Insights

Understand the work. Then improve it.

A weekly pressure-test of one real listing, practical guides on buying and improving a small business, and clear, practical notes on where AI and automation actually pay off.

Deals of the WeekBuying and improvingAI and automationThe working library

Deals of the Week

A new real Canadian listing every Tuesday. Each edition tests the disclosed numbers, names the biggest risk and asks one question that decides the deal. Listing claims are not verified.
No. 007 · October 13, 2026Masonry contractorWinnipeg, MB · $1.29M askWhich earnings year are you buying?No. 006 · October 6, 2026Rural vet clinicSaskatchewan · $895K askWho treats the animals after the seller leaves?No. 005 · September 29, 2026HVAC maintenanceOntario · $750K askWill the customers come back?No. 004 · September 22, 2026Trailer manufacturerSouthern Ontario · $1.16M askWhich jobs actually make money?No. 003 · September 15, 2026Staffing companyCalgary · $5.25M askWho funds Friday’s payroll?No. 002 · September 8, 2026Coding platformCanada · $2.9M askWhy do subscribers renew?No. 001 · September 1, 2026Bookkeeping practiceGTA · $500K askWho does the owner’s job?

Buying and improving a business

Numbers first. Feelings after the lender’s call.
Deal economics · 5 min read

How to Normalize SDE When Buying a Canadian Small Business

Strip out the owner’s one-offs and personal costs, then charge the business for the person you will have to hire.

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Due diligence · 5 min read

Small-Business Acquisition Due Diligence: A Practical Checklist

What to ask for, what to check against the bank statements, and which answers should slow the deal down.

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Post-close · 5 min read

What to Automate During the First 100 Days After an Acquisition

Fix the handover first, then pick the repetitive work that is safe to automate once you own the place.

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Affordability · 4 min read

How Much Business Can You Afford in Canada?

Work backwards from the cash you have and the payments you can carry to a realistic purchase price.

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Earnings · 3 min read

SDE vs EBITDA for Canadian Business Buyers

Two ways of measuring earnings, and when each one is the right yardstick for the size of deal you are looking at.

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Deal screen · 3 min read

How to Analyze a Business Listing in 10 Minutes

A quick first pass: what to read, what to recompute and when to walk away before you call the broker.

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Debt capacity · 4 min read

DSCR for Canadian Small-Business Buyers

How lenders judge whether a business can cover its loan payments, and how to check yours before they do.

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AI, automation and operating systems

Fix the process first. Then automate it.
Opportunity discovery · 6 min read

How to Find High-ROI AI Automation Opportunities in a Small Business

Where the repeated, rules-based work hides in a small business, and how to size it before you spend anything.

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Pricing · 5 min read

What Does an AI Consultant Cost in Canada?

What different kinds of AI help tend to cost, what drives the price and what to ask for in a quote.

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Capacity · 5 min read

Seven Business Processes Worth Automating Before Hiring Another Employee

Seven candidates to try first when the team is stretched and the next hire is not obviously the answer.

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Readiness · 5 min read

A Practical AI Readiness Checklist for Small Businesses

A plain checklist for whether your data, process and people are ready for AI, or need tidying first.

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Systems · 4 min read

CRM vs Spreadsheet: When a Small Business Should Upgrade

Signs the spreadsheet has stopped working, and what a right-sized CRM looks like when it has.

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The rest of the working library

Library

Free tools

Business Calculator, CRM and project-tracker builds you can use before you pay for software.

Open the tools →
Library

Acquisition Playbook

Compare salary, startup and ownership, and see how cash, financing and operations fit together.

Open the playbook →
Library

Deal Calculator

Normalize earnings, add the costs you really need and see what is left after debt.

Open the calculator →
Library

Glossary

SDE, add-backs, working capital and the rest of the buyer’s vocabulary, explained clearly.

Open the glossary →
Library

About AndChill

Who is behind it, what has shipped, and how to start a conversation.

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