Creating Conversations on TikTok with Alex Su

Episode Summary

Today Corey chats with Alex Su, Head of Community Development at Ironclad. Alex explains his company, Ironclad, a a digital contracting technology that helps accelerate business contracts. Corey and Alex talk about Alex’s experience getting into TikTok and creating content and how that ultimately led to his job at Ironclad. Corey asks Alex about his unique position in a job that blends the traditionally at-odds fields of sales and legal. Alex discusses what it takes for a person to be a great salesperson, including having the right personality and also the right learning. Alex talks about how he doesn’t prescribe solutions but instead believes in creating conversations, as with his TikTok content. Corey and Alex talk about their shared affinity for shit-posting and its effectiveness, and discuss the way creating content is related to actual sales.

Episode Show Notes & Transcript

About Alex

Alex Su is a lawyer who's currently the Head of Community Development at Ironclad, the #1 contract lifecycle management technology company that's backed by Accel, Sequoia, Y Combinator, and other leading investors. Prior to joining Ironclad, Alex sold cloud software to legal departments and law firms on behalf of early stage startups. Alex maintains an active presence on social media, with over 180,000 followers across Twitter, LinkedIn, Instagram, and TikTok. 

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.

Corey: This episode is sponsored in part by Honeycomb. When production is running slow, it’s hard to know where problems originate. Is it your application code, users, or the underlying systems? I’ve got five bucks on DNS, personally. Why scroll through endless dashboards while dealing with alert floods, going from tool to tool to tool that you employ, guessing at which puzzle pieces matter? Context switching and tool sprawl are slowly killing both your team and your business. You should care more about one of those than the other; which one is up to you. Drop the separate pillars and enter a world of getting one unified understanding of the one thing driving your business: production. With Honeycomb, you guess less and know more. Try it for free at Observability: it’s more than just hipster monitoring.

Corey: I come bearing ill tidings. Developers are responsible for more than ever these days. Not just the code that they write, but also the containers and the cloud infrastructure that their apps run on. Because serverless means it’s still somebody’s problem. And a big part of that responsibility is app security from code to cloud. And that’s where our friend Snyk comes in. Snyk is a frictionless security platform that meets developers where they are - Finding and fixing vulnerabilities right from the CLI, IDEs, Repos, and Pipelines. Snyk integrates seamlessly with AWS offerings like code pipeline, EKS, ECR, and more! As well as things you’re actually likely to be using. Deploy on AWS, secure with Snyk. Learn more at That’s

Corey: Welcome to Screaming in the Cloud. I’m Corey Quinn. I’ve been off the beaten path from the traditional people building things in cloud by the sweat of their brow and the snark on their Twitters. I’m joined today by Alex Su, who’s the Head of Community Development at Ironclad, and also relatively well-renowned on the TikToks, as the kids say. Alex, thank you for joining me.

Alex: Thank you so much for having me on the show.

Corey: It’s always been an interesting experience because I joined TikTok about six months or so ago, due to an escalatingly poor series of life choices that continue to fail me, and I have never felt older in my life. But your videos consistently tend to show up there. You are @legaltechbro, which sounds like wow, I hate all of those things, and yet your content is on fire.

How long have you been doing the public dance thing, for lack of a better term? I don’t even know what they call it. I know how to talk about Twitter. I know how to talk about LinkedIn—sad. LinkedIn is sad—but TikTok is still something I’m trying to wrap my ancient brain around.

Alex: Yeah, I felt out of place when I first made my first TikTok. And by the way, I’m known for making funny skits. I have actually never danced. I’ve always wanted to, but I don’t think I have that… that talent. I started posting TikToks in, I will call it—let’s call it the fall of 2020. So, after the pandemic.

Before that, I had been posting consistently on LinkedIn for, gosh, ever since 2016, when I got into legal tech. And during the pandemic, I tried a bunch of different things including making funny skits. I’d seen something somewhere online if somebody’s making fun of the doctor life. And so, I thought, hey, I could do that for legal too. And so, I made one with iMovie. You know, I recorded it on Zoom.

