Exit Readiness: The Financial Work You Should Start 24 Months Before You Sell

Exit Readiness: The Financial Work You Should Start 24 Months Before You Sell | Gregg Carlson
March 2026
Exit Planning  ·  M&A Readiness  ·  Valuation  ·  Due Diligence

Exit Readiness: The Financial Work You Should Start 24 Months Before You Sell

AUTHOR
Gregg Carlson
Gregg Carlson
Fractional CFO & Controller  ·  CPA (inactive)  ·  gregg-carlson.com
25+ years  ·  $700M+ in transaction experience  ·  $17M business sale lead  ·  $290M acquisition audit
Companion Article

This article is an extension of “Why Most Private Company Sales Stall or Get Discounted — And How to Make Sure Yours Does Not,” published March 1, 2026. Where that article examined the financial mechanisms buyers use to reduce price — Quality of Earnings adjustments, working capital pegs, and earnout structures — and the sell-side playbook for countering them, this article provides the detailed 24-month financial preparation timeline that makes that playbook executable. Reading both articles together gives owners the complete picture: what buyers will do to your price, and how to prepare so they cannot. Both articles are recommended for any owner considering a sale within the next 24–36 months.

Important Disclosure

This article is for general informational and educational purposes only and does not constitute investment, financial, legal, tax, accounting, valuation, M&A advisory, or any other form of professional advice. No professional advisory relationship, fiduciary duty, or duty of care is created by reading it. The author is not a registered investment adviser, registered broker-dealer, licensed securities professional, or licensed M&A intermediary. Valuation multiples, due diligence timelines, transaction outcomes, and QoE adjustment ranges described herein are general market estimates and practitioner observations only; actual outcomes vary materially by industry, business size, financial quality, buyer type, market conditions, and transaction structure. Nothing herein should be relied upon as a basis for any business, financial, legal, or investment decision without independent professional advice. See full disclosure at the end of this article. © 2026 Gregg Carlson Financial Advisory.

Key Takeaways — 60-Second Read
  • The most expensive mistakes in a business sale are made long before the sale process begins — typically 24–36 months before a letter of intent is signed.
  • Buyers do not pay for what your business earned last year. They pay for what they believe it will earn going forward — and their confidence in that belief is determined by the quality of your financial data.
  • A Quality of Earnings (QoE) analysis is the single most consequential financial document in an M&A process. Understanding what it examines — and preparing for it — is the most valuable use of your pre-sale preparation time.
  • AI-assisted financial reporting is now a component of exit preparation. Buyers and institutional lenders are beginning to evaluate financial data infrastructure as part of due diligence.
  • Owner dependency is the most common valuation killer in lower middle market transactions. Every dollar of EBITDA that requires the owner’s presence to produce is a dollar buyers will discount.
  • The 24-month preparation window is the minimum time required to address the financial, operational, and governance issues that will otherwise surface during due diligence and cost you money.
KEY DATA
24Months minimum preparation time before a sale — the window where financial work creates value
3.7xMedian private company EBITDA multiple, all industries, Q1 2025 — DealStats Value Index
30–60Days typical due diligence window — time kills deals; prepared sellers close faster
5Years of financial statements, tax returns, and bank records buyers typically request in due diligence
Why 24 months
Why Preparation Must Start 24 Months Before You Sell

As explored in the companion article published March 1, 2026 — “Why Most Private Company Sales Stall or Get Discounted” — the structural reasons deals fail are well-documented: owner dependency, undisclosed liabilities, non-assignable contracts, and financial records that cannot survive scrutiny. This article focuses on the upstream work: the specific financial preparation that must begin 24 months before a transaction process starts in order to address those structural issues while there is still time to fix them, not merely disclose them.

Most business owners think about exit preparation the way they think about selling a house: clean things up, price it right, and find a buyer. The analogy fails in one critical respect. A house buyer does not have access to five years of your tax returns, three years of financial statements, your payroll records, your customer contracts, your key-person insurance, your lease agreements, and your accounts receivable aging schedule. A business buyer does. And what they find — and how long it takes to find it — determines whether your deal closes at the price you expected, at a reduced price, on a delayed timeline, or not at all.

The 24-month window is the minimum time required to address three categories of financial issues that consistently surface in due diligence:

Accounting quality issues that take 12–18 months to cure. Clean financial statements with consistent accounting policies, normalized owner compensation, and no material restatements take time to produce. You cannot manufacture three years of clean financials in three months. Buyers pay for a track record, not a promise.

Operational dependencies that take 12–24 months to restructure. If your business cannot operate without you, buyers will discount it or require an earnout. Transitioning from owner-operator to management-led operation is a multi-year project that cannot be compressed into a sale timeline.

