The hardest problems success creates aren’t investment problems. They’re decision problems.

Insurance planning for owner-managed businesses and the families behind them.

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that can mean funding a shareholder agreement, protecting the company from the loss of a key person, restructuring outdated insurance, or preparing for an eventual transfer of ownership.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 can be missing is someone focused on how the pieces fit together. That is where Sheldrake concentrates its attention.

Where to start
What happens to the company, and to the family, if an owner can’t continue?

Shareholder funding, key people, corporate-owned insurance, succession and estate liquidity.

Business owner planning →
What is actually driving your group benefits renewal?

A written review of the renewal, the plan design and how the plan is funded, with the trade-offs laid out before anything changes.

Group benefits →
Has a client’s plan reached the question of whether insurance belongs in it?

For accountants and lawyers coordinating ownership, estate or succession planning for a client.

For professional advisors →

How we work →

Planning Tools

See the problem before choosing the solution.

01 / Coverage

Coverage & Continuity

How much capital would the family, the business, and the estate each actually require?

Illustrative capital exposure
Family$1.52M
Business$1.1M
Estate$276K
Total capital exposure $2.89M

Three obligations, three different decisions, separated so each can be sized on its own terms.

Explore the analysis →
02 / Estate

What Your Business Owes at Death

How much tax is quietly embedded in the shares of a private company?

Illustrative tax exposure
Business value$5.0M
Adjusted cost base$100K
Capital gain$4.9M
Estimated first-layer tax $1.31M ~$970K if QSBC exemption available

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 →
03 / Equalization

Estate Equalization

When one child inherits the business, what makes the others whole?

Illustrative equalization
Business to successor$3.0M
Other heirs×2
Liquid, after tax at death$450K
Life insurance to equalize ~$6.0M

Each heir receives approximately $3.15M. The business stays whole. Assumes a $900K liquid estate, $450K of tax at death, and the remainder divided equally among all three heirs.

Fair and equal aren't the same thing. This sizes the gap between them, and the insurance that closes it.

Explore the analysis →
04 / Shareholders

Shareholder Funding Gap

Is there enough capital to actually fund a shareholder buyout?

Illustrative funding gap
Purchase obligation$4.35M
Funding identified$3.0M
Unfunded amount $1.35M 69% funded

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.

Who you work with

Zachary Sikorski, founder of Sheldrake Group

Zachary Sikorski CHS · EPC · CEA

Principal

Steven Bacher, Practice Partner at Sheldrake Group

Steven Bacher CHS

Practice Partner

Tom Lowden, Group Benefits Strategic Partner at Sheldrake Group

Tom Lowden BA, GBA, PFA, CFP

Group Benefits, Strategic Partner

Library

The book, the guides, the planning notes and the planning tools, in one place.

Explore the library →
Begin a conversation

Most of our work begins with a conversation.

Many relationships begin with an introduction. Business owners and advisors can reach out directly. If the work described here reflects a decision you are facing, you are welcome to begin the conversation.

Please don't include health details or policy numbers. If a renewal review makes sense, we'll ask for the documents securely.

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.