Life of a Fellow Niche Internet Micro Celebrity with Matt Margolis

Episode Summary

Matt Margolis, Head of Community at Lawtrades, joins Corey on Screaming in the Cloud to discuss the life of a professional shitposter. Matt, who Corey discovered on TikTok, reveals how he went from being an attorney to being an attorney with a thriving online audience that laughs at his jokes. Matt and Corey discuss how much of a difference it makes to be able to bring your whole self to work, as well as how they found themselves outside of the traditional way of doing things in their chosen professions. Matt also discusses his role at Lawtrades, where attorneys are able to find that kind of freedom from the “old guard” and companies are able to get legal expertise based on their needs and budget.

Episode Show Notes & Transcript

About Matt

Matt is the head of community at Lawtrades, a legal tech startup that connects busy in-house legal departments with flexible on-demand legal talent. Prior to this role, Matt was the director of legal and risk management at a private equity group down in Miami, Florida. 

Links Referenced:


Announcer: Hello, and welcome to Screaming in the Cloud with your host, Chief Cloud Economist at The Duckbill Group, Corey Quinn. This weekly show features conversations with people doing interesting work in the world of cloud, thoughtful commentary on the state of the technical world, and ridiculous titles for which Corey refuses to apologize. This is Screaming in the Cloud.

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Corey: Welcome to Screaming in the Cloud. I’m Corey Quinn. Something that I’ve learned in my career as a borderline full-time shitposter is that as the audience grows, people tend to lose sight of the fact that no, no, the reason that I have a career is because I’m actually good at one or two specific things, and that empowers the rest of the shitposting, gives me a basis from which to stand. Today’s guest is Matt Margolis, Head of Community at Lawtrades. And I would say he is also a superior shitposter, but instead of working in the cloud space, he works in the legal field. Matt, thank you for joining me.

Matt: That was the nicest intro I’ve ever received in my entire career.

Corey: Well, yes, usually because people realize it’s you and slam the door in your face, I assume, just based upon some of your TikToks. My God. Which is—I should point out—where I first encountered you.

Matt: You found me on TikTok?

Corey: I believe so. It sends me down these really weird rabbit holes, and at first, I was highly suspicious of the entire experience. Like, it’s showing ADHD videos all the time, and as far as advertisements go, and it’s, “Oh, my God, they’re doing this really weird tracking,” and like, no, no, they just realize I’m on TikTok. It’s that dopamine hit that works out super well. For a while, it drifted me into lesbian TikTok—which is great—because apparently, I follow a lot of creators who are not men, but I also don’t go for the whole thirst trap things. Like, who does that? That’s right. Must be lesbians. Which, great, I’m in good company. And it really doesn’t know what to make of me. But you show up on my feed with fairly consistent frequency. Good work.

Matt: That is fac—I appreciate that. I don’t know if that’s a compliment, though. But I [laugh]—no, I appreciate it. You know, for me, I get… not to plug a friend but I get—Alex Su’s TikToks are probably like, one in two and then the other person is—maybe I’m also on lesbian TikTok as well. I think maybe we have earned the similar vote here.

Corey: In fact, there’s cohorts that they slot people into and I feel like we’re right there together. Though Ales Su, who has been on the show as well, talk about source of frustration. I mentioned in passing that I was going to be chatting with him to my wife, who’s an attorney. And she lit up. Like, “Oh, my God, you know him? My girlfriends and I talk about him all the time.”

And I was sitting there going, well, there better damn well be a subculture out there that talks about me and those glowing terms because he’s funny, yes, but he’s not that funny. My God. And don’t tell him that. It’ll go to his head.

Matt: I say the same thing. I got a good one for you. I was once in the sales call, and I remember speaking with—I was like, “You know, I’m like, pretty decent on Twitter. I’m pretty decent on LinkedIn”—which I don’t think anyone brags about that, but I do—“And I’m okay on, like, Instagram and TikTok.” And he goes, “That’s cool. That’s really cool. So, are you kind of like Alex? Like, Alex Su?” And I go? “Uh, yeah,” he goes, “Yeah, because he’s really funny. He’s probably the best lawyer out there that, you know, shitposts and post funny things on the internet.” And I just sat there—and I love Alex; he’s a good friend—I just sat there, and I’m like, “All right. All right. This is a conversation about Alex. This isn’t a conversation about Matt.” And I took him to stride. I called Alex immediately after. I’m like, “Hey, you want to hear something funny.” And he got a kick out of it. He certainly got a kick out of it.

