#1 - Ironclad's Alex Su Talks TikTok, Trolls, and Career Changes

What does it take to run a high performing business? Strategy, finesse and a lot of advice from people who've been there, done that before. I'm Mary o'.

Carroll.

Join me on my Pearls on Gloves off podcast to hear from the leaders building some of the most innovative companies today. We'll take a high value, no holds barred approach to find out what works. See you there.

Hello, everyone and welcome to Pearls on Gloves Off. Thank you for joining us. I'm your host, Mario Carroll, and today I have with me Alex Hsu. You may know Alex from his work as head of community development at Ironclad, but let's be honest, you probably know him as Legal tech bro on TikTok, because that's probably where he's known for his best work. Alex has over 170,000 followers on social media and is well known as Legal's first and likely only real influencer. Welcome, Alex.

Thank you, Mary. I'm so excited to be here. I'm so excited about this. Yeah, this is so cool.

So I would love to take credit for hiring you onto the community team here at Ironclad, but let's be honest, we were both hired concurrently to build out this function together. Our founder, our CEO, Jason Baymig, in all his brilliance, actually hired the two of us at the same time. Right. With the foresight of knowing that if he put us together, we'd make a great team. And needless to say, as always, he was absolutely right on that. So I know most people only see the social media aspect of our jobs and they kind of assume that's what we do all day. And while we both know that to only be a fraction of what we do, let's let everyone keep thinking that, because I like the mental image that you're out there just doing TikTok videos all day.

Yeah, I like that image too.

Yeah. Do you remember how we actually first met?

I do. So, Mary, I had been following you ever since I got into legal tech in 2016. Everyone told me about Clock. I saw you speak in front of the entire audience and so I knew who you were. And so I remember people telling me, there's a story of a couple of friends who told me one day they said to me, hey, we just met Mario Carroll from Google, from Clock. And we were all like, oh, what is she like? We would talk about these things. And so, Mary, I had known about you for many years. I remember when we first met was on Zoom, because this was probably in the pandemic maybe a year into the pandemic. And I had, we might go on my platform and I was like, well, I think it'd be cool to meet Mary. So I sent you a message, a dm and said, hey, would you like to meet? And you graciously said yes. And so we got to meet on Zoom. And that was so cool. And I never imagined we'd be working together like this, but that's. I don't know if you remember that conversation, Mary.

Yeah. And you reached out to me, actually through LinkedIn, right? Through a direct message on LinkedIn, which, which I think is so cool given, you know, the, the power of community and power of social media, that, that's really how we became first acquainted, was through social media.

Yeah, it's, it's funny, right before, before Community, I was a salesperson and we, we always leverage LinkedIn for that reason. Like, when I first started getting active on LinkedIn, I realized it was a great way to connect with people. That was warmer than like an email, you know, like when you send a cold email, it almost seems, I don't know, impersonal. More impersonal. So naturally I knew that if there was someone I really wanted to meet, I was going to use LinkedIn. And that's why I reach out to you on LinkedIn on VMS.

But it works, right? I mean, you and I both know that we spent by that time a year sitting in front of our Zooms all day in our home offices and weren't able to get out and meet new people. And I think that it was really a lifesaver during that time, how many acquaintances, people, relationships that I built through LinkedIn and through people just reaching out and saying, hey, would you like to have coffee over Zoom? Right. And often, most of the time, I'd say almost all the time. I would say yes, because there was something interesting there or someone interesting to meet. And I'm sure you built a lot of relationships during the pandemic that way as well, right?

I did. During the pandemic, it was the same thing for me. I was like, how am I going to meet people? You know, one on one, Zooms was, was kind of what I shifted to. And so, and people were open to it. There was a moment, if you remember, I don't know if you remember, but at the very beginning, like, everyone was into meeting each other and just like really open to doing that. When, before I think the pandemic, people were busy and they were like, you know, not sure, you know, oh, I don't know about scheduling, but there was this moment where it was. Everyone was so open to meeting each other. It's not unlike, you know, going to a conference or, you know, just there's this. This energy where people just want to talk to each other.

Yeah. And I think that real friendships came through. I mean, like, I will just give you an example. We were just at Clock recently, and I met some people for the first time in person and hugged them, and people around us were like, wait, I thought you guys were real friends from a long time ago. And I'm like, no, we are. We just met via LinkedIn and Zoom and we are real friends, but we've never had the opportunity to meet in person. But they're genuine friendships, right?

