seats available. You can actually create alerts for certain weeks and they'll text you. The minute Emirates opens up a seat, you'll get a text. You can snag it before anyone else. So this is how points experts are playing the game because the airlines, they open up award seats up until departure. So even if you're flying, say you want to go to Dubai, but you have to stop, let's say Frankfurt, because that was the only thing you can get.

53:05If the nonstop opens up, you can just change your award for free to the nonstop. So this is where loyalty programs actually allow you to change flights much easier than when you pay for a ticket. Because we all know when you pay for a ticket, you want to change it. It's change fees. It's repricing the fare. You always get hosed. The loyalty programs, especially over the pandemic, they relaxed all the rules. So once you start having points in all these different programs, you can book multiple trips. Like if I really need to go somewhere, sometimes I'll have a backup trip planned in case the one flight gets canceled or delayed because you can cancel up until departure for free and most frequent flyer programs.

53:42So if there's weather impacting your flights, you think your flight's going to get delayed. My first thing, I just book a backup on a different loyalty program. And then if I need to use it, great. If not, then I just cancel it and get all my miles back. Wow. Other than Seeds.Aero, are there any other websites that you recommend? Yeah, so roam.travel, R-O-A-M-E.travel. And they're great. You can follow them on Instagram and they post all the amazing flight deals that come up. Point.me is another one of these. Oh, I've heard of that. Yeah, they're pretty good too. Expert Flyer is another tool that's been around for a long time.

54:18Expert Flyer will also let you do seat alerts. Like say, if you book last minute, you're in a middle seat, you can actually set alerts if an exit row opens up. So these tools, I think, really do change the game. So you want to book as far out as possible. Give them at least so you can set alerts so that when the best availability opens up, you can change and kind of find the best availability. Also, I'll say just when buying flights, everyone listening, you should be aware of Google flights. So Google.com slash flights is where you can sniff out the cheapest airfare. They have a really cool feature most people don't know about called Explore.

54:51So say you're in Chicago, you need to get away in March. You're like, I need a beach trip to the Caribbean. You can put Chicago to the Caribbean, you know, weekend or week in March, and it'll reverse engineer and show you all the flights to the Caribbean from Chicago so you can sniff out the cheapest flights. So instead of having to search one by one or what I tell people is just go where the deals are these days. Never been to Anguilla? Well, if it's the cheapest flight, go. So, you know, Turks, sometimes like I love Turks and Caicos and often like that's the cheapest flight to the Caribbean.

55:24And then there's aways.com. A-W-A-Y-Z.com is for hotels. So say you have Hyatt points, which are some of the best points out there. And you want to stay at, let's say, the Park Hyatt Kyoto, which is probably the best Hyatt out there. Everyone is obsessed. Everyone I know has stayed at the Park Hyatt Kyoto. It is the points hotel of the moment. That was the one that was made famous by the movie Lost in Translation. That's Park Hyatt Tokyo. Oh. Yeah. So Tokyo has always been amazing. That's actually about to undergo a two-year renovation, which it needs. But Kyoto is the brand new Park Hyatt. I didn't get a chance to go this past trip.

56:01Everyone I've talked to, my snobbiest of snob friends say the Park Hyatt Kyoto is where it's at. But it's$2 ,500 a night. But you can get it for 45 ,000 Hyatt points. So you can use aways.com to sniff out hotel of all the top hotels out there. If you want to say the park high of Paris, it'll actually give you calendar views so you can sniff out the best deal. So I say plan your trips around where you can see the availability and all these resorts. And so once you start using these tools, it all gets much easier. And so if you're listening, you're like, that sounds like a lot of work. Let me just put it to you this way, like points game, the points game.

56:37Like once you get the hang of it, when you start saving thousands and thousands of dollars, when you're flying these first class where you're treated like a king up in the air, You know, tonight I'm flying, it was a hundred dollars to fly JFK to Milan and a hundred thousand points. And I'll have unlimited Dom Perignon. Emirates has unlimited caviar and I'll take a hot shower before I land in Milan for$100. How many people on that flight are jammed in a middle seat and coach who paid a thousand? Right. So yeah, it's a little bit annoying sometimes, but I'm telling you for the people, if you want to take 10 minutes of your day for a couple days a week and start to pick up this, I can assure you, you will thank yourself for spending a little bit of time to dramatically change the way you travel.

