Shay Gilmore / Louis Goodman Transcript

Louis Goodman / Sha Gilmore

Louis Goodman 00:00
I’m in collaboration with the Alameda County Bar Association, this is Loved Thy Lawyer, where we talk with members of the ACBA about their lives and legal careers. I’m Louis Goodman, the host of the LTL podcast. And yes, I’m a member of the Alameda County Bar Association.

Shay Aaron Gilmore has worked the big firm. He’s practiced insurance defense. He now has his own practice involving regulatory compliance, corporate governance, licensing, commercial contracts, and all other aspects of business law, advice and transactions. But what makes Shay’s practice fascinating is that it all revolves around the cannabis industry. He is a top 20 Daily Journal cannabis lawyer. He is a Super Lawyer. He served on the JNE commission. He’s been involved in continuing legal education. He’s published articles in the legal cannabis space. And of course, he’s a member of the Alameda County Bar Association. Shay Gilmore, welcome to the Alameda County Bar Association and the Love Thy Lawyer podcast.

Shay Gilmore 01:23
Thank you, Louis for having me, very pleased to be here.

Louis Goodman 01:27
It’s a pleasure to have you I really am interested in talking to you about your practice and the type of practice because it is a little unusual. Where are you speaking to us from right now?

Shay Gilmore 01:38
I’m here in San Francisco, California, where I have my own law practice. It’s just me as a solo practitioner. And I’ve been in business as a solo since California adopted adult use cannabis on January 1, 2018.

Louis Goodman 01:57
What type of practice do you have? Can you describe it? I mean, I said it up in the intro a little bit, but how do you describe it?

Shay Gilmore 02:05
Sure. Yeah, it’s pretty much exactly like you described. It’s a corporate commercial, regulatory business transaction focused practice with the kind of I guess, distinguishing factor of all of my clients are either operators in the cannabis space or investors in this space. So it really is kind of like a way of taking a general business practice, but really specifically targeting the I consider to be like a movement for the expansion of access to this plant.

Louis Goodman 02:46
How long have you been doing that specific type of practice?

Shay Gilmore 02:50
So specifically to cannabis. It’s been since January 1 2018 when I opened my own practice. I had previously worked as in house counsel on mergers and acquisitions and other business, transactional matters. So had already some exposure, particularly from like the business side to kind of what these legal deals were made up of and the kind of processes and approaches that were really effective and really adapted, kind of what I’ve learned in a more traditional General Counsel setting to the cannabis industry movement.

Louis Goodman 03:31
Where are you from originally?

Shay Gilmore 03:33
I’m originally from Texas.

Louis Goodman 03:35
Yeah, whereabouts in Texas.

Shay Gilmore 03:36
I grew up in Corpus Christi, Texas, and went to college in Houston, and law school at the University of Texas at Austin.

Louis Goodman 03:46
What college did you go to in Texas?

Shay Gilmore 03:49
Well, I went to Rive University for undergrad. But when you asked what college I thought you were being very specific, and might be I don’t know, but I was at Jones college at Rice when I was an undergrad.

Louis Goodman 04:03
And is there something that Jones specializes in as opposed to anything else?

Shay Gilmore 04:09
No, Rice has a residential college system, where you’re randomly unless your legacy assigned to one of I think there are now 10 undergraduate residential colleges where your meals and gather college related functions, and it’s a way of like taking the university experience and kind of like really shrinking it down to a smaller section of it. And each college is named after somebody they gave a bunch of money. At my college is Mary Gibbs Jones College. She was the wife of Jesse Jones, who is a major oil man in Texas for a long time.

Louis Goodman 04:53
Well, maybe there’ll be a Gilmore college at Rice one of these days.

Shay Gilmore 04:55
Sure. I mean, lord knows I’ve given him enough money. All right.

Louis Goodman 04:59
Well, how was that experience at Rive? Did you enjoy it?

Shay Gilmore 05:02
Oh, yeah, no, I mean, my best friends in life really were made there. I’ve had, what’s the opportunity to grow both my law practice as an alum of the University, and as well as the friendships that I made there. I consider it a small Rives, it’s not very big school, but it really does punch above its weight, and attracts a real diversity of talent that I feel very privileged to have been a part of and continue to be part of.

Louis Goodman 05:38
Then you went to law school where?

Shay Gilmore 03:40
At UT and in Austin.

Louis Goodman 05:42
In Austin. Okay. Did you take any time off between college and law school?

