The Rules of Entrepreneurship with Sean Castrina

For this episode, I am excited to welcome Sean Castrina. Sean is a serial entrepreneur, having started more than 20 companies over the last 20 years, and still seeks to launch a new venture annually. He is an amazing investor, teacher, and highly-sought-after speaker who communicates with humor and a bluntness that engages and captures his audience. His podcast The 10 Minute Entrepreneur, is one of iTunes’ most popular business shows. Sean is also the author of 8 Unbreakable Rules for Business Startup Success, The Greatest Entrepreneur in the World, and World’s Greatest Business Plan.

We start this episode with Sean’s background story. After graduating from college, he was able to secure his dream job. But five years later, he got fired overnight with no warning, after just having a newborn child. This was the moment he realized that he would never again work for anybody but himself. He went on to create a car detailing company that brought in $35,000 of passive income. He repeated that formula with service companies over the next 25 years.

Sean started a lot of businesses in his lifetime and along the way he learned that you don’t have to love that business, you don’t even have to be a part of it, in order to make a profit. As an entrepreneur, his goal is to systematize them and make them passive at some level. Sean goes on to talk about how the fact that he was born legally blind affected his childhood and his adult life. He explains how it taught him to work with that, around that, and defeat any obstacle that came his way.

We then move on to learn more about Sean’s entrepreneurial career. He talks about how, after creating his detailing business, he started working with other service companies. At one point, he wanted to turn his dining room into an office, but he soon realized that it was impossible to find a handyman in his community. Led by his entrepreneurial spirit, he started a company named Advantage Handyman Service that ended up being a multimillion-dollar company within the first three years, and soon it will be an 8-figure company. It was always the same formula that turned out to be successful for him - service companies.

We then move on to talking about Sean’s plans for the future. His goal is to start a new company every single year. He explains how some business owners have an entrepreneurial moment - they start a business and they are happy with that, but that is where it stops. Some entrepreneurs are addicted to looking for the next thing that they can get involved in, an opportunity that is within what they know and understand.

Sean and I then dive into discussing one of his books called 8 Unbreakable Rules for Business Startup Success. He shares his perspective about the book and walks us through all eight rules that helped him become a successful business owner. Among other things, he explains why you need a great team, why you need to know your numbers, and how important marketing is.

Lastly, Sean shares his amazing advice on how to learn from other successful entrepreneurs. Business owners love to get a pat on the back and they love to tell you what they are doing. His advice is to go to any business owner, tell them you love their business and you would just love to bring them a cup of coffee once a month and pick their brain for twenty minutes. You will get a wealth of wisdom from doing this simple task!

Don’t miss this episode of Just Start Real Estate that is filled with practical and incredibly actionable advice from an amazing, and most definitely serial, entrepreneur, Sean Castrina!

Notable Quotes:

“A job is not security. At the very least, you have to put up with stuff that you don't even like.”

Sean Castrina

“There are very few jobs that are like being an entrepreneur.”

Sean Castrina

“Business is nothing but chess pieces; every chess piece moves a little bit differently. Employment is playing checkers; you move linear, trying to get to the end of the board.”