The TrustBuilt Podcast

What happens when trust becomes the through-line of everything you build—your team, your brand, and your business partnerships?

In this episode of The TrustBuilt Podcast, host Alan Bennett sits down with Windy Elstermeier, CEO of Pivotal Solutions and founder of Jane Wick, to talk about the power of connection, compassion, and trust in leadership.

From her days leading teams at Walmart to launching a women-led gun range bag brand, Windy shares how learning to serve first, build meaningful relationships, and trust others (and yourself) can completely transform how you lead and grow.

You’ll hear:

✅ How authentic connection fuels both team engagement and customer loyalty

✅ The difference between facilitating and leading through storytelling

✅ What it takes to build partnerships rooted in mutual trust

✅ How serving others first can multiply business opportunities

✅ Why compassion is the hidden superpower in every strong culture

If you’ve ever wondered how to move from doing it all yourself to building through people, this conversation is for you.

👉 Learn more about building a business that runs on trust (not stress): www.trustbuiltsolutions.com

⏱️ Chapters

00:00 – Spotting a Gap: How Jane Wick Was Born

01:00 – From Training to Keynotes: Building Confidence on Stage

04:00 – The Role of Trust—In Yourself and Your Audience

07:00 – Connection and Compassion: The Core of Leadership

10:00 – Turning Speaking into Service: Adding Real Value

14:00 – Storytelling, Authenticity, and Lessons Learned

19:00 – Building Jane Wick: Trusting Partners Across Borders

28:00 – Community, Reciprocity, and the Power of Connection

---

Connect with Windy

🌐 https://pivotalsolutions.co/

🌐 https://janewick.com/

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

---

team engagement, building trust, leadership compassion, small business growth, culture that scales

What does it take to move from carrying your business alone… to building a team that’s engaged, trusted, and thriving?

In this episode of The TrustBuilt Podcast, host Alan Bennett sits down with Steve Toth of Crestline Leaders to explore the foundations of team building, culture, and engagement.

Steve shares his journey from scrappy solopreneur to leading teams inside Fortune 500 companies and startups, and what he’s learned about:

• Why purpose and vision matter for keeping teams aligned.
• 
  
• How personal values shape company culture (and why that attracts A-players).
• 
  
• The link between accountability, trust, and employee engagement.
• 
  
• What happens when leaders stop delegating and start abdicating—and how to fix it.
• 
  
• Why a flourishing team is the real key to scaling any business.
• 
  

If you’re tired of carrying your business on your shoulders and want a team that buys in, sticks around, and thrives—this conversation is packed with practical insights you can apply right now.

👉 Ready to build a team you can trust? Learn more at https://www.trustbuiltsolutions.com/.

⏱️ Chapters

00:00 Why maximizing value also maximizes employee happiness

01:00 How Alan & Steve met at a family business event

02:30 Steve’s entrepreneurial beginnings: lawn mowing & Volkswagens

07:00 Lessons learned from W-2 roles and building trust through relationships

09:20 From solopreneur to team builder: why “just me” doesn’t scale

13:20 The People & Culture Model: why culture is the foundation

15:20 Flipping over rocks: uncovering hidden issues in organizations

20:00 Vision: how clarity drives team alignment

23:00 Building sticky, authentic values that attract A-players

26:00 Purpose as the driver of passion and culture

29:00 Why accountability is “purpose’s first cousin”

30:30 How purpose + accountability fuel employee engagement

33:10 Prioritization, scaling, and the “triangle model”

36:00 Enterprise value: why engaged teams grow business value

42:00 The tipping point of trust: what happens when it clicks

45:00 Where to connect with Steve Toth

---

Connect With Steve Toth

🌐 https://www.crestlineleaders.com/

💻 https://www.linkedin.com/in/the-real-steve-toth/

team engagement, building trust at work, company culture, employee retention, small business leadership

What if your employees didn’t just “do their job”… but felt empowered to lead, make decisions, and act in the company’s best interest without waiting to be told?

That’s the culture Jonathan Brooks has built at Warehouse on Wheels, where his team scaled from 2 locations to 37,000 trailers in just a few years.

In this episode of The TrustBuilt Podcast, host Alan Bennett talks with Jonathan about how he shifted from a CFO mindset to a culture-first leader—and why employee engagement is the true engine behind growth.

You’ll learn:

✅ Why he gives every new hire The Ultimate Expectation letter to empower ownership from day one.

✅ How Gallup’s Q12 framework measures engagement and drives action.

✅ Why Extreme Ownership training became the backbone of their leadership culture.

✅ The role of learning & development in retaining top talent.

✅ How trust, empowerment, and equity create buy-in at every level.

If you’re a business owner looking to scale without burning out—or want your employees engaged like owners instead of clock-punchers—this conversation will change how you think about team building.

🎙️ Subscribe for more real-world stories of building businesses that run without the owner 👉 www.youtube.com/@trustbuiltpodcast

⏱️ Chapters

00:00 – Why trust matters in leadership

01:00 – Jonathan Brooks’ career path from CFO to CEO

04:00 – Building culture with Gallup Q12 surveys

06:00 – Learning emotional intelligence as a leader

08:00 – Launching a learning & development department

10:00 – The Ultimate Expectation: empowering employees from day one

12:00 – Hiring for attitude vs. aptitude

16:00 – Ritz-Carlton service at the Hampton Inn price

18:00 – Scaling through acquisitions & greenfield markets

20:00 – Onboarding with Extreme Ownership

23:00 – Field training exercises for leadership development

26:00 – Equity & rewards that drive buy-in

30:00 – Scaling easier with systems of trust

33:40 – Local market CEOs & agility at scale

35:20 – Trust + culture = engaged employees & loyal customers

37:00 – Succession planning & running without the owner

42:00 – Owner dependence kills deals (and how to avoid it)

---

Connect With Jonathan & Warehouse on Wheels

🌐 https://wowtrailers.com/

💻 https://www.linkedin.com/in/jnbrooksiv/

---

Are you a business owner who is ready to build your team, encourage employee engagement, & ensure your business can run without you?

👉 Set up a time to talk to Alan 

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

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

In this episode of The TrustBuilt Podcast, host Alan Bennett interviews Steven Schmitt 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.

---

🔗 Connect with Jessica & Silverlake Design Studio

🌐 https://silverlakestudio.com/

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

-----

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

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

----

🔗 Connect with Windy & discover Jane Wick

🌐 https://janewick.com/

🌐 https://pivotalsolutions.co/

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

-----

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

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

-----

🔗 Connect with Deme Yuan

🌐 https://freightrelay.com

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

-----

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

-----

🔗 Connect with Sam Russell & The Buttered Biscuit 

🌐 https://thebutteredbiscuit.com/

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

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

-----

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

-----

🔗 Connect with Ben Cashion

🌐 https://www.cornerstoneco.com/

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

-----

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

-----

🔗 Connect with Bryan Fittin

🌐 https://goroguestudio.com/

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

-----

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