Corey: It’s always odd to me, just watching my own reputation come back to me filtered through other people’s perceptions whenever I wind up encountering people in the wild, and they say, oh, you’re Corey Quinn at—which is usually my clue to look at them very carefully with my full attention because if their next words are, “I work at Amazon,” that’s my cue to duck before I get punched in the face. Whereas in other cases, they’re like, “Oh, yeah, you’re hilarious on the Twitters.” Or, “I saw you give a conference talk years ago,” or whatever it is. But no one ever says the stuff that’s actually intellectually rigorous. No one ever says, “Yeah, I read some of your work on AWS contract negotiation,” or, “In-depth bill analysis as mapped to architecture.” Yeah, yeah. That is not the stuff that sticks in people’s head. It’s, “No, no, the funny guy with his mouth wide open on the internet.” It’s, “Yep, that’s me. The human flytrap.”

Matt: Yeah, I feel that. I’ve been described, I think, is a party clown. That comes up from time to time. And to your point, Corey, like, I get that all the time where someone will say, “Matt I really enjoyed that meme you posted, the TikTok, the funny humor.” And then every so often, I’ll post, gosh, like, an article about something we’re doing, maybe a white paper on commercial contracting, or some sort of topic that really fits into my wheelhouse, and people were like, “That’s… I guess that’s cool. I just thought you were a party clown.” And you know, I make the balloon animals but… not all the time.

Corey: That’s the weirdest part to me of all of this is just this weird experience where we become the party clowns and that is what people view us as, but peeling away the humor and the jokes and the things we do for engagement, as we’re like, we’re sitting here each trying to figure out the best way to light ourselves on fire and survive the experience because the views would be enormous, you do have a legal background. You are an attorney yourself—still are, if I understand the process properly. Personally have an eighth-grade education, so basically, what I know of bars is a little bit of a different context.

Matt: I also know those bars. I’m definitely a fan of those bars as well. I am still an attorney. I was in private practice, I worked in the government. I then went in-house in private equity down in Miami, Florida. And now, though I am shitposter, you are right, I am still a licensed attorney in the state of Florida. Could not take a bar exam anywhere else because I probably would light myself on fire. But yeah, I am. I am still an attorney.

Corey: It’s wild to me just to see how much of this world winds up continuing to, I guess, just evolve in strange and different ways. Because you take a look at the legal profession, it’s—what is it, the world’s second oldest profession? Because they say that the oldest profession was prostitution and then immediately someone, of course, had a problem with this, so they needed to have someone to defend them and hence, lawyers; the second oldest profession. And it seems like it’s a field steeped in traditionalism, and with the bar, yes, a bit of gatekeeping. And now it’s trying to deal with a highly dynamic, extraordinarily irreverent society.

And it feels like an awful lot of, shall we say, more buttoned-down attorney types tend to not be reacting to any of that super well. I mean, most of my interaction with lawyers in a professional context when it comes to content takes a lot more of the form of a cease and desist than it does conversations like this. Thanks for not sending one of those, by the way, so far. It’s appreciated.

Matt: [laugh]. No worries, no worries. The day is not over yet. First off, Corey, I’m going to do a thing that attorneys love doing is I’m going to steal what you just said and I’m going to use it later because that was stellar.

Corey: They’re going to license it, remember?

Matt: License it.

Corey: That’s how this works.

Matt: Copy and paste it. I’m going to re—its precedent now. I agree with you wholeheartedly. I see it online, I see it on Link—LinkedIn is probably the best example of it; I sometimes see it on Twitter—older attorneys, attorneys that are part of that old guard, see what we’re doing, what we’re saying, the jokes we’re making—because behind every joke is a real issue a real thing, right? The reason why we laugh, at least for some of these jokes, is we commiserate over it. We’re like, “That’s funny because it hurts.”

