Exit & Capital Events

Get the numbers exit-ready before the buyer does.

Most sellers discover the EBITDA haircut in week six of diligence, when it is too late to fix and only time to negotiate against. The work is to find it first. Exit-preparation CFO advisory from someone who has sat on the operator's side of a $95M sale.

$95M
Sale of Medicx Health to OptimizeRx (NASDAQ: OPRX), October 2023
$15–40M
Revenue scaled from a declining base through stabilization and growth
20%+
EBITDA margin, built from break-even post-stabilization
25+
Years in operating finance across healthcare, PBM, tech, and services
High-Stakes Window

The gap between your EBITDA and theirs.

Every founder has a number in their head for what the business earns. A buyer's quality-of-earnings team has a different number, and theirs is the one that sets the price. The distance between the two is where exits get won or lost. Customer concentration, contract durability, working-capital normalization, add-back defensibility, and revenue-recognition cleanliness all move that number, and most sellers learn about it during diligence... after the deal terms are set and the leverage has shifted to the buyer.

Exit preparation is the discipline of closing that gap before the process starts. Done early, it is a value-creation lever. Done late, it is damage control. The difference in proceeds can be larger than a full year of operating profit.

I led Medicx Health through a $95M sale to OptimizeRx in 2023. I have prepared the numbers, sat through the diligence, and seen exactly where the haircuts come from.

What exit preparation covers

  • Quality-of-earnings readiness. Building EBITDA the way a buyer's QofE team will rebuild it, so there are no surprises when they do.
  • Add-back defensibility. Separating the add-backs that survive diligence from the ones that quietly disappear and take enterprise value with them.
  • Customer and contract analysis. Concentration, churn, and contract durability framed honestly, with the risks addressed before a buyer raises them.
  • Working-capital normalization. Establishing the peg before the buyer proposes one, so the closing adjustment does not erode proceeds.
  • The financial narrative. A data room and a story that hold up to PE and strategic diligence, presented from strength rather than reconstructed under pressure.

Timing it right

The best exit work starts 12 to 36 months before a process, not 12 weeks. That runway is what lets you actually fix concentration, clean up revenue recognition, and build a track record of defensible margin rather than just describing your intentions to a skeptical buyer. If the timeline is shorter, the work shifts toward triage... finding the largest risks and getting ahead of the ones that can still be managed.

Engagements here range from a focused project SOW to a Board-Ready or Acting CFO retainer through the transaction itself. The right structure depends on how far out the event is and how much lift the internal team needs.

Not sure of the timeline?

A Pulse Check is a clean way to get an early read. Thirty days, fixed fee, a structured diagnostic on cash, margin, and KPI maturity, and an honest assessment of how far the numbers are from exit-ready. It surfaces the work that matters before you commit to a full engagement or a process.

Common Questions

Answers before the call.

The questions that come up first when a founder or sponsor is sizing up the fit.

When should exit preparation actually start?+
Ideally 12 to 36 months before a sale process. That runway lets you fix real issues like customer concentration and revenue-recognition cleanliness rather than just describe intentions to a buyer. Shorter timelines shift the work toward triage on the largest risks.
What is the most common reason sellers lose value in diligence?+
The gap between management EBITDA and quality-of-earnings-grade EBITDA. Add-backs that do not survive scrutiny, undisclosed customer concentration, and working-capital surprises are the usual culprits, and they tend to surface in week six when leverage has already shifted to the buyer.
Have you actually been through a sale?+
Yes, on the operator's side. I led Medicx Health through diligence and a $95M sale to OptimizeRx, a public company, in October 2023. The exit-prep work is built from having done it, not from advising on it from the outside.
Do you replace the investment banker or M&A advisor?+
No. The banker runs the process and the market. My role is sell-side financial readiness: making sure the numbers, the add-backs, and the narrative are defensible before and during diligence, working alongside the banker and counsel.
How do exit-prep engagements get structured?+
From a focused project scope to a Board-Ready or Acting CFO retainer through close, depending on timeline and internal team capacity. A 30-day Pulse Check is available as an early diagnostic to size the gap before committing.
Next Step

Find the haircut before the buyer does.

If an exit or capital event is anywhere on the horizon, an early conversation is the cheapest insurance you can buy on the proceeds.