← The Messy Parts
The Messy Parts
The Points Guy Couldn't Get His Own Credit Card: Then He Made $28 Million (at 28 Years Old)
00:39:37
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- [00:00]
A
I had to negotiate head to head as a 28 year old to this publicly traded company CEO who loved me. But it was also this. Negotiations get crazy. It is the biggest mind fuck where one day you're like, I'm selling my company, and the next day you're like, oh, no, they're not responding because they're playing mind games. But at the end of the day, he offered me $28 million.
- [00:19]
B
Well, I just want you to say that again. $28 million.
- [00:22]
A
I'm 28 years old and they offer me $28 million for a blog that I paid, you know, $10 for every single person I knew. All my entrepreneur friends take the money. It was life changing. It was like winning the lottery. I mean, I went through a lot of ups and downs with that. People come out of the woodwork. There's different dynamics.
- [00:40]
B
All right, so let's talk about the messy. What was messy? Because it's all sounding really good right about now. This week on the Messy Parts, we're hearing from Brian Kelly, the points guy, a travel influencer, author, and entrepreneur. You can learn about how to maximize your points on his website, the Points Guy. But here we're talking about the mess behind his success. How he figured out what his superpower was, leaned into it, which was all about relationships, and how at 28, he sold his business for $28 million. Brian, thank you so much for coming onto the blue couch. You know, you've had this really interesting journey, and as I was thinking about who to have on, you seem like you'd be a really good person to.
- [01:29]
A
Have a really messy guest.
- [01:30]
B
Well, a messy guest, yes. I like the messiness. So what I love about doing these podcasts is I get to research people who I know and then discover so many things.
- [01:40]
A
Is the temperature going up in here?
- [01:42]
B
So I kind of now think of you as like Superman. You were a person and then you became the points guy. You had a transformation into a superhero. But I wanna talk about your origin story, sort of like where you grew up. I read the story about how your dad said to you, you can use the points and book a trip. I wanna, like, come into the home of young Brian. Like, what was your home like? I don't know that a lot of people's dads would say, take the points and book a trip at 12 to.
- [02:12]
A
Understand the points guy. We have to take a look at the points, kid.
- [02:16]
B
Yes.
- [02:16]
A
Cause that's really where it all began. So my background, I was born in Long island, big Irish Catholic family. So I Have two older brothers and a young. And when I was seven, we moved from Long island to Bucks County, Philadelphia. It was a huge kind of moment for our family. We had to start from scratch. But I mean, growing up In Bucks County, Pennsylvania, Doylestown, about 45 minutes north of Philly, was this kind of really nice lifestyle.
- [02:40]
B
But why did you have to move?
- [02:41]
A
So my dad got a job. He worked in health care, consulting, hospital group purchasing. And then about four years after we moved, he got a job for a startup based in Chatsworth, California. So this is where the points start coming in because he started commuting every other week from Philly to la. So he at the time was flying US Airways and American Airlines and was accruing a bunch of frequent flyer miles. I remember he had a big computer and a Velcro bag and he had to book his own travel. I was always the tech whiz in the house. I've always been obsessed with technology, I think. Cause I idolized my dad. We're both the third son, we're both Brian Kelly. So my whole life I idolized my dad, the businessman. Like my two older brothers, when we would get toys, they would get remote controlled cars. And I remember, remember going into James Way and going to the business section. I got a stamp pad, I got a ledger. And for Christmas one year, all I wanted was a cash register.
- [03:36]
B
I was gonna say, I'm seeing the Cha Ching cash register.
- [03:39]
A
I just. In my head, you know, So I kind of had this obsession. I wanted to be fabulous. I've always known that I want to live this larger than life, you know, life.
- [03:48]
B
Why did you think of a business person as having a larger than life experience? Because most people think Willy Loman.
- [03:55]
A
Yeah, well, so. And my dad was very modest. My parents are both very conservative with money. I thought we were poor growing up. They were. They're not big spenders.
- [04:05]
B
Were you poor?
- [04:06]
A
We were firmly middle class. And I think as my dad made it up, definitely upper middle class. But my parents never spent. They didn't buy me a brand new BMW like so many of my friends on their 16th birthday. My dad gave me his.
- [04:17]
B
My dad didn't get me a BMW.
- [04:19]
A
I'm so thankful today. I remember being enraged, but my dad was like, work for it. He's like, you have my 1994 Bonneville used, and if you want a nicer car, work for it. And I started hustling. So yes, traveling businessman, fabulous lifestyle. So I think two things were going on. So I love my dad and his lifestyle, but I Also grew up, you know, living in Bucks County. We would go into New York City, so my dad would use his Marriott points and we would stay at the, the Marriott Marquis, Times Square from a very young age. So we would take trips into Manhattan. And I think I caught the pulse of Manhattan. When I look back, I'm fusing together. I want to travel the world, I want to be a businessman, and I want to live this fabulous New York City life.
