Stewarding great businesses for the long term.

We are a private holding company acquiring profitable businesses in North America. We are not a fund. There is no clock, no forced exit — just patient capital and partnership with the people who built the company.

The kinds of businesses we love.

I.

$1M – $3M EBITDA

Established, profitable companies with a multi-year track record of stable cash flow.

II.

Sector agnostic

Industry doesn't matter to us — durability does. We care about the quality of the cash flows, not the category they come from.

III.

North America

Headquartered in the U.S. or Canada, with customers and operations concentrated on the continent.

IV.

Loyal customers

Recurring revenue, long-standing relationships, or a reputation that is hard to replicate.

Different by design.

Permanent capital

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.

Flexibility for sellers

Every deal is shaped around the owner's goals and the specifics of the business. We prefer partners who want to retain a stake in the next chapter.

Honest, operator-led process

Straightforward valuations, minimal contingencies, and a short list of decision makers. We move quickly, we tell you what we think, and we do what we say.

Respect for what you built

We're here as long-term stewards, not to strip for parts or chase short-term wins. Any changes we make come thoughtfully, not reflexively.

Confidential and discreet

Every conversation is held in strict confidence — always.

Built by an operator, not a financier.

David Del Balso

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 — which were acquired together by WELL Health Technologies (TSX:WELL) at a $50M enterprise value.

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.

Let's have a conversation.

Whether you're an owner considering a transition, an advisor representing one, or an intermediary with a quality business on hand — we'd welcome the introduction.

Email us directly at hello@watersideholdings.ca.