Oct. 1, 2025

EP 126: The Late-Stage Entrepreneur: Gary Hentschel on Lessons on Risk, Value, and Second Acts

EP 126: The Late-Stage Entrepreneur: Gary Hentschel on Lessons on Risk, Value, and Second Acts

Most buyers slow down in their sixties. But not . He’s out buying companies, doubling their value, and selling them again. As a partner at and CEO at , Gary brings decades of experience as a banker, entrepreneur, and operator. In this...

Most buyers slow down in their sixties. But not Gary Hentschel. He’s out buying companies, doubling their value, and selling them again. 

As a partner at The September Group and CEO at WSI Technologies, Gary brings decades of experience as a banker, entrepreneur, and operator. In this episode, he shares how he appraises businesses, what sellers get wrong about their company’s value, and why good leadership matters when a business is up for sale.

In this episode, you will:

  • Discover what buyers look for in a management team

  • See how earnouts help keep deals on track

  • Find out why sellers often misprice their businesses

 

Highlights:

(00:00) Meet Gary Hentschel

(03:31) The importance of good partnerships

(06:22) Navigating business acquisitions

(09:47) Evaluating business potential

(17:07) Risk management and deal structuring

(21:30) The role of earnouts and management teams

(29:03) First 60 days post-acquisition

(31:18) Learning from buyers, sellers, and advisors

(35:17) Current market trends and insights

 

Resources:

For past guests, please visit https://www.defendersofbusinessvalue.com/

 

Follow Gary:

Connect on LinkedIn: https://www.linkedin.com/in/gary-hentschel-3793487/ 

E-Mail: gfhentschel@gmail.com 

 

Learn more about Gary’s companies:

The September Group: http://theseptembergroup.com/ 

WSI Technologies: https://wsi-tech.com/ 

 

Follow Ed:

Connect on LinkedIn: https://www.linkedin.com/in/edmysogland/

Instagram: https://www.instagram.com/defendersofbusinessvalue/

Facebook: https://www.facebook.com/bvdefenders