Dan O'Shaughnessy seated on a stool
For the ones who built the empire

You are wealthy.
How do you make sure
it stays that way?

You built wealth through discipline and sacrifice. Without the right structure, the government decides what happens to it at death. Not you.

73%
of estate tax bills arrive at an unexpected time
$0
in liquidity when assets are tied up in a business
Ex Meritis.
Ex Mentis.
Ex Familia.
The problem most business owners face

You built your wealth inside your business.
That is also where it is most at risk.

Corporate wealth looks strong on paper. Without the right structures, it is exposed to tax at death, inaccessible during transition, and impossible to divide without liquidating what took decades to build.

What your accountant sees
  • Strong retained earnings in the corporation
  • Valuable real estate, business assets, investments
  • A well-structured operating company
  • Healthy cash flow and growing enterprise value
What is missing
  • Tax-efficient access to corporate cash, now and at death
  • Liquidity to fund your estate without a forced asset sale
  • A structure that equalizes your estate across your family
  • A plan for business continuity when the key person is gone
The Standard

Planning worthy of what you've built.

OSF exists for those who see wealth as stewardship. Three pillars. One standard.

I
Merit

You earned your success through discipline, sacrifice, and intelligent risk. Your planning should reflect that.

II
Mind

Founders think in systems. Your planning should match: structured, decisive, and built for the long term.

III
Family

Everything comes back to the people you live for. We build structures that protect your estate and preserve opportunity across generations.

"The right planning preserves wealth and protects what matters most."

At OSF Financial, planning is stewardship. We reflect who our clients are at their best, and we build structures that endure.

The opportunity inside your corporation

Your retained earnings are one of the most powerful assets you own. Most business owners are not using them fully.

After-tax corporate dollars can be structured to create permanent, tax-advantaged wealth. Growing inside your corporation, accessible to your estate, outside of probate. This is the conversation most advisors never start.

"The highest use of corporate surplus is not a savings account. It is a structure that compounds, protects, and transfers tax-efficiently."

OSF Financial · The Corporate Wealth Conversation
01 — Accumulation
Make idle corporate cash work harder

Redirect retained earnings into a structure that grows tax-sheltered inside the corporation, protected from passive investment income tax.

02 — Protection
Protect the value you've built

A key person event: disability, death, departure. Any one of them can destabilize a business overnight. The right structure means the enterprise survives.

03 — Transfer
Move wealth to the next generation, on your terms

Corporate-owned structures fund estate taxes, equalize inheritance, and create a tax-free transfer at the moment it is needed.

Who We Serve

A minimum mindset. Not a minimum net worth.

OSF clients are defined by how they think, not by what they have. High-net-worth entrepreneurs who built their success and want to protect it with the same intention.

  • Family-first values, motivated by legacy over accumulation
  • Strategic thinkers who engage as partners, not students
  • Referral-only. They vet advisors through trusted networks
  • Discerning: they want high-value, low-noise engagement
OSF Financial · Difference

"We reflect who you are at your best."

One integrated process, built around your full picture.

"At death, the government becomes your largest beneficiary. Unless you planned otherwise."

The deemed disposition at death triggers capital gains on every asset you own. For a founder with a valuable business, real estate, and investments, that bill arrives immediately. Whether your family has cash to pay it or not. This is solvable. But only before it is needed.

The Cottage
Your family should not have to choose between the memory and the mortgage.

Capital gains on recreational property can force a sale no one in your family wants. The liquidity was not there. Structure changes that outcome.

The Business
Succession without a fire sale requires a plan.

Who takes over? Who buys out the departing partner? Who funds the transition? These are answerable questions. But only with structure in place before the event.

The Children
Equal is not always equitable. Equitable requires intention.

One child runs the business. Another lives abroad. A third has no interest in either. Treating them equally may be the most unfair thing you do. There is a better way, designed in advance.

Before you move on

Six questions every affluent business owner at your level should be able to answer.

These are the questions that separate a plan that looks good from one that holds.

1

"If I died tonight, does my family have enough liquid cash to cover my estate tax without selling anything?"

