Transcript

Brian Kelly on Travel Hacking, Business, and Burnout | The Points Guy

From Ryan Hawk · Episode page · Watch on YouTube

· 50 min · 10,273 words · 110 timestamped sections

This is the full, timestamped transcript of "Brian Kelly on Travel Hacking, Business, and Burnout | The Points Guy", an episode of Ryan Hawk published December 28, 2025 (50 min, about 10,273 words). It mentions 47 people, works and ideas, including The Points Guy, Delta Air Lines, Chase, relentlessly resourceful, Google LLC.

What this episode is about

Brian Kelly discusses his journey as the founder of The Points Guy, highlighting his initial success in travel hacking, the challenges of managing burnout as the business grew, and the evolving landscape of travel points. He reflects on the relentless resourcefulness needed to adapt amidst changing trends, his early experiences with technology, and the impact of his travels on his family life.

Key takeaways

  • Entrepreneurship: growing pains disguised as nonstop chaos. Embrace the burnout; it means you're onto something huge.
  • Million-dollar side hustle: revolutionize travel, convince folks points aren't dead. Critics are just jet lagged.
  • From childhood '90s hacker to travel mogul: DIY tech skills can chart a course to adventure and profit.
  • Relentless resourcefulness is in the DNA, learned in hometown humility, fueled by Mercedes dreams and global aspirations.
  • Manifesting wealth is like air miles: fantasize about first class, but hustle to earn the actual seat upgrade.

Who speaks in this episode?

What is discussed, and when

  1. – 5:00: relentlessly resourceful, Bucks County, Pennsylvania, Grand Cayman, Learning Leader Show
  2. – 10:00: The Points Guy
  3. – 15:00: The Points Guy, Bankrate, Becca Manheim, Google AdSense
  4. – 20:00: The Points Guy, Dustin Kim
  5. – 25:00: The Points Guy, Good Morning America
  6. – 35:00: The Points Guy, New Hope, Pennsylvania
  7. – 40:00: The Points Guy, Cardless, Coinbase, Coinbase credit card
  8. – 45:00: Air France, Drake Passage, Emirates, King George Island
  9. – 50:00: Google LLC, The Points Guy, Chase Sapphire Reserve, Facebook

Notable quotes from "Brian Kelly on Travel Hacking, Business, and Burnout | The Points Guy"

  • When you start the points guy, could you ever have envisioned it could get as big as it's gotten.
    about The Points Guy · at
  • All right, Brian. Man, it's awesome to have you here on the Learning Leader Show. Welcome.
    about Learning Leader Show · at
  • 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…
    about US Airways · at
  • I grew up in Bucks County, Pennsylvania, kind of leafy suburbs of Philadelphia.
    about Bucks County, Pennsylvania · at
  • It's just a side hobby making a couple 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…
    about Google LLC · at
  • So do you own any of it? I do not own any of it. And actually in 2017, Bankrate was purchased by a company called Red Ventures and we were taken private. So Red Ventures, I'm a…
    about Bankrate · at
  • I got offered kind of a separate job and I loved my boss so much. Her name's Dustin Kim. I actually had her on this podcast. I love her so much. She's still she's the CEO now…
    about Dustin Kim · at
  • 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 Oh, that guy has really good tips. Let me go…
    about Good Morning America · at

Who and what is mentioned in this episode?

People

  • Brian Kelly (football coach) — Person · 3 mentions
  • Encore (founder of Bilt) — Person · 2 mentions
  • Paul Graham — Person · 1 mention · first at
    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 founder co-founder is relentlessly resourceful.
  • Becca Manheim — Person · 1 mention · first at
    So, I the press team, the head of PR for the points guy, Becca Manheim, she's been there for nine years. I joke she's my boss because we, it's really important to be, we are the, the trusted source of real proconsumer.
  • Dustin Kim — Person · 1 mention · first at
  • Michael Spelfogle — Person · 1 mention · first at
    Thinking boldly. Another one of my investments is a former intern, Michael Spelfogle, interned for me at the points guy in 2015. He's now the CEO of Cardless, which is one of…
  • Liza Landsman — Person · 1 mention
  • Seth Kugel — Person · 1 mention