57:17That is the perfect place to end on. Are there any final messages that you want to send to this audience? Well, I would say just follow me on Instagram at Brian Kelly. That's my personal account. I just started doing flight reviews with my son. We flew the New Japan Airlines first class. That just crossed a million views. That's my first million view video. So I think Dean and I are going to be doing our flight reviews of fancy hotels and stuff. And then at the points guy is our brand account and the points guy.com. And if you want to stay up to date, we have a daily newsletter. And then I write a weekly newsletter for the points guy where I cover my personal travels.

57:56I'll give my spin on everything going on in the industry. So if you just Google, like sign up for the points guy newsletters, highly recommend. And we'll put links to all of that in the show notes as well. Awesome. Thank you so much for having me. Of course. Thank you for coming and chatting with us and enjoy your flight to Milan. Oh, I will. Although it's harder to take advantage of the champagne thing when traveling. I feel a little guilty. Like I'll have a glass or two. Got to get my money's worth.

58:23Thank you, Brian. What are three key takeaways that we got from this conversation? Number one, start a side hustle. Brian started a side hustle that grew into a 140-person company. He was making$65 ,000 a year during the Great Recession. He was in credit card debt. He started a hobby side hustle, and it exploded. and it's an absolute testament to thinking big, to grit, to determination, to knowing and believing that the side hustle that you're going to start is more than just a few extra dollars here and there, that this is the beginning of something absolutely life-changing, not just for yourself, but for all of the people that your business impacts.

59:13Part of starting a side hustle and growing it and scaling it includes having a really rigorous assessment of what your skills are and what your skills are not. Brian himself said that there are certain elements of his business that he was quite good at, like working with people, building relationships. And there were other elements of his business that he knew that he was not the strongest at. And so he learned to delegate out his weaknesses to let other people who were good at those things take over those elements so that he could stay within his strengths and he could work within the realm of his own unique abilities.

59:57I started it as a fun blog in 2010. Just it was kind of a side hustle. You know, I would charge people 50 bucks to help them use their points. So I was like a points travel agent. And the blog was just supposed to be my organic, you know, advertising to get people who might be searching for how to use Amex points. Let me stumble into this website, the points guy. And then they would email me here are the points I have helped plan my trip to Paris. So that was the goal for the site. Never in a million years did I think, you know, I would eventually sell it to a publicly traded company and we'd have 140 employees and growing globally.

1:00:33I realized my strength is with people and senior executives. And the banks liked me, you know, and I was charismatic and I was able to talk about points and loyalty in the press when the narrative at that time was frequent flyer miles are useless, blackout dates. And I remember reading in mainstream media, every, every columnist, they just didn't do the work. They were like, oh, I called once and I couldn't get a flight. Therefore, points are useless. I've always taken a long-term approach, and I think that's what has allowed me to go from just being a blogger to creating something that we launched credit cards with the credit card companies.

1:01:10In 2016, Chase chose us as their launch partner for the Chase Sapphire Reserve, which broke the internet. Having a long-term strategy, I think, has helped grow the Points Guy into something that, in my wildest dreams, I never thought possible. And so that is the first key takeaway. Key takeaway number two. Many people dream of starting a business and having it take off and produce enormous success. I mean, who among us doesn't dream of that? But the reality, the daily reality of that is that that requires that you face your demons. And there are going to be challenges that are both external and internal.

1:01:51There are going to be people who are jealous, who want to see you fail. There are going to be people who disparage your success or who try to diminish it. There are going to be people who patronize you or who talk down to you and try to make you feel inferior or insecure. There are many times in which your success may trigger the insecurities of others and you need thick skin. You need self-assurance and confidence to be able to withstand that. And a lot of that comes from having a strong internalized sense of mission, of purpose, and of living inside of your own integrity that allows you to fuel a strong internal locus of control.

1:02:36Now, in addition to that, and as part of that, you also have to face your own inner demons. You have to face your own internalized fears, doubts, insecurities. Brian talks about how going to therapy was transformational for him in teaching him how to have the fortitude to be an entrepreneur. I've gone through years of therapy and I would recommend any entrepreneur, anyone in life needs therapy. I think it has helped me dramatically take a step back and be confident and know what I deserve and know the boundaries, you know, the non-negotiables, people who creep into your space and make you feel bad.