- [04:58]
B
Did you know at that point that you were gay?
- [05:00]
A
I did. I definitely knew I was gay from, I think actually even when I was seven years old, I remember I got New Kids on the Block trading cards and I remember like kissing Joey McIntyre's card and I'm being like, he's going to be my husband one day. Not understanding. What gay? No. And not to anyone else. You know, I think it was 1989. So I grew up, you know, the tail end of the AIDS epidemic. All the images of gay people were negative. So I didn't come out until after college. But I always knew I was unequivocally.
- [05:32]
B
That's why you knew you were coming to New York.
- [05:34]
A
Exactly. I think that's another piece of my homosexuality. And I think deep down I was like, I need to get to New York City to live the life that I was destined to live.
- [05:43]
B
You clearly were good with technology. Your dad was traveling and he used points, which already, that gave you a window into points could be something that you could trade in to come to Times Square. And so he challenges you to use points to book a family vacation.
- [06:00]
A
And when he first got the job for the startup, he said, I need to book my own travel. I was like the AOL prodigy Internet whiz in my family. So at age I think nine, I was the computer administrator for our Acer computer. One of my first side hustles was selling thrift shop products for thrift shop owners. I was making hundreds of dollars as a 12 year old running this side, but. And I would post ads on AOL Classifieds. Hey, thrift shop owners, do you need to get your items?
- [06:25]
B
How did you even know to do that?
- [06:26]
A
I was just super into the Internet. I mean, in 1991 I, I was eight and I installed the modem. I was just always ahead of the curve. So when my dad got the job at the startup, I charged him $10 a booking. And that's the year Travelocity started. So booking his travel was super easy. It took me one minute and I was getting paid $10 per booking. And then that's when he said, we'll go on a family trip if you can figure out how to use these miles. And I remember I got on the phone, called US Airways, American Airlines, and I got all six of us to go to the Cayman Islands for free.
- [06:59]
B
Is everyone in your family like you?
- [07:01]
A
No. My parents always ask, where did you come from?
- [07:03]
B
So you then decide to go to college. You go to Pitt. I read that you said you weren't a particularly great student, that you had add. Maybe before we all knew we all had add, but that really being in student government was a thing that was a game changer.
- [07:17]
A
I had good grades in high school, sats, but when I got to college, it was overwhelming. The lecture format was. I couldn't pay attention for one second. Then I also. I got involved in my. I became the president of my dorm. And then that led me into student government and all these different activities which I thrived in. And to me looking back, thank God I did them. Because what I learned, becoming student body president, managing a team, I had interns. I was meeting with the chancellor of the university, learning how to speak to influential people, speaking in public, all of that, to me, is much more important than acing my astronomy lecture. Of course, I'm not putting down academics, but my grades were terrible. But I at least channeled all my energy into student activities.
- [08:01]
B
I read that you, like, traveled for a student body president, so we were.
- [08:05]
A
Going to every student government conference possible.
- [08:07]
B
I just want you to know I was my freshman class president. I never traveled for that role.
- [08:12]
A
Yeah, there was a big conference of student government associations that was in Texas. We would go there. We would go to other ones across the country. And then I studied abroad. Then I got a cheap flight. So all of a sudden, in my junior year of college, I had US Airways gold status. That's when I really got it. I found flyer talk in 2003 or 4. Flyer talk is like Reddit for, you know, nerds in the loyalty space. My dad and I were doing this as, like, a bonding thing all throughout the 90s.
- [08:38]
B
Some people do fantasy football. You guys were playing loyalty points.
- [08:42]
A
Totally. And it was great. It was like, we get these free trips every year. We would take this epic family trip in January or February when living outside of Philadelphia is horrible, and we would come back obnoxiously sunburnt from our vacation. And all my friends, I. I think a part of it, too, is that my friends thought we were rich because we're going to the Caribbean. Yeah. And that, to me was like, oh, this Is so cool. These points can help you live a lifestyle that's frankly unbelievable. I never thought, years later, I would sell that dream to millions of people.
- [09:18]
B
How did you land your first job?
- [09:19]
A
So I interned for Philip Morris, going around to gas stations and Walmarts and learning the business of cigarettes. I interned at State Farm at Northwestern Mutual. I just wanted to get experience to everything. So when I graduated, I was gay, and I was, you know, 22. And I'm like, okay, this is gonna burst. Like, I can't. I knew I was.
- [09:38]
B
And you still weren't out.
