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- [00:01]
A
Brought to you by Capital One Business. When it comes to growing your business, sometimes you need more than financial investment. You need personal investment. That's what Jeff Plotner, Capital One business customer and co founder of Brackish, discovered after a unique groomsman gift in the form of a turkey feather bow tie grew into a successful men's accessory line. But when they were ready to expand, Jeff turned to his Capital One representative, Alex Parker, who who wasn't just an advisor, but a brackish customer. Because of the encouraging conversation with Alex, Jeff launched a woman's line, scaling the Brackish brand to the next level. Because at Capital One, it's not just business, it's relationships that help you do more business. Learn more@Capital1.com BusinessCards.
- [00:54]
B
Good afternoon. How's everyone doing today? Well, I want to welcome you all all to your next move produced by Inc and Capital One Business. And on behalf of all of my colleagues, I want to give a special shout out and thank you to Capital One Business for co producing this content series which is now in its sixth year. I believe it's been an incredible run and it is not just an event series, but it is also virtual events, a podcast, and other activities that bring vital information to founders to help you innovate and dream even bigger. So thank you to Capital One. Round of applause, please. And their partnership really enables us to convene events just like this one. I am really pleased to interview our next guest. Brian Kelly's love of trat of points began young. He was booking complex family vacations using miles starting at age 12, which is kind of incredible. And it really sparked an obsession with rewards programs. He was working at Morgan Stanley when he was encouraged to turn his passion into a blog, which later became a business. So talk a little bit about how you took this passion and turned it into a business.
- [02:19]
C
Yeah, thanks so much. Hi everyone. Yeah, this points thing, it was just two weeks ago. It was mid February 1996. My dad was a consultant in the 90s and he had approached me and said, if you can figure out how to use all my frequent flyer miles, we can go on a family trip. So when I was 12 years old, I had just read the book the Firm by John Grisham and it took place in the Cayman Islands. And mind you, I'm one of four kids. We grew up pretty middle class. We didn't have passports, but I was always that kid, watching all of my friends whose families were going to London for the holidays. I was actually so delusional. I remember Christmas time One year, my best friend was going to London and I was standing at the front door of my house waiting for his car to come because I thought in my head they were gonna surprise me and take me to London. But not a sob story, but they didn't stop for me that year. But I just have always been one of those people who's wanted to travel the world. Like when you spin a globe and you put your finger and you're like, I wanna go to Mongolia someday. I still do that.
- [03:18]
B
Been to Mongolia.
- [03:19]
C
Funny story, I have not. But not to humble brag, but Martha Stewart's like one of my favorite travel buddies. And we are going to go to Mongolia this summer. So stay tuned for that epic content.
- [03:30]
B
Are you bringing Snoop Dogg?
- [03:32]
C
You know what? I don't know if immigration and customs would let him in with what he carries with him. But anyway, so yeah, my love of points was forged in the 90s. And for me and my dad who traveled all the time, getting to take that family trip using his points once a year brought our family together. And that to me is the connective tissue to why even 16 years after starting the Points Guy, when most founders I sold the company 12 years ago, it got acquired again. Most people would have left and left to start something new. But I cannot begin to describe how much it still means to me when I get to talk to people in the airport who are excited. Frankly, people get to live better lives. So that little bit of joy I experienced in 1996 eventually was the seed that allowed me in 2010 to recognize I didn't want to spend my life at a cubicle in corporate America. But never in a million years did I think that it would grow to what it is today.
- [04:29]
B
I know we want to talk about your exit in a little bit because a lot of the founders here are probably thinking about an exit as a next move. But let's go back to those early days of of the Points Guy. What were the things that you tested and thought about when you were thinking about how you would monetize this blog and really turn it into something that was revenue generating and profitable?