Legal and structural issues that take 6–18 months to resolve. Customer contracts without assignability clauses, leases requiring landlord consent, personal guarantees that must be unwound — each is a potential deal delay or deal-killer that a qualified advisor can fix in advance but not during a process.

The Most Common Mistake: Starting Too Late

The most significant error for most small and mid-sized business owners is not delaying the sale itself — it is postponing the preparation for it. Owners who begin working with an M&A advisor or fractional CFO six months before they want to sell discover that the issues that will cost them money have been compounding for years. The owner who begins 24 months out has time to fix them. The owner who begins six months out has time to disclose them — and watch the buyer use them to negotiate a lower price.

In my experience advising and leading transactions totaling more than $700M — including serving as finance lead on a $17M business sale and preparing financial statements for a $290M acquisition audit — the quality of a seller’s financial preparation is the single most consistent predictor of deal outcome. Not the business model. Not the market. The preparation.

Bottom line

Buyers pay for verified, consistent, forward-looking earnings. The 24-month window exists to build the financial record and operational foundation that makes your earnings verifiable, consistent, and believable to a sophisticated buyer.

What buyers examine
What Buyers and Institutional Investors Actually Examine in Due Diligence

Due diligence requests from serious buyers typically fall into four broad categories. Understanding each allows a seller to anticipate requests, prepare documentation, and avoid the deal-slowing delays that result from being caught without basic financial records.

Figure 1 — The Four Categories of M&A Due Diligence
What Buyers Request, Why They Request It, and What Red Flags They Are Looking For
CategoryWhat is requestedWhat the buyer is assessingCommon red flags
Financial5 years of financial statements, tax returns, bank statements, AR/AP aging, debt schedules, monthly management reports, projectionsQuality and sustainability of earnings; accuracy of reported profitability; working capital requirements; cash conversion; debt structureInconsistent accounting policies year-to-year; material differences between tax returns and financial statements; deteriorating AR aging; undisclosed liabilities
OperationalCustomer and supplier contracts; top customer revenue concentration; employee records; key-person dependencies; org chart; process documentation; IP ownershipBusiness transferability; customer concentration risk; key-person risk; operational scalability without the owner; competitive moat durabilityTop customer >20% of revenue; no written contracts with key customers; owner doing all selling; critical processes undocumented; key employees at-will with no retention plan
LegalEntity formation documents; all material contracts with assignability provisions; litigation history; regulatory compliance; IP ownership; real estate leases; personal guarantee schedulesLegal transferability of contracts; existing or contingent liability; regulatory exposure; clear IP ownership; lease terms and assignment rightsCustomer contracts requiring consent to assign; pending litigation; lease expiring during deal process; personal assets commingled with business; IP owned by individual rather than entity
Strategic & ManagementManagement team backgrounds; succession plan; competitive landscape analysis; customer references; growth plan; market positioningManagement depth beyond the owner; credibility of growth projections; competitive defensibility; ability to operate independently post-acquisitionNo management team beyond the owner; growth projections unsupported by data; customer references unavailable; business undifferentiated from competitors
Private Equity / Financial Buyer

Primary focus: Consistent, normalized EBITDA; management team that can operate independently; credible path to EBITDA growth post-acquisition; clean debt structure.

What will kill the deal: Owner dependency; customer concentration; weak management team; EBITDA that is not reproducible after removing owner-specific costs; legal contingencies creating uncertain post-close liability.

Strategic / Corporate Buyer

Primary focus: Synergy value — what your customer relationships, technology, team, or market position adds to their existing platform; integration risk and timeline.

What will kill the deal: Customer or supplier contracts that are not assignable; IT systems that cannot be integrated; regulatory issues that would contaminate the acquirer’s operations; undisclosed employee or IP disputes.

Bottom line

The due diligence process is a systematic examination of every assumption in your asking price. The seller who has prepared their documentation in advance controls the tempo of the process. The seller who has not hands that control to the buyer — and buyers use it.

Quality of Earnings
The Quality of Earnings Analysis: What It Is and Why It Is the Most Important Financial Document in Your Sale

The companion article published March 1, 2026 identified the QoE as one of the three primary financial tools buyers use to reduce your price after the LOI is signed — alongside the working capital peg and the earnout structure. That article addressed what the QoE does to sellers who are unprepared for it. This section focuses on how to prepare for it so it cannot be used against you.

The Quality of Earnings (QoE) analysis is the financial due diligence report that every serious buyer commissions before closing a transaction. It is designed to answer one question: is the EBITDA the seller is claiming actually the EBITDA the buyer will own after closing?

The QoE typically includes: normalization of owner compensation to a market-rate equivalent; removal of one-time, non-recurring, and non-operating items; analysis of revenue recognition timing; review of related-party transactions and personal expenses run through the business; analysis of customer concentration and revenue sustainability; working capital peg analysis; and quality assessment of the accounting records themselves.