- [09:39]
A
I still was not out, but I knew I. So I was like, I have to take the job that gets me to New York City. And then a friend of mine I interned with at State Farm, he had gone to Bucknell, and he got a job at Lord and Taylor. Funny enough, he said, the buying world is all women, and they need more men. So who would have guessed? You know, I interviewed with all women. They trotted me around. You know, I put on the charisma. I'm like, I don't know anything about fashion. Horrible style, and. But they loved me. And I was like, I put my charisma skill to the test and got the job. It was $45,000 a year in 2006, which I thought was going to be. I was rich and, you know, realized very quickly in New York City, where half my paycheck was going to rent. And they put me in the cosmetics buying office. So I knew nothing about fashion. But that cosmetics business is very client focused. I mean, I would go to the Chanel headquarters, and it was all about me connecting with their assistants so that we could get the sample first to do for our photo shoot over the other bigger brands, because I had better relationships. I was terrible at, like, the number side of the business, but it was really fun to be in a role where I could, you know, put on my people skills to make a difference.
- [10:52]
B
I want to talk about that, because clearly one of your skills early on was being good with people and understanding the power of relationships. But, you know, you're, like, 22. Like, how did you really understand that? Like, what? Now you can look back and say that I was turning on my charisma skills. Did you know that that's what that was like? What was that to you at that age?
- [11:11]
A
I did know, and I loved being around people. And I was nervous going into this assistant buyer role because I did a lot of coordination, which is not my strong suit. They immediately called me the mayor of Laur in My trainee class, I organized the happy hours so I knew in order to compete, it wasn't going to be on analytics. I would fail immediately, but it would be on being liked.
- [11:33]
B
That's such a great lesson if you think about it, right? There's so many people looking for a job or looking to pivot. You have this incredible ability to say, I'm not really going to be able to win at this, but I'm good at this. Oftentimes people think, well, I should just learn that I should force myself to master the numbers. You knew to pivot. Was there a messy moment in that job at Lord and Taylor?
- [11:55]
A
I was messy with my finances. My credit crashed to the point where I was getting emails from creditors saying, we're going to garnish your wages. And I was so embarrassed. I have no money. I actually was doing odd jobs on Craigslist. I took a payday loan one day because I. And I refused to go to my parents for money. I lived in Soho. I would walk to 39th and 5th. I couldn't pay for dry cleaning. So my boss actually pulled me aside one day. I was like, brian, you have to dry clean your suits. So I was kind of in shambles financially. And that was the moment where I'm like, to fix this equation, I need to make more money.
- [12:29]
B
And that's what made you go to Morgan Stanley.
- [12:32]
A
So then I actually went to HR and I said, I need to go to campus recruiting, because that was an immediate bump. I got an extra 10k, but then I'm like, this 10k is really not making much of a difference with my finances. Early 07, the banks were booming, bottle service clubs. All my friends in finance were living this crazy life. And they were all like, well, if you're going to do recruiting, do it at a big investment bank. And so I applied to a million and eventually got the job at Morgan Stanley in their tech division. So I went from selling makeup to selling careers to computer scientists and engineers of which I knew nothing about.
- [13:08]
B
This is the Wall Street Brian face. So it's so interesting because, you know, here you are struggling sort of on a whole bunch of different levels, right? It is expensive when you're young to live in New York City. And a lot of these jobs that sound glamorous don't pay enough. I mean, we've had a lot of people on the couch having this exact same conversation. And yet you sort of persevered. Like, what kept you going?
- [13:30]
A
I knew I wanted to stay in New York. I was still exploring being out but being able to go to gay bars, meet people like this was the life I wanted. As tough as it was, I was just like, I just need to make more money. That is clear to me. I just need to make more money. Every interview that I would go on, I'm like, I have to get this job. And at Morgan Stanley, it took nine rounds of interviews. After each round, though, I would research them, and if they were from Pennsylvania, I would figure out every way to connect with them. But I would listen to Mariah Carey, make it happen. I'm like, just, this just has to happen. It's kind of manifesting. I do believe in manifesting. You have to.
- [14:03]
B
Mariah Carey was your mantra.
- [14:05]
A
Make it happen. Everyone listening. If you need a little boost, listen to Mariah Carey. Make it happen. There's also a live version, which is excellent as well.
- [14:11]
B
Okay, so now you're at Morgan Stanley. Now we're at Wall street, and we're making our way to Superhero Brian. And you're doing recruiting for them. And wow, now the points are racking up because you're offering to do everybody's expenses.
- [14:23]
A
Well, I don't even know if I wrote it in my book, but because my credit was so ruined, I couldn't get a corporate Amex at first. I had to get my managing director to sign a guarantee form for me, which was.
