Capital, Engineered to Endure.
Life insurance strategy for founders, business families, and the advisors who guide them.
The Inflection Point:
There is a point in the life of every significant enterprise when the question stops being how to grow capital and becomes how to keep it — intact, liquid, and under your control — as it moves between hands, entities, and generations.
A sale. A succession. A freeze. A transfer to the next generation. The death of a partner the business is bound to buy out. Each is a moment of unusual consequence, where the structure put in place beforehand will either compound in your favour for decades or quietly work against you.
Most planning is built for the years of accumulation. Very little is built for these moments. That is the only thing we build for.
Where We Begin:
Our work begins where conventional planning ends.
When the corporate structure is layered, the tax exposure is real, and the liability that lands on death is measured in the tens of millions, generic advice stops being useful. What is needed is a specialist who designs for that specific moment — and who sees the entire board: the holding companies, the operating businesses, the shareholders' agreements, the estate, and the people who advise you on each.
That is the discipline. Not more products. A structure that holds.
We Answer to One Party:
We are not owned by an insurer, and we are not paid to prefer one. We are retained to get the structure right — which sometimes means telling you, and your advisors, that life insurance is not the answer.
A recommendation is worth only as much as the judgement behind it, and judgement that cannot say no is just sales. Our objectives are aligned with one party. Yours.
What We Build:
Permanence. Liquidity available precisely when an estate, a shareholders' agreement, or a transaction demands it. Tax exposure reduced through structure rather than through risk. And capital that funds the obligation without sitting dead against it — reaching the next generation through the capital dividend account, intact and tax-free.
When the work is done well, the transition looks effortless. That is the point.
Who We Work With:
We work with a deliberately narrow group: founder-operators approaching or recovering from a liquidity event; business families planning succession and estate continuity; and private holding structures repositioning capital across entities and jurisdictions.
And we work with the accountants, tax counsel, and family office leaders who advise them — as collaborators, never as parties to be worked around.
How We Work:
We operate as an extension of your existing team. We map the structures, model the strategy, and implement alongside your legal, tax, and deal advisors — complementing their work.
Work at this level also calls for capacity. We hold established relationships with Canada's major life insurance carriers and their underwriting teams, and the experience to structure and place large, complex cases — the kind that engage reinsurance, and that most advisory practices are not built to handle.
Begin a Conversation:
We work with a small number of families and their advisors at any one time. If you are approaching a capital inflection point — an exit, a succession, a transfer of value across generations — or you advise someone who is, that is the place to begin.
The Founder:
Shannon Gill founded Gilko Capital to do one kind of work well: structuring life insurance for business owners and families at the points where capital changes hands. His engagements sit where insurance intersects corporate finance and estate planning — shareholder and buy-sell funding, key person and executive protection, and liquidity planning for intergenerational transfers — and he works alongside the accountants, lawyers, and other advisors already at the table. The approach is bespoke and deliberately unhurried: understand the goals first, then design a structure that aligns with the corporate plan, the shareholders' agreements, and the family's multi-generational intentions — one built to hold through business cycles, ownership transitions, and succession. Clients and their advisors value the combination of commercial judgement and technical rigour: the ability to make a complex decision clear without making it simplistic. "A transition in capital is never only financial. What's needed at that point is not more options — it's someone who sees the entire board, and who designs for permanence rather than the transaction in front of them."
