Client Goals

A self-employed couple were planning to retire within a two-to-three-year time frame and wanted to be sure they were in position to comfortably meet all their goals. They had investments spread among multiple banks and brokerage firms. They were considering selling their suburban family home and purchasing a condo in downtown Chicago in addition to buying a home in a warmer climate. They also wanted to begin to make annual gifts to each of their two adult daughters and three grandchildren.

Our Guidance

Income Transition

Helping them understand the mechanics of transitioning from living off cash flow generated by the business to receiving regular cash flows from their portfolio.

Portfolio Consolidation

Creating a portfolio to prevent redundancy across their investment holdings and be better aligned with their return expectations.

Capital Sufficiency Analysis

Helping to determine the necessary size of the monetization event (sale of business) to support their long-term financial goals and objectives. Stress-testing the return and inflation assumptions to determine sensitivity of meeting their financial goals and overall objectives to uncontrollable market conditions.

Pre-Sale Business Ownership Structuring

Working with their accountant and estate planning attorney to determine what ownership adjustments should occur in advance of a sale to minimize estate and income taxes.

Cash Flow Analysis

Determining annual spending ranges based on lifestyle needs and desires to make annual tax exclusion gifts.

Educational Financing

Evaluating different options for assisting with educational expenses of their grandchildren (and potentially more in the future).

“Snowbird” Guidance

Analyzing the full costs of purchasing a second home in a warmer climate along with evaluating other decision factors involved with splitting their time between two locations.


Evaluating current insurance portfolio of health care, long-term care and property & casualty to determine if coverages are adequate, and recommend changes.

Centralized Data Aggregation

Creating an inventory of all their financial data to ensure all information is documented and accessible to family members should an emergency occur.

Philanthropic Structuring

Establishing a charitable vehicle to structure their ongoing philanthropic giving.