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Episode · Oct 7, 2026 · 57 min

The Country Singer Nashville Wouldn't Sign

with Jessie James Decker

Jessie James Decker is a singer and entrepreneur behind Kittenish and the JJD Fit Club.

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“There is no secret to it.”
Jessie James Decker

Summary

Jessie describes moving often as a military kid, being bullied at school and knowing early that she wanted to sing. She performed Patsy Montana's "I Want to Be a Cowboy's Sweetheart" at a talent show in Baker, Louisiana, then moved to Nashville with her mom and stepdad after high school. A record deal followed within two months, along with a gold record and a tour opening for the Jonas Brothers.

She and Ken revisit the low point when Jessie's record deal was falling apart after she struggled to make another pop record and a Nashville label could not make her country record work. Lonely in Nashville, with her family in Hawaii and her best friend moved out, she had no plan until a friend sent her a BlackBerry photo of Eric Decker. His long text led to their first call outside Mellow Mushroom. Later, Jessie talks about raising four children, the JJD Fit Club reaching 40,000 women, and sharing Kittenish with a partner as the brand reached major retailers. She also describes cooking dinner every day and making a family recipe book with her mom and sister.

Show notes

Jessie James Decker was born on a military base in Italy and lived in 14 places before she finished high school. At a sleepover in Newnan, Georgia, two senior girls she had never met pulled up with a bucket of slop they had been saving for weeks and dumped it over her head. Somebody made a page online called I Hate Jessica James.

At nine she got on a stage in Baker, Louisiana in a denim vest and red high tops, yodeled a Patsy Montana song and beat every adult in the room. Right out of high school her mom and stepdad loaded a U-Haul and dropped her in Nashville to live with a song plugger. She had a record deal two months later. A gold single, a top 25 debut, opening for the Jonas Brothers.

Then she tried to make a country record and nobody in Nashville would sign her. The deal fell apart. The boyfriend turned out to be a loser, her best friend moved out and her family was in Hawaii. No deal, no plan, swearing off men. Then a friend sent her a BlackBerry photo of a Broncos rookie in a white t-shirt with his arms folded.

This week I sat down with my friend Jessie to get the whole story. The text from Eric Decker that read like a novel. The phone call on a curb outside a Mellow Mushroom. Four kids and four comebacks, five foot one with nine-pound babies, and the 40,000 women now training with her in the JJD Fit Club. The Kittenish store in Nashville she has run since 2019, just picked up by Macy's, Nordstrom and Dillard's. And The Secret Sauce, her fourth book, written with her mom and her sister, out this week.

She never took the SATs, didn't have a drink on her 21st birthday, and cooks dinner every single night. I still don't know how she does all of it. Hope you guys enjoy this one.

Follow Jessie: @jessiejamesdecker

Her new book: The Secret Sauce, out now.

Read the transcript

Transcript

Made from YouTube's automatic captions and lightly corrected, so a few words and names may be off. Click a time to play the video from there.

Ken Rideout

All right, today's special guest. I very rarely if ever have used the term girl boss, but if ever there was a boss of female bosses, it's going to be Jessie James Decker. She is country singer, [snorts] influencer, New York Times best-selling author. She has her own fitness app that has like 12 bazillion followers. She does everything. And she's married to my dear friend, the great Eric Decker. Just James Decker. Welcome to the show.

Jessie James Decker

Thank you. Thank you. This is long overdue.

Ken Rideout

Hell yeah.

Jessie James Decker

This is long overdue.

Ken Rideout

Congratulations on your new book.

Jessie James Decker

Thank you. I'm really excited about it. Gosh, we are just days away from it officially coming out, but we've been we've been putting a lot of heart and soul into this one. This is my fourth one, but this one's with my mom and my sister, so this one's extra special.

Ken Rideout

How's mom's like in the uh spotlight?

Jessie James Decker

You know, my mom was built for the spotlight, so it's great. Honestly, it's um she does get a little nervous, but she's she's excited. I was on the phone with her on the way over here actually to sit with you and we're I was running through wardrobe and making sure she was okay and making sure she was set and she's like, I I just don't have the right clothes. I don't do this. I don't know what I'm supposed to wear. I'm like, we're going to take care of you.

We're going to make sure you look good. But we're excited.

Key takeaways

  • Gratitude can help keep success in perspective while you keep moving toward the next goal.
  • Consistency matters more than waiting for the perfect mood to exercise.
  • A hard workout can be worth doing even when starting feels difficult.
  • Know which parts of a business rely on your strengths and where a partner can help.
  • Cooking at home gives you more control over what goes into a meal.

Nowhere to Hide

A weekly letter from Ken Rideout about doing the uncomfortable part, and the reasons we use to avoid it.

It starts with 3 Days, 3 Hard Things: one short story from Ken and one hard thing to do, every day for three days. Then one letter a week.