044: How Dead End Roads Can Lead To Success (Chris Cerrone)

Chris Cerrone

There’s a statistic floating around that most of us will work in at least 6 different careers in our lives. Whether or not that’s true, we all know one simple fact: very few, if any, of us will work for one company for 40 or 50 years. Even business owners today most likely won’t own just one business, they will branch out into many.

A perfect example of this is our guest today, Chris Cerrone. Chris has owned several businesses in a few industries and has worked in the corporate world. All of which has led him to where he is today: a top-rated, successful podcaster producing The Chris Cerrone Show. Join us as we talk about all of this and more on the 44th edition of How’d You Get Into That?.


Chris is that rare breed who was born, raised and continues to live in the city of sin, Las Vegas. But far removed from the chaos and debauchery of the Vegas Strip, Chris and his wife live a fairly typical life of work and raising their two boys. Today Chris is the producer and co-host of his podcast, but his early career path was quite different.

Even as a child, Chris knew he wanted to be self-employed or do something in the business world. At the time, his dad owned the largest sporting goods store in Vegas and most of the Cerrone clan worked in the store. Chris has fond memories of his aunts, uncles and cousins all happily working together, laughing and enjoying their time together. He knew he wanted that when he grew up.

That early influence of entrepreneurship and business ownership rubbed off. Once he completed high school, Chris wasn’t sure what to do but his dad told him he had to find something or he was out of the house! That turned out to be a great motivator for Chris, as it would be for most of us, and he opted for real estate. He reasoned it was a better investment than college with a much faster, more lucrative return. So a few months later he had his license and he was on his way.


  • Who does he most want to be an example for?
  • The RE market was an easy cash cow when Chris got into it: true or false?
  • Would he ever go back into real estate?
  • What TV show did he want to create in his coffee house?
  • Does he miss his cafe?
  • Why he declined an extremely high-paying job offer in Brooklyn.
  • And so much more!

The market turned out to be quite difficult at the time and Chris worked incredibly hard to make a go of it. But he did and to this day he is grateful he did. That effort made all his wins that much sweeter and taught him the value of hustle, something he has continued to rely on in every day.

He spent the next 7 years in RE, but found himself burnt out and ready to move on to something else. He had done quite well in his real estate career so he was able to provide for his family while he explored his next options.

Within a year, he had bought a cafe and was again a business owner. His vision for the coffee shop was to have a Cheers-like atmosphere, the kind of place where everyone knows each other and chats regularly. And soon he had that, and he loved it.

But he was also market-savvy and could see the writing on the proverbial wall: the market was in decline and he and his wife would have to either sell the business, or be prepared to weather some major storms in the coming years.

They opted to sell, even though in his heart Chris still loved the cafe. His next major career was into the corporate world. A seeming 90 degree turn from his past ventures, Chris was introduced to the company by a friend of his. Chris really liked it and says those 5 years were some of the best of his life. But as he had come to experience, all good things often do come to an end and his company was bought out. He was one of the 1,000 people who were let go.

That was in the summer of 2013 and shortly after, he had the inspiration to start his own podcast. He had the financial runway to invest his time and energy into the show and that’s exactly what he did. With his typical tenacious attitude and entrepreneurial spirit, Chris dove head first into the podcast pool and has come up a winner.

The Chris Cerrone Show is one of the top-ranked podcasts on iTunes and he enjoys every minute of it. He and his co-host talk with some of the most interesting and innovative thinkers on their show, and they also offer VIP business coaching.

Chris is grateful for the paths that have led him to where he is today and the lessons he has learned along the way. It’s been a terrific experience having him on the show. Please join me in thanking him for giving of his time and insights on today’s episode. And thank you for being here with us! We’ll see you next time.

Tweetable: “Each dead end road I went down was a major learning experience.” Chris Cerrone


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