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Part of Acquisitions and exits: reading deal mechanics
Why 'Best Acquisitions and Exits 2027' Isn't a Ranking
Best acquisitions and exits 2027 isn't a ranked list. This guide weighs payment, timing, earnouts, holdbacks and obligations against seller constraints.
There is no best acquisition. There is an offer that fits what a particular seller needs, and a set of offers that do not.
So this page ranks nothing. It takes the seller's seat instead. A search for the best acquisitions and exits 2027 has no universal answer: given two or three offers on a table, what separates them, and which differences matter more than the headline number?
The celebrity transactions below illustrate different structures. Rare Beauty, the Selena Gomez cosmetics brand, drew a minority investment from a group including Sir John and other backers rather than an outright sale.
Ryan Reynolds sold Aviation Gin to Diageo in 2020 for an upfront figure plus an earnout tied to growth targets.
George Clooney and Rande Gerber sold Casamigos to Diageo in 2017 for $700 million upfront with up to $300 million more contingent on performance.
What to take away
- Headline price says little about what the seller receives. Timing, contingency and continuing obligations decide that.
- Two offers with the same number can differ by years in when the money arrives, and by whether it arrives at all.
- Aviation Gin and Casamigos both carried earnouts. The seller's payout depended on targets the buyer's team then ran.
- A seller with other shareholders or investors is not free to pick the offer they personally prefer.
- Name the constraint that made the sale worth doing before comparing anything.
The seller's own constraint comes first
Before comparing offers, name the thing that made a sale worth doing.
- Getting out.The seller wants to stop working in the business. Any structure requiring three more years of their attention fails, whatever it pays.
- Certainty.The seller wants a known amount on a known date. Contingent consideration is a discount, not an upside.
- The upside.The seller believes the business is about to get much better and wants a share of that. A larger cash figure now is the worse deal.
- Keeping the name usable.The seller wants to do something else in the same category later. A broad non-compete or a wide name license is disqualifying.
- Protecting the team.The seller cares what happens to the people. This is a real constraint and it is routinely ignored in comparisons.
An offer is better or worse only against one of those. That is why published rankings of deals are entertainment: they are scoring answers without knowing the question.
What actually differs between two offers
What actually differs
The comfortable version
- Form of payment
- Cash at closing
- Timing
- One payment
- Contingency
- None
- Holdback
- Small, short, capped
- Seller obligations
- A clean handover
- Name license
- Term limited, categories listed
- Restrictions
- Narrow non-compete
- Liability
- Capped and time limited
The version that costs the seller
- Form of payment
- Buyer's stock, which is not money until it can be sold
- Timing
- Installments over years, unsecured
- Contingency
- An earnout on marks the buyer now controls
- Holdback
- A large sum in escrow for a long period
- Seller obligations
- Years of appearances, posts and events
- Name license
- Perpetual, all categories, worldwide
- Restrictions
- A bar on the seller's whole trade
- Liability
- Uncapped for a long list of matters
Both Aviation Gin and Casamigos carried contingent money, and the sellers' final take depended on hitting targets after the buyer took over.
Two Offers Compared
Comfortable
- Payment
- Cash at closing
- Timing
- One payment
- Contingency
- None
- Holdback
- Small, short
- Obligations
- Clean handover
- Name license
- Limited categories
- Restrictions
- Narrow non-compete
- Liability
- Capped, time limited
Costs Seller
- Payment
- Buyer's stock
- Timing
- Unsecured installments
- Contingency
- Earnout on marks
- Holdback
- Large, long escrow
- Obligations
- Years of appearances
- Name license
- Perpetual, worldwide
- Restrictions
- Bar on whole trade
- Liability
- Uncapped, long list
The three that hurt later
The holdback. Part of the price sits in escrow as security for the promises the seller made about the business. It is normal. It becomes painful when the period is long and the list of matters it secures is open ended, because the seller has spent the rest of the money and cannot fund a claim.
In small consumer deals, a typical holdback runs 12 to 24 months. It is usually capped at 5 to 10 percent of the price and secures only the seller's representations on financial statements, brand ownership, and undisclosed liabilities.