Books & papers

Companies & orgs

  • The Points Guy — Company · 21 mentions · first at
  • Delta Air Lines — Company · 6 mentions
  • Chase — Company · 4 mentions
  • Google LLC — Company · 3 mentions · first at
  • Bilt — Company · 3 mentions
  • AOL — Company · 2 mentions
  • Learning Leader Show — Company · 1 mention · first at
  • Prodigy — Company · 1 mention · first at
    If you imagine like 1991 got my first computer, taught myself MS DOSs and I think in '92 or three we got Prodigy Internet and at age eight or nine I was the computer like…
  • US Airways — Company · 1 mention · first at
  • Google AdSense — Company · 1 mention · first at
    It's just a side hobby making a couple 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…
  • Bankrate — Company · 1 mention · first at
  • Red Ventures — Company · 1 mention · first at
    Own any of it. And 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. I don't…
  • Good Morning America — Company · 1 mention · first at
  • Cardless — Company · 1 mention · first at
    Michael Spelfogle, interned for me at the points guy in 2015. He's now the CEO of Cardless, which is one of the top, new neo fintech credit card companies out there. They just…
  • Coinbase — Company · 1 mention · first at
    New neo fintech credit card companies out there. They just launched a Coinbase credit card, Qar Airways, and now in 2026, they got the built business. So, the huge built, it's…
  • Emirates — Company · 1 mention · first at
    And stuff. But, yeah, I, commercial internationally, I would actually prefer to be on an Emirates jet to Dubai than paying 200 grand to be in a small tube, right? like flying…
  • Air France — Company · 1 mention · first at
    A small tube, right? like flying in the nice even to Europe, you can get fly Air France first class, which is my favorite. They pick you up in the airport, you don't even see…
  • Facebook — Company · 1 mention · first at
    Google, Microsoft, all internet advertising unlimited. So, we spend a fortune on, Facebook and meta ads and that reserve card is triple points unlimited and those Chase points are super valuable. So, I've Yes.
  • Florida Georgia Line — Company · 1 mention · first at
    Way for me to be the preeminent Brian Kelly. There's also Brian Kelly of Florida Georgia line, and I love getting DMs from him of fans I'll do anything for tickets. so yeah, I sit I There's several other Brian Kelly's. It's kind of fun to.
  • American Airlines — Company · 1 mention
  • Artsy — Company · 1 mention
  • Guinness World Records — Company · 1 mention
  • Lindblad Expeditions — Company · 1 mention
  • Royal Malewane — Company · 1 mention

Products & tech

  • Coinbase credit card — Product · 1 mention · first at
    New neo fintech credit card companies out there. They just launched a Coinbase credit card, Qar Airways, and now in 2026, they got the built business. So, the huge built, it's…
  • Chase Sapphire Reserve — Product · 1 mention · first at
    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…
  • Airbus A350 — Product · 1 mention
  • Delta One — Product · 1 mention
  • MS-DOS — Product · 1 mention

Concepts & topics

  • relentlessly resourceful — Concept · 3 mentions · first at
    What do you think of being relentlessly resourceful?
  • points and loyalty — Concept · 1 mention · first at
    To now. I feel like I'm a part of history and that like we're creating the new era of points and loyalty.

Places & events

  • Grand Cayman — Place · 1 mention · first at
    Is history. I booked the six of us in my family. My dad and three siblings non-stop Philly to Grand Cayman. My mom and I flew on his American Miles with a stop in Miami and we…
  • Bucks County, Pennsylvania — Place · 1 mention · first at
  • New Hope, Pennsylvania — Place · 1 mention · first at
    Definitely not cheap to run your own farm but like where is it? It's in New Hope, Pennsylvania, which is 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.
  • King George Island — Place · 1 mention · first at
    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 six nights, which to me is perfect. I'm ADD. I don't want to be on a cruise ship for two weeks.
  • Drake Passage — Place · 1 mention · first at
    Don't want to cross the Drake Passage for four days straight in rough seas.
  • JFK — Place · 1 mention
  • Oman — Place · 1 mention

Full transcript with timestamps

They offered me $28 million to buy this blog. But then I realized, well, I am also the business. Any CEO will know in that growth mode of your business. It's just nonstop. So, I basically burn out. When you start the points guy, could you ever have envisioned it could get as big as it's gotten.

I made a million bucks in my first 6 months. Were you still working a full-time job?

You made a million bucks on the side. People today will say, "Well, the points game's over. It's changing." Well, no. It's been changing forever. In 2011, people called points dead. The world is shifting, but just move along with it.

Do you still travel a lot? I do. I travel a lot, mostly for leisure now. I have two young boys. My youngest is going to be the youngest person in the world to visit all seven continents.

What do you think of being relentlessly resourceful? I'm a racehorse. Put me in the race. The younger generations are pegged as like not working hard, wanting everything handed to them. So, prove that wrong. All right, Brian. Man, it's awesome to have you here on the Learning Leader Show. Welcome.