The QoE Is Not Optional for Buyers — and Sellers Who Understand It Have a Significant Advantage

The standard post-LOI sequence in lower middle market transactions: buyer signs LOI at a price based on seller’s reported EBITDA, commissions a QoE, discovers normalization adjustments that reduce adjusted EBITDA, and uses those adjustments to renegotiate the price downward. This sequence is so common in M&A practice it is sometimes called “price chipping.” The remedy is not to prevent the QoE — you cannot. It is to conduct your own internal QoE-equivalent analysis before going to market, so you know exactly which adjustments the buyer will find and can price them into your asking price rather than having them used against you.

Figure 2 — Common QoE Adjustments and Their Impact on EBITDA
How Quality of Earnings Normalization Adjustments Typically Affect Reported EBITDA
Adjustment TypeWhat the QoE examinesTypical direction & impact
Owner compensation normalizationReplaces actual owner salary and benefits with a market-rate equivalent management cost. Common in owner-operated businesses where owner is significantly over- or under-compensated relative to market.Can add or subtract 5–25% of reported EBITDA depending on how far owner comp deviates from market rate.
Non-recurring itemsIdentifies one-time expenses or revenues that will not recur: legal settlements, insurance proceeds, one-time project revenue, non-cash gains, PPP loan forgiveness.Adjustments in either direction. Non-recurring expenses increase adjusted EBITDA; non-recurring revenue reduces it.
Personal expenses through the businessIdentifies expenses benefiting the owner personally: personal vehicles, travel, club memberships, family compensation not tied to business roles, personal insurance, entertainment.Typically adds back to EBITDA. Buyers view as owner benefit that will not continue post-acquisition.
Revenue recognition timingVerifies that revenues are recognized when earned, not when billed or collected. Examines deferred revenue, advance payments, and any aggressive pull-forward of future period revenue.Can significantly reduce adjusted EBITDA if revenue pull-forward is discovered. One of the most damaging QoE findings for a seller.
Customer concentrationIdentifies revenue dependency on any customer representing more than 10–20% of total revenue. Risk-adjusts earnings sustainability.Applied as a discount to valuation multiple rather than an EBITDA adjustment. Concentration >20% in a single customer is a material valuation risk factor.
Working capital pegDetermines the “normal” working capital the business requires for ongoing operations. Establishes target working capital at close; shortfalls become a purchase price adjustment.Direct dollar-for-dollar purchase price adjustment if actual working capital at close is below the agreed peg. One of the most common sources of post-LOI disputes.
Source: Author analysis based on 25+ years of M&A transaction experience and general lower middle market M&A practice. The adjustment types and impact ranges shown are illustrative estimates only; actual QoE adjustments depend on the specific business, its accounting practices, industry, buyer analytical framework, and the QoE firm engaged. QoE findings in any specific transaction may be materially different from the general ranges shown. This table does not constitute financial, accounting, valuation, or M&A advisory advice. Engage qualified professionals before making any decisions based on this information.
Bottom line

Run your own internal QoE before going to market. Identify every adjustment a buyer’s QoE firm is likely to find. Price accordingly. This single step, properly executed 18–24 months before a sale, eliminates the most common source of post-LOI price reduction and deal failure in the lower middle market.

Valuation multiples
The Financial Metrics That Determine Your Valuation Multiple

Your business is worth a multiple of its normalized EBITDA. The complexity lies in three questions: What is your actual normalized EBITDA after QoE adjustments? What multiple applies to your business? And what financial characteristics cause that multiple to expand or compress?

