Transcript of 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

Welcome to the Learning Leader Show. I am your host, Brian Hawk. Thank you so much for being here. Go to learningleader. Com for show notes of this and all podcast episodes. Go to learningleader. Com. Now on to tonight's featured leader, Brian Kelly, also known as the Points guy. Brian started hacking computers in the '90s, grew up relentlessly resourceful in even as a kid, had Mercedes cutouts on his wall because he envisioned building a wealthy and abundant life. And then he went out and actually did it. After a stint at Morgan Stanley, he built the Points guy into a business generating over a million dollars a month and eventually sold it to bank rate for $28 million. Today, he still leads the Point sky, travels the world, and invest in and advises fast-growing startups. During our conversation, Brian shares the mindset that fueled his rise. We talk about the lessons he learned from scaling a media empire, mistakes he's made as a CEO of a fast-growing company, and the must-have attributes he looks for when hiring a leader. He also opens up about wealth, imposter syndrome, the joy of family, and at the end, he shares some very useful life/ career advice.

Ladies and gentlemen, please enjoy my conversation with Brian Kelly. This episode is brought to you by Insight Global. Insight Global is a staffing and professional services company that builds world-class technical teams for clients around the globe. If you need help with your applications, infrastructure, or data layer, Insight Global's team of technical experts can build custom or manage services to deliver the outcomes you desire. Getting the most out of your technology can be tough, but growing your business with the right technical solutions can be magic. Visit insightglobal. Com/learningleader. That's insightglobal. Com/learningleader. Today to learn more. I read that you were a computer nerd growing up, and you got one of your first jobs. You were hired by your dad to be his travel agent. What What happened here? Can you take me back to that time when you're around 12 years old and got hired by your dad?

Well, I was just a hacker in the '90s. I'm 42 years old today, born in 1983. So if you imagine, 1991, got my first computer, taught myself MS DOS, and And I think in '92 or '93, we got Prodigy Internet. And at age eight or nine, I was the computer system administrator for my family, which is crazy to think about. And yes, so I was always on AOL, Prodigy. Some of my first jobs were in the classified ads on AOL. When eBay first launched in the '90s, you couldn't actually upload any items. So there were thrift shop owners posting for people like me. I was a kid at the time on summer break. I would post their items on eBay in the middle of the night when the server capacity was down. So I had all these very internet-first experiences. Just taught myself how to do everything, including booking travel. And my dad had gotten a job for a startup, 1995. I'm 12 years old, and I start booking all of his travel for him because he had a secretary, and then all of a sudden, he's working from home from a startup based in California.

We lived outside of Philly. So I became his travel agent. He was paying me $10 a booking, and it took me 60 seconds to do. He thought it was much more convoluted. And that was really, yeah, one of my first side hustles was just booking travel for my dad. And then that became points when he said, I have all these American miles, US airways. They're spread out all over there. If you can figure out how to use them, we we can go on a family trip. The rest is history. I booked the six of us in my family, my dad and three siblings, nonstop Philly to Grand Cayman. My mom and I flew on his American miles with a stop in Miami. It was cheaper than going to the Jersey shore, and we went to the Caribbean, all six of us. So that was my first real, oh, wait, this points thing is amazing, but never in a million years did I think it would, that little hobby would take me to where we are today.

As I was preparing for our time, one of the phrases that I originally heard coined by Paul Graham, the famed essay writer and Y Combinator co founder, is relentlessly resourceful. I feel like that is apropos for you. When you hear me say that, what do you think of being relentlessly resourceful?

Absolutely. So I grew up in a middle class family. I actually thought we were poorer than we actually were. I grew up in Bucks County, Pennsylvania, leafy suburbs of Philadelphia. My parents were very humble and did not spend money lavishly, and I grew up around a lot of that. And for me, I always wanted to live a fabulous life. I wanted to travel. I always wanted to go to London. I don't know if it's genetic, but when I was a kid and I would spin the globe and be like, This is where I'm going, I would actually research Oman, and I've been obsessed with this notion of exploring the world, much more so than my three siblings or my parents, really. My parents have now become jet-setters because I get to take them around the world. They just came to with me. But we didn't grow up that way. My mom was one of 10 kids, very middle class upbringing. Somehow, genetically, I got this gene of I need to be rich and travel the world. It didn't just dream of that. I visioned it. I used to call Mercedes, get all of their glossy pamphlets for all their new cars, and I would cut them out.