Yeah. There's some people who I feel like I know better than people that I. I've had in person friendships with for a long time. I mean, I think that it's a totally new dimension, and I think at first it feels kind of a little different, but as you continue your relationship, whether through LinkedIn or, you know, Zoom or anything else, like real professional and personal relationships get. Get built.

Yeah. So you have a trillion followers on social media. I saw you at Clock, which was recently, and people treated you like a celebrity. It was. It was very fun to watch in a different celebrity in a way that it's almost like when you see, you know, a Tom Cruise walking down the street. You don't want to, like, mob them, but everyone behind you is kind of pointing, going, oh, my God, there he is. That's the guy. That's the TikTok guy. So I thought that was very cool. How was that for you, as your first experience in a legal environment? Coming out of the pandemic, that kind of made you. Because you started your whole social media, I don't know what to call it, your whole thing during the pandemic. And so that was your first opportunity to kind of be in front of people who would know who you were.

Yeah, Mary, it was so surreal. So, you know, I have a lot of followers now. I had kind of a good number of followers and connections before the pandemic. The last one I went to was Legal, legal week in 2020. A few people said, hey, you know, I've seen your stuff on LinkedIn. And so it was very different when I went to Clock last week. It was surreal because there were people who recognized me because before I was just known as my profile picture and some text posts, but because of TikTok, people recognize my face. And so even if they don't know who I Am. They're like, you're that guy.

You're that guy.

I've seen your stuff. I've seen your stuff. And so it was such a different vibe. And, you know, I thought it was really cool in the beginning when you and I kind of met up before at the very early part of the conference, and I got to see you walk through the crowds, and I was always wondering, like, do people know who I am? But clearly everyone knew who you were and were coming up to you and shaking hands and wanting to take pictures with you. I mean, I'm very curious. Like, how is it like for you being back at Clock ever since, you know, the Pandemic and joining Ironclad?

You know, it feels like home. Like, Clock is home. That is my baby. It is our community. It's our people, and they're truly, truly old friends. So, yes, I mean, I've been in that space physically and in person, so absolutely. People recognize me and know who I am, but they're genuine friends. And what I. I mean, I think Clock is so special because we're a community that genuinely wants to see each other and be together in person, which, you know, is a testament to how big the event was last. The last event was. But, yeah, it's. It felt kind of the same. You know, I'm no longer involved in it directly, but it will always be very, very special to me. So, yeah, I will. I will always have a big, big place for Clock in my heart and a big champion of. Of what they do.

I mean, it was so cool to see you talking to people like old friends, and you've been doing this for a long time. My platform just really grew only in the last two years. And so I remember I would be walking around being like, do they know who I am? Do they not know who I am? And I, you know, I avoid con icon. I don't want to look at someone, and then they look at me and, like, I mean, what would I say? Hi. So it was kind of like, for me, trying to feel the situation out, but it was really nice. Like, a lot of people knew who I was, and I think that it's very flattering when someone says, can I take a picture with you? And because in my head, I'm like, oh. Oh, my God. They, like, they know who I am. That's. That's nice. That's cool. And I'm not used to that because, you know, as I mentioned, like, before, I was a salesperson at a, you know, at a tech company, and I feel like, it's different. Like, I wasn't really well known, and people didn't know who I was. And now last week, it was very different.

Yeah. Well, so let's talk about your journey a little bit, because I know you've talked about it in a lot of other settings, but maybe folks who are tuning in here are not aware you were trained as a lawyer. We call you recovering lawyers. Right. And then you went into legal tech in more of a sales capacity. What was it like? Or what made you kind of make that jump into legal tech in the first place?

