From $7 an Hour to the Today Show: Kimmay Caldwell on Building a Business Around Body Confidence

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At 18, Kimmay Caldwell moved to New York City, put herself through school for musical theater, and sold shoes for $7 an hour. When a friend mentioned a bra shop that was hiring, Kimmay’s first question was, “What do they pay?” The answer was $10 an hour, and she was hired on the spot. That job changed her life.

In this episode of Off the Books, Jonny and Nikita sit down with Kimmay, the undergarment educator behind Hurray Kimmay and the founder of Hurray Media. Twenty-one years after that first fitting room, she has appeared on the Today Show and the Rachael Ray Show ten times each, been on the Drew Barrymore Show, Good Morning America, and more, and built a business that spans free education for bra wearers, training for bra fitters around the world, and content partnerships with bra and swimwear brands. She did it all without pitching herself to a single TV show.

But this isn’t just a highlight reel. Kimmay opens up about a hard personal year when she almost quit her business entirely, and what it took to turn it around. She calls what she’d been doing before “outsourcing her anxiety,” and explains why simplifying everything made her business stronger. She also shares the five criteria every project now has to meet, and why “profitable” finally made the list.

IN THIS EPISODE, WE TALK ABOUT:

• Going from $7 an hour selling shoes to a bra shop job that changed everything
• What fitting real bodies taught her about the gap between magazines and reality
• Founding Hurray Media and the phone call that proved her business model
• How a creative entrepreneur monetizes a niche nobody had defined yet
• Building multiple revenue streams, from TV segments to UGC production
• Landing national TV appearances without ever pitching herself
• Her long-time philosophy: say yes and be nice
• Learning to say no as her priorities shift in her 40s
• The fitting room moment that captures her “why”
• Almost quitting her business
• Letting go of the “starving artist” mindset and getting serious about money
• The tools that keep her running solo, including Canva, Loom, Metricool, ManyChat, Google Workspace, and Collective
• Treating business as problem-solving, and learning to love the process

TIMESTAMPS:

00:00 Welcome to Off the Books
 00:40 Three things to know about Kimmay
 02:44 The movie trailer version: $7 an hour in New York City
 03:42 What the fitting room taught her about real bodies
 04:40 Founding Hurray Media
 05:34 The three audiences she serves
 08:01 How do you monetize something like this?
 13:14 What a typical day looks like
 16:13 How clients find her
 17:37 National TV, without ever pitching herself
 21:01 Say yes and be nice
 22:50 The fitting room story behind her “why”
 27:07 Almost quitting, and her five criteria for every project
 30:29 Letting go of the starving artist mindset
 33:05 “Outsourcing anxiety”
 34:02 Simplify before you scale
 38:37 “This is what a successful woman looks like”
 39:36 Business is problem-solving

FAVORITE MOMENTS:

On getting on TV: there’s no shortcut. Be really good at what you do for a long time, keep putting out your own content, and the opportunities will start coming to you.

On saying yes: say yes, show up, and do a great job, then be someone people want to work with again. Reputation goes both ways.

On delegating: before you hire someone, make sure you know how to do the task yourself. Simplify first, then delegate.

On running a business: it will bring up every fear you’ve ever had. Learn to love the person you’re building it with, which is you, and be kind to yourself when you mess up.

CONNECT WITH KIMMAY:

Kimmay loves hearing from listeners, so say hi and tell her you heard her on Off the Books.

Website: https://hurraykimmay.com
Instagram and YouTube: @hurraykimmay

ABOUT OFF THE BOOKS:

Off the Books is a podcast from Collective, hosted by Jonny and Nikita. Every week, we sit down with solopreneurs navigating the journey of running a business of one, to share the real stories behind how they built it, what they’ve learned along the way, and what they wish someone had told them sooner.

Collective is the all-in-one back office for businesses-of-one, with S Corp setup, payroll, bookkeeping, and tax filing in one place, so you can spend more time on the work you love. 

If you enjoyed this episode, subscribe, leave a review, and share it with a fellow solopreneur who needs to hear Kimmay’s story.

This episode is for informational and entertainment purposes only and isn’t tax, legal, or financial advice.

Learn more at https://www.collective.com