Everyone can agree—cannabis operates in a legal gray area. 

For starters, anyone in the industry is technically breaking federal law, as cannabis remains federally illegal. 

But for an in-house attorney at an MSO, the job isn’t just about navigating federal risk.

 It’s about understanding where gray meets red, balancing state-by-state regulations, and ensuring compliance across an industry with ever-changing rules—especially for a publicly traded company.

This week, we sit down with Dan Shapiro, EVP of Ascend Wellness, to break down:

• Understanding the legal gray areas in cannabis
• Shifting regulations, the Farm Bill, and Schedule 3
• Balancing legal risk and business strategy in a fragmented industry

About Ascend Wellness

AWH is a vertically integrated multistate cannabis operator with licenses and assets in Illinois, Michigan, Ohio, Massachusetts, New Jersey, Pennsylvania, and Maryland. AWH owns and operates dispensaries and seven state-of-the-art cultivation facilities, growing award-winning strains and producing a curated selection of products for retail and wholesale customers. AWH produces and distributes its in-house Simply Herb, Ozone, Common Goods, Effin' and Royale branded products. AWH also produces and distributes products on behalf of its brand partners including Miss Grass, Lowell Smokes, Flower by Edie Parker, 1906, and AiroPro. For more information, visit www.awholdings.com.

Guest Links:

• https://www.linkedin.com/in/daniel-shapiro-78830026/
• https://www.awholdings.com/
• https://www.linkedin.com/company/ascendwellnessholdings
• https://x.com/AscendHoldings

Key Topics Discussed (AI Generated)

⏱ [00:00 - 03:00] Introduction & Dan Shapiro’s Background

• Dan’s journey from law school to the cannabis industry
• His experience in highly regulated industries like aviation, insurance, and sports

⏱ [03:01 - 10:30] The Role of an In-House Attorney at an MSO

• Balancing legal risk vs. business strategy
• How MSOs structure legal teams and compliance
• The complexities of managing multiple state regulations

⏱ [10:31 - 18:45] Navigating Cannabis’s Legal Gray Area

• Why cannabis law lacks case precedent compared to other industries
• The challenge of interpreting regulations that are themselves unclear
• How MSOs make decisions with legal uncertainty

⏱ [18:46 - 25:30] Federal Illegality & The Risks It Poses

• The reality of operating in an industry that is still federally illegal
• How rescheduling (Schedule 3) could impact MSOs
• Banking & financial hurdles in cannabis

⏱ [25:31 - 32:15] The Farm Bill & The Hemp vs. Cannabis Debate

• How hemp-derived products challenge the traditional cannabis market
• The regulatory gaps between Farm Bill hemp and state-regulated cannabis
• How MSOs view hemp expansion

⏱ [32:16 - 38:50] State-by-State Regulations & Compliance Challenges

• Why no two states regulate cannabis the same way
• How MSOs strategize around shifting laws
• Scenario planning for regulatory changes

⏱ [38:51 - 45:00] Creative Legal Solutions in Cannabis

• How MSOs navigate ambiguous rules
• Balancing aggressive vs. conservative legal approaches
• Why legal teams in cannabis must be flexible

⏱ [45:01 - 50:00] Future of Cannabis Law & Final Thoughts

• Predictions for Schedule 3 and federal reform
• Why the industry needs more alignment for real progress
• Dan’s dream smoke session: Thomas Jefferson, Elvis Presley, and Tiger Woods

Our Links:

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