Yeah, so I never imagined I would go to legal tech. And, you know, at the time, I was living in the Bay Area, and I knew that tech was a big move. Like, it was a. It was a growing space. And I thought, well, at the time, I had gone through a couple of setbacks. Like, I've been let go from a job. I started my own firm. It didn't work out. So I was like, I need a win. I need to do something that I feel like I could do well at. And, you know, just through those experiences, I realized, like, I'm not the guy who, like, will sit in a room 40 hours a week typing away, 60 hours a week typing away, researching. I want to be out there. I want to meet people. I think that I might be good at sales because, like, previously, like, I done this. I had done this camp, worked on this political campaign between my clerkship and the firm, and it turned out I learned that I was really good at cold calling, which is kind of an unusual thing for a lawyer. Like, lawyers generally don't do that kind of thing. So. So I knew that I was kind of different. And I was like, well, if I could take my experience and combine it with doing something that I was, you know, possibly good at, like sales, I think I could be successful. And so I was like, all right, I'll start from the bottom. I'm okay with that, you know, And I was looking at different opportunities. I chose E Discovery because I knew E Discovery. I was a litigator before. I knew so many different platforms for E Discovery. I knew the work that needed to be done. So I was like, I do E Discovery and do sales. I think maybe I could be good at it. So that was kind of what prompted me to get into it. I was there for three years at that first startup. It was such a good experience. I learned so much and from so many people. And I remember at that time, that was when I first heard about, you know, you and Clock and, and like the entire ecosystem of legal, like law firms, corporate legal and tech vendors and all that, it was, it was such an educational experience and I feel like I really made the right decision.

Yeah. What year was that about that you jumped into Legal Tech?

It was the summer of 2016.

Ah, the birth of Clock. The explosion of Legal Ops, the explosion of legal tech and investment into the space. That's really exciting. Good timing. Way to time that just right.

My timing. I mean, I was so lucky. I feel like we all always, we all work hard and, you know, everyone tries to do well, but the timing plays a big role in a lot of these things. Yeah, I mean, I, I never imagined that that's what would happen. I just thought, you know, it was a hunch. I was like, I might be good at this thing and I have something to contribute. And I got to imagine it was probably something similar for you when you got into, into Google. Like Legal Apps wasn't even a thing, right?

Yeah, Legal Ops was not a thing. I, I joined Google in 2008 and I mean, you, you could Google search it and there was nothing that came up, like nobody. It wasn't a role yet, you know.

Yeah.

And I kind of think, you know, just the parallel to what we're doing right now and building community. Right. It's so similar. So, side note, I remember listening about 10 years ago to someone talk about Gen Z and the future of Gen Z and the careers for them. And the speaker had said something to the effect of 80% of Gen Zers 10 years ago would have jobs that don't currently exist. I was like, oh, that's so crazy. And then, you know, and then I realized, oh, well, the job that I took at the time was brand new and didn't exist. And interestingly, now we're doing the same thing over again with Community, which is this job that people are like, what is this job? Right. But it's exploding. You see all these companies hiring for Community and we know that it's going to be a really big role in the future. So yeah, it was a risk. It was exciting and new to me. I love unchartered territory. Like, I love a role that's completely undefined because that lets you be super creative and find problems and fix them or do different things. And no one can tell you that's not the way it's supposed to be done. Right. Lets you just have Runway and space to do whatever you want. And I think that's also what you and I are really loving about. Our current roles.

Oh, for sure. And you know, one of the things I always hated about working in big law was that you had to wait. When you have an established, I don't know, career track you want to call it, or like an established space, like really smart and talented people come in and they do all the work and then they kind of take the leadership positions. And this is true in law and probably true in other places, but then to move up as a young, up and coming professional, you have to wait for them to retire or to step aside or maybe one of them to be nice, to give you an opportunity. Whereas in technology, in startups and in community, like, there's so much that has to be figured out. There's more problems than solutions. So. So it's just different. There's more opportunity, in my opinion.

Yeah, absolutely. And so what made you take the next shift in your career? You were in legal tech, you were doing Ediscovery. You made a pretty major shift. Being someone who is a litigator. You don't have a background in commercial law or contracting. What made you kind of move into that space?

It was just the opportunity, Mary. I saw where the puck was headed. And not because I'm like supervisionary, but people were telling me I was getting advice, I was hearing things on the ground about how contracts touched every part of the business and it was going to be in the upswing. And it was this is in 2019. So I'd been in eDiscovery for three years and so I knew that contracts had more opportunity. Like, if you look at Ediscovery, it had been around for decades. And so similar to law, there's people who have established themselves. There's like, it's hard to grow along with it because it was so established, whereas in contracts it was still being figured out. I remember following Ironclad from the very beginning, when we have a sales leader here, Mel Wong, who I heard on a podcast talking about going from law to sales. And at the time, I think she was at some other startup, some other tech company. And I was like, oh my God, she has such an inspirational journey. Let me look her up online to see where she's at. And I remember I found Ironclad and there were like seven or eight people working there. And I was like, I don't know what contracts are. Like, I was a litigator, but this seems cool. Let me follow along and see what's happening in that world. And I saw the space kind of play out. And so in 2019, I said, I'm going to make the jump. And I thought about joining Ironclad, but I didn't. And so, you know, I didn't end up doing until obviously last year, but I've been following the space in the company for a while.