Figure 3 — Private Company EBITDA Multiples by Size (2025–2026)
Lower Middle Market EBITDA Multiples: Current Market Estimates by Business Size — Quality vs. Discount Range
Typical range for well-prepared, quality businesses
Discount range for underprepared or distressed sellers
Micro (<$500K EBITDA)
Individual / SBA buyers
2–4x
1–2x
2–4x
Small ($500K–$2M EBITDA)
Strategic + smaller PE
3–6x
2–3x
3–6x
Lower Middle Market ($2M–$10M EBITDA)
PE firms, family offices
5–8x
3–5x
5–8x
Mid-Market ($10M+ EBITDA)
Institutional PE, corporates
7–12x+
5–7x
7–12x
Sources: Author analysis; DealStats Value Index Q1 2025 (all-industry median 3.7x EBITDA per Kreischer Miller reporting); GF Data 2025 (average 7.2x TEV/EBITDA for PE-backed transactions per Forvis Mazars reporting). All figures are general market estimates based on reported transaction data; actual multiples for any specific business vary significantly by industry, growth rate, EBITDA margin, customer concentration, management depth, revenue quality, and competitive buyer dynamics. These ranges are illustrative starting points only. Do not use these figures as a valuation for any specific business without independent analysis by a qualified business valuation professional. Business valuation is a complex, judgment-intensive discipline requiring analysis of facts specific to each company.
The Eight Factors That Expand or Compress Your Multiple
Figure 4 — Multiple Expansion vs. Compression Factors
What Moves Your EBITDA Multiple Within the Range — Addressable vs. Structural
FactorMultiple expansion (premium)Multiple compression (discount)Addressable in 24 months?
Earnings quality & consistency3–5 years of audited or reviewed financials; consistent growth; no material restatementsCompilation-only financials; inconsistent policies; large year-to-year varianceYes
Owner dependencyStrong management team; business operates without owner; documented processesOwner is sole revenue generator, key relationship, or decision-makerPartially — requires 18–24 months minimum
Revenue visibility & recurrenceRecurring revenue with contracts; low churn; diversified customer baseProject-based revenue; high customer concentration; no written contractsPartially — can improve diversification but not change model
Margin profile & trendStable or expanding EBITDA margins; gross margin above industry medianDeclining margins; cost structure dependent on ownerYes — AI and operational improvements can improve margins
Financial data infrastructureReal-time reporting; AI-assisted bookkeeping; clean audit trail; management reports on demandManual processes; delayed close; no management reporting; data not AI-readyYes — 12–18 months of AI implementation
Growth trajectoryConsistent revenue and EBITDA growth over 3+ years; credible growth plan with supporting dataFlat or declining revenue; growth dependent on one key customerPartially — requires authentic operational improvement
Legal & contractual cleannessAll material contracts assignable; no pending litigation; clean IP ownershipNon-assignable contracts; personal commingling; litigation exposureYes — with qualified legal counsel and 12–18 month runway
Industry and competitive positionFavorable industry tailwinds; defensible market position; differentiated product or serviceCommoditized offering; competitive headwinds; no pricing powerStructural — not addressable through financial preparation alone
Bottom line

Six of the eight multiple-expansion factors are directly addressable through disciplined financial and operational preparation within a 24-month window. The businesses that achieve premium multiples are not fundamentally different businesses. They are the same businesses, but prepared.

24-month timeline
The 24-Month Exit Preparation Timeline
Figure 5 — The 24-Month Preparation Timeline
Exit Readiness Preparation: Milestones, Priorities & Actions
Months 24–18
Foundation: Assemble the Team & Diagnose the Business Engage an M&A advisor or fractional CFO to lead the preparation process. Commission an internal QoE equivalent — understand exactly what a buyer’s QoE will find before the buyer does. Conduct a legal audit: review all material contracts for assignability clauses, audit entity structure for commingling, identify equity issues. Begin transitioning from owner-operated to management-led: hire or promote management, begin documenting processes and key relationships. Implement AI-assisted accounting: clean up chart of accounts, automate AP/AR, standardize financial reporting.
Critical
Months 18–12
Earnings Quality: Build the Financial Record Buyers Will Buy Engage CPA firm for reviewed or audited financial statements. Normalize owner compensation to market rate and document the adjustment. Remove personal expenses from business books going forward — create a clean year of financials. Address customer concentration: actively develop new customers to reduce single-customer exposure below 20% if possible. Resolve accounting policy inconsistencies. Build a rolling 13-week cash flow forecast and automated management reporting package.
High Priority
Months 12–6
Operational Readiness: Build the Management Infrastructure Buyers Are Paying For Confirm management team can operate the business independently for 30–60 days without the owner. Document all customer relationships, supplier contracts, and key operational processes in transferable format. Complete legal cleanup: ensure all material contracts are assignable, resolve lease extension or assignment issues, clear outstanding litigation. Begin organizing the data room: compile 5 years of financial statements, tax returns, bank statements, contracts, and HR records. Update financial projections with a 3-year plan supported by specific, verifiable assumptions.
Active Prep
Months 6–0
Go-to-Market Readiness: Prepare the Narrative, Position for the Right Buyers Finalize the Confidential Information Memorandum (CIM) with your M&A advisor. Data room fully populated and organized. Management presentations rehearsed. Working capital peg analysis completed and documented. All QoE-equivalent adjustments identified and pre-disclosed in CIM financial summary. Most recent full-year financial statements reviewed or audited by CPA. Letter of Intent process begins.
Go-to-Market
AI & exit value
How AI-Assisted Financial Reporting Builds Exit Value

The connection between AI implementation in the finance function and exit valuation is grounded in the specific things buyers examine during due diligence and the specific reasons they discount businesses that fall short. Every major area of due diligence focus — earnings quality, management depth, financial data infrastructure, reporting speed, and audit trail integrity — is directly improved by the AI implementation described in Article 05 of this series.

