Episode
You Just Lowered the Value of Your Business
- Podcast
- 21 Hats Podcast
- Published
- Sep 15, 2026
- Duration seconds
- 2924
- Processing state
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- https://21hats.com/you-just-lowered-the-value-of-your-business/
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Summary
Earlier this year, Ted Wolf suggested that Paul Downs should take a serious look at how artificial intelligence might improve his custom woodworking business. Paul was skeptical—but he invited Ted and his team to come visit the shop and see for themselves. This week, Ted reports back. He came away impressed by the business Paul has built but also convinced that Paul has a problem: As Ted sees it, too much of what makes the company work still resides in Paul’s head. Ted believes AI could help capture some of that knowledge, improve everything from estimating to production, and, perhaps most important, prepare the company to run one day without Paul. Paul remains unconvinced. He agrees that AI will find its way into the business eventually, but he questions whether it can capture the judgment, experience, and nuance required to build one-of-a-kind products. His inclination is to let the next owners figure that out. “So Paul,” Ted responds, “if they’re going to have to deal with it, you just lowered the value of your company.” Which raises a question that goes well beyond AI: If you hope someday to sell or transfer your business, how much of what you know has to be captured before you leave? Plus: In our latest Beyond Small segment, sponsored by Grasshopper Bank , I ask Paul, Ted, and Lena McGuire what would happen if their businesses suddenly doubled. Would they be thrilled—or terrified? Could they handle the growth? And would they even want it? That leads to a discussion that comes up here fairly often: How big do you really want your business to be?