Founder's Story
Beyond the Miles: Brian Kelly's Journey to Creating The Points Guy Travel Empire | Ep. 171
Tue, 04 Feb 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 Avocado Green Mattress: https://www.avocadogreenmattress.com* Check out Indeed: https://indeed.com/FOUNDERSSTORY* Check out Kinsta: https://kinsta.com* Check out Northwest Registered Agent and use my code FOUNDERS for a great deal: https://northwestregisteredagent.com* Check out Plus500: https://plus500.com* Check out Rosetta Stone and use my code TODAY for a great deal: https://www.rosettastone.comAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
Chapter 1: How did Brian Kelly start The Points Guy?
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 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.
I can't wait to dive into your new book, How to Win at Travel. This is huge. Travel is the comeback thing. Everyone I know wants to be on travel. Let's kick it off. Before we go into all that and your book, Brian, how did you even come up with the idea of And then how did you get started with the points guy?
Yeah. So, I mean, I've been doing the points game since the nineties. My dad got a job for a startup and I was one of those nineties AOL prodigy Internet hackers. You know, I was I was the 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. 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.
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Chapter 2: What prompted Brian Kelly to monetize his blog?
So to them, it was like free thousands of dollars of value. And then about a couple of 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, 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 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 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 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 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 to get approved, which is a really high bar. Not everyone's just like going to random blogs to get approved for credit cards.
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Chapter 3: How did media exposure impact The Points Guy?
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 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 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, uh, 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 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 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
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 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. to build a really successful business.
How much of this do you think, and we've asked this and other interviewers have asked the same question when it comes to like skillset 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?
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Chapter 4: What role did timing and luck play in Brian Kelly's success?
I'll help book your family trip for 100 bucks this summer. And I would take 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 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 back to blogging Saturday afternoon. There wasn't 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.
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Chapter 5: What was Brian Kelly's experience after selling The Points Guy?
Take it yesterday. Sign it. Go. 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 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 people. 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're 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 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 going to deal with.
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Chapter 6: How important is employee compensation post-acquisition?
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