Episode 389: From Startup to PE Exit in Three Years with Josh Davis

From ten years of entrepreneurial struggles to PE exit in three years, Josh Davis shares proven strategies for scaling through acquisitions, building proprietary systems, and navigating the identity shift that follows a successful exit. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Josh Davis, CEO of JL Davis Enterprises, a five-time founder, business acquirer, and turnaround expert with multiple exits including to a US private equity-backed firm. Josh built one of Canada's fastest-growing logistics startups alongside his wife Loretta, scaling it from the ground up before it was acquired by one of North America's largest transportation companies just three years after launch. WHAT YOU'LL LEARN: In this episode, you'll discover how to scale a company through strategic acquisitions without outside capital, why building proprietary software became a major competitive advantage, and what the post-sale transition really feels like when you stay on as CEO. Josh shares the visionary and integrator partnership dynamic that creates breakthrough results, why most post-exit entrepreneurs struggle with minority investments, and what freedom means when you deliberately keep your family office smaller than outside investors want. JOSH'S JOURNEY: Josh's entrepreneurial drive started early watching both grandfathers build successful businesses. On his mother's side, his grandfather ran a construction company, warehouse business, and real estate ventures. On his father's side, his grandfather was a successful mining entrepreneur who became Josh's closest mentor. But Josh also saw his parents go through financial struggles and divorce, which made him view entrepreneurship as the path to stability rather than risk. In his early twenties, Josh dropped out of business school when his grandfather became sick with cancer. He spent two years learning about business and understanding how to acquire distressed mining properties. After his grandfather passed, Josh got exposure to acquisitions, due diligence, and integration through his grandfather's connections. But for the first ten years, he didn't understand the real importance of building teams, building systems, and building a real company. THE TURNING POINT: At twenty-eight, Josh made a deliberate decision to actually learn how to be an entrepreneur. He read every business book he could find, connected with mentors, and joined a private peer advisory group with seasoned entrepreneurs in their sixties, seventies, and eighties. That group has been a game-changer for thirteen years. A few years later, he married his wife Loretta. Their skills were completely opposite. Josh was the visionary with strengths in leadership and sales. Loretta brought systems, processes, and operational excellence from her commerce degree at one of Canada's top universities. The combination created the breakthrough. BUILDING THE LOGISTICS COMPANY: When Josh and Loretta launched their logistics company, they realized the Canadian transportation industry was old school with manual processes and paper systems. They couldn't find software that fit their needs, so they hired four developers and built their own. After eight months, they launched custom software that tracked gross profit per head, enabled profit-sharing structures, and attracted top talent. The second key was acquisitions. They bootstrapped with bank debt and systematically acquired distressed transportation and warehousing businesses, bringing in their own software, systems, and team members. After developing their operating system for acquisitions, each deal got easier. THE PE EXIT: The conversation about selling started when Loretta raised it. She was pregnant with their first child and knew she didn't want to run operations in a 24/7 transportation logistics business. They had also hit a capital constraint since the low-margin business required more capital every time they grew. They engaged an M&A advisor and found a well-capitalized US private equity-backed firm with Canadian roots in North American transportation. POST-SALE TRANSITION: Josh describes post-exit life as giving a child up for adoption and living in the same house. He stayed on as CEO for two years, and having financial backing from the larger entity was a huge relief. But when the transition ended, his partners were gone, his wife had been out for two years, and the company had become more corporate. The day he told the team was emotional, and when his email was finally turned off, the quiet was striking. KEY INSIGHTS: Josh's original plan post-exit was to take small equity positions and sit on boards. What he found was that he actually likes getting his hands dirty, and working with founders who weren't ready for the advice proved challenging. Some founders would realize they didn't want to do the work and would ask Josh to buy them out instead. That misalignment led JL Davis Enterprises to pivot toward full acquisitions while being ...