Well, you are like, so hip and so cool. So you knew that legal tech was going to take off? You knew that contracting was going to take off. I know you talk about NFTs all the time now, but you also somehow predicted TikTok and being a legal influencer. I mean, your timing on that couldn't have been more perfect. I'm going to have to ask you for some stock tips after this recording.

I guess. Memes. I remember seeing my first memes and I remember thinking like, I don't really get it, I guess it's funny, but you've really taken that in the whole TikTok craze before, TikTok was a thing and it of course taken off. And, you know, you're very humble here, but everybody knows who you are and, like, loves your videos and you are extremely talented. There's been a lot of people kind of trying to follow in your footsteps, which is great. But I mean, I have to say, and I've told you this many, many times, like, the level of Alex Sue's facial acting is just amazing. Like, nobody comes close. It's Oscar worthy. So what was like, the first thing you decided to try? What was. Do you remember your first meme or video?

Yeah, I do. So. Well, first of all, thank you for saying all that because I don't actually think my timing is that impeccable like you. I kind of like to go where it's still kind of the Wild west and things aren't figured out and inevitably some of these things will take off, like just like Legal Ops and Clock, you know, and. Yeah, and when I wanted to get into legal tech back in 2016, I mean, my lawyer friends were like, what are you doing? This is not a charted career path. Are you crazy? Are you not going to be a partner somewhere? So I do think that doing something weird that isn't cool yet is just a necessary part of it because it's before it's cool, Right? But over the years, it's like become a muscle where you can kind of start seeing some patterns and when things kind of start seeing some traction, you can see it. And I think the thing people don't understand is that instead of trying to make predictions, I mean, for me, I listen to what people are saying. I listen to Rumors I listen to, like, things that people are feeling. And then I try most things and then abandon others. Like, like when the pandemic hit. I did a lot of weird things online, which include TikToks. But I also, like, you know, started a meetup. I started putting out threads on LinkedIn, trying to connect people together. I can't remember all of them. I tried a lot of things and most of them didn't work out. The ones that did that, I felt like, got a reaction from the world. Like, I stuck with those things. And so, like my first TikTok, I remember it wasn't even a TikTok at the time. I took a laptop and I used Zoom to record myself acting something out. And then I used iMovie, the free program for video editing on Mac. And I just made this 30 second video of a young associate at a law firm who knows nothing about anything. And the partner would speak to the associate and I guess the partner, the words would come out in a weird jumble. And it was very corny, it was very silly, but the reaction was unexpected. People got really into it because no one had done video humor on LinkedIn. And so I started, I did that one, I did another one and I did another one. And then that's when people started telling me, hey, you should check out TikTok. And I remember hearing about TikTok at the time because my wife had told me. She said, I downloaded this app. It's TikTok. It's like people are dancing, people are lip syncing. It's all teenagers. And I was like, that doesn't sound like my thing. I'm a professional, I don't want to get involved with that. But people who are partners at firms and GCs would tell me, hey, Alex, you need to get on TikTok. And so that's why I started doing TikTok. Like, again, listening to what people are telling me, doing something weird that's hard to explain to your friends. And I just kind of leaned into it and got very lucky.

Yeah. And now, like doing this as part of your day job, because every time you mention your wife, I have to make sure that I tell everyone, tell us. Because this mental image for me is just so lovely. What is it that your wife does for a living?

My wife is a pediatric cardiologist. She met when I was in law school and she was in medical school. And, you know, at the time I was like, well, I want to, you know, I would tell her, I'm like, I'm going to have A legal career. I'm going to be a litigator. I want to be a federal prosecutor. I might be a partner at a firm one day. And so it's just funny how things have happened in my life where now I'm doing tiktoks and fun things and I have a very non serious job. Well, she, you know, she's a pediatric cardiologist. She has a very serious job. She's saving lives.

