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The Learning Leader Show with Ryan Hawk

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My Guest: Brian Kelly is the founder of The Points Guy, which he built from a side hustle blog into a travel media empire that he sold for $28 million. At 42, he's now an angel investor in 15+ companies, including Bilt (valued at $11 billion). In this conversation, he shares lessons on manifestation, selling too early, building yourself into the brand, and why vulnerability beats wins in interviews.

Key Learnings (in Brian's words)

In 1995, I was 12 years old, and I was great with computers, so I started booking all of my dad's travel for work. He'd pay me $10 per booking. Then it turned into points, when my dad showed me all the American and US Air miles he had. "If you can figure out how to use all of them, we can go on a family trip." And the rest is history. That was my first real, oh wait, this points thing is amazing. Points were a way for us to live a fabulous lifestyle.

I grew up thinking we were poor, but I really wanted to live a fabulous life. My parents were very humble and did not spend money lavishly. For me I always wanted to travel. When I was a kid, I would spin the globe and be like, This is where I'm going. I would actually research Oman. Somehow genetically, I got this gene of I need to be rich and travel the world. I used to call Mercedes, get all of their glossy pamphlets for all their new cars, and I would cut them out and stick them on my wall.

Manifesting alone won't make you wealthy, but visioning helps. I do believe being able to visualize what it looks like and taste it and get close to it helps you take the smaller steps to actually achieve it. When I think of my investments, I actually envision what they're gonna be. I envision that they're multi-billion-dollar companies. I believe it unlocks a level of pushing you to reach these mini steps that you can't see throughout the process.

I started The Points Guy in 2010, but there were already Titan bloggers. I for sure felt imposter syndrome, but I saw that what they lacked was creativity. Points and miles are very clinical. Very few people were translating that for an audience. I knew I had an opportunity. I'm in my twenties, living in New York City. I'm gonna explain what everyday people need to know.

Building a media brand became my moat. No one else in the points world was doing media. Doing media's frightening. While it was scary going on TV the first couple times (I almost fainted), I knew that each time I did it, I got better. That was the moat I would build. I would build The Points Guy into a brand more so than any of the others who had come before me. I saw from the beginning to double and triple down on that strategy of building something that's more than just a blog, but a lifestyle that people want to achieve.

"I made a million bucks in my first six months of just blogging, but using affiliate links."

In 2011, within six months of learning about affiliate marketing, I made six figures a month using the credit card links in my blog. I was still working at Morgan Stanley. My mom was like, this sounds too good to be true. You can't leave Morgan Stanley. I was making like $300,000 a month in affiliate. Meanwhile, at Morgan Stanley, my salary is $70,000 a year. But it didn't pay right away. My parents actually lent me $10,000 just to pay my rent. I remember where I was in Madrid when that first Chase deposit of $490,000 hit from months of back pay on the blog.

I sold for $28 million because I thought the industry would collapse. When Bankrate offered me $28 million in May 2012, I kind of had this negative mindset over where the industry was going. About a hundred blogs started when people knew they could make money on affiliates. Most bloggers have zero business sense. They were writing stuff like, "Cancel your Amex, cancel your Chase, cancel, cancel. Then get new cards." I saw this really bad business sense, very shortsighted greediness. I'm watching this thinking they're gonna pull the rug. Do I regret selling? Yes, the company is way more than what I sold it for. But at the time, you always have to remember what the landscape was. We're coming out of the recession. There were still a lot of weak indicators.

Building myself into the brand gave me leverage. I had a three and a half year earnout. Over that time, the business really started to grow, but then I realized, well, I am also the business. So, the more press I did, when I negotiated with that parent company to stay on, they paid me a lot of money and still a cut of the business to grow it as CEO. It's kind of crazy to think 13 years after selling, I'm still here. But because I built myself as a core part of the business as The Points Guy, I've been able to stay on with less risk, getting paid well to do what I love.

I'm more of the brand visionary, the consumer person. I'm very much an ideas person. When we're speaking with our longtime clients or pitching new ones, that's really where my special sauce is used and not in the day-to-day.

People are not mind readers. In 2020, I had this breakdown where I thought I would actually leave. I went to the owners, and I was like, I just can't do it anymore. They said, "Brian, we've been waiting for you to say that. You don't need to be CEO. We have plenty of smart people." It was this aha moment. I think in life we often think polar, black or white. That's advice I give to people. Whether it's your parent company, your boss, your mentor, people are not mind readers. While there is risk to leveling with someone and saying, "Hey, this role is just killing me," more often than not in my career, the more vulnerable I was, the more it turned out to be such a blessing.

Check Your Spam Email Frequently: In 2011, I was featured in the New York Times, but the email came to my spam email. At that time, the narrative that points were dead, blackout dates, etc. I was the only blogger putting a positive spin on points. And I tried to do it in an informative and fun way. I'm 6'7", so putting my personal angle on my travel reviews had a huge impact on being the face of this industry.

