Case Studies — Advanced Planning Scenarios: What the work
actually looks like

The situation

A second-generation manufacturing owner had a signed LOI and roughly nine months to close. Nearly all of the family's net worth sat inside the operating entity. There was no liquidity outside the business, an outdated buy-sell funded by nothing, and a projected estate tax exposure the CPA had flagged but nobody had solved.

The strategy

• Placed key-person and buy-sell coverage before diligence closed, so the transaction wasn't exposed if the owner died mid-deal.
• Coordinated with the attorney to move new permanent coverage into an irrevocable trust ahead of the sale, keeping the death benefit outside the taxable estate.
• Structured a portion of after-tax proceeds into a laddered fixed annuity position to create a predictable income floor while the rest of the proceeds were deployed.

Where it landed

The deal closed on schedule with the buy-sell fully funded, the estate liquidity problem covered by trust-owned insurance rather than a forced asset sale, and the family's baseline living expenses covered by contractual income independent of the reinvested proceeds.

The situation

A 26-year-old athlete was earning the majority of his lifetime income inside a short window, with agent, tax, and lifestyle costs consuming a large share of gross. His advisors were focused on market investments; nobody had built a floor for the decades after the playing career ends.

The strategy

• Built a deferred income layer with annuity contracts scheduled to turn on in his late thirties, when contract earnings stop and endorsement income is uncertain.
• Used a properly funded permanent policy for tax-advantaged accumulation and access, sized to premium levels his post-career cash flow could sustain, not just his peak-earning years.
• Coordinated with his agent and CPA on entity ownership so premium payments and income timing lined up with his tax picture.

Where it landed

A guaranteed income floor scheduled to begin the year his current contract's earnings run out, plus a permanent policy funded during peak years rather than depending on future income that may never arrive.

The situation

A senior executive held heavily appreciated RSUs and options in a single public company. Diversifying triggered a large tax bill, and the family's entire financial plan depended on one stock price and one employer.

The strategy

• Modeled a staged liquidation schedule with the client's CPA, then used annuity contracts to convert a portion of each tranche into guaranteed income the equity position could never provide.
• Placed permanent life coverage sized to the family's obligations, so a death event during the multi-year diversification window wouldn't force liquidation at a bad price.
• Left the growth allocation with the client's existing investment advisor — our scope was the protected floor, not the portfolio.

Where it landed

Concentration risk reduced on a deliberate schedule instead of a panic sale, with a guaranteed income layer and death benefit that hold their value regardless of what the stock does.

The situation

A multi-generational family owned commercial and agricultural property held across several LLCs. The estate projection showed a nine-figure asset base with a seven-figure tax bill due within nine months of death — and almost no liquid assets to pay it. The likely outcome was a forced sale of income-producing property at whatever price a fast buyer would pay.

The strategy

• Ran a survivorship policy design covering both spouses, priced substantially below two single-life policies for the same death benefit.
• Placed the policy inside an ILIT drafted by the family's estate attorney, with gifting mechanics reviewed against annual exclusion and lifetime exemption planning.
• Stress-tested funding at reduced crediting assumptions so the design didn't depend on optimistic illustration rates.

Where it landed

The estate tax liability is now funded by insurance proceeds arriving outside the taxable estate. The property stays in the family, the income it produces stays intact, and the next generation inherits assets rather than a deadline.

The situation

A digital creator was earning well but through revenue streams that could change with a single algorithm update or brand-partnership shift. Income was routed through an S-corp, retirement contributions were minimal, and there was no protection in place for the business partner who depended on the same revenue.

The strategy

• Established a retained-earnings strategy inside a permanent policy, giving the business a tax-advantaged place to hold profit beyond qualified-plan limits.
• Added disability and life coverage sized to the business's contractual obligations and the partner's exposure.
• Laddered MYGA contracts to convert one strong year into guaranteed cash flow across the following decade, independent of platform performance.

Where it landed

Peak-year revenue converted into contractual income that survives a platform change, plus protection that keeps the business solvent if the person at the center of it can't work.