- [04:53]
C
So funny. The Points Guy blog. My first blog post was June of 2010, but the points Guy as a business launched that April. So In April of 2010, the pointsguy.com was a Shell website. And I remember it was formsmarts.com it was a WordPress or you could just. It was a form that you could put in. I have all these points and it would email me and I would write back and say, yeah, I can help you. If you had 500,000AmEx points and wanted to go to Paris, I knew all the tricks to get you to do that. So basically my first job as a points guy was as a travel agent for points. So I would charge $50 a ticket, and that was just my side hustle. And I started spamming everyone on Facebook I went into to get clients for my business because I knew there was a market need. Everyone in 2010 had points, and no one knew how to use them. Airline websites were broken. So I thought, let me be the conduit to help people. So I actually went into my Gmail tip for startup founders. You got to hustle to do whatever it takes. I went letter A and I went through every person I had ever emailed. And then I created, I think this is against the law now, adding people to mailing lists. But I made an email. And this was right as Facebook was starting. There weren't even Facebook groups. So I was a travel agent for points. And then it was a colleague's husband that said, brian, this whole points thing you want to do, you've got a blog. So he set me up with the blog in June, and he said, just don't do any of this weird SEO stuff. Write rich content on the deals of the day, but you have to do it every single day at the same time to build up repetition. Most bloggers at that point in time were only blogging once or twice a week. So he was just, trust me, blog every day. And that's what I did. And soon the blogging and the audience started to grow. And it wasn't until the spring of 2011 I was making maybe a thousand bucks a month being a travel agent for points. But my life changed when a friend from college said, brian, this blog that you have that people are reading. He goes, I work at an affiliate marketing company called Link Share, which is now Rakuten. And he said, come meet me. I'm gonna show you all you need to know about affiliate marketing. And I met with him that day in Times Square, and it changed my life. Cause he basically informed me, you've got great content, a great audience, but stop linking to Amex and Capital One and Chase, and if you use our links, we'll pay you. And that's when my real entrepreneurial spirit started going. I had 50,000 monthly readers at the time, and I'm like, even if I convert half a percent of them at $300 in approval. So it started with like 5,000. The first month. And then my life changed when I learned how to harness the power of traditional media to drive traffic to the site. And Seth Kugel of the New York Times had written to me an email saying, all of my followers. So he wrote the Frugal Traveler column in the New York Times. He was one of those haters of frequent flyer programs. He was like, just don't even bother. And I would read his content, be like, this kills me because you're telling budget travelers, these are the people that need points the most to stretch the value of their trips. So I met with him for two hours, changed the way he thought about points, and at the end of that meeting, he booked a trip to see his girlfriend in Brazil. And he was on a New York Times writer salary. He was not making a lot of money. He could only go once or twice a year. But that day, I turned the value of his points that he thought were useless. He went into our meeting thinking, these are useless. There's, you know, just scattered around. But I showed him how to combine. And that day, he booked a trip, a surprise trip to see his girlfriend. And the moment his eyes lit up and he looked at me and was like, you've got to be kidding me, we actually booked it. So weeks later, he wrote a story that will forever change my life. It was the Points Guy, the travel website. Everyone needs to know right now. And at the time, I was devastated because it didn't make it into print. And in 2011, print, I wanted to show my parents and all these people who were kind of doubting me because many people said to me, you can't leave Morgan Stanley to start a blog. But it was the best thing ever to be online. Only because I got that juicy link back from the New York Times in 2011. And unbeknownst to me, that link back to the Points Guy direct, with the screenshot of my site giving me that credibility forever, launched the Points Guy on a rocket ship that is still going off today. In fact, the day the article came out, there was a credit card offer, British Airways, 100,000 miles. And the site went viral, and everyone was converting. I made 150,000 that day that the New York Times came out. And then I quit my job.
- [09:30]
B
See, news media is good for something. But I wanted to stay on that for a moment because I'm sure that there are a lot of founders out here in the room that are interested in earned media. In getting that story in the New York Times, did you contact Seth or did he contact you?
- [09:47]
C
Funny story. Founders Check your spam email. So I was traveling and he had emailed me and it went to my spam Gmail inbox and I was visiting a friend in Madrid. I remember the time and place I'm clicking through, going through my spam. Cause I also had clients because sometimes my client emails when I was a travel agent and my heart dropped. New York Times interview request. And I get goosebumps now thinking about it because I knew in that instant, like, if I nail this, this could change the trajectory. So that was incoming. But for all founders out there, press and pr, even traditional media has so much value in building trust. And there were a bunch of other points bloggers out there when I started. A lot of people call me the og and I appreciate that. But there were other points bloggers. I think my skill was taking my unique abilities in communicating with people and really getting passion out of it. And that was my moat is me. And while the company has scaled and we have so many different spokespeople in the press in the beginning days, like doubling down on media. And once I was in the New York Times and others, but it took many, many years for me to even get on the Today Show. I thought it was a failure. I think it wasn't until 2017. So now I'm on GMA, CNBC, but it takes a long time. But investing in good PR is critical. I just want to shout out Becca Manheimer. Raise your hand, Becca. She's our head of PR. She's been with the Points Guy for 10 years and she has fundamentally changed our business. So I still am a huge believer. And you need to be able to tell your story. Yes, in social media, but also with traditional media. Traditional media is not dead.