I had Mercedes all over my bedroom wall growing up. I think on your relentlessly resourceful, points were a way for us to live a fabulous lifestyle, going to the Caribbean in January. But meanwhile, it was almost free. But I've always wanted to live this larger life, and points have been a way to do that through travel.

How much do you think we'll get to you actually being a rich dude now, but how much do you think visioning it and cutting out the pictures of the Mercedes or whatever, how much do you think that played a role in you actually making it happen?

So manifesting alone is not going to make you wealthy, but I do believe being able to vision what it looks like and taste it and get close to it helps you take the smaller steps to actually achieve it. And I do that today. I think of myself and where I want my investments to go. And I actually envision a lot of these companies I'm investing in, what they're going to be. When I envision that and believe that they are multibillion dollar companies and what the potential is, I believe it unlocks a level of just pushing you to reach these many steps that you can't see throughout the process. Hindsight is 2020. And as I look back on my career, I never really felt successful at all these minor moments that actually were pretty incredible. But yeah, I do believe that just believing and seeing and that you can achieve that is an important thing for your psyche to just know and feel?

I'm attracted to people who think way too big. In their mind, it's not way too big. And in my mind, it's not either, even though sometimes I have those doubts. But when I'm around those types of people, which is a big reason why I love this podcast, because most of the people who've sustained excellence over time, they have these wild thoughts. When you start the points guy, could you ever have envisioned it or even dreaming it could get as big as it's gotten?

No, because when I left corporate America, so I was working at Morgan Stanley in a desk job that I frankly hated, and I never wanted to make the Points guy big. And for the first five years of the Points guy, I left Morgan Stanley. I'm making 3 million bucks a year. I've got very few employees, no investors. Life's good. And I was like, this is another theme. Everything I told myself I wouldn't do, I end up doing. So I said, I love corporate America. I don't want to be managing 100 people. I want to just have a small lean team and do this thing that I love and have the money to live flexibly. And I don't want to be reporting into a man. I like my independence. And less than two years from starting the blog, I sold it to a publicly traded company, which then set me off on a trajectory to build this into something. I did know that the other bloggers out there when I started, people think the Points guy was the first blog. There were plenty of other niche points, loyalty blogs, really from the late '90s, early 2000s.

I started the Points guy in 2010, and there were some titan bloggers who are still blogging today. I for sure felt imposter syndrome, but I saw that what they lacked was creativity. Points and miles are very clinical, and that's how the sub-industry approached it. It was these closed off forums like Reddit today. It's called Flyer Talk. And sub-forums diving deep and granular into how to maximize these programs. Very few people were translating that for an audience. And I knew that I had an opportunity to be my 20s living in New York City. I'm not going to tell the masses how to do these really niche things. I'm going to explain what you really need to know, what everyday people. So I knew that there was an opportunity. And then I knew less than six months after blogging, affiliate marketing, when I saw that opportunity, I was like, wait a minute. That started to become lucrative. And then I saw media. No one else in the points world was doing media. They were all doing media is frightening. Luckily for me, I had been student body president, and I know how to speak in public. And while it was scary going on TV the first couple of times, and I almost fainted, I knew that each time I did it, I got better.

And that was the moat I would build. I would build the points guy into a brand more so than any of the others who had come before me had done. And that's really what I saw from the beginning and just continue to double and triple down on that strategy of building something that's more than just a blog, but a lifestyle that people want to achieve.

