From Startup to PE Exit in Three Years with Josh Davis
Feb 04, 2026
In this episode of the DealQuest Podcast, I sat down with Josh Davis, 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, scaling it from the ground up before it was acquired by one of North America's largest transportation companies just three years after launch. Today he runs JL Davis Enterprises alongside his wife Loretta, acquiring businesses and consulting founders on how to scale, build high-performance teams, and prepare for exit.
What makes Josh's story compelling is the decade of lessons that preceded his breakthrough. He spent ten years grinding through real estate, technology, and mining ventures before the combination of the right partner, the right systems, and the right industry came together. Josh brings a no-fluff, people-first approach grounded in faith and family values. He's been named one of Canada's Top 40 Under 40 and believes true success means building a business that serves your life, not the other way around. Whether you're considering an acquisition strategy for growth, preparing your company for a PE exit, or figuring out what comes after you sell, this conversation delivers real-world insights from someone who has lived through every stage.
LEARNING ENTREPRENEURSHIP FROM TWO GRANDFATHERS
Josh's entrepreneurial drive started early. He was fortunate to grow up watching both of his grandfathers build successful businesses. On his mother's side, his grandfather was essentially the mayor of his town while also running a construction company, a warehouse business, and real estate ventures. On his father's side, his grandfather was a successful mining entrepreneur who became a close mentor.
Seeing them build businesses, employ people, and make an impact in their communities planted the seed. But Josh also saw the other side when his parents, who were not entrepreneurs, went through financial struggles and eventually divorce. That experience created an unexpected motivation. Rather than viewing entrepreneurship as risky, Josh saw it as the path to stability for his future family.
THE FIRST TEN YEARS OF GETTING IT WRONG
Josh is candid about the fact that it took him a full decade to really understand entrepreneurship. In his early twenties, he dropped out of business school when his grandfather became sick with cancer. He spent two years with his mentor and hero, learning about business, hearing deal stories from his grandfather's old partners, and understanding how to acquire distressed mining properties and turn them around.
After his grandfather passed, Josh got his hands dirty in the mining industry through connections his grandfather had made. He learned about acquisitions, due diligence, and integration by being in proximity to experienced operators. It was essentially an MBA in deals. But for the first ten years, he was too focused on outworking the competition through sheer grit. He had some success, but he didn't understand the real importance of building teams, building systems, and building a real company.
THE STORM THAT TAUGHT HIM ABOUT LEADERSHIP
One of the most formative experiences came during a sailing trip with his grandfather. They planned to sail from Vancouver to the Sea of Cortez in Mexico. The first four days were beautiful and calm. Then they hit a massive storm with what felt like forty-foot waves while his grandfather was asleep below deck.
Josh and the crew weren't prepared. They made it through three or four hours of what he describes as hell, and when his grandfather finally woke up at the end, he couldn't believe what had happened to his boat. The parallel to business leadership became clear. Storms will come. Challenges will hit. The question is whether you have the right team, the right preparation, and the right systems in place when they do.
THE TURNING POINT AT TWENTY-EIGHT
At twenty-eight, Josh made a deliberate decision to actually learn how to be an entrepreneur. He started reading every business book he could find, studied biographies, connected with mentors, and joined a private peer advisory group with seasoned entrepreneurs who were decades ahead of him. Some were in their sixties, seventies, and one in his eighties. That group has been a game-changer, and he's still part of it thirteen years later.
A few years later, he married his wife Loretta. Their skills were completely opposite. Josh describes himself as school of hard knocks with strengths in leadership, sales, and putting the right teams in place. Loretta graduated from one of Canada's top universities with a commerce degree and brought systems, processes, and operational excellence. The combination created the breakthrough.
BUILDING PROPRIETARY SOFTWARE AS A COMPETITIVE ADVANTAGE
When Josh and Loretta launched their logistics company with their business partners, they quickly realized the transportation industry in Canada was old school. Most companies relied on manual processes, paper systems, and outdated methods for dispatching and routing trucks. Loretta's background in software at a major international shipping company gave them an idea.