- [11:27]
B
Let's stay on personal brand for a moment because there is the points guy, the company, and then there is Brian Kelly, the founder. And many people who have interacted with your content via the Today show or some of those other earned media opportunities probably think that you personally are bigger than the points guy, the brand. How do you navigate the tension between personal brand and driving attention to the company?
- [12:01]
C
So it's funny. People still think I write every blog post. We've got 150 employees right now. We have a huge editorial team. And it's so funny. People will come up to me in the airport and be like, I love that review of China Eastern economy that you did. And I'm like, you think I fly economy long haul. I mean, I'm honored that people really still think I write a lot of the content people are usually blown away at the size of the company. I mean this is a real operation. We've got an incredible editorial team and I knew long, I mean I knew early on I needed to expand. It couldn't just be a gay single guy in New York City. Giving my perspective over the years we acquired there was a fellow blog Mommy points Summer Hole still at the points guy today and contributors we had lots of people from different perspectives. But to your question of like Brian Kelly and the points guy, it is very interesting. I mean so I sold the points guy in 2012 to a company called Bankrate. So mind you, I was making 70,000 a year at Morgan Stanley in 2010. In 2011 I made a million dollars in my first six months of getting into affiliate. So my life is changing. I started hiring people and then In May of 2012 I was approached by the CEO. I had no idea I was not even selling the site and I had never took investors. This was bootstrapped because it was a $10 domain and my hustle. But in May of 2012, this company Bankrate a friend of a friend, actually a guy I dated who didn't work out. But another tip for everyone, especially entrepreneurs. Always keep that network tight, don't burn bridges and when you leave, if you're still at a company going to start something, do not go out guns blazing Twitter feed blowing up a company. Because so many parts of my story, I was catapulted by my relationship. So a guy I went on a date, didn't work out, used to be the head of Yahoo. Finance and said you need to meet this guy, Tom Evans. So I'm 28 years old, I had a blog that made a couple million bucks and eventually they basically said, we want to buy your blog. $28 million was the end price. And I took it and ran. And every entrepreneur I talked to today, people were like, well, do you regret doing that? And absolutely not. You have to put in my mindset. I was in credit card debt. I was struggling day to day, you know, living through the financial crisis. Yes, I was making some cash, but I started to get panicked because there were a lot of other bloggers. Once people knew I started to make money, There were probably about 100 new blogs that popped up in the point space and they started to do some idiotic stuff because in affiliate you can pump and get new, you get paid on approval. So bloggers were saying, cancel your card, get a card because it's what was good for them. Me coming from a finance world and working at Morgan Stanley. I'm like, this isn't going to last long because all these bad actors are going to ruin the whole thing. So when people say, why did you sell in 2012? You have to understand it was a completely different world and it was a life changing sale. And the cool thing about once again bringing it back to me and the brand is when I named it the points guy, a lot of my friends in tech were like, oh, that'll never work because it's only going to be you. And that couldn't be further from the truth. We've obviously scaled it, but for me and loving what I do, I didn't want to leave. So I've been able to attach myself to this brand as the points guy, as our face. The company will absolutely thrive without me. But it's been really interesting because it's, you know, rising tides lift all. And I don't think there's really tension between me and the brand because I only do things that will help the brand. And I think we, you know, with the new owners of the company, we have very honest conversations about how we protect the brand. And I really, Becca is my boss. Everything we do for the company is, is with the long term goal and that's why we're aligned. And that's why I joke, you'll have to pry me from my first class seat to kick me out of this spot.
- [15:44]
B
Well, with legs like that, you probably need to sit first class because I medical necessity. Very tall man. Brian. You mentioned that. So you initially sold to Bankrate and then Red Ventures is the current owner.
- [16:00]
C
Correct.
- [16:01]
B
What did that transaction taste like?
