The Owner's Box @WashU Olin

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.

For some people, a gig is a short-term step to something different, something bigger, an unspoken plan still not yet disclosed in the space unknowing between the front and back seat. To gain some insight into this space, I want to introduce you to Margarita Tsoutsoura, my colleague in the finance department of Olin Business School. Margarita’s research reminds us that the path toward starting something isn’t always getting a degree in entrepreneurship or spinning something out of an established company. Sometimes, the path is about being young, flexible, and willing to tinker within a flexible career path—the gig economy—that didn’t exist in the same way 20 years earlier.