- [14:34]
B
That must have been really hard to ask.
- [14:35]
A
Mortifying. But I think my corporate. My first corporate Amex because I had terrible credit, was like $3,000 credit limit. I'm like, well, that's not even one recruiting trip, you know? So once I got the big credit line, that's when the point started coming in. You know, career fairs at Cornell, 15 grand. Oh, that'll go on my card. So everyone in hr, I was the campus recruiter. All expenses. Brian is our comrade. He's the expense expert. People say, brian, you know, I've got 20 grand at NYU. Can you do this sponsorship? I'm like, gladly. So cha ching, cha ching. All my points start racking up, and that's when I really get back in. Because I had taken a hiatus from the point game, I was in survival mode. All of a sudden, I'm like, oh, I can start traveling again. And then the economy crashes about three months after I start, which actually presented an amazing opportunity for business travelers. So for the few business travelers that still had budgets, which I did, I wasn't in banking recruiting. I was in the tech. So even though the bank was in crisis, everyone at Morgan Stanley and every bank knew you Gotta keep foot on the gas on tech talent. So I'm traveling a ton. Hyatt had a promotion. It used to be called Faster free nights. So two nights at a cheap Hyatt place on a recruiting trip got me one free night at the Park Height Paris. So I was in this ultimate power spot, still making 70k a year, 80 maybe at my peak there, which is still nothing in New York City. And I had a little bit of credit card debt, but all of a sudden I'm jetting in first class on weekends. And I would leave New York City because all my hotel elite status. So it's cheaper for me to fly and use points every weekend than it would be to stay in New York and, you know, have to split a dinner with friends.
- [16:12]
B
You know, what's interesting to me is that you say you're not good with numbers, but loyalty points, really, it is kind of an analytics game.
- [16:19]
A
I am good with numbers. I'm good with normal numbers. I'm not good with deep analysis. Like I failed calculus, but I'm very good at. I run the numbers all the time in my head. Statistics, odds and, you know, certainly with points, and understanding where the opportunities lie. Like that I'm very good at.
- [16:37]
B
Okay, so now you're Morgan Stanley. You're traveling a ton, racking up points, and a friend, or maybe it was somebody you were dating, somebody somehow mentions to you this idea of doing a blog.
- [16:48]
A
You know, working at Morgan Stanley was stressful, the recession. But I knew my job was good. They loved me. I was doing a really good job. I was a great salesperson for the bank. So my ex at the time was like, you're a genius with points. You should monetize that skill. Everyone comes up to you. You help all of our family and friends. And there were some bloggers in the points world that were doing award booking services. So the points guy, when we first launched was not even a blog. It was just a shell website where you could put in all your points. It would email me and I would say, yeah, I can book these tickets. You know, family of four, you wanted to go to Italy with your American miles. I was making, you know, 500, a thousand bucks a month, cash on the side, which was nice. In June of 2010, a friend was like, you have to blog. This is the moment, trust me. He said it was so much conviction. Just write good content every day at the same time. So I just started blogging in June of 2010 and it started to take off. You know, throughout that year. Wasn't Monetizing. But it wasn't until, like, early in 2011, I noticed another blogger had really weird links when he would link to Amex and Chase. And I pulled him aside at a conference. And once again, I use my personality skills. He's an older guy, the frugal travel guy, Rick Ingersoll. He changed my life. He pulled me into a side room at one of these weird miles and points conferences, and he said, you cannot tell anyone. He was giddy. He was 65 years old and giddy. He's like, I'm rich. I'm rich. He's like, those weird links you see me doing, they're affiliate. The credit card companies are now paying us to promote their product. So I'd been blogging about the best amex card, the Chase card, and just linking directly to Chase or Amex, and he's like, I can get you in. And a friend from college worked at one of the. Which is now Rakuten. He got me into affiliate marketing. Made five grand the first month and then 200 grand the next month.
- [18:30]
B
The thing that strikes me is that you now have a side hustle in an era where side hustles weren't really a thing. I mean, now Everybody who's under 30 seems to have a side hustle. I joke at 56, I have two side hustles. Maybe six.
- [18:43]
A
I'm not sure, but I think you're closer to 10.
- [18:46]
B
Might be 10, but. So side hustles weren't a thing. Did Morgan Stanley know that you were doing this?
- [18:53]
A
So we had what was called outside business interest, which, as I look back, I'm like, outside business interest really was for bankers, right? If they had investments and stuff and then would bring them to the firm. But my little travel blog, the points guy, registered as an outside business interest. My managing director in HR was like, good job, Brian. You and your little travel blog. But they knew I was good at travel. They're like, you should blog. Like. I was like, it's a creative outlet. Thank God I did, because a, I had jealous colleagues try to tear me down.
