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Deal Structures—What Founders Get and Give Up

The economics of selling to an AI roll-up. Understanding valuation premiums, equity rollovers, earn-outs, and what your post-close life actually looks like.

Part 5 of The Founder's Guide to AI-Enabled Roll-Ups

The headline number matters less than you think.

I've watched founders celebrate a "9x EBITDA" offer, then discover that 40% was contingent on earn-outs they couldn't control, 20% was rolled equity in an illiquid holding company, and the post-close employment terms meant they couldn't actually leave for three years.

The real question isn't "what multiple are they offering?" It's "what am I actually taking home, when, and under what conditions?"

AI roll-ups are offering premium valuations compared to traditional acquirers. That's real. But the deal structures are complex, and the gap between the headline and your bank account can be substantial. Understanding how these deals work—cash at close, deferred consideration, equity components, employment requirements—determines whether you're getting a genuinely good deal or an impressive-sounding one.

This chapter breaks down the mechanics: what AI roll-ups actually pay, how the consideration splits, what earn-outs look like, and how to evaluate whether the structure works for your situation.

Key Takeaways

  • Valuation premiums are real: AI roll-ups typically offer 6-10x EBITDA for quality accounting and professional services firms, versus 4-6x from traditional buyers. The premium reflects expected margin expansion from AI transformation
  • Cash at close varies widely: Expect 60-80% of total consideration as immediate cash, with the remainder split between earnouts, seller notes, and equity rollover
  • Equity rollover is standard: Most AI roll-ups require 10-20% of proceeds rolled into platform equity. Negotiate for the same class and terms as PE sponsors
  • Earnouts are common but treacherous: 15-25% of professional services deals include earnouts. The language matters more than the target—vague definitions create expensive disputes
  • Post-close employment matters: Most deals require founders to stay 1-3 years. Negotiate the role, not just the duration
  • Deals go wrong: Platforms struggle, earnouts get disputed, rolled equity becomes worthless. Structure your deal assuming some things won't work as planned

Emotional Reality Nobody Discusses

Before we get into mechanics, let me acknowledge something the deal advisors won't tell you: selling your company is one of the most disorienting experiences of a founder's life.

The day the wire hits—and it will feel surreal when it does—you'll experience a strange mix of relief, grief, and anxiety. Relief that the uncertainty is over. Grief for the identity you've spent years building. Anxiety about whether you made the right choice.

Then comes the adjustment. Having a boss after years of ownership. Asking permission for decisions you used to make unilaterally. Watching someone else's strategy reshape the business you built.

Some founders thrive in this transition. They wanted to step back, and the structure allows them to. Others find it intolerable within six months.

The deal structure determines how trapped you are if you're in the second category. A founder who took 85% cash at close can walk away and accept the non-compete. A founder with 30% tied to three-year earnouts and vesting equity doesn't have that option.

Know yourself. Structure accordingly.

Valuation Premium—What's Real and What's Hype

Traditional valuations for professional services firms depend heavily on size. Smaller accounting practices ($2-10M revenue) typically trade at 3-5.5x adjusted EBITDA. Larger firms with more institutional characteristics command 6-8x. The very best platforms—strong growth, diversified clients, scalable operations—might see 9x or higher.

AI roll-ups are paying at the upper end of these ranges, and sometimes above. Crete, Shield, and similar platforms reportedly pay 6-10x EBITDA for quality firms, with premiums for characteristics that align with their transformation thesis.

Why the Premium?

The math is simple. AI roll-ups believe they can expand margins post-acquisition through automation. If they're right, a firm generating 25% EBITDA margins today might generate 35-40% margins in two years.

Consider a firm with $1M EBITDA. A traditional buyer paying 5x values it at $5M. An AI roll-up paying 8x values it at $8M—but if they expand margins by 40% within three years, the firm generates $1.4M EBITDA. At the same 8x multiple, that's $11.2M in enterprise value.

The premium price still creates value for the acquirer. That's the bet.

When the Premium Shrinks

Not every firm commands top multiples. Client concentration above 20% triggers discounts. Partner-dependent revenue—where relationships would walk out with you—reduces transferable value. Dated technology means more integration work, and that cost is built into your price.

But the biggest discount comes from a weak negotiating position. If you're approaching retirement with no succession plan and limited options, buyers know it. Multiple interested buyers—ideally including both AI roll-ups and traditional alternatives—create the competition that drives premium pricing.

One offer isn't a negotiation. It's a take-it-or-leave-it.

Anatomy of a Real Deal

Let me show you how this plays out in practice.

Case Study: Mid-Size Accounting Firm

A 14-person CPA firm in the Southeast with $2.1M EBITDA sold to an AI roll-up platform in mid-2024. The founding partners (two CPAs, both in their early 60s) had explored traditional succession options for 3 years without finding a workable solution.

