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:
0:00 – Welcome + how Steph and Jill originally met
1:22 – Jill's story: when entrepreneurship "chooses you"
4:18 – The pressure of being a stay-at-home mom & identity conflict
7:06 – COVID, shutting down in-person marketing & learning digital skills
10:40 – Discovering website design + the birth of Cherry Picked WebCo
13:55 – Champagne & CEOs: the event that changed everything
16:42 – Commanding your fees, raising your rates & imposter syndrome
20:30 – How switching roles in marriage strengthened their relationship
25:14 – Homeschooling, honesty, and redefining family rhythms
28:55 – Living and dying by the calendar: structure as freedom
32:40 – Moving from New Jersey to Texas & building location independence
35:22 – Creating opportunities for your child through entrepreneurship
38:18 – Navigating seasons of marriage, teamwork & communication
42:05 – The importance of checking in with your spouse and recalibrating
45:44 – Closing thoughts + details on the January TWP Popup
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