From Swim Lessons to Bankruptcy Law: The Entrepreneurial Journey of Tony Sottile
Episode Details

Tony grew up in a regular all-American household and lived a pretty average childhood, but he never could’ve anticipated the life he now lives. He started his entrepreneurial journey as a child offering swim lessons in his area. Today, he runs a huge bankruptcy law firm with 4 branches across the US. Being an entrepreneur was never in the books. In fact, his father worked for GE for 45 years.

“The only thing I knew growing up was my dad who went to work for 45 years at General Electric. And most of those 45 years were not good. I remember surviving layoffs and surviving friends getting laid off - that's what I knew.”

While his story might seem like an average American tale, Tony reveals a significant personal adversity that he overcame in 2022. This episode is packed with entrepreneurial insights, advice on selecting a business partner, and tips for growing a small business.

Tony runs Sottile & Barile with his business partner Franco Barile. They are champions of small and mid-sized investors.

Adversities Tony Sottile had to overcome:

  • Unfulfilment at a day job 
  • Building a law firm from the ground up
  • Navigating challenges as a small business owner
  • Personal adversity that came to a head in 2022

Abundance Tony Sottile created:

  • Successful and growing law firm since 2015, with 4 branches now 
  • Expertise in bankruptcy and foreclosure work
  • Strong professional relationships and partnerships

Lessons from Tony Sottile’s adversities

  • Prepare in advance for adversity (mentally and financially) 

Tune in as Tony Sottile and Jamie talk about:

(00:00) Being a bankruptcy attorney

(05:32) How swimming made him an entrepreneur

(08:38) Why he had an entrepreneurial drive

(11:27) His first job (in a bad economy)

(12:52) Becoming an unexpected expert

(16:28) Feeling lost and unappreciated at work

(18:28) Peace of 9-5 vs. risk of a business (being scared)

(21:48) Forming a business partnership (how it happened)

(23:01) Choosing the perfect business partner

(25:01) Organic growth of his business

(28:52) Which is harder: job or business?

(29:56) Should you quit your job?

(33:30) The hardest thing he ever went through

(38:10) Fireside questions (philanthropy, grandfather, being genuine)

(41:23) Regulatory challenges = job security?

(43:00) What no one agrees with him about

(50:01) What money actually buys

(52:02) Giving money away

(54:17) Work with Tony Sottile

Charities Tony mentioned

Down Syndrome Association of Greater Cincinnati

Ohio Valley Voices

Connect with Tony Sottile: 



Haven Financial:


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Episode cover art for From Swim Lessons to Bankruptcy Law: The Entrepreneurial Journey of Tony Sottile