- [16:02]
C
So 2012, Bankrate.com, which is a huge personal finance site at the time, they own CreditCards.com and they saw the points guy as their luxury asset. That they could just, you know, 28 million to this company was nothing. They didn't even report it on their financials. And they made a great bet. You know, it, it ended up taking off. And in 2016, you know, the business just blew up. So out of nowhere. And they weren't the best run company. There were some. The CFO went to jail. At one point the stock was kind of not doing great. So one day I just get a call, I didn't even know it was up for sale. They said, this guy named Rick Elias is going to call you in 10 minutes. I was on a, on a film shoot actually in Cancun for a credit card part. So I'm in a suburban in Cancun and this guy Rick Elias calls and the only thing I could do is just Google, what is Red Ventures? Rick Elias. And the first thing that comes up, and you should all watch it, he has a TED Talk. He was on that flight that went into the Hudson. And it is. I get chills thinking about it. He obviously survived. And after that day, he had the three things that changed his life. And he kind of took Red Ventures to the next level to make some big bets. They bought Bankrate for one and a half billion dollars. What people don't realize is that the points guy was a huge portion of that. And so I meet with Rick and he's a great guy. They call Red Ventures the Google of the east Coast. They've got the huge. So the points guy. We were great at content and brand and pr, but we had horrible website, horrible tech, horrible digital marketing. And Red Ventures was, is in 2017, an incredible digital marketing powerhouse. They had proprietary tech that could drive brands. So they were doing this for DirecTV, for major brands like American Express. Their thesis was, if we buy the points guy, we can give the operational rigor to help take it to the next level. And that's frankly happened. And certainly going through transit, you know, it's kind of like I sold the company twice going through another new owner, new culture. I remember just telling my employees we were going to have to leave Gmail and go to Outlook. And there was an uprising in the, you know, we couldn't have our Frenchies in the office anymore, which was probably a good thing because we kind of had an out of control office with all these French bulldogs that were peeing on everything. So yeah, there were definite changes. But you know, the points guy is still owned by Red Ventures. And I always say if I'm not providing my value, so I have a contract to stay on. In 2020. I decided that managing 100 people, managing with a parent company in Charlotte. I was spending all my time flying back and forth doing management and hr. I was not put on this earth to sit in quarterly HR meetings and do daily hr. And I give credit to all of the managers out there. Kudos to you. But I basically went to them and said, I hate this tension of me managing the points guy versus Red Ventures. Let me just do what I do best. I basically said, I don't want to run the company, but I want to be the spokesperson. And it was a little risky. And they said, we have been waiting for you to say that. And so it was the best day of my life because essentially in 2020 I was able to transition to just doing what I love. Going on tv, doing reader events, doing events like tonight, spreading the gospel and getting people into our ecosystem and traveling and especially allowed me to have kids. I have a one year old and a three year old. My one year old just became the youngest person in the world to go to all seven continents. That was a fun little journey. So I feel like I get to and I still oh thank you. So another thing is after you get acquired is always have honest conversations with your acquirer. Sometimes we think so binary like it's either I'm going to sit, stay on and lead this or not. And I think there are a lot of different ways to work it that you know. But if you don't say what you want, you're not going to get it.
- [19:51]
B
Any other advice for founders who are thinking about staying on after they after their company is acquired? Do you think that you should give it a year? Do you think that were there lessons that you learned from having gone through that, particularly with red ventures that you think are applicable? Knowing that obviously every founder situation is a little bit different.
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C
The biggest thing I would recommend is understanding the HR policies, compensation, HR review because you know that will be the biggest shock for me. The hiring practices, the talent, what is their thesis? And that was a struggle for me for a while because I was able to hire and pay people differently and the new parent company had a different Charlotte centric mindset. I'm living in New York, we worked through it, but it was challenging. So if you're going to sell a business and plan to stay on, definitely dig in with hr. Talk to people about the comp cycle, the promotion cycle because that is at the end of the day. As a founder and someone who wants to see the company grow, you need to have control over the people you hire. If your hands start getting tied, that can be a challenge. So but once again just having the conversations and finding and being able to negotiate from the beginning. The thing is I think people sell a company and then give up all control and they spiral when they see decisions aren't being made their way. But there are often ways that you can come to common ground. But I think I would recommend everyone sit down with HR people and fully get that that process.
