The 'Lawyer Extraordinaire' on cannabis and craft beer

Jeffrey O’Brien’s mix of media savvy, regulatory know-how and M&A experience has made him a go-to voice in the fast-changing cannabis and adult beverage industries. From navigating Minnesota’s overhaul of its cannabis licensing laws to structuring deals that don’t grind production to a halt, he shares what it takes to scale a practice — and a persona — in a space where the rules are still being written.

—Interview by Emily Kelchen, edited by Bianca Prieto

First of all, let’s talk about the fact that you are known as the “Lawyer Extraordinaire.” That’s quite the title!

That’s my public alter ego. It grew out of my regular guest appearances on a few podcasts—a now-defunct beer podcast, a sports podcast and a third radio show/podcast where I deal with legal issues from the political world. Then clients started saying it, and it became part of my brand.

How does your firm feel about your regular podcast appearances? 

Well, the first time I met our office managing partner to talk about joining the firm, he disclosed that he listened to one of the shows I was on, so….  In all seriousness, so long as there’s business flowing out of those appearances, they are supportive of them. 

You mention joining a new firm. You went from a relatively small firm to Husch Blackwell. What has that transition taught you about scaling a practice?

I wish I had joined the firm earlier! I didn’t realize how many of my clients were ready to scale beyond the capabilities of my former firm and even beyond the states where I am licensed. Being able to tap into Husch’s network has helped me and my clients grow. 

So the cannabis business is smokin’ hot? 

The Minnesota Legislature completely overhauled the state’s licensing process and structure in the year following passage of the initial adult-use law, and the rollout of licenses in 2025 has drawn attention to other issues that will require fixes.  

Our discussions with clients focus on how we work with the current law (even if we think it’s flawed), and, more importantly, do we try to fix the law via working with elected officials or through litigation.  

At present, a big issue is working with the brewery clients who have been making THC beverages for the past three years and assisting them as they now have to apply for “low-potency hemp edible” licenses and face a change in governance from the prior hemp statute to the new cannabis statute (and they’re not happy about it).

That sounds like a regulatory nightmare. 

What keeps it interesting is that the laws are constantly changing. Right now, the cannabis industry feels a bit like craft brewing did prior to the industry boom in the mid-2000s. Back then, it was figuring out how to remove some of the traditional “three-tier” barriers so as to allow breweries to sell direct to consumers. 

I also see similarities between the cannabis businesses and breweries or distilleries when I’m doing M&A work. Treating these transactions as a “normal” deal doesn’t work. For example, most alcohol beverage M&A transactions are structured as equity sales instead of asset sales. This keeps the federal Alcohol and Tobacco Tax and Trade Bureau (TTB) from coming in and shutting things down while permits are shuffled between owners. 

As the cannabis industry matures, we’re figuring out what special regulations are going to apply to M&A deals in it. 

You're all caught up!

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 Raise the Bar is written and curated by Emily Kelchen and edited by Bianca Prieto.