668: Brian Kelly (The Points Guy) - Building a Media Empire, Crafting a Big Vision, Relentless Leaders, Hiring Well, Scaling Up, & How To Win at Travel

25:20We've got a whole talented team of flight reviewers that do these fun YouTube reviews on YouTube. We've got a team of college grads. I mean, we hire college grads who have no points and miles or finance experience for that reason. And then they can talk about getting credit cards. I'm a 42-year-old wealthy man with the perfect credit score and connection. So having the experience of someone that you can relate to, I mean, that's 101 of building an empire. so people still associate so much of the site with me when most of what is created is not just me if you look at our social media i mean i appear in videos and tentpoles but like there's tons of other spokespeople as well even in media we have i think 12 other media spokespeople now beyond me while i may be the one that opens the door for new outlets but you know we have a whole group of other people doing it as well was that hard initially because they trust you they like you They want you.

26:17For sure. In the very beginning, when I was just overanalyzing every decision, when I was CEO up until 2010, I mean, I still read comments, emails, and I wouldn't chime in on Slack when there was a mistake in an article as if I wrote it myself because I'm like, this reflects on me. So when we write, I remember so vividly, you know, in a very viral post at the time, we had the wrong capital of like of Norway. It was like Reykjavik, the capital of Norway. And I'm like, to me, as a geography buff, I'm like, come on. And people are like, calm down. it's a simple mistake but i was just like i do take the integrity of this site as we expand we can't forego quality so yeah i think that's something you always deal with but i learned pretty early on to hire good people trust them if i look back at my time as ceo i was a tough boss because as a founder i still it's so personal right it is so personal it's your baby you started it it was just you at the beginning i know this feeling very well i mean every little thing will really part of what probably has made you great is perfectionistic tendencies and very high standards and being super demanding of yourself.

27:27And so when you live that way, and if someone then is associated with you, your company, your brand, and they don't, even if it was a mistake, just they didn't mean to just make a mistake, that, yes, can be very bothersome. Yeah. But in hindsight, I didn't highlight enough of the wins. I would focus too much on mistakes. And that's advice I would give. If I could do it all back over again is to just be much more because as a, you know, as a human, we like to get, it's much more positive reinforcement over negative. And so to founders out there who are scaling, like you need to check yourself and have someone around you, a leadership team, someone that can check you.

28:07I didn't have that for a very long time. And that's my fault to have someone who I pushed to tell me the truth because I do believe I operated, you know, the business by all external metrics was booming for so many years. And I think, you know, making sure you have good people on your team that can be honest with you and you create, it's about you creating an environment of like inviting that feedback and not freaking out when they give it to you is important. And that's something I definitely would think about as if I did it again, I know I would be a much different CEO today, but. We need truth tellers, man.

28:44We all do. 100%. Whether you're a CEO, leader, or just a human, we all need truth tellers in our lives. we all think we're really self-aware. Most of us are not. And there are definitely moments when we are not even the most self-aware person. We need truth tellers. I'm curious. I know you're not hiring leaders right now, but I think it's useful to get in the mind of a really thoughtful, intelligent person like you who's built something like you've built. When you were or if you were now going to, what are some of the must-have attributes in a person to hire for a leadership role? So we are still hiring a lot of people.

29:18We have a new CEO at the Point Sky. I work with her, Liza Landsman. She's amazing. We've just hired a bunch of senior executives. We're kind of taking TPG into a really exciting new place. So I am involved in those decisions. So I interview people quite a bit and I'm not the final decision maker. They don't report to me, but we are all a team at the end of the day. So I think during the interview process, it's too, everyone is BSing way too much. I think too many people take jobs not knowing what is going on whatsoever at the company. And I think as hiring managers, we try to make everything seem pretty and we select the interviewees that are going to make it look great.

29:56But I think far too many senior executives walk into positions and they're like, oh, wait a minute. So I like to be not brutally honest. Of course, I'm still a brand person. I'm not going to completely just focus on the negative parts, what they need to come in. But I think like truth telling in the interview process is the beginning of like having a great relationship with someone because I want you to understand exactly what's in front of you. And if you don't want to take it, that's so much better than hiring a senior exec. That's six months later than you're six. You just lost a year. And for me in the interview process, it's stop telling me the wins because look, anyone can make their job look successful.