And then people started telling me, “Hey, you should get on this thing called TikTok.” And so, I resisted it for a while because I was like, “This is not for me.” But at some point, I said, “I’ll try this out. The editing seems pretty easy.” So, I made a couple of videos poking fun at the life of a law firm lawyer or a lawyer working for a corporate legal department.

And on my fourth video, I went massively viral. Like, unexpected went viral, like, millions of—I think two million or so views. And I found myself with a following. So, I thought, “Hey, I guess this is what I’m doing now.” And so, it’s been, I don’t know, a year-and-a-half since then, and I’ve been continuously posting these skits.

Corey: It’s like they say the worst thing can happen when you go into a casino and play for the first time is you win.

Alex: [laugh].

Corey: You get that dopamine hit, and suddenly, well now, guess what you’re doing for the rest of your life? There you go. It sounds like it worked out for you in a lot of fun ways. Your skits about big law of life definitely track. My wife used to work in that space, and we didn’t meet till she was leaving that job because who has time to date in those environments?

But I distinctly remember one of our early dates, we went out to meet a bunch of her soon-to-be-former coworkers at something like eight or nine o’clock in Los Angeles on a Friday night. And at the end of it, we went back to one of our places, and they went back to work. Because that is the lifestyle, apparently, of being in big law. I don’t have the baseline prerequisites to get into law school, to let alone get the JD and then go to work in big law, and looking at that lifestyle, it’s, “Yeah, you know, I don’t think that’s for me.” Of course, I say that, and then three days later, I was doing a middle of the night wake up because the pager went off.

Like, “Oh, are you a doctor?” And the pager is like, “Holy shit. This SSL certificate expires in 30 days.” It’s, yeah. Again, life has been fun, but it’s always been one of those things that was sort of, I guess, held in awe. And you’re putting a very human face on it.

Alex: Yeah. You know, I never expected to be in big law either, Corey. Like, I was never good at school, but as I got older, I found a way to talk my way into, like, a good school. I hustled my way into a job at a firm that I never imagined I could get a job at. But once I got in, that’s when I was like, “Okay, I don’t feel like I fit in.”

And so, I struggled but I still you know grinded it out. I stayed at the job for a couple of years. And I left because I was like, “This is not right for me.” But I never imagined that all of those experiences in big law ended up being the source material for my content, like, eight years after I’d left. So, I’m very thankful that I had that experience even if it wasn’t a good fit for me. [laugh].

Corey: And on some level, it feels like, “Where do you get your material from?” It’s, “Oh, the terrible things that happened to me. Why do you ask?”

Alex: That’s basically it. And people ask me, they say, you know, “You haven’t worked in that environment for eight years. It’s probably different now, right?” Well, no. You know, the legal industry is not like the tech industry. Like, things move very slowly there.

The jokes that made people laugh back then, you know, 10 years ago, even 20 years ago, people still laugh at today because it’s the same way things have always worked. So, again, I’m very thankful that that’s been the case. And, you know, I feel like, the reason why my content is popular is because a lot of people can resonate with it. Things that a lot of people don’t really talk about publicly, about the lifestyle, the culture, how things work in a large firm, but I make jokes about it, so people feel comfortable laughing about it, or commenting and sharing.

Corey: I want to get into that a little bit because when you start seeing someone pop up again and again and again on TikTok, you’re one of those, “Okay, I should stalk this person and figure out what the hell their story is.” And I didn’t have to look very far in your case because you’re very transparent about it. You’re the head of community development at a company called Ironclad, and that one threw me for a little bit of a loop. So, let’s start with the easy question, I suppose. What is Ironclad?

