E133 From Stay-at-Home Mom to CEO: Jill Cherry's Reinvention

In this episode of The Wealthy Practitioner Podcast, Steph sits down with longtime friend and entrepreneur Jill Cherry— founder of Cherry Picked WebCo (@cherrypickedwebco) — for one of the most honest and expansive conversations we've had on the show.

Jill's story is a powerful example of what happens when identity, motherhood, marriage, and entrepreneurship collide — and what becomes possible when a woman finally decides to build a business on her own terms. From helping run her husband's chiropractic practice, to navigating the pressure and guilt of being a stay-at-home mom, to accidentally discovering the skillset that would change her entire life, Jill shares the journey that led her to build a thriving online business that now supports their entire family.

Steph and Jill dive into the identity shifts required to trust yourself, raise your standards, and command your value. They explore the real dynamics of marriage during seasons of role reversals, the pressure of being the breadwinner, and how switching responsibilities ultimately saved their relationship. Jill also opens up about homeschooling, structure, creativity, and what it looks like to build a business that gives your child access to the best opportunities — including moving their entire family from New Jersey to Texas.

This is an inspiring, grounded, and deeply relatable conversation for any woman who has ever felt torn between motherhood and ambition, questioned her next move, or battled imposter syndrome on her rise to the next level.

In this episode, we cover:

00:00 Intro: why Jill's story matters + entrepreneurship, motherhood, and freedom

01:15 Jill's path into entrepreneurship: from chiropractic support to online business

03:05 COVID pivot: learning digital marketing and discovering web design

04:50 First leap into business: charging fees, confidence, a...