Figure 6 — AI Implementation and Exit Valuation: The Direct Connection
How AI-Assisted Finance Directly Addresses the Six Most Common Buyer Concerns in Due Diligence
Buyer concern: Earnings quality & audit trail

The problem: Buyers discount businesses where financial statements are assembled manually, accounting policies are inconsistent, and the audit trail between reported earnings and underlying transactions is unclear.

How AI addresses it: AI-assisted AP automation, bank reconciliation, and transaction classification creates a clean, consistent, auditable record of every financial event. QoE analysts examining an AI-assisted accounting system find cleaner records faster — reducing the probability of unfavorable discoveries and shortening due diligence timelines.

Buyer concern: Management depth without the owner

The problem: Buyers pay a premium for businesses that can operate independently of the owner. But management independence requires not just authority — it requires information tools to make decisions. A management team that depends on the owner to pull reports is not truly independent.

How AI addresses it: AI-powered dashboards, automated variance analysis, and natural language financial querying give the management team independent access to financial performance data. Buyers can see in due diligence that the team has the tools to run the business.

Buyer concern: Financial data infrastructure

The problem: Institutional buyers — particularly PE sponsors and family offices — are increasingly evaluating financial data infrastructure as a component of due diligence. A business requiring significant post-acquisition investment to reach institutional standard is priced accordingly.

How AI addresses it: Two years of AI-assisted bookkeeping, management reporting, and FP&A creates the institutional-grade financial infrastructure sophisticated buyers expect — visible in the data room through record consistency, reporting speed, and management information depth.

Buyer concern: Working capital normalization

The problem: The working capital peg is one of the most common sources of post-LOI disputes — covered in depth in the March 1 companion article, which described working capital adjustments as the “$5M–$15M surprise most owners never see coming.” Sellers who cannot demonstrate consistent, well-defined working capital patterns lose negotiating leverage on the peg.

How AI addresses it: AI-assisted AR/AP management and cash flow forecasting creates a clean, consistent, documented working capital pattern. The rolling cash flow forecast showing seasonal patterns, DSO trends, and DPO management is exactly the documentation needed to support a favorable working capital peg negotiation.

Buyer concern: Revenue sustainability

The problem: Buyers apply significant scrutiny to revenue sustainability — recurring revenue percentage, customer contract duration, churn rates. Businesses that cannot demonstrate customer revenue quality through financial data are discounted.

How AI addresses it: AI-driven customer profitability mining creates a granular, transaction-level view of revenue and margin by customer. This data, available in the data room, transforms a qualitative “our customers are loyal” claim into a quantified, auditable revenue quality analysis that supports the asking price.

Buyer concern: Post-acquisition scalability

The problem: Buyers are making a forward-looking investment. A business with manual, high-cost financial processes requires proportional cost increases as it grows — limiting the scalability thesis.

How AI addresses it: AI-assisted financial operations have near-zero marginal cost per additional transaction volume. A business that processes 100 invoices per month with AI processes 1,000 invoices per month with the same infrastructure — making the scalability story credible rather than aspirational.

Bottom line

In the context of exit preparation, AI implementation in the finance function is a valuation enhancement project. Every dollar invested in AI-assisted financial infrastructure in the 24 months before a sale reduces the probability of QoE-driven price reductions, shortens due diligence timelines, and builds the institutional-grade financial record that commands a premium multiple.

Five deal killers
The Five Deal Killers Found in Due Diligence — and How to Prevent Each One

The same five issues surface repeatedly in lower middle market due diligence and consistently damage or destroy deals. None of them are inevitable. All of them are addressable with sufficient preparation time.