Alex: We’re a digital contracting technology that helps accelerate business contracts. Companies deal with contracts of all types; a lot of times it gets bogged down in legal review. We just help with that process to make that process move faster. And I never expected I’d be in this space. You know, I always thought I was going to be a trial lawyer.

But I left that world, you know, maybe six years ago to go into the legal technology space, and I quickly saw that contracts was kind of a growing challenge, contracting, whether it’s for sales or for procurement. So, I found myself as a salesperson in legal tech selling, first e-discovery software, and then contracting software. And then I found my way to Ironclad as part of the community team, really to talk about how we can help, but also speaking up about the challenges of the legal profession, of working at a law firm or at a legal department. So, I feel like it’s all been the culmination of all my experiences, both in law and technology.

Corey: In the world in which I’ve worked, half of my consulting work has been helping our clients negotiate their large-scale AWS contracts and the other half is architectural nonsense of, “Hey, if you make these small changes, that cuts your bill in half. Maybe consider doing them.” But something that I’ve learned that is almost an industry-wide and universal truism, is that you want to keep the salespeople and the lawyers relatively separate just due to the absolute polar opposites of incentives. Salespeople are incentivized to sell anything that holds still long enough or they can outrun, whereas lawyers are incentivized to protect the company from risk. No, is the easy answer and everything else is risk that has to be managed. You are one of those very rare folks who has operated successfully and well by blending the two. How the hell did that happen?

Alex: I’m not sure to this day how it happened. But I think part of the reason why I left law in the first place was because I don’t think I fit in. I think there’s a lot of good about having a law degree and being part of the legal profession, but I just wanted to be around people, I wanted to work with people, I didn’t want to always worry about things. And so, that led me to technology sales, which took me to the other extreme. And so, you know, I carried a sales quota for five years and that was such an interesting experience to see where—to both sell technology, but also to see where legal fit into that process.

And so, I think by having the legal training, but also having been part of a sales team, that’s given me appreciation for what both teams do. And I think they’re often at tension with one another, but they’re both there to serve the greater goals of the company, whether it’s to generate revenue or protect against risk.

Corey: I think that there’s also a certain affinity that you may have—I’m just spitballing wildly—one of the things that sales folks and attorneys tend to have in common is that in the public imagination, as those roles are not, shall we call it, universally beloved. There tend to be a fair number of well, jokes, in which case, both sides of that tend to be on the receiving end. I mean, at some level, all you have to do is become an IRS auditor and you’ve got the holy trifecta working for you.

Alex: [laugh]. I don’t know why I gravitated to these professions, but I do think that it’s partly because both of these roles hold a significant amount of power. And if you look at just contracting in general, a salesperson at a company, they’re really the driver of the sales process. Like, if there’s no sale to be made, there’s no contract. On the flip side, the law person, the lawyer, knows everything about what’s inside of the contract.

They understand the legal terms, the jargon, and so they hold an immense amount of power over advising people on what’s going to happen. And so, I think sometimes, salespeople and legal people take it too far and either spend too much time reviewing a contract and lording it over the business folks, or maybe the salesperson is too blase about getting a deal done and maybe bypasses legal and doesn’t go through the right processes. By the way, Corey, these are jokes that I make in my TikToks all the time and they always go viral because it’s so relatable to people. But yeah, that’s probably why people always make jokes about lawyers and salespeople. There’s probably some element of ridiculing people with a significant amount of power within a company to determine these transactions.

Corey: Do you find that you have a better affinity for the folks doing contract work on the seller side or the buyer side? Something they don’t tell you when you run companies is, yeah, you’re going to spend a lot of time working on contracts, not just when selling things, but also when buying things and going back and forth. Aspects of what you’re talking about so far in this conversation have resonated, I guess, with both sides of that for me. What do you have the affinity for?

Alex: I think on the sales side, just because of my experience, you know, I think when you go through a transaction and you’re trying to convince someone to doing something, and this is probably why I wanted to go to law school in the first place. Like I watched those movies, right? I watched A Few Good Men and I thought I’d be standing up in court convincing a jury of something. Little did I know that that sort of interest [crosstalk 00:10:55]—

Corey: Like, Perry Mason breakthrough moment.

