Key takeaways
- 01Pre-transaction gifting and trust planning capture the most value before valuations are set.
- 02Residency, entity structure and qualified small business stock eligibility should be reviewed early.
- 03A post-liquidity investment plan prevents the most common mistake: acting too quickly with new capital.
A business sale is often the single largest financial event in a family's history. Yet many founders begin planning only once a buyer is at the table — by which point several of the most valuable opportunities have closed.
Twelve months out
- Confirm eligibility for qualified small business stock treatment and other available exclusions.
- Transfer shares to trusts while valuations are lower and discounts are supportable.
- Review state residency and the timing implications of any planned move.
- Map the family's objectives for the proceeds — security, philanthropy, the next venture.
During the transaction
Deal structure has significant after-tax consequences. Cash versus stock consideration, earn-outs, escrows and rollover equity each carry different risk and tax profiles. We work alongside deal counsel and bankers to model the outcomes, so that founders negotiate with a clear view of what they will actually keep.
After the close
Sudden liquidity creates pressure to act. We recommend a deliberate transition period: proceeds are held in high-quality, liquid instruments while the family's long-term plan and investment policy are finalised. There is rarely a cost to waiting a few months — and there is often a significant cost to rushing.
“The best time to plan a sale is before anyone has asked to buy.”
About the author
James Okafor
Head of Private Wealth
Guides founders and executives through liquidity events, concentrated positions and succession.
Insights are provided for informational purposes only and do not constitute investment, tax or legal advice. Opinions reflect the judgment of the authors as of the date of publication and are subject to change without notice.
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