Gabriel Levine | [Top Agency Series] From Cab Driver To Top Lawyer, Viral Videos, and Navigating Digital Agencies Through the Pandemic
Smart Business Revolution

Gabriel Levine is an Attorney and Principal at Matchstick Legal, a firm that works with leading agencies, studios, and professionals across creative and technical disciplines looking to tackle business challenges, solve problems, and just get better. Gabriel has had a long career in the legal world. His practical approach to resolving difficult negotiations and disputes has brought consistent praise from both his clients and peers. Before Matchstick, Gabriel ran his own firm, Groundwork Legal, and was a partner and an associate at three different business-focused law firms in the Bay Area. 

In this episode of the Smart Business Revolution Podcast, John Corcoran interviews Gabriel Levine, an Attorney and Principal at Matchstick Legal, about his entry into the legal space and how he started his own business. They also discuss the evolution of the legal profession, the challenges of practicing law nationally and internationally, and Gabriel’s experience as a cab driver.

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Here’s a Glimpse of What You’ll Hear:

  • Gabriel Levine talks about being a cab driver after college
  • Gabriel’s experience working in employment law — and how a viral video helped propel his career
  • Why Gabriel transitioned to partner with his father
  • The strategies Gabriel uses to scale his business
  • Gabriel talks about the challenges of practicing law nationally and internationally — and the evolution of legal agencies
  • What Gabriel is most excited about in the digital agency space
  • How sales in the legal profession has changed over the years

Resources Mentioned In This Episode

Sponsor: Rise25

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Episode Transcript

Intro 0:14

Welcome to the revolution, the Smart Business Revolution Podcast, where we ask today’s most successful entrepreneurs to share the tools and strategies they use to build relationships and connections to grow their revenue. Now, your host for the revolution, John Corcoran.

John Corcoran 0:40

All right, welcome everyone. John Corcoran here. I am the host of the show. You know, if you are new to listening to this podcast, go check out some of our archives because got some great episodes of smart CEOs, founders, entrepreneurs, professionals from all kinds of companies, including Netflix, Kinkos’, YPO, EO, Activision Blizzard, we’ve got GrubHub coming up in a couple of days. We had quick and recently Redfin some interesting founders and CEOs. And I’m also the Co-founder of Rise25. So if I were to help connect b2b business owners to their ideal prospects, and for those of you who’ve been listening for a little while, you know that I am also a recovering lawyer, and I have a soft spot my heart for other attorneys out there, especially other attorneys that are doing entrepreneurial things. And so I was introduced recently to an entrepreneurial lawyer who’s here today to talk about some of the work that digital agencies are doing, which of course, as you know, from some of the different episodes that I’ve done, are some of the most vibrant areas of the economy where some of the most cutting edge work is done before it gets rolled on to other parts of the economy. 

So first shout out to Joe Rinaldi, the Principal That Was Clutch, who introduced me today’s guest, his name is Gabe Levine. He is the attorney and principal imagistic legal and he’s got a long career in in the legal world. Perhaps most interesting, at least to me is that we have the same alma mater, both undergrad and law school, which is pretty unusual. He graduated before me from law school and he worked at a bunch of different San Francisco Bay Area firms, littler Mendelson is one of the most well respected employment firms out there. Also during law school at the University of San Francisco. There’s an external to justice Ming Qin, very well respected scholar at the California Supreme Court and received a number of different awards while he was in law school as well. Of course, it’s episode brought to you by Rise25, we help b2b businesses to get clients referrals and strategic partnerships with done for you podcasts and content marketing, and you go to our website to learn more about what we do at

Alright, Gabe, such a pleasure to have you here today. And, and first of all, I want to get to this viral video that really kind of kick started your career, kind of really famous early viral video that you started telling me about. I didn’t even know about it before we hopped on a call here today that you were involved in it, but I knew it instantly when you started describing to me, we’re gonna get into that viral video that maybe you’ve seen as well. But before we do, after you graduated from UC Santa Barbara where we both went, you went and did the night shift. You’re going out driving around Santa Barbara, driving a cab around Santa Barbara, which is beautiful place not as beautiful at night, but still is a nice place. And I want to hear some crazy stories about driving a cab around Santa Barbara, honing your entrepreneurial chops, picking up drunks in the middle of the night.