As a founder, I was a tough boss because it was so personal. If I look back at my time as CEO, I still took it very personally. I do take the integrity of this site. As we expand, we can't forego quality. In hindsight, I didn't highlight enough of the wins. I would focus too much on mistakes. That's advice I would give if I could do it all back over again, to just be much more positive reinforcement over negative.

Founders need someone who can check them. You need to have someone around you, a leadership team, someone that can check you. I didn't have that for a very long time, and that's my fault. Making sure you have good people on your team that can be honest with you, and you create an environment of inviting that feedback and not freaking out when they give it to you, is important. I know I would be a much different CEO today if I did it again.

Stop BSing in the interview process. Too many people take jobs not knowing what is going on whatsoever at the company. Far too many senior executives walk into positions and they're like, oh wait a minute. I like to be brutally honest in the interview process. Truth-telling is the beginning of having a great relationship because I want you to understand exactly what's in front of you. If you don't want to take it, that's so much better than hiring a senior exec and six months later, you just lost a year.

Stop telling me the wins. In the interview process, stop telling me the wins because anyone can make their job look successful. "Oh, 200% ROI, this, that the other." In an interview, you're not gonna be able to fact-check any of this. We all know people can cherry-pick the data. It's really just diving deep into vulnerable moments about their leadership, the challenges as leaders they had with their teams. I'll tell them my challenges when I was CEO. I want people to be real and allow me to understand how they think, the type of leader they are.

Charismatic people can trick you. The problem is that very charismatic people can trick you easily. I've been blinded by a great interview, especially when you're exhausted as a CEO and then someone's bantering with you. You're like, oh, that was fun. But I've hired plenty of people who are all talk. I don't want personality hires. I'm the personality. My engineering team, I really need people to ship updates.

I still wake up in the middle of the night asking if my bills are paid. I still have imposter syndrome about "is this crazy what I've built?" It's for sure not about the car, but I will say investing in a home that's beautiful and makes you feel really good is important. For a long time, I was traveling a lot. I never put roots down, and I always felt like I was in transit. Now I have this beautiful farm with animals and horses in New Hope, Pennsylvania. It takes my blood pressure down immediately.

Angel investing has basically become an addiction. In 2020, I opened up a space where I decided I wanted to have kids even though I was single, and also started investing and advising in relevant companies. The first one was Encore Jane, who was building Built, a credit card loyalty platform for renters. I'd always thought, how cool would it be to earn points on rent? I said, You're crazy, but if it does work, it'll be massive. Built is now at $11 billion valuation. I'll make more money now, probably on Built than I will at The Points Guy, which is wild to me. I have probably about 15 other companies I put my personal money in. I love it because I can help advise founders on everything I've done, and help open doors. Using that to build wealth has become an addiction.

Relentlessness is what I see in leaders who sustain excellence. I am amazed at Encore's ability to push. If he's got 10 major things impacting his business, most CEOs will start with one or two, put the others on the back burner. He will relentlessly push for excellence. I don't wanna work for Encore, but to be in the room and strategize, every time I leave a meeting with him it keeps me fresh and active.

Find mentors, not just companies. For recent college grads, find people, even at a company where you might not see your future. Find someone at that company that you connect with. If you're looking for a job, interview until you find that hiring manager that you feel is on an upward rise and that you can learn from. We often focus too much on the line of work or the company. Stop focusing on that and look at that manager or the CMO whose organization you would join. If they've done amazing things, get in right away and start networking. Put time on the CMO or CEO's calendar. Be bold. Every senior executive loves to see people come in with eagerness to learn.

Show up and do extracurriculars at work. Go to the lunch and learn with the senior executive and actually get face time with them. Make sure they know your name. Those are the things that matter because when it comes time for compensation and reviews, the senior person may not work with you day-to-day, but they're like, oh yeah, that's the person I really like. They are a future leader. That's how you get ahead. Even if that boss leaves to another company, they might take you.

Reflection Questions

Brian says manifesting alone won't make you wealthy, but visioning what it looks like helps you take the smaller steps to achieve it. What specific vision do you have for your future that you could make more tangible (like his Mercedes pictures on the bedroom wall)? How might making it more concrete change your daily actions?
He emphasizes that in interviews, he wants people to stop telling him the wins and instead dive deep into vulnerable moments about their leadership and challenges with their teams. If you were in an interview tomorrow, what's one vulnerable leadership moment you could share that would demonstrate how you think rather than just what you've accomplished?
Brian realized he needed to tell his parent company, "I just can't do it anymore" as CEO, and they responded with relief, offering him a better role. What conversation are you avoiding right now because you assume the answer will be no, when the other person might actually be waiting for you to speak up?

More Learning

#525 - Frank Slootman: Hypergrowth Leadership

#540 - Alex Hormozi: Let Go of the Need of Approval

#510 - Ramit Sethi: Live Your Rich Life

#10 Justine Gallice : la vérité sur sa maladie cœliaque, son corps et ce qu’on ne voit pas sur les réseaux