Business Sale
Episodes on Business Sale
GuestIs Your Accountant Actually Helping You?
How financial planning, tax strategy, and the right advisory team come together to build long-term wealth.
- Business Owners
- Tax Planning
- Business Sale
EpisodeYour Business Partner Can Take Everything
How business partnerships that start with shared vision and ownership can unravel over time — often due to shareholder agreements, misaligned incentives, and structural decisions made at the beginning
- Shareholder Agreement
- Business Owners
- Business Sale
SoloHe Lost $5M To The CRA Because He Trusted His Accountant
How the wrong advisors can create hidden tax risks, derail due diligence, and even kill a business sale – costing owners millions before the deal ever closes.
- Business Sale
- Business Valuation
- CRA Audit
SoloCRA Trap Of Excess Corporate Cash
How poor tax planning can turn a $3 million business sale into an $800,000 tax problem – and why the biggest deal-saving strategies happen years before a buyer every appears.
- Business Sale
- LCGE
- Corporate Reorganization
SoloCRA Penalizes You $334K For Having Cash
How excess cash, investments, and intercompany loans inside your corporation can quietly disqualify you from the Lifetime Capital Gains Exemption – costing business owners hundreds of thousands in lost tax savings.
- LCGE
- Business Sale
- Corporate Tax
EpisodeHow to Make Your Company Sale-Ready — Structuring Before the Buyer Shows Up
What it really means to be sale-ready – not just operationally, but structurally and tax-efficiently positioned long before a business exit ever happens.
- Business Sale
- Sale-Readiness
- Business Valuation
Posts on Business Sale
Should You Put Assets In Your Kids' Names? Why Wealthy Canadian Families Never Do
Wealthy Canadian families almost never put assets in their kids' names. Here's why, how a family trust works instead, and the timing decision worth $1.3 million.
The Tax Rule That Punishes Canadians for Helping Family — And What You Can Do About It
New CRA bare trust filing catches family bank accounts, joint titles, crypto held for relatives—$50K penalties even if you owe $0 tax. Bill C-15 passed House, Senate next. Sign petition + download checklist before 2026 tax year.
3 CRA Powers Coming in 2026 That Every Canadian Needs to Know
The CRA's new 2026 audit powers — compelled sworn testimony with no transcript, $50/day penalties without a court, and reassessment clocks frozen indefinitely. Here are the three every Canadian needs to understand.
One Mistake Killed His $5M Deal — Why the Wrong Team Destroys Business Sales
Selling your business? One wrong hire and hidden tax traps can kill the deal. Why regular accountants fail at business-exit tax planning — and how to build the deal team that protects your sale.
CRA’s 5 Most Dangerous Weeks: What TEBA Means for Your Next Audit
What is TEBA, and why does it make February–March the most dangerous weeks for a CRA audit? How the CRA's March 31 year-end drives aggressive reassessments — and a 3-phase plan to protect yourself.
$800K Tax Bill That Should’ve Been $0 — The 5 Mistakes That Cost This Business Owner Everything
Discover the 5 critical errors that turned a $0 tax bill into an $800K disaster for a business owner. Learn how to protect your company from CRA reassessments, audits, and massive penalties.
Visual Guides on Business Sale
The Airbnb Tax Nobody Knows About
You put your home on Airbnb. The bookings are strong. The income is rolling in. But according to CRA, your home may no longer be a home. It may now be treated as commercial property – like a hotel. And when you sell, you could owe $150,000 in unexpected tax. Here is the breakdown: 🏠 How Airbnb can trigger CRA's "change of use" rules ⚖️ The 2024 court case where CRA successfully applied HST on sale 💰 How one homeowner could owe roughly $150,000 in HST alone 🚫 Why stopping Airbnb does not fix it — every exit triggers the same tax 📋 What you should do right now if you host on Airbnb These rules were written 30+ years ago for hotels. Nobody in government has updated them for Airbnb. And Airbnb is not warning you.
Why The Wealthy Never Gift Their Kids Anything
The wealthiest families in Canada almost never put anything in their kids' names. Not the company. Not the property. Not the investments. It isn't because they don't trust their kids. It's because a gift is the one financial move you can never take back. Swipe for what they do instead, and the $1.3 million difference it made for one family.
Resources on Business Sale
The Family Trust Decision Guide
Use this guide to determine whether a family trust fits your situations and learn when it can help protect wealth, reduce tax, and preserve flexibility.
Deal Team Checklist
Build the right team 12–24 months before you sell. Defines the four roles — existing accountant, deal-experienced tax advisor, M&A lawyer, broker / investment banker — what each is responsible for, and the questions to ask before signing engagement letters.
Does Your Company Qualify for the $1.25M LCGE?
Three-test breakdown of the LCGE: QSBC status, 24-month rule, and 50%/90% asset tests — a $334K+ tax-saving tool many owners think they qualify for but don't.
The Must-Do Checklist Before Any Sale, Restructure, or Freeze
Use this before speaking to your accountant or lawyer. Covers 6 key tax triggers—LCGE, safe income, shareholder loans, ownership, reorganizations & cross-border risk.
Pre-Sale Tax Checklist
The tax planning steps every business owner should complete 1–3 years before going to market — base-case modelling, optimization gap, structure cleanup, and the strategies that turn an $800K tax bill into something materially smaller. Same workflow used internally with private clients.