668: Brian Kelly (The Points Guy) - Building a Media Empire, Crafting a Big Vision, Relentless Leaders, Hiring Well, Scaling Up, & How To Win at Travel

Go to www.LearningLeader.com for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. 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 ...