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Founder's Story
Beyond the Miles: Brian Kelly's Journey to Creating The Points Guy Travel Empire | Ep. 171
00:21:09
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- [00:00]
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- [01:33]
Host
Hey everyone, welcome back to Founders story. Today we have an amazing guest. Today's guest 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. But let's, 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?
- [02:17]
Brian Kelly
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 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, 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 point 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. 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.
- [04:21]
Host
I mean, talk about scalability of coming up with the idea side hustle blogging every day. So it sounds like a lot of the secret sauce early on was consistency. 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.
- [04:59]
Brian Kelly
Yeah, I got lucky. So a friend of mine from college ended up working for what was called Link share at the time, which is now Rakuten. And Link share was affiliate marketing. So he pulled me aside one day and said, hey, you know, you're, you're talking about credit cards and you're linking to American Express.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 on the points guy 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 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 going to be anything substantial anytime soon. But once I got into affiliate marketing, I started using their links and you know, I was getting 2, $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, you know, 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 Kugel at the New York Times saying, interview request, 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 them. 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.
- [08:02]
Host
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?
- [08:29]
Brian Kelly
Yeah, I mean, there's. Their timing helps for sure, but you need to be relentless. Relentless. Like I, 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 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, you know, the big breaks were nice. But you know, I was able to capitalize on them because I had been blogging every day. Seth Kugel wouldn't have seen the points guy because most people start and lose interest after a week or Two. Right. You need to be committed, you know, 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 being like, I really want to 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.
- [10:11]
Host
I love the consistency. Relentless. I've for sure heard those things with other highly successful people like yourself. I'm curious on the, 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?
- [10:44]
Brian Kelly
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, 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 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 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 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, 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 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, et cetera. 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 sells 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 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 doing 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.
- [15:05]
Host
That's amazing. One of my mentors always told me, sell at the high point, because you'd 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 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, 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've 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 love to learn about your experience and what made you say, okay, I want to write A book now?
- [16:14]
Brian Kelly
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. Even if in luxury travel, you know, I highly recommend using luxury travel advisors. You're going to get the same price on the hotel, tons more in value, upgrades, perks, customer service.
- [17:14]
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- [19:35]
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- [19:55]
Brian Kelly
This is Taxes File for free with TurboTax Free Edition and get your maximum refund. No schedules except for earned income tax credit, child tax credit, and student loan interest. See if you qualify@turbotax.com free if something goes wrong at the hotel, you have a top dog travel advisor who can put pressure on that hotel to make it right. Because if they don't, those hotels need those luxury travel advisors. So when I tell people this, like, oh, why have I been booking on fourseasons.com directly? You're losing out on much more than just 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 like 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.
- [21:08]
Host
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?
- [21:21]
Brian Kelly
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 timeshifter is the game changer. Timeshifter will give you personalized recommendations 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 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.
- [22:21]
Host
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. 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, that you really love that stands out.
- [22:50]
Brian Kelly
Yeah. So. Well, 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, 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 Nippon 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 best business class.
- [23:43]
Host
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 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 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?
- [24:20]
Brian Kelly
Yeah. So my Instagram is at Brian Kelly and website for the book is how to win a Travel dot com. 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.
- [24:41]
Host
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 Founders Story.
- [25:19]
Brian Kelly
Thanks for having me. As they say, travel is the only expense that makes you richer.
- [25:29]
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