Headline terms: 8.2x EBITDA = $17.2M total consideration

Actual structure:

Earn-out specifics: 90% of trailing twelve-month revenue is retained at the 18-month mark triggers full payout. Linear reduction below 90%—at 80% retention, they'd receive 80% of the earn-out ($2.1M).

Post-close terms: Both partners committed to 30-month employment agreements. One remained as managing partner with operational authority; the other shifted to client relationship management. Base salaries: $275K each, consistent with pre-sale compensation.

Outcome at 24 months: Client retention was 94%. Full earn-out achieved. One partner left at month 30 as planned. The other stayed on part-time. Their rolled equity is currently marked at approximately 1.8x the initial value based on the platform's most recent capital raise.

What worked: High cash percentage provided security. Achievable earn-out tied to metrics within their control. A clear role definition prevented conflict.

What they'd do differently: "We should have pushed harder on the equity terms. We got common shares, while the PE sponsors have preferred shares. If the platform sells for less than projected, they get paid first."

Case Study: Smaller Firm, Different Outcome

A 6-person tax practice in the Midwest with $650K EBITDA sold to a different AI roll-up platform in early 2024.

Headline terms: 7.5x EBITDA = $4.9M total consideration

Actual structure:

Earn-out specifics: Revenue growth of 10% annually for two years. Partial payout for partial achievement.

Post-close terms: Founding partner committed to 36-month employment. Salary: $180K, down from ~$220K pre-sale (difference attributed to "market rate adjustment").

Outcome at 18 months: Platform integration proved rocky. AI tools weren't ready when promised. Staff turnover spiked during the transition—two key employees left. Revenue declined 8% in year one rather than growing 10%. Earn-out achievement: $0.

Current situation: Founder is 18 months into a 36-month commitment, earning less than before the sale, with $1.2M in earn-outs unlikely to materialise and rolled equity in a platform that's struggling to hit targets.

Lessons: Earn-out targets based on growth (rather than maintenance) create significant risk. Salary reductions compound disappointment when other terms underperform. Platform execution matters more than platform promises.

Cash at Close—What Actually Hits Your Account

A "9x EBITDA" deal might break down as:

That $9M headline becomes $5.85M in your account on day one. The rest depends on future performance, platform success, and factors outside your control.

Typical AI Roll-Up Structure

Based on market data and deal patterns:

Cash at close: 60-80% of total consideration. Higher for highly attractive firms; lower when buyers need to bridge valuation gaps.

Seller notes: 5-15% payable over 2-4 years with interest (typically 5-8%). Generally not performance-contingent—you get paid as long as the buyer remains solvent. But they are unsecured debt.

Earn-outs: 10-25% tied to specific metrics over 1-3 years.

Equity rollover: 10-20% into the acquiring platform.

The Trade-Off Framework

The right structure depends on your situation:

Maximise cash if: You're near retirement, risk-averse, sceptical of the platform, or have other uses for guaranteed capital.

Accept more deferred/equity if: You're younger, planning to stay engaged, confident in the platform's execution, and optimising for total value over certainty.

There's no universal right answer. But don't let a buyer convince you that accepting more risk is always smart. Sometimes certainty is worth paying for.

Equity Rollover—The Second Bite

AI roll-ups almost universally require some equity rollover. This isn't generosity—it's incentive alignment. They want you invested in platform success.

How It Works

Instead of receiving 100% of your purchase price, you "roll" a portion (typically 10-20%) into equity in the acquiring platform. If the platform succeeds and eventually sells to a larger buyer, your equity participates in that appreciation.

PE sponsors typically target 3x returns. If they achieve that, your rolled equity triples. A founder who rolls $1M might receive $3M at eventual exit.

That's the pitch. Here's the reality check.

Critical Questions

What class of equity are you receiving?

PE sponsors typically get preferred shares with liquidation preferences. If the platform sells for less than invested capital, preferred shareholders get paid first. Common shareholders—often including rolled equity from sellers—get what's left.

This matters enormously in downside scenarios. If you roll $500K into common shares and the platform sells for less than its total invested capital, you could receive nothing while PE sponsors recover their investment.

Negotiate for the same class as sponsors. If they won't give it, understand exactly what protections you're giving up and price that into your cash requirements.

What governance rights come with your stake?

Most rolled equity comes with limited governance. You're along for the ride. That's fine if you trust the operators. Risky if you don't.

What restrictions apply?

Lockup periods preventing sale? Forfeiture provisions if you leave early? Drag-along rights forcing you to sell when sponsors sell? Read the operating agreement carefully.

What happens if you leave or are terminated?

Some agreements include clawback provisions. If you don't hit performance targets or depart before a specified date, you forfeit some or all of your equity. Understand the triggers and negotiate carve-outs for termination without cause.

