Acquiring and investing in profitable businesses in North America.
Established, profitable companies with a multi-year track record of stable cash flow.
Industry doesn't matter to us — durability does. We care about the quality of the cash flows, not the category they come from.
Headquartered in the U.S. or Canada, with operations concentrated on the continent.
Recurring revenue, long-standing relationships, or a reputation that is hard to replicate.
We are not backed by a fund with a fixed life. We have no obligation to sell in 5, 7, or 10 years — ever. Decisions are made on a decade-plus horizon, not an IRR clock.
Every deal is shaped around the situation — a clean transition for an owner, a rollover stake, or an equity check alongside a searcher. No template to force you into.
Straightforward terms, minimal contingencies, and a short list of decision makers. We move quickly, we tell you what we think, and we do what we say.
Whether we own outright or invest alongside an operator, we're here for the long haul. Any changes come thoughtfully — not reflexively.
Every conversation is held in strict confidence — always.
Founder & Principal
David is a Toronto-based founder and operator who has spent the last decade building healthcare technology companies. He founded Insig Health and Tia Health — two of Canada's earliest and largest virtual care platforms (exited at $50M EV).
Waterside Holdings is the continuation of that work — a permanent home for the kinds of small, durable businesses David has spent his career building and scaling.
10+ private investments across cybersecurity, assisted living, medical imaging, government SaaS, craft beer, and more.
Whether you're an owner considering a transition, an advisor representing one, an intermediary with a quality business on hand, or a searcher looking for capital — we'd welcome the introduction.