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Aaron Volpatti at The Insider's Guide to Finance
Shawn Freeman, Digital Transformation Coach, provides insights into leadership, technology and the importance of personal connection.

Shawn Freeman is not your average entrepreneur; he is a man with a heartfelt mission to improve lives through technology, community engagement and mentorship. His distinctive background in tech, coupled with a genuine passion for service, has paved the way for a unique career marked by innovation, leadership and advocacy.

“I have always had the experience of if I help other people, it comes back to me so much bigger.” — Shawn Freeman [0:21:15]

Our discussion explores the story of Shawn’s transition from a tech background to venturing into an entirely different industry, leading to the eventual sale of his business, TWT Group in 2020. Along the way, we delve into the top three skills essential for any entrepreneur, the value of hiring the right people, and his current role as a Digital Transformation Coach. 

“I often joke that we’re like technology psychologists. You come to us, tell us about your problems, and then we help you navigate to the solution” - Shawn Freeman [0:35:35]

What sets this episode apart is Shawn’s emphasis on the importance of making meaningful, personal connections, and how value alignment in today’s business landscape makes for effective leadership. Gain insights into effective selling strategies, why every business should take digital transformation seriously, and the impact of AI on operations. 

“Technology influences every part of every business now.” — Shawn Freeman [0:36:39]

This episode offers valuable insights into investor relations and marketing strategies you don’t want to miss. Tune in now!


  • Background about Shawn, starting his own business, and his professional journey. 

  • He shares why he chose to sell his business and details about the sale.

  • What he would have done differently and what he learned. 

  • Outline of the essential financial aspects and metrics he monitored.

  • How he learned the value of cash flow and what it means for a business.

  • His current role as a digital transformation coach and passion for helping people.

  • Shawn unpacks how technology is going to change the business landscape.

  • Discover tips to build and foster genuine relationships in sales.

  • His approach to marketing his brand and the power of referrals.

  • Valuable insights into being an effective leader during tough times.

  • Leveraging technology to enhance employee and customer experiences.

  • Learn about his mentoring work, grants, and other ways he is giving back.

  • Leadership lessons, finding the right people, and common mistakes people make.

  • Threats and blind spots that small businesses and startups need to know about.


For more information on our sponsor, please visit Olympia Trust Company

Please note that the information contained in this interview is not financial advice but for entertainment purposes. I am not a financial advisor and make no warranties or representations concerning the accuracy or suitability of the information contained in this interview. I recommend that any and all investment decisions be made with the advice of registered investment advisors.


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