Do you ever wonder if your business could run without you?

In this episode of The TrustBuilt Podcast, host Alan Bennett interviews Steven Schmidt, co-founder of Willow Financial, about building a trust-driven business that thrives even when the owner steps away.

Steven shares his real-world experience of going from sleepless nights as a solo founder to creating a team and systems that allow his firm to grow without constant oversight. From how to trust your team, to creating business systems that work, to succession planning and exit strategies, this episode is packed with insights for business owners who want freedom from the daily grind.

Whether you’re looking to scale your company, prepare it for sale, or simply take a real vacation without everything falling apart—this conversation will give you practical strategies to build a self-sufficient, owner-independent business.

🎙️ Subscribe for more conversations on how to build a business that runs without you.

00:00 – Radical Trust: Why Willow Shares a Company Inbox

02:42 – From Solo Founder to Building a Scalable Firm

05:22 – Creating “Light Bulb” Moments for Clients

09:41 – Sleepless Nights and Entrepreneur Pressure

11:26 – Hiring Your First Team Member (and Lessons Learned)

13:05 – Planning for Succession & Exit Strategy

15:02 – Building Trust with Clients and Teams

17:17 – Why Transparency Builds Business Value

21:27 – Onboarding Clients with Clarity

23:24 – Helping Owners Face Estate & Succession Planning

27:21 – What the “Right Client” Looks Like

29:31 – Passion, Purpose & Trust Beyond Yourself

31:17 – What Steven Would Do Differently

32:10 – How Willow Uses AI as a Business Thought Partner

34:53 – How to Connect with Steven

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

business that runs without you | how to trust your team | business systems and processes | succession planning small business | owner independent business

If you're an entrepreneur craving freedom, purpose, and a team you can trust, this episode is for you.

Jessica Crum, founder of Silverlake Design Studio, shares her incredible journey from the high-pressure world of Los Angeles fashion to building a thriving marketing agency in Arkansas.

In this inspiring conversation Jessica opens up about career pivots, the real struggles behind entrepreneurship, building a mission-driven brand, and stepping away from hustle culture to create a sustainable, impact-driven business.

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🔗 Connect with Jessica & Silverlake Design Studio

🌐 https://silverlakestudio.com/

LinkedIn: https://www.linkedin.com/in/jessica-crum/

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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 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