Sleeping Giant Capital | October Frontier Newsletter

<span id="hs_cos_wrapper_name" class="hs_cos_wrapper hs_cos_wrapper_meta_field hs_cos_wrapper_type_text" style="" data-hs-cos-general-type="meta_field" data-hs-cos-type="text" >Sleeping Giant Capital | October Frontier Newsletter</span>

by Sleeping Giant Capital on 10/1/2025

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

Six years ago, Derrick and I had a crazy vision. Find and train aspiring owner-operators. Convince them to leave their jobs. Raise an investment fund. Buy West Michigan businesses. And connect these businesses to an undergraduate business program to help them grow. All in service of creating a “The Big Win” - where investment returns met social returns and educational returns.

Today, that vision is a tangible reality. With six growing acquisitions employing more than 300 people, a full pipeline of aspiring owner-operators, and a flourishing undergraduate program, we are demonstrating that place-based investing can drive financial, social, and educational returns.

This fall marks another major milestone as we launched our second fund - with over $100 million in commitments - and continue to build a model that is earning national attention for what is possible when capital, education, and community are aligned.

Highlights that you’ll read more about:

Launch of our second fund; Principled Impact Evergreen Fund II with over $100 million in initial commitments
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,

Co-Founders, Sleeping Giant Capital

Pioneering a Place-Based Investment Platform Celebration

SGC Portland Event Image (30)

"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

PhilB-Web 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 →

What drew you to Sleeping Giant Capital’s model?

The SGC model is a great fit for my stage of life. Pursuing a small business acquisition on my own would require significantly more time, effort, and risk. SGC provides a solution with available resources, a vetted process, and committed capital. With a busy family to care for, I’m not sure I would be able to pull off a successful search while working full-time. Additionally, I personally knew a past CIR that partnered with SGC and successfully bought a business—this gave credence to the SGC model and piqued my interest.

Tell us about the kind of business that you want to lead

I’m seeking to acquire and lead a technical services company in West Michigan, with a focus on mission-critical sectors such as commercial equipment repair, building systems, and other specialized contractor services. I’m looking for a business with recurring revenue, high barriers to entry, and strong customer relationships that can serve as a platform for long-term growth and expansion. My goal is to be a hands-on owner-operator, building stability and scale while creating lasting value.

What has surprised you most about becoming a CIR?

The shift from a high-demand corporate leadership role to a full-time business acquisition has been significant, in a good way. It has been a refreshing change of pace, however I’m eager to make tangible progress. The early stages to launch the search are critical and require a structured approach to find the new rhythm of my day-to-day. Patience with diligence is a key quality you must have as a CIR.

What advice would you give to someone considering the owner-operator path?

If you have an entrepreneurial drive and ambition, and want to own and lead a company, know this: you can make it happen. It doesn’t have to live as an idea or concept, and it doesn’t have to be a startup business. ETA is real and obtainable, especially when partnering with Sleeping Giant Capital. There are some great podcasts that feature owners that have taken the leap and have lived to tell about it—it’s empowering and infectious to hear other’s success stories—consume them. I also highly recommend two books: HBR Guide to Buying a Small Business (Ruback, Yudkoff) and Buy Then Build (Deibel).

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.

Watch here, or listen on Apple Podcast or 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.

The Acquire course for fall is sold out. We’re now taking applications and building a waitlist for February. Consider sharing this opportunity with a friend or colleague who’s looking for a career or life change.

Apply here →

"Empowers ownership, preserves legacies, and strengthens communities. "