Shay Gilmore 05:48
No, I didn’t. And I recommend people do if anyone’s interested in going to law school, and they haven’t already.

Louis Goodman 05:59

Shay Gilmore 05:59
Well, I think that it was my impression that the more mature the more reflective, and I better kind of emotionally equipped to handle Law School. Were those that had actually taken time between undergrad, I’m 25 years old, you’re still kind of a child, really. I think your brain doesn’t even really start fully developing or doesn’t even end I guess it’s full development until your mid 20s. So it was my experience in law school that the more mature and level headed students were those that had taken some time.

Louis Goodman 06:37
Yeah, I agree. I took a little bit of time between college and law school, but the people who really were good law students had taken a few years. Well, that brings up the question, when did you first decide that you wanted to be a lawyer?

Shay Gilmore 06:54
My mom worked at a law firm in Corpus Christi as an office manager and paralegal. And so I’ve been around lawyer growing up just from folks that she knew from work. And I had always kind of like, looked at it as something that I knew I could do, and would be good at. I didn’t really make like a formal decision, I guess. And so I decided to go to law school, which was in 98. And then kind of from there, I did come close to not being what I guess I was so nerve wracking in that California bar exam. I had studied so hard, and didn’t have very high pass rate. And I was coming from Texas and kind of felt like I was fighting to arms tied behind my back. And I really, at the end of studying for that test, at the end of taking it I just said, I don’t care if I pass it or not, I’m never taking this test again. I couldn’t take it anymore. I said, if I don’t pass, I’m just going to find something else to do. I won’t be able to practice law. Okay, so we’ll figure it out but well, I passed and became a lawyer after that.

Louis Goodman 08:13
What was it that prompted you to take the California bar as opposed to the Texas bar or one of the other 49 bars that are available?

Shay Gilmore 08:22
Right. Well, it actually came from a conversation I had with a woman who was like, she was in the administration at the law school in like the career counseling section of the law schools administration, she and I, it was like a formal meeting. She and I were just kind of out at like a law school function. And it probably was sponsored by some law firm in town. And I said to her I’m really interested in moving to California at some point, maybe I’ll work here, in Austin for a few years, and then move. And she said, get out, get out of here. She’s like, God, now. What are you waiting for? You have to be a Texas lawyer to be a California lawyer, one go, practices in California, go do that. And so I think that I had always kind of seen myself not really spending my adult life in Texas. It’s been 25 years there. I knew it. And I’d done it. And I was really that conversation that got me on the move out West.

Louis Goodman 09:37
Can you give us a brief history of your legal career from graduating and passing the bar, and then going into the call a traditional business law world to where you are and what you’re doing now?

Shay Gilmore 09:53
Sure. Yeah. So right after I graduated from law school, I worked for Lewis Brisbois, which is a large California, well, I guess now they’re all over the country law firm. I did work for a commercial litigation team in that office in Los Angeles. Their main client was one of these insurance subsidiary of AIG. They actually, I liked one of the cases I remember on there as kind of fun, ensured the James Bond franchise. And so I got to see like an actual handwritten note from Sean Connery like 1960, or whatever. That was in Los Angeles, from there, I moved to San Francisco. And I worked for a law firm that has now absorbed into Dwayne Morris. And then from there, I worked at another law firm that has now been absorbed to squire Patton Boggs, which I think itself was wire Sanders and also patent. There’s a lot of mergers in the legal services space over the last few years, I got hired by the client out of that job to go work in the general counsel’s office of a subsidiary of Allianz. And then also worked for another professional liability insurer here in San Francisco until I opened my own practice in January 2018.

Louis Goodman 11:19
And what prompted that?

Shay Gilmore 11:21
Well, it was really like, specifically, I had a conversation with my husband. And we had just watched, I think, as everyone had the Prop 64, which Californians passed in November 2016 about to turn into law. And I think that I’ve always had an interest in this space, but just had not done any of the actual legal work at that point in time. So I’ve been very good friends with a colleague and friend of mine for a long time, and who’s a Partner at Farella in San Francisco, and he founded their cannabis industry practice. And I took him out for drinks. And I said, Ryan, I’m really interested. And I think this is like 2017. And I said, I don’t know if I might be too late. He said too late? What are you talking about? We haven’t even written the regulations yet. There’s no law here. This is exactly when lawyers want to get involved. And at that point in my career, I’d done litigation, I’d done transactions, I’d done some government relations work, I kind of felt like I had enough kind of legal chops to be a general counsel and adviser to companies. And because of the specific regulatory focus of this law practice and the evolving nature of those regulations, I had a way to get up to speed really quickly, because I was basically learning it just like everybody else was at the time, the regulations were being written.