I mean it could not get more serious. Right. And I always have the image of like her coming home from work and being like, hi honey, I'm home. And you're there with your Fisher, Fisher Price phone and making videos. I love it.

I mean there was one day when literally she was, she got off of work, we were trying to think about doing something with NFTs and I was in the corner using our daughter 3 year old's watercolors. I was painting something and, and she's like, what are you doing? And I said oh, don't worry, I'm just working. I'm just working. And I was like painting this like cartoon. It was so. And she's like, I don't understand your job.

We have the best job, Alex. We have the best jobs. We can't, we can't tell anyone. It's like our secret. So on that though, like, because you're such a public figure and you know, I have talked about this because I can relate to it as well. There's you know, some stuff that comes with the territory of putting yourself out there, which is the, the troll. Right. The person who's going to not like anything you do or just be nasty and post kind of negative things in response to what you do. And how do you deal with that? Like that that's got to take. You know, it doesn't matter how thick skinned you are, it takes a little bit of a personal toll. Right.

Yeah.

Has that happened?

It has and it's been better as of late because I don't know if it's because on social media people are realizing that they're maybe not as anonymous as they think. The worst comments come and the worst trolls come when people feel like they can say something and then run away.

Yeah.

And they say some pretty mean things. So what I love about LinkedIn especially, people are generally very positive and collaborative. And so when someone sees someone else being mean to me or to anyone else really, they will defend. And so I've come to realize when the trolls come, you got to kind of let it go a bit. Unless it's like really important. You feel like it's really important for you to respond, but most of the time you let it go because other people will, will defend you. If you've been good to your community and they see that you're trying to, trying to help everyone out, they will defend you. And so that, that's been very helpful to me. I've seen it, I've seen it happen a couple times, but I don't, certainly don't feel like I know everything about how to handle trolls. It is something I'm trying to figure out. And I'm curious if you know, as someone who's been public for, for a lot longer, a public figure for a lot longer, what advice do you have about trolls? Because I know a lot of people on social media are wondering how to navigate all this.

I think you're right. I mean, I'm Most active on LinkedIn. And you're right, it is a professional space. It's not anonymous. So people are generally pretty good about not writing nasty things. But aside from that, and even when it's not to your face, you know, you hear things that people are. You're not going to always make everyone happy and there's always going to be folks that are sort of, you know, haters going to hate, as they say. I think I learned pretty early on in my career, even earlier in my childhood, that people can say whatever they want. Like, not everyone's going to like you. You're not going to please everyone all the time and you can just be you and do you and they don't like it too bad. You know, I'm going to find friends elsewhere and find other people that are part of my community and a part of, like, people who lift me up and make me happy and I make them happy. And that's a, a good circle to be in. And you don't need to waste time or energy or headspace with folks that are going to bring you down because they're, they're going to be there. And as long as you know that you're doing something good and you're not trying to do anything bad, then let it kind of roll off your back if you can. It's, it's, there's no good can come of kind of dwelling on it.

I think that's such great advice in so many dimensions, too, because I don't think I've told you this story. I got to tell you this one because when I started posting and growing my audience, it wasn't just trolls trolling me but there were people talking about what I was saying on other platforms. Like, a friend forwarded me a Reddit thread where somebody said something pretty harsh about me, and, you know, it made me feel a little bit sad. But over time, obviously, I grew my platform and the mean comments went away. And I once did a presentation at Yale Law School, and we wanted to kind of share about how it was in the beginning of our journeys for me, my content creation journey, and then for Jason, building Ironclad. And what I found was interesting was one of the slides, he shared something that these anonymous posters would use that when. When. When Ironclad first came out, people were like, saying, this company is a. This is a. This is a stupid product idea. This company will never succeed. They were saying really mean things. Yeah. Which made me realize, like, there's some parallels here. Like, I think when anyone is trying to do something new and different and is kind of seeing some traction, the haters will always come out. It's tempting to, like, kind of want to argue with them, but there's no better way to, like, clap back at them than to be successful and kind of, like, keep moving forward in a positive way. And. And seeing that from Jason made me really inspired because I was like. Like, it's not just me, like, everyone who's done something significant. And I think, you know, when I heard that people were potentially giving you a hard time, I was like, I can't believe that. But, like, I think everyone, when they start off, there's just going to be haters out there, and you got to keep on moving on.

