The Situation:
By the early 2000s, Mary-Kate and Ashley Olsen had built a tween merchandise and media empire. But the business had become bloated, spending was out of control, and much of the organization was entrenched in cash cows like the Walmart clothing line. The sisters were becoming adults with a new vision: fashion entrepreneurship. Their father, Bill's longtime colleague in the mortgage industry, asked him to take the financial reins and protect his daughters from the all-too-common child-star collapse.

Bill’s Approach:
Led the wind-down of the Walmart line, eliminated staff and overhead tied to legacy operations, and restructured Dualstar Entertainment into separate LLCs so the sisters could maintain joint business interests while protecting individual assets. Assembled legal, financial, and entertainment specialists to renegotiate distribution deals while the twins retained full ownership. Held regular meetings, weekly during critical periods, focused on both dollars and life choices.

The Outcome:
Mary-Kate and Ashley launched The Row, Elizabeth and James, StyleMint, and Olsenboye. By 2007, they ranked among Forbes' 20 wealthiest women in showbusiness. They doubled their assets and emerged from the 2008 financial crisis unscathed. In 2012, they won Womenswear Designer of the Year from the Council of Fashion Designers of America.

The Lesson:
"Reinvention is essential in business. Kill off cash cows in an orderly fashion when long-term strategy reveals them draining cash flow, talent, and overall entrepreneurial energy."