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Intergenerational
Planning &
Estate Freezing

Protect the wealth you've built and transfer it to the next generation with precision — minimizing tax exposure, preserving family harmony, and securing your legacy across both Canada and the United States.

Canada • United States • Cross-Border Legacy Planning
0%
Freeze-Day Tax
50+
Jurisdictions
15+
Yrs Experience
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Estate Freezing Family Trust Planning Succession Planning Corporate Reorganization Gift Planning CRA & IRS Compliant
Estate Freezing Family Trust Planning Succession Planning Corporate Reorganization Gift Planning CRA & IRS Compliant
02

Our Full Service Suite

Three integrated disciplines — working in concert to transfer your wealth efficiently and protect your family's future.

Section 86 / Section 85 Rollovers

Tax-deferred reorganization of private corporation shares to lock in current values and shift future growth to the next generation.

Crystallization of Capital Gains Exemption

Strategic use of the Lifetime Capital Gains Exemption (LCGE) to shelter qualifying small business corporation shares from tax.

Share Capital Restructuring

Creation of new share classes — common, preferred, or hybrid — to facilitate income splitting, control retention, and equity transfer.

Freeze Valuation & Documentation

Independent business valuation at time of freeze, with comprehensive documentation to support CRA or IRS scrutiny.

Re-freeze & Second-Generation Planning

Revisiting and refreshing a prior freeze to reflect changed business values, family circumstances, or tax legislation updates.

Post-Mortem Estate Freeze Unwinding

Coordinated post-death planning including pipeline planning and loss consolidation to reduce double-taxation on death.

Business Succession Roadmap

Comprehensive planning to transition your business to family members, key employees, or third-party buyers in a tax-efficient manner.

Shareholder Agreements

Drafting and reviewing buy-sell provisions, shotgun clauses, valuation mechanisms, and right of first refusal terms.

Key Person & Leadership Transition

Identifying successor leadership, structuring compensation, and mitigating key-person risk during transition periods.

Life Insurance in Succession

Corporate-owned life insurance strategies to fund buy-sell agreements and provide liquidity at shareholder death.

Cross-Border Succession Structures

Coordinating Canadian and US succession obligations, including treaty provisions, exit taxes, and dual-resident shareholder issues.

Family Charter & Governance

Facilitating family governance frameworks — councils, charters, and communication structures — to prevent conflict and align expectations.

Family Discretionary Trusts

Establishing inter vivos or testamentary trusts to shift income and capital to lower-bracket family members while retaining control.

Alter Ego & Joint Partner Trusts

Tax-deferred transfer of assets into trusts that avoid probate, maintain privacy, and provide seamless control during the settlor's lifetime.

Prescribed Rate Loan Strategies

Lending to a family trust at the prescribed CRA rate to split investment income with lower-income family beneficiaries.

Annual Gift Planning (US & Canada)

Leveraging annual gift exclusions and Canadian attribution rules to transfer wealth incrementally, tax-free, year over year.

Charitable Giving Strategies

Donor-advised funds, charitable remainder trusts, and direct donation strategies to meet philanthropic goals while reducing taxable income.

Cross-Border Trust Compliance

Navigating T3, T1141, FBAR, and Form 3520 reporting requirements for trusts with Canadian and US beneficiaries or trustees.

03

Our Planning Process

A structured, four-stage approach — from discovery to implementation — ensuring nothing is left to chance.

01

Discovery & Valuation

We review your current structure, assets, family situation, and objectives — and obtain a defensible business valuation.

02

Strategy Design

We model multiple scenarios — comparing tax impact, control, flexibility, and cost — and present a recommended plan with alternatives.

03

Legal Implementation

Coordinating with your legal counsel to draft trust deeds, shareholder agreements, corporate resolutions, and reorganization documents.

04

Ongoing Review

Annual reviews to adapt your plan as tax laws, business values, and family circumstances evolve — keeping your strategy current.

04

The T&F Difference

Intergenerational planning demands more than technical knowledge. It demands trust, discretion, and deep cross-border expertise.

Dual-Jurisdiction Mastery

Most advisors plan in one country. We coordinate Canadian and US estate, gift, and succession rules simultaneously — avoiding costly surprises at the border.

Integrated with Tax & Accounting

Because we handle your ongoing tax filings and books, your freeze and succession plan is built on real, current numbers — not estimates.

Multigenerational Relationships

We work with families across generations — so when your children become clients, the institutional knowledge of your family's financial history is already there.

Proactive, Not Reactive

Estate planning done at death is crisis management. We begin planning years in advance — when the most tax-efficient strategies are still available to you.

Strict Confidentiality

Family wealth transitions are deeply personal. Every engagement is handled with the highest degree of discretion, privacy, and professional confidentiality.

Professionals We Collaborate With

Estate Lawyers Business Valuators Trust Officers Insurance Advisors Family Mediators US Tax Counsel

Service Packages

All engagements are customized to your family and business situation. Contact us for a confidential quote.

Foundations

Individuals &
Small Families

For individuals beginning to think about transferring wealth and protecting assets for the next generation.

Family trust establishment
Basic estate freeze analysis
Gift planning strategy
LCGE crystallization review
Annual review meeting
Get a Quote
Cross-Border

Dual-Jurisdiction
Families

For high-net-worth families with assets, beneficiaries, or business interests spanning Canada and the United States.

Everything in Business Succession
US gift & estate tax planning
Cross-border trust compliance
Dual-resident shareholder planning
Family governance framework
Get a Quote
05

Frequently Asked
Questions

These are complex, high-stakes decisions. We welcome every question — no matter how basic or technical. Start with a free, confidential call.

Ask Us Anything
An estate freeze is a tax-planning strategy that locks in the current value of your assets — typically shares in a private corporation — so that all future growth accrues to the next generation. Any capital gains accrued up to the freeze date remain your liability, but growth after the freeze belongs to your children or a family trust. Business owners with growing companies benefit most, as it caps your eventual tax exposure.
The earlier the better. The most powerful strategies — like an estate freeze or prescribed rate loan — are most effective when the business or portfolio is growing and the freeze value is still relatively low. Waiting until retirement or illness significantly reduces your options. That said, it's never too late to improve your position.
No — a properly structured freeze lets you retain full voting control and your economic entitlement up to the freeze value. New common shares (which carry future growth) are issued to your children or a family trust, but you continue to hold preferred shares with voting rights. Control is entirely your choice.
It adds layers, but it's manageable with the right team. When US-person beneficiaries are involved, we must consider US gift tax reporting on transfers, the treatment of foreign trusts under US tax law (Forms 3520 and 3520-A), and potential PFIC or CFC issues if a Canadian corporation is involved. This is precisely the cross-border complexity we specialize in.
A will governs the distribution of your assets after death. An estate freeze is a living transaction — it happens now, during your lifetime, and transfers future growth to your successors while you remain alive and in control. The two strategies complement each other; a comprehensive plan incorporates both.

Your Legacy.
Purposefully Planned.

Whether you're starting a first freeze, restructuring a family trust, or coordinating a cross-border succession — start with a free, confidential consultation with our team.

(647) 528 0200 info@bobbyfinancials.ca ON & NY