The thinking, written down.
The book, the guides, the planning notes and the planning tools, in one place.
20 resources
Books
The Decisions Wealth Depends On
On the insurance, structure, and succession decisions that a business family's wealth actually turns on.
Guides
The Ontario Business Owner's Guide to Insurance & Wealth Planning
A practical overview of insurance and wealth planning for owner-managed businesses in Ontario.
October 2026
Guides
The Executor's Problem: When a Business Is in the Estate
A practical guide for executors of Ontario estates that include an operating business: authority, liquidity, insurance, ownership, valuation and family fairness.
October 2026 Planning notesKey Person Insurance for Canadian Businesses
Key person insurance for Canadian businesses: sizing the exposure, the alternatives to insurance, the tax treatment, and when coverage fits.
November 2026 Planning notesFunding a Shareholder Agreement With Life Insurance
How to fund a shareholder agreement in Canada: cash, borrowing, instalments or life insurance, the buy-sell methods, the CDA, and the disability trigger.
November 2026 Planning notesCorporate-Owned Life Insurance in Canada
Corporate-owned life insurance in Canada: what it costs in pre-tax income, the capital dividend account, HoldCo or OpCo, the alternatives, and when it doesn't fit.
November 2026 Planning notesCorporate vs Personal Ownership of Life Insurance
Should the company or the owner hold the policy? How Canadian business owners decide between corporate and personal ownership of life insurance.
August 2026 Planning notesLife Insurance and the Capital Dividend Account
How a corporate life-insurance death benefit can flow to shareholders tax-free through the Capital Dividend Account, with a worked calculation and the rules.
August 2026 Planning notesBusiness Succession Planning for Ontario Business Owners
Business succession planning for Ontario owners: the transition paths, what the capital gains exemption is worth, funding a buyout, and when to start.
November 2026 Planning notesEstate Planning for Ontario Business Owners
Estate planning for Ontario business owners: the tax on private-company shares at death, ways to pay it, double taxation, probate, and dual wills.
November 2026 Planning notesHow to Equalize an Estate When One Child Inherits the Business
Equalizing an estate when one child inherits the business: sizing the gap, the alternatives to insurance, ownership of the policy, and keeping it current.
November 2026 Planning notesWhat Happens to a Business When the Owner Dies?
What happens to a private company when the owner dies: control, the shares, corporate accounts, the tax, debt and the family, and what planning changes.
August 2026 By industryInsurance & Succession Planning for Dental Practice Owners
Planning for dental practice owners in Ontario: practice debt, professional corporation structure, buy-sell funding, associate transitions, family protection and succession.
September 2026 By industryInsurance & Succession Planning for Law Firm Partners
Planning for law firm partners in Ontario: partnership obligations, partner buyouts, key-partner dependence, professional corporation considerations, continuity and succession.
September 2026 By industryInsurance & Succession Planning for Manufacturing Business Owners
Planning for manufacturing business owners in Ontario: capital tied up in equipment, key-person dependence, shareholder funding, family succession and estate liquidity.
September 2026 By industryInsurance & Succession Planning for Construction Business Owners
Planning for construction business owners in Ontario: owner dependence, debt and personal guarantees, working-capital pressure, key employees, ownership transitions and family protection.
September 2026 ToolsCoverage & Continuity
Estimate the life, disability, and critical-illness coverage that would keep your family and business whole, plus the tax on registered assets at death.
ToolsWhat Your Business Owes at Death
Estimate the income tax triggered on your private-company shares at death, the effect of the capital gains exemption, and how corporate insurance funds it.
ToolsEstate Equalization
Model the estate-equalization gap when one child inherits the business and others receive liquid assets, including tax at death and insurance funding.
ToolsShareholder Funding Gap
Estimate the capital required to fund a shareholder buyout and compare it with insurance, corporate liquidity and other funding already available. Built for Ontario business owners.
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Sheldrake Group Inc. O/A Sheldrake Group is a licensed life insurance agency in Ontario. Information on this page is general in nature and is not tax, legal or insurance advice.