A company heading toward an IPO opens a narrow window to plan before lockups, trading restrictions, and public scrutiny take over. Start this process at least a year out — ideally two.
Take stock of the grants
Locate plan documents and grant agreements
Identify the grant type for each award — NQSOs, ISOs, restricted stock, RSUs, or founder shares
Inventory outstanding grants by date and quantity
Confirm vesting status and prior exercise history
Run the tax assessment
Evaluate early-exercise opportunities before the spread widens
Confirm any past 83(b) elections and how they affect basis
Check RSUs for "double-trigger" vesting conditions
Determine Section 1202 QSBS eligibility — see the dedicated QSBS checklist for the full eligibility, documentation, and stacking analysis
Prepare for lockup and ongoing restrictions
Confirm whether the lockup is a single period or tiered
Model multiple price-target scenarios to manage expectations
Obtain the company's trading calendar and blackout schedule
Evaluate setting up a Rule 10b5-1 plan ahead of the IPO
Build the wealth and estate plan
Define short-term liquidity needs and long-term goals
Devise a diversification strategy for the post-IPO position
Review wills, trusts, powers of attorney, and healthcare directives
Evaluate gifting or GRAT strategies while the exemption remains elevated
Confirm the full advisory team is assembled — tax, wealth, and estate counsel
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