Learn the Ropes of Estate Sailing

No place is better suited to those with a taste for champagne but a beer budget than the humble estate sale. Its various guises—be they church rummage sales, yard sales, or online auctions—offer a variety of ways to acquire quality pieces and a little bit of history, with the bonus of saving grandma’s treasures from the landfill. For several years, vintage enthusiast Kate Davis has been writing a popular weekly newsletter, Midwestern Estate Sailing, that not only spotlights upcoming sales of note but offers a guide for the uninitiated. Her new book, Bring Cash, distills those lessons (the first one is in the title) along with essays about favorite finds and what to look for: dovetail joints in furniture, finished seams in clothing, the sign-in sheet at the front of the line so you’re not the last one admitted into the designer’s midcentury bungalow. Davis joins the podcast this week to talk about what she’s learned from estate sailing, her term for the ritual of trekking out to someone’s house and wandering its halls for treasure—which is almost always sure to include at least one inexplicable maritime tchotchke. Go beyond the episode: Kate Davis’s Bring Cash: A Guide to Estate Sales in the Midwest and Beyond Her newsletter, Midwestern Estate Sailing For more on the afterlives of secondhand stuff, listen to our interviews with Adam Minter (on global thrifting ) and Dana Thomas (on fast fashion ) Tune in every (other) week to catch interviews with the liveliest voices from literature, the arts, sciences, history, and public affairs; reports on cutting-edge works in progress; long-form narratives; and compelling excerpts from new books. Hosted by Stephanie Bastek and sponsored by the Phi Beta Kappa Society.

You can listen to Learn the Ropes of Estate Sailing online on Radio and Podcast. Open the player on this page to stream the available audio.

Learn the Ropes of Estate Sailing is an episode from Smarty Pants by Stephanie Bastek.

This episode is 24:25 long.

This episode was published on May 1, 2026.

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