Roll Up & Roll Out

Hosted by Paul Childers

Business Investing

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Jun 2026

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About the show

Husband and father to 2 kids 11 and 6 business owner and educator. I work to help business owners understand lending better and get them access to loans that benefit them financially and personally by not abusing their personal credit and protecting their personal assets. I believe lending when used properly with the correct credit systems can be a huge boost to your business.

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44 recent

June 30, 202627 min

More Leads Won't Fix a Broken Business

In this episode of Roll Up & Roll Out , Paul sits down with Jenna Harris , founder of SmartOpsClub , to unpack one of the biggest myths in the home service industry: that more sales solve every problem. Jenna shares how growing up in a blue-collar family and now owning her own contracting business has shaped her passion for helping plumbing and HVAC companies build profitable, scalable operations. Together, they discuss why so many contractors become "busy but broke," how poor systems silently destroy profit, why understanding your financials matters more than most owners realize, and the importance of learning enough about every part of your business before handing it off. If you're a contractor or business owner who feels like you're working harder than ever but your bank account isn't showing it, this conversation will challenge the way you think about growth and give you practical insights to build a stronger business from the inside out

June 11, 202618 min

How AI Can Help You Compete Against Companies 10X Your Size

Matt Shepard, a business owner with a background in real estate investment and general contracting, discusses his journey into AI and automation, and how he helps other business owners implement AI solutions to improve their operations and compete with larger businesses. Takeaways Real estate investment and general contracting background Transition from real estate investing to AI and automation Helping small and medium-sized businesses compete with larger businesses using AI Chapters 00:00 Engaging with Matt Shepard

April 14, 202645 min

How Chuck the Plumber Built a $22M Business from Nothing

Chuck Staszkiewicz, also known as Chuck the Plumber, shares his journey of starting a plumbing company from his garage with zero capital and growing it to $22 million a year in revenue. He discusses the importance of setting up the right environment for success and the mindset of taking risks and making bold decisions in entrepreneurship. The conversation covers Chuck's journey as a business owner, the challenges he faced, and the lessons he learned. It also delves into the importance of mentorship, learning from mistakes, and the value of networking and relationships in business. Takeaways Environment for success Taking risks and making bold decisions Sales will win Be ready to receive information Understanding business finances is crucial Mentorship can accelerate business growth Relationship building is essential for business owners Chapters 00:00 Introduction and Journey to Utah 06:11 Starting a Business with Zero Capital 12:01 Taking Risks and Making Bold Decisions 17:56 Clarity and Direction in Entrepreneurship 23:26 Early Business Challenges 29:24 Learning and Understanding Every Position in the Business 36:04 The Role of Relationships and Networking in Business Growth

April 7, 202626 min

Stop Doing It All: How Smart Owners Leverage People

The conversation delves into Nathan's entrepreneurial journey, from his early life experiences to the challenges and lessons learned in business ownership. It explores the transition from business ownership, the importance of hiring and managing employees, and the significance of compartmentalizing business ventures. Additionally, it highlights personal productivity, networking, leveraging human equity, hiring based on character, and venturing into the cannabis industry. Takeaways Entrepreneurial Journey Business Ownership Challenges Chapters 00:00 Early Life and Introduction to Business 08:21 Hiring and Managing Employees 15:32 Leveraging Human Equity 21:30 Venturing into the Cannabis Industry

April 7, 202630 min

Built on Discipline: A Veteran’s Approach to Business

The conversation delves into the challenges of transitioning from military to business life, the importance of accountability and culture in business operations, the significance of documentation and processes, and the value of mentorship and learning from experiences. The guest shares insights from his own journey and highlights the need for adaptability, accountability, and a strong company culture in the business world. Takeaways Adaptation to civilian life after military service Importance of accountability and culture in business The significance of documentation and processes in business operations The value of mentorship and learning from experiences Chapters 00:00 Transition from Military to Business 10:21 Accountability and Culture in Business 21:00 Mentorship and Learning from Experiences

April 7, 202622 min

The 90-Day Shift That Can Transform Your Business

The conversation with Anthony Moses covers the journey of a firefighter turned flooring contractor and business consultant. It delves into the challenges of the contracting industry, the transition to 90-day clarity sessions, the role of virtual assistants, and the impact of systems and processes on business growth. The importance of proactive preparation and the value of virtual assistants in reducing stress and offloading tasks are key takeaways from the discussion. Takeaways Virtual assistants provide valuable support for business owners in the contracting space. The importance of implementing systems and processes to offload tasks and reduce stress. Chapters 00:00 Introduction and Background 05:05 Virtual Assistant and Business Growth 13:17 Impact of Systems and Processes 19:25 Importance of Proactive Preparation

April 7, 202622 min

The Hidden Cost of Bad Bids

The conversation with Chase Hennessey, owner of Home and Grounds, covers the journey of starting and growing a business, focusing on quality over quantity, the role of design in client engagement, lessons in business growth and collaboration, employee management, seasonal business challenges, and the importance of quality bidding and client satisfaction. Takeaways Quality over quantity Collaboration and networking Chapters 00:00 Quality Bidding and Client Satisfaction

April 7, 202624 min

If You’re Not Tracking This, You’re Losing Sales

The conversation delves into the significance of sales processes for small business owners and the importance of understanding and leveraging data for sales success. It also explores the complexity of sales and leadership, as well as the role of metrics and data in sales. Takeaways Sales processes are crucial for small business owners Understanding and leveraging data is essential for sales success Chapters 00:00 Metrics and Data in Sales

April 7, 202621 min

Building It Right Before It Starts: Lessons from North Star Earthworks

The conversation with Andy Pittman from North Star Earthworks LLC covers his journey into construction, the unique perspective of combining tree work and land clearing, coaching and guiding homeowners, pre-planning and cost savings, valuing people and business integrity, implementing systems and processes, learning from past experiences, business and marriage, and understanding self-worth and collaboration. Takeaways Combining tree work and land clearing provides a unique perspective on the build process Effective communication and partnership with customers and contractors lead to successful projects Chapters 00:00 The Journey into Construction 05:31 Pre-planning and Cost Savings 14:23 Learning from Past Experiences

May 13, 2024Episode 2618 min

The Transformation from Contractor to Estimating Expert with Ben Brunni

The owner of PayDirt Support Services, LLC, exploring his journey from being an excavation contractor to founding a company specializing in estimating, bidding, and GPS modeling for excavation contractors. Ben shares insights into the challenges faced in the excavation industry, such as the extensive hours devoted to estimating and bidding, leading to burnout. His entrepreneurial shift was driven by the desire to remain connected to the industry while providing solutions that save time and improve quality of life for contractors.