- [19:24]
B
Let's talk about those messy moments, because we've all had those experiences in the corporate world.
- [19:28]
A
So I also did our LGBTQ recruiting. Morgan Stanley was awesome with that. And through that, I got an amazing senior leadership mentor, Jeffrey Simonoff, who went on to become the head of diversity at Apple. He's iconic. And then so when I had this, you know, incident where this colleague, out of nowhere, she was nice as can be to me. And then I find out she's going to HR trying to get me fired because she was jealous because I had all these roles in hr. She sees me as this golden boy. And, oh, he's working on this at work. And they almost fired me. But because of my amazing mentorship with someone super senior that I could go to and have that outlet. And he saw the big picture. He saved me from getting fired. And if I would have gotten fired at that point, I only left Morgan Stanley put when I the money was rolling in from the points guy. This was early on if I would have gotten fired from the points guy and had to scramble. It may not be what it is today. So my advice to people is, especially in big organizations, you need allies. Especially if your side hustle takes off, you start to get attention. There are negative sides to it that you can't be naive. You have to play a game of chess.
- [20:30]
B
So you're a people person, and you're definitely somebody who's likable. And here you have somebody who you think likes you, who turns on you.
- [20:38]
A
What did that feel like? It was violating. I'm an optimist. I'm very generous, I think. I like to give, you know, people the benefit of the doubt. That has always come to haunt me. I've had best friends, you know, interior designers who have stolen from me, done crazy things. It toughened me up, and it opened my eyes. And I think every moment that you have, you just have to spin it into something better. And through every moment of messiness, like I really have learned, sometimes I do need to change my approach and not be so naive, because especially as your success grows, there's more targets on you for sure.
- [21:12]
B
So you're a Morgan Stanley family. You don't get fired. Your side hustle begins to take off because of a New York Times article, and all of a sudden, the points guy is on fire.
- [21:21]
A
Yep.
- [21:22]
B
When did you know that Wall Street Brian was over and points guy Brian.
- [21:26]
A
Was the exact day. So February of 2011, I get into affiliate marketing. I made five grand just doing nothing. Just my normal post. I'd put a link and then the New York Times, Seth Kugle had emailed me. It sat in my spam inbox. I met with him in March of 2011, and in the end, he ended up. I think it was April 11th of 2011. He wrote the article that was like, this is the site that everyone basically needs to read. He used to be like, oh, loyalty's dumb. I'm budget. You just got to go. The cheapest flight, cheapest hotel. So I changed everything. I helped him book a flight to see his girlfriend. And he was just blown away. He's like, you just turned this currency that was sitting in my Delta account, you turned that into real human connection with my long distance girlfriend and that he was blown away by. So the day his article came out was a big day in the credit card space. This is. It was 2011. Chase British Airways card had a hundred thousand mile bonus, which was one of the first hundred thousand mile bonuses. So this is well before the sapphire. And I knew that offer might come out. So I had stayed home from Morgan Stanley and I was like, I'm going to write content. I got to be ready to go and post this because this is going to be a big offer. So I'm like, I can market this. It's going to go viral. So that offer comes out, my adrenaline's rushing, my website goes down. And the day that offer went live is the day the New York Times went live. All of a sudden, probably 50,000 high intent travelers are landing on the points guy and they're seeing a hundred thousand points. Best ever. Five trips to Hawaii for free. Bam. Everyone starts sending it to their friends. You only get paid if someone signs up for a card. A click to an application is $0, but a click to an approved application might be 300. So on a normal day, I'd have maybe 100 clicks. And then all of a sudden it was 22,000 clicks onto the landing page to apply for this credit card. And I just start thinking, well, the conversion rate, if it's just a tiny piece. And I was in my shower in Williamsburg and I was like, I'm pretty sure I'm rich. I think it was $125,000 I made that day and 58 the next day. And from that point on, it was six months until I made a million dollars. An affiliate.
- [23:36]
B
That's incredible.
- [23:37]
A
So I quit my job the next day at Morgan Stanley, even though that money was far from being paid. My mom was like, what do you know? This sounds too crazy.
- [23:46]
B
She's like, I don't believe it.
- [23:47]
A
I'm like, well, in this affiliate portal of this random affiliate company, it's showing like every day just money would drop. My balance would be like 29,000. Then at 3:30pm the next day, they would batch load all the new conversions. And then I go from 32,000 to 64,000. And I'm sitting at my cubicle in Times Square, like, what is happening? My life was changing before my eyes and I quit My job. And my boss goes, good, you should. I didn't tell her how much money I was making, but she's like, if it doesn't work out, you always have a job here. And that was like, I sat on that. Should I quit? Should I not? It's this yes or no binary. Finding the time to jump is never easy, but often if you do it, that you can always kind of go back is what I tell people. So if you have that moment, you.
