Key Takeaways
- The period immediately after an exit is the worst time to make major financial decisions.
- Tax planning should happen before the close, not after the wire arrives.
- Liquidity is not the same as financial security. They require different plans.
The moment an acquisition closes and the wire arrives is not, as most founders imagine it, a moment of financial clarity. It is the beginning of a period where the decisions you make in the next 90 days will either compound that outcome meaningfully or erode it through taxes, bad advice, and investments made without a clear framework.
Saim Abbasi learned some of this the hard way on his first exit and applied it more deliberately on subsequent ones. The lessons are worth sharing.
Tax Planning Before Close
The most common and expensive mistake founders make is not engaging with tax planning until after the deal closes. By the time the wire arrives, most of the tax optimization opportunities have already passed. The structure of how the deal is done, whether it is an asset sale or a stock sale, how income and capital gains are allocated, what jurisdiction's rules apply, can make a material difference to the after-tax outcome. None of those decisions can be made retroactively.
Working with a tax advisor who specializes in startup transactions, not a general accountant, at least 60 days before the close is not overhead. It is an investment with a very clear return.
The Deployment Pause
Saim's personal rule after each exit: do not make any significant investment decision with exit proceeds for 90 days. Not real estate. Not into new ventures. Not into public markets. The 90-day period is for financial planning, not financial action. Decisions made from a position of new liquidity without a clear framework are almost always decisions made emotionally rather than strategically.
What Financial Security Actually Requires
The distinction between liquidity and financial security is underappreciated by founders who have never had significant liquidity before. Having money in your account does not mean you have a financial plan. It means you have optionality that requires a plan to convert into actual security. The plan includes: what is my personal runway if I never earn another dollar from this point, what are my obligations that require ongoing cash flow, and how do I structure my assets to serve both the short-term and the long-term?
Those questions are worth answering with a financial advisor who has worked with entrepreneurs specifically, because the planning assumptions for founders are different from those for executives or employees.
"Most founders spend their career building wealth and about 90 days determining whether they keep it."