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

Welcome to the Learning Leader Show. I am your host, Ryan Hawk. Thank you so much for being here. Go to learningleaders.com For show notes of this and all podcast episodes, go to learningleader.com. Now on to tonight's featured leader, Brian Kelly, also known as the points guy. Brian started hacking computers in the nineties, grew up relentlessly resourceful, and even as a kid had Mercedes cutouts on his wall because he envisioned building a wealthy and abundant life. And then he went out and actually did it. After a stint at Morgan Stanley, he built The Point Sky into a business generating over $1,000,000 a month and eventually sold it to Bankrate for $28,000,000. Today, he still leads The Points Guy, travels the world, and invests in and advises fast growing startups. During our conversation, Brian shares the mindset that fueled his rise. We talk about the lessons he learned from scaling a media empire, mistakes he's made as the CEO of a fast growing company, and the must have attributes he looks for when hiring a leader. He also opens up about about wealth, imposter syndrome, the joy of family, and at the end, he shares some very useful life slash career advice. Ladies and gentlemen, please enjoy my conversation with Brian Kelly. This episode is brought to you by Insight Global. Insight Global is a staffing and professional services company that builds world class technical teams for clients around the globe. If you need help with your applications, infrastructure, or data layer, Insight Global's team of technical experts can build custom or manage services to deliver the outcomes you desire. Getting the most out of your technology can be tough, but growing your business with the right technical solutions can be magic. Visit insightglobal.com/learningleader. That's insightglobal.com/learningleader today to learn more. I read that you were a computer nerd growing up, and you got one of your first jobs. You were hired by your dad to be his travel agent. What happened here? Can you take me back to that time when you're around 12 years old and got hired by your dad? Well, I was just a hacker in the nineties. You know, I'm 42 years old today, born in 1983. So if you imagine like, 1991, got my first computer, taught myself MS DOS. And I think in '92 or '3, we got Prodigy Internet. And at age, you know, eight or nine, I was the computer, like, system administrator for my family, which is kinda crazy to think about. And yeah. So I was always on AOL, Prodigy. You know, some of my first jobs were in the classified ads on AOL. When eBay first launched in the nineties, you couldn't actually upload any items. So there were thrift shop owners posting for people like me. I was a kid at the time on summer break. I would post their items on eBay in the middle of the night when the server capacity was down. …