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 startups to Fortune 500 giants like Disney.

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 family history of entrepreneurship as a significant influence on his career path. Jayden emphasizes his preference for driving trucks over office work, although he acknowledges the benefits of both.

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 professional services like CPAs and mastermind groups to ensure sustainable growth.

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 rewards of starting and growing his business.

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 by the desire to remain connected to the industry while providing solutions that save time and improve quality of life for contractors.