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

What happens when a social worker takes the leap into the logistics tech world?

Deme Yuan, co-founder and COO of Freight Relay, shares her unlikely path from nonprofit leadership to revolutionizing long-haul trucking. In this episode of the TrustBuilt Podcast, host Alan Bennett explores how Deme's passion for social equity fuels innovation in an industry ripe for disruption.

This is a story of mission-driven entrepreneurship, family partnership, and grit.

⏱️ Chapters:

00:00 – Why Not All Feedback Is Equal

01:00 – Meet Deme Yuan & the Freight Relay Mission

03:00 – From Social Work to Startups: Deme’s Unexpected Journey

05:45 – A Book That Sparked a Business Idea

08:00 – Angel Funding, India, and Building a Dev Team from Scratch

10:00 – Startup Accelerator Life & First Traction

12:00 – Bentonville, AR: A Logistics Hub in Disguise

13:00 – Pivoting During the Pandemic

14:00 – Winning Federal Grants (SBIR, DOE, USDA, NSF)

16:00 – How a Nonprofit Background Prepared Her for Startup Life

17:00 – Starting a Business with Your Spouse: The Real Talk

20:00 – Changing Her Mindset Around Business & Impact

21:00 – The Role of Mentorship & Discernment

25:00 – Serving Truckers, Communities & a Bigger Mission

31:00 – Work-Life Balance for Drivers: What Equity Looks Like

34:00 – Busting the Myths of Small Business Ownership

37:00 – The Cost of “Letting Off the Gas” as a Founder

39:00 – Sustainability vs. Hustle: Building for the Long Game

40:30 – A Letter to Her Younger Self (Wise Words!)

42:40 – Where to Find Deme & Freight Relay Online

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🔗 Connect with Deme Yuan

🌐 https://freightrelay.com

LinkedIn: https://www.linkedin.com/in/demeyuan/

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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

Whether you're leading a team, building a brand, or trying to step out of daily operations, this episode is a masterclass in values-based growth!

In this episode of The TrustBuilt Podcast, Alan sits down with Sam Russell, co-founder of the thriving breakfast spot The Buttered Biscuit. What started as his wife’s idea has grown into a purpose-driven business with 200+ employees and 10,000 guests served weekly. Sam shares how culture, consistency, and care have powered their growth—not just in biscuits, but in impact.

From training future doctors in the kitchen to creating second chances for the underestimated, Sam opens up about the kind of leadership that builds trust and changes lives.

⏱️Chapters:

01:16 – From Corporate to Biscuits: How It All Started

02:00 – The Real Founder Behind Buttered Biscuit

04:01 – Building Through Community Connection

05:03 – Food, Trust & the Power of the Table

07:10 – Consistency in Business and Biscuits

08:25 – The Five Core Values Driving the Company

11:00 – Culture as a Living, Breathing System

13:04 – Hiring for Flourishing, Not Just Filling Roles

15:04 – Recognizing Employees & Building Confidence

19:03 – Systems That Support Human-Centered Leadership

22:28 – Avoiding the “Dish Pit Trap” as a Business Owner

25:51 – Why Every Entrepreneur Needs a Refill Point

26:18 – Project Biscuit: Serving the Underestimated

30:30 – Confidence, Second Chances & Accountability

34:32 – A Real Story of Redemption and Career Growth

36:09 – Accountability as Empowerment

37:41 – Why Mastery Builds Confidence (and Opportunity)

42:02 – Final Thoughts on Leadership & Listening

44:00 – Book Recommendations for Leaders & Families

46:52 – Locations, Catering, and What’s Next

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🔗 Connect with Sam Russell & The Buttered Biscuit

🌐 https://thebutteredbiscuit.com/

Instagram: https://www.instagram.com/thebutteredbiscuit/

LinkedIn: https://www.linkedin.com/in/smjrussell/

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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

In this conversation, Ben Cashion—CEO coach, startup veteran, and former licensed counselor—dives deep into what it really takes to build trust as a leader in today’s skeptical world.

We explore the emotional weight of leadership, why trust is so hard to come by (and so valuable when you earn it), and how founders can create lasting impact through clarity, compassion, and confidence.

Whether you're a startup founder, scaling CEO, or just feeling the pressure of leading people and making payroll, this episode offers real-world insights for building a business that works—and a leadership style that earns trust.

⏱️ Chapters

00:00 – Trust is Broken… So Now What?