Figure 7 — The Five Most Common Due Diligence Deal Killers
What Kills Lower Middle Market Deals — Root Causes, Financial Impact, and Prevention
Deal KillerHow it manifestsFinancial impactPrevention — start 24 months out
1. Owner dependencyManagement interviews reveal the owner handles all key customer relationships, pricing decisions, supplier negotiations, and strategic planning. No management team can describe operations without the owner present.Buyer requires multi-year earnout; reduces multiple by 1–3x; or walks away entirely if owner is unwilling to stay post-close.Begin systematic delegation 24 months out. Hire or promote a GM or COO. Document every key relationship. Transition customer relationships to the management team. Create a 90-day business continuity plan the owner is not in.
2. Customer concentrationRevenue analysis reveals one customer >20% of revenue, or three customers >50%. Buyer models the loss of the largest customer and decides the risk is unacceptable at the proposed price.Direct multiple compression; earnout provisions tied to retention of concentrated customers; price reduction equal to 1–2 years’ EBITDA of at-risk revenue; deal termination in extreme cases.Active customer diversification starting 24 months out. Set a target of reducing top-customer concentration below 20% before going to market. Every new customer won improves your valuation position.
3. Undisclosed liabilitiesLegal review reveals pending litigation; environmental exposure; undisclosed tax liabilities; personal guarantees creating post-close exposure; lease obligations not in disclosed financial statements.Dollar-for-dollar escrow or indemnity provisions; price holdbacks equal to estimated liability; deal termination if liability is material and unquantifiable.Legal audit 24 months out. Resolve outstanding litigation before going to market. Quantify all tax exposure with qualified counsel. Disclose everything — buyers who discover undisclosed liabilities lose confidence in everything else the seller has represented.
4. Non-assignable contractsLegal review reveals that key customer contracts, supplier agreements, government licenses, or real estate leases include anti-assignment clauses requiring third-party consent.Transaction timeline delayed 30–90 days; customer uses assignment request as leverage to renegotiate terms; deal structure changed to asset sale; deal failure if consent is refused.Contract audit 24 months out. Identify every agreement with an assignment restriction. Work with legal counsel to proactively obtain consent, renegotiate anti-assignment provisions, or restructure agreements before a buyer discovers them.
5. Financial record quality failureQoE analyst cannot reconcile reported financial statements to bank statements; finds material differences between tax returns and internal financials; discovers revenue recognition issues; cannot independently verify the reported EBITDA from underlying records.The most damaging discovery in due diligence. Beyond specific financial adjustments, it destroys buyer confidence in everything the seller has represented. Deals fail not because adjustments are unacceptable but because the buyer no longer trusts the seller.Engage a CPA firm for reviewed or audited financial statements starting 24 months out. Implement AI-assisted bookkeeping. Run a QoE equivalent internally. Reconcile tax returns to financial statements annually. Make your financial records the most credible thing in the data room.
Bottom line

Every one of these deal killers is discoverable with a proper pre-sale diagnostic. Every one of them is addressable with 18–24 months of preparation time. None of them require a fundamental change to your business model — they require disciplined execution of the financial and operational work that a qualified M&A advisor or fractional CFO can lead.

Action plan
Leadership Action Plan: Five Non-Negotiable Steps for Every Business Owner with a 24-Month Exit Horizon

Step 1: Engage a qualified M&A advisor or fractional CFO with transaction experience — now, not when you are ready to sell. Exit preparation is not a project an owner can manage alone while also running the business. A qualified advisor who has led transactions — not just analyzed them — knows exactly which issues will surface in due diligence and how to sequence the preparation work to maximum effect. Engage this person 24 months before your target sale date, not six months before.

Step 2: Commission an internal Quality of Earnings equivalent. Before you engage a buyer, engage a QoE-familiar CPA to identify every normalization adjustment a buyer’s QoE firm will find. Price those adjustments into your own understanding of what your business is worth. Prepare to disclose them proactively in your Confidential Information Memorandum rather than having them discovered. Sellers who disclose their own QoE adjustments proactively command more buyer confidence — and more negotiating leverage — than sellers who let buyers find them.

Step 3: Implement AI-assisted financial reporting and begin building 24 months of clean financial history. As described in Article 05 of this series, Phase 1 AI implementation typically costs approximately $200–$600 per month at current market pricing (verify with vendors before budgeting, as pricing varies by vendor, transaction volume, and integrations required) and delivers three directly exit-relevant outcomes: a clean, consistent, auditable transaction record; real-time financial visibility for the management team; and a cost structure that demonstrates operational scalability to buyers. Every month of AI-assisted financial history you accumulate before going to market is a month of institutional-grade evidence that your earnings are real and sustainable.

Step 4: Conduct a legal audit and resolve every contract assignability issue, entity structure issue, and contingent liability before engaging buyers. Hire qualified M&A legal counsel — not your general business attorney — to review every material contract, audit your entity structure, identify contingent liabilities, and create a remediation plan. Start 24 months out. Legal issues that take six months to resolve are manageable with 24 months of runway. They are deal-killers with three months.

Step 5: Begin the operational transition from owner-led to management-led — immediately. If your business cannot run without you for 90 days, buyers will price that risk into their offer or require a multi-year earnout. Begin the transition today: hire, train, delegate, document. Make yourself replaceable in every operational role. Buyers pay a premium for businesses that work without their owners. They should. So should you.

24Months minimum to address the financial, legal, and operational issues that consistently surface in due diligence
1–3xIllustrative EBITDA multiple range between a prepared and unprepared seller — author estimate based on practitioner experience; varies widely by industry and circumstances
5Years of clean financial records a serious buyer will request — start building that record now
Bottom line

Exit readiness is not a transaction strategy. It is a business management discipline. The owners who achieve premium multiples and clean closings are not the ones who got lucky with their buyers. They are the ones who spent 24 months building a business that a sophisticated buyer could verify, trust, and pay full price for. The work starts now. The closing happens in 24 months.

