Tom Sylvester is a serial entrepreneur, podcast host, author, business coach, and a self-described “renaissance man”.

Tom worked 3 jobs to get himself through high school and into college. He met his wife, and business partner, Ariana, on his first day of College. They graduated from college with $60,000 in debt, and for Tom, the thought of working away in a cubicle for the next 45 years was not appealing. That’s when he decided to set a goal to “retire” by the age of 35. Ariana thought he was crazy.

Now truth is Tom didn’t want to stop working, he just wanted to have the freedom and independence to choose when to work, where to work, who to work with, and what to work on. The entrepreneur’s dream, right? Tom learned some hard lessons along the way but did achieve his goal before his 35 birthday.

Today Tom and Ariana operate a real estate investment firm, a wine and spirits store, and two coaching and mentoring businesses.


  • Got into the messy details about many of the lessons he learned along his entrepreneurial journey
  • Explains why he always encourages people to focus first on understanding the lifestyle they want to live
  • Points out that the low cost of entry for service based businesses takes away many of the early stage learning opportunities for new entrepreneurs
  • Explains the difference between an entrepreneur and a solopreneur
  • Shares some of the most common mistakes he sees new entrepreneurs make
  • Stresses the importance of surrounding yourself with the right people
  • Tells us that failure is not bad
  • Explains why he likes it when customers say no
  • And tells us about his soon to be released book titled Lifestyle Builders

This was a fun conversation packed with great advice.  Enjoy.

You can reach Tom at:


Please do not hesitate to reach out to me. I’d love to hear your thoughts, comments, and stories, or just make a connection.

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