Founder's Story - Beyond the Miles: Brian Kelly's Journey to Creating The Points Guy Travel Empire | Ep. 171

Episode Date: February 4, 2025

In this compelling episode of Founder's Story, Brian Kelly, the visionary behind The Points Guy, reveals how his passion for travel evolved into a multimillion-dollar digital enterprise. Brian details the strategic insights and relentless research that helped him decode the world of loyalty programs and travel rewards. With a focus on data-driven decision-making and customer value, he shares actionable strategies that propelled his brand to global prominence. Whether you’re a travel aficionado or an entrepreneur, Brian’s journey offers inspiration and practical tips for mastering both digital innovation and the art of travel rewards.Key Topics DiscussedFrom Passion to Empire:How a deep love for travel sparked the creation of The Points Guy.Data-Driven Decisions:The role of meticulous research and analytics in navigating loyalty programs.Digital Innovation:Embracing technology to connect with millions of travel enthusiasts worldwide.Value-Driven Marketing:Strategies for delivering actionable insights and building customer trust.Notable Quotes“Travel isn’t just about going places—it’s about unlocking opportunities.”“Every mile matters. It’s all about turning data into decisions.”“Innovation is the passport to staying ahead in a rapidly changing digital world.”Resources & LinksThe Points Guy Website: thepointsguy.comConnect with Brian Kelly:https://www.instagram.com/briankelly/https://www.linkedin.com/in/thepointsguyCheck out the article about Brian KellyOur Sponsors:* Check out CoinFlip and use my code FOUNDERS for a great deal: https://coinflip.tech* Check out Indeed: https://indeed.com/FOUNDERSSTORY* Check out Kinsta: https://kinsta.com* Check out Plus500: https://plus500.comAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

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to speak to an advisor free of charge. Bet MGM operates pursuant to an operating agreement with iGaming Ontario. Hey everyone, welcome back to Founder's Story. Today we have an amazing guest. Today's guest does something that I absolutely love and we're going to dive into all that. But Brian Kelly, you are the founder of the points guy, which I've been using forever because 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 in 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, you know, 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 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, 100 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. And about six months in, the blog started to really pick up steam and less than a year after I started blogging,

I quit Wall Street and 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 consistency. Uh, the fact that you didn'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 LinkShare at the time, which is now Rakuten, and LinkShare was affiliate marketing. So he pulled me aside one day and said,

hey, 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. We don't pay per click. You got to have someone get approved, which is a really high bar.

Not everyone's just going to random blogs to get approved for credit cards. But on the points guide, they were. Because I was talking about these amazing offers and people were clicking to get approved. So the first month, you know, I was making a couple hundred bucks a month on like Google AdWords. I think that's what it was, you know.

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, you know, 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 as someone making 70 on Wall Street in my 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 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 Google at the New York Times saying interview requests, New York Times. And he was the frugal traveler columnist. 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 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-racking but I also realized to set myself apart from all the other bloggers I'm gonna 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 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 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, timing helps for sure,

but you need to be relentless, relentless. Like 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 a hundred 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 to read my content. I was posting on forums, you know, 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 you need, you know, the luck and timing absolutely plays a role. But, you know, 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 Coogle wouldn't have seen the points guide because most people start and lose interest after a week or two. 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 got. But most were posting randomly a couple times a week, and I remember going to their sites and 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 you know 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 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 they gave me less than a third at close and then I had to for you know 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 you know 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 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 companies are gonna 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. I came from the corporate world.

I understood compliance. I understood the nature of these marketing executives at credit card companies are not going to stand for their jobs getting put on the line by these more ironic 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 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 in that company the publicly traded company Bankrate that I sold to they were great partners they let me do whatever I wanted so it's basically like being a startup but when I wanted to move from a we work to our beautiful you know 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 will 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 you know

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 gonna 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 gonna 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 a part of. And that was amazing because they brought in a ton of other incredible marketing skillsets 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 I think I've been able to evolve with the company. So 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 gonna deal with but you also, to what you said before, you never know what's even gonna happen as your competition technology changes and then you might become obsolete. But that's, 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 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, okay, I wanna 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 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 ten 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. Even if in luxury travel, I highly recommend using luxury travel advisors.

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based on where you're traveling, the time difference, the season, your body. And so yeah, it might be too late this time if you're traveling, the time difference, the season, your body. 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 business class and then what's your favorite luxury hotel maybe it could be a group or could be a specific hotel 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. I, 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 US airlines business class.

I find their seats to be pretty cramped, service to be meh, food meh. 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 in best business class.

Oh my gosh, I wanna 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 suite. One day, I'm inspired by you, Brian. I want to do the suite 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 points guy, you have to go. But if they 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 gonna 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 how to win a travel calm you can get it wherever you get books, ebook, and I also narrated the audiobook which is a cool 11 and a half hours so on your

next flight to Asia just let me 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 gonna 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 spent 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 changingu and it's really been somet

Brian, thank you so much you do all the millions o helped and I can't wait f out the book how to win a you for joining us today Thanks for having me. As the only expense that mak Get ready for Las Vegas style action at BedMGM, the king of online casinos. Enjoy casino games at your fingertips with the same Vegas strip excitement MGM is famous

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