A Windfall Can Transform Your Life. The Wrong Moves Can Unravel It.
Guide to Selling a Business, Exit Tax Strategy, Liquidity Planning, and Wealth Management Before a Company Sale, IPO, or Acquisition
Your business built your wealth. The Liquidity Event Playbook maps the planning questions and timing windows that shape what you keep, before the terms are ever signed.
A free, educational guide for business owners, founders, executives, and early employees approaching a sale, IPO, or other liquidity event.
Inside the 2026 edition:
- The five common, costly mistakes founders make around a liquidity event
- Tax, investment, and estate moves to make before and after – mapped by event type
- A pre- and post-liquidity checklist to start using now
- Why many high-value decisions happen before the funds arrive
Download the Liquidity Event Playbook for Free
It’s free. We respect your inbox, keep your information private, and you can unsubscribe at any time.
What's Inside the Playbook
Inside, you’ll uncover:
- Pitfalls by liquidity event type. The tax and wealth traps that show up around each kind of liquidity event, and what to weigh before you reach them.
- Five costly mistakes. The recurring errors that surface again and again, framed so you can recognize them early.
- Tax, investment, and estate considerations. How the pieces connect, and why the order you address them in matters.
- A pre and post-liquidity checklist. A practical way to organize the months before and after your event.
Six liquidity event types we address:
- IPO
- Company sale
- Secondary sale
- ISO exercise window
- Acquisition
- Tender offer or share buyback
This guide has been updated for the 2025 tax-law changes that affect liquidity events. Tax laws are complex and subject to change, and the right treatment depends on your circumstances, so the playbook points you toward qualified tax professionals rather than a one-size answer.
Why Certuity?
Certuity is a wealth management firm built by entrepreneurs, for entrepreneurs. The firm is experienced in guiding founders, executives, and families through liquidity events. We coordinate the tax, investment, estate, and legacy decisions that a windfall sets in motion.Â
As fiduciaries, Certuity has a duty to act in its clients’ best interests. We work from a comprehensive understanding of their situation toward the goals that matter most to them. This guide reflects that approach: educational first, and tailored to your circumstances when the time comes for a conversation.
Want to unlock the full guide?
Liquidity Event Planning: Common Questions
Who is this guide for?
Founders and business owners with a pending or recent exit as well as executives and early employees approaching an IPO, acquisition, secondary sale, tender offer, or buyback. If a liquidity event is on your horizon, this applies to you.
Can Certuity talk through your specific situation?
Yes. When you are ready, Certuity’s advisors can discuss your circumstances and how a coordinated plan might fit your goals. The guide is a place to start, not a commitment.
When should I start planning for a liquidity event?
Six to twelve months before you expect liquidity. Most high-value tax, investment, and estate strategies — QSBS confirmation, pre-sale gifting into trusts, donor-advised fund contributions, entity and deal structuring — must be executed before the deal is signed. After closing, the remaining options are largely limited to diversification, tax-loss harvesting, and estimated tax management.
What is QSBS and how did it change in 2025?
Qualified Small Business Stock (Section 1202) allows eligible shareholders to exclude capital gains on qualifying stock. For stock acquired after July 4, 2025, the exclusion became tiered: 50% of eligible gain at a three-year hold, 75% at four years, and 100% at five years. The per-issuer cap rose from $10M to $15M and the company gross-assets ceiling rose from $50M to $75M. Stock acquired on or before July 4, 2025 remains under the prior rules, so confirming which set applies is a first-order question.
What are common mistakes people make after a liquidity event?
Common mistakes include waiting too long to plan, mistiming the share sale, underestimating the combined tax burden across federal, AMT, state, and net investment income tax, holding too much company stock out of loyalty or inertia, and lifestyle creep in the absence of a spending framework.
How much company stock is too much after an IPO?
There’s no universal number — it depends on your total balance sheet, time horizon, and how much of your future income also depends on the company. What’s consistent is that a concentrated position magnifies both gains and losses, and unwinding it thoughtfully through staged approaches like 10b5-1 plans, exchange funds, or tax-loss harvesting generally produces a better after-tax result than either holding indefinitely or selling all at once.
Does a business sale trigger estate tax exposure?
Often, yes, and for many owners it’s the first time. Wealth that sat illiquid and hard to value for years converts to cash at a clear number. With the federal exemption at $15M per person and $30M per married couple for 2026, a mid-eight-figure sale can push a family past the threshold. Transfer techniques generally work best before the sale, while share values are lower.
What’s the difference between planning for a secondary sale and a full exit?
A secondary provides partial liquidity without a formal exit, usually at a discount to the eventual exit price. The core question is sizing: how much to sell relative to your remaining upside, and whether the shares qualify for QSBS treatment. A full exit converts the entire position at once, which makes deal structure, purchase price allocation, and installment treatment the dominant variables.
Do I need a financial advisor for an exit, or is a CPA enough?
A CPA handles tax compliance and often tax strategy. A liquidity event also raises portfolio construction, concentration risk, estate and asset protection, and long-term spending questions that sit outside a tax return. The strongest outcomes usually come from having those functions coordinated rather than sequenced after the fact.