This episode features Jason Horst, a former Am Law 100 attorney who left Big Law to build his own practice in the high-stakes world of the California cannabis industry. Jason shares the inside story of the "Green Rush," explaining why the initial excitement collapsed under the weight of crushing taxes, heavy regulation, and what he calls the "Al Capone law" that prevents legal cannabis businesses from taking normal deductions. He details his strategic pivot from a struggling industry to a diversified, locally-focused practice and offers a masterclass in marketing through genuine, one-on-one connection. The conversation takes a deep dive into the impact of artificial intelligence, as Jason—a heavy early adopter—discusses which AI tools are changing the game, the ethical thicket of their use, and his critical concerns about how the next generation of lawyers will be trained when AI automates their foundational work.
Show Notes
(0:26) Introduction: Jason Horst’s journey from Big Law to founding Horst Legal Counsel.
(3:43) Why the security of Big Law is an illusion without a book of business.
(4:11) The personal and professional constraints of a large firm's corporate culture.
(7:33) Making the jump: Why the cannabis industry required a "jump in with both feet" approach.
(8:22) The early days of cannabis law: "Everybody here is a felon."
(10:43) How Jason found his niche as one of the first insurance coverage lawyers in the cannabis space.
(12:37) The "Green Rush" fades: How unsustainable regulations and taxes crippled the industry.
(15:03) "Death by a thousand bullet holes": The 70% effective tax rate killing legal cannabis businesses.
(18:26) The "Al Capone Law": How the IRS prevents cannabis companies from taking ordinary business deductions.
(20:17) Jason’s marketing strategy: The power of showing up and building one-on-one connections.
(22:14) How to pivot when your primary industry dries up.
(31:13) When to hire: Growing a firm from a solo practice to a full-service shop.
(31:42) Using the gig economy to scale a law firm up and down effectively.
(35:34) The legal tech stack that makes running a firm easier than expected.
(38:50) A deep dive into AI's impact on legal practice.
(39:45) Why AI output should be treated like a first-year associate's work product.
(43:09) The business model paradox: AI tools increase expenses while decreasing billable hours.
(43:38) The critical question: How do we train junior lawyers when AI automates their work?
(53:58) How AI will dramatically increase the pace of litigation and the pressure on courts.
(01:03:42) Jason’s favorite AI tools that are changing his practice.
(01:06:33) Where to find and contact Jason Horst.
Contact Jason: jason@horstcounsel.com
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Music: lofi type beat "flower market" by snoozy beats.