And a lot of these old-guard attorneys hate it. Do not want to talk about it. They’ve been living good for years. They’ve been living under this regime for years and they don’t want to deal with it. And attorneys like myself who are making these jokes, who are shitposting, who are bringing light to these kinds of things are really, I would say dis—I hate to call myself a disrupter, but are disrupting the traditional buttoned-up attorney lifestyle and world.

Corey: It’s wild to me, just to see how much of this winds up echoing my own experiences in dealing with, shall we say, some of the more I don’t use legacy, which is a condescending engineering term for ‘it makes money,’ but some of the older enterprise companies that had the temerity to found themselves before five years ago in somewhere that wasn’t San Francisco and build things on computers that weren’t rented by the gigabyte-month from various folks in Seattle. It’s odd talking to some of those folks, and I’ve heard from a number of people, incidentally, that they considered working with my company, but decided not to because I seem a little too lighthearted and that’s not how they tend to approach things. One of the nice things about being a boutique consultant is that you get to build things like this to let the clients that are not likely to be a good fit self-select out of working with you.

Matt: It’s identical to law.

Corey: Yeah. “Aren’t you worried you’re losing business?” Like, “Oh, don’t worry. It’s not business I would want.”

Matt: I’m okay with it. I’ll survive. Yeah, like, the clients that are great clients, you’re right, will be attracted to it. The clients that you never wanted to approach, they probably were never going to approach you anyways, are not [laugh] going to approach you. So, I agree wholeheartedly. I was always told lawyers are not funny. I’ve been told that jobs, conferences, events—

Corey: Who are you hanging out with doctors?

Matt: [laugh]. Dentists. The funniest of doctors. And I’ve been told that just lawyers aren’t funny, right? So, lawyers shouldn’t be funny; that’s not how they should present themselves.

You’re never going to attract clients. You’re ever going to engage in business development. And then I did. And then I did because people are attracted by funny. People like the personality. Just like you Corey, people enjoy you, enjoy your company, enjoy what you have to do because they enjoy being around you and they want to continue via, you know, like, business relationship.

Corey: That’s part of the weird thing from where I sit, where it’s this—no matter what you do or where you sit, people remain people. And one of the big eye-openers for me that happened, fortunately early in my career, was discovering that a number of execs at name brand, publicly traded companies—not all of them, but a good number; the ones you’d want to spend time with—are in fact, human beings. I know, it sounds wild to admit that, but it’s true. And they laugh, they tell stories themselves, they enjoy ridiculous levels of nonsense that tends to come out every second time I opened my mouth. But there’s so much that I think people lose sight of. “Oh, they’re executives. They only do boring and their love language is PowerPoint.” Mmm, not really. Not all of them.

Matt: It’s true. Their love language sometimes is Excel. So, I agree [laugh].

Corey: That’s my business partner.

Matt: I’m not good at Excel, I’ll tell you that. But I hear that as well. I hear that in my own business. So, I’m currently at a place called Lawtrades, and for the listeners out there, if you don’t know who Lawtrades is, this is the—I’m not a salesperson, but this is my sales spiel.

Corey: It’s a dating site for lawyers, as best I can tell.

Matt: [laugh]. It is. Well, I guess close. I mean, we are a marketplace. If you’re a company and you need an attorney on a fractional basis, right—five hours, ten hours, 15 hours, 20 hours, 40 hours—I don’t care, you connect.

And what we’re doing is we’re empowering these freelance attorneys and legal professionals to kind of live their life, right, away from the old guard, having to work at these big firms to work at big clients. So, that’s what we do. And when I’m in these conversations with general counsels, deputy general counsels, heads of legal at these companies, they don’t want to talk like you’re describing, this boring, nonsense conversation. We commiserate, we talk about the practice, we talk about stories, war stories, funny things about the practice that we enjoy. It’s not a conversation about business; it’s a conversation about being a human being in the legal space. It’s always a good time, and it always results in a long-lasting relationship that I personally appreciate more than—probably more than they do. But [laugh].