- [24:33]
B
Can only go back if you leave.
- [24:35]
A
In the right on good terms. Yeah. So made sure to leave on the right terms.
- [24:39]
B
At one point, did you have sort of like two identities? Brian versus the points guy.
- [24:43]
A
My first experience at a dinner party was probably November of 2010, and someone said, you're the points guy. We were at a dinner party and their eyes lit up and they almost, I think maybe started shaking. They're like, I love your stuff. And that was a moment where I was like, wow, people are connecting with the content because I think I made points. Cool. There were plenty of other points blogs, but they're very clinical. Very like, this is how you maximize the most value from points. I kind of made this a lifestyle. I live and work in New York City. I'm in my 20s. I don't have time to do a lot of nonsense, but here's what you need to do. Most of the other travel bloggers never even had a photo of themselves. I would then start traveling and be like, I'm six, seven. If I can fit in this delta lie flat seat, you can too. And I started doing silly things with it and having fun. And it's still very interesting being the points guy. And even my mom later that year would be like, tpg, when are you coming home? And it's so cool because I can be the points guy when I want to, but most of the time I don't have to be. But it's fun to step into it. Or when I go to an airport and people light up, if I go to a Centurion lounge, it's still cool to me. I still enjoy greatly being this superhero that can help make people's lives better.
- [25:53]
B
How did you know you'd be good at running your own business?
- [25:56]
A
I didn't, but I loved it so much. I mean, I really lived it, breathed it, woke up happy, woke up, like, because I really, I loved the content, I loved the people, and I still love the people that read the site to this day. I love running into the people who. I mean, this is helping people get an Edge, right? You know, your job may not pay you, but you can still go on safari. You can still take your family to Hawaii. I could have easily retired from the points guy. I'm still actively a part of the brand because we're still helping people. I truly get intense joy from that.
- [26:29]
B
Let's break that down because you sell the company pretty quickly after you started. What made you decide to sell so quickly?
- [26:36]
A
So I'm 28 years old.
- [26:40]
B
Let that sink in.
- [26:41]
A
I go from making 65,000 a year to 120,000amonth cash, no investors bought a $10 domain. My friend set the site up for free and then it was 200,000amonth. And so the first year I think I made two and a half, $3 million. I had some part time employees, four or five. And then a friend of mine, and this is also another tip I give people. I went on a date with this guy, didn't work out, but he was, he ran Yahoo Finance at the time and he was just very helpful. So staying in good terms with your exes could change your life like it did mine. And he said, you should meet this guy, Tom Evans, who's the CEO of Bankrate. Bankrate.com is a huge site for personal finance, mortgages. They own CreditCards.com and all these other credit card websites. He's like, I think the points guy could fit nicely. And at this point I'm like, I'm a blog. I'm a WordPress blog. No one's buying me, but I'll take this meeting. We have this good meeting. And that night he just messaged, I'm in the Bahamas now, but I want to buy your site. I didn't even have bankers.
- [27:43]
B
How did you even know what to price it at?
- [27:45]
A
It was interesting because yeah, it was one year of revenue at $3 million. I had to negotiate head to head as a 28 year old to this publicly traded company CEO who loved me. But it was also this. Negotiations get crazy. It is the biggest mind fuck where one day you're like, I'm selling my company. And the next day you're like, oh no. They're not responding because they're playing mind games. But at the end of the day, you offer me $28 million.
- [28:09]
B
Well, I just want you to say that again. $28 million.
- [28:11]
A
28 years old and they offer me $28 million for blog that I pay, you know, $10 for every single person I knew. All my entrepreneur friends take the money.
- [28:23]
B
Did you think of not taking the money?
- [28:25]
A
No, because I was like, this is. And granted, it wasn't like in one, it was a three and a half year earnout. So I was like, this is great. So I sold in May of 2012. I got 8 million that day. And then it was like three and a half and then, you know, five, five, five or something like that. So I'm like, great, I'm 28. I mean, I'm going to work till 31 and then like, I'll figure out the next step. And I have no, to this day, no regrets about selling because also so much of what Bankrate brought to the table finance. And we just started printing money and the business just kept growing and growing. It was life changing. It was like winning the lottery. I mean, I went through a lot of ups and downs with that. People come out of the woodwork. There's different dynamics.
- [29:03]
B
So about the messy, what was messy? Because it's all sounding really good right about now.
