Pre & Post-IPO Planning
Exercise, sale, and diversification strategies for IPOs, acquisitions, and equity liquidity events.
Pre & Post-IPO Planning: When Timing Changes Everything
If your company plans to go public, just went public, or was acquired, your wealth can shift overnight — often in concentrated equity you cannot freely sell. RSUs, ISOs, NSOs, and founder shares each carry different tax rules, exercise decisions, lockup restrictions, and blackout windows. The gap between paper wealth and spendable wealth is where most costly mistakes happen.
Many executives wait until shares are liquid to plan. By then, exercise windows have closed, AMT exposure is fixed, withholding choices are locked in, and diversification options are narrower. The highest-leverage work typically happens 6–12 months before a liquidity event — sometimes earlier if options are already exercisable.
Clexperus helps you navigate the full arc: before a date is announced, through IPO and lockup, and into a tax-efficient post-liquidity foundation — always coordinated with your CPA, not in place of them.
What We Do: Equity Compensation & Liquidity Coordination
We specialize in clients navigating IPOs, acquisitions, and major equity liquidity events. We work alongside your tax preparer and existing advisors.
We help you:
- Understand how your equity is taxed — RSUs, ISOs, NSOs, ESPPs, and founder shares
- Model pre-tax and after-tax outcomes across exercise, sale, and hold scenarios
- Coordinate with your CPA on ordinary income, capital gains, and AMT exposure
- Develop exercise and sale strategies — which grants, how much, and when
- Plan for lockup periods, trading windows, and cash needs before shares are freely salable
- Educate and coordinate on 10b5-1 plans where appropriate
- Review early exercise and 83(b) election considerations with your tax team
- Build post-liquidity diversification and investment strategy after the lockup ends
- Align proceeds with retirement, estate, and charitable goals
Clexperus does not provide tax preparation, legal advice, or securities law counsel. IPO and equity planning is coordinated in partnership with your CPA and legal advisors.
One Journey: Before, During, and After Liquidity
Whether your company has announced an IPO, is rumored to go public, or you just went through an acquisition — planning is one continuous arc. We help at every stage, including when no date has been set yet.
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EARLY
Before a Date Is Set
Private secondaries, early exercise, 83(b) review, and scenario modeling while equity is still illiquid.
-
6–12 MO
Approaching the Event
Exercise strategy, AMT modeling, withholding, and 10b5-1 planning before shares are tradable.
-
LOCKUP
IPO & Restrictions
Cash needs, concentration risk, trading windows, and sale pacing during restrictions.
-
AFTER
Post-Liquidity
Diversification, investment strategy, and retirement, estate, and charitable alignment.
What You Can Expect From Clexperus
- Education on the types of equity you hold and how each is taxed
- Review of current value and modeled pre-tax and after-tax outcomes
- Coordination with your tax preparer on ordinary income, capital gains, and AMT
- Scenario analysis on upside, downside, and tax consequences
- A plan for how many options to exercise, which grants, and when
- Strategies to diversify concentrated positions and manage liquidity needs
- 10b5-1 education and coordination where appropriate
- Post-lockup implementation of sale strategy and long-term portfolio design
Planning by Equity Type
RSUs and stock options require different decisions. We model both — always validated with your CPA.
- When to sell — vesting schedule, withholding, and post-vest concentration
- Withholding elections — what rate to select and cash-flow impact
- Scenario modeling — how price moves affect net proceeds and tax
- CPA collaboration — ordinary income timing and estimated payments
- Post-liquidity plan — reinvestment and diversification after lockup
- When and how much to exercise — spread across tax years where possible
- AMT modeling — ISO exercise impact and credit carryforward planning
- Cashless vs cash exercise — funding the exercise and tax bill
- Early exercise & 83(b) — coordination with your tax team on elections
- Lockup strategy — sale pacing during and after trading restrictions
Founder with QSBS or entity-level tax questions? See our Tax Planning page for pre-exit structure and Section 1202 coordination. For a full personal roadmap beyond equity, see Financial Planning.
Start Before the Lockup Clock Starts
The best time to plan is often 6–12 months before liquidity — or as soon as options are exercisable. We'll map your scenarios with your CPA so you decide from after-tax numbers, not headlines.
Clexperus does not provide tax preparation, legal advice, or securities law counsel. IPO and equity planning is coordinated in partnership with your CPA and legal advisors.
One Journey: Before, During, and After Liquidity
Whether your company has announced an IPO, is rumored to go public, or you just went through an acquisition — planning is one continuous arc. We help at every stage, including when no date has been set yet.
-
EARLY
Before a Date Is Set
Private secondaries, early exercise, 83(b) review, and scenario modeling while equity is still illiquid.
-
6–12 MO
Approaching the Event
Exercise strategy, AMT modeling, withholding, and 10b5-1 planning before shares are tradable.
-
LOCKUP
IPO & Restrictions
Cash needs, concentration risk, trading windows, and sale pacing during restrictions.
-
AFTER
Post-Liquidity
Diversification, investment strategy, and retirement, estate, and charitable alignment.