Corey: It really comes down to finding the watering holes where your humor works. I mean, I made the interesting choice one year to go and attend a conference for CFOs and the big selling point of this conference was that it counts as continuing professional education, which as you’re well aware, in regulated professions, you need to attend a certain number of those every so often, or you lose your registration slash license slash whatever it is. My jokes did not work there. Let’s put it that way.

Matt: [laugh]. That’s unfortunate because I’m having trouble keeping a straight face as we do this podcast.

Corey: It was definitely odd. I’m like, “Oh, so what do you do?” Like, “Oh, I’m an accountant.” “Well, that’s good. I mean, assume you don’t bring your work home with you and vice versa. I mean, it’s never a good idea to hook up where you VLOOKUP.”

And instead of laughing—because I thought as Excel jokes go, that one’s not half bad—instead, they just stared at me and then walked away. All right. Sorry, buddy, I didn’t mean to accidentally tell a joke in your presence.

Matt: [laugh]. You’re setting up all of my content for Twitter. I like that one, too. That was really good.

Corey: No, no, it comes down to just being a human being. And one of the nice things about doing what I’ve done—I’m curious to get your take on this, is that for the first time in my career doing what I do now, I feel like I get to bring my whole self to work. That is not what it means that a lot of ways it’s commonly used. It doesn’t mean I get to be problematic and make people feel bad as individuals. That’s just being an asshole; that’s not bringing your whole self to work.

But it also means I feel like I don’t have to hide, I can bring my personality with me, front and center. And people are always amazed by how much like my Twitter personality I am in real life. And yeah because I can’t do a bit for this long. I don’t have that kind of attention span for one. But the other side of that, too, is does exaggerate certain elements and it’s always my highs, never my lows.

I’m curious to know how you wind up viewing how you present online with who you are as a person.

Matt: That is a really good question. Similar. Very similar. I do some sort of exaggeration. The character I like to play is ‘Bad Associate.’ It’s, like, one of my favorite characters to play where it’s like, if I was the worst version of myself, in practice, what would I look like?

And those jokes to me always make me laugh because I always—you know, you have a lot of anxiety when you practice. That’s just an aspect of the law. So, for me, I get to make jokes about things that I thought I was going to do or sound like or be like, so it honestly makes me feel a little better. But for the humor itself and how I present online, especially on Twitter, my boss, one of my co-founders, put it perfectly. And we had met for a conference, and—first time in person—and he goes, “You’re no different than Twitter, are you?” I go, “Nope.” And he goes, “That’s great.”

And he really appreciated that. And you’re right. I felt like I presented my whole personality, my whole self, where in the legal profession, in private practice, it was not the case. Definitely not the case.

Corey: Yeah, and sometimes I talk in sentences that are more than 280 characters, which is, you know, a bad habit.

Matt: Sometimes. I have a habit from private practice that I can’t get rid of, and I ask very aggressive depo questions like I’m deposing somebody. If you’re listening in, can you write me on Twitter and tell me if you’re a litigator and you do the same thing? Because, like, I will talk to folks, and they’re like, “This isn’t an interview or like a deposition.” I’m like, “Why? Why isn’t it?” And it [laugh] gets really awkward really quickly. But I’m trying to break that habit.

Corey: I married a litigator. That pattern tracks, let’s be clear. Not that she doesn’t so much, but her litigator friends, if litigators could be said to have friends, yeah, absolutely.

Matt: My wife is a former litigator. Transactional attorney.

Corey: Yes. Much the same. She’s grown out of the habit, thankfully.

Matt: Oh, yeah. But when we were in the thick of litigation, we were actually at competing law firms. It was very much so, you come home, and it’s hard to take—right, it’s hard to not take your work home, so there was definitely occasions where we would talk to each other and I thought the judge had to weigh in, right, because there were some objections thrown, some of the questions were leading, a little bit of compound questions. So, all right, that’s my lawyer joke of the day. I’m sorry, Corey. I won’t continue on the schtick.

Corey: It works, though. It’s badgering the witness, witnessing the badger, et cetera. Like, all kinds of ridiculous nonsense and getting it wrong, just to be, I guess, intentionally obtuse, works out well. Something you said a minute ago does tie into what you do professionally, where you mentioned that your wife was a litigator and now is a transactional attorney. One thing they never tell you when you start a business is how many lawyers you’re going to be working with.