Gabriel Levine 3:28

Yeah, well, thanks for having me John. I appreciate it. Like you said Go Gauchos. Go Don’s Yes. You ever think about that connection? Like gauchos Don’s?

John Corcoran 3:38

I know right? It’s kind of unusual. Both. Both of our own monitors are

Gabriel Levine 3:43

our cowboys. Yeah, I guess so. Yeah. Argentinian. Yeah. Yeah, I drove a cab. I had a year to kind of kill between college and law school. At least I thought I was going to do law school. But I hadn’t yet taken the LSAT. My wife who was my then girlfriend had another year to go in college. I needed something to do. Me and my buddy were sitting around looking at the want ads over the summer after my senior year, his junior year, because that’s waiting. You did back then when you’re looking for a job. That’s what you did. Yeah. And the Independent Journal or I think that’s what it was called the Santa Barbara. I don’t know that’s the marine Independent Journal. The Santa Barbara News Press independent

John Corcoran 4:23

or something? Yeah. Yes, yeah, one of those papers.

Gabriel Levine 4:27

So it sounded pretty easy. We kind of knew the streets around downtown. We both lived there for a year so we tried it got our cab licenses, which wasn’t too difficult, actually scary, scary, scarily easy. And drove around and you know, the first night I think I made like 120 bucks after gas and tipping the dispatcher which is the thing you do if you want good rides. So I was hooked. Did that for almost a year while I studied for the LSAT and hung around Santa Barbara and ate and drank too much in preparation for law school and yeah, there’s plenty of crazy stories.

John Corcoran 5:03

Tell me the craziest. I mean, you had a must have had some crazy people hopping in the backseat.

Gabriel Levine 5:08

Well, okay. I think the craziest was actually. So there’s a bunch of bars in Santa Barbara and a bunch of college kids. And you know, they’re getting way too blasted. And I was 21 for reference. And one night, I went to pick up at this bar where we didn’t have any friends. We had friends at a lot of bars, and they would call us for generally like good rides, or better rides, and just bouncers like practically dragging and corralling out, you know, what you would think was a wild animal, but it had to be like, maybe 21 year old girl who was, like, out of her mind on more than just booze? Surely more than had it been

John Corcoran 5:50

a stuffer in the back of

Gabriel Levine 5:52

you. They want to stuff in the back of a cab. Yeah, yeah. You know, 1999 Yeah. And it was like, no, no. And then, you know, I mean, she can’t decide who to yell at. And whether it’s me or the bouncer, I’m like, I there’s just no way I’m taking her and you gotta get her. Go get her to the hospital. And she was like, you know, kicking the roof of the cab. I mean, it was, it was crazy. That so that ended the hope that we make are we as a society are making more responsible choices these days, but I’m not so sure. That’s certainly happening in parts of the country and world, I suspect. You know, everybody’s got Uber now. So it’s a little different. But yeah, I definitely had people snorting various or some type of drug, which I would guess would have been cocaine off of the rate card. Hey, can I see your rate card for a minute? So it’s like we had a little card that you just

John Corcoran 6:48

do something flat?

Gabriel Levine 6:49

Yes. There were some college kids maybe, you know, doing a little doing a little more than they should have back there. And sex in the backseat? Possibly, maybe just oral sex. And that was annoying me so I kept hitting the brakes puke in the cab. And so I would go to an ATM and like make them give me money. I think it was like 60 or 80 bucks if you can the cab, man. Yeah, that’s probably long enough. But the cab stories.

John Corcoran 7:23

Yeah. And and any older women that were kind of prowling on the prowl,

Gabriel Levine 7:29

right? Yes, totally. I mean, it’s Santa Barbara. For sure. They’re, you know, again, I’m 21. And there were some you know, around to 230 in the morning, sometimes three 340 pick up from particular bars like Joe’s or I don’t even think it exists anymore Tiburon and on upper State Street and yeah, there would be some, some lonely. It’s funny to say this now. So then 45 But 40 Somethings looking looking like you know, the 21 year old cab driver, like a piece of meat? Yeah. Probably propositioning me. And I was living with my now wife and girlfriend. So I didn’t take them up on it. But it was, it was there was some aggressive behavior. Yeah.