The continuing obligation. Post-sale promotional agreements are common in this category and they are work.
The Federal Trade Commission's (FTC) Guides Concerning the Use of Endorsements and Testimonials in Advertising explain when endorsers should disclose a material connection to a brand. Selling the company does not erase an ongoing endorsement relationship or its disclosure implications.
A seller who signed for three years of content has sold their time as well as their business.
The earnout. The seller is paid more if the business performs, and the buyer decides everything that determines whether it does. This is the single most reliable source of post-closing disagreement in small consumer deals.
Targets are usually written as a revenue or gross profit figure for the next 12 to 24 months. Measurement follows the buyer's accounting system and the buyer's standard policies.
Payout is often a percentage of the excess over the target, or a single sum if the target is hit. Disputes come from the definitions: what counts as revenue, which costs are deducted, and whether the target resets when the buyer changes distribution.
When the choice is not the seller's to make
Where the company has other shareholders, directors deciding between offers owe duties to the company, not to whichever shareholder likes an offer best. The note on fiduciary duty sets the general shape of that duty.
In practice, a founder cannot pick a buyer they get on with, and a minority holder cannot block a deal they merely dislike.
Investors also hold contractual rights that reorder the outcome: consent rights over a sale, a preference on the proceeds, and drag-along provisions that force a reluctant minority to sell alongside the majority. The celebrity companies page explains why the arrangement behind a headline determines who is even in the room.
A comparison worksheet that ranks nothing
Set the offers side by side and fill this in for each. Do not score it out of ten; read the rows against the constraint you named at the top.
Offer Comparison Worksheet
- Amount payable at closing, unconditionally
- Amount payable later, and what it depends on
- Non-money payment, and when it converts
- Total months of seller's time required
- Length and breadth of restrictions afterward
- Who decides earnout measurements
- What happens to name if buyer stops using it
- Which employees have written offers
Here is an illustrative pair on the same business. Offer A pays $40 million cash at closing. Offer B pays $25 million cash plus up to $25 million on an earnout.
A comparison worksheet
Offer A
- Form of payment
- Cash at closing
- Timing
- One payment
- Contingency
- None
- Holdback
- 5 percent for 12 months
- Seller obligations
- None after closing
- Name license
- None
- Restrictions
- Non-compete, 3 years, skincare only
- Liability
- Capped at the holdback
Offer B
- Form of payment
- 60 percent cash, 40 percent buyer stock
- Timing
- Cash at closing, stock locked up for 12 months
- Contingency
- $10 million earnout on year one revenue
- Holdback
- 10 percent for 24 months
- Seller obligations
- Two appearances a year for three years
- Name license
- Seller keeps a license for skincare only, 10 years
- Restrictions
- Non-compete, 5 years, all beauty categories
- Liability
- Uncapped for IP and tax matters
On a certainty constraint, Offer A wins. On an upside constraint, the same seller can prefer Offer B.
The acquisitions and exits page covers how the headline number is assembled. The portfolio case studies page shows how to check what a buyer's group actually is before agreeing to join it.
When a transaction is a licensing arrangement dressed as a sale, the franchises and licensing page describes the line between the two.
Why we do not publish a ranked list
A list of the year's best exits would need private prices, confidential terms, and judgment about outcomes not visible for years. Every published version is assembled from announcements written by the parties.
The best celebrity companies 2027 page makes the fuller argument about what a real ranking would require.
Common questions
Is an all-cash offer always the best one?
For a seller who wants certainty, usually. For one who believes in the buyer's plan, taking stock or an earnout can be worth more. Neither is right in the abstract.
How long should a holdback last?
In small consumer deals, 12 to 24 months is a typical period and 5 to 10 percent of the price a typical cap. Ask what it secures, whether it is capped, and what has to happen for release.
Can I compare an offer to what similar businesses sold for?
Only loosely, because those terms are private and the reported figures are usually headline totals including contingent money. Treat comparisons as orientation, not as pricing.
Should I take advice on this?
Yes, from a lawyer and an accountant who act for you rather than for the buyer, and before you sign anything, including a letter of intent that looks non-binding.







