Jeremy Siegel was two weeks into his first in-house GC role at Eaze, a cannabis delivery startup, when he picked a fight with the CEO on a company-wide Slack channel. The squabble? Where a specific item should appear on the website’s product menu. Classic.
Jeremy's position was clear: in the world of legal cannabis, products must be categorized in a very specific way to avoid compliance fines. The CEO wanted the product shown in a different place for aesthetic reasons. Legally speaking, Jeremy was correct, but the public conflict cost him more than he anticipated.
"I probably shouldn't have started that fight," Jeremy admits. "I was new in-house, trying to be a stickler with the rules...giving into that fight would have probably bought me more capital with the CEO."
That experience taught Jeremy a valuable lesson that’s served him well in his career. The best in-house lawyers understand which battles to fight, which hills to die on, and which arguments to save for a private conversation. Every GC must learn this lesson eventually, and the best lawyers learn it early on.
Building a Legal Function in a Budding Industry
Jeremy found his way to the cannabis industry via an unusual path: a clerkship at the Court of International Trade in Washington D.C. He then moved to a California-based boutique regulatory firm specializing in alcohol delivery before being recruited by Eaze for his experience working with highly regulated consumer products.
Jeremy became the company’s first Director of Compliance, responsible for building the first digital platform for cannabis delivery in the United States. His role included all of the fun stuff: fighting for App Store approvals, wading through state regulations, payment processing nightmares, and keeping everyone compliant in a highly regulated industry.
And because this was the early days of California’s legal cannabis industry, Jeremy built all of it largely from scratch, in one of the most scrutinized and misunderstood markets in America. This meant designing how Eaze’s legal department would operate in uncharted territory, navigating regulators who were equal parts curious and terrified, and learning when to push and when to let things go, skills that have served him well in the years since.
Jeremy is now General Counsel at Amerit Fleet Solutions and founder of Legal Mise, where he serves as a fractional GC for five startups across AI, agriculture, logistics, and CPG.
Optimizing Your First 30 Days In-House
Your first month in-house is the perfect time to take stock of what’s working well, what’s keeping people up at night, and how legal can help bridge the gap. Jeremy argues that a GC’s job isn’t to fix everything in the first 30 days, it’s to establish yourself as a resource for legal needs across the business.
According to Jeremy, the biggest difference between working in a firm, where lawyers are paid to give advice, and working in-house, is how lawyers are integrated into business outcomes. The most effective in-house lawyers avoid becoming order-takers for executives and instead work as strategic partners with leaders across the company.
"I don't want there to be one person sending me off to work,” said Jeremy. “Then it feels more like a law firm again. It feels like I'm very siloed. Once you go in-house, your words have more weight."
Attorneys who want to set themselves up for success in-house should spend the first month focusing on discovery. Where does the business need the most support and how can legal make the biggest impact?
GC’s First 30 Days Checklist:
Ask: What's keeping you up at night?
Map: Who needs legal support most? (Product? HR? Sales?)
Build: Direct relationships across functions
Assess: Hygiene issues vs. strategic gaps
Create:
At early-stage orgs: Draft first terms, privacy policy, and merchant agreements
At established orgs: Update policies and complete compliance audits
Approaching this discovery phase strategically is critical for your legal function’s long-term effectiveness. But taking the time to gather this data is only worth your time if you understand which battles are worth fighting.
Don’t Wait for a Seat at the Table
Prior to his role at Amerit Fleet Solutions, Jeremy was GC at Final Bell, a company that designs and builds supply chain solutions for cannabis brands. Although this role had much less risk than his previous positions, the way Jeremy approached the role stayed the same. He insisted on being part of all strategic initiatives at Final Bell so that nothing fell through the cracks.
"I'm in all the conversations, or at least I force myself into the conversations if I feel like one's happening and I'm not getting enough visibility," Jeremy said.
Ensuring he’s in the right rooms means building close relationships with the CEO, COO, EVP, and board. It means understanding product roadmaps and expansion plans before they become legal issues. It also means showing up with solutions, instead of merely pointing out problems.
"The job of a General Counsel is to understand the business in and out, to not think about things purely through a legal lens, but think about a way to make sure the business is growing and succeeding," Jeremy explains.
This problem-solving mindset also powers his fractional GC practice. Jeremy now advises five to six companies simultaneously across AI, agriculture, logistics, and CPG. Every single client came through referrals because Jeremy has positioned himself as a doer.
Note from CZ: Learn the business relentlessly. Invest in relationships before you need them. Don't wait to be invited into strategic conversations. Know enough to recognize when you should be there, and show up. This approach will take you further in your career than many other strategies.
On Working Collaboratively With Founders
Successful entrepreneurs have vision and passion, but they also have blind spots. Jeremy has worked as a GC for both founders and professional CEOs, and these two personas operate very differently. Founders push hard on things that matter to them, and often those priorities are at odds with the needs of the business.
"I hate that people think legal is a blocker," Jeremy says. "I think the legal team could be your best partner and can make the company the most successful...as long as you work collaboratively with them and you don't leave them in the dark until the very end."
Here's an example Jeremy sees often: a document is ready to sign, everyone's aligned, and then legal sees it for the first time. Twelve rounds of redlines follow. What could have been a simple process if legal had been involved early becomes a negotiation nightmare that delays the deal. Building authentic relationships across the business helps legal stay aligned with other departments and reduces reactivity.
Here’s what Jeremy wishes every founder knew: legal actually makes the process more efficient…as long as you bring them in early.
Before picking a fight, ask yourself:
What’s the legal risk?
Does being "right" affect the company’s revenue, brand, or compliance?
What does this fight cost you in CEO trust or board capital?
Should this conversation happen over email, Slack, or in-person?
Knowing when to push back or let it go is a skill built over many years, but having the right tools can make a big difference.
Embracing a New Age of Legal Automation
"I think we're in one of the most exciting times when it comes to the law," Jeremy says. "There are so many different areas that are rapidly evolving, that don't have rules that make sense yet. As in-house lawyers, we get to be a part of building the cool shit."
In addition to his GC work, Jeremy advises AI companies building machine learning tools for pharma and investing in them. Because each of his clients has a different risk profile, Jeremy uses AI constantly to work more efficiently.
"Everyone copies and pastes. Everyone finds good precedent, modifies it to the way that they want to use it, and then claims it as their own," Jeremy explains. "AI does it much more efficiently and cleanly. And it does a much better job maintaining tone."
Here's how Jeremy uses legal AI in his day-to-day work:
Regulatory comparison: Easily pull regulations from multiple states, compare them, and generate a table.
Trademark analysis: One of Jeremy’s clients wanted to trademark a descriptive name. AI generated a 10-factor ranking showing why the name was weak, along with a client-friendly explanation in seconds.
Multi-client management: Different AI profiles remember different risk appetites and communication styles to keep everything on-tone.
Modern legal automation tools (like GC.AI) can easily handle document review, due diligence checking for specific terms, and reviewing limitations of liability. Your in-house attorneys should focus on novel concepts, regulatory strategy, delivering business advice, and asking the right questions.
Whether you're the first legal hire at a startup, a fractional GC juggling five clients, or a seasoned leader, your mindset should be the same: discover, integrate, build relationships, choose your battles wisely, and use automation to work faster.
Want to hear more? Listen to the full episode where Jeremy shares stories about creative cash-hiding in cannabis, writing actual law with state legislators, and why The Amazing Adventures of Kavalier & Clay landed him a second date.
After you’ve listened to the episode, try GC AI free and see what's possible with legal AI built specifically for in-house teams.
