Roll Up & Roll Out

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 operati...

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 H...

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 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 e...

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 cult...

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 red...

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 Collaborati...

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 succes...

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 coll...

Having worked in various roles involving trucks, tractors, and heavy equipment, Sean discusses his transition into entrepreneurship, combining construction and agricultural services.

A performance digital marketing agency specializing in lead and revenue generation through paid ads for home services, e-commerce, and SaaS businesses. Mason shares his journey from an initial career in sports management to pioneering digital marketing strategies, including overseeing $150 million in ad spend and generating over a billion dollars in sales for a wide range of companies, from startu...

Malcolm Watt, the owner of Junk Truck MN, a junk removal company in Southern Minnesota. Malcolm shares his 14-year journey from being a sheet metal fab shop foreman to creating a thriving business in an industry that saw a boom during the COVID-19 pandemic. He discusses how diversification, such as downsizing household cleaning and recycling services, has been key to his success.

Jayden Hughey, the co-founder of Lawn Lake Logistics. They discuss the differences between operating a trucking company and working as a broker in the transportation industry, particularly within flatbed and agriculture-oriented markets. Jayden shares insights into how his childhood obsession with trucks led to a career and eventually to starting a business with his wife. He cites a deep-rooted fa...

Jaybird, the owner of Cross Country Wellness, a company founded amidst COVID-19 in 2020. Jaybird shares his personal story of losing his father to an accidental overdose of pain pills, which motivated him to start a business focusing on plant-based medicine for pain, sleep, anxiety, and inflammation relief, as an alternative to traditional pharmaceuticals.

Delphi Plumbing and Heating, a family-run, unionized business specializing in wastewater treatment work for NYC's DEP. Dimitri shares insights into his journey from sweeping floors to vice presidency, highlighting the significance of family mentorship, mental toughness, and the importance of nurturing a company culture that aligns with core business values.

The owner of Sprinter Business Solutions. Tiffany shares his journey from starting his business right out of high school to navigating through financial and operational hurdles, and eventually expanding into a multi-million dollar enterprise. He touches on the early challenges of starting a business at a young age, the importance of continuously learning and adapting, and the value of investing in...

The owner of Window World of Fargo, who shares his journey from being a carpenter to owning his successful franchise. Carter discusses his background of hard work and adaptation through the recession, leading to a realization of his sales skills and eventual entrepreneurship with Window World. He highlights the importance of goal setting, support from his wife and brother, and the challenges and r...

The couple recounts how a chance Facebook interaction rekindled their relationship, which eventually led them into the farming business. Together, they've managed a tree farm since 2005, diversified into cattle farming, hay production, and even manage a seasonal antique and Christmas tree sales business.

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...

The importance of getting started, learning on the job, building a network, and the critical role of hard work and attention to detail in his success.

Delves into the cultural aspects and personal anecdotes related to dealing with death, highlighting the societal awkwardness around discussing the inevitable end. Davis and Childers discuss the emotional and financial benefits of pre-planning, aiming to alleviate the burden on families during difficult times.

Discover what drove Adolfo to start his own business in 2006 after an eight-year stint at a Fortune 500 company. A shift from a close-knit business environment to a rigid corporate structure pushed him to create a company that maintained a strong connection with its personnel and clients.

How does one keep their spark amidst the oil spills of everyday tasks and business challenges? Our guest lights the way by sharing the importance of focusing on what drives you, alongside the nuts and bolts of business mechanics. Feeling stuck in neutral on your own entrepreneurial road? Gear up for a story that might just kick you into overdrive. Your next pit stop could be this inspiring episode...

Fed up with watching your marketing bucks disappear without a trace? We’ll let you in on the ultimate detective work – tracking your spend and figuring out exactly what’s delivering the goods. It's marketing made transparent, something that’ll have every dollar accounted for and working its hardest for you.

Learn the art of growing more than just grass – explore the power of evolving from an employee to an entrepreneur with passion, purpose, and a whole lot of perseverance. How does a landscaper's journey mirror your own path to success? Tune in, and you might just unearth the secret to flourishing both in business and life.