Alex: That moment where—the gotcha moment, right? I found that in sales. And so, it was really a thrill to be able to, like, talk to someone, listen to them, and then kind of convince them that, based on what challenges they’re facing, for them to buy some technology. I love that. And I think that was again, tied to why I went to law school in the first place.

I didn’t even know sales was a possible profession because I grew up in an immigrant community that was like, you just go to school, and that’ll lead to your career. But there’s a lot of different careers that are super interesting that don’t require formal schooling, or at least the seven years of schooling you need for law. So, I always identify with the sales side. And maybe that’s just how I am, but obviously, the folks who deal with the buy side, it’s a pretty important job, too.

Corey: There’s a lot of surprise when I start talking to folks in the engineering world. First, they’re in for a rough awakening at times when they learn exactly how much qualified enterprise salespeople can make. But also because being a lawyer without, you know, the appropriate credentials to tie into that, you’re going to have a bad time. There are regulatory requirements imposed on lawyers, whereas to be a salesperson, forget the law degree, forget the bachelor’s, forget the high school diploma, all you really need to be able to do from an academic credential standpoint is show up.

The rest of it is, can you actually sell? Can you have the conversations that convince people to see the outcome that benefits everyone? And I don’t know what that it’s possible, or advised necessarily, to be able to find a way to teach that in some formalized way. It almost feels like folks either have that spark or they don’t. Do you think it’s one of those things that can be taught? Do you think it’s something that people have to have a pre-existing affinity for?

Alex: It’s both, right, because part of it is some people will just—they don’t have the personality to really sell. It’s also like their interest; they don’t want to do that. But what I found that’s interesting is that what I thought would make a good salesperson didn’t end up being true when I looked at the most effective sellers. Like, in my head, I thought, “Oh, this is somebody who’s very boisterous, very extroverted,” but I found that in my experience in B2B SaaS that the most effective sellers are very, very much active listeners. They’re not the people showing up and talking at you. They are asking you about your day-to-day asking about processes, understanding the context of your situation, before making a small suggestion about what you might want to do.

I was very impressed the first time I saw one of these enterprise sellers who was just so good at that. Like, I saw him, and he looked nothing like what I imagined an effective sales guy to look like. And he was really kind and he just, kind of, just talked to me, like, I was a human being, and listened to my answers. So, I do think that there is some element of nature, your talent when it comes to that, but it can also be trained because I think a lot of folks who have sales talent, they don’t realize that they could be good at it. They think that they’ve got to be this extroverted, happy hour, partying, storyteller, where —

Corey: The Type A personality that interrupts people as they’re having the conversation.

Alex: Yeah, yeah.

Corey: Yeah.

Alex: So anyways, I think that’s why it’s a mix of both.

Corey: The conversations that I’ve learned the most from when I’m talking to prospects and clients have been when I asked the quote-unquote, dumb question that I already know the answer to, and then I shut up and I listen. And wow, I did not expect that answer. And when you dig a little further, you realize there’s nuance that—at least in my case—that I’ve completely missed to the entire problem space. I think that is really one of the key differentiators to my mind, that separate people who are good at this role from folks who just misunderstand what the role is based upon mass media, or in other cases—same problem with lawyers—the worst examples, in some cases, of the profession. The pushy used car salesperson or the lawyer they see advertising on the back of a bus for personal injury cases. The world is far more nuanced than that.

Alex: Absolutely. And I think you hit the nail on the head when you said, you know, you ask those questions and let them talk. Because that’s an entire process within the sales process. It’s called discovery, and you’re really asking questions to understand the person’s situation. More broadly, though, I think pitching at people doesn’t seem to work as well as understanding the situation.