1:03:17And as you get older, you realize I don't need to allow that to happen. And as you start plucking those negative forces out of your life, my life has gone up so much quicker. No one really prepares you for it. And my success, I look back, it kind of like was winning the lottery. It was from zero to 100. I was living paycheck to paycheck, even though I was in HR at a bank during the Great Recession. I was making$65 ,000 a year. In New York City, I was literally paycheck to paycheck. And I was done with credit cards. I was actually in credit card debt. So it's like, I was on the hamster wheel. And then bam, this took off.

1:03:50Becoming a successful entrepreneur means that you must grapple with your unconscious ideas, your limiting beliefs, because those beliefs can lead you to self-sabotage. They can lead you to hold yourself back. And so grappling with those often unconscious limitations that you impose upon yourself, that is a huge component of achieving success in any domain of life, whether it's business or whether you want to reach an early retirement, whether you want to go travel the world, you want to start a nonprofit, whatever it is that you want to do. Grappling with your internalized limitations is imperative to achieving a growth mindset, which then helps you catapult to that next level.

1:04:38And so that is key takeaway number two. Finally, key takeaway number three, and this one is far more straightforward. word, there's a lot of information about how to accumulate miles, right? There's a financial incentive for people to share information about how to accumulate miles. There is not a lot of information about how to redeem miles. And so in this third and final key takeaway, Brian shares some of his best tips on how to be smart about mileage redemption, essentially how to be smart about your spending? Make sure you have a transferable points credit card. That's going to give you the maximum flexibility.

1:05:19Back to redeeming seats.aero is this incredible tool and what it allows you to do as a pro member. So tonight I'm actually flying Emirates first class from New York to Milan. It's an$8 ,000 ticket and it's only a hundred thousand Emirates points if you can find the availability. So seats.aero, it takes a little bit getting used to. There's blog posts that will explain it. So what it does is there's probably 15 different loyalty programs. You can choose Emirates, right? And you can filter over the next year and you can write Emirates nonstop flights from JFK to Milan because they fly from New York to Milan and Athens and as well as Dubai.

1:06:00So you can put JFK to Milan nonstop, and then you can sort by first class. And this is the A380, which has the onboard bar, showers, and it'll actually just show you all the dates in 2024 where you can instantly book for 100 ,000 points. So this is why if you have Chase points, Amex points, Capital One, you transfer 100 ,000 points to Emirates for first class and$8 ,000 ticket, right? And a lot of times they'll only have one first class seat, but they have much more business class and it's only$100 in fees. Those are three key takeaways from this conversation with The Points Guy, Brian Kelly, the founder and CEO of The Points Guy.

1:06:44Thank you so much for tuning in. If you got value from today's episode, please do three things. Number one, share it with a friend or a family member. That's the single most important thing that you can do. Number two, make sure that you are following us in Apple Podcasts and Spotify and on YouTube, youtube.com slash afford anything. And while you are there, while you're in Apple Podcasts and Spotify, please leave us up to a five-star review. These reviews are incredibly helpful in allowing us to book amazing guests that we can share with you and we can share their knowledge with you. Number three, please subscribe to our show notes, which you can access by going to affordanything.com slash show notes.

1:07:27Now, we offer a course on rental property investing that we teach twice a year, once in the spring and once in the fall. Enrollment for our Spring 2024 cohort opens on May 22nd. So from May 22nd through May 31st, the enrollment window will be open. That is your opportunity if you want to join our Spring 2024 cohort so that you can learn about rental property investing. You can get lots of information by going to affordanything.com slash enroll. We will send you much more information if you sign up for our newsletter at affordanything.com slash VIP list. That's affordanything.com slash VIP list.

1:08:09Once you've subscribed to the VIP list, just hit reply and ask any question that you would like. I will be answering many of these questions on YouTube live streams in the coming days. So again, that's affordanything.com slash VIP list. Thank you so much for tuning in. My name is Paula Pant. This is the Afford Anything podcast. I so appreciate you being part of the community. Again, make sure that you are following us in your favorite podcast playing app, whether that's Apple Podcasts or Spotify or Pandora or whatever it is that you prefer to use. And stay tuned for next week when we will be running two interviews.

1:08:47One, with the CEO of Opendoor, a real estate transaction company named Ryan Johnson. And the second, with a longtime friend of the podcast, The Madfientist. So if you're in the financial independence community, you know Madfientist. We'll be airing both of those interviews next week. Make sure that you're following this podcast in your favorite podcast playing app or in several of your favorite podcast playing apps so that you don't miss either of those interviews. My name is Paula Pant. This is the Afford Anything Podcast. And I will meet you in the next episode.