CANNABIS VENTURE CAPITAL TERM SHEETS & EQUITY FINANCINGS ATTORNEY CALIFORNIA
A venture capital term sheet is the foundational document of a priced equity financing — the non-binding letter of intent that sets the economic and governance terms of a proposed investment before the definitive financing documents are drafted and executed. In cannabis, term sheet negotiation carries stakes that exceed those of a comparable non-cannabis financing: federal illegality, DCC ownership approval requirements, § 280E tax exposure (for adult-use operators), and the absence of Chapter 7/11 bankruptcy protection for cannabis businesses create risks that must be surfaced, allocated, and managed in the term sheet itself, not left to be addressed after the investor has committed.
The Law Office of Shay Aaron Gilmore advises cannabis companies and their investors on venture capital term sheets, priced equity financing rounds, and the full suite of definitive financing documents — including Stock Purchase Agreements, Investor Rights Agreements, voting agreements, and Right of First Refusal and co-sale agreements. Ranked Band 4 in Cannabis Law: Western United States by Chambers and Partners, recognized as one of the Top 20 Cannabis Lawyers in California by the Los Angeles / San Francisco Daily Journal, as named as one of the Top 100 Lawyers in Northern California across all practice areas by Super Lawyers® Magazine, Shay Aaron Gilmore brings both venture capital transactional experience and cannabis regulatory depth to every equity financing engagement. Shay serves on the Board of Directors of both the International Cannabis Bar Association (INCBA) and California NORML, and he chairs the California Lawyers Association Cannabis Practitioners Group.
Whether representing a cannabis company seeking its first institutional round or a fund negotiating board representation, information rights, and anti-dilution provisions in a Series A, the Law Office of Shay Aaron Gilmore provides experienced, cannabis-specific venture capital counsel.
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Key Term Sheet Provisions in Cannabis Equity Financings
Federal scheduling status: State-licensed medical cannabis is now Schedule III under the federal Controlled Substances Act (21 U.S.C. §§ 801 et seq.), removing qualifying medical operators from IRC § 280E. Adult-use/recreational cannabis remains Schedule I and subject to IRC § 280E. Dual-license operators who want to claim IRC § 280E relief on their medical operations must segregate their medical and adult-use supply chains. A broader DEA rescheduling proceeding remains underway.
| Term Sheet Provision | Cannabis-Specific Consideration | Hemp-Specific Consideration |
|---|---|---|
| Valuation | § 280E-adjusted EBITDA must be the basis for valuation; GAAP metrics are misleading | Hemp businesses may use GAAP metrics if hemp operations are fully separated from cannabis |
| Liquidation preference | No federal bankruptcy protection means exit dynamics differ; preference structure matters more | Same general principles apply; federal bankruptcy available to pure hemp businesses |
| Board rights | Board members who are DCC "owners" require prior DCC approval before taking seat | No DCC approval required; standard corporate governance procedures apply |
| Anti-dilution | Down rounds common in cannabis; broad-based weighted average preferred | Same terms apply; hemp companies may have better access to capital in down environments |
| Information rights | § 280E creates GAAP/economic divergence; adjusted financial metrics important | Standard information rights sufficient if hemp is separated from cannabis operations |
| DCC change-of-control trigger | Must be addressed expressly as a condition precedent to equity issuance | CDFA notification may be required; less burdensome than DCC approval |
Definitive Financing Documents in Cannabis Venture Rounds
After a term sheet is signed, the parties negotiate and execute the definitive financing documents. In a cannabis venture round structured as a preferred stock financing, the core documents are: the Stock Purchase Agreement (SPA), the Investor Rights Agreement (IRA), the Certificate of Incorporation (as amended to create the preferred stock series), the Right of First Refusal and Co-Sale Agreement, and the Voting Agreement.
The SPA governs the purchase and sale of preferred shares, contains representations and warranties by the company (including representations regarding regulatory compliance, DCC license status, and absence of pending enforcement actions), and sets closing conditions. In cannabis, the SPA must include representations specific to the industry — including representations that the company holds all required DCC and local licenses, that there are no pending DCC enforcement actions, that the company’s § 280E compliance is current, and that all owners have been disclosed to the DCC.
The National Venture Capital Association (NVCA) publishes model form documents for VC financings that are widely used in non-cannabis deals. The Law Office of Shay Aaron Gilmore adapts NVCA model documents for cannabis-specific provisions, including DCC ownership disclosure conditions, regulatory compliance representations, and § 280E disclosure provisions.
Representative Matters
The Law Office of Shay Aaron Gilmore has handled the following types of venture capital and equity financing matters:
- Represented a secured investor in a $500,000 secured investment in a cannabis retail development company. Negotiated investor protections appropriate for a multi-location retail development operating within a complex California cannabis regulatory environment.
- Handled buy-side representation in the $500,000 acquisition of a cannabis manufacturing and distribution company in Ukiah, taking over from prior counsel mid-transaction, reconfiguring the deal structure to satisfy DCC regulatory requirements, and obtaining regulatory approval to complete the change of control.
- Served as regulatory counsel for a secured creditor in a controlled creditor takeover of a cannabis cultivation business, advising on DCC license transfer mechanics in the absence of federal bankruptcy protection, working alongside finance counsel from Squire Patton Boggs.
- Represented the majority shareholder in the restructuring of a cannabis retail entity operating in San Francisco, navigating a minority shareholder dispute and positioning the company for a restructured ownership and governance framework.