30:34Oh, 200 % ROI, this, that, the other. First of all, in an interview, you're not going to be able to fact check any of this. And we all know people can cherry pick the data that made their, it's like really just diving deep into vulnerable moments about their leadership, the challenges as leaders they had with their teams. I'll tell them my challenges when I was CEO. Like I want people to be real and allow me to understand like how they think the type of leader they are. Not just like we launched this new website and it was twice as good as the old one and blah, blah, blah. Let's say they're willing to be vulnerable.

31:08you can feel that they're telling the truth about wins losses everything in between what are some other things is it do you use your gut intuition to be like i really like her i like him yeah that's gotten me in trouble in the past i think yeah you know just obviously because the problem is very charismatic people can trick you easily right and you know especially when you're exhausted as a ceo and then you go into an interview and you're like oh and then someone's like bantering with you. You're like, oh, that was fun. Right. But the problem with that is I've hired plenty of people who are all talk.

31:43And when you dive deep, they, I don't want personality hires. I'm the personality, you know, like, or at least in certain roles and in a sales role, personality role might be higher, but like my engineering team, like I really need people to ship updates. So it's really tough. I think interviewing is one of the hardest things because you want someone to be vulnerable but um you really can't verify a lot and even with checking references nowadays you you kind of have to at the end of the day you do have to go with the gut feeling yeah i want to think about you envisioning being wealthy and having a mercedes now that you've got all that how does it feel i still wake up in the middle of the night because I'm like, are my bills paid?

32:30Because I have several homes and there's a lot going on. Two kids. I've got nannies. I've got a whole team now. I don't manage any employees at the points guy, but I have 10 employees that work for me personally as I'm building. So sometimes it's amazing though to be able to know. I still have to tell myself, it's okay. Even if I stop working tomorrow, I don't have to work ever again because I've made good decisions. And I still sometimes have imposter syndrome about it's not about the car. But I will say the homes, investing in a home that's beautiful and makes you feel really good is important.

33:05I think for a long time, I was traveling a lot. I never didn't really put roots down. And I always felt like I was in transit. And now I think I have this beautiful farm with animals and horses. I started riding horses in the pandemic. I have this farm that is, it takes my blood pressure down immediately. I can walk. I can spend time with my kids. So I think investing, and it's definitely not cheap to run your own farm. Where is it? It's in New Hope, Pennsylvania, which is a beautiful town about an hour and a half from New York City, an hour north of Philly. My family lives there. So my two brothers and parents, that's where I grew up.

33:41So having that, I think that is what I highly recommend and get a designer to do things correctly. I'm still kind of cheap in a lot of ways. So I would buy my own furniture and I'm shopping online. And at the end of the day, like hire professionals to do and make your home really comfortable, your office. Invest in the things. I think investing in a home that really makes you feel grounded is an amazing investment. As you said, you don't need to really work anymore. Why would you start something and then have to have 10 employees and go through all this with investing in others? Like, why do all that?

34:17Well, that's an interesting. So an inflection point for me. So when I stepped down, so 2020 was the ultimate year of, at the time, felt very challenging. I was engaged. I broke up with my ex-fiancee first week of March. The pandemic hit. For the first time in history of the points guy, we started losing money. We had been a money printing machine from essentially the beginning. So we're losing money. And I moved outside the city and realized I wanted just a different mentality. I didn't want to just be hustling. So kind of had that conversation. And at the same time, I had always been approached by other founders to help advise.

34:53And there was one company, The Morning Brew. They were readers of The Points Guy, and they kept bothering me to be an investor and advisor in this little newsletter. I did, and it was a 10x investment over like two years. And I helped them because what they were building was very similar to what I built at The Points Guy, a small media company built around a passion. But a lot of other people had approached me, and I just never had time. I was too busy and I didn't want to invest my money in these startups. I just didn't have the capacity. So in 2020, I wasn't working the same sort of chaotic travel schedule.

35:25So I opened up all this space where I decided that I wanted to have kids, even though I was single, which that in itself has been a journey and the best thing I've ever done, but also start investing and advising in relevant companies. And the first one that came into my lap was this guy, Ankur Jane, who was building a credit card company loyalty platform for renters. And for years, I'd always thought how cool would it be to earn points on rent. I finally met with him. He had been bugging to meet with me. I kind of put it off and it was like April of 2020. And he told me the thought process of what is now built.