- [29:08]
A
It's messy. I mean, my group of friends at that time, I finally kind of found my gay group of friends in New York City. But they immediately resented me. And of course I bought a G wagon and I drove. I remember driving to Provincetown. I drove all of my friends up and I'm very generous and I'd never ask for money. And you know, I'm like, I just know how fortunate I am to be in this position. And I would pay for things. And the group of friends just were complete jerks to me and they would put me down. And that was the first stage of, oh, like my success. Now what many people will try to do and what I'm still dealing with in my dating life now is the easiest way for people to deal with their own insecurities about your success is to drag you down. So I put up with bad behavior because I was telling myself, well, I'm not going to change. I'm not going to let this go to my head. But I didn't realize that the people around me, it could go to their head. I had a best friend at the time. I bought a beautiful apartment in Miami. He was an interior designer and he totally took me for a ride. I paid for windows in my house. I've trusted him. Come to find out, everything I bought, he bought the cheap version and pocketed the difference. I sued him, I won. But then my lawyer billed me 10,000 more than what I won. So I was in this like loop of like, what is happening? You know, everyone's out to get me. Thank God for my parents. My parents are my Rock. I would not be in the position, still doing what I do today without my parents, but it was very mind blowing. Your life changes from every single aspect. But at the core level, I still love what I was doing. And what to this day still brings me down to earth is connecting with the readers of our site whose lives are materially better when they get into this game.
- [30:48]
B
I think one of the things that's interesting about your story is that you stayed with the company. A lot of people end up leaving after the earnout, but for you that wasn't a thing because you really, you are the points guy. Like, it is you.
- [31:00]
A
In hindsight, it's brilliant that I named the company the Points Guy. When I named it the Points Guy, by the way, most people were like, you'll never scale this, It'll never be more than you. You're going to have to do everything yourself. So many people told me that and I just decided to go with it. It's got a ring to it and it's probably the best decision I ever made because, you know, so after my earnout, it's 2015, the points guy's doing well. All of a sudden I'm getting traction in press where I'm becoming known. I'm going into our client meetings at Amex and Chase and people are lighting. And so I was like, me having a personality, building this brand has great benefits for the business because I especially now that I'm a fixture on tv, I was like, this is a very good superpower to have. So I signed another three year deal to stay on. I'm growing the points guy. 2016 comes around and we had this once again due to personal relationships. We had been working with Chase. Chase was launching secretly, their Sapphire reserve card first came out. We were their exclusive launch partner, which was extraordinary. That card was the biggest credit card launch in the history of credit cards. I would say, you know, it went viral, they ran out of metal. So we then were on top of the world. Because we're not just a blog, we're a media platform. We're not just an affiliate, but we're an affiliate with an influencer and a network of influencers. So I'm having a great time, everything's good. And then in 2017, I get a call one day, Bankrate publicly traded company which had been kind of been languishing. We're being sold, we're being bought by this private company, Red Ventures. I was on a film shoot in Cancun for a partner. I'm like, what? I was not involved in the management of Bankrate. They were like, be the points guy. We're working with everyone, but they let you be. I'm working for this company, making good money, no boss. Essentially, we're got a great startup culture. But Red Ventures was a much smarter company, more efficient. They had all these tools that really took TPG to the next level. But that was really challenging because they were based in Charlotte. I had to go back and forth to Charlotte a lot to integrate now into a new company, which presented challenges, but also it opened up tons of growth. We, we launched in the uk, we had a tech office in Austin. I'm trying to integrate with this parent company. And then 2020 hit, which was the best thing that could have ever happened to me because I was on a full course for. For burnout.
- [33:17]
B
Did you know you were on a full course for Burnout?
- [33:19]
A
I think I did deep down. But the way that I coped with it was just working more and throwing myself into it. It and go, go, go. And as I look back at my life, pre pandemic was chaos. I mean, events, events, planes. When I'm not in New York, I'm in Charlotte. I had a beautiful house in the Hamptons I never stayed at. It was all encompassing, being the CEO and then with a hundred some employees. I mean, I was in HR meetings all the time. It was always whack a mole. And I'm like, why am I doing this management thing? I'm not a manager. So 2020, when the world kind of stopped, it was the first time TBG ever lost money. But also, everyone knew, this is an opportunity. Let's reset. And I had a moment. You know, I talked with my parents. I'm like, do I quit? My mom was like, be an English teacher in our hometown. You know, like, come back to your roots. And I was like, I thought about it, but I talked to a lot of my mentors, and they're like, okay, you can have your moment, but don't be ridiculous. At the core level, I love doing what I do. I just did not love managing people in a huge corporate environment. But I went to the, you know, parent company, Red Ventures, and I was just like, I don't want to be the CEO anymore. And they were like, like, we've been waiting for you to say that. And that was once again another moment similar to leaving Morgan Stanley, where I was waiting for her to escort me out the door, like, you're out of here. You're quitting. And they were like, no. They're like, do what you do best. Do more press. Help us think about the future of the points guy. Be the cheerleader for the company, but don't sit in all the talent review that drains you. So that was like a major aha moment once again where I'm like, wait, I can. In my head it was like leave or this binary and it's dead that all these decisions that in our head we think are binary. You know, a lot of my friends, like, if I tell my boss I don't like my job or I'm looking, then they're going to fire me. I'm like, no. It might actually just promote a discussion. People are not mind readers, right? So I appreciate that they didn't push me out. And that opened up a whole new portion of my career where I decided to have kids, which is the best decision I've ever. I wanted to have kids in my 30s. So the pandemic, couldn't travel, started the IVF process. March of 2020. I broke off my engagement, moved to Pennsylvania, hung out with family, didn't travel, and kind of had a moment of like, what do I actually want in life? What I was doing was not sustainable for you, Covid.