That's one of the biggest differences. There are lots and lots and lots of blogs. And there were when you came out with yours. And the Points guy, though, becomes... I told you before Before we started recording, I felt like I was a fan of the band before anyone else knew about it. And there was this pivotal day. I don't remember when it was when I'm getting ready to board a Delta flight, and I see the Points guy on the airplane. Delta had won some awards, and maybe you gave them an award or whatever. Regardless, it's next to these other giant brand names of awards that Delta had won. I go, Oh, my God, the band that was unknown, that I knew that nobody else did, is now known. It's on a Delta airplane. So you go from a blog to an empire, and then you sell. I'm just thinking, was that an actual conscious choice to say, I don't want to just be a blog. I want to build an empire. Was that with the infusion of the money in selling and them asking you to stay on board, or what was going through your mind at that?

Yeah, and I sold well before it was an empire. So I think this is the timeline. I start blogging June of 2010. It's just a side hobby making a couple of hundred bucks a month in Google AdSense or whatever. And then it was spring of 2011, I got affiliate marketing. So in 2011, within six months of learning about affiliate, that I could use a credit card link. I made a million bucks in my first six months of just blogging how I was, but using links. No one else really in the industry knew.

Were you still working a full-time job? Yes. You made a million bucks on the side?

Yeah. I had quit. Once I realized that my mom was like, This sounds too good to be true. You can't leave Morgan Stanley. You're about to get vice president. I was 28 8 years old. I was like, no, I knew that it was legit. I believed in it. It did take a leap of faith. So I stayed on to Morgan Stanley. I was making like 300 grand a month. Meanwhile, at Morgan Stanley, my salary is 70,000 a year. So all of a sudden, I started making like 300,000 a month in affiliate, but it didn't pay right away. I think it was like a net 90. So there was this really interesting period where I had my New York Times article come out, TPG is growing and growing, and I'm making all this money, but it's on paper. I had no real money. I was Living in your 20s at 70,000 a year in New York City, you're paycheck to paycheck. So it was this really interesting time where I was working from my cubicle, really paying attention to the points guy, writing blog posts. I realized the more I wrote, the more money I would make, but I hadn't seen a cent of it yet.

So I quit. My parents actually lent me $10,000 just to pay my rent. And luckily, I remember where I was in Madrid when that first Chase deposit of, I don't know, it was 490,000 or something, when the first affiliate check hit from months of backpay. And that was an incredible feeling. And that was when I'm like, I'm just going to do this. But what ended up happening is people did find out, and there was a gold rush. So there were probably about 100 blogs that started over a couple of months about points when people knew that they could make money affiliate. And this is where it became dicey because I had worked at Morgan Stanley, so I understood how banks worked. So as bloggers, but bloggers, most bloggers have zero business sense whatsoever. So they were writing stuff like, Hey, cancel your Amex, cancel your Chase, cancel, cancel, cancel, and then get Get new cards, get new cards, because as bloggers, we would get paid on new signups. But what I saw was this really bad business sense, very short-sighted greediness of other bloggers to screw the credit card companies. And I'm like, just watching this all happen, I'm like, They're going to pull the rug.

So that's why when I was approached in May of 2012 by Bankrate, the CEO, I didn't even have my company up for sale. When they offered me $28 million to buy this blog, I had this negative mindset over where the industry was going. I thought the credit cards would surely close up this affiliate business because so many others were doing it really poorly. So when people ask me, Do you regret selling? Like, yes, the company is way more than what I sold it for. But at the time, you always have to remember what the landscape was. We're coming out of the recession. There were so a lot of weak indicators. It wasn't such a slam dunk that the economy was going to shoot up. So I decided to sell. I had a three and a half year earnout. Over that three and a half years, though, the business really starts to grow. But then I realized, well, I am also the business. So the more press I did when I negotiated with that parent company to stay on, they paid me a lot of money and still a cut of the business to grow it as CEO.

So it's crazy to think 13 years after selling, 14 almost, that I'm still here. But because I built myself as a core center part of the business as the points guy, I've been able to stay on with less of the risk of the business going up and down, getting paid well to do what I love.

So do you own any of it?

