Leaving a secure corporate career to step into entrepreneurship is never easy, but it’s often where true leadership is forged.

In this episode, Alan sits down with Windy Elstermeier—a former Walmart leader turned serial entrepreneur and business consultant. Windy shares her remarkable journey from corporate America to franchising, launching multiple businesses, writing books, and now building a product brand (Jane Wick) designed for women in the shooting sports community.

If you’re a business owner, entrepreneur, or leader looking for inspiration and actionable insights, this conversation is packed with wisdom you can apply right away.

⏱️ Chapters

00:00 – Windy’s transition from corporate America to entrepreneurship

02:14 – Talking with family about leaving a corporate career

04:16 – Due diligence: choosing a franchise and running the numbers

06:31 – Taking the leap: the excitement and fear of business ownership

08:20 – Early challenges: financials, bookkeeping, and cash flow struggles

11:07 – Risk-taking and adjusting to life without a corporate paycheck

15:27 – Big wins: family involvement and building momentum

18:46 – Selling the first business & pivoting into consulting

21:28 – Finding her passion in business strategy and solving problems

23:17 – Launching Jane Wick: creating products for women entrepreneurs in a niche market

28:16 – Pitch competitions, market validation, and building prototypes

32:14 – The power of mentorship and “out-dreaming” those around you

35:48 – Learning to lead differently in new ventures and seeking investors

37:20 – Writing her second book & the MOVE–PLAN–SAVE–GROW–LEAD series

38:06 – Advice to her younger self: stepping onto the invisible bridge

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🔗 Connect with Windy & discover Jane Wick

🌐 https://janewick.com/

🌐 https://pivotalsolutions.co/

LinkedIn: https://www.linkedin.com/in/windy-elstermeier/

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Are you a business owner who is ready to break free from the day-to-day grind & build a self-sustaining company?

👉 Set up a time to talk to Alan

🔗 https://www.trustbuiltsolutions.com/contact