Do Diligence

Episode 21: From Corporate to Co-CEOs Inside the Journey of Ben and Rick

In this episode of The Due Diligence Podcast, we sit down with Ben and Rick, the first co-CEOs at Sleeping Giant Capital, as they share their journey from corporate careers into leading two manufacturing businesses, Portland Products and Pro Stamp. With backgrounds in mechanical engineering and early entrepreneurial ventures, Ben and Rick walk through how they transitioned into acquisition entrepreneurship through the CEO-in-Residence program and what it actually looked like to move from diligence into day-to-day leadership. They reflect on the realities of stepping into ownership, from navigating the complexities of the acquisition process to adjusting expectations once inside the business. The conversation explores what life looks like as co-CEOs, balancing long-term strategy with the immediate demands of running manufacturing operations. They also share candid lessons from their experience, including the nuances of sales cycles in the industry, unexpected external pressures like tariffs, and the importance of building and trusting the right team.

Episode 20: Private Equity vs. The Local: Inside a Debate on Ownership & Community with Maryann Feldman and Martin Kenney

In Episode 20 of the Do Diligence Podcast, Doug Lepisto sits down with Maryann Feldman and Martin Kenney, authors of "Private Equity and the Demise of the Local." They delve into a critical examination of how private equity reshapes communities and the implications of ownership on local economies. Through their research, Maryann and Martin illuminate the troubling patterns of private equity investment, showcasing how it often leads to the offshoring of jobs, diminished local control, and the erosion of community ties. They advocate for alternative investment models that prioritize local ownership and community engagement. Join them as they explore the intersection of finance, community, and the future of local economies, emphasizing the importance of place-based investment strategies as a counter to traditional private equity practices.

Episode 19: Buyer vs. Seller: Inside a Small Business Deal with Kelly Conway and Rob Elliott

In Episode 19 of Do Diligence, I sit down with Kelly Conway and Rob Elliott to explore the intricate dynamics of a small business deal from both the buyer's and seller's perspectives. This episode marks a unique occasion as we bring together the insights of a buyer and seller simultaneously. Kelly, a seasoned executive, acquired Rob's company, Pondera, which specializes in leadership consulting. We delve into their experiences throughout the transaction, discussing the emotional and operational challenges they faced, the importance of communication, and the strategies they employed to foster trust. Both share valuable lessons learned during the process, including the critical role of aligning expectations and the necessity of involving key team members early on. Whether you're considering acquiring or selling a business, their insights will provide you with essential guidance for navigating these complex transactions.

Episode 18: From Searcher to CEO: Lessons from Justin Murray’s Journey with SGC and SignComp

What does it really take to leave a Fortune 500 job and become the owner-operator of a small business? In this episode of The Do Diligence Podcast, we sit down with Justin Murray — CEO of SignComp and Sleeping Giant Capital’s first CEO in Residence — for his unfiltered playbook on ETA: from personalizing outreach and reading seller motivations to handling deal curveballs, first-100-day leadership, and building a cadence for growth.

Episode 17: The Uncomfortable Truth of Family Business Transitions w/ Tom Deans

What really happens when a family business changes hands? In Episode 17 of The Do Diligence Podcast, I sit down with Tom Deans, author and global thought leader on family business succession, to hear his unfiltered take on succession planning — from tackling secrecy to redefining legacy.