
Mark Cleveland interviews Douglas Song about the importance of stewardship in business and the lessons learned from his entrepreneurial journey.
What happens when an entrepreneur spends decades helping founders transition, scale, and protect the businesses they've built? In this episode of The Parallel Entrepreneur , Mark Cleveland sits down with Douglas Song , founder and CEO of Protos Capital, for a wide-ranging conversation on independent sponsors, lower middle market acquisitions, leadership, succession planning, AI, uncertainty, and what founders often overlook when preparing for growth or exit. Doug shares lessons from dozens of transactions across multiple industries, including how he evaluates leadership teams, why organic growth still matters more than acquisition rollups, and what makes a business resilient in a world filled with constant disruption. But this conversation also becomes deeply personal. Doug reflects on immigrating to the United States from South Korea as a child, watching his parents build a life through entrepreneurship, and how that experience shaped the way he thinks about people, stewardship, and long-term value creation. The conversation also explores: The rise of the independent sponsor model Why succession planning is becoming urgent for founder-led businesses AI adoption in lower middle…
Explore listener stats, chart rankings, contacts and more on the Parallel Entrepreneur with Mark Cleveland podcast page.