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that can mean funding a shareholder agreement, protecting the company from the loss of a key person, restructuring outdated insurance, or preparing for an eventual transfer of ownership.
Sheldrake works with business owners and their families to make sure the plan around what they have built is as considered as the business itself.
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. 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, Sheldrake reviews the ownership, insurance, and estate arrangements already in place, alongside the accountant and lawyer who know the situation, before any solution is on the table.
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.
Zachary Sikorski CHS · EPC
Before founding Sheldrake Group, Zachary spent his entire career in financial services, beginning in 2008 and most recently serving as a District Vice President at Sun Life, supporting independent advisory practices across Ontario and British Columbia.
It was an unusual vantage point. Rather than building a single book of clients, he watched hundreds of planning conversations unfold, involving business owners, professionals, and families, close enough each time to see how hard it can be to connect otherwise sound investment, insurance, tax, and estate advice into one coordinated picture.
Sheldrake Group is built on the judgment that experience produced.
Away from the work, most of Zachary's decisions are made with his wife and two children in mind, a reminder that behind every plan is a family, not a balance sheet.
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?
Sized to bring each heir to an equal share, without selling the business.
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.
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, not the paperwork, is the hard part.
Read the guide →
Business Owner Planning Notes
Short, practical notes on succession, shareholder agreements, corporate insurance, estate planning and family wealth.
Explore the library →Most of our work begins with a conversation.
Sheldrake takes on a limited number of relationships, most often through an existing client or professional advisor. If the work described here reflects a decision you are facing, you are welcome to begin the conversation.
Begin a conversation