- [21:23]
A
Starting a business comes with a share of ups and downs which is why staying true to your vision is essential. A non negotiable For Romeo and Milka, Regali Capital One business customers and co owners of Ross Plant based restaurant in New York, Romeo and Milka took a leap of Faith when starting their own restaurant, gutting an empty space and building it from the ground up. Every pipe, every wall, every detail. But building from scratch came with a heavy financial burden, which is when they turned to their Capital One business card. With the flexibility of the card's no preset spending limit, they were able to spend more and earn more rewards while bringing their vision to life. Today, Ross's success is proof that with passion and the right support, it's possible to make your dreams a reality. Learn more@capitalone.com businesscards Great advice.
- [22:19]
B
You wrote a book, how to Win to Travel, which there are copies of it at the Capital One Business newsstand. Would you recommend writing a book as a way of building your personal brand?
- [22:30]
C
It was the hardest thing I've ever done and I have PTSD thinking about it again. But I absolutely do think to tell your story. But just understand the book business is tough. I'm not gonna sugarcoat it. It is tough. Tough to sell books. It can be humbling. I I know we have a huge social media audience. We have a million people that read our newsletter. So I thought I'd get to 10,000 pre sales. Click, click, click. I got the audience and it is hard to sell. So if you're doing it, I think there are many more ways to tell your story through social media earned media, you know, than writing a book. Because it's hard people. We get all of our information for free on TikTok your hacks. So to spend 30 bucks on a book, you might be shocked at really how hard it is. I'm proud that I did it. For me, it was really fun because I love these events. I love being able to talk to people, sign books, laugh and it helps me be better at my job when I get to interact face to face. We're all on our screens, but there's nothing like meeting people who are fervent fans of your company in person. And I want all of the people who work at the points guy to come to these events. See the joy. Even if you're a developer on our design team, when you see the joy that we can bring to people, I think it makes us better. So writing a book, don't do it.
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B
We appreciate the candor you are now an investor as well as a spokesperson for the points guy and reluctant book author. How has your lens on business changed now that you are evaluating prospective investments?
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C
So for me, especially being a parent, it's something I'm grappling with and all of you will who want to have families or have them is the balance. And being a founder, it's tough. I could not imagine, and I waited till I was 39, had sold the company before I had kids because I knew I wanted to be present. So I have so many ideas and seeing in traveling and all the friction and especially in travel, the tech stack that underpins travel is horrible. Airline websites, there's so much consumer friction. And I like helping solve for consumer problems through the points guy. But there are certain things that the TPG is never going to do. I don't want to start a new company from scratch and go through all that I did. So being an angel investor has been the best new hobby for a degenerate gambler like myself. Being able to put big bets on really smart people. Some fail and some, you know, in 2020, a month after I stepped down from running the points guy and I'm at home pandemic, I get a call. I had been getting a call from this guy, Encore Jane, who wanted to start a website or a credit card for rent. And I had just written it off. Never going to work. I know how credit cards work, but I had nothing to do and I had all this open time and I'm sitting at home and I get on a call with Encore and he tells me the concept. It wasn't called Built back then, it was called casa. And he begged me to advise. So I said, if we can make this work, it'll be huge. I doubt it. But Encore is just an interesting character. He's the most relentless person I've ever met in my life. If he's got 20 issues facing his business, some founders will go one by one. Or maybe Encore has 20 going at all time. Firing cylinder. So, long story short, Built has become a huge success. So I was able to get in, you know, on the safe note with that. And it's now 11 billion last summer and I think going to the moon, frankly. So even if all my other ones fail, as long as Bilt keeps doing well. But. But yeah, it's fun because I get to add my expertise, come into a strategy meeting, help connect, get a meeting with the bank and airline. Really tough things, but it's not stuff that I need to spend 30 hours doing what I can do and the immense value I can bring to my companies. So it's fun. And I always put some of my own cash. I get advisory shares and it's fun. Even a former intern, Michael Selfogel, is the CEO of Cardless, which are the top new startups. So it was Kind of cool. Cart Bilt just moved from Wells Fargo to Cardless, another one of my companies. And there's some other things going on there. So it's, it's kind of, it's a fun way to innovate without breaking my back.
