Pre- and post-exit founders, operators, and fund principals; the tax position differs at each stage.
Three principals, three tax positions, one architecture.
The technology position rarely fits the conventional shape of private wealth. The pre-exit founder holds founder shares acquired at nominal value, options vesting against tenure or performance, secondary proceeds from prior tenders, and frequently a parallel angel book accumulated alongside the operating company. The post-exit founder holds the proceeds of a sale or public listing — sometimes liquid, sometimes restricted, often partially deferred — alongside an emerging set of decisions about what comes next: passive investment, the family office, the second company, the fund. The fund principal holds GP commitments, carried-interest waterfalls vesting across fund life, and a personal balance sheet whose returns are correlated with the same fund their working hours fund.
Each of the three positions is composed of instruments unfamiliar to the conventional advisor and consequential at the architectural level. Stock benefit timing under s. 7 of the Income Tax Act. The Qualified Small Business Corporation share status, where structure permits, and the lifetime capital gains exemption multiplied across the family ahead of a contemplated transaction. The Delaware C-corp held by the Canadian-resident founder, with all the cross-border treaty work that follows. The carried interest, taxed in Canada under a regime that resembles but does not match the U.S. position. Each of these is a structural decision that compounds across the working life.
Senatus serves as the architectural mandate that holds the technology principal’s position in coherent relation. The corporate counsel inside the company continues to draft the cap-table and the option plan. The cross-border tax counsel continues to attend to the U.S. exposure. Senatus convenes the table and remains accountable for the integrity of the whole — through the building chapter, the exit, and the years that follow.
Four points the operating cadence tends to defer.
Each is composed in coordination with the family’s existing tax counsel, U.S. tax counsel where applicable, and the corporate counsel inside the company. None requires waiting for a transaction window to begin.
Pre-exit architecture, composed against the next round and the eventual exit.
The Qualified Small Business Corporation status of the founder shares, where structure permits. The lifetime capital gains exemption multiplied across the family under s. 110.6 of the Income Tax Act. The estate freeze inside the holdco that owns the founder shares. The treaty position if the company is incorporated in Delaware while the founder is Canadian-resident. The decisions made now compound through every subsequent valuation event — and become unavailable, in many cases, after the next priced round.
Vesting, secondaries, and the timing of the s. 7 stock benefit.
Option exercises, secondary tender offers, RSU vests inside the company plan, and the timing of the resulting stock benefit under s. 7 of the Income Tax Act. Each is a tax decision before it is a liquidity decision; each is more efficient or less efficient depending on the year in which it lands and the holdco structure that receives the proceeds. The work is sequenced years in advance with the family’s tax counsel.
Carried interest, treated as the structural instrument it is.
For fund principals, the carry vests across fund life on the GP’s own schedule, returns according to a waterfall composed years before any of the underlying portfolio liquidity arrives, and is taxed under Canadian rules unlike the U.S. counterpart. The architecture composes the carry inside an entity structure that permits subsequent estate planning and family inclusion, holds the timing against the family’s broader tax position, and aligns it with the GP commitment funded against personal capital.
The post-exit architecture, composed before the proceeds arrive.
Year one beyond the exit is the year in which the architecture either holds or the family pays for not having composed it. The entity layering for the proceeds, the investment policy composed against the family’s long horizon, the philanthropic timing — donation of QSBC shares before sale, where structure permits, materially exceeds donation of cash after — and the decision about what comes next: the family office, the second company, the fund. All composed before the wire arrives, not after.
The cap-table view, then the rhythm of the venture cycle.
The engagement begins with a documented review of the principal’s complete position — the cap-table holdings, the option grants outstanding, the secondary history, the GP commitments and carried-interest schedule where applicable, the holdco structure, the cross-border posture, and the family balance sheet around all of it. The review is held in confidence and shared only with advisors the principal expressly nominates.
From that foundation, the relationship operates on the cadence the venture cycle permits: a structural review against the next priced round or fund vintage, working sessions ahead of secondary windows, vesting events, and material transactions, and continuing coordination across the years that approach, execute, and follow the exit.
“The cap table I understood. The holdco that owned my shares I had set up four years earlier without a clear architectural intent. The U.S. position arrived with the Series B. The architectural review composed those three layers as one position, ahead of the next round. By the time we priced the secondary, the structure was sequenced; by the time the strategic conversations began, the family was in front of them, not behind.”
If the position is composed in cap-table mechanics, vesting schedules, or carried interest, the next step is a private conversation.
Senatus accepts a limited number of new relationships each year, predominantly through private referral. A member of the Private Office will respond, in confidence, within twenty-four hours.
Request a Private ConversationTwelve adjacent audiences.
Most principals belong to more than one. The architecture is composed for the family in front of us; the descriptions below are how families most often arrive.