Work With Gregg Carlson

Is your business exit-ready? Let’s find out together.

Gregg Carlson provides fractional CFO and Controller services to SMBs preparing for a capital raise or sale. With $700M+ in transaction experience — including service as finance lead on a $17M business sale and financial statement preparation for a $290M acquisition audit — Gregg brings hands-on, responsible-for-the-numbers transaction experience to every engagement. If you would like a complimentary conversation about your exit readiness and what a 24-month preparation plan looks like for your specific situation, reach out directly.

Email Gregg gregg-carlson.com

Las Vegas, NV  ·  Domestic & International

Notes & Sources
  1. [1] All-industry private company median EBITDA multiple 3.7x (Q1 2025). DealStats Value Index, Q1 2025, as reported by Kreischer Miller, “Private Company M&A Trending Multiples through Q1 2025,” June 2025, kmco.com. Reflects median selling price per EBITDA across all private company transactions. Industry and size variation is significant.
  2. [2] PE-backed middle market average 7.2x TEV/EBITDA (YTD 2025). GF Data, as reported by Forvis Mazars, “Q2 2025 Middle-Market M&A Insights,” September 2025, forvismazars.us. Reflects PE-backed transactions specifically; non-PE transactions typically trade at lower multiples.
  3. [3] Lower middle market EBITDA multiple ranges by size. Author analysis based on DealStats Value Index, GF Data, First Page Sage “EBITDA Multiples by Industry & Company Size: 2025 Report,” and dealflowagent.com. All figures are general market estimates; actual multiples vary significantly by industry, financial quality, management depth, and buyer type.
  4. [4] Due diligence timeline 30–60 days. SMB Investor Network Glossary (smbinvestornetwork.com); allantaylorbrokers.com, “What Due Diligence Really Feels Like.” Timelines vary significantly by transaction size and complexity.
  5. [5] Five years of financial records requested. Standard lower middle market M&A practice as described in multiple due diligence checklists including allantaylorbrokers.com and duedilio.com. Actual requests vary by buyer, transaction size, and industry.
  6. [6] Quality of Earnings analysis and price chipping. Author analysis based on professional M&A transaction experience. “Price chipping” is a widely recognized characterization in M&A advisory practice.
  7. [7] Customer concentration >20% as a valuation risk factor. Standard lower middle market M&A practice; SMB Investor Network Glossary definition of concentration risk. The 20% threshold is a common rule of thumb, not a universal standard; buyer tolerance varies.
  8. [8] Owner dependency as valuation killer. Business Transition Academy, “A Look at the 2026 SMB M&A Market: What Buyers Want,” businesstransitionacademy.com, 2026; general lower middle market M&A advisory practice.
  9. [9] Companion article reference. “Why Most Private Company Sales Stall or Get Discounted — And How to Make Sure Yours Does Not,” published March 1, 2026, gregg-carlson.com. That article addresses structural transaction-stage failure modes; this article addresses the financial preparation required upstream of a transaction process.
  10. [10] Gregg Carlson transaction experience. $17M business sale finance lead; $290M acquisition audit (Green Thumb Industries sale): gregg-carlson.com/background. $700M+ transaction experience figure reflects cumulative transaction value across the author’s 25+ year career and is not attributable to any single transaction or public record. Transaction experience references are for biographical context only and do not constitute a representation regarding any specific future outcome.
  11. [11] QoE adjustment ranges and deal impact estimates. The QoE adjustment ranges in Figure 2 (e.g., owner compensation normalization of 5–25% of EBITDA; deal multiple impact of 1–3x for owner dependency) are illustrative estimates based on the author’s professional transaction experience and general lower middle market M&A practice. They are not derived from a specific published study and have not been independently audited or verified. Actual QoE adjustments and deal impact in any specific transaction depend on the company’s specific financial profile, accounting practices, buyer type, and the analytical framework applied by the QoE firm engaged. Readers should not rely on these ranges as a prediction of QoE findings in any actual transaction.
  12. [12] Working capital adjustment reference ($5M–$15M). The “$5M–$15M surprise” characterization is drawn from the companion article published March 1, 2026 (gregg-carlson.com) and reflects a general illustrative range for lower middle market transactions. Actual working capital adjustments depend on the specific business’s working capital structure, the agreed peg methodology, and the transaction size. This characterization is illustrative only and should not be interpreted as a prediction of the working capital adjustment in any specific transaction.
Full Disclosure, Legal Disclaimer & Copyright Notice — Please Read in Full Before Relying on Any Information in This Article

Nature and Purpose. This article was prepared by Gregg Carlson, a Certified Public Accountant (CPA license currently inactive in the State of Nevada), in March 2026, for general informational and educational purposes only. It is not a research report, legal opinion, valuation report, fairness opinion, M&A advisory engagement letter, prospectus, or offering document. It does not create a professional advisory relationship, fiduciary duty, or duty of care of any kind between Gregg Carlson, Gregg Carlson Financial Advisory, or gregg-carlson.com and any reader.