Thanks for having me. 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. C 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. Uh I'm 42 years old today. born in 1983. So if you imagine like 1991 got my first computer, taught myself MS DOSs and I think in '92 or three we got Prodigy Internet and at age eight or nine I was the computer like system administrator for my family which is kind of crazy to think about. Um and yeah, so I was always on AOL Prodigy. Some of my first jobs were um in the classified ads on AOL. When eBay first launched in the '9s, you couldn't actually upload any items. So there were uh thrift shop owners posting for for people like me. I was a kid at the time on c on 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 sorts of like very internet first experiences uh just taught myself how to do everything um including booking travel.

And my dad had gotten a job for a startup 1995 and I start booking all of his travel for him because he, you know, had a secretary and then all of a sudden he's working from home from a startup based in California. We we lived outside of uh Philly. So I became his travel agent. He was paying me 10 bucks to booking and it took me like 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 can go on a family trip." And the rest is history. I booked the six of us in my family. My dad and three siblings non-stop Philly to Grand Cayman. My mom and I flew on his American Miles with a stop in Miami 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 uh I originally heard heard coined by Paul Graham, the famed essay writer and Y Combinator uh founder co-founder is relentlessly resourceful. I feel like that is apppropo for you when when you hear me say that. What do you think of being relentlessly resourceful?

Absolutely. So, I grew up in a middle-ass family. I actually thought we were like poorer than we actually were. I grew up in Bucks County, Pennsylvania, kind of 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 you know, when I was a kid and I would spin the globe and be like, "This is where I'm going." Like, I would actually research Oman and I've been obsessed with like this notion of exploring the world. Much more so than my three siblings or my parents really.

My parents have now become jet setters cuz I get to take them around the world. They just came to Antarctica with me.

Um, but we didn't grow up that way. And so somehow genetically I got this gene of I need to be rich and travel the world and and and it didn't just dream of that. I I I visioned it, you know. I I used to get the Mercedes uh I used to call Mercedes get all of their glossy uh pamphlets for all their new cars and I would cut them out and I had Mercedes all over my bedroom wall growing up. And so 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, you know, almost free, but I've always wanted to kind of live this larger life and points have been a way to to do that through travel. How much do you think we'll get to, you know, 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, you know, 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. And as I look back on my career, I never really felt successful at all these minor moments that actually were pretty pretty incredible. So, but yeah, I do believe that like just believing and seeing and that you you you know, you can achieve that is is an important thing for your for your psyche to just know and feel.

I uh I'm attracted to people who think like way too big, you know? But in their mind, it's not way too big. And in my mind, it's 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 or even like dreaming it could get as big as it's gotten?

I wouldn't say 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 10, five years of the points guy, I left Morgan Stanley. I'm making three million bucks a year. I've got very few employees, no investors. Life's good. And I was like, I this is another theme. Everything I told myself I wouldn't do, I end up doing. So I said, I left corporate America. I don't want to be managing a 100 people. I want to just have a small lean team and do this thing that I love. Um, and have the money to to live flexibly and I don't want to be, you know, reporting into a man. I like my independence. And, you know, 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. Um, so I did know that

uh the the other bloggers out there when I started people think the points guy was the first blog. There were there were plenty of other niche points loyalty blogs um you know really from the late 90s early 2000s. I started the points guy in 2010 and there were you know some titan bloggers who are still blogging today and and I for sure felt imposter syndrome but I saw that what they lacked was creativity points and miles are very clinical very few people were translating that for an audience and I knew that I had an opportunity to be you know 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 6 months after blogging affiliate marketing when I saw that opportunity and 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 you know and 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 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 to double and triple down on that strategy of building something that's more than just a blog. That's 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 yours and the points guy though becomes I told you before we started recording I felt like I was I was I was a fan of the band

before anyone else knew about it and there was this like 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. It's it's a Delta had won some awards and maybe you 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."

Yeah. Is now known. It's on a Delta airplane. So, you go from a blog to an empire and then you sell. I I'm just thinking like

was that a was that a an actual conscious choice to say I don't want to just be a blog.

Yeah. I want to I want to build an empire. Was that with the infusion of the the money and selling and them asking you to stay on board or what what was going through your mind at that point?

Oh 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 hundred bucks a month in, you know, 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 I made six a million bucks in my first six months of just blogging how I was but using links and no one else really in the industry knew

on the Were you still working a full-time job? 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 and you're you know I was 28 years old. But I just I was like, "No, I I knew that it was it was legit. I believed in it." You know, it did take a leap of faith to But 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. And I still I had no real money. I realized the more I wrote the more money I would make. But I hadn't seen a scent of it yet. So I quit. My parents actually lent me $10,000 just to pay my rent. And luckily I 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 like months of backay.

