By Invitation | Pre-Exit Planning Sprint

The deal is the easy part.The day after is the hard part.

A private, tax-aware, pre-exit planning sprint for founders preparing for a sale, recap, or major liquidity event, designed to reduce surprises and keep you in control of the day after.

Deal timelines compress fast. We help you get ahead of taxes, structure, and personal planning before the LOI arrives.

A Diagnostic

If an LOI showed up in the next 30 to 90 days, would you know:

  • 01What you keep after taxes under 2-3 realistic deal structures?
  • 02What "enough" means for you (post-tax number + lifestyle + legacy)?
  • 03What the first 90 days after close should look like, cash, diversification, and decision rules?

If those questions create even a hint of decision fatigue, this sprint is built for you.

What Happens in the Sprint

Three deliverables. One coordinated process.

This is not a generic financial plan. It is a focused readiness process that produces clarity and an execution checklist.

01

Scenario Map

Net proceeds under 2-3 structures with clear, documented assumptions. Asset vs. stock vs. recap/rollover/earnout, modeled side-by-side so you can see the tax delta before you negotiate.

02

Pre-Close Checklist

Tax, balance sheet, estate, and risk items, each with an owner and a deadline. The things that need to happen before the wire hits, not after.

03

Post-Close 90-Day Plan

How cash is managed the moment it lands, what gets invested versus held, and how concentrated risk is diversified in a tax-aware sequence. The plan you wish you had built before the deal closed.

The Scope

Eight readiness areas, covered without gaps.

Each one has caused real founders real pain. Each one gets a concrete answer before the wire hits.

01

Clarity

Define "enough," timeline, and your top deal non-negotiables.

02

Tax + Deal Structure

Asset vs. stock vs. recap / rollover / earnout. QSBS review, state exposure, timing risks.

03

Personal Balance Sheet

One-page view of assets, liabilities, entities, and key accounts. Liquidity runway and concentration flags.

04

Post-Close Transition

First-90-days cash plan, decision rules, and a diversification plan for concentrated positions.

05

Estate + Family Alignment

Wills, trusts, POAs. Beneficiary alignment, philanthropic intent and timing.

06

Risk + Protection

Liability and umbrella coverage, entity-level protection, key-person, disability, life. Cyber and wire controls.

07

Your Team + Process

Identify your core advisors, assign a quarterback, owners and deadlines for every pre-close action.

08

Identity + Purpose

Who you are when you are no longer the founder. The conversation few advisors have, and the one that determines whether the day after feels like freedom or like loss.

What You Leave With

Four documents you can actually use.

  • A 1-page Liquidity Event Readiness Scorecard (risks, priorities, and next steps).
  • A net-proceeds scenario summary (2-3 structures) with assumptions clearly documented.
  • A 90-day post-close transition plan (cash + investing + diversification) aligned with your tax picture.
  • An execution checklist with owners, deadlines, and a coordination cadence with your CPA and attorney.
Who This Is For

Built for a particular kind of founder.

A strong fit

Probably not a fit

Business owners and founders with $5MM+ in investable assets or meaningful liquidity at stake
You already have all the answers and want an advisor to nod
A potential sale or recap in the next 6-24 months
You see planning as a cost to minimize, not insurance against seven-figure mistakes downstream
You value clarity, coordination, and implementation
You are “too busy” for the planning that surrounds the largest financial event of your life
You are coachable and open to being challenged
You are not fully committed to a world-class exit; hoping it works is the strategy
Sprint FAQ

A few things founders ask first.

How long does the sprint take?

Typically 2-3 weeks end-to-end.

How much does this cost?

It is not cheap, and it should not be. The Sprint requires senior, transaction-experienced thinking, and we do not do that work for free. We quote the engagement transparently once we understand your situation.

What is far more expensive is the cost of getting the deal wrong: a poorly chosen structure, a missed QSBS election, a tax surprise, or a post-close transition that wastes the first eighteen months of your optionality. Those mistakes routinely cost founders multiples of what disciplined pre-exit planning would have cost.

The Sprint is priced to be a fraction of the value it protects.

Do you work with my M&A attorney or banker?

Yes. We coordinate around tax, personal balance sheet, and post-close planning while your deal team runs the transaction.

Is this tax or legal advice?

No. We collaborate with your CPA and attorney and document assumptions so decisions are made deliberately.

Frequently asked questions

What is pre-exit (liquidity) planning?
Pre-exit planning is the work you do before a sale or transition closes to protect and organize the wealth the exit will create. It maps your after-tax proceeds, coordinates deal structure with your tax and legal advisors, and prepares your personal balance sheet, estate plan, and cash-flow plan so the liquidity event does not catch you unprepared. The highest-value moves happen before the deal closes, not after.
When should I start planning for a business exit?
Ideally one to three years before you expect to sell, and no later than when a letter of intent is on the table. Many of the most valuable steps, such as entity and deal structuring, gifting ahead of a valuation increase, and QSBS qualification, need to be in place well before closing. Starting early widens your options; starting at closing narrows them to whatever is left.
What does the Exit Planning Readiness Sprint cover?
It is a focused engagement that produces three things: a scenario map of your after-tax outcomes under different deal terms, a pre-close checklist coordinated with your CPA and attorney, and a post-close 90-day plan for the proceeds. It spans deal and tax structure, your personal balance sheet, estate and family alignment, risk, and the identity questions that often follow a sale.
How do you help reduce the taxes on a sale?
We coordinate with your CPA and deal attorney to align entity structure, deal terms, timing, and any gifting or charitable strategies before the transaction closes, using established provisions of the tax code. The aim is to help you keep more of the proceeds through disciplined, defensible structuring. Whitwell does not file your return or draft legal documents; we build and coordinate the plan around the professionals who do.
What happens to the money after the sale?
A liquidity event turns one concentrated asset into investable capital, which calls for a deliberate plan rather than a rushed one. We help you set a post-close cash-flow and investment framework, address estate and family goals, and avoid the common mistake of committing the proceeds before the plan is set. The first ninety days matter, and so does resisting pressure to move quickly.
By Invitation

Apply for a Liquidity Event Readiness Sprint.

Designed for $5MM+ founders who want to reduce surprises, protect what they have built, and move into the next chapter with confidence. We do not believe in pressure or hard pitches. We believe in the right relationship with the right people at the right time.

Apply for the SprintTake the Scorecard First

For educational and informational purposes only. Not individualized investment, legal, tax, or accounting advice. Consult your attorneys and CPAs regarding your specific situation.