#961. Jaclyn Johnson has built businesses, sold them, bought them back, started over, and learned that success doesn’t always look the way you think it will.

This week, Jaclyn joins Kaitlyn for a refreshingly honest conversation about the highs and lows behind building Create & Cultivate, what it actually felt like to sell the company she poured everything into, and why buying it back became one of the biggest full-circle moments of her career. She opens up about navigating burnout, a breast cancer diagnosis that shifted her perspective, moving back to New York, and the lessons she’s learned through every major pivot along the way.

Plus, Kaitlyn puts Jaclyn’s investor instincts to the test in a game of Invest or Pass, pitching everything from startup ideas to some of the biggest brands we all know as Jaclyn reveals what she’d invest in, what she’d pass on, and why.

Whether you’ve followed Jaclyn for years or this is your first introduction, this conversation goes far beyond business. It’s about reinvention, resilience, taking risks, and finding the courage to bet on yourself—no matter what chapter you’re in.

If you’re LOVING this podcast, please follow and leave a rating and review below! PLUS, FOLLOW OUR PODCAST INSTAGRAM HERE!

Thank you to our Sponsors! Check out these AMAZING deals!

Nutrafol: For a limited time, Nutrafol is offering our listeners $10 off your first month’s subscription and free shipping when you visit nutrafol.com promo code VINE.

Apartments.com: The place to find a place!

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.