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 a hundred blogs that started over a couple 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, which so they were writing stuff like, "Hey, cancel your MX, cancel your Chase, cancel, cancel, cancel, and then get new cards, get new cards." Cuz as bloggers, we would get paid on new signups. But what I saw was this really bad business sense, very shortsighted greediness of other bloggers to kind of screw the credit card companies. And I'm like, just watching this all happen, I'm like, they're going to pull the the rug. So

that's why when I was approached in May of 2012 by Bank Rate, the CEO, I I wasn't that didn't even have my company up for sale. Didn't when they offered me $28 million to buy this blog, I kind of 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 than what I sold it for but at the time you you always have to remember what the landscape was coming out of the recession there were still a lot of weak indicators 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 frank a cut of the business to grow it as CEO. So it was a it's kind of crazy to think you know 15 years after or no 13 what yeah 13 years after selling 14 almost that I'm still here but because I built myself as part a core center part of the business as the points guy I've been able to stay on with the less of the risk of the business going up and down getting paid well to do what I love so it's

so do you do you own any of it? I do not own any of it. And actually in 2017, Bankrate was purchased by a company called Red Ventures and and we were taken private. So Red Ventures, I'm a Red Ventures employee. I don't manage a single person, not even my executive assistant, which is like the dream scenario for me.

Um I kudos to all the people managers out there. That is uh just something I realized, you know, I love teamwork, but like real people management, mentorship takes so much time and effort. And I'm more of the brand visionary, the consumer person. So, so yeah.

So, 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?

So, I you know, the press team, you know, the head of PR for the points guy, Becca Manheim, she's been there for nine years. I joke she's my boss because we, you know, it's really important to be, you know, we are the, you know, the the trusted source of real proconsumer travel in America. 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. And so, you know, I don't sit in the I I will sit in our strategy meetings more of our, you know, where do we take this brand? What are the products consumers want? Because I'm still very plugged into what where the consumer is today.

Um, I 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 longtime clients or pitching new ones, you know, that's really where my special sauce is used and not in the day-to-day.

Do you do you still travel a lot? I do. I travel a lot mostly for leisure now. So, that was I have two young kids. So, that was So, in 2020, I had a sort of breaking moment. The 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. Any CEO will know in that growth mode of your business, you know, it's just non-stop. 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. So, uh I had this breakdown where I thought I would actually leave. It was the pandemic. I'm like, "Travel's down. Who knows when it'll come back? Is this my sign? It's been 10 years. It's been a great run." But, um, I went to the, you know, the the owners of the Points Sky,

you know, our 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. So, it was this aha moment of, wait a minute. And I think in life, we we often think so polar, you know, 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, you know, a heads up." I had given them several months. So that's a piece of advice I give to people. Uh you know, you know, your your 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, um, this role

is just killing me." More often than not in my career, the more, you know, vulnerable I was saying, "Hey, look, how can we work together to make this work for both of us, um, it has turned out to be such a blessing." And so they Yeah,

that's great advice because I I know I had this in my when I was working working in corporate America and I I was I got offered kind of a separate job and I loved my boss so much. Her name's Dustin Kim. I actually had her on this podcast. I love her so much. She's still she's the CEO now of a company in New York actually called Artsy. And and I remember I I and I left her because it was this giant promotion to be a VP at like a sister company. 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 like, well, I don't know. I thought it felt kind of weird being like super ambitious or 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 tell me we 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 kind of given my word and accepted that offer." And it's it was a I was just like, "Oh, it sounds so basic, right?" Like, "Well, just tell them what you want." But but it it seems like in your case just being honest and 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 kind of earns you those conversations to just be as real as humanly possible and let them know what you're thinking and how you feel.

Totally. Yeah. I I cannot stress that enough to people and and also what I'll you know remind people is I had some employees and whenever employees come up to me now leaving the points guys 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 on X roasting your company is the dumbest thing you could do. 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 is the only way to do it because uh yeah burning bridges on your way out may feel good for like a day but it will come back to haunt you.

