
Advisory · Glossary
The words in the room.
Every term that decides a business sale, defined the way we would explain it across a table. 43 entries, from add-back to 280E.
- 280E
Section 280E of the Internal Revenue Code, which disallows ordinary business deductions for businesses trafficking in Schedule I or II controlled substances. It raises effective tax rates for cannabis operators and lowers after-tax cash flow, and therefore value. As of April 2026, qualifying medical cannabis products were placed in Schedule III while adult-use remained in Schedule I.
- Add-back
An expense added back to reported profit when calculating SDE or adjusted EBITDA because a buyer would not incur it: owner perks, one-time costs, above-market owner salary. Every add-back must be documented, or a buyer's quality-of-earnings review will remove it.
- Adjusted EBITDA
Earnings before interest, taxes, depreciation and amortization, normalized for non-recurring items and market-rate management compensation. The earnings base most buyers of companies with a management team use to price a deal.
- Asset sale
A transaction in which the buyer purchases specific assets and assumes specific liabilities of the business rather than buying the legal entity. Common in smaller deals and where the buyer wants to leave liabilities behind. Tax treatment differs from an equity sale.
See: Equity sale
- Basket
A threshold of losses a buyer must exceed before it can claim indemnification from the seller. Negotiated alongside the cap and the escrow.
- Buy-side advisory
Representation of the acquirer: defining criteria, sourcing targets including off-market companies, evaluating them, structuring an offer, and managing diligence and closing.
- Cap
The maximum amount a seller can be required to pay under the indemnification provisions of a purchase agreement, usually a percentage of the price.
- Change of control
A transfer of ownership or effective control of a company. Many contracts, leases and licenses contain clauses triggered by it, and licensed industries require regulator approval of it.
- Change of ownership approval
In licensed industries such as cannabis, the regulator's review and approval of new owners before a transaction can close. It sits inside the deal timeline and governs when and whether a deal closes.
- CIM
Confidential Information Memorandum. The detailed document describing a company to approved buyers under NDA: history, operations, customers, financials, growth opportunities and reasons for sale. Preceded by an anonymous teaser.
- Closing
The completion of the transaction: definitive agreements signed, conditions satisfied, funds transferred, ownership changed. Any success fee is paid through the closing process.
- Data room
A permissioned, secure online repository where diligence documents are shared with approved buyers. Access is granted per party and can be revoked.
- Deferred revenue
Payments received for services not yet delivered, recorded as a liability. In software and subscription businesses it is both a liability the buyer assumes and evidence of the recurring revenue the buyer is paying for.
- Due diligence
The buyer's investigation of the company after an LOI: financial, legal, tax, operational, commercial, technical and regulatory. Exit planning works through the same list in advance.
- Earnout
Contingent consideration paid after closing if the business hits defined targets over a set period. Its value depends on the metric, the period, the seller's control over the outcome and the protections against buyer interference.
- EBITDA
Earnings before interest, taxes, depreciation and amortization. A proxy for operating cash flow used as the earnings base for valuation multiples in companies with a management team.
See: Adjusted EBITDA, SDE
- Engagement agreement
The contract between a seller or buyer and its advisor setting scope, term, confidentiality and fees. Fee terms are private and never published on this site.
- Equity sale
A transaction in which the buyer purchases the ownership interests of the legal entity, taking the company with all its assets, liabilities, contracts and licenses. Often required where a license is issued to the entity.
See: Asset sale
- Escrow
A portion of the purchase price held by a third party after closing to cover indemnification claims, released to the seller after a defined period if no claims are made.
See: Holdback
- Exclusivity
A period during which the seller agrees not to negotiate with other buyers, usually granted on signing an LOI. Its length is a negotiating point; a seller grants it deliberately, not by default.
- Exit planning
The structured preparation of a company for sale twelve to thirty-six months in advance: financial normalization, owner-dependence reduction, contract cleanup, systems documentation and a valuation checkpoint.
- Holdback
Purchase price retained by the buyer rather than placed with a third party, released later subject to conditions. Functionally similar to escrow with less protection for the seller.
See: Escrow
- Indemnification
The seller's obligation to compensate the buyer for losses arising from breaches of representations and warranties or specified matters. Limited by baskets, caps and survival periods.
- LOI
Letter of Intent. A mostly non-binding document setting out the principal terms of a proposed transaction: price, structure, timing, exclusivity and conditions. Signing one starts due diligence.
See: Exclusivity
- Multiple
The factor applied to an earnings or revenue base to arrive at value. Determined by comparable transactions and buyer behavior in an industry and size range, then adjusted for the specific company's risk and growth.
- NDA
Non-Disclosure Agreement. Executed by a buyer before receiving any information that could identify a company. In our process, no CIM moves without one on file.
- Net revenue retention
Revenue from a customer cohort a year later, after churn and expansion, as a percentage of the starting revenue. Above one hundred percent means the base grows without new sales.
- Net working capital peg
The agreed level of working capital the business must have at closing. If actual working capital is above the peg the price adjusts up; below, it adjusts down. Often the most under-negotiated number in a deal.
- Non-compete
The seller's agreement not to compete with the business for a period after closing within a defined scope and territory. Its terms are part of the value a buyer is paying for.
- Normalized earnings
A company's profit restated the way a buyer will see it, after add-backs and adjustments for non-recurring items, related-party arrangements and accounting differences.
- Off-market
A company that is not publicly for sale and has not been marketed by an intermediary. Off-market deal flow comes from direct, confidential owner outreach.
- Proof of funds
Evidence that a buyer has the capital, or committed financing, to close. Required in our process before a buyer receives identifying information.
- Quality of earnings
An independent review, usually commissioned by the buyer, that tests whether reported earnings are sustainable and accurately stated. It examines add-backs, revenue recognition, working capital and one-time items.
See: Add-back
- Representations and warranties
Statements of fact the seller makes about the company in the purchase agreement. If untrue, they give rise to indemnification claims. Reps and warranties insurance can shift that risk to an insurer.
- Rollover equity
A portion of the seller's proceeds reinvested as equity in the buyer's entity. Upside if the buyer succeeds, illiquid until the buyer's own exit.
- SDE
Seller's Discretionary Earnings. EBITDA plus one full-time owner's compensation and benefits, plus add-backs. The earnings base used for owner-operated companies. Higher than EBITDA for the same company, with correspondingly lower multiples.
- Sell-side advisory
Representation of the seller in a transaction: readiness, valuation, marketing materials, buyer outreach under NDA, negotiation, diligence coordination and closing.
- Seller note
Financing the seller provides to the buyer as part of the price, repaid over time with interest. Its rate, term, security and subordination decide whether it is a bonus or a risk.
- Success fee
A fee payable to the advisor upon completion of a transaction, typically calculated on the transaction value and paid through the closing process. Terms are documented in the engagement agreement.
- Transition services
The seller's agreed post-closing involvement: duration, role, compensation and scope. Often paired with a non-compete.
- True party of interest
In cannabis and other licensed industries, any person or entity with an ownership, control or profit interest that a regulator requires to be disclosed and approved. Definitions and thresholds vary by state.
- Working capital adjustment
The post-closing true-up of the purchase price against the net working capital peg, based on the closing balance sheet.
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Notice
Black Key Holdings provides business transaction and M&A advisory services. We do not provide legal, tax, accounting, investment, securities or regulatory advice. Services and transaction structures vary by jurisdiction. Each party should retain its own qualified legal, tax, accounting and regulatory professionals. Nothing on this website constitutes an offer to sell or a solicitation of an offer to purchase any security or licensed business interest.