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The Business I’d Build If I Started Over Today
by Bill Canady in Strategy
April 23, 2026
If I were starting over today — no capital, no contacts, no books — I’d build a middle market services business. Here’s why, and here’s how I’d do it.
Why services, not products
Product businesses are capital-intensive and hit margin compression fast. A well-run services business with recurring revenue and proprietary IP can hit 20%+ EBITDA margins and sell at strong multiples. The barrier to entry is your expertise. That’s a moat you can build in a year.
How I’d structure it
Narrow vertical. Specific buyer persona. One core offering that solves an expensive problem. Productized, so it scales. Recurring revenue model. Sales team within 18 months. Exit-ready financials from day one.
What I’d refuse to do
Take on customers outside the ICP. Build custom for anyone. Compete on price. Hire generalists. Raise money before I had proof of repeatable revenue. Every one of these is how middle market services companies die.
The 80/20 principle applied from day one
In a new business, the 80/20 rule is the difference between a decade of grinding and a company you can sell in five years. Find the 20% of the market where the economics work. Everything else is a distraction you can’t afford.
Why I’m telling you this
Because most middle market founders built their businesses the hard way — by saying yes to everything. You can re-architect your existing business using these same principles. That’s most of what I coach on.
Ready for a direct conversation about your business?
Bill Canady takes a limited number of strategy coaching calls each month with middle market CEOs, founders, and owners who want a direct read on where their company stands and what to do next. No pitch. No fluff. One honest conversation about growth, profitability, and exit readiness. Book your strategy coaching call at billcanady.com.