35:57I said, you're crazy, but if it does work, it'll be massive. So let's do it. And he gave me a bunch of shares and that has been incredible. So built is now, you know, an$11 billion valuation and just skyrocketing and I'll make more money now probably on built than I will at the point sky, which is wild to me. And it's also shown me that I don't, you don't need to put in the crazy amount of effort that I put into the point sky now being an advisor. So I have probably about 15 other companies I put my personal money in and, and I love it because I can help advise founders on everything I've done, help open doors, give my comms.

36:35I know every influencer using that to build wealth is really angel investing has basically become an addiction i could see how when you see some of those returns i could see why it makes a lot more sense now and and not all of them i've definitely had flops you know as you always will but i feel really good that there's i mean once you have one mega one like built yeah it can make up for a lot A lot of flops. Yeah. Yes. So you spent so much time around other leaders who have sustained excellence over an extended period of time. You just mentioned a few of them. What have you found in your experience that those leaders seem to all have in common?

37:16I mean, relentlessness is the first thing that comes to mind. So Encore, I am amazed at his ability to just, you know, if he's got 10 major things impacting his business, Most CEOs will start with like wanting to put the others on the back burner. I mean, he will relentlessly push for excellence and his team. And that's why I like investing. I don't want to work for Encore. I mean, but to be in the room and to strategize and every time I leave a meeting with him and hey, let's go do this, let's go launch these new cards. That to me is exciting and it keeps me fresh and active. So back to the question of like, I could retire, but I love it.

37:56I'm a racehorse, right? Like put me in the race. I don't want to just be hanging out in a pasture, right? I don't want to be racing seven days a week, but it still feels good to like be put into a racetrack with other top and to be pushed. So thinking boldly, another one of my investments is a former intern, Michael Spellfogle, intern for me at the Points Guy in 2015. He's now the CEO of Cardless, which is one of the top neo fintech credit card companies out there. They just launched the Coinbase credit card, Qatar Airways. And now in 2026, they got the built business. So the huge built is going from Wells Fargo to Cardless.

38:32So that's a really cool moment for me as an investor advisor and two businesses that are now coming together to do amazing things. That is very exciting to me. Now I feel like I'm a part of history and that we're creating the new era of points and loyalty. Well, I mean, when you look around and see the people who have done big things and left a positive dent in the world, they're just not able to stop. Some of my friends get around like, well, man, if I did what Jeff Bezos did, I would just chill. And now he's like co-CEO of a new company and he's sending rockets and Elon Musk. And you are not able to do what you've done, Brian, the points guy.

39:08I don't think the people who are capable of doing those big things, at least for the most part, are capable of stopping. And I don't think that's a bad thing. Like you said, I'm a racehorse. I'm built to race, right? Maybe not every day, but I'm built to race. I just don't think the people who leave positive dents in the world are capable of just sitting on a beach and chilling. I just don't think that's possible. For me, I definitely have scaled back. Like I work from home. My biggest priority is I have two young boys, three years old and one. My youngest is going to be the youngest person in the world to visit all seven continents.

39:44I just took him to Antarctica Is that like in a Guinness Book of World Records? Is that a real thing? Yeah, yeah He'll be 12 months and 10 days And for years the record was 3 years old Just recently an 18 month old broke the record I'm like, well, sorry buddy So my son will be a year old Which is just like a fun thing we did I didn't even set up to do it But, you know, I love to challenge myself But I'm home I really, especially, you know, until my kids turn 5 When they really start going to school I love the fact that so much of what I'm doing, I do from home. I'm with them. I take my son to school in the morning almost every day, have lunch with them.

40:19So that to me is something that I'm very cognizant. I wouldn't go back into a full-time CEO role until I felt really good about, especially because I'm a single dad. So that's a decision I chose to have kids on my own. And I'm very aware of like, I don't want to have kids in this world as a single dad and then not be present for them. So that's pretty wild, man. Like what made you want to do that? I've always wanted to be a dad. It's like one of the universal truths I've known about myself. For many years being gay, I was like, oh, it's not possible. And then, you know, I always knew I wanted kids.

