Beyond the Miles: Brian Kelly's Journey to Creating The Points Guy Travel Empire | Ep. 171
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Hey everyone, welcome back to Founders Story. Today we have an amazing guest. Today's guest is...

does something that I absolutely love. And we're going to dive into that, all that. But Brian Kelly, you are the founder of the Points Guy, which I've been using forever because, you know, back all the way going to 2012 to 2018, I was living my travel.

off of points. And I can't wait to dive into your new book, How to Win at Travel. This is huge. Like travel is like the comeback thing. Everyone I know wants to be on travel. Well, let's kick it off. Before we go into all that and your book, Brian, how did you even come up with the idea? And then how did you get started with the points guy?

Yeah. So, I mean, I've been doing the points game since the 90s. My dad got a job for a startup and I was one of those 90s AOL prodigy internet hackers. You know, I was the internet guru in my house. So I started booking travel for my dad when he didn't have a secretary anymore. And then one day we realized he had points.

And in 1996, I booked our family all on points to the Caribbean. And I would do that every year. So in my little family, I was known as the points kid back then. And then, you know, fast forward many years, graduate college, working at Morgan Stanley. I was in the recruiting office traveling a ton. Like I would say 50% of the year I was in college recruiting, you know, spending a ton of my corporate Amex. So all of a sudden I had,

huge amounts of points. And I wasn't making a lot of money being at Morgan Stanley and from '07 to '11 during the financial crisis. But my points were really, some years I made almost as much as my salary.

As I did in the points that I was able to redeem for first class travel. So in 2010, I started a side hustle called the points guy. It wasn't even a blog at first. I was basically a points travel agent where I would just side hustle and charge people 50, a hundred bucks, help them book a trip using their points because they had no idea how to use them. So to them, it was like free thousands of dollars of value.

And then about a couple months into it, a friend was like, dude, you have to blog. It's 2010. He was an SEO expert. I didn't know what SEO was, but he set me up with a WordPress blog and said, just trust me. Just blog once a day, every day at the same time. You will build an audience. This is like a gold mine of an audience. And he was right in about –

Six months in the blog started to really pick up steam and, and less than a year after I started blogging, I quit wall street and, uh,

Started really making money through affiliate marketing and credit cards. And less than two years after blogging, sold it to a publicly traded company. And yet I'm still here nearly 15 years later with the company. So it's been quite an interesting ride. I mean, talk about scalability of, you know, coming up with the idea, side hustle, blogging every day. So it sounds like a lot of the secret sauce early on was scalability.

consistency, the fact that you don't even know really what you're doing. And I like how you said, you know, the person was just blog, right? Like how simple we think of a blog is today. Back then, that was like a big thing. How did you go from blogging

And, you know, creating traffic to then monetizing, because I think we see this a lot with social media. People start building a following could be equated to like, you know, traffic to a site, but it's hard for them to monetize it. Yeah, I got lucky. So a friend of mine from college ended up working for what was called, uh,

at the time, which is now Rakuten. And LinkShare was affiliate marketing. So he pulled me aside one day and said, hey, you know, you're talking about credit cards and you're linking to AmericanExpress.com and Chase.com. He goes, you are losing money. He's like, if you were to just use a link through my company, you could get paid. You know, we don't pay per click. You know, you got to have someone get approved, which is a really high bar. Not everyone's just like going to random blogs to get approved for credit cards. But

but on the points guide they were, 'cause I was talking about these amazing offers and people were clicking to get approved. So the first month, I was making a couple hundred bucks a month on like Google AdWords, I think that's what it was, had about 20,000, 30,000 uniques a month and growing, but it wasn't gonna be anything substantial anytime soon. But once I got into affiliate marketing, I started using their links and I was getting two, $300 per approval.

And it didn't take a whole lot of approvals for that to become substantial quickly. So the first month was like $5,000 in affiliate revenue, which has someone making 70 on Wall Street, you know, in my, you know, HR job. I'm like, wait a minute, that's like almost like tracking to be close to what I'm going to make in a salary and that's

The second month I made 150 grand because I found out how to leverage media. So the New York Times and a tip I give entrepreneurs always go through your spam inbox, you never know what you might find. And in my case, I found a month old email from Seth Kugel at the New York Times saying interview requests New York Times. And he was the frugal traveler columnist. He

He didn't believe in points. He would always tell his huge, huge audience, yeah, don't worry about those points. There's blackout dates. Just buy the cheapest flight and ignore it.

