Have you ever wanted to start a business but didn’t know where or how to start?

Would you like to have a business that allows you to be successfully unemployed and never work for someone again?

Today I am excited to have a friend of mine, Tom Sylvester, on the show. He has been an owner of many successful businesses, and he is an ordinary person, just like us.

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Tom Sylvester, how are you successfully unemployed?

Tom has three different businesses that he owns:

  • Real estate investing: Started 12 or 13 years ago. It is set up with a team in place, so it doesn’t take much time.
  • Wine and liquor store: Started about 7 or 8 years ago. It is set up also with a team in place, so it doesn’t take much time.
  • Lifestyle Builders: Helping entrepreneurs build businesses very intentionally to support their ideal lifestyles.

Tom started all of these businesses with his wife, and they just released a book a month ago that builds that out as well.

He spends a lot of time with entrepreneurs helping them start and scale their businesses.

Tom and his wife found that once you are successfully unemployed, the world opens up for you and there are almost too many opportunities. They need to be picky about what they choose to work on.

Before this, weren’t you and your wife in the corporate world? Tell us a little bit about that.

Tom’s wife, Ariana, went to school for zoology, but she bounced around as a receptionist. She couldn’t find a job, but she had a lot of student loan debt to pay.

Tom met his wife the first day of college. She was the first women he met.

Tom went to school for computer science and he and his wife were on the traditional path of going to college and taking on student loan debt, with the hope of finding jobs to pay them off.

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As they went through college, Tom looked ahead and saw that they had about $80,000 in student loans and they had credit card debt. Neither of them had jobs coming out of school.

Tom didn’t like the math and the fact that they would need to work for the next 45 years, so he set a goal to retire by age 35.

When Tom set the goal, Ariana was not on board, because she wanted a traditional path of buying a house and having kids. They did a lot of that, but Tom had the itch and didn’t want to settle.


Tell us about Lifestyle Builders and how we can build our lives.

It doesn’t matter what you call it, everybody is seeking financial freedom. It is less about the money and more about having options and doing what you want, when you want, with whoever you want.

The biggest thing Tom saw was being clear on what that lifestyle looked like. Being a software engineer, he decided to work backwards to figure out how to engineer that.

Rather than being on that traditional path where you are always reacting and never doing what you want, instead say:

What do I want my life to look like in the future?

What can I immediately start doing that lets me live some of that life now while still being able to build more income and pay down debt to move toward that lifestyle.

Look at the end goal of where you want to be.


Give me a couple of questions that I need to think through so I can live the lifestyle I want. What is the first question everybody should start with?

Tom: Put yourself into the future. Five years from now you are sitting down. Look around and describe what you want your life to look like.

Dustin (pre-