They went to market looking for software that fit their needs and couldn't find anything. So they reluctantly decided to build it themselves, hiring four full-time developers. This was 2016, before AI could help with programming. After about eight months, they launched their custom software. Josh went from skeptical about the investment to completely sold. They could customize everything, track gross profit per head, design profit-sharing structures, and gamify the business in ways that helped both leadership and team members understand performance.
The software became a massive recruiting advantage. In western Canada, there weren't many tech-focused logistics companies. They could attract MBA graduates and top talent from outside the industry because of the technology-forward environment they had built.
GROWTH THROUGH ACQUISITIONS WITHOUT OUTSIDE CAPITAL
The second key to their rapid scaling was acquisitions. They didn't take any outside capital. They bootstrapped the whole operation, used bank debt to keep the lights on, and then systematically went after distressed transportation and warehousing businesses.
Their approach was to acquire a company, take it over, fix the problems, and bring in their own software, systems, processes, and team members. The first few acquisitions were very challenging with plenty of late nights, especially on the integration side. But after they developed their operating system for acquisitions, it got easier. For the first three years, they kept finding deals, acquiring companies, and merging them into their entity.
The formula was proprietary software, a repeatable acquisition and integration playbook, strong recruiting systems for top talent, and a relentless focus on sales and revenue growth. Josh notes that revenue solves a lot of problems, though not everything.
THE VISIONARY AND INTEGRATOR DYNAMIC
Josh and Loretta's partnership mirrors the visionary and integrator framework that operating systems like EOS and Scaling Up describe. Josh is the visionary with strengths in leadership, putting the right teams in place, and driving sales. Loretta brings the systems, processes, and operational mindset.
When they reflect on it now, working together as a newly married couple while building a rapidly scaling business with all their finances tied up in the company was quite a journey. They were drinking from the fire hose. But the combination of their complementary skill sets is what created the breakthrough after Josh's first ten years of entrepreneurial learning.
This dynamic shows up frequently on the podcast. In my conversation with Richard Manders about post-exit transitions, he described a similar partnership where he was the idea guy and his co-CEO Wayne was the one who could build the plan and execute on it. Having someone to call you out on new ideas and ask what you're going to stop doing to make room for the new thing kills about half of the visionary's ideas. And that's a good thing.
FROM STARTUP TO PE EXIT IN THREE YEARS
When they first started the business, they talked about potentially exiting one day. But Josh says he blocked that out of his mind once they were in the grind. He loved the industry, loved the team, and never really thought about selling. The conversation 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, 365-day transportation logistics business once the baby arrived.
They had also hit a capital constraint. The business was low margin, and every time they grew to the next level, it required more capital. Their accountants, lawyers, and mentors helped them realize they couldn't continue self-funding at the pace they wanted to grow.
They engaged an M&A advisor, took the business to market, and met with multiple PE firms and transportation companies. They found a well-capitalized US private equity-backed firm that also had Canadian roots in North American transportation. The deal gave them both a strategic partner and private equity backing, which was exactly what they wanted if they were going to sell their baby.
THE POST-SALE TRANSITION AND IDENTITY SHIFT
One of the most insightful parts of our conversation was Josh's description of the post-sale period. He compared it to giving a child up for adoption and then living in the same house. His deal included a two-year transition where he remained CEO, running the business separately while getting support from the larger organization.
The first two years, not much changed operationally. In fact, having the financial backing of the larger entity was a huge weight off his shoulders. He no longer had to worry about payments, managing cash flow, and all the back-end financial stress. That freed him to focus entirely on people, systems, growth, and sales.
But when the two-year deal ended, he had to make a choice. The acquirer offered him a continued role, but his other partners were gone, his wife had been out of the business for two years, and he was there by himself. The business had become more corporate. It was no longer a small company. It was part of a big entity with different needs and constraints. He didn't want to be the bottleneck, and he realized it wasn't a fit anymore.