And that’s assuming everything goes well. I mean, we haven’t been involved in litigation, so that’s a whole subset of lawyer we haven’t had to deal with yet. But we’ve worked with approximately six—if memory serves—so far, not because we’re doing anything egregious, just because—rather because so many different aspects of the business require different areas of specialty. We also, to my understanding—and I’m sure my business partner will correct me slash slit my throat if I’m wrong—I’ve not had to deal with criminal attorneys in any interesting ways. Sorry, criminal defense attorneys, criminal attorneys is a separate setup for a separate story.

But once I understood that, realizing, oh, yeah, Lawtrades. You can find specialist attorneys to augment your existing staff. That is basically how I view that. Is that directionally accurate?

Matt: Yeah. So like, common issue I run into, right is, like, a general counsel, is a corporate attorney, right? That’s their background. And they’re very aware that they’re not an employment attorney. They’re not a privacy attorney. Maybe they’re not an IP attorney or a patent attorney.

And because they realize that, because they’re not like that old school attorney that thinks they can do everything and solve everyone’s problems, they come to Lawtrades and they say, “Look, I don’t need an employment attorney for 40 hours a week. I just need ten hours. That’s all I need, right? That’s the amount of work that I have.” Or, “I don’t have the budget for an attorney for 40 hours, but I need somebody. I need somebody here because that’s not my specialty.”

And that happens all the time where all of a sudden, a solo general counsel becomes a five or six-attorney legal department, right, because you’re right, attorneys add up very quickly. We’re like rabbits. So, that’s where Lawtrades comes in to help out these folks, and help out freelance attorneys, right, that also are like, “Hey, listen, I know employment law. I can help.”

Corey: Do you find that the vast slash entire constituency of your customers pretend to be attorneys themselves, or is this one of those areas where, “I’m a business owner. I don’t know how these law things work. I had a firm handshake and now they’re not paying as agreed. What do I do?” Do you wind up providing, effectively, introduction services—since I do view you as, you know, for dating with slightly fewer STDs—do you wind up then effectively acting as an—[unintelligible 00:18:47] go to talk to find a lawyer in general? Or does it presuppose that I know which end of a brief is up?

Matt: There’s so many parts of what you just said I want to take as well. I also liked that you didn’t just say no STDs. That was very lawyerly of you. It’s always, like, likely, right?

Corey: Oh, yes. So, the answer to any particular level of seniority and every aspect of being an attorney is, “It depends.”

Matt: That’s right. That’s right. It triggers me for you to say it. Ugh. So, our client base, generally speaking, our companies ranging from, like, an A round company that has a solo GC all the way up to a publicly traded company that has super robust legal department that maybe needs a bunch of paralegals, bunch of legal operations professionals, contract managers, attorneys for very niche topics, niche issues, that they’re just, that is not what they want to do.

So, generally speaking, that’s who we service. We used to be in the SMB space. There was a very public story—my founders are really cool because they built in public and we almost went broke, actually in that space. Which, Corey, I’m happy to share that article with you. I think you’ll get a kick out of it.

Corey: I would absolutely look forward to seeing that article. In fact, if you send me the link, we will definitely make it a point to throw it into the [show notes 00:19:58].

Matt: Awesome. Happy to do it. Happy to do it. But it’s cool. The clients, I tell you what, when I was in private practice when I was in-house, I would always deal with an adverse attorney. That was always what I was dealing with.

No one was ever—or a business person internally that maybe wasn’t thrilled to be on the phone. I tell you what, now, when I get to talk to some of these folks, they’re happy to talk to me; it’s a good conversation. It really has changed my mentality from being a very adverse litigator attorney to—I mean it kind of lends itself to a shitposter, to a mean guy, to a party clown. It’s a lot of fun.

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Corey: One area that I think is going to be a point of commonality between us is in what the in-and-out of our day jobs look like. Because looking at it from a very naive perspective, why on earth does what is effectively an attorney referral service—yes, which may or may not run afoul of how you describe yourselves; I know, lawyers are very particular about wording—

Matt: Staffing [laugh].