I do not own any of it. Actually, in 2017, Bankrate was purchased by a company called Red Ventures, and we were taken private. So Red Ventures, I'm a Red Ventures employee. My compensation is pegged to the performance of the business in certain aspects. In certain aspects, it's like a licensing deal where I am the brand, and I don't manage a person, not even my executive assistant, which is the dream scenario for me. Kudos to all the people managers out there. That is just something I realized. I love teamwork, but real people management, mentorship takes so much time and effort, and I'm more of the brand visionary, the consumer person.

How much are you working with other people? How often do you have meetings with other people? And how much are you working by yourself?

The press team, the head of PR for the Points guy, Bekka Mannheimer, she's been there for nine years. I joke, she's my boss. It's really important to be, we are the trusted source of real pro-consumer travel in America. There's plenty of other websites out there that do travel aspiration and destinations. But at the Point sky, so during the government shutdown, I was booked and busy on every major TV network for two weeks straight, educating people, reminding people of their rights. So I will sit in our strategy meetings more of our, where do we take this brand? What are the products consumers want? Because I'm still very plugged into where the consumer is today. My weekly meetings are very flexible because I want my schedule open so that when I need to be on TV or when we need to be pitching new business, I'm very much the ideas person. So when we're speaking with our long-time clients or pitching When I'm buying new ones, that's really where my special sauce is used and not in the day-to-day.

Do you still travel a lot?

I do. I travel a lot, mostly for leisure now. I have two young kids. So in 2020, I had a breaking moment. Company was over 100 employees. We've got this parent company in Charlotte. So I've got my New York City media cool company, but we launched in the UK. We had a tech team in Austin, Charlotte. So I'm just... Any CEO will know in that growth mode of your business. It's just nonstop. So I basically burn out because I'm also in front of the camera. So I'm not just sitting there in strategy meetings with an exec team and partners and dealing with all of the fires that go along with being CEO, but I'm also in front of the TV the public spokesperson. And that just... It was too much to grow this business and be hiring nonstop. So I had this breakdown where I thought I would actually leave. It was the pandemic. I'm like, travels down, who knows when it'll come back? Is this my sign? It's been 10 years. It's been a great run. But I went to the owners of the Point sky parent company, and I was like, I just can't do it anymore.

And they were like, Brian, we've been waiting for you to say that. You don't need to be CEO. We have plenty of smart people managers at our company. They have a bench of talent. So it was this aha moment of, wait a minute. And I think in life, we often think so it's either black or white. And I remember leaving Morgan Stanley in 2011. It's like, I can leave or never come back, or it's this or that. When I quit my job at Morgan Stanley, she was like, Come back anytime you want. If this blog thing doesn't work out, you're awesome. Appreciate you giving us a heads up. I had given them several months. So that's a piece of advice I give to people, whether it's your parent company, your boss, your mentor. People are not mind readers. And While there is risk to leveling with someone and saying, Hey, this role is just killing me, more often than not in my career, the more vulnerable I was saying, Hey, look, how can we work together to make this work for both of us? It has turned out to be such a blessing.

That's great advice because when I was working in corporate America, and I got offered a separate job, and I love my boss so much. Her name's Dustin Kim. I actually had her on this podcast. I love her so much. She's a CEO now of a company in New York actually called ArtC And I left her because it was this giant promotion to be a VP at a sister company. It doesn't matter. But she goes, why didn't you tell me you wanted to do something like that? I would have made that happen in my organization for me. And I just thought, well, I don't know. I felt weird being super ambitious or telling you that I just thought I should just do my job as hard as I can and not. And she goes, no, tell me. I can't read your mind. I didn't know that that's what you want to do. I could have made it happen. I had already given my word and accepted that offer. And I was I'm just like, Oh, it sounds so basic, right? Well, just tell them what you want. But it seems like in your case, just being honest.

And also, I'm sure it helps that whether it's the people at Morgan Stanley or the points guy of doing excellent work every single day, urns you those conversations to just be as real as humanly possible and let them know what you're thinking and how you feel.