I do want to focus I 100% agree. I do want to focus on inflection points and moments. I love specific moments in people's careers and and you it seems like you have like a very good memory of these moments as everything I read online and and now talking to you about it. But was it the New York Times when they reached out? Uh what was it that that took you from this blogger who was doing a really good job and had like a solid audience to then the this kind of rocket ship upward arrow growth that 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 like a very entrepreneur like so the New York Times Seth Kougall 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 but I knew my and um you know 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 you know is is branding. Um so that those were definitely inflection points and it was because I was frustrated in the media in 2011. It's funny because people today will say well the points game's over. It's changing. Well, no 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 dates, frequent fly 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 the world is shifting, but just move along with it is is the message. So yeah, 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 you know Instagram had it hadn't even started when I started the points guy 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 into I do in my hotel reviews, I'll stand underneath the shower and do

my TPG shower test, right? Where you know, just to see if I can the shower head actually clears. So, all these funny cheeky little things. But like, you know, I also saw like this is the Kardashians America. Like reality TV is what we watch and people want to know who they're supporting. So I I I viewed all of that at in real time like, oh, this is my opportunity to kind of be the face of this industry.

I think people want to follow people 100% more. 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 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 like a bigger scaling type thing. And I just don't I'm kind of 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 years and then I meet them in person and they feel like they know me. It's I go be it's because you do.

Yeah. You do. You've 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 to say, "Hey, Brian, it can't be about you or the points guy. It's got to be about the the bigger scaling things that you have to do." And I don't know, I just love to hear you riff on that because I this is something I think about and I'm working through as we speak of personal branding, bigger branding, building something bigger than than yourself even though you still want to show yourself. because that makes it more human and real and and and connectionbased with the people who are following.

Yeah. I mean I think the points guy there will be an interesting case study. Um because I mean 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 write you know 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 start, 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, you know, a Yeah. college grads. I mean, we hire college grads who have no points in miles or finance experience for that reason. and then they can talk about getting credit cards. You know, I'm a 42year-old, you know, wealthy man with the perfect credit score and connection. So, like having the experience of someone that you can relate to. I mean, that's 101 of building an empire. So, yeah. I mean, it's it's interesting. The site is uh people still associate so much of the site with me when most of what is created is not just me. If you look at our social media, I mean, I appear in videos and tent polls and but like there's tons of other, you know, uh, spokespeople as well. Even in media, we have, I think, 12 other media spokespeople now beyond me. So, we, while I may be the one that opens the

door for new outlets, but, you know, we have a whole group of other people doing it as well. So, um,

was that hard initially like because they trust you, they like you, they want you.

Sure. in the very beginning when I was just overanalyzing every decision um you know and I and I would and people will tell you know and when I was CEO up until 2010 I mean I still read comments emails and you know I would chime in on Slack when there was a mistake in an article as if I wrote it myself because I'm like this reflects on me so when we write I remember so vividly you know in a very viral post at the time we had the wrong capital of like of Norway it was like Reikuic the capital of Norway and I'm like to me as a geography buff I'm come on. And people are like, "Calm down. It's a simple mistake." But I was just like, I I I do take the, you know, integrity of this site. As we expand, we can't forego quality. So, and of course, you're going to So, yeah, I think that's something you always deal with. But I learned pretty early on to trust, hire good people, trust them, but always keep

an eye on, you know, if I think as if I look back at my time as CEO, I was a tough boss because as a founder, I still,

you know, it's so personal, right? It's 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 like 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 and I think my in hindsight I didn't highlight enough of the wins. I would focus too much on mistakes. And that's advice I would give if I could do it all back over again is to just be much more because as a you know as a human we like to get you know it's it's much more positive reinforcement over negative. And so to founders out there who are scaling like you need to check yourself and have someone around you a leadership team someone that can check you. 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 you know the business by all external metrics was booming for so many years and I think you know making sure you have good people on your team that can be honest with you and you create it's about you creating an an environment of like inviting that feedback and not freaking out when they give it to you is

important and that's something I definitely would think about as if I, you know, did did it again. I know I would be a much different CEO today, but um

we need we need truth tellers, man. We all do. 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 of a of a really thoughtful, intelligent person like you who's built something like 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?

Well, 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've just hired a bunch of senior executives. we're kind of taking TPG into a really exciting new place. Uh so I am involved in those decisions. So I interview people quite a bit and I'm and I'm I'm not the final decision maker. They don't report to me, but we are we are all a team at the end of the day. So I think I think during the interview process, it's too everyone is BSing way too much. Something that I've liked 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 and you know, we have this whole, but I think far too many senior executives walk into positions and they're like, "Oh, wait a minute." So, I

like to be not brutally honest. Of course, I'm still a brand person. And I'm not going to completely just focus on the negative parts what they need to come in. But I think like truthtelling in the interview process is the beginning of like having a great relationship with someone because I want you to understand exactly what's in front of you. And if you don't want to take it, that's so much better than hiring a senior exec that's 6 months later. Then you're six, you just lost a year. Um and and for me in the interview process, it's stop telling me the wins cuz 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 cherrypick the data that made their it's like really just diving deep into vulnerable moments about their leadership, the challenges as leaders

they had with their teams. I'll tell them my challenges when I was CEO. Like I want people to be real and allow me to understand like how they think the type of leader they are. Not just like we launched this new website and it was twice as good as the old one and blah blah blah. You know,

they they let's say they're willing to be vulnerable. They're willing to to you can you can feel that they're telling the truth about

wins, losses, everything in between. Yeah. What are some other things? Is it do you use your gut intuition to be like, "Ah, I really like her. I like him."

