I’m on my third attempt at buying a small business, and I wanted to share the journey so far for accountability, and to learn from others who are a few steps ahead of me. In 2019, I started by trying to acquire a nursing home in Canada. I spent months learning the space, talking to operators, and working with lenders. Then COVID hit. Overnight, long‑term care went from “stable and defensive” to “radioactive” in the eyes of most banks. Financing effectively dried up, especially for a first‑time buyer, and that deal died on the vine. I pivoted to HVAC. That turned into an amazing education: I learned how to source deals, talk to owners, and underwrite blue‑collar service businesses. I got a front‑row seat to what makes a good service business tick (maintenance contracts, techs, trucks, dispatch, margins, seasonality). But I also made mistakes. I stretched myself financially, had personal issues going on at the same time, and eventually ran out of runway. I chose to move back in with my parents to reset, cut my expenses, and rebuild. That was humbling. Fast‑forward toredactedAfter taking time to reset, I’ve decided that “third time’s the charm”. I’m back in the hunt but this time with more scars, more humility, and a much clearer thesis. I’m now looking at acquiring a bookkeeping / accounting‑focused firm in Canada/USA (starting with Québec). A few important points: I’m not a CPA. My role is to be the owner‑operator and builder, not the person doing the technical accounting work. I plan to build a strong technical leadership team (experienced CPA(s) and senior staff) to lead the technical work, quality, and compliance, while I focus on clients, people, systems, and growth. Why this sector? It’s boring, essential, and recurring monthly and annual recurring revenue from small businesses. It’s fragmented, with lots of small firms and aging owners who are thinking about succession. With the right team, it can run at strong margins and be a great platform for a long‑term hold and future add‑on acquisitions. I’d really appreciate advice from people who’ve actually done this, especially: Non‑CPAs who have bought and grown bookkeeping or accounting firms CPAs / firm owners in Canada or Québec who’ve sold to, partnered with, or worked under a non‑CPA owner Lenders or brokers who have financed these types of deals Specific questions: As a non‑CPA, what are the biggest blind spots I should be aware of when evaluating a firm? What would make you comfortable selling your firm to a non‑CPA buyer with a strong CPA/technical team? Are there any regulatory or ownership nuances in Québec I should be careful about if the firm holds itself out as a CPA practice? I know this path isn’t easy. I’ve already failed twice. But I’m still here, still hungry, and I believe this is the right time for me to take another swing with more discipline and a better‑designed team. If you’re open to it, I’d love to connect with people who: Own or have owned bookkeeping/accounting firms Are CPAs in Québec or elsewhere in Canada Or have tried (and perhaps failed!) at buying a business before eventually getting a deal done DMs are open, and thoughtful comments are very welcome.