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Work From The Inside Out


May 13, 2020

Bill Flynn is not your ordinary author, speaker, coach, and student. As a kid, Bill Flynn wanted to be a professional ice hockey player.  He played in college during his freshman year and some of his teammates even went on to the NHL, but at the end of the year, Bill felt that his love for the game had dwindled. He traded his time on the ice for a job at a pizza restaurant where he worked for several years, gaining increased responsibilities and developing a great work ethic.  It was fun, but not his life’s work.

Upon graduation, Bill landed a sales role at a computer products company and then, as he puts it, he got lucky.  He went to work for a company called Dragon Systems which developed voice-activated software.  Bill said it was the most rewarding job he ever had as a salesperson because they actually changed the lives of their customers, people with disabilities. 

After his time at Dragon, Bill got into the world of startups.  He worked for 10 different tech startups over the next 25 years serving in a variety of roles all the way up to CEO and President.  Today, he is an author, speaker, entrepreneur, coach, and student.  

In this week’s Work From The Inside Out podcast, Bill Flynn shares his career trajectory:

Listen, subscribe and read show notes at www.tammygoolerloeb.com/podcasts/ - episode 074