Profile
A couple in their mid-60s. He owns a business and commercial real estate, with a combined household income of approximately $250,000 per year. Their net worth exceeds $12 million. They have children and grandchildren.
The Situation
After decades of building — a business, a portfolio of commercial real estate, and a family — this couple was ready to retire. But the path from “ready” to “retired” was far from straightforward.
The business needed a succession or sale plan. The commercial real estate required proper valuation and cost basis documentation. They wanted to purchase a mountain home in the $400,000 to $600,000 range. Income structuring was a critical question — when should each spouse begin Social Security, how should they draw from investment accounts, and what would happen to distributions during a business transition period?
Medicare enrollment was approaching for one spouse. And while they had always wanted to help their children and grandchildren financially, nothing had been formalized. Every piece was connected, and changing one variable affected everything else.
Statement of Financial Purpose
“We desire financial independence so we can work less, travel more, and help our family when needed — all without worry of whether we have enough money to pay our bills and do the things we want to do.”
What the Plan Focused On
- ●Retirement timing within a defined income target
- ●Purchasing a mountain home
- ●Helping children and grandchildren in a structured, intentional way
- ●Traveling more — with freedom and without financial worry
Action Items
- ●Establish spending clarity to define a realistic retirement income need
- ●Facilitate an exit and retirement timing conversation
- ●Health insurance gap analysis for the pre-Medicare period
- ●Income structuring across Social Security, investment accounts, and business distributions
- ●Analyze profit distribution impact on all shareholders during the transition
- ●Commercial real estate documentation — valuation, cost basis, and holding strategy
- ●Mountain property search parameters and purchase planning
- ●Social Security timing analysis for both spouses
- ●Medicare enrollment coordination for the approaching spouse
- ●Business valuation updates for succession or sale planning
- ●Roth conversions during lower-income transition years to reduce future tax burden
Why This Story Matters
A $12 million net worth doesn't mean retirement is simple — especially when the majority of that wealth is tied up in a business and commercial real estate. These aren't liquid assets you can simply draw from. They require careful sequencing: when to sell, how to transition, what to hold, and how to replace active income with sustainable distributions.
Without a coordinated plan, this couple could have faced unnecessary tax consequences, left money on the table with Social Security, or failed to formalize the family giving they cared about. With a plan, every piece — the business, the real estate, the new mountain home, and the family legacy — moved forward in the right order, at the right time.