Totally. I cannot stress that enough to people. And also what I'll remind people is I had some employees, and whenever employees come up to me now leaving the points sky, some have started amazing things in businesses, always leave on good terms. I cannot stress this enough. I mean, the whole going out guns blazing on X, roasting your company is the dumbest thing you could do. I have so many former employees at the Point sky that now I've hired at some of my portfolio companies that I invest in, and they now stay on good terms because the network is smaller than you think and just Keeping good relationships with former companies, even if you hate that company, is the only way to do it because burning bridges on your way out may feel good for a day, but it will come back to haunt you.

I 100 % agree. I do want to focus on inflection points and moments. I love specific moments in people's careers, and you, it seems like you have a very good memory of these moments as everything I read online and now talking to you about it. But was it the New York Times when they reached out? What was it that took you from this blogger who was doing a really good job and had a solid audience to then this rocket ship, upward arrow growth that started happening for you?

The New York Times was a really pivotal piece. And a little tip I like to give people, check your spam email, especially as a very entrepreneur. So at the New York Times, Seth Kugel had written to me, and it went to my spam. And I was just going through my spam inbox one day, and it was like, New York Times interview request. And that email changed the trajectory of the points guy for so many different reasons. Number one, SEO-wise in 2011, a New York Times digital article to your little blog. I mean, from that point on, traffic, credibility, I didn't even understand it at the time, as featured in the New York Times. All of a sudden, I went from this blogger to New York Times recommended travel expert, and everything is branding. Those were definitely inflection points, because I was frustrated in the media in 2011. It's funny because people today will say, Well, the points game is over. It's changing. Well, no shit. It's been changing forever. In 2011, people called points dead. I was the only one in media really having a pro-point spin. Every other journalist had this trope of like, Oh, blackout day, it's freaking the flyer miles are over.

So that was the narrative in 2011. And in hindsight, there were so many insane deals back then compared to today. But I'd also argue today that there's way more credit cards than ever before. So the world is shifting, but just move along with it is the message. So So when I realized that media, I could be the voice of this community and do it in a informative, fun way. And then also in social media, Instagram hadn't even started when I started the Point sky. But showing myself along with these travels. Most other bloggers, they would review an airline and it would just be a picture of the seat with a picture of a meal and a very clinical... I'm like, Let me put my spin. I'm 6'7. So I knew if I can fit in this business class seat, I know anyone reading, whether you're tall or short, everyone's going to be like, Oh, no, this is good. So I always just try to put my personal angle. In my hotel reviews, I'll stand underneath the shower and do my TPG shower test, just to see if the shower head actually cleared. So all these funny, cheeky little things But I also saw this is the Kardashian's America.

Reality TV is what we watch, and people want to know who they're supporting. So I viewed all of that in real-time like, Oh, this is my opportunity to be the face of this industry.

I think people want to follow people.

A hundred %.

I mean, we like brands. I like Nike and Just Do It or whatever. We like those things. But I also liked Michael Jordan as part of that brand. And I think that's one of the key insights, because somebody would say, well, if you want to build an empire, you can't make it about you. You need to think about a bigger scaling type thing. I'm in the middle of this right now, too, because I feel like the connection that I make with people through this parasocial relationship of them listening to a podcast for 11 in years, and then I meet them in person, and they feel like they know me. I go, it's because you do. You do. We've been in conversation now. I haven't been talking to you directly, and I haven't heard from you. And I feel like that's something you've gotten good at, where you can build the empire But also make it personal and not maybe listen to the advice and say, Hey, Brian, it can't be about you or the points guy. It's got to be about the bigger scaling things that you have to do. And I don't know, I just love to hear you rift on that because this is something I think about and working through as we speak of personal branding, bigger branding, building something bigger than yourself, even though you still want to show yourself because that makes it more human and real and connection-based with the people who are following.