Yeah, I think you're right. I think you're right. Whenever you're doing something new or different, there's always going to be someone who doesn't like what you have to say. So be it.

Right.

We move on.

Yeah, absolutely. So, Mary, at clock, you gave this talk about from Legal Ops to Strategic Ops, and I thought that was super, super interesting because, you know, a lot of people talk about efficiency, but I think your message was more important than that. It was big. It was broader than that. And I thought, like, where did this idea come from? How did you start thinking about this?

Oh, I think, you know, I've been watching Legal Ops for a long time. I mean, since its inception, and trying to stay ahead of the trends and know where the industry is going as well as where the profession is going. It's. It's always been really important to me that Legal Ops is a career. It's a profession that it grows in its stature. You know, that it's not like an entry level job that dies in the back office. And I think that it's grown incredibly in its prevalence. Right. We're seeing legal ops exploding in companies of every size and every industry and all over the world. And that's fantastic. But now that we've kind of broadened the scope of the role to go beyond financial planning into now systems and tools to process improvement, to project management, to all these knowledge management and practice management, that you start to have a period or I think we're in a juncture where we can either be defined in one of two ways. We can either go down the path of you start to hire people who are able to run the day to day trains of the operations. And I consider that's really important, but that is where it stops versus you start to hire in addition the leaders who have more business acumen, who have more seniority and experience and who can actually be leaders in a strategic way for the business, for the general counsel, for the CEO. To me it's really important again that there is a career path. And so we have to define the role now before it gets stuck, you know, and we have to be the ones who define it or it gets, you know, I would say gets defined for us. So the strategic role is absolutely the next wave of where legal ops can and should go. You can't get there without building upon a foundation. So you've got various levels or layers of value and you've got to start with the foundation of being an optimizer. And that is about creating day to day, running the trains, making sure that the function has got smooth processes, smooth technology, things that make life and work better for everyone. But you can't stop there. I think the danger is you get stuck there because there's so much work there and there's so much to do that you can't come up for air, essentially. But what I try to tell folks is as you're putting those processes in place, make sure you're always thinking about how are those going to get maintained, they cannot be maintained by you. So put that system in place, then move on and then you start to move up into the next layer of value which is accelerating business and thinking about how you can help the rest of the company go faster and do things better. And then finally it's the wayfinder role, which is kind of the new emerging strategic leader of the company. And that's where I think we have to go. We have to push people towards that. And legal ops is in such A perfect and wonderful space seat to do that. Because you're in legal, which is the one part of the company that touches everything. You know what's happening with the business. You see the sales opportunities, you see the partnerships before anyone else does. You're working with the product teams. You know what's coming on the product side, you know it's coming from real estate. Right. Are you buying a giant property in, in San Jose to build out a new campus? Well, you know, you're going to hire a thousand engineers. You know what's happening kind of all across the company before anyone else does. And what I had found in my experience is that people in my old team in Legal Ops who were exposed to everything that was happening, we would sit around and say, ah, you know, what the company should really do is XYZ and we should be doing this with this product and we should really get out into this audience there because this is happening competitively. And I realized we have really great perspective, but we're not doing anything because we feel like we're in the backseat. Right. We're in the back office. We're. We're supposed to just take direction from everyone else. But I really think that Legal Ops is in a unique position to be able to see everything happening, have the data in their hands, surface it to other teams, and then suddenly be able to show where the company can go and what different ways can be taken to get there. I think it's super exciting. I think it's a really positive thing. It shouldn't intimidate anyone. I mean, it's early days, but we have to continue to push ourselves and challenge ourselves to go into that direction.

Yeah. And I wholeheartedly buy into that message. And I think that what I find interesting is that when you talk about corporate legal as a function, I think, you know, there's the old saying that people call it like a cost center or department of. No, I don't know where that comes from. But I remember when I was in law school, people would tell me, hey, you might think working at a corporate legal department is cool because it's a good lifestyle, but you're always going to be viewed as a cost center and so you kind of want to avoid that. I kind of took that for granted. But kind of after talking to so many in house lawyers and people who are on the ground floor, I think legal is so interestingly positioned, just like you say, like you can see everything. And I think part of it is that there's this perspective that legal work should Always be reactive. Like, you know, you have a problem, I'm going to solve it for you. And the way I bring value is by giving you a very specific, comprehensive answer. And I feel like that's not what the business world wants. It's to move faster, to be enabled. It's not like giving you the full legislative history or, you know, legal history of so and so concept. And I think that is in part probably driven by the personalities of the people who end up running or, you know, or involved in the legal department, like people who came up in law firm firms. And we're trained to get specific answers. I think it's really cool to see that. This shift that I think you're really highlighting, because corporate legal is very different than law firms. It's just very different. Right.