And that to me is like, that is, that's, you know, ridiculous. So I basically agreed to meet with him for three hours and I showed him the value of his points. He was able to book a ticket to see his girlfriend in Brazil at the time, which he wouldn't have had the money to do otherwise. And he was blown away. He's like, you and your knowledge in that brain just,

connected me with my long distance girlfriend, like I was his hero. And so he wrote this really amazing story about this new amazing website, the points guy, everyone must read it. And that happened to come out on the day that there was this big bonus on a on a British Airways credit card. So it was this perfect storm. And unbeknownst to me, having that New York Times link back,

completely changed the future of my site's SEO forever. And frankly, to this day, it gave me so much credibility that then spurred CNN to reach out. And I taught myself how to go on TV, which was nerve wracking. But I also realized to set myself apart from all the other bloggers, I'm going to be the media spokesman for our industry, basically, and get media trained and learn how to leverage earned media, you know, to build a really successful business. How

How much of this do you think and you know, we've asked this and other other interviewers have asked the same question when it comes to like skill set versus luck.

What do you think played into all of this and the timing of things? Or do you think like the success of entrepreneurship, does it really come down to the timing of things? What do you find when it comes to your success or maybe, you know, friends that you've had? Is there a commonality between the success of how they did it and how you did it? Yeah, I mean, there's their timing helps for sure. But you need to be relentless, relentless. Like I when I'm

When I was starting, before I had the big breaks, I mean, I remember going into Google, building an email list for my new business for, you know, hey, everyone, if you've got family and friends that have freaking flyer miles, don't know what to do with them, I'll help book your family trip for 100 bucks this summer. And I would type the letter A and go through my Google contact list and just select anyone who I think would be remotely interested. I mean, I was hounding people everywhere.

to read my content. I was posting on forums. Before Reddit, there was Flyer Talk, which was the industry for all the frequent flyer world. And yeah, I got a little bit of hate. Hey, you're self-promoting. So I think the luck and timing absolutely plays a role, but you need to have relentless thirst and excitement for your business because the big breaks were nice, but

I was able to capitalize on them because I had been blogging every day. Seth Kugel wouldn't have seen the points guide because most people start and lose interest after a week or two, right? You need to be committed even when you don't get a big break. So consistency I think is key. And most of the other bloggers, there were many other bloggers way before the points guide, but most were posting randomly a couple of times a week. And I remember going to their sites being like, I really wanna read more about this industry.

And most people I knew did not have the time to go down the rabbit hole of flyer talk. So I'm like, let me translate the best deals from this industry to a mainstream audience, to 20 somethings who are working full-time jobs in New York City and traveling who don't have the time

to learn the language of the forums. I love the consistency, relentless. I've for sure heard those things with other highly successful people like yourself. I'm curious on the exit and then the progression after the exit of you staying on. We've had some people on that had

a great experience staying on after an exit. And then some people that had a horrible experience staying on after the exit. So what has been your experience? And is there any tip that you've given to people when they ask you about, you know, if you exit and then you stay on after? Yeah. So in my case, it's really interesting because the business I sold is called The Points Guy and I was The Points Guy. So I think I had a little bit in my favor and I had a three and a half year earn out. So, you know, they gave me,

less than a third at close. And then I had to, for three and a half years, earn out the full amount. So I still had a lot of work to do. I sold the business, had a bottle of Cristal on a Friday and was like,

back to blogging Saturday afternoon, you know, like there wasn't like a big honeymoon period. And, you know, there was definitely growing pains of, I started the points guy because I wanted freedom. And those two years where I was just making, you know, 400 grand a month with like a couple of part-time employees and having that flexibility was amazing. But I also knew there was a bubble happening. So once everyone found out I was making money, there were probably 200 other blogs that just popped up. And it was like the wild, wild west of credit card affiliates.

And, you know, everyone says, well, why did you sell so early? You would have made so much more money, but you have to always understand. I really thought because all these greedy people were coming in trying to make a buck and hurting the credit card companies. They would say open and close credit cards, all these things that were like really bad partnership. I'm like, the credit card company is going to hate this.