40:51But, you know, the business, I always put the business first. From 2010 to 2020, when I was CEO of the Points, got jet-setting around, sold the business essentially twice, built a brand. I put everything. I was not going to be a good father during that time. And then when I broke up with my ex-fiancee and I realized it's pandemic, it's going to take years to meet someone that I trust that I would want to have kids with. I was 37 at the time. I wanted to have kids in my 30s. So I said to myself, well, I can do this. I have an amazing family. I have the means to hire the best nannies who are my lifeblood.

41:22I could probably write a book just on nannies and finding the right one. But I'm so happy I did it and didn't wait for someone else to unlock this life dream of mine. Wow. That's wild, man. And you probably get asked this one all the time, but I'm still going to ask it anyway. Where are your favorite current places to travel? So I just recently went to Antarctica. I'm a big nature outdoors. I love being in places where you feel completely like on a different planet. So National Geographic Lindblad now has this ability to fly from Patagonia and Chile. You can fly two hours to King George Island and then get on a ship for six nights, which to me is perfect.

42:00I'm ADD. I don't want to be on a cruise ship for two weeks. don't want to cross the Drake Passage for four days straight in rough seas. So this to me was like an ultimate trip. I took my parents and my kids because the seas are not bad. Antarctica was like a wow, I get it. It was just really powerful. I also love South Africa. If you need inspiration, if you want a beautiful trip of like safari, Royal Malawan is like, I went there this year, unbelievable safari. Cape Town, wine country. It's the ultimate sort of soul refreshing trip for me. Okay. This is a projection of my situation. You got 3.3 million Delta miles.

42:41Diamond. How are you using them? So unfortunately, Delta's of all the airlines are great airline, but their loyalty program is challenging. Those 3.3 million might get you to like Dayton and back, but no, they're not that bad. Delta actually does a good job. They run specials all the time. They'll run specials like 100 ,000 points each to fly Delta One to Australia. They just launched a bunch of new routes. So I would look to see whenever Delta runs these specials. They also fly nonstop Atlanta to Cape Town and Joburg. So Redeem to go to South Africa or Australia, I think would be how I'd use those.

43:17I think you kind of have to get the lay down. That would be a rough one without it. Oh, yeah, yeah. Do you still fly commercial? I do, actually. and i'll charter here and there but it's still i'm still a deal seeker so it's just it really rarely makes sense unless i'm flying short distances around with kids and dog and stuff but uh yeah i you know commercial internationally i would actually prefer to be on an emirates jet to dubai than paying 200 grand to be in a small tube right like flying in the nice even to europe you can fly air france first class which is my favorite they pick you up in the airport you don't even see another passenger.

43:57They pick you up at the plane. Like, so flying commercial and then paying for those VIPs. Some countries it's like 200 bucks and you'll, someone will meet you at the plane and take you through immigration. So, you know, it's much easier to like splurge, take a helicopter to JFK, get a sprinter with your friends to, you know, those things can make the friction of like commercial travel, take it way down and it's still safe. Wayne. So you're still like trying to gather your own points and use your own points or no. Funny enough, when I sold the points guy, I put into my contract that I could put a lot of company expense on my credit card so that I would get points.

44:32And all these years later, we're spending a lot of money. All the entrepreneurs out there, anyone out there who does internet advertising, listen to this. The Chase Sapphire Reserve business is now triple points on Google, Microsoft, all internet advertising, unlimited. So we spend a fortune on Facebook and meta ads, and that reserve card is triple points, unlimited. and those chase points are super valuable. So I've, yes, I'm still very actively in the points game and my points, you know, points are like tax-free income when you think about it. Yeah, I love it. I love it. It's your roots. He's never going to leave you regardless how much money you have.

45:09He's never going to leave me. So Brian Kelly is the name of a famous football coach who got fired this year. Has that been an issue for you? It's so funny. The day he got fired, I got so many messages like hate DMs. It's really funny. I was actually sharing them. Well, hopefully now, yeah, he would mess up my Google alert. So, you know, if he's out of the business now, it'll, you know, clear the way for me to be the preeminent Brian Kelly. There's also Brian Kelly of Florida Georgia Line. And I love getting DMs from him of fans like, I'll do anything for tickets. So, yeah, there's several other Brian Kellys.