The Tax Angle

Properly structured, equity rollover can qualify for tax deferral under IRC Section 351 or Section 721. You don't pay capital gains on the rolled portion until eventual exit.

This makes rollover economics more attractive than they initially appear. Get a qualified tax advisor involved early—the structure matters.

Earn-outs—Where Deals Go Wrong

Earn-outs tie part of your payment to future performance. They're the most common source of post-close disputes in professional services M&A.

Language That Kills You

Generic advice says "negotiate clear definitions." Let me show you what bad language actually looks like.

Problem: "Revenue" without specification

Bad language: "Earn-out based on Revenue exceeding $3.2M in Year 1."

What goes wrong: Platform moves your largest client to a different portfolio company for "strategic alignment." Your revenue drops below the threshold. The platform argues the client was never "yours" post-close.

Better language: "Revenue means gross billings from all clients serviced by the Seller's office location as of closing, including any successor clients and excluding only clients who provide a written termination notice, calculated consistently with the Seller's historical methodology."

Problem: EBITDA manipulation

Bad language: "Earn-out based on EBITDA of $800K in Year 2."

What goes wrong: Platform allocates corporate overhead, technology costs, and "integration expenses" to your P&L. Your standalone EBITDA was $850K; your allocated EBITDA is $650K. No earn-out.

Better language: "EBITDA calculated on a standalone basis consistent with pre-closing methodology, excluding any allocated corporate expenses, platform fees, or costs not directly incurred by the Seller's operations. Disputes resolved by an independent accounting firm selected by mutual agreement."

Problem: Collection timing

Bad language: "Revenue is defined as gross billings collected during the earnout period."

What goes wrong: The platform has no incentive to aggressively pursue collections once it knows the earn-out period is running. Clients who pay 45 days late cost you money if their payment falls outside the measurement window.

Better language: "Revenue defined as gross billings invoiced during the earnout period, regardless of collection timing, reduced only by amounts written off as uncollectible after 180 days using consistent historical write-off methodology."

Earn-out Negotiation Principles

Push for:

The best earn-outs feel achievable with normal effort. If hitting the target requires everything to go perfectly, assume you won't receive it and evaluate the deal on cash at close alone.

Post-Close Roles: What Your Life Actually Looks Like

Most AI roll-up deals require founders to stay 1-3 years. The reality of that continued involvement varies dramatically.

Three Scenarios

True Partnership: You remain the managing partner with real authority. The platform provides technology, back-office support, and growth capital. You run day-to-day operations with a lighter administrative burden.

Operator Under Oversight: You retain the title but report to platform leadership. Major decisions require approval. You're executing someone else's strategy.

Figurehead: Your name stays on the door for continuity. Your actual role is maintaining client relationships through transition. Strategic authority has moved to platform management.

Some founders want the third option. They're ready to step back. Others find it intolerable.

What to Negotiate

Role documentation. Get specifics in the purchase agreement. "Continued leadership" is meaningless. "Managing Partner with authority over client engagement, staff hiring/termination, and local operations, reporting to Regional Director with quarterly reviews" is concrete.

Exit triggers. Under what circumstances can you leave? What happens to earn-outs and equity? Negotiate carve-outs for termination without cause, material change in duties, or relocation requirements.

Non-compete scope. Most deals include non-competes. Understand geographic scope, duration, and restricted activities. A three-year non-compete covering "any accounting services" in your metro area eliminates post-exit options.

Compensation. Your salary, benefits, and bonus during transition. Some deals maintain prior compensation; others "adjust to market rate"—often downward.

When Deals Go Wrong

Not every deal works out. Here's what can break and how to protect yourself.

Platform Insolvency

If the platform can't pay your seller note, you're an unsecured creditor. In bankruptcy, you'll recover pennies—maybe nothing.

Protection: Negotiate a security interest in specific assets. Or accept that seller notes carry credit risk and price accordingly with higher cash at close.

Earn-out Disputes

The most common post-close conflict. The platform calculates earn-out differently than you expected. You believe you hit the target; they say you didn't.

Protection: Detailed definitions (see above). Independent dispute resolution. Audit rights allow you to review the platform's calculation methodology.

Rolled Equity Becomes Worthless

Platform underperforms. Later funding rounds dilute your stake or establish liquidation preferences that wipe out common shareholders. Your rolled equity, which was "worth" $1M, is now worth $50K.

Protection: Same class as sponsors. Anti-dilution provisions, if possible. Realistic assessment of platform risk when deciding how much to roll.

Employment Becomes Intolerable

New management. Culture clash. Strategy you disagree with. You want out, but your earn-outs and equity vest over three years.

Protection: Clear exit triggers. Acceleration of vesting if you're terminated without cause. Realistic assessment of your tolerance for loss of control before signing.

Client Defection

Clients leave because they don't like the new ownership. Your earnout fails. Your relationship-based business loses its foundation.