Corey: Exactly. Legal staffing. There we are. It doesn’t seem to lend itself to having a, “Head of Community,” quote-unquote, which really translates into, “I shitpost on the internet.” The same story could be said to apply to someone who fixes AWS bills because in my part of the industry, obviously, there is a significant problem with people who have large surprise bills from their cloud provider, but they generally don’t talk about them in public as soon as they become an even slightly serious company.

You don’t find someone at a Fortune 500 complaining on Twitter about how big their AWS bill is because that does horrifying things to their stock price as well as them personally, once the SEC gets involved. So, for me, it was always I’m going to be loud and noisy and have fun in the space so that people hear about me, and then when they have this problem, in the come. Is that your approach to this, or is it more or less the retconning story that I just told, and it really had its origins in, “I’m just going to shitpost. I feel like good things will happen.”

Matt: Funnily enough, it’s both. That’s how it started. So, when I was in private practice, I was posting like crazy on—I’m going to say LinkedIn for the third time—and again, I hope somebody sends a nasty message to me about how bad LinkedIn is, which I don’t think it’s that bad. I think it’s okay—so I was shitposting on LinkedIn before probably many folks were shitposting on LinkedIn, again like Alex, and I was doing it just because I was tired of attorneys being what we described, this old guard, buttoned up, just obnoxiously perfect version of themselves. And it eventually led itself into this career. The whole journey was wild, how I got here. Best way to describe it was a crazy trip.

Corey: It really is. You also have a very different audience in some ways. I mean, for example, when you work in the legal field, to my understanding from the—or being near to it, but not within it, where you go to school is absolutely one of those things that people still bring up as a credential decades later; it’s the first thing people scroll to on LinkedIn. And in tech, we have nothing like that at all. I mean, just ask anyone of the random engineers who talk about where they used to work in their Twitter bio: ex-Google, ex-Uber, et cetera.

Not quite as bad as the VC space where it’s, “Oh, early investor in,” like, they list their companies, which of course to my mind, just translates directly into, the most interesting thing about you is that once upon a time, you wrote a check. Which yeah, and with some VCs that definitely tracks.

Matt: That’s right. That’s a hundred percent right. It’s still like that. I actually saw a Twitter post, not necessarily about education, but about big law, about working in big law where folks were saying, “Hey, I’ve heard a rumor that you cannot go in-house at a company unless you worked in big law.” And I immediately—I have such a chip on my shoulder because I am not a big law attorney—I immediately jumped to it to say, “Listen, I talk to in-house attorneys all the time. I’m a former in-house attorney. You don’t have to work with big law. You don’t have to go to a T-14 law school.” I didn’t. I went to Florida State University in Tallahassee.

But I hear that to this day. And you’re right, it drives me nuts because that is a hallmark of the legal industry, bragging about credentials, bragging about where I came from. Because it also goes back to that old guard of, “Oh, I came from Harvard, and I did this, and I did that,” because we love to show how great and special we are not by our actual merits, but where we came from.

Corey: When someone introduces themselves to me at a party—which has happened to me before—and in their introduction, they mention where they went to law school, I make it a point to ask them about it and screw it up as many times in the rest of the evening as I can work in to. It’s like they went to Harvard. Like so, “Tell me about your time at Yale.” “Oh, sorry. I must have forgotten about that.” Or, “What was the worst part about living in DC when you went to law school?” “Oh, I’m sorry. I missed that. You went to Harvard. How silly of me.”

Matt: There’s a law school at Dartmouth [laugh]?

Corey: I know. I’m as surprised as anyone to discover these things. Yeah. I mean, again, on the one hand, it does make people feel a little off and that’s not really what I like doing. But on the other, ideally, it’s a little bit of a judgment nudge as far as this may not sound the way that you think it sounds when you introduce yourself to people that way.

Matt: All the time. I hear that all the time. Every so often, I’ll have someone—and I think a lot of the industry, maybe just the industry where I’m in, it’s not brought up anymore. I usually will ask, right? “Hey, where do you come from?” Just as a conversation starter, “What firm did you practice at? Did you practice in big law? Small law?”

