When a Liquidity Event Becomes a Second Full-Time Job Selling a business is supposed to create freedom. The term sheet is signed, the wire hits, tax estimates are penciled in, and for a short while it feels like the hard work is finally behind you. Then the emails and ideas start piling up: cash management, tax timing, new investment pitches, family requests, charitable goals. Before long, your “post-exit” life looks a lot like another operating role. The risk did not go away

When a nonprofit feels financially strong on paper but strained in real life, the problem is often not performance; it is timing. Many organizations keep a well-diversified portfolio, follow a classic spending rule, and still find themselves rushing to free up cash before a major grant cycle or payroll. The money is there, just not in the right place at the right moment. In our work with nonprofits, we see one theme repeat: the investment strategy is built around long-term re