Because if they look at the affiliate channel as a pool, and I'm a part of that, and there's all these bad actors who are just trying to make a quick buck, who don't understand. See, I came from the corporate world. I understood compliance. I understood the nature of like, these marketing executives at credit card companies are not going to stand for their jobs getting put on the line by these moronic bloggers, flouting the rules and pushing everything to the, you know, the grayest of gray areas. So when I had that opportunity to take a substantial

substantial amount of money off the table. Every entrepreneur I talked to was like, dude, take that deal, take it yesterday, sign it, go, you know, and this will just, and my dad said to me that this will just be your first deal. That took me a long time to even understand because it was such, it was like winning the lottery. And I thought I was a one trick pony. I told myself I got lucky right time, right place. But what I've learned over the years and that company,

The publicly traded company Bankrate that I sold to, they were great partners. They let me do whatever I wanted. So it was basically like being a startup. But when I wanted to move from a WeWork to our beautiful TPG first ever headquarters on Park Ave, they let me completely design out. We had Frenchies. It was like a tech company, free lunch. I mean, it was a really fun time. So we didn't have to be the stodgy

you know, parent company. And I think for founders, based on what your plans are, make sure you carve all of that out when you're doing the deal. So the money makes a lot of sense, but also carve out how you want to pay your employees. I needed to have highly motivated employees that would go out, get business and think of it as their own business. So I needed to bonus them as such. And so make sure that you're not going to sell to a company that's going to put your employees of which your earn out depends on

onto a much cheaper compensation scale because that's where conflict starts, where you feel like your hands are tied, you can't hire the right people, it's slow, etc. So you really need to think about what you negotiate in terms of autonomy. But at the end of the day, you can't think of every scenario. You have to shake hands, look the person who's buying your company in the eye, and just say to yourself, do I trust this person? Because there's going to be plenty of times you both could go legal if you wanted to, but

You have to trust the people you're working with. And I think that test, someone told me that when I was selling and they just said, do you trust these people? Because you're never going to fully have a contract that spells out everything. And I was lucky. They were great partners. And then in 2017, Bankrate was purchased by a company called Red Ventures, which I'm now part of.

And that was amazing because they brought in a ton of other incredible marketing skill sets that Bankrate didn't have. Bankrate was not the best in, you know, marketing and technology, whereas Red Ventures was doing that for a ton of other companies. So they wanted to start buying their own properties to supercharge them. So that I learned a lot during that. And and I think.

I've been able to evolve with the company, you know, so it's it's been a really interesting to think it's been 15 years since I started my first blog post and really changing ownership several times, but still being happy and growing the business. I think I'm a very lucky man. That's amazing. One of my mentors always told me sell at the high point.

Because you never know. And that's what happened to me. We didn't sell at a high point when people were interested. And then the company imploded later on. You never know. Like you're saying, you may never know the people you're going to deal with. But you also, to what you said before, you never know what's even going to happen as your competition, technology changes, and then you might become obsolete. But I love that you really thought of your employees. I don't think every founder focuses on their employees. They may focus on themselves and their exit.

But the fact that you took care of the employees and the employees were happy to go with you and you've created this culture going through, you know, multiple companies who then purchased them. I mean, that's great. And now you're in a whole new place in your life. It sounds like because you wrote this book, how to win at travel before you even talk about the book.

How is the process of writing a book? Because I'm currently writing a book and I'm like a year and a half in. And sometimes I think I'm not sure why I even started this. But I'd love to learn about your experience and what made you say, OK, I want to write a book now.

Yeah, so, you know, the site's very popular, but it's still very difficult to get a grasp. And travel has changed so much, even from the pandemic, which is crazy. We're now almost five years, you know, post-pandemic, but the travel industry changed dramatically and continues to at a much higher speed than pre-pandemic.

So I wanted to write a book that kind of brought people up to speed. 2025 travel. Here's how you win. Here's how people are making mistakes by having a travel strategy, you know, having the same credit card as they're using 10 years ago, booking through these online sites that no longer serve you. You know, the airlines have new rules like it's much, much better to book direct with airlines when things go wrong.

they can help you a lot better. And I see people making these mistakes based on an old system of travel. And they always come to me, how do I fix this? Well, fixing it is setting up a new way of thinking and a new way of booking travel.