Louis Goodman 13:06
Is there anything about cannabis as such, and the cannabis industry is such that really attracted you to it as someone who wanted to be on the cutting edge of the cannabis world?

Shay Gilmore 13:21
Well, I think several things, I think, there’s the whole medicinal and health aspects to the product that is not well researched enough that doesn’t enjoy the kind of federal support that other industries and in this country, certainly do. And I think that there’s opportunity there for lawyers to engage with the lawmakers, with the regulators, and to really, there’s a whole, like I say, a whole scientific medicinal aspect there. But for me, I’ve really been motivated by the social justice angle of this movement. This is what we’re witnessed in this country is just, it’s not normal at all. And it is a real embarrassment I think, to us as a country and sure, embarrassment, really like kind of heartbreaking embarrassment to us as lawyers that we’ve allowed it that kind of just unimaginably unfair disproportionate incarceration and prosecution rates and people of color in this country at the hands of kind of in a Nancy Reagan fanatical, just say no weirdos, and we’ve really got to get a handle on this. We’re talking about a plant that according to the CDC, the Centers for Disease Control has resulted in exactly zero deaths from ingestion, ever. So, I think we’ve lost kind a real opportunity to be focused on the science. And because of the kind of racial inflection of the prohibition movement in this country really, I think subjected ourselves to a tremendous amount of shame.

Louis Goodman 15:20
What do you really like about practicing law?

Shay Gilmore 15:23
I enjoy the relationships. Ever since I started practicing law have really enjoyed building through experience. And through surveys, a connection with my clients, with my colleagues with other friends in in legal work that I do, either for nonprofit and for others, I really like the relationships that I’ve built.

Louis Goodman 15:53
If a young person were just graduating from college, thinking about a career, would you recommend the law?

Shay Gilmore 16:00
Yeah, yeah, I think no matter what you’re interested in, coming out of college, there’s a legal service application right there. If you are interested in aviation, and you’re a pilot, well I’ve got a good friend who’s the Deputy General Counsel of Alaska Airlines, right? I think if you’re interested in communications, they’re real legal issues to tackle there around the First Amendment and whatever. I think that if you’re interested in courtrooms and kind of like the life of a trial and kind of excitement that goes with that and certainly legal education can get you get you prepare.

Louis Goodman 16:49
How was actually practicing law met or differed from your expectations about it?

Shay Gilmore 16:53
I think that I overestimated how different it would be than kind of life pre. I think before I started practicing, I had kind of a mystified idea about the practice, and that there were some kind of like scroll of legal Latin incantations that you were to recite as do debate magic happen and really what I’ve come to understand in law practice there is no magic. There’s just the law, there’s just what happened or what didn’t, and there’s just reasonable people engaged in looking at all of these events and trying to make the most sense out of them.

Louis Goodman 17:39
What about the business of practicing law and how’s that gone for you since you started your own practice? And what sort of tips or suggestions could you give to people who are starting out in going into practice out of a big firm?

Shay Gilmore 17:55
Yes, I’m now in my fifth year of practice, it’s grown every year. So, it’s seven years, it’s grown like more than others. And I think it’s really kind of tracked the larger economy for legal services I’m a solo practitioner, and kind of along for the ride, really, as the economy moves so will my clients and then so will I. Now I think, for tips for getting clients when I first got this idea that I’d do this, when I was still in house, and I talked to my mom about it, her first question was, do you think you can get clients? And I said, yeah, as I think I can. And I think tips are really on things around being very open to potential opportunities that you may not see directly in front of you, a client, but you may see someone who knows one. And I’ll give an example, I had a friend from yoga class that ended up being best friends with a cannabis manufacturer in Humboldt County, who then became the general counsel for a company and then from her developed other relationships, she’s very well connected in that cannabis community there in Humboldt. So I think don’t ever kind of arrogantly presume that what opportunity may lie out there, and to be very open to it. And I think also to just really think about what it is that interests you, if you’re not interested in the work or the kind of legal environment that you’re practicing in, it’s really good. I guess it’s hard to hide that from potential business partners and clients. And so really, I think conveying your interest is going to be key to developing more business.