- [35:34]
B
Like was really a moment of reset.
- [35:36]
A
It changed my life completely. And yeah, and it just opened my eyes. I really wanted to be a dad. I've always known I wanted to be a dad and, you know, understood it comes with its challenges. But I have a great family. Really, really, you know, solid group, small group of friends and, you know, the means to have help. I have two kids, almost three year old, and two boys. Two boys, Dean and Cooper. And they've changed my life completely.
- [36:02]
B
How?
- [36:04]
A
Funny enough, I thought about retiring again. I was like, okay, now I have kids, but I want to be just such a good role model for them and. And I need to be in a good mind space. I do not want to go back to working crazy amounts and being stressed, especially being a single parent. And also I get to travel the world. Now. Traveling with my kids is like traveling all over again and seeing the world through their eyes. And my youngest will be the youngest person to visit every continent. We're going to Antarctica later this year and Australia early next year.
- [36:35]
B
Very on brand for you.
- [36:38]
A
And my son Dean, I think he's been to 25 countries and traveling with kids is not easy, but it's so fun.
- [36:43]
B
Are you a planner? Do they say what's next for you?
- [36:46]
A
One new opportunity that opened up for me in 2020 when I was kind of home. I'd always been approached to advise and invest in startups and in the loyalty fintech space, there's so much innovation going on. I started taking meetings and one of them was with Encore Jain, who is the founder and CEO of Bilt. And he came to me with this idea like, hey, I want to create the first loyalty program for rent. It's our biggest expense for most people. I think I can do it. I helped him build Bilt, which has been an extraordinary over 5 million members, $11 billion valuation recently and just growing and growing. So that to me has a really fun way to not work hard but be mentally stimulated. So I have a bunch. Yeah, I basically have my own mini VC that I've started about five years ago and I've got a bunch of companies that have done really well.
- [37:35]
B
I mean, I think part of the reason I do the messy parts is because I feel like sharing the mess behind success is helpful, but also to do tips because I think there's a lot of people going through a lot of different things and I think it would be helpful to share our wisdom through a lot of pain and mess. What would you tell someone to do before they're 35?
- [37:54]
A
Take a really great solo trip.
- [37:57]
B
What would you say you'd never do again?
- [38:00]
A
I would never push myself to the brink of exhaustion.
- [38:07]
B
What would you tell your younger self?
- [38:09]
A
Keep exploring and in every bad situation you'll have, you will eventually realize why it happened.
- [38:20]
B
What's one piece of advice for someone who's looking for a job today?
- [38:24]
A
Understand the hiring managers. Understand where they're coming from, because that pulse can give you the edge. And tailor your first meeting around that, not around what you've done.
- [38:36]
B
What's a piece of advice you would give to somebody who's looking to pivot right? They're unhappy in a job or they're sort of mid career.
- [38:42]
A
Try things. You know, you can try so much while you're still working. Stop asking for permission.
- [38:48]
B
How messy, on a scale of 1 to 10 was your messiest moment?
- [38:52]
A
I think I've definitely had a 9 out of 10 messy moment.
- [38:56]
B
Okay, when was the last time you cried?
- [38:59]
A
It's nine months ago. But when my. Right before my second son was born, my first son was so excited about it and running around telling everyone, I just burst down in tears. It was like two days before the birth and it was just so cute.
- [39:12]
B
Well, thank you so much for coming. Honestly, this was as good as we all expected.
- [39:16]
A
Oh, thank you so much.
- [39:17]
B
And I love you as the superhero Wall Street Brian to Superher Hero Ryan.
- [39:21]
A
To Jetsetter thanks for making it to.
- [39:24]
B
The end of this Messy parts episode. Don't forget to subscribe. Drop a review and tell 10 friends.