The following is a bonus replay of one of 2022's popular episodes.

When Herald Chen was growing up in a town not far from Pittsburg, he dreamed of someday running the small town’s steel mill. Years later when he was graduating from the University of Pennsylvania, the steel mill no longer occupied Chen’s maturing career aspirations.

“My two job offers were to either go make soap for Procter & Gamble at a manufacturing plant in Baltimore or go to Wall Street,“ remembers Chen, who adds that the offers for the seemingly different jobs came as a result of having graduated from UPenn’s Management and Technology program—a curriculum that offered a dual degree in engineering and finance.

Chen chose Wall Street and in 1995 landed at KKR, the private equity firm that had feasted on leveraged buyouts in 1970s and 1980s.

Recalls Chen: “I had a front row seat for meeting many CEOs and CFOs and invested behind a couple dozen of them, so I learned a lot about what the good, the bad, and the ugly look like in these companies.”

Twenty-seven years later, KKR can arguably be seen to have been the mother ship of Chen’s finance career, a place that over time he would leave and then return to as the investment house provided him with the wherewithal to open new professional chapters—the longest being from 2007 to 2019, when he headed KKR’s Technology, Media, and Telecom practice.

Along the way, Chen demonstrated a rapport with C-suite members and company boards that distinguished him from other investors, a trait that led to a growing number of invitations to sit on different company boards.

“I had figured out that I wanted to be building businesses, but I also knew that I wasn’t the smartest or brightest or most charismatic person in the room, so maybe the best way for me wasn’t actually sitting in the CEO seat but instead was investing and sitting on boards and helping CEOs,” comments Chen, who has held a number of board seats, as well as served as board chair for such companies as Internet Brands/WebMD, Optiv, Epicor, BMC Software, and Mitchell International.

With a boardroom track record that few of his CFO peers can match, Chen attributes his success in part to being a good listener. “I would invest behind CEOs and CFOs whom others just didn’t understand—they just didn’t comprehend what these people were trying to do—because I would find that I could create a lot of value with them just by taking a little extra time to hear them through,” remarks Chen.

When asked to offer advice for CFOs seeking to lower the temperature of certain boardroom discussions, Chen shares a story involving notable KKR financier Henry Kravis: “When I was at KKR, I made a mistake in some of the numbers one time. It was late in the transaction, at the point where on Wall Street you’d expect to get yelled at and there would be this big blowup—but I remember Henry Kravis just getting very calm and saying, ‘Hey, we’ll get through this and come out the other side.’” –Jack Sweeney

Eps 2: Making Agreements