Yeah. That's gotten me in trouble in the past. I think Yeah. You know, just obviously because the problem is very charismatic people can can trick you easily, right? And

I think I've been blinded by a great, you know, especially when you're exhausted as a CEO and then you go into an interview and you're like, "Oh." And then someone's like bantering with you. You're like, "Oh, that was fun." Right? But the problem with that is I've hired plenty of people who are all talk and when you dive deep they you know they're I don't want personality hires. I'm the personality you know like uh or at least in certain roles in a sales role personality role might be higher but like my engineering team like I really need people to ship you know updates. So I um so yeah so it's really tough. I think interviewing is one of the hardest things because you want someone to be vulnerable, but um you really can't verify a lot and even with checking references nowadays, you you kind of have to you uh at the end of the day, you do have to go with the gut gut feeling.

Yeah. Um I want to think about you envisioning being wealthy and having a Mercedes. Um, now that you've got all that, how does it feel?

I still wake up in the middle of the night cuz, you know, I I'm like, do I are my bills paid? I'll be cuz, you know, I have several homes and there's a lot going on. Two kids, I've got nannies, I've got a whole team now of, you know, I don't manage any employees at the points guy, but I have, you know, 10 employees that work for me personally as I'm building, you know. So it's like so sometimes it's amazing though to be able to know I still have to tell myself it's okay like even if I stop working tomorrow I don't have to work ever again because I've made good decisions and like I still sometimes have imposttor syndrome about is this is this crazy what I you know like you know what I built it's not about the car or but I will say the homes I investing in a home that's beautiful and makes you feel really good is important. And I think for a long time I was traveling a lot. I never didn't really put roots

down and I always felt like I was in transit and now I think I have this beautiful farm with animals and horses. I started riding horses in the pandemic. I have this farm that like is it takes my blood pressure down immediately. I can walk. I can spend time with my kids. So I think investing and it was it's definitely not cheap to run your own farm but like

where is it? It's in New Hope, Pennsylvania, which is beautiful town about an hour and a half from New York City, an hour north of Philly. My family lives there, so my my two brothers and parent, that's where I grew up. So having that, I think that is like what I highly recommend. And get a designer to do things correctly. I'm still kind of cheap in a lot of ways. So I would buy my own furniture and I'm shopping online. at the end of the day like hire professionals to do and make your home really comfortable, your office, you know, so invest in the things I I think investing in a home that really makes you feel grounded is an amazing investment.

Why um as you said, you don't need to really work anymore. Why would you start something and then have to have 10 employees and go through all this with investing in others? Like why why do all that? Well, that's an interesting. So, I 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 March, 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 printing money printing machine from essentially the beginning. So, we're losing money, travel, and um I moved outside the city and realized I wanted just a different mentality. I didn't want to just be hustling. So, you know, kind of 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. Um they were readers of the points guy, you know, and they kept bothering me to be an investor and adviser in this little newsletter. And I I did. And it was a 10x investment over like two years. And I helped them because what they were building was very similar to what I built at the points guy, a small media company built around a passion. So, but I a lot of other people had approached me and I just never had time. I was too busy. Um, and I didn't want to, you know, invest my money in these startups. I just didn't have the capacity. So, in 2020, I wasn't working the same sort of chaotic travel schedule. So 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 in relevant companies. And the 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 kind of put it off. and it was like April of 2020 and 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, you know, 11 billion valuation and just skyrocketing.

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 I don't you don't need to put in the crazy amount of effort that I put into the points guy, you know, now being an adviser. So, I have probably about 15 other companies. I put my personal money in and and I love it because I can help advise founders on everything I've done, help open doors, give my comms, I know every influencer using that to build wealth for is is really it's it's kind of, you know, angel investing has basically become an addiction. I could see how when you see some of those returns. I I could see why. It makes a lot more sense now.