01:15 – Ben’s Unusual Path: Counselor Turned CEO Coach

03:10 – How Therapy Training Enhances Coaching

05:00 – Coaching vs. Consulting: What’s the Difference?

07:00 – Finding Your Voice and Style as a Leader

09:15 – Trust Starts with Competence and Confidence

12:00 – Startup Scars and Founder Wisdom

15:00 – The Hidden Weight Founders Carry

17:30 – How to Build Trust Through Shared Perspective

20:00 – Teaching Your Kids (and Team) Compassion

22:30 – Clarity: The Antidote to Ambiguity

25:00 – When Emotion Shows Up in the Boardroom

28:00 – Knowing When to Lead with Space vs. Direction

30:00 – Self-Awareness and Emotional Intelligence

33:00 – Coaching Leaders Through Conflict

36:00 – The Power of Preparing for Hard Conversations

39:00 – Layering EQ into Business Strategy

41:15 – Why Every Leader Needs to Script Hope

42:30 – Ben’s Top Book Picks for Leaders

44:00 – Why Building Trust Is Your Business Advantage

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🔗 Connect with Ben Cashion

🌐 https://www.cornerstoneco.com/

LinkedIn: https://www.linkedin.com/in/ben-cashion-5703a5b8/

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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

In this episode of The TrustBuilt Podcast, Bryan Fittin pulls back the curtain on how he built a video content agency that helps business owners build trust, lead with clarity, and scale their companies without burning out.

From hiring the right people to maximizing the ROI of content, Bryan shares the mindsets and systems that make Go Rogue Studio thrive.

If you're a business owner, entrepreneur, or leader who wants to grow your influence while reclaiming your time, this conversation is for you.

⏱️ Chapters

00:00 – Why empathy matters in content creation

02:13 – Bryan’s origin story & Go Rogue Studio overview

04:00 – Why video builds trust and connection faster

06:20 – That one trade show moment that changed everything

08:00 – Helping clients get comfortable on camera

10:30 – How to think beyond the script: Serve the person, not the lens

13:20 – From podcast to content engine: Why structure matters

14:45 – Using content for onboarding, training & team clarity

16:20 – Don’t just make content—maximize it

18:00 – Cajun cooking, gumbo, and getting more from what you already have

20:00 – Creating content with strategy, empathy, and the end in mind

22:00 – Scaling the team: hiring for will, not just skill

24:00 – The “Buy Back Your Time” mindset shift

26:00 – Hiring mistakes, attitude over aptitude, and building culture

30:00 – Coaching, winning moments, and chasing clarity

34:00 – What if everything goes right? A mindset shift for leaders

37:00 – People-first processes and strengths-based leadership

40:00 – Clients as friends: the power of trust-driven business

43:00 – Pricing conversations and value alignment

48:00 – Final thoughts on trust, growth, and meaningful work

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🔗 Connect with Bryan Fittin

🌐 https://goroguestudio.com/

LinkedIn: https://www.linkedin.com/in/fittin/

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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

If you're exhausted from grinding in your business, this episode is your wake-up call.

Coach and leadership expert Bryan Yates joins The TrustBuilt Podcast to challenge the hustle mindset and explore what it really takes to build a self-sustaining business. Bryan unpacks the hidden leadership habits that cause burnout—and how to break free.

Whether you're looking to exit your business, build a stronger team, or stop white-knuckling your way through entrepreneurship, this episode offers clarity, courage, and practical tools to lead differently.

⏱️ Chapters

00:00 – Why You’ll Never Exit Without Empowering Others

00:22 – Meet Bryan Yates: From Athlete to Leadership Coach

01:15 – Grit vs. Flow: Redefining What It Means to Push Through

04:46 – The Grind Trap: Why Business Owners Burn Out

08:35 – Building Mental Fitness to Push Past Resistance

13:41 – What Your Body Language Reveals About Your Mindset

15:39 – The Role of Self-Awareness in Great Leadership

22:13 – Motivation & Intentions: What Drives Your Actions?

30:33 – When It’s Time for a Team Member to Move On

32:16 – Clarity, Impact, and Why Your Vision Matters

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🔗 Connect with Bryan Yates

🌐 https://locomotivcoaching.com/

LinkedIn: https://www.linkedin.com/in/bryanyates/

📰 Sign up for Bryan's newsletter: Shift Happens

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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