And you know, I’ve kind of done that with my content, my TikToks because, you know, if you look at LinkedIn, a lot of people in our space, they’re always prescribing solutions, giving advice, posting content about teaching people things. I don’t do that. As a marketer, what I do is I talk about the problems and create discussions. So, I’ll create a funny video—

Corey: I think you’re teaching a whole generation that maybe law school isn’t what they want to be doing, after all there is that.

Alex: There is that. There is that. It’s a mix of things. But one of the things I think I focus on is talking about the challenges of working with a sales team if you’re an in-house lawyer. And I don’t prescribe technology, I don’t prescribe Ironclad, I don’t say this is what you need to do, but by having people talk about it, they realize, right—and I think this is why the videos are popular—as opposed to me coming out and saying, “I think you need technology because of XYZ.” I think, like, facilitating the conversation of the problem space, that leads people to naturally say, “Hey, I might need something. What do you guys do, by the way?”

Corey: This episode is sponsored in part by our friend EnterpriseDB. EnterpriseDB has been powering enterprise applications with PostgreSQL for 15 years. And now EnterpriseDB has you covered wherever you deploy PostgreSQL on-premises, private cloud, and they just announced a fully-managed service on AWS and Azure called BigAnimal, all one word. Don’t leave managing your database to your cloud vendor because they’re too busy launching another half-dozen managed databases to focus on any one of them that they didn’t build themselves. Instead, work with the experts over at EnterpriseDB. They can save you time and money, they can even help you migrate legacy applications—including Oracle—to the cloud. To learn more, try BigAnimal for free. Go to, and tell them Corey sent you.

Corey: It sounds ridiculous for me to say that, “Oh, here’s my entire business strategy: step one, I shitpost on the internet about cloud computing; step two, magic happens here; and step three people reach out to talk about their AWS bills.” But it’s also true. Is that the pattern that you go through: step one, shitpost on TikTok; step two, magic happens here; and step three people reach out asking to learn more about what your company does? Or is there more nuance to do it?

Alex: I’m still figuring out this whole thing myself, but I will say shitposting is incredibly effective. Because I’m active on Twitter. Twitter is where I start my shitposts. TikTok, I also shitpost, but in video format, I think the number one thing to do is figure out what resonates with people, whether it’s the whole contracting thing or if it’s frustrations about law school. Once you create something that’s compelling, the conversation gets going and you start learning about what people are thinking.

And I think that what I’m trying to figure out is how that can lead to a deeper conversation that can lead to a business transaction or lead to a sale. I haven’t figured it out, right, but I didn’t know that when I started creating content that spoke to people when I was a quota-carrying salesperson, people reached out to me for demo requests, for sales conversations. There is something that is happening in this quote-unquote, “Dark funnel,” that I’m sure you’re very familiar with. There’s something that’s happening that I’m trying to understand, and I’m starting to see.

Corey: This is probably a good thing to the zero in on a bit because to most people’s understanding of the sales process, it would seem that you going out and making something of a sensation out of yourself on the internet, well what are you doing that for? That’s not sales work? How is that sales? That’s just basically getting distracted and going to do something fun. Shouldn’t you be picking up the phone and cold calling people or mass-emailing folks who don’t want to hear from you because you trick them into having a badge scanned somewhere? I don’t necessarily think that is accurate. How do you see the interplay of what you do and sales?

Alex: When you’re selling something like makeup or clothing, it’s a pretty transactional process. You create a video; people will buy, right? That’s B2C. In B2B, it’s a much more complex processes. There’s so many touchpoints. The start of a sales conversation and when they actually buy may take six months, 12 months, years. And so, there’s got to be a lot of touch points in between.

I remember when I was starting out in my content journey, I had this veteran enterprise sales leader, like, your classic, like, CRO. He said to me, “Hey, Alex, your content’s very funny, but shouldn’t you be making cold calls and emails? Like, why are you spending your time doing this?” And I said, “Hey, listen, do you notice that I’m actually sourcing more outbound sales calls than any other sales rep? Like, have you noticed that?”