And and not all of them. I've definitely had flops, you know, always will, but I feel really good that there's I mean, once you have one mega one like built

Yeah. It can make up for a lot of flops. Yeah. Yes. So, you spent so much time around in addition to yourself, but so 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, relentlessness is the first thing that comes to mind. So, Encore, I am amazed at his ability to just, you know, if he's got 10 major things impacting his business, most CEOs will start with like one or two, put the others on the back burner. I mean, he will relentlessly push for excellence and his team and I that's why I like investing. I don't want to work for Encore. I mean, but to be in the room and to strategize and every time I leave a meeting with him and hey, let's go do this. Let's go launch these new cards.

What do you like that to me is exciting and it it keeps me fresh and active. So, back to the question of like I could retire, but I love it. I'm I'm a racehorse, right? Like, put me in the race. I don't want to just be hanging out in a pasture, right? I don't want to be racing seven days a week, but it still feels good to like, you know, be put into a racetrack with other top, you know, and to and to, you know, be pushed. So, um, yeah, and I I think thinking thinking boldly. Another one of my investments is a former intern, Michael Spelfogle, interned for me at the points guy in 2015. He's now the CEO of Cardless, which is one of the top, you know, new neo fintech credit card companies out there. They just launched a Coinbase credit card, Qar Airways, and now in 2026, they got the built business. So, the huge built, it's going from Wells Fargo to Cardless. So, that's a really cool moment for me as an

investor adviser and two businesses that are now coming together to do amazing things. Um, that that is very exciting to now. I feel like I'm a part of history and that like we're creating the new era of points and loyalty.

Um 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. You know some of my friends going around like well man if I did what Jeff Bezos did I would just chill and now he's like the co-CEO of a new company and he's sending rockets and Elon Musk and like you're not able to do what you've done Brian the points guy. you're 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'm not I don't think that's a bad thing. I 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 I just don't think that's possible.

Yeah. For me, I definitely have scaled back. like I work from home. So my two my biggest priority is I have two young boys, three years old and and one. My youngest is going to be the youngest person in the world to visit all seven continents. Uh we just I just took them to Antarctica with

Is that like in a Guinness Book of World Records? Yeah. Yeah. He'll be 12 months and 10 days. And for years the record was three years old. Just recently an 18-month-old broke the record. I'm like sorry buddy. So my son will be a year old. Um which is just like a fun thing we did. We I didn't even set up to do it, but you know, I love to challenge myself. So, but I'm home. I I really, especially, you know, 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, you know, especially cuz I'm a single dad. So that's a decision I chose to have kids on my own and um I'm very aware of like I don't want to have kids in this world as a single dad and then not be present for them. So

that's pretty wild man. Like what made you want to do that? I've always wanted to be a dad. It's like one of the universal truths I've known about myself for many years being gay. I was like oh it's not possible. And then um you know I always knew I wanted kids but you know the business I always put the business first. the jet, you know, I and from, you know, 2010 to 2020 when I was CEO of the points guy jet seting around, sold the business essentially twice, built a brand, I put everything. I was not going to be a good father during that that time. Um, 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, you know, my

lifeblood. I could probably write a book just on on nannies and and finding the right one. But I'm so happy I did it and didn't wait for someone else to unlock this, you know, life dream of mine.

Wow. Uh, that's wild, man. Um, you probably get asked this one all the time, but I'm still going to ask it anyway. Where are your favorite current places to travel?

So, I just recently went to Antarctica. I'm a big nature outdoors. I love being in places where you feel completely like on a different planet. So, um, 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 six nights, which to me is perfect. I'm ADD. I don't want to be on a cruise ship for two weeks. Don't want to cross the Drake Passage for four days straight in rough seas. So, this to me was like an ultimate trip. I took my parents and my kids because the seas are not bad. Antarctica was like a wow, I get it. Like if you're into art, like there's no better art museum in the world than an Antarctica.

Um it was just really powerful. I also love South Africa. I if you need inspiration, if you want a beautiful trip of like safari, Royal Malawan is like I went there this year. Unbelievable safari. Cape Town wine country. It's the ultimate sort of like soul soul uh refreshing trip for me. Um

you got uh Okay, this is a projection of my situation. You got 3.3 million Delta miles diamond. How how are you using them?

You know, so unfortunately Delta's of all the airlines are great airline, but their loyalty program is challenging. Those 3.3 million might get you to like Dayton and back, but uh no, they're not that bad. Delta actually does a good job. They run specials all the time. So, recently Delta this week, you know, they they they'll run specials like 100,000 points each to fly Delta 1 to Australia. They just launched a bunch of new routes, LA to Melbourne. And uh so I would like look to see whenever Delta runs these specials. I love their their new uh A350 suite. They also fly non-stop Atlanta, Cape Town, and Joberg.

So, redeem to go to uh South Africa or Australia, I think, would be how I'd use.

