Josh Key, a former plumbing business owner from Dallas-Fort Worth, shares his turbulent partnership journey. He reveals the pitfalls of inadequate due diligence when partnering with a master plumber and the chaos that ensued when his partner's wife became involved. The breakdown of trust led to clients and employees leaving, and ultimately, Josh had to close the business and file for bankruptcy. His story is infused with lessons about the importance of verifying partners and maintaining emotional control in business, guided by his faith.

Tom Matter, co-owner of ProDuct Cleaning, transitioned from tech to entrepreneurship, teaming up with his brother, Dawson Matter, to run a vent cleaning business. They discuss the challenges of operating a nocturnal business, from managing customer complaints to upgrading equipment. Tom juggles his tech job while Dawson handles operations. The duo also reveals their struggles with employee communication and the difficulties of chasing payments from clients, all while maintaining an impressive 42% profit margin.

Fred McGill, owner of Bray Electrical Services, shares his journey from real estate entrepreneur to acquiring a $3.2 million electrical business. He discusses the growth potential in the electrical sector, predicting a 25% revenue increase in the first year. Fred emphasizes the importance of digital marketing, effective hiring practices, and reassuring employees during ownership transitions. He contrasts the financial commitments of small businesses with real estate investments and offers insights into navigating SBA loans and licensing challenges in the trades.

Jordan Dubin, co-founder of Guild Garage Group, shares his remarkable journey scaling a garage door repair business through acquisitions. He details how he and his partners exceeded their five-year revenue goal in just one year. Jordan discusses the power of handwritten letters to potential sellers and maintaining local brands. He explains the strategic importance of trust in partnerships and why private equity hasn’t dominated this market yet. The conversation highlights his innovative approaches to sourcing deals and the critical role of timing in successful acquisitions.

Jonathon Tupper, owner of JSI Factoring, shares his journey from investment management to the niche of asset-based lending. He discusses the lucrative opportunities in factoring, especially for small businesses seeking liquidity. Jonathon highlights the unique challenges of acquiring a factoring business, from competing with banks to managing operations remotely. He also addresses the importance of building strong client relationships and shares insights on hiring in a tight labor market, offering invaluable tips for aspiring entrepreneurs.

Michael Johnson is the owner of SpeedPro Northwest Raleigh, a printing business he acquired after a diverse career, including military service. In this engaging discussion, he shares the ups and downs of his acquisition journey, including his frustrating first day as an owner and the thrilling high demand for printing car wraps. Michael emphasizes the importance of empowering employees and even hired his wife to join him in the business. His transition from a W-2 job to entrepreneurship illustrates the emotional rewards of ownership and the appeal of the franchise model.

Link Moser, owner of Windhill Designs, shares his journey of building a portfolio through micro-acquisitions of web design and hosting businesses. He discusses starting out in web development in the 90s and his strategic outreach to acquire agencies. The conversation dives into the challenges of customer retention during transitions and the emotional ups and downs of managing a nearly-passive income. Moser also reflects on the balance of entrepreneurship with family life and his thoughts on potentially venturing into traditional businesses.

Derek Croft, a former Bain & Company consultant, shares his journey of acquiring Lice Doctors, a national lice treatment business. He discusses the unique challenges of running a niche business, including high staff turnover and competitive dynamics. Derek emphasizes the personal satisfaction derived from helping families in need while navigating early hurdles like a payroll crisis. He also highlights the importance of marketing strategies and technology improvements for operational efficiency, all while aiming to double the business size in five years.

Francisco del Rio and Diego Silva, co-founders of LATAMVet, are revolutionizing the veterinary market in Chile. With backgrounds in engineering and finance, they share their inspiring journey from corporate careers to entrepreneurship. They discuss the challenges of trust and valuation during clinic acquisitions, emphasize building relationships with sellers, and navigate the complexities of operating during COVID-19. Their innovative strategies focus on digital management systems and a vision for expansion into neighboring countries, fueled by the growing trend of pet humanization.

Sam Rosati, an entrepreneur and lawyer known for establishing the largest commercial fencing contractor in the Sunbelt, shares his entrepreneurial journey. He discusses the inspiring influence of Chenmark and his transition from accounting to independent sponsorship. The conversation reveals insights into acquiring and consolidating businesses, the luck involved in success, and the importance of strong operational teams. Sam also highlights the strategic growth through acquisitions and differentiates between independent sponsors and self-funded searchers, offering valuable lessons for aspiring entrepreneurs.