Growth Through Acquisition: A Real-World Playbook for Founders & Operators

CEO and co-founder of one of Canada’s fastest-growing logistics companies. We scaled through a roll-up strategy—acquiring small, underperforming transportation businesses and scaling them by recruiting high-performance teams, developing leaders, building systems, and creating our award-winning logistics software. In 2019, we exited to one of the largest transportation companies in North America, backed by a multi-billion-dollar U.S. private equity firm.

Since then, I’ve continued acquiring companies across multiple industries through our family office—using the same systems, playbooks, and operating strategies we built from the ground up.

Through our business consulting firm, we help companies scale through people, systems, and technology. We advise some of the largest organizations in North America on people strategy—but my passion is helping small to mid-sized business owners grow with clarity, grit, and proven systems.

Starting from scratch is risky. Most businesses fail before they ever get traction.

That’s why buying a business is one of the most overlooked—and smartest—paths for modern entrepreneurs.

We’re in the middle of the greatest wealth transfer in history.

Millions of baby boomers are retiring—many of them own profitable small businesses with no succession plan. These companies aren’t flashy, but they’ve stood the test of time, with loyal customers and steady cash flow.

Most lack strong systems, modern technology, solid sales processes, leadership depth, or a clear growth strategy. That’s where the opportunity lies—for the right operator to step in, modernize, and scale.

You don’t need to start from scratch to build something great. You can acquire a business that’s already working—and grow it faster, smarter, and with less risk.

1. How to Find Off-Market Deals

Pick Your Industry. Start by picking an industry that genuinely interests you. —Then do research so that you understand the customer, product, problem and competition.
Reach out directly. Look up owners in a retirement age range from your selected industry, and reach out through emails, personalized LinkedIn messages or cold calls.
- Be human. Be direct. Build trust.
Build Your Network. The best deals are never on BizBuySell. Network with M&A advisors, accountants, bookkeepers, business lawyers, and financial advisors—they often know when a business owner is ready to step back.
Get Warm Intros. Attend local business events, owner meetups, and industry groups to get warm intros and build trust.
Hunt for Hidden Gems. Look for businesses that don’t have a flashy online presence but have been around 10+ years with steady revenue.
Spot the Seller’s Signals. Signs an owner may be ready to sell:
- talk of ‘slowing down’ or ‘retirement’
- children not working in the business
- struggling to keep up with technology
- minimal interest in scaling
- people problems

2. Red Flags to Watch For

Buying a Job vs. a Company. In smaller deals the owner (most likely) is the business —handling sales, ops, and customer relationships—be prepared that you might be buying a job, not a company. Make a clear transition plan to take over those responsibilities.
Ride Along First. For first‑time buyers, take on those owner tasks yourself initially to truly understand how the business runs.
Red Flags. Watch for:
- unexplained revenue changes
- messy financials
- misaligned values
- negative culture
- key staff that have recently left
Leadership & Systems Gaps. No leadership team, outdated systems, or a culture of dependency —be prepared it will be a heavy lift post‑close.
Opportunity in Distress. Some of our highest ROI deals came from distressed businesses — I would only do this when you have the right experience and team to handle the chaos. But when done right — it can have tremendous upside.

Protect Yourself—Then Profit.

Spot red flags early.
Build your transition plan.
Turn risk into your competitive advantage.

“Watch the red flags—what you ignore can cost you most.”

-Josh Davis

3. Structuring the Deal

Structure is everything It is possible to structure deals with little to no money down using a combination of:

- - bank financing,
  - seller notes,
  - profit shares, and
  - performance‑based earnouts.
Seller Notes & Earnouts.Use seller financing – defer part of the purchase price via seller notes and include earnouts to bridge valuation gaps.This fair approach protects the buyer while helping the seller secure their target price.
Performance‑ Based Earnouts. Tie a portion of purchase price to future performance —align incentives and reduce upfront risk.
Protect Yourself Day One. Prioritize acquisitions you can comfortably finance without taking on excessive leverage. And structure debt at manageable levels.
Watch for Overpayment. Most first‑time buyers overpay and underestimate the owner’s involvement.
Owner Transition Plan. Implement a robust transition plan to assume the owner’s responsibilities.
- “Remember an owner selling a business and still working in it, could feel like giving a child up for adoption but still living in the same house.” -Josh Davis

Structure Win-Win Solutions. The highest chance of getting the deal across the finish line is making sure the offer is as close to a win-win as possible for both the seller and the buyer.

Point 1

Don’t make major changes in the first 3 months. Shadow the team, document everything, and learn the operation from the inside out.

Point 2

Don’t break what’s working. Modernize carefully—keep the customer trust, just upgrade the backend.

Point 3

Know who the key team members are. Build trust, invest in the relationship, and get their buy-in early. When they believe in the vision, they’ll help champion it across the business.

Point 4

Start by defining clear roles and responsibilities. Set measurable KPIs and build simple scorecards for each role. Tie compensation to company growth wherever possible. Create a culture where the team takes full ownership and is held accountable for results.

Point 5

Make sure you have the right people in the right seats. That’s the key to scaling. The wrong team member—or wrong hire—will slow you down, drain your energy, and cost you more than just time. Skills matter, but alignment with your values, culture, and pace is non-negotiable.

Point 6

Often, one or two A-players can unlock major efficiency.

Point 7

Give everyone a fair opportunity to get on the bus—but understand that not everyone will. Some people resist change, slow down progress, or create friction. If they won’t adapt, they can’t stay. You can’t scale with toxic attitudes or passengers who don’t want to move forward.

Be careful: Most sellers won’t want to stick around long after the deal closes—especially under a new owner. For them, it can feel like giving up a child for adoption and still living in the same house. Be careful here. Lead with empathy, but plan for a short transition with clear boundaries and expectations.

Founders looking to scale fast through acquisitions and roll-ups

Operators ready to take over and grow a business that’s already working

Leaders focused on building long-term impact and legacy through small business ownership

Ready to Go Further?

This playbook is just the starting point. If you’re serious about growing through acquisition and want support finding deals, structuring smart terms, and scaling post-close—let’s talk.

We work with a select group of operators inside our Growth Through Acquisition coaching group—a community built for founders who want to acquire and scale with confidence.

Let’s build something that lasts.

Email me at info@jldavisenterprises.com

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