Louis Goodman 19:59
Is there anything that you know now that you really wished you knew before you started your own practice?

Shay Gilmore 20:04
I think I’ve wished that I think I was too nervous about it, I think that I wish I would have known that it was going to be okay. I think that at the beginning of it I was kind of more preoccupied with kind of reflecting success or achieve achieving or whatever. And really, I’ve kind of just through experience with the clients and with the legal community over time really let go of that. And it really used that opportunity to deepen my expertise and real passion for this space.

Louis Goodman 20:48
Do you think the legal system is fair?

Shay Gilmore 20:50
No, it’s absolutely not. I mean life is not fair. And legal system is just as good as the kind of flawed foundations that it rests on. And quite frankly, it just is flawed as some of these appointees, I mean, you can go ask the 11th circuit about how they feel about district, Jilin Cannon and how good a job she’s doing. We’re not living in a system that’s fair. And that said, do I think that there are ideals that are absolutely you founded on fairness? Absolutely not. I think that United States a system can may not be the best that has ever been or will be, but it is the best in the world. And I think we have something to be proud of in this country and in this state, our state, in particular, as a model internationally, like you mentioned, I served on the Judicial Nominees Evaluation commission for the State Bar. And we’ve had the EU government and governments around the world kind of copy what we’ve done in California around that. So is it fair? No way, but is that any reason to stop believing in the ideals of fairness? No. No there’s no reason.

Louis Goodman 22:14
Going to shift gears here a little bit, Shay, what do you like to do to get your mind off of practicing law? What do you do in your own time?

Shay Gilmore 22:24
I’ve practiced a lot of yoga, I’ve practiced this morning, I practice pretty much every day, I’ve loved just kind of time that I get to focus on just breathing and being present. And doing that with a bunch of other people kind of similarly focused at the same time, it can be really invigorating.

Louis Goodman 22:50
How do you define success?

Shay Gilmore 22:52
I think that I would define it as doing a good job for the right reason.

Louis Goodman 23:01
Let’s say you came into some real money, three or $4 billion, what, if anything, would you do differently in your life?

Shay Gilmore 23:10
Is that even real money right now? I mean, just three or 4 billion, I mean, come on, well, I would not go buy a social media platform and overpay for it, and then running into the ground.

Louis Goodman 23:23
You need a lot more money than three or 4 billion to do.

Shay Gilmore 23:27
I need much more, right? Yeah, do something that is inspired is that. So I think that I’m really interested in dismantling a lot of the kind of structural inequality that I’ve just seen in my life growing up in Texas, for sure but as I’ve learned over my law practice in California, and I think that if I had three or $4 billion, I would think about working with nonprofits that were really interested in kind of strategically politically dismantling a lot of the institutional bias that we see that results in just this really heartbreaking inequality.

Louis Goodman 24:20
What keeps you up at night?

Shay Gilmore 24:21
Well, I do get nervous about my clients and whether they’re smart enough to take my advice.

Louis Goodman 24:34
I think that keeps all of us.

Shay Gilmore 24:37
Yeah, I mean, I can beg, I can tell him the rule, I can beg them to follow it, I give them eighty different reasons why it’s a good idea and all the bad consequences that can flow from not following that advice that you cannot make that horse drink water, you can just do the best you can to lead them there. And still, I think the kind of other side of recognizing that you cannot make that horse drink is that you will sometimes be up worrying that horse is going to fall over from dehydration.

Louis Goodman 25:15
Yeah, my dad practice law for over 50 years and he once said loop, you can give clients advice, but you can’t make them take it.

Shay Gilmore 25:25
Yeah, it’s true. And I think that that’s something that it’s very different from being an associate where you’re responsible to another lawyer, who was a partner, who’s kind of making the call versus being in this role, and where I was when I was in house yeah, I’d be talking to people who didn’t really have time to care about anything that I thought was, I guess, a value to the law firm culture, like prestige of the law school, or the types of cases that I was working on. All they saw was a lawyer who could answer their legal question right now, so they could move on with their day. And it’s so you really didn’t have much and sometimes they took your advice, and sometimes they didn’t, right? Because they were just coming for an answer most of the time, they were smart, and they took it. But one of the things that I really kind of understand was, I am not the business. I don’t run a business, selling cannabis, or investing in cannabis. But I sure can tell you what the law says about those things.

Louis Goodman 26:48
Let’s say you had a magic wand, that was one thing in the world that you could change, the legal world or otherwise, what would that be?