I want to react to a couple things you said. One which is why is it the office of no. Why does legal have such a bad reputation? I mean, that is part of the reason why I'm so passionate about contracting and why I moved to a legal tech company that's focused on contracting. It's because it's contracts. That's why, you know, legal gets a bad reputation. Because every time you try to get something done as a business, whether it's buying something, selling something, hiring somebody, you get stuck. You get stuck with Legal. You got to deal with legal. Right. And this is, this, that's a term that people use. They got to deal with this department. And I don't think that's fair. Right. And if we can fix that, if we can make that process smoother and accelerate it and make it actually a pleasant experience for the rest of the company, then legal can get out of having this bad reputation. And then the other thing I wanted to kind of react to was yeah, I do think there's a training, there is a mindset that is entrenched in the way that lawyers are taught in law school. It's reinforced in a law firm that when it comes to an in house environment, it is exactly as you're saying. You know, it's, it's rigid. It is. I got to get every single detail. But the business doesn't work that way. It's much more agile. It needs to move very, very quickly. Right. And so as a lawyer, I think moving from the law firm world into the in house world is a bit of a shock because you don't have the luxury of time and to go through every single detail, you've just got to make decisions based on whatever you've got in front of you by the time you've got to make that decision.

Mm. I think that's so right. And it's if to tie it back to, like, how I've built my career, people still ask me, lawyers still ask me, they say, do you have formal comedy training? What classes did you take? Thinking that, you know, thinking that all the things that I've done were based off of some formal education based on things that were done in the past. And having someone teach it to me, like that is a belief. That is a culture. And, you know, there's some things in the world that work like that, but many things, especially if you're at a scaling company, whether you're in sales and marketing and you need to figure out ways to stand apart from the competition, or if you're in legal and you're trying to figure out how to align yourself with top company priorities, you got to kind of feel out the situation sometimes and leap before you look. And I feel like sometimes there is that tension for lawyers knowing that that's what they should do. But it's hard to do that when you've been trained to approach problems very differently.

Yeah, very true. I remember when I was recently talking to some folks at a law school and they said they would give someone, like, an assignment, and if they turned over, like, 90% of every. I don't know, case. I'm not a lawyer. Right. Whatever, all the details. And they would get 90% of what would happen, and that is their final advice. They would get a B. But if you spent like an extra hundred hours and found that, like, one piece of detail to throw into your argument, then you would get an A plus. But in the real world, like, should we be recognizing that as good behavior? Isn't the 90% what you want when you are actually in real life and business and moving quickly versus no. I want you to scour the earth and get that one nugget that could be the 0.0001% of what goes wrong.

Yeah, it's. It's totally artificial. It's like a. You're living in an artificial environment. That's not how the world works. And I'll tell you, tied into how I've created my content, it evolved over time. My first draft tiktoks, my first things I put out, I remember I made a TikTok, not a TikTok. I made a zoom video and making a joke about how working at a legal department was like a lifestyle job that was based on what law firms told me. And then I Saw the reaction from the in house community saying, hey, this job is actually not a lifestyle job. It's demanding, there's a lot happening. And so I think that had I worried about putting out a perfect video, I wouldn't have gotten that feedback. And I've since then incorporated that feedback into future videos to like make jokes about how in house departments are perceived. But it came from being putting out an imperfect product and then iterating over time. And so it's, I don't, I think it's actually really a mistake to put out, to want to put out something perfect at the first go. Like perfectionism is a problem for so many reasons. And that's true in content creation but also in many other areas. So yeah, I don't know why there is this belief that you have to be perfect, but I think it holds a lot of lawyers and legal departments back.

Yeah, I agree. It's so funny. I consider myself the opposite of a perfectionist. I do everything as my mom would tell you. She says everything I do is mama hoo hoo, which in Chinese means like just, just barely getting by, like okay. And I'm like, yeah mom, that's why I'm good at my job. Like just do whatever needs to get done and then you move on. But it's like good enough.

