Newsletter

Sleeping Giant Capital | October Newsletter

Written by Sleeping Giant Capital | 10/1/2025

From the Desk of Doug and Derrick

Welcome to the inaugural edition of Awaken, your source for updates from Sleeping Giant Capital.

Six years ago, we had this crazy vision of finding and training aspiring owner operators, convincing them to leave their jobs, raising an investment fund, buying West Michigan businesses, and then connecting these businesses to an undergraduate program to help them grow.

All in service of creating what our mentor Dick Haworth would call “The Big Win.” Where investment returns met social returns and educational returns. This vision has become a reality and this fall has been a season of great momentum.

Highlights that you’ll read more about:

  • Historic launch of our second fund; Principled Impact Evergreen Fund II

  • Hiring Chelsea Dubey to lead our marketing and talent recruitment

  • Welcoming our newest CEO in Residence: Phil Bowman

  • Doug was interviewed on the popular ETA podcast, Acquiring Minds

Thank you for joining us on this journey,


 

Pioneering a Place-Based Investment Platform Celebration

"What we see from those gathered in this room, is evidence of a new model. A model that takes the engine of capitalism…the transformative power of education…and the entrepreneurial leap of faith…unites them together in mutual benefit and anchors them in a place.”
Doug Lepisto, Co-Founder, Sleeping Giant Capital


On September 23, we gathered with 230 of our partners, including Governor Whitmer, investors, CEOs, portfolio company employees, students and Western Michigan University leadership to celebrate the launch of our second fund. It was a landmark moment in our history and one that we will never forget. Read more →

CEO in Residence Spotlight: Phil Bowman

We are proud to announce Phil Bowman as our newest CEO in Residence (CIR). Phil brings nearly 25 years of leadership experience and a mission to acquire and grow a technical services company in West Michigan. With an engineering foundation and a proven track record across multiple industries, Phil has delivered profitable value for several national and global Fortune 500 companies, supporting businesses generating more than $500M in annual revenue. Read more →

 

 

 

 

The Do Diligence Podcast – Feature Episode 17

On Episode 17 of The Do Diligence podcast by Sleeping Giant Capital, host Derrick McIver welcomes Tom Deans, acclaimed author and global thought leader on family business succession.

Tom shares insights drawn from his own experience running and selling a multi-generational manufacturing company and from his three-book trilogy on family wealth and succession planning, including Every Family’s Business, Willing Wisdom, and The Happy Inheritor. He challenges conventional wisdom around gifting family businesses, advocating instead for transparent conversations, third-party valuations, and the critical importance of having next-generation owners risk their own capital.

Listen here, on Apple Podcast or on Spotify

Acquire Program Accepting Applications for February Session

Our Acquire Executive Education Coaching Program continues to grow, helping professionals take the first step toward becoming owner-operators. Over 8–10 weeks, participants gain practical tools, coaching and confidence to begin their search for a closely-held business to acquire. We’re proud to be supporting the next generation of leaders who want to preserve legacies and strengthen communities through local ownership. Applications are now open for our February cohort. Apply here!