Get Real with Caroline Hobby · Nashville Podcast Network

Getting Real with Well Dressed: Where Celebrity Closets Become Your Wardrobe

December 1, 2025·1 hr 23 min·5 clips

Bonnie says Instagram shut down her account in October 2022 after a resale ad triggered the platform.

The conversation opens by getting into the business behind their operation. They talk through how the business makes money, including commissions, rent, insurance, and the other overhead that comes with running a small operation with contractors and one worker who is technically a contract worker. The numbers matter here. The guest says commissions are the biggest expense, and the conversation lingers on how a 25 to 30 percent net profit margin feels healthy once you understand what is going out the door. From there, the host asks how they met. The answer starts before the quit, because they already knew each other when one of them moved to Nashville and sent an email to her entire Gmail contact list. That old-school blast reaches back surprisingly far. She jokes that even a real estate broker from 2003 in New York City got the message. The guest then talks about her long stretch in New York. She lived there for 20 years, says it was a different life, and admits she had a really good time there even though she is glad not to be there right now. The host follows the thread into the guest's husband and his career in investing. The explanation lands in the world of private equity and hedge funds, with a quick clarification that PE is usually about longer-term investments in more established companies that need cleaning up and have room to grow. Then the host pivots to celebrity journalism. The guest says she wrote for the New York Post, Us Weekly, and People magazine. The host reacts to the celebrity side of that life and keeps pressing for stories. The host asks about favorite interviews, and Hugh Jackman comes up. The whole exchange keeps its quick, conversational rhythm. There are little checks, clarifications, and back-and-forths that make the talk feel immediate rather than packaged. The episode's larger shape is a story about how media, money, and reinvention overlap. It leaves the sense that a business built around celebrity closets still runs on ordinary hustle and plainspoken trust.

As heard by us

A grounded conversation about the work behind a polished public life, with business details giving the personal story real weight.

Bailey Taylor keeps the conversation close to the work itself, and that gives the episode its shape. The talk starts with the unglamorous side of the business, commissions, rent, insurance, overhead, and a 25 to 30 percent net profit margin, before it moves into the person…

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Why you'd press play

Celebrity journalism, private-equity margins, and a very human pivot.

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