Someone once called it insignificant law to me, which hurts because I’m part of insignificant law. I get those and it’s just to start a conversation, but when it’s presented to me initially, “Hey, yeah, I was at Harvard,” unprompted. Or, “I went to Yale,” or went to whatever in the T-14, you’re right, it’s very off-putting. At least it’s off-putting to me. Maybe if someone wants to tell me otherwise, online if you went to Harvard, and someone said, “Hey, I went to Harvard,” and that’s how they started the conversation, and you enjoy it, then… so be it. But I’ll tell you, it’s a bit off-putting to me, Corey.

Corey: It definitely seems it. I guess, on some level, I think it’s probably rooted in some form of insecurity. Hmm, it’s easy to think, “Oh, they’re just completely full of themselves,” but that stuff doesn’t spring fully formed from nowhere, like the forehead of some God. That stuff gets built into people. Like, the constant pressure of you are not good enough.

Or if you’ve managed to go to one of those schools and graduate from it, great. The constant, like, “Not everyone can go here. You should feel honored.” It becomes, like, a cornerstone of their personality. For better or worse. Like, it made me more interesting adult if it made my 20s challenging. I don’t have any big-name companies on my resume. Well, I do now because I make fun of one, but that’s a separate problem entirely. It just isn’t something I ever got to leverage, so I didn’t.

Matt: I feel that completely. I come from—again, someone once told me I worked in insignificant law. And if I ever write a book, that’s what I’m going to call it is Insignificant Law. But I worked the small law firms, regional law firms, and these in Tallahassee and I worked in South Florida and nothing that anyone would probably recognize in conversation, right? So, it never became something I bring up.

I just say, “I’m an attorney. I do these things,” if you ask me what I do. So, I think honestly, my personality, and probably the shitposting sprung out of that as well, where I just had a different thing to talk about. I didn’t talk about the prestige. I talked about the practice, I talked about what I didn’t like about the practice, I didn’t talk about being on Wall Street doing these crazy deals, I talked about getting my ass kicked in Ponce, Florida, up in the panhandle. For me, I’ve got a chip on my shoulder, but a different kind of chip.

Corey: It’s amazing to me how many—well, let’s calls this what we are: shitposters—I talk to where their brand and the way that they talk about their space is, I don’t want to say rooted in trauma, but definitely built from a place of having some very specific chips on their shoulder. I mean, when I was running DevOps teams and as an engineer myself, I wound up continually tripping over the AWS bill of, “Ha, ha. Now, you get to pay your tax for not reading this voluminous documentation, and the fine print, and with all of the appendices, and the bibliography, and tracked down those references. Doesn’t it suck to be you? Da da.” And finally, it was all right, I snapped. Okay. You want to play? Let’s play.

Matt: That’s exactly right. There’s, like, a meme going around. I think it actually saw from the accounting meme account, TB4—which is stellar—and it was like, “Ha, I’m laughing because it hurts.” And it’s true. That’s why we all laugh at the jokes, right?

I’ll make jokes about origination credit, which is always an issue in the legal industry. I make jokes about the toxic work environment, the partner saying, “Please fix,” at three o’clock in the morning. And we make fun of it because everyone’s had to deal with it. Everyone’s had to deal with it. And I will say that making fun of it brings light to it and hopefully changes the industry because we all can see how ridiculous it is. But at least at the very beginning, we all look at it and we say, “That’s funny because it hurts.”

Corey: There’s an esprit de corps of shared suffering that I think emerges from folks who are in the trenches, and I think that the rise of—I mean some places called the micro-influencers, but that makes me want to just spit a rat when I hear it; I hate the term—but the rise of these niche personalities are because there are a bunch of in-jokes that you don’t have to be very far in to appreciate and enjoy, but if you aren’t in the space at all, they just make zero sense. Like when I go to family reunions and start ranting about EC2 instance pricing, I don’t get to talk to too many people anymore because oh my God, I’ve become the drunk uncle I always wanted to be. Goal achieved.

Matt: [laugh].

Corey: You have to find the right audience.

Matt: That’s right. There is a term, I think coin—I think it was coined by Taylor Lorenz at Washington Post and it’s called a nimcel, which is, like, a niche micro-influencer. It’s the worst term I’ve ever heard in my entire life. The nimcel [laugh]. Sorry, Taylor, it’s terrible.

