The Succession
Gap

Small and medium-sized businesses are the actual engine of the North American economy. Not as a rhetorical flourish — as a measurable reality. In Canada, SMEs represent 98% of all employer businesses and employ nearly 45% of the private sector workforce. In the United States, the figure is 99.9% of all firms, generating 44% of national GDP. These businesses are not a segment of the economy. At the level where most people actually work, earn, and build their lives, they are the economy.

And right now, at a scale and pace with no historical precedent, the people who built them are stepping back.

The Baby Boomer generation owns a disproportionate share of North American small businesses — enterprises built over thirty or forty years, through recessions and recoveries, through the long accumulation of customer trust, supplier relationships, and operational knowledge that cannot be purchased or replicated quickly. Those owners are now in their sixties and seventies. Many are ready to exit. And in too many cases, there is no one positioned to take over.

These are not abstract statistics. They are the trades business that trained thirty apprentices over two decades. The professional services firm whose relationships took a generation to build. The family enterprise that anchored its community's economic life. The Indigenous-owned company that demonstrated, in practice, what community-controlled development looks like. When businesses like these close not because they failed but because there was no one ready to carry them forward, the loss is not simply financial. It is institutional. The knowledge, the relationships, the community infrastructure — gone.

The need is real.
The market hasn't answered it.

The conventional market response to business succession is straightforward: a broker lists the business, a buyer finds it, a deal closes. For larger, professionally managed businesses with audited financials and documented operations, this works reasonably well. The infrastructure — advisors, lawyers, institutional buyers — is built for transactions of that scale and legibility.

Most SMEs are not that business. Most SMEs are owner-operated, relationship-dependent, and functionally opaque to the buyers who have the capital to acquire them. Their value lives partly in the owner's head — in decades of supplier trust, in customer relationships built through consistent reliability, in operational knowledge that was never written down because the owner never needed it to be. To a conventional acquirer, this looks like risk. It is, in fact, the asset.

The result is a structural gap. Not a shortage of businesses worth owning. A shortage of new owners prepared to own them — and a shortage of the support infrastructure required to make those transitions succeed. New operators need to be found and developed, not just located. Ownership structures need to be designed that make acquisition genuinely accessible. The businesses themselves need preparation: their knowledge documented, their operations stabilized, their owner-dependency reduced before the handoff takes place.

This gap will not close on its own. The market that exists to serve large M&A transactions has neither the incentive nor the structure to serve the hundreds of thousands of small businesses where the need is most acute. Something different is required — and the window for building it is not indefinite.

Technology is the competitive
advantage most SMEs never had access to.

There is a second dimension to this challenge that rarely appears in the same conversation as ownership succession — and it may be the more consequential one for the long-term durability of these businesses under new ownership.

The majority of SMEs are running on infrastructure built a generation ago. Processes that have never been automated. Customer data that lives in spreadsheets or in the owner's memory. Workflows that accumulated organically and have never been examined systematically. Communications and scheduling that require the owner's personal attention for things that could be handled by well-designed systems. The business is not underperforming because its people are incapable. It is underperforming because the technology available to larger organizations — AI systems, operational automation, custom software built for specific workflows — has never been brought to bear on it.

This is partly a cost problem: enterprise-grade technology has historically been priced for enterprises. It is also an attention problem. SME owners are operators first. The bandwidth required to evaluate, procure, and implement technology is bandwidth they rarely have, and the off-the-shelf solutions available to them rarely fit the specificity of how their businesses actually operate.

The challenge has always been access — both to the technology itself and to people who understand how to build and deploy it in ways that fit how these businesses actually work. Generic software forces a business to adapt to the tool. The right approach is the reverse: understand the business first, then build the tool around it. That requires a combination of technical capability and genuine operational understanding that is not common and not easily replicated.

This is work worth doing.

I want to be direct about why I am in this space.

The SME succession wave is one of the defining economic events of this decade in North America. The scale of it — the number of businesses, the employment they represent, the communities that depend on them, the wealth embedded in them — means that how it unfolds will shape the economic landscape for the generation coming behind it. If these transitions happen well, wealth is preserved, employment continues, and communities retain their economic anchors. If they don't, the losses are structural and largely permanent.

I have been building in this space because I believe the gap is closable — and because the work of closing it is genuinely consequential. Through DeepCurrent Systems, my team builds and deploys AI agents, operational automations, and bespoke software directly into SME environments. We custom-build to the business, not the other way around. The technology we bring is designed to make the people inside these companies more capable and more invested — and where it makes sense, that investment takes the form of profit sharing tied to the performance improvements the technology enables. When the business does better, the team that made it better participates in that outcome.

I am also building a portfolio — acquiring and partnering on SME businesses alongside operators who are serious about long-horizon stewardship. I work with teams across these deals, not just with owners. The transitions I am involved in are designed to keep the businesses alive, keep the people employed, and build on what was created rather than extract from it.