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Donald Miles, one of our clients is Managing Partner at Milestone Holding an investment company dedicated to identifying, acquiring, and growing small businesses.
Donald’s journey started with a common challenge: in a specific geographic area, there are only so many listed businesses and active brokers, eventually, the pipeline ran dry and when that happened, he knew he had to create his own.
With his family firmly rooted in Florida and a clear goal to stay close to home, Donald quickly realized that traditional acquisition channels, like marketplaces and brokers just weren’t going to cut it.
What came next was a carefully crafted prospecting strategy, built on tech, strategy, and most importantly, a human touch.
Right at the start of his search for a business to acquire, Donald hit a wall: the pool of publicly available opportunities in his area was small. Expanding his search to other regions was out of the question, family first!
The alternative? He tried it all… lunch with accountants, chats with financial advisors, local networking.
These connections, while valuable, were slow and uncertain. He needed a new approach, his own approach and that’s when Resquared entered the picture.
On his first call with our team, Donald instantly grasped the value: use AI to reach local business owners directly, filtered by category and geography with automated email sequences ready to launch.
It was all new territory for him. Donald had no prior experience with cold outreach and didn’t consider himself tech-savvy. But in just a few minutes, with support from our team, he was learning how to build an email sequence, add a clear call to action, and launch a targeted campaign.
He started by targeting sectors like pest control, landscaping, and roofing high-density small business areas in and around Jacksonville.
For someone with a packed schedule and no background in email marketing, that was game-changing.
Shortly after getting started with Resquared, the emails Donald was sending began generating responses, but not quite in the way he expected… Instead of replying by email, many business owners simply picked up the phone and called him directly.
“It’s interesting how quickly they dial. I don’t know if it’s the blue-collar nature, but they see the email and just call. You can even hear a lawnmower in the background;” Donald said, laughing.
That’s when a new challenge emerged: how to quickly qualify these calls.
A good number of them were micro-businesses, smaller than what he was looking for. But a few conversations stood out, like a tree service company right near his house that became one of the most promising leads in his pipeline.
As the volume increased, Donald realized he needed a fast, structured way to separate high-potential leads from mismatches and started refining his pitch and qualification process to keep things efficient. (Powerful strategy)
Around the same time, our team made a simple but powerful suggestion:
✍️ Handwritten letters.
In a digital world, a personal, handwritten note could be the spark to create a real connection. Plus, it sets you up perfectly for a follow-up like: “Hey, did you get my letter?”
Donald quickly recognized the potential of handwritten notes, though initially, he saw them as just a small supplement to his outreach.
He imagined they’d be used occasionally, maybe to follow up with the most promising leads.
But the deeper he got into Resquared’s outreach and started seeing high engagement from local business owners, the more the handwritten approach stood out as a key differentiator.
“That was always part of my plan once I kicked off proprietary outreach — which I’d say is now kind of kicked off.” Donald said
Something that started as a nice-to-have quickly became a core part of his daily rhythm. A few personal notes a day, layered on top of digital outreach, turned into a powerful way to stay memorable and move conversations forward.
As more leads came in, Donald learned the value of qualifying faster.
He began filtering based on company size, years in operation, and signs of outside investment all of which became part of his checklist.
He also began customizing his messages using Resquared’s AI tools, bringing that personal, human tone to his cold emails (something we always recommend!).
He even created tailored templates for the Maine market, where he had family ties, and quickly developed a sense for which conversations had real potential.
Today, Donald has meetings booked with real businesses that are seriously considering selling.
But more importantly, he built confidence in the process, learned how to talk to business owners across different industries, and built his own acquisition pipeline (without relying solely on brokers).
Donald’s Checklist for Building a Local Pipeline with Resquared
Here’s a step-by-step recap of what Donald did and what you can do right now with Resquared if you're stuck or unsure where to begin:
Conclusion: When Technology Meets Intentionality
Donald’s journey with Resquared proves that cold outreach doesn’t have to be a shot in the dark; it can be strategic, structured, and deeply human.
So if you, like Donald, are a searcher, start by understanding your why… and create your own strategy.
Start doing what others aren’t and build something that’s truly yours.
And let tools like Resquared be your partner along the way.
Click here to book a demo and see how we can help you write your own story.
