For most business owners, the company is the portfolio. That's a natural consequence of building something — but it also means your financial security is concentrated in a single illiquid asset. What happens to your wealth if the business doesn't sell at the price you need? Or sells tomorrow?
We work with business owners at every stage — from building personal savings independent of the business, to structuring a tax-efficient exit, to investing the proceeds after the sale. All as a fee-only fiduciary, with no incentive other than getting it right for you.
Business owners face a unique financial planning challenge: the asset driving most of their net worth is illiquid, undiversified, and dependent on factors — market conditions, buyer appetite, your own health — that are partially outside your control. Building personal wealth that's independent of the business isn't disloyalty to it. It's the only way to ensure your financial security doesn't hinge on a single transaction going perfectly.
Having most of your net worth in one company — even a successful one — is a level of concentration no prudent investment advisor would recommend for a public stock portfolio. The business is different, but the risk isn't.
Unlike a stock portfolio, you can't sell 10% of your business on a bad day to cover expenses. Your personal finances need to be resilient independent of any business distribution or eventual sale.
The sale price you need to retire comfortably may not be the price the market will pay. A financial plan that depends on achieving a specific exit valuation is a plan with a single point of failure.
A business exit is typically the largest financial event in an owner's life. It is also the most complex — involving tax strategy, deal structure, personal financial planning, and often estate considerations. Waiting until you're ready to sell leaves almost no room to optimize any of it.
Maximize contributions to tax-advantaged accounts, build liquid investment assets, and reduce personal financial dependence on business distributions. Your retirement plan should be able to survive a sale that falls short of expectations.
Clean up financials, reduce owner dependence, and document systems that increase transferable value. Evaluate entity structure for tax efficiency at exit. Consider gifting strategies to shift appreciation out of your estate before valuation increases further.
Asset sale vs. stock sale has dramatically different tax implications. Installment sales, earnouts, and opportunity zone reinvestment can all reduce the immediate tax burden. Qualified Small Business Stock (QSBS) exclusion may apply if you've held C-corp shares for 5+ years — potentially excluding $10M or more in gains from federal tax entirely.
A large lump sum at retirement requires a fundamentally different investment approach than ongoing savings. We build a transition plan that accounts for tax liability, liquidity needs, and the shift from wealth accumulation to income generation — without rushing the deployment of proceeds into market risk.
Many business owners have never had to live without business income. We build a retirement income plan that replaces that cash flow through investment income, Social Security optimization, and systematic portfolio withdrawals — structured for tax efficiency and longevity.
Business owners have access to retirement plan options that offer far higher contribution limits than the standard employee 401(k). Choosing the right structure — and funding it consistently — is one of the most powerful tax reduction tools available. We evaluate each option in the context of your business structure, income level, and employee situation.
The highest contribution limit available to self-employed individuals with no full-time employees. Combines employee and employer contributions, includes Roth option, and allows loans. The most powerful tax deferral vehicle for owner-only businesses.
Best for: Owner-only businessesSimpler to administer than a 401(k), with contributions limited to 25% of compensation. No Roth option or loan provision. If you have employees, contributions must be made proportionally for all eligible employees — making it less flexible than a Solo 401(k) in some situations.
Best for: Simplicity, variable incomeFor high-earning business owners who want to maximize tax-deferred savings beyond 401(k) limits, a defined benefit plan can allow annual contributions well above $100,000. Requires actuarial calculations and ongoing funding commitments, but can be extraordinarily powerful for high-income owners approaching retirement.
Best for: High earners, late startersLower contribution limits than a 401(k) but simpler and less expensive to administer for businesses with employees. Requires employer matching contributions. Best suited for small businesses that want to offer a retirement benefit without the administrative complexity of a full 401(k) plan.
Best for: Small teams, low adminBeyond exit planning and retirement accounts, business owners face a set of financial planning challenges that most advisors aren't equipped to address comprehensively. We work across all of them.
If you hold Qualified Small Business Stock in a C-corporation held for 5+ years, you may be eligible to exclude up to $10M — or 10x your basis — in capital gains from federal tax entirely under Section 1202. This is one of the most valuable and underutilized provisions in the tax code for startup and small business owners.
If the business's value is tied to you personally, what happens to it — and to your family — if you're incapacitated or die? We evaluate key-man insurance as part of a comprehensive risk management strategy, without the commission incentive that drives most insurance recommendations.
A properly funded buy-sell agreement ensures that if a co-owner dies, becomes disabled, or wants to exit, the transition happens smoothly and at a fair price. We evaluate funding structures — life insurance, sinking fund, installment — in the context of your overall financial plan.
S-Corp vs. C-Corp vs. LLC affects not only current-year taxes but exit tax treatment, QSBS eligibility, and estate planning. We work with your CPA and attorney to ensure your entity structure aligns with your long-term financial goals — not just this year's tax bill.
Business owners with appreciated company stock or assets can use charitable vehicles — donor-advised funds, charitable remainder trusts — to reduce capital gains on exit, generate income, and fulfill philanthropic goals simultaneously. Timing relative to an exit is critical.
The value of a growing business can rapidly outpace estate tax exemptions. Strategies including GRATs, irrevocable trusts, and installment sales to intentionally defective grantor trusts can shift appreciation to heirs at a fraction of the estate tax cost — but require planning well before a sale.
Schedule a conversation with Hooman Altafi to discuss your business, your exit timeline, and how to build personal financial security that doesn't depend on everything going perfectly.
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