The hardest problems success creates aren’t investment problems. They’re decision problems.
Success creates choices. It also creates complexity: in how a business is structured, how wealth transfers, and how a family is protected when circumstances change.
In practical terms, that can mean funding a shareholder agreement, protecting the company from the loss of a key person, restructuring outdated insurance, or preparing for an eventual transfer of ownership.
The work is done alongside the accountant and the lawyer already in place, not in place of them. Most owners have capable advisors. What they rarely have is someone accountable for how the pieces fit together, and that gap is what quietly costs families the most.
The planning behind the protection.
Business continuity and key-person risk
Protecting the company when its value depends heavily on one person or relationship.
Shareholder and buy-sell funding
Making sure ownership can transfer as intended following death, disability or departure.
Corporate-owned insurance
Structuring coverage around the corporation, estate and long-term objectives.
Group benefits and key-employee retention
Building the benefit and protection structures that hold a leadership team together.
Estate liquidity and family equalization
Creating fairness when one child inherits the business and others do not.
Succession and wealth transfer
Preparing ownership and family decisions before a transition becomes urgent.
A conversation, not a pitch.
A relationship usually begins with a conversation about the business, the family, and the decision that has become difficult to resolve.
Where it makes sense to go further, an engagement typically includes a review of the ownership, insurance, and estate arrangements already in place, identification of any funding gaps, recommendations developed in consultation with your accountant and lawyer, and implementation once everyone agrees on the plan.
See how this plays out in an illustrative case →
The first meeting costs nothing and commits you to nothing. Its only purpose is to understand the problem clearly enough to know whether there is one worth solving.
See the problem before choosing the solution.
Coverage & Continuity
How much capital would the family, the business, and the estate each actually require?
Three obligations, three different decisions — separated so each can be sized on its own terms.
Explore the analysis →What Your Business Owes at Death
How much tax is quietly embedded in the shares of a private company?
The exemption is valuable only if the shares continue to qualify.
The largest bill a family may ever receive can arrive the day an owner dies. The first step is knowing what it could be.
Explore the analysis →Estate Equalization
When one child inherits the business, what makes the others whole?
Each heir receives approximately $3M. The business stays whole. Assumes the successor's share is the business itself and the liquid assets are divided among the other heirs.
Fair and equal aren't the same thing. This sizes the gap between them — and the insurance that closes it.
Explore the analysis →Shareholder Funding Gap
Is there enough capital to actually fund a shareholder buyout?
The agreement determines what should happen. The funding determines whether it can.
A funding gap is not automatically an insurance need — but it is always a question worth answering before a triggering event arrives.
Explore the analysis →Figures shown are illustrative examples, not estimates for any individual, and do not constitute tax, legal, or financial advice.
Ask a planning question.
Describe the situation you are trying to work through. Ask Sheldrake will answer first, then ask one question at a time where more detail would help.
Zachary Sikorski CHS · EPC
Before founding Sheldrake Group, Zachary spent his career in financial services, beginning in 2008 and most recently as a District Vice President at Sun Life, working alongside independent advisory practices across Ontario and British Columbia. Rather than building a single book of clients, he watched hundreds of planning conversations unfold, close enough each time to see where sound investment, insurance, tax, and estate advice failed to connect.
That experience informs what he looks for in every engagement: shareholder agreements without the funding to honour them, coverage that hasn't kept pace with the business, and decisions that were never coordinated with the rest of the picture.
Away from work, Zachary spends time with his wife and two children, often at the hockey rink, at dance, or on the golf course.
Steven Bacher CHS
Steven is the principal of Bacher Insurance Agency Ltd., an independent brokerage that has advised individuals, families, and corporations since 1990, building many long-standing client relationships along the way. He works alongside Zachary on wealth and insurance planning, bringing decades of practical experience to every engagement.
Tom Lowden BA, GBA, PFA, CFP
Tom is the principal of Lowdenclear Wealth Management Inc. and a Certified Financial Planner whose practice centres on group benefits. He holds the Group Benefits Associate (GBA) designation from Dalhousie University. At Sheldrake, Tom is the Strategic Partner for group benefits. When a client needs a plan designed, reviewed, or restructured, he's the specialist who does that work.
The thinking, written down.
The Decisions Wealth Depends On
The decisions that quietly determine whether wealth lasts through a generation — and how owners can make them deliberately, before they become urgent.
Read more →
The Ontario Business Owner's Guide to Insurance & Wealth Planning
A practical reference on structure, protection, and succession for owner-managed businesses in Ontario.
Read the guide →
The Executor's Problem: When a Business Is in the Estate
A practical map for anyone administering the estate of an Ontario business owner, where the company needs attention before the paperwork is finished.
Read the guide →
Business Owner Planning Notes
Short, practical notes on succession, shareholder agreements, corporate insurance, estate planning and family wealth.
Explore the library →
Planning by Industry
Insurance, succession and continuity decisions for dental practice owners, law firm partners, manufacturers and construction businesses.
Explore by industry →Most of our work begins with a conversation.
Most relationships start with an introduction from an existing client or a professional advisor. Business owners and advisors are equally welcome to reach out directly. If the work described here reflects a decision you are facing, you are welcome to begin the conversation.
Begin a conversation