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.