45:41It's kind of fun. Well, it's interesting. I feel like you have two names. I feel like you have that and then, you know, the points guy. So it seems like you're two names. One more question before we run, Brian. You're meeting with someone to say a little bit earlier in their career. I mean, you're a class president at Pittsburgh. So you're a high achiever from early on in your life. But let's say a recent college grad that wants to leave a positive dent in the world like you've done and like you are doing, but they're not exactly sure yet what they want to do. What are some general pieces of life slash career advice you'd give to them?

46:09I would say find mentors. For me, finding people, even at a company where you might not see your future, find someone at that company that you connect with. Or if you're looking for a job, you say you need to leave a terrible company. You don't know what business you want to do. Interview until you find that hiring manager that you feel is on an upward rise and that you can learn from. That, I think, we often too much focus on the line of work or the company or what the company's trajectory is. But stop focusing on that and look at that manager or the CMO of that company whose organization you would join.

46:46If they've done amazing things, get in right away and just start networking. Put time on the CMO or CEO's calendar. Be bold. If they don't want to meet with you, they don't. But trust me, every senior executive loves to see people come in with eagerness to learn. So often, the younger generations are pegged as not working hard, wanting everything handed to them. So prove that wrong. And I do believe showing up, doing extracurriculars at work, going to the lunch and learn with the senior executive, and actually getting FaceTime with them and making sure they know your name. Those are the things that matter because when it comes time for compensation and reviews and the senior person, you may not work on a day-to-day basis with them, but they're like, oh yeah, that's the person that I really liked what they did.

47:32They are a future leader, right? So if you're on the verge of getting a promotion, you've got buy-in because you're present in there, that's how you get ahead. And then even if that boss leaves to another company, they might take you. So that's such really, really good advice. It's a little surprising coming from a guy. I know you worked at Morgan Stanley, so you understand that element too. But from a guy who's built his own business, but that is so useful. So really good. Brian, where would you send us? I mean, thepointsguy.com, but where else would you send us to learn more about you online?

48:03Yeah. So the Points Guy, all of our social channels and website, I have a weekly newsletter there that you can sign up for. But also my personal Instagram is at Brian Kelly, B-R-I-A-N-K-E-L-L-Y, not the others. And also I wrote a book, How to Win at Travel, which kind of gives all of my tips, a little bit of my story. So if you want to get into the points game and travel the world for a fraction of the cost, I would highly recommend reading it or on audiobook. Love it. Brian, thanks so much, man, for being here. I'm appreciative you have a great team also that works with you. I really appreciate it.

48:38And I'd love to continue our dialogue as we both progress, man. Absolutely. Yeah. Thanks for having me, Ryan.

48:46It is the end of the podcast club. Thank you for being a member of the end of the podcast club. If you are, send me a note, Ryan at learningleader.com. Let me know what you learned from this great conversation with the points guy, Brian Kelly. A few takeaways from my notes. First, work for the right person. That's probably even more important than the right company. Brian's life slash career advice seems simple, but super useful. Find a hiring manager who's on an upward trajectory, someone that you could learn from. That relationship matters more than any other brand name on your resume. Ask yourself, is this person someone, the one I would report to, is it someone I can actually learn from?

49:28Are they going somewhere? That's a useful filter. Chase down that curiosity. Strive to learn and grow with a great mentor or mentors. And then celebrate wins. Brian admitted he did not do this enough the first time around as CEO. High standards are really important, but so does acknowledging progress. Leaders who recognize victories, even the small ones, those are the ones who create momentum and trust and love. That's what we need as leaders. Celebrate those wins. And then think bigger than what feels comfortable. Brian's entire career has been driven by a bold vision. As a kid, he pictured a life of abundance.

50:11And that mindset expanded what he believed was possible. I personally love people who are these big, crazy thinkers. Sometimes it makes me a little nervous that I like that. I want to be more like that. I'm striving for that, being a huge, bold, visionary. That type of thinking shapes the decisions you're willing to make. It can drive action. Once again, I want to say thank you so much for continuing to spread the message and telling a friend or two, hey, you should listen to this episode of The Learning Leader Show with Brian Kelly. I think it will help you become a more effective leader because you continue to do that.

50:46And you also go to Apple Podcasts and Spotify, subscribe to the show, rate it, hopefully five stars and write a thoughtful review by doing all that you are giving me the opportunity to do what I love on a daily basis. And for that, I will forever be grateful. Thank you so, so much. Talk to you soon. Can't wait.

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