What You Can Expect From Clexperus
- Education on the types of equity you hold and how each is taxed
- Review of current value and modeled pre-tax and after-tax outcomes
- Coordination with your tax preparer on ordinary income, capital gains, and AMT
- Scenario analysis on upside, downside, and tax consequences
- A plan for how many options to exercise, which grants, and when
- Strategies to diversify concentrated positions and manage liquidity needs
- 10b5-1 education and coordination where appropriate
- Post-lockup implementation of sale strategy and long-term portfolio design
Planning by Equity Type
RSUs and stock options require different decisions. We model both — always validated with your CPA.
- When to sell — vesting schedule, withholding, and post-vest concentration
- Withholding elections — what rate to select and cash-flow impact
- Scenario modeling — how price moves affect net proceeds and tax
- CPA collaboration — ordinary income timing and estimated payments
- Post-liquidity plan — reinvestment and diversification after lockup
- When and how much to exercise — spread across tax years where possible
- AMT modeling — ISO exercise impact and credit carryforward planning
- Cashless vs cash exercise — funding the exercise and tax bill
- Early exercise & 83(b) — coordination with your tax team on elections
- Lockup strategy — sale pacing during and after trading restrictions
Founder with QSBS or entity-level tax questions? See our Tax Planning page for pre-exit structure and Section 1202 coordination. For a full personal roadmap beyond equity, see Financial Planning.
Start Before the Lockup Clock Starts
The best time to plan is often 6–12 months before liquidity — or as soon as options are exercisable. We'll map your scenarios with your CPA so you decide from after-tax numbers, not headlines.
Clexperus does not provide tax preparation, legal advice, or securities law counsel. IPO and equity planning is coordinated in partnership with your CPA and legal advisors.
Why Choose Clexperus for Pre & Post-IPO Planning
Before the lockup
The highest-leverage equity decisions happen before shares are freely tradable.
Exercise timing, withholding, AMT, and 10b5-1 planning — we model the trade-offs while you still have room to move.
The Lockup Playbook
Two windows, different levers. Before lockup ends, you plan for cash needs and concentration. After restrictions lift, you execute diversification and build the long-term portfolio. Waiting until the first day you can sell is the most expensive mistake we see.
- Exercise strategy — which grants, how much, and in which tax years (ISO/NSO/AMT modeling with CPA)
- Withholding elections — RSU vesting and supplemental rate choices before shares hit your account
- Cash-flow planning — liquidity for tax bills, living expenses, and major purchases while stock is restricted
- 10b5-1 setup — education and coordination for insiders subject to blackout windows
- Early exercise & 83(b) — review with tax team while elections are still available
- Private secondary review — scenario analysis if pre-IPO liquidity is an option
- Investment strategy draft — target allocation ready before the first allowed sale
- Sale strategy implementation — paced diversification aligned with trading windows and tax lots
- Tax-efficient diversification — charitable giving of appreciated stock, exchange funds, and other vehicles coordinated with CPA
- Concentrated stock management — hedging, covered calls, and risk limits where appropriate
- Proceeds deployment — cash, fixed income, and growth allocation tied to goals
- Retirement & estate alignment — beneficiary updates, gifting, and trust funding post-liquidity
- Estimated tax coordination — avoid surprises on the sale-year tax bill
- Ongoing review cadence — quarterly check-ins as concentration declines and plan evolves
Already past your IPO? We help more clients after liquidity than before. Post-event focus: secure the financial foundation, diversify tax-efficiently, and align proceeds with retirement, estate, and charitable goals — coordinated with your existing advisors.
Pre & Post-IPO Questions We Hear Often
Timing, equity types, and how Clexperus coordinates with your CPA through the full liquidity arc.
We typically recommend starting 6–12 months before an IPO or major liquidity event. If you have exercisable options, it can make sense to begin as soon as they are exercisable — that gives time to model cash flow, taxes, and investment strategy proactively.
Starting early helps you make informed decisions on exercise timing, withholding, and 10b5-1 planning before equity becomes freely tradable.
Yes. Planning early allows us to review your equity, explore private secondary market options where available, and build a long-term strategy. We help with tax-aware scenario modeling and cash-flow planning so you are in a stronger position once timelines become clearer.
CPA collaboration on after-tax proceeds, 83(b) election review, 10b5-1 education and coordination, lockup-period cash planning, and post-liquidity sale and diversification strategy. The goal is to turn concentrated equity into a long-term financial foundation — aligned with retirement, estate, and charitable goals.
Definitely. Many clients come to us after liquidity. Post-event focus: tax-efficient diversification, investment strategy, retirement planning, estate alignment, and charitable giving — coordinated with your CPA and counsel.
Pre & Post-IPO Planning focuses on the equity compensation and liquidity event journey — exercise, lockup, sale, and concentration. Financial Planning is the broader personal roadmap. Tax Planning owns entity structure, QSBS, and pre-exit tax architecture. We cross-link and coordinate across all three; your engagement depth depends on where you are in the timeline.
We educate and coordinate on 10b5-1 planning in partnership with your legal and compliance teams. Clexperus does not provide securities law counsel, tax preparation, or legal document drafting. We build the financial model and sale strategy; your attorneys and company counsel govern plan structure and compliance.
Next Steps: Plan Before the Window Closes
Whether your company is pre-IPO, in lockup, or post-liquidity — choose a time below. We’ll explore your equity picture and how coordinated planning fits with your CPA and advisory team.