Business Sale
Business Sale — All content on The Advisors Table.
Episodes
SoloFamily Trusts Explained: Why The Wealthy Never Gift Their Kids Anything
Why wealthy Canadian families never put assets in their kids' names, how a family trust actually works, and the timing decision worth $1.3 million.
- RRSP
- Tax Benefits
- Business Sale
SoloThe Airbnb Tax Nobody Knows About
How Airbnb income can quietly transform your home into a taxable commercial property – triggering unexpected HST, loss of principal residence treatment, and massive tax exposure on sale.
- Business Owners
- Business Sale
- Legal Perspective
EpisodeCanada Wants $500K to Let You Leave | Majority, Exit Tax, Bare Trusts
How majority government power, headline tax cuts, and hidden compliance rules can quietly cost Canadians far more than they realize.
- Business Sale
- Trust Planning
- Family Trust
GuestIs Your Accountant Actually Helping You?
How financial planning, tax strategy, and the right advisory team come together to build long-term wealth.
- Estate Planning
- Business Sale
- Corporate Reorganization
GuestThe IRS And CRA Double Tax Trap For Canadians
What no one tells you about the million-dollar tax traps, IRS penalties, and the entity mismatch that can bankrupt your investment.
- Estate Planning
- Business Sale
- Corporate Reorganization
EpisodeImmigration Tax Traps That Cost Thousands
What no one tells you about foreign assets, worldwide income, and the CRA penalties that can wipe out your savings.
- Estate Planning
- Business Sale
- Corporate Reorganization
GuestMost Wills Fail. Here's Why
Why most wills fail in Canada – not due to drafting, but because they become outdated, clash with laws, and fail to reflect real family and asset changes over time and across jurisdictions
- Estate Planning
- Business Sale
- Corporate Reorganization
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
- Estate Planning
- Business Sale
- Corporate Reorganization
EpisodeShould Your Money Live in a Corporation or Personally?
Most people focus on what to invest in – but where you invest matters far more, shaping taxes, growth, and long-term after-tax wealth over time.
- Estate Planning
- Business Sale
- Corporate Reorganization
EpisodeHelping Your Kids? CRA Takes a Cut
Why “gifts” can create tax exposure for parents.
- Estate Planning
- Business Sale
- Corporate Reorganization
EpisodeBeing An Executor Can Cost You Personally
How choosing an executor is far more than an administrative decision – and how personal liability, CRA reassessments, and estate risks can last years.
- Estate Planning
- Business Sale
- Corporate Reorganization
EpisodeCRA Bill That Destroys Wealth After Divorce
Why family law, tax rules, and poor documentation can turn parental help into an unintended wealth transfer.
- Estate Planning
- Business Sale
- Corporate Reorganization
EpisodeThe Audit Machine – What 53,000 CRA Employees Are Actually Doing
How CRA's growing audit machine uses data, automation, and aggressive enforcement tactics to identify risks, escalate reviews, and collect billions beyond regular tax filings.
- Estate Planning
- Business Sale
- Corporate Reorganization
EpisodeLeaving Canada? Here’s What The CRA Wants You To Know
What tax residency, departure tax, and cutting ties really mean when you move abroad.
- Estate Planning
- Business Sale
- Corporate Reorganization
EpisodeThe $10M Tax Bill When A Business Owner Dies
How one founder built a $50M company but left his family exposed to over $10 million in tax, probate delays, and succession chaos due to missing estate planning.
- Estate Planning
- Business Sale
- Corporate Reorganization
EpisodeCRA Voluntary Disclosure Program 2025 Explained | What's Changed & What It Means
How Canada’s updated Voluntary Disclosure Program changes the way unreported income, foreign assets, and tax filings are treated — and who still qualifies for relief under the new CRA rules.
- Estate Planning
- Business Sale
- Corporate Reorganization
EpisodeWe Can’t Build Affordable Housing While Taxing It Like A Luxury Tax
How Canada’s tax system can make housing less affordable long before construction begins — by shaping costs, incentives, and development decisions from the ground up.
- Business Sale
- Succession Planning
- Real Estate
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
- CRA Audit
- CRA Powers
Posts
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.
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.
$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
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.