Yeah, that's same here, same here. I'm the same way. So who knows? That's maybe why we're a culture fit for, for a new emerging field like community and, and in tech it's just, it's different.

Absolutely. Where do you get your ideas, Alex? Like you, you are very good at being fast to coming up with new, new humor and new, I don't know, pop culture. Things that are, that are happening and you jump on it pretty quickly and then relate it to legal where, where you get most of your ideas.

Well, part of it is that I, I put out a lot of content. Like only the best of the best videos that I make. The TikToks that I make end up on LinkedIn. I put out a lot of content on TikTok. I follow not that 90% rule. I probably follow a 50% rule where I, I'm actually ashamed of some of the things I put out. But occasionally I'm wrong and people love it. And so then the idea.

And you still put it out. You still put it out.

I still put it out, yeah. And it's because you can learn a lot just from the reactions. And this is why I think community is so important, not just for people who want to be influencers, but for companies, because that feedback loop is really the secret sauce. And I think that if you try to think of something perfect in a room, you'll never put anything out because you'll always think of a, a nuance or a mistake that you might make. So, so I put out a lot of stuff and a lot of it is from my own experience. A lot of it is also from being a salesperson who spoke to dozens of legal departments every week. And you know, they would tell me things like off the record and I would use those as ideas. But now it's also like, I'll put out ideas, I'll put out, put out videos and people will reach out to me and say, hey, I've got a good, a good idea. Even at clock, you know, I got so many people telling me ideas and, and you know, text messages saying, hey, remember, make a video on this because this is what we really hate. So I've got a lot of ideas. I got a loop now.

Is that good? Does that get annoying? I have ideas for you. Does that get annoying?

No, it never gets annoying because first of all, it means that people are paying attention. But also the things that I post about today will get boring someday and people will start copying it. And I think what I'm really doing is speaking to what people are really thinking. Like, I feel like the best TikTok ideas are ones where everyone in the audience knows this is true, but no one talks about it. So for example, the tension between legal and sales, like many outsiders don't know about that, but everybody who's worked in the legal department supporting a sales team, they get it. They know. Right? So that's going to eventually make its way out there. And so I think that there are other things on the cutting edge that people are thinking about and so I want to find out what those are. So I got to keep talking to people.

Do you know which is the one that's gotten the most hits, likes, or which has been your most successful and most popular video so far?

The most popular one was one of my earliest ones. I've come close, but I haven't actually surpassed it. It's a video I made that got over 2 million views on TikTok and I don't know how many million views elsewhere. It's a video of a young first year associate disrespecting a paralegal. The soundtrack is blinding lights by the weekend, it shows a first year disrespecting a paralegal and then everyone else Is like, oh, like they all realize, like, this is a mistake. Partner, a client, a judge. The theme behind it is really paralegals are really putting in a lot of work and don't get the respect that they deserve. And so I feel like that theme has been weaved into some of my videos. And then I think after that, there's a cluster of videos about the challenges of working at a legal department, especially between the tension between sales and legal. And I had this, like, character I play and I put up. I put on a backwards hat to pretend that I'm a sales guy. It's funny because I call him hat guy. But there are other names for this character that have existed way before I started making tiktoks. Like the annoying sales guy or Sales Gary is when I've heard a lot of. And so that cluster of themes around sales and legal, that's been probably one of my most popular themes.

Yeah, I love it. I love your videos. They're great. I can't get enough of them. Well, Alex, I want to thank you so much for being here today. I have a final question for you, which I like to ask everyone. And that is, do you consider yourself more of a rule follower or a rule breaker? And why?

I think I'm a rule breaker. I was a rule follower when I was younger and it wasn't for me. So now I just break rules. Occasionally, I will ask for forgiveness before permission. I have found that not all environments appreciate that. I mean, maybe you don't want your criminal defense lawyer to go off and not follow the rules, but in the tech world, I've found success with it by moving fast. And I feel like rules are always changing, so you got to kind of roll with it. So definitely, definitely feel more closely with not a rule follower.

Awesome. Hey, it was wonderful to have you here. We'll definitely want to have you back in the future. Thanks so much for your time, Alex, and thanks for being here on Pearls on Gloves Off.

I love it. Mary, thank you so much for having me. This was so much fun.

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