Shay Gilmore 26:54
Well, I think I would like the world and the legal world in general to exhibit far more compassion than exists right now. I think that there’s a lot of opportunity that’s missed in the legal profession, and the greater world for seeing yourself in the other. And if I could wave a magic wand, I changed all that right away.

Louis Goodman 27:30
What’s the best way for someone to get in touch with you if they would like to talk to you about your legal services?

Shay Gilmore 27:39
Best way is through my website, and that is And I’ll say it more slowly. So it’s more digestible, www.

Louis Goodman 28:08
Great. Let’s start with Alan Borelli. I see you on the call. And you had some questions in the chat. Alan Borelli, what’s your question or comment for Shay?

Alan Borelli 28:19
I put the question in the chat just about chances are federal government legalizing it. And also like timeline, the safe Banking Act is not in the defense bill.

Louis Goodman 28:31
if I may, and correct me if I’m wrong here Alan, your question is, what do you think the chances are for federal legalization of cannabis? And what about the federal regulations with respect to banking and how that affects the cannabis business?

Shay Gilmore 28:52
Right. And I think Alan’s asking about a timeline, which is, of course, like the $24 billion question or that I’ve been hearing, I’ve been in this space now for five years. It’s just five years away. Well time’s up. It should be here by now. I think that you named it the most promising piece of federal not legalization, but progress in this space would be the safe Banking Act, but it doesn’t look like this year it’s going to happen which is just another year of missed opportunity. Now, I will say you got this year for the first time the federal government has expanded access to cannabis for research. That’s the first time that that’s happened and you also had two more states come online as the result of these November elections, Missouri came online and in Maryland, and look, Arkansas wasn’t that far off. Alright. So we’re in a space where we can talk about Arkansas and it’s not like a pipe dream because it’s going to happen.

Louis Goodman 30:03
Joanne Kingston, you signed into the chat. Do you have a question or a comment for Shay?

Joanne Kingston 30:08
You’re speaking about racial inequities, can you be more specific about where and when you have encountered that? Or is that in other states and easiest, we’re waiting to Cajun states where cannabis has not become legal?

Shay Gilmore 30:27
Yes, I think where I’ve encountered it in my law practice has been only here in California, in the commercial cannabis industry, where it is still evolving. 100% there is a racial component to the amount of economic opportunity to the amount of success in the media environment with cannabis that is tied to race and is an embarrassment.

Joanne Kingston 30:56
Are you talking about the ability to open a club and have a commercial business?

Shay Gilmore 31:04
Yes. If you are white, and male in this space, you have access to capital that other demographic groups can only dream.

Joanne Kingston 31:16
Where does that capital comes from?

Shay Gilmore 31:19
It comes from other white people. I mean, you’re right. It’s not like the black people are over here handing out it. I mean, it’s kind of obvious, right? And specifically, you’re talking about small private equity groups, you now see cannabis companies that are publicly traded on the Canadian stock exchange. So now you’ve got retail investment money. Again, these are white people that have money to invest in the retail securities market.

Louis Goodman 31:51
I’d like to give you one more opportunity to chime in with anything that you think you’d like to say that you haven’t had a chance to so far.

Shay Gilmore 32:02
No, I think you have given me so much time. I apologize if I’ve gone on and on about this stuff, but I really am interested in it and really enjoy working to expand access to cannabis throughout California,

Louis Goodman 32:16
Shay Gilmore, thank you so much for joining us today on the Love Thy Lawyer podcast and the Alameda County Bar Association podcast and I want to thank Joanne Kingston and Alan Borelli for joining us today as well and Cailin Dahlin for running the program. Thank you very much.

That’s it for today’s edition of Love Thy Lawyer in collaboration with the Alameda County Bar Association. Please visit the website where you can find links to all of our episodes. Also, please visit the Alameda County Bar Association Website at, where you can find more information about our support of the legal profession, promoting excellence in the legal profession and facilitating equal access to justice.

Special thanks to ACBA president Pamela Ross and Criminal Justice Chair Annie Beles, staff members Cailin Dahlin, Sayeed Randall, Valerie Brown Lescroart and Hadassah Hayashi.

Thanks to Joel Katz for music, Bryan Matheson for technical support, Paul Robert for social media and Tracy Harvey. I’m Louis Goodman.

Shay Gilmore 33:47
Yeah, I really didn’t have any kind of agenda item.

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