Yeah. I think the points, guys, will be an interesting case study because I don't write any of the content today. I have a weekly newsletter, but for years, I have not been a key writer. I knew hiring the smartest people and having them We bought a blog, Mommy Points in 2018, just about family travel, and we've had all sorts of travel. I knew very early on, yes, I'm the draw often to the site. I might be the person someone sees on Good Morning America who's like, Oh, that guy has really good tips. Let me go to the site. But then they come in into our ecosystem, and there are so many other ways that we can pull you in. We'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. 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 a 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 appear in videos and tent poles, but 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 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.

For sure. In the very beginning, when I was just over-analyzing every decision, and when I was CEO up until 2010, 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, in a very viral post at the time, we had the wrong capital 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 on my time as CEO, I was a tough boss because as a founder, I still- It's so personal, right?

It is so personal, yeah. 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. And 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 a simple... They didn't mean to, just made 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 human, we like to get... It's much more positive reinforcement over negative. And so to founders out there who are scaling, you need to check yourself and have someone around you, a leadership team, someone that can check you. I 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... The business, by all external metrics, was booming for so many years. I think 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 inviting that feedback and not freaking out when they give it to you is important. And that's something I definitely would think about if I did it again. I know I would be a much different CEO today, but-We need truth tellers, man.

We all do. A hundred %. 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. We have a new CEO at the Point sky. I work with her, Liza Lansman. She's amazing. We just hired a bunch of senior executives. We're 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, 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. But I think far too many senior executives walk into positions and they're Oh, wait a minute. 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 truth-telling in the interview process is the beginning of 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. You just lost a year. And for me in the interview process, it's, Stop telling me wins because look, anyone can make their job look successful. Oh, 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. I want people to be real and allow me to understand 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. You can feel that they're telling the truth about wins, losses, everything in between. What Are there some other things? Do you use your gut intuition? Like, I really like her. I like him.

Yeah, that's gotten me in trouble in the past. Really? Yeah. Just obviously, because the problem is, very charismatic people can trick you easily, right? Especially when you're exhausted as a CEO, and then you go into an interview and you're like, oh. And then someone's 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. And when you dive deep, I don't want personality hires. I'm the personality, or at least in certain roles. In a sales role, a personality role might be higher, but my engineering team, 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 you really can't verify a lot. Even with checking references nowadays, you have to... At the end of the day, you do have to go with the gut feeling.

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? Because 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 Point sky, but I have 10 employees that work for me personally as I'm building. 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. 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. I think for a long time, I was traveling a lot. I 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 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, but- Where is 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. So having that, I think, that is what I highly recommend, and get a designer to do things correctly. I'm still cheap in a lot of ways, so I would buy my own furniture and I'm shopping online. At the end of the day, hire professionals to do and make your home really comfortable, your office. And 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? Why do all that?

Well, that's an interesting... 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-fiance 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 had that conversation. And at the same time, I had always been approached by other founders to help advise. And there was one company, the Morning Brew. They were readers of the Point sky, and they kept bothering me to be an investor and adviser. In this little newsletter. I did, and it was a 10X investment over two years. I helped them because what they were building was very similar to what I built at the Point sky. 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 chaotic travel schedule. 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, Encore 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 put it off, and it was April of 2020. He told me the thought process of what is now built. I 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 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 has also shown me that 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 I love it because I can help advise founders on everything I've done, help open doors, give my comms. I know every influencer. Using that to build wealth is really angel investing has 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 not all of them. I've definitely had flops. Sure. I always will. But I feel really good that there's... I mean, once you have one mega one built...

Yeah, it can make up for 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?

I mean, relentless is the first thing that comes to mind. So Encore, I am amazed at his ability to just... If he's got 10 major things impacting his business, most CEOs will start with one or two I'll 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. 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 I could retire, but I love it. I'm a racehorse, right? 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 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 Spellefogel, intern for me at the Point of Sky 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 a Coinbase credit card, Qatar Airways. And now in 2026, they got the built business. So the huge build is going from Wells Fargo to Cardless. So that's a really cool moment for me as an investor advisor in two businesses that are now coming together to do amazing things that is very exciting to me. And now I feel like I'm a part of history in 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 are around, they're 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. I 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. 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. I just took them to Antarctica with my family.

Is that in a Guinness Book of World Records? Is that a real thing?

