The Owner's Box @WashU Olin

One week before his passing, Giorgio Armani sat down with the Financial Times to talk about control, something he knew a thing or two about. In this episode, I unpack how Armani designed one of the most fascinating succession plans I’ve ever seen. Balancing legacy, leadership, and the hard question of when control becomes… too much control. Special Guest: Stuart Weitzman.

Today's guest, Dilawar Syed, is a perfect person to kick off this season. I met Dilawar last year while working with the Brookings Institution, focusing on the issue of aging business owners. At the time, Dilawar was Deputy Administrator of the Small Business Administration. His background is extensive, including his role as President of Freshworks, a company that serves small businesses. This spring, we collaborated on a piece for The Conversation and Fast Company about how tariff uncertainty can paralyze small business operators. As you can imagine, Dilawar has a lot of insight to share on this and other topics here on The Owner's Box.

In today’s episode, I talk to a craftsman who has explored the tradeoffs inherent in an over attentiveness to scale when developing a business – David Stine of David Stine Furniture. At the core, David is a craftsman, and this attention to the craft shapes everything from his approach to debt and growth, how he thinks about creativity, and even the rich life, broadly defined. Whether you run a small business, dream of starting one, or just want a fresh lens on work and meaning—this episode is for you.

What does it take to be an entrepreneur? What is the skill set that separates the entrepreneur from the rest of us? Might there even be a personality or gene that helps people be especially gifted here?In today’s episode we get to listen in to a short snippet of a recent conversation I had with John McDonnell, the leader and owner behind McDonnell Douglas which eventually sold to Boeing about what he says at the start of the company, and what it might imply for the rest of us. Special Guest: John McDonnell.

In today’s episode, Peter Boumgarden sits down with Anna-Lisa Miller, Executive Director of Ownership Works. Her organization is built on a bold premise: that employee ownership—typically seen as separate from private equity—might actually enhance the impact of a private equity deal. It’s a rare intersection of two ownership models, and Anna-Lisa provides a peak beneath the hood of this design. Listen in as we explore how these approaches can work together—and what that could mean for the future of finance-led ownership transitions in the middle market. Special Guest: Anna-Lisa Miller.