E133 From Stay-at-Home Mom to CEO: Jill Cherry’s Reinvention
Release Date: 12/09/2025
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info_outlineIn 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, and imposter syndrome
06:30 Power of getting in the room: retreats, belief expansion, and raising standards
07:55 Location freedom: replacing clinic income and moving states
09:15 Deep work vs admin work: protecting CEO time
10:40 Structuring time as a mom entrepreneur: living by the calendar
12:05 Moving to Texas: family decisions, baseball, and opportunity creation
13:40 Homeschooling honesty: choosing what actually works for your family
15:15 Role reversals in marriage: switching provider roles and saving the relationship
17:00 Riding seasons together: support, sacrifice, and communication
19:10 Closing + January popup invite
If you’re ready to be in the room where identity shifts, clarity drops in, and your next level becomes non-negotiable, join us inside our January TWP Popup in St. Pete. Two days. A powerful room. And the breakthroughs that change everything.
👉🏼Secure your ticket here: https://go.stephaniewigner.com/payment-link/68dfebcc613b1be417ce7d2e