Not Investment, Financial, Legal, Accounting, Tax, Valuation, or M&A Advisory Advice. Nothing in this article constitutes investment advice, financial advice, securities analysis, legal advice, tax advice, accounting advice, business valuation, M&A intermediary services, or any other form of professional advice. The author is not a registered investment adviser under the Investment Advisers Act of 1940, not a registered broker-dealer, not a licensed M&A intermediary, and not a licensed securities professional. Readers should not act on any information in this article without first consulting qualified professionals including M&A advisors, investment bankers, business valuation experts, CPAs, and attorneys with specific transaction experience relevant to their situation.

Valuation and Transaction Data Disclosure. Valuation multiples, QoE adjustment ranges, due diligence timelines, deal value impact estimates, and transaction outcome descriptions in this article are general market estimates and illustrative practitioner observations only. They are not forecasts, guarantees, or representations regarding any specific transaction. Actual outcomes vary materially by business, industry, financial quality, management depth, buyer type, market conditions, transaction structure, and the specific facts of each situation. Business valuation is a complex, judgment-intensive discipline. No figure in this article should be used as the basis for pricing, structuring, or evaluating any actual transaction without independent professional analysis.

Author Transaction Experience Disclosure. References to the author’s transaction experience — including the $17M business sale, $290M acquisition audit, and $700M+ cumulative transaction experience — are provided for biographical context only. Past transaction experience does not guarantee future results and does not constitute a representation that any specific outcome can be achieved for any reader. Individual transaction outcomes depend on facts and circumstances specific to each business and each transaction.

No Securities Activity. Nothing in this article constitutes an offer or solicitation to buy or sell any security, business interest, or financial instrument. This article has not been filed with or reviewed by the SEC, FINRA, any state securities regulator, or any M&A regulatory body.

Legal and Regulatory Matters. References to legal concepts, regulatory requirements, and contractual provisions (including assignability clauses, earnout structures, personal guarantees, and due diligence obligations) are general educational descriptions only. They do not constitute legal advice and do not address the specific legal requirements applicable to any particular business, transaction, or jurisdiction. Readers should engage qualified legal counsel before making any legal or contractual decisions in connection with a business sale.

AI-Assisted Research and Drafting. Portions of the research and drafting of this article were assisted by Claude (Anthropic). All editorial judgment, professional interpretation, transaction experience references, and final review are the work of Gregg Carlson. AI-assisted content carries inherent risks of error, omission, and misinterpretation; readers should independently verify material facts before relying on them.

Third-Party Sources and Data. References to third-party data sources (including DealStats Value Index, GF Data, Forvis Mazars, Kreischer Miller, Business Transition Academy, and others) are for attribution and general context only. The author has not independently audited or verified the underlying data and makes no representation regarding its accuracy, completeness, or current applicability. These sources have not reviewed or approved this article.

Forward-Looking Statements. This article contains forward-looking statements and general projections about market conditions, buyer behavior, transaction timelines, and business preparation outcomes. Actual outcomes may differ materially from any general description or estimate in this article. General market descriptions reflect conditions as understood by the author as of March 2026 and may not reflect current conditions.

Copyright and Intellectual Property. © 2026 Gregg Carlson Financial Advisory. All rights reserved. The original analysis, commentary, organizational structure, and editorial judgment in this article are the copyrighted work product of Gregg Carlson Financial Advisory. This article may be shared in unmodified form for non-commercial informational purposes with full attribution to Gregg Carlson Financial Advisory and a link to gregg-carlson.com. It may not be reproduced in whole or in material part for commercial purposes without prior written permission. Third-party data cited with attribution is the property of the respective source organizations.

General informational and educational purposes only  ·  Not investment, financial, legal, tax, valuation, or M&A advisory  ·  Author is not a registered investment adviser, broker-dealer, or licensed M&A intermediary  ·  Consult qualified professionals before acting on any information in this article

The 24-month window is real. Sellers who start this work early have choices — they can time the market, build the narrative, and negotiate from a position of strength. Sellers who start at 90 days are managing a fire drill. If a sale or recapitalization is on your horizon, I'd welcome the chance to walk through where your business stands against the preparation framework in this article. Book a 30-minute call.

Gregg Carlson

Gregg Carlson is a CPA and CFA Institute member with 25+ years of CFO and Controller experience across public companies, multi-state operators, and family offices. He has led $700M+ in M&A and capital raise transactions across gaming, cannabis, real estate, and technology. He provides fractional CFO and Controller services at gregg-carlson.com.

https://gregg-carlson.com
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