Protection: Earn-out based on retention you can control, not growth you can't. Communication strategy for clients during transition. Involvement in how the change is messaged.

The theme: assume something will go wrong. Structure your deal so that the most likely failure modes don't destroy your outcome.

AI Roll-Ups vs. Traditional PE: A Clear-Eyed Comparison

Let me take a position rather than hedging.

Choose an AI roll-up if:

Choose traditional PE if:

Choose neither if:

The "AI roll-up premium" often shrinks when you adjust for structure complexity and execution risk. A 6x traditional deal with 80% cash may deliver more certain value than an 8x AI roll-up deal with 60% cash and aggressive earnouts.

Run the math on realistic scenarios, not best-case projections.

Selecting Your Advisory Team

You need professional help. The question is, which professionals?

M&A Advisor

What they do: Run the sale process, create buyer competition, negotiate terms, and manage due diligence.

Fee structure: Typically 2-4% of deal value, weighted toward success fee. Some charge monthly retainers credited against the success fee.

How to evaluate:

Red flags: Pressure to sign an exclusive engagement immediately. Vague answers about comparable transactions. Unwillingness to provide references.

Transaction Attorney

What they do: Review and negotiate purchase agreements, operating agreements, and employment terms. Identify risks in the deal structure.

Fee structure: Hourly, typically $400-800/hour for experienced M&A attorneys. Total cost for seller-side representation: $30-75K, depending on complexity.

How to evaluate:

Red flags: Treating your deal as a template exercise. Missing deadlines. Inability to explain terms in plain language.

Tax Advisor

What they do: Structure transactions for tax efficiency, evaluate rollover treatment, plan for earn-out taxation, and model after-tax proceeds.

When to engage: Early. Tax structure decisions made at the aLOI stage are difficult to change later.

How to evaluate:

Get your team assembled before you receive an offer. Scrambling to find advisors after an LOI arrives puts you behind.

Negotiation Tactics That Actually Work

Having leverage means nothing if you don't use it effectively.

Create Competitive Tension

One buyer isn't a negotiation. Two or more buyers competing creates a dynamic where terms improve.

Even if you have a preferred buyer, engage alternatives seriously. Let your preferred buyer know others are interested. The fear of losing the deal to a competitor moves terms more than any argument.

Know Your Walk-Away Points

Before negotiations begin, define your minimums:

Write them down. Share with your advisor. When negotiations get intense, it's easy to convince yourself that a bad term is acceptable. Your pre-defined minimums prevent emotional capitulation.

Negotiate in Batches, Not Items

Don't fight term-by-term in sequence. Collect all the issues, then negotiate packages.

"We need to address the earn-out definition, the equity class, and the non-compete scope. Here's our position on all three. What works for you?"

Package negotiation allows trade-offs. You might accept a slightly broader non-compete in exchange for better earn-out terms. Item-by-item negotiation forecloses those trades.

Push Back at the Right Time

The Letter of Intent stage is when major terms get set. Once you sign an LOI, you have much less leverage—the buyer knows you've committed.

Fight the important battles before LOI. Save minor issues for negotiation in the purchase agreement.

Use Your Advisor as Bad Cop

Let your M&A advisor push back aggressively on terms. You remain the reasonable party focused on getting the deal done. Your advisor is the difficult one, slowing things down.

This dynamic preserves your relationship with the buyer (which matters for post-close) while still fighting for good terms.

Be Willing to Walk

The most powerful negotiating tool is a genuine willingness to walk away. If you need this deal to happen, you'll get bad terms.

The founders who get the best deals are those who would be fine without any deal. Urgency is expensive.

What a Good Deal Looks Like

Use this as an evaluation framework when comparing offers.

Valuation

Cash at Close

Earn-outs

Equity Rollover

Post-Close Role

Platform Quality

If multiple criteria fall into "concerning" territory, the deal probably isn't right—regardless of the headline multiple.

Final Thoughts

After all the analysis, the decision comes down to a simple question: Does this deal give you what you actually need?

Not what looks impressive. Not what your advisor wants to close. What you need—financially, professionally, emotionally.

Some founders need maximum cash to fund retirement, diversify risk, or pursue other ventures. For them, deal structure matters more than headline multiple.

Some founders need continued engagement, intellectual stimulation, and the possibility of a bigger outcome. For them, the "second bite" narrative is compelling, and accepting more risk makes sense.

Some founders need to be done with the stress, the responsibility, and the identity of ownership. For them, the post-close role matters more than either valuation or structure.

Know what you need. Evaluate deals against that standard.

And remember: the buyer needs you more than their confidence suggests. Quality acquisition targets are scarce. If you're one of them, you have leverage.

Use it.

← Back to Chapter 4: Inside the Technology Stack

Continue to Chapter 6: The Investment Thesis →

Or return to: The Founder's Guide to AI-Enabled Roll-Ups (Hub)

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