Navigating Liquidity Events

Planning to sell?
Plan for new wealth.

The decisions you make today determine how much of your hard-earned value you keep tomorrow. The most valuable planning happens before the wire hits.

Executive office with city skyline - liquidity event planning

The Cost of Waiting

On a $75M exit, $30 million can walk out the door.

Most founders know taxes will take a bite. Few understand how large that bite actually is — or how much of it was avoidable.

The Unplanned Exit — $75M Gross

Federal long-term capital gains (20%)$15,000,000
Net Investment Income Tax (3.8%)$2,850,000
State tax — up to 13.3%$9,975,000
Transaction & advisory costs (~3%)$2,250,000
Total out the door$30,075,000
Net to founder~$45M

The Compounding Cost

The day-one tax loss is only part of the story. The real cost is what that $22.5 million would have become.

Two founders. Same $75M exit. Founder A kept $45M with no planning. Founder B kept $67.5M with proper pre-exit structuring.* Both deploy the same strategy after close.

Year 0 (Exit Day)$20.0M$42.5M$22.5M
Year 5$40.2M$85.5M$45.3M
Year 10$80.9M$171.9M$91.0M
UnplannedPlannedGap

"The tax bill wasn't $22.5 million. It was $91 million. You just didn't see all of it on closing day."

The Deadline No One Tells You About

The strategies that preserve $20–25 million of a typical exit are not new. They are provisions of the Internal Revenue Code that sophisticated tax counsel implements regularly. The problem is timing. Every one of them has an expiration date — and that date arrives before the closing.

24+ months

Full toolkit available

12–24 months

Most strategies open

6–12 months

Window narrowing

Post-close

Most options expired

Every month that passes, another strategy comes off the table.

*Tax and Estate planning services are provided in coordination with your legal and tax professionals. Tax and estate laws are subject to change, and results may vary and tax reduction is not guaranteed.

† The numbers displayed, projections, and growth scenarios shown above are hypothetical and illustrative in nature. They are based on assumed rates and do not in any way constitute a guarantee of that growth or outcome for your personal investment. Actual results will vary based on individual circumstances, tax rates, investment performance, and other factors.

Our Approach

Waiting until you exit to build a wealth plan introduces unnecessary tax and risk. We guide entrepreneurs through the pivotal decisions before, during, and after the sale.

01

Maximize after-tax proceeds*

Your structure determines your tax bill long before you sign. We evaluate alternative structures to minimize the tax liability from a sale, exploring tax-advantaged strategies, charitable structures, and entity design so you retain more of what you built.

  • QSBS and other tax-advantaged structures
  • Capital gains reduction strategies
  • Entity design for investor appeal and a smoother sale
02

Limit transfer taxes

By planning ahead, you can shift future appreciation off your balance sheet. We help you structure legacy trusts to protect your assets and effectively freeze value ahead of the transaction, before the wire ever hits.

  • Dynasty, GRAT, and asset-protection trusts
  • Pre-transaction gifting and freeze strategies
  • Coordination with your estate counsel
03

Reduce risk from concentrated equity

Concentrated equity builds wealth. Diversification maintains it. After a sale, we optimize your portfolio for risk-adjusted returns, transitioning your wealth into a stable, long-term foundation engineered to last.

  • Diversification away from single-stock exposure
  • Full-cycle, drawdown-aware portfolio design
  • Liquidity planning for lifestyle and reinvestment
Before the wire

The best time to plan was a year ago. The second best is now.

If a sale is on your horizon, an early conversation is the single highest-leverage decision you can make.