It'll be in Guinness, yeah. He'll be 12 months and 10 days. For years, the record was three years old. Just recently, an 18-month-old broke the record. I'm like, Sorry, buddy. My son will be a year old, which is just a fun thing we did. I didn't even set up to do it, but I love to challenge myself. But I'm home, especially until my kids turn five 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. So 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 I chose to have kids on my own. And I'm very aware of, I don't want to have kids in this world as a single dad and then not be present for them.

That's pretty wild, man. What made you want to do that?

I've always wanted to be a dad. It's 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 I always knew I wanted kids, but the business, I always put the business first. From 2010 to 2020, when I was CEO of the Point, got a jet sitting 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-fiance 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. I 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 It's a life dream of mine.

Wow. That's wild, man. 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?

I just recently went to Antarctica. I'm a big nature, outdoor I love being in places where you feel completely on a different planet. National Geographic Lindblad now has this ability to fly from Patagonia and Chile. You can fly 2 hours to King George Island and then get on a ship for 6 nights, which to me is perfect. I'm ADD. I don't want to be in a cruisehip for two weeks. I don't want to cross the Drake Passage for four days straight in rough seas. So this, to me, was 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 Malowan is like, I went there this year, unbelievable safari, Cape Town, wine country. It's the ultimate soul refreshing trip for me.

Okay, this is a projection of my situation. You got 3. 3 million Delta miles. Diamond, how are you using them?

Unfortunately, Deltas, of all the airlines, they're a 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. Deltas 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 at landed at Cape Town, and Joburg. So redeemed to go to South Africa or Australia, I think, would be how I use those.

I think you have to get the lay down. That would be a rough one without it.

Oh, yeah.

Do you still fly commercial?

I do, actually. And I'll charter here and there, but I'm still a deal seeker, so it really rarely makes sense unless I'm flying short distances around with kids and dog and stuff. But commercial internationally, I would actually prefer to be on an Emirates jet to Dubai than paying 200 grand to be in a small tube. 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. They pick you up at the plane. So flying commercial and then paying for those VIPs. Some countries, it's like 200 bucks, and someone will meet you at the plane and take you through immigration. So it's much easier to splurge, take a helicopter to JFK, get a sprinter with your friends. Those things can make the friction of commercial travel take it way down and still save way more money.

So you're still 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 my company expense on my credit card so that I would get points. And 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 have... Yes, I'm still very actively in the points game, and my points game. And my points are like tax-free income when you think about it.

Yeah, I love it. I love it. It's your roots. It's never going to leave you regardless of how much money you have. It'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 if he's out of the business now, it'll clear the way for me to to be the predominant 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. It's fun.

What's interesting, I feel like you have two names. I feel like You have that and then the points guy. So it seems like you're two names. One more question before we run, Brian. You're meeting with someone, let's say, a little bit earlier in their career. I mean, you're a class president at Pittsburgh, so you're 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/ career advice you'd give to them?

I 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. If they've done amazing things, and 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 like what they did. They are a future leader, right? So if you're on the verge of getting a promotion, you 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.

That's such really, really good advice. 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, thepointsky. Com, but where else would you send us to learn more about you online?

Yeah. So the Pointsky, 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 Kelley, B-R-I-A-N-K-E-L-L-Y, not the others. Also, I wrote a book, How to Win at Travel, which gives all of my tips, a little bit of my story. 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 an 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, and I'd love to continue our dialog as we both progress, man.

Absolutely. Yeah, thanks for having me, Ryan.

It 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, rian@learningleader. Com. Let me know what you learned from this great conversation with the points guy, Brian Kelly. A few takeaways for my notes. First, work for the right person. That's probably even more important than the right company. Brian's life/ 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, the one I would report to, is it someone I can actually learn from? Are they going somewhere? That's a useful filter. Chase down that curiosity. Strive to learn and grow with a great mentor or mentors. 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, and 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, but 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, and 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. For that, I will forever be grateful. Thank you so much. Talk to you soon. Can't wait.