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

Oh, yeah. Yeah. Do you Do you still fly commercial? I do actually. I think I would love at a certain and I I'll charter here and there, but it's still I'm still a deal seeker, so it's just it really rarely makes sense to unless I'm flying short distances around with kids and dog and stuff. But, uh, yeah, I, you know, commercial internationally, I would actually prefer to be on an Emirates jet to Dubai than paying 200 grand to be in a small tube, right? like flying in the

the nice even to Europe, you know, you can get 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. Like, so flying commercial and then paying for those VIPs, you know, in some countries it's like 200 bucks and you someone will meet you at the plane and take you through immigration. So, you know, it's much easier to like splurge, take take a helicopter to JFK, get a sprinter with your friends to, you know, those things can make the the friction of like commercial travel take it way down and still save way more.

So, you're still like trying to gather your own points and use your own points or no? Funny enough, I when I sold the points guy, I put into my contract that I could put a lot of company expense on my credit card so that I would get points. And all these years later, we're spending a lot of money. And uh anyone 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, you know, Facebook and meta ads and and that that reserve card is triple points unlimited and those Chase points are super valuable. So, I've Yes.

I'm still very actively in the points game and you know, my points like taxfree 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 how much money you have.

Actually, I have two more questions. I was going to have one. Uh, 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. Um, well, hopefully now, yeah, he would mess up my Google alert. So, you know, if he's out of the business now, it'll, you know, clear the way for me to to be the preeminent Brian Kelly. There's also Brian Kelly of Florida Georgia line, and I love getting DMs from him of fans like, "I'll do anything for tickets." Uh, so yeah, I sit I There's several other Brian Kelly's. It's kind of fun to

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

I would say find mentors. Um, for me, finding people even at a company where you might not see your future, find someone at that company that can give you that you connect with. Or if you're looking for a job, you say you need to leave a terrible company. Interview until you and 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 too much focus on like the line of work or the company or what the company's trajectory is. But like stop focusing on that and look at that manager or the 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.

you know, 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, you know, this the younger generations are pegged as like, you know, uh not working hard, wanting everything handed to them. So prove that wrong. And I do believe like 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. Like 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. I really like what they did." They are a future leader. Right? So if you're if you're on the verge of getting a promotion, you've got buyin because you're present and

there like that's how you get ahead. And then even if that boss leaves to another company, they might take you. So

this is such really really good advice. A little surprising coming from a guy I know you worked at Morgan Stanley so you you understand that element too, but from a guy who's kind of built his own business, but that is so useful. So uh really good. Uh Brian, where would you send us? I mean the points sky.com, but where else would you send us to learn more about you online?

Yeah, so you know the points sky, all of our social channels and website. I have a weekly newsletter there you can sign up for, but also my personal Instagram is Brian Kelly. B R I an ke- ly, not the others. And um and I wrote a book this year. Well, I wrote a book. I know this podcast might come out next year. And also I wrote a book, How to Win It Travel, which kind of gives all of my tips, little bit of my story. So, if you want to get into the points game and uh and travel the world for a fraction of the cost, I would highly recommend reading it or on audiobook.

Love it. Brian, thanks so much, man, uh for being here. I'm appreciative. You have a great team also that works with you, which has been great to work with. Uh I really appreciate and I would love to continue our dialogue as we both progress man.

Absolutely. Yeah. Thanks for having me, Ryan. Thank you.

Questions about this episode

Who speaks in "Brian Kelly on Travel Hacking, Business, and Burnout | The Points Guy"?

Ryan Hawk (Host), Brian Kelly (Guest), Becca Manheim (Guest), Liza Landsman (Guest), Dustin Kim (Guest), Seth Kugel (Guest), Encore (last name not provided) (Guest), Michael Spelfogle (Guest).

What is "Brian Kelly on Travel Hacking, Business, and Burnout | The Points Guy" about?

Brian Kelly discusses his journey as the founder of The Points Guy, highlighting his initial success in travel hacking, the challenges of managing burnout as the business grew, and the evolving landscape of travel points. He reflects on the relentless resourcefulness needed to adapt amidst changing trends, his early experiences with technology, and the impact of his travels on his family life.

What is mentioned in this Ryan Hawk episode?

47 people, works and ideas are mentioned, including The Points Guy, Delta Air Lines, Chase, relentlessly resourceful, Google LLC, Bilt. Each one on this page links to its own page with every episode that mentions it.

How long is "Brian Kelly on Travel Hacking, Business, and Burnout | The Points Guy"?

The episode runs 50 min; the transcript is about 10,273 words in 110 timestamped sections.

More from Ryan Hawk

About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated January 24, 2026.