John Corcoran 8:09

So naturally, this is, you know, normal transition to law school from undergrad to law school, right? That’s what you do, right? You, you do this kind of work. But so you go to law school, and you end up working at a bigger firm for a few years, then go work at a smaller firm, more entrepreneurial firm, where you kind of learn the chops. And the thing with the practice of law, that, unfortunately, is that when you’re young, and just out of law school, you don’t get the best experience. Most of the time, if you’re at a bigger firm, right? Like the kind of grinding you sell, like you got better experience at the second firm. And that’s where your big opportunity came along. So tell us about this viral video that really kind of helped establish your career.

Gabriel Levine 8:56

Okay, yeah. Yeah, I mean, really quickly, you know, the big firm, I was at decent work, but, you know, you work with whatever partners wanted you. And that didn’t always work for me, because I have a strong personality, and some of them did as well. And I’ve never been the best at taking direction. So I left for a great little firm in the city where my dad knew these, you know, at the time, quite young attorneys that had a growing practice. And yeah, they let me kind of run with stuff and trusted me and it was great. And actually, let

John Corcoran 9:26

me pause. Let me pause right there. So your father was actually an employment attorney, and you worked at an employment law firm, but then went off and did something else did? Did it feel at all having grown up around that? Did you feel like you’re letting your dad down at

Gabriel Levine 9:43

all? Oh, no. Yeah. I mean, he tried to push me away from the law from an early you know, do something interesting, you know, in college, like learn a language do something useful. And I was like, Yeah, I’m just gonna drink and do bong rips and then figure it out after college. You know, looking back I wish Hillard a skill or something, and I hope my daughter goes through it, you know, Polytechnic University and learns a skill. But you know, she’ll probably end up like me.

John Corcoran 10:08

So Nevertheless, you end up really like in the exact same profession and the same and not just the exact same profession, but the same area of law for a couple years.

Gabriel Levine 10:16

Right. Right. And I and I, you know, I wanted to be in the trenches. And employment law was an area where you could make enough money on like, criminal law. And, you know, unless you want to do weird white collar stuff, which I wasn’t into, you know, we could make enough money and get thrown in the trenches, because not every case was, you know, a high stakes litigation. And at the time, I went to littler the rates were very reasonable, like back way back then. So I didn’t, you know, get thrown in the trenches. But I didn’t, you know, I didn’t have a dream of being an employment lawyer. I just, it was kind of like a vehicle to do something interesting, which I thought was like being the courtroom and administrative hearings. But then I fell out of love with that pretty quickly. And just wanting to I didn’t even know, you know, do I like law. So I go to the small, firm, and yeah, they let me be a lot more entrepreneurial. My very first client was a referral from my dad’s then law partner. She was big in this sort of boom in the 90s. And so she and then particularly with, with business, women, females, and so there was a woman named Erica Hall who contacted her at mule design studio in the city, which was a and still is, but they don’t do this type of work anymore. Web design firm an up and coming web design firm with a very good reputation, especially with philanthropic clients and organizations. And her business partner. His name is Mike Monteiro, they’re both well known for their design chops and interesting personalities. Now they’re married. But they came to me and via Elisa, who was my dad’s law partner, and formed a corporation for them and got them all set up. And they were my first client. And so they kind of got me introduced to the San Francisco burgeoning web design business, and I got a bunch of clients there. Tell me if I’m running long, no, keep going. Alright. So as I felt like, you know, I was approaching the time, you know, five years or so past where I was like, Oh, are you guys gonna make me a partner? Now? I think you probably should. And they wanted me to kind of be more aggressive about outreach and growing my book, not just relying on sort of, it was foreign to me at the time, I’m like, You want me to do what I’m a good lawyer. That’s all I can do.

John Corcoran 12:28

The funny thing about law is that you, you know, the first couple years is just like learn the practice of it, you don’t actually get trained in how to actually bring in clientele and build a book of business, that sort of thing. And then when it comes time to make partner, it’s like, Well, you got to do all this, this other thing, it’s kinda like goalpost totally.