The day he let the team know was emotional. There were tears and feelings he didn't expect. And when his email was turned off the next day, the quiet was striking. For weeks, he kept checking an inbox that was suddenly empty after years of leading over a hundred employees plus contractors.
FINDING WHAT COMES NEXT AFTER EXIT
Josh took about six months after stepping down to be a present dad with his young kids, take family trips, and figure out what was next. His wife eventually gave him a loving push. She told him she loved having him around and appreciated him being present with the kids, but it was time to get going and do something again.
He joked about selling everything and moving to a ranch to live the farming life. Loretta's response was characteristically direct. First, she pointed out that he's not very mechanical and probably couldn't handle the animals. Second, she reminded him that he loves people, loves building businesses, and loves developing leaders. That's what he should be doing.
This post-exit identity challenge is something Jodi Hume addressed in her DealQuest episode about the emotional journey behind major business decisions. Many founders don't realize that assuming an exit is always a good thing can be a mistake. The real question is what you want for yourself.
BUILDING A FAMILY OFFICE AND CONSULTING PRACTICE
After the push from Loretta, Josh set up JL Davis Enterprises as a family office using their own capital. The original plan was to use their operating system to make investments in businesses and help them scale, with Josh sitting on boards and advising.
What they discovered was that every business they invested in had the same challenges. Getting the right people in the right seats. Implementing the right technology and systems. Building a strategic plan with performance metrics and vision. They decided to launch a consulting arm that could actually go in and help businesses rather than relying on just Josh and a few team members.
The consulting business focuses on people, systems, performance, and growth. They've acquired an HR consulting firm and an executive search firm because getting the right people in the right seats is the first thing any business needs. Their value proposition is that they're operators first. They're not just HR consultants or leadership coaches. They have a team of operators who put systems together that actually work in the real world.
LESSONS FROM MINORITY INVESTING
Josh's experience with minority investments offers a valuable lesson for any post-exit entrepreneur considering where to deploy capital. His original plan was to make investments, take 10-20 percent equity, and sit on boards. What he found was that he actually likes getting his hands dirty and fixing things.
More challenging was working with founders who weren't ready for the advice. When Josh would explain what needed to happen to scale, like hiring an executive assistant to get the founder out of the weeds, some founders would realize they didn't even want to do that work anymore. They'd ask Josh to just buy them out instead.
The businesses he invests in are typically doing between one and five million in revenue. At that size, they don't have full management teams and the best systems and technology. For an investor who wants to see the business grow and get a return, misalignment with the founder can be very challenging.
As a result, JL Davis Enterprises has pivoted toward doing more 100 percent acquisitions while still selectively evaluating minority investments. The key criteria for the investments they do make include founders who still have energy to grow and scale, willingness to release control and step out of the weeds, alignment with their vision and values, and readiness to evolve.
FREEDOM THROUGH INTENTIONAL BUSINESS BUILDING
When I asked Josh about freedom, my highest value in life, his answer tied everything together. Going back to watching his grandparents build businesses, he saw that they eventually gained the freedom to choose what they wanted to do in life.
For Josh, it took fifteen years to get there. The first ten were grinding through challenges and sleepless nights. Now he and Loretta are in a position where they can make decisions that align with their family values and vision. They deliberately keep JL Davis Enterprises smaller even though PE firms and other investors want them to go bigger. They prefer the freedom to choose who they invest in and which organizations they support.
A big part of their mission is supporting the next generation. Because they don't have outside capital or PE oversight, they can make investments directly from their company to help kids at risk and rescue children from trafficking. Freedom means being able to choose how they deploy their resources without answering to anyone.
FOR MORE ON JOSH DAVIS
https://www.linkedin.com/in/scaling-with-josh-davis/
https://jldavisenterprises.com
FOR MORE ON COREY KUPFER
https://www.linkedin.com/in/coreykupfer/
https://www.coreykupfer.com/
Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.
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