Most founders do not know. The answer changes everything.

2

"Is my corporate surplus growing tax-efficiently, or sitting exposed to passive investment income rules?"

There is a structure for this. Most founders have never been shown it.

3

"Does my succession plan reflect what I actually want, or just what was easiest to document?"

What is simple for the advisor is often complex for the family.

4

"Can I equalize my estate between my children without one of them inheriting a problem?"

Structure lets you be generous and fair. Without it, you choose one.

5

"If my key person, or I, could not come to work tomorrow, does the business survive financially?"

Key person risk is the exposure most business owners acknowledge and ignore.

6

"When did someone last challenge my planning, not to sell me something, but to make sure it still holds?"

The best time to review a plan is when nothing is wrong. That is the conversation OSF initiates.

How We Work

Planning done differently.

Step 01
Strategic Conversation

Every client enters OSF through a structured introduction. We listen first. Alignment is confirmed before any engagement begins.

Step 02
Whole-System Roadmap

We integrate your business, personal, and legacy intentions into one clear strategy. Clean direction. The reasoning behind every decision.

Step 03
Ongoing Partnership

OSF is not a transaction. We review, evolve, and stay ahead. The best planning is a continuous conversation.

Dan O'Shaughnessy, Founder of OSF Financial
The Founder

"I want to be the first call. When things are going well, and when they are not."

I built OSF for business owners who think beyond the next fiscal year. My role is to bring the right people, the right conversations, and the clarity that creates opportunity.

Every interaction leaves the client feeling understood and strategically guided. That is the standard. That is OSF.

— Dan O'Shaughnessy
The people behind the planning
Dan O'Shaughnessy
Dan O'Shaughnessy
Founder & Financial Advisor

Dan built OSF around a single observation: the people achieving the most rarely have someone who truly understands them.

He began his career at Goldman Sachs, working with some of the world's most complex organizations, before moving to Bank of America Merrill Lynch where he helped businesses raise equity on the Toronto Stock Exchange. Through those years, Dan worked alongside founders and executives who were building extraordinary things, and who deserved more than transactional advice.

OSF is the answer to what was missing. Whether Dan was captaining the Syracuse Rowing Team, competing at Cambridge, or leading some of North America's most sophisticated financial conversations, he has always operated at the level his clients live at.

Dan understands because he has been there, and continues to build alongside those with shared aspirations.

Mary Som
Mary Som
Chief Operating Officer

Mary ensures that everything OSF promises, OSF delivers.

With a background in criminology and social science, she has a natural instinct for how the details connect, and what happens when they don't. Since joining the firm in 2013, she has brought that same discipline and care to every facet of operations that keep client relationships running exactly as they should.

Mary is why OSF's standard of excellence isn't just a philosophy. It's a practice.

Vonn Prak
Vonn Prak
Manager, Client Services

Once a plan is in place, Vonn is the person who makes sure it stays that way.

She works directly with existing clients, managing policies, answering questions, and ensuring every commitment OSF has made is honoured. Her role is relational. The trust a client places in their advisor deepens with every interaction that follows the signing table.

She is why OSF clients feel looked after, not just planned for.

One Partnership. One standard. Every client, every time. Ex Meritis. Ex Mentis. Ex Familia.
From merit. From mind. From family.
How OSF works

Clarity on what is missing. A plan for what to do about it.

OSF works with business owners who have built real wealth and want the structure around it to reflect that. We lead with the right questions.

Referral and introduction only. Every client relationship begins with a vetted introduction. Fit matters as much to us as it does to you.
We integrate what others fragment. Business, personal, estate, and legacy in one coherent strategy. No handoffs. No gaps.
We never skip steps. The sequence matters. Solving the right problem at the wrong time is still the wrong answer.
The conversation is ongoing. Not a transaction. Not a review every three years. A continuous partnership because your situation is always evolving.
If those six questions stayed with you

"That's usually a sign the conversation is worth having."

We are the partner beside the affluent who are ready to approach their wealth the way it was built: with intention, structure, and a long-term view.

OSF Financial

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