At Theodor Hennessey & Ross in Toronto, we don’t slap formulas onto lives built from unique stories. Your goals, your setbacks, your aspirations as an affluent Canadian—they guide everything we do. Financial planning here is fluid, adaptive, and designed for those who know that success is never static. Whether you’re protecting decades of hard work, building a legacy, or shaping your family’s financial future, we are here to help.
Pre-retirees and retirees: Build it, enjoy it, pass it on
You’ve spent years accumulating wealth, and now comes the pivot—moving from growing to using it wisely. But transitioning doesn’t mean losing momentum. Theodor Hennessey & Ross helps you design a life where wealth creates freedom, not fear of overspending.
- Living longer, living better: Retirement could span three decades—your income plan should last the distance.
- Tax strategy meets lifestyle goals: Capital gains, RRIF withdrawals, and pensions all have a rhythm—we make sure yours doesn’t miss a beat.
- A legacy that resonates: We ensure your estate doesn’t vanish under taxes but remains a statement of your care and vision.
Let your retirement years be everything you worked for—luxury where it counts and security at every turn.
Business owners and entrepreneurs: Legacy-level growth
You didn’t build your business by playing small. So why would your financial strategy shrink in the face of expansion or succession? As your financial planner, we understand that your business and personal wealth are intertwined.
- Succession strategy: Passing the torch doesn’t mean dropping the baton. We create succession plans that maintain your business’s strength while protecting your lifestyle.
- Tax efficiency that works for you: Holding companies, shareholder agreements, dividends—done right, they’re not tax obligations but wealth-saving tools.
- Investment beyond the business: Diversification matters—because relying on one source of income could mean standing on one leg when the wind shifts.
Whether you’re scaling or selling, our strategies ensure that your next step is steady.
Affluent families: Strengthen your legacy across generations
Family wealth isn’t just about inheritance—it’s about creating opportunity without the burden of expectation. We build plans that honor your family’s dynamics, preparing the next generation to handle their role with confidence and purpose.
- Tax-friendly transfers: Smooth, structured, and secure—less bureaucracy, more benefits.
- Education for future stewards: We prepare heirs for sudden wealth events with practical guidance and ongoing support.
- Custom estate planning solutions: Every family is different, and so is every estate. Our plans reflect your family’s goals, values, and future plans.