337. Jessie James Decker on Building a $60M Business, Betting on Herself & Why It’s Never “No”
Oct 5, 2026 · 54m
Summary
Jesse James Decker discusses her transition from country pop star to multi-hyphenate entrepreneur, covering her fashion brand Kitish, new cookbook, and fitness app. She shares insights on overcoming imposter syndrome by leveraging her unique voice, managing burnout through strategic partnerships, and maintaining a healthy financial dynamic with her husband, Eric Decker.
Topics discussed
Sponsor: American Express Business Platinum
Introduction: Jesse James Decker's multi-hyphenated career
The drive to keep building and the lack of a finish line
Childhood influences and the need to prove oneself
Advice to her 21-year-old self on career and persistence
Financial lessons from Rod Stewart and trusting expertise
Mother's scrappy attitude and gratitude during hard times
Breaking the 'one niche' box and embracing creativity
Overcoming imposter syndrome in new industries
Identifying her true mastery: singing and vocal performance
The 'trunk of the tree' concept and personal brand
Launch and success of her fitness app community
Sponsor: Whatnot live shopping platform
Building the fitness app without focusing on numbers
Scaling Kitish: bringing on a wholesale partner
Dancing with the Stars: lessons on freedom and performance
Balancing DWTS, touring, and motherhood
Managing love and money in a high-profile marriage
Sponsor: Superhuman AI productivity tools
Dividing financial responsibilities with Eric Decker
Respecting work boundaries and maintaining privacy
New book 'The Secret Sauce' and family traditions
The future of the music industry and artist longevity
Social media strategy and authentic content creation
Final trading secret: It is never no
Sponsor: Checkout.com
Listen ad-free on Castria