- [26:34]
B
It's the Brian Kelly ecosystem. I have to ask the question because it's 2026 and everybody's talking about AI. How do you see AI changing travel?
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C
It needs to. Travel is broken at so many levels, you know, and airlines are using AI to charge you more. So there's a lot of innovation happening. There's a new site with Autopilot. I have no affiliation, I haven't invested yet, but it's going to automatically check all your flights and get you vouchers for the difference. I think especially with disruptions in travel calling, I mean, how crazy is it in 2026, so many airlines make you call and wait on hold for eight hours to do the most simple things that should be self service. So that's not just an AI problem, that's like a whole tech stage stack infrastructure. But I think on the points front, the points technology that everything sits on needs to be blown up. And I do think blockchain, stablecoin. There's ways that I think interoperability is what we need in points. Because still, 16 years after I started the points guy, the same problem exists. You all have points and are not able to use them fast enough. And there's billions in value locked in unused points that if we can figure out how to get into the ecosystem, economies will flourish, businesses will flourish, consumers will gain value. As we see the cost of everything go up. Like Seth Kugel, the frugal traveler, when I was able to give him, hey, buy a flight. But if you can use your points and miles that you have sitting out there automatically collected and you can save money, that's a win for everyone. So that's. Those are the type of ideas that I'm thinking because the travel industry really needs, you know, a whole new tech stack.
- [28:11]
B
We've talked a little bit about your journey as an entrepreneur, your role as an investor, your interesting experiences as a book author. What is the next chapter for Brian Kelly?
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C
The next chapter for me is continuing to do the points guy. We've got a lot of great stuff coming. We have a new CEO, Liza Landsman, who started last summer. We're assembling a killer executive team. We have our head of product came from JetBlue. We have a new CTO. So we are building. There's Exciting things coming for the points guy, we know that we need to help our readers redeem points travel better. So coming out with the new tech stack, I've always wanted to create the app that will track your points and let you redeem points. That ecosystem still fragmented. So I think the points guy. I'm staying at the points guy. I'm in a multi year contract, happy as a clam. I'll keep investing but I think I've got it kind of made. I get to walk my son to school almost every day and I still get to do exciting things like this. So I always tell myself if it ain't broke, don't fix it. Things are pretty good right now and
- [29:15]
B
I have to ask, would you ever write another book?
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C
I would do another book that's how to win a travel. I wanted it to be the book that you can read. And it's not just points, it's jet lag. It's how to overcome fear of flying, how to get money back from an airline. So it's very service oriented. I definitely think I'll write another book when I get to tell some of the crazy stories of my life. I mean I've been at the forefront of this industry of points. I call it the platinum age of travel. We're in this multi billion dollar industry. The airlines are now making more money selling points than they are airline tickets, airfare. It's really incredible what's happened. Credit cards are a part of our lives and we'll shout out even though I don't have employees that I manage at the points guy I've got a whole family office now and nannies and capital One venturex business card is my go to for all of my personal side of things. 2x on everything. Really easy to use those points but yeah, I think I'll tell my story. That was the one piece of feedback I really listened to. People were like we wanted to hear more Brian. And in my book because I want to just continue to be the expert. I love saving people money. I didn't think it was as important to be about me but I think my next one I'll lift the curtain back a little bit more in a
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B
couple years maybe Mongolia with Martha.
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C
Yes. I mean the Martha Stewart. I was in Greenland with her. She's a character. She's actually. Yeah, she's incredible. So yeah, I've had a lot of really fun trips even just as I want. We have a minute left. I want to. I was in Morocco last weekend. If you need a soulful getaway Marrakech is stunning. The desert, amazing food. It was just what I needed. So if there's one thing you take away from this talk, you can now fly nonstop to Morocco from New York and Dulles. Highly recommend. And the Mandarin Oriental there is fabulous and fraction of the cost which you're going to spend in a lot of other destinations.
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B
Great pro tip from a pro. Well whether you decide to write that second book or not, we're very excited to have copies of how to Win at Travel and so I want to thank Brian on behalf of Inc And Capital One Business. I want to also thank all of you for joining us for your next move. Please stick around for our next session with Mark Cuban. And starting at 5:30 you'll get a chance to meet Brian inside the newsstand and get a signed copy of the book how to Win at Travel during the Miles and Margarita Happy Hour. Thank you all. Thank you Brian.