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perks and money, but also leverage when things go wrong. So yeah, I wanted to write a book that's for beginner and intermediate, even expert travelers. I learned a ton writing this book, interviewing scientists, doctors, how to beat jet lag, conquer fear flying. I got a chance to interview Whoopi Goldberg. So for me, sitting down with Richard Branson, Captain Sully, writing the book, it wasn't just about regurgitating my knowledge, but it was making it into a fun story

That I do believe will save people thousands of dollars by just educating them where the pitfalls are, what to avoid and how to shift. So I'm excited for people to kind of see my view on the industry and where it's going. I couldn't imagine sitting down with Richard Branson like that. That is a dream of mine of a person I would love to sit down with.

By the way, I'm suffering from jet lag right now. I don't know if you have a tip. Do you have something you can tell me? The biggest thing about jet lag is you need personalized recommendations. There's no one like magic elixir. That's all BS. Jet lag is light exposure, full stop. So your eyes have two functions. It's to see and to regulate to your circadian rhythm. Hey, here's when the body should start this process of digestion. And this is when you should sleep. And this is your immune system. It's sending signals. So

It's all about understanding your circadian rhythm. Are you a night person, a morning person, and then making adjustments before and after your trip to adjust to light. That is how you dramatically decrease jet lag. And long story short, the app time shifter is the game changer. Time shifter will give you personalized recommendations based on where you're traveling, the time difference, the season, your body. And, uh,

So, yeah, it might be too late this time if you're home from your trip, but always before a trip several days, download TimeShifter and it'll start giving you personalized recommendations to start adjusting to your new time zone. Thank you. I need that. I just flew for the first time business class because I was thinking to myself, they had an amazing upgrade.

Like what you're saying, I do, I followed your site. I've gotten a few credit cards from your site. I followed a lot of, I've just started trying the luxury, like that whole thing that you just were talking about. When it comes to airlines, what's your favorite airline?

business class and then what's your favorite luxury hotel? Maybe it could be a group or could be a specific hotel that you, that you really love that stands out. Yeah. So I'll talk points wise. I think Hyatt hotels has probably the best loyalty program and you can transfer chase and built points over to Hyatt. So Hyatt is kind of like my, you know, in terms of loyalty,

And then airline business class, you know, Air France business class to Europe is fantastic. Their new suite is really spacious, great food, great staff. I generally don't fly the U.S. airlines business class. I find their seats to be pretty cramped.

service to be math food man. So I generally try to fly European or Asian carriers, Qatar Airways Q suites are fantastic. But I think the overall best business class is all in the pond airways, the Japanese carrier, they have what's called the room. And it's a really huge, spacious, private suite that I think takes the cake and that's business class. Oh my gosh.

I want to do that. That is talk about a perk that you have of the job, I imagine. But I'd love to try the ones you just said. I want to see a sweet one day. I'm inspired by you, Brian. I want to do the sweet and I'm going to send you a message with an image of me in the suite. But if people want this is great, by the way, people want to get in touch with you. So many tips. I mean, for sure.

People already know if you haven't been to the point sky, you have to go. But if they want to get your book, because it sounds like the book is going to be life changing, at least for me with, you know, I travel frequently. If they want to do this, if they want to get in touch with you, how can they do so? Yeah. So my Instagram is at Brian Kelly and the website for the book is howtowinitravel.com. You can get it wherever you get books, ebook. And I also narrated the audio book, which is a cool 11 and a half hours. So on your next flight to Asia, just let me T.

Teach you all you need to know about travel from start to finish, or you can do it to Europe on double speed. Well, there you go. I'm going to be sitting in business class next time listening to Brian Kelly, but I got there because of Brian Kelly. So Brian, this has been awesome. I hope everyone checks out how to win at travel. It is the greatest thing that I spend money on in my life.

before the day that I'm going to pass away, I'm going to look back to all the memories I had. And I think, I hope that all the money I spent was on travel because it is so life-changing and it's really been something big for me. But Brian, thank you so much for all that you do. You do all the millions of people that you've helped. And I can't wait for everyone to check out the book, How to Win at Travel. And thank you for joining us today on Founder's Story. Thanks for having me. As they say, travel is the only expense that makes you richer.

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