But so I don’t want to call myself a nimcel. I guess I have a group of people that enjoy the content, but you are so right that the group of people, once you get it, you get it. And if you don’t get it, you may think some parts of it—like, you can kind of piece things together, but it’s not as funny. But there’s plenty of litigation jokes I’ll make—like, where I’m talking to the judge. It’s always these hypothetical scenarios—and you can maybe find it funny.

But if you’re a litigator who’s gotten their ass kicked by a judge in a state court that just does not like you, you are not a local, they don’t like the way you’re presenting yourself, they don’t like your argument, and they just dig you into the ground, you laugh. You laugh because you’re, like, I’ve been there. I’ve had—or on the flip, you’re the attorney that watched your opposing counsel go through it, you’re like, “I remember that.” And you’re right, it really you get such a great reaction from these folks, such great feedback, and they love it. They absolutely love it. But you’re right, if you’re outside, you’re like, “Eh, it’s kind of funny, but I don’t really get all of it.”

Corey: My mother approaches it this way whenever she talks to me like I have no idea what you’re talking about, but you seem to really know what you’re talking about, so I’m proud of you. It’s like, “No, Mom, that is, like, the worst combination of everything.” It’s like, “Well, are you any good at this thing?” “No. But I’m a white man, so I’m going to assume yes and the world will agree with me until proven otherwise.” So yeah, maybe nuclear physics ain’t for you in that scenario.

But yeah, the idea of finding your people, finding your audience, before the rise of the internet, none of this stuff would have worked just because you live in a town; how many attorneys are really going to be within the sound of your voice, hearing these stories? Not to mention the fact that everyone knows everyone’s business in some of those places, and oh, you can’t really subtweet the one person because they’re also in the room. The world changes.

Matt: The world changes. I’ve never had this happen. So, when I really started to get aggressive on, like, Twitter, I had already left private practice; I was in-house at that point. And I’ve always envisioned, I’ve always, I always want to, like, go back to private practice for one case: to go into a courtroom in, like, Miami, Florida, and sit there and commiserate and tell the stories of people again like I used to do—just like what you’re saying—and see what everyone says. Say, “Hey, I saw you on Twitter. Hey, I saw this story on Twitter.”

But in the same breath, like, you can’t talk like you talk online in person, to some degree, right? Like, I can’t make fun of opposing counsel because the judge is right there and opposing counsel was right there, and I’m honestly, knowing my luck, I’m about to get my ass kicked by opposing counsel. So, I probably should watch myself in that courtroom.

Corey: But I’m going to revise the shit out of this history when it comes time to do my tweet after the fact. “And then everybody clapped.”

Matt: [laugh]. I found five dollars outside the courtroom.

Corey: Exactly. I really want to thank you for spending so much time chatting with me. If people want to learn more and follow your amazing shitpost antics on the internet, where’s the best place for them to do it?

Matt: Corey it’s been an absolute pleasure. Instagram, TikTok, Twitter, LinkedIn. For everything but LinkedIn: @ItsMattsLaw. LinkedIn, just find me by my name: Matt Margolis.

Corey: And we will put links to all of it in the [show notes 00:33:04]. Thank you so much for being so generous with your time. It’s appreciated.

Matt: I have not laughed as hard in a very, very long time. Corey, thank you so much.

Corey: Matt Margolis, Head of Community at Lawtrades. I’m Cloud Economist Corey Quinn and this is Screaming in the Cloud. If you’ve enjoyed this podcast, please leave a five-star review on your podcast platform of choice, whereas if you’ve hated this podcast, please leave a five-star review on your podcast platform of choice along with an angry, insulting comment that you’ve drafted the first time realized, oh wait, you’re not literate, and then hired someone off of Lawtrades to help you write in an articulate fashion.

Corey: If your AWS bill keeps rising and your blood pressure is doing the same, then you need The Duckbill Group. We help companies fix their AWS bill by making it smaller and less horrifying. The Duckbill Group works for you, not AWS. We tailor recommendations to your business and we get to the point. Visit to get started.

Announcer: This has been a HumblePod production. Stay humble.
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