Thinking about leaving corporate life to build your own business? 

In this episode of The TrustBuilt Podcast, host Alan Bennett sits down with Windy Elstermeier to talk about the courage, risk, and strategies it takes to step out of a steady paycheck and create a business that can thrive on its own.

Windy spent 17 years at Walmart before making the leap into entrepreneurship. She shares the hard lessons she learned—like managing cash flow, setting up systems, and facing the reality of risk—as well as the wins of scaling, hiring, and eventually selling her first business.

If you’re a business owner dreaming of freedom, or if you’re stuck in the grind and wondering if your company could ever run without you, this episode will give you practical tools and inspiration.

🎙️ Subscribe for more stories of entrepreneurs building trust-driven, self-sufficient businesses.

📌 Chapters

00:00 – Leaving Corporate After 17 Years at Walmart

02:14 – The Spouse Conversation: Getting Buy-In at Home

04:50 – Doing the Due Diligence: Numbers, Franchises & P&Ls

06:22 – Taking the Leap: Fear, Excitement, and Risk

08:45 – The Obstacle of Cash Flow and Bookkeeping Mistakes

11:26 – Adjusting from Paychecks to Revenue Fluctuations

13:17 – Lessons on Hiring and Managing Crews

15:27 – Why Every Day as an Entrepreneur Involves Risk

16:14 – Big Wins: Family in the Business & Hitting Sales Goals

19:12 – Selling the Painting Company & Discovering Consulting

22:34 – Finding Passion in Solving Business Problems

23:55 – Launching Jane Wick: Spotting a Market Gap for Women

28:09 – Pitch Competitions, Mentors, and Validating Ideas

33:00 – The Importance of Multiple Mentors in Business Growth

36:10 – Preparing for Investors & Writing the Next Book

38:06 – Advice to Her Younger Self About Entrepreneurship

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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

leaving corporate for entrepreneurship | build a business that runs without you | how to start a small business after corporate | risk and trust in business | scaling and selling a business