And he’s like, “Actually, yeah, I did notice that. You know, how are you doing it?” And I was like, “Do you not see that these two are tied? These are not people I just started calling. They are people who have seen my content over time. And this is how it works.”

And so, I think that the B2B world is starting to wise up to this. I think, for example, Ironclad is leading the way on creating a community team to create those conversations, but plenty of B2B companies are doing the same thing. And so, I think by inserting themselves in a conversation—a two-way conversation—during that process, that’s become incredibly effective, far more so than, like, cold-calling a lawyer or a developer who doesn’t want to be bothered by some pushy salesperson.

Corey: Busy, expensive professionals generally don’t want to spend all their time doing that. The cold outreach emails that drive me nuts are, “Hey, can we talk for half an hour?” Yeah, I don’t tend to think in terms of billable hours because that’s not how I do anything that I do, but there is an internal rate that I used to benchmark and it’s what you want me just reach into my pocket and give you how much money for a random opportunity to pitch me on something that you haven’t even qualified whether I need or not? It’s like, asking people for time is worse, in some ways, than asking for money because they can always make more money, but no one can make more time.

Alex: Right, right. That’s absolutely right.

Corey: It’s the lack of awareness of understanding the needs and motivations of your target market. One thing that I found that really aided me back when I was working for other folks was trying to find a company or a management structure that understood and appreciated this. Easy example, when I was setting out as an independent consultant after a few months I’d been doing this and people started to hear about me. But you know, it turns out that there are challenges to running a business that are not recommended for most people. And I debated, do I take a job somewhere else?

So, I interviewed at a few places, and I was talking to one company that’s active in the cloud costing space at the time and they wanted me to come aboard. But discussions broke down because they thought I was, quote, “More interested in thought leadership than I was and actually fixing the bills themselves.” And looking at this now, four years later or so, yeah, they were right. And amazing how that whole thing played out, but that the lack of vision around, there’s an opportunity here, if we can chase it, at least in the places I was at, was relatively hard to come by. Did you luck out in finding a role that works for you in this way or did you basically have to forge it for yourself from the sweat of your brow and the strength of your TikTok account?

Alex: It was uphill at first, but eventually, I got lucky. And you know, part of it was engineered luck. And I’ll explain what I mean. When I first started out doing this, I didn’t expect this to lead to any jobs. I just thought it would support my sales career.

Over time, as the content got more popular, I never wanted to do anything else because I was like, I don’t want to be a marketer. I’m not a—I don’t know anything about demand gen. All I know is how to make funny videos that get people talking. The interesting that happened was that these videos created this awareness, this energy in our space, in the legal space. And it wasn’t long before Ironclad found me.

And you know, Ironclad has always been big on community, has always done things like—like, our CEO, our founder, he said that he used to host these dinners, never talking about Ironclad, but just kind of talking about law school and law with potential clients. And it would lead to business. Like, it’s almost the same concept of, like, not pushing sales on people. And so, Ironclad has always had that in its DNA. And one of our investors, our board members, Jessica Lee from Sequoia, she is a huge believer in community.

I mean, she was the CEO of another company that leveraged community, and so there’s this community element all throughout the DNA of Ironclad. Now, had I not put myself out there with this content, I may not have been discovered by Ironclad. But they saw me, they found me, and they said, “We don’t think about these things like many other companies. We really want to invest in this function.” And so, it’s almost like when you put yourself out there, yes, sometimes some people will say, “What are you doing? Like, this makes no sense. Like, stop doing that.” But there’s going to be some true believers who come out and seek you out and find you.

And that’s been my experience here, like, at Ironclad. Like, people were like, “When you go there, are they going to censor you? Is your content going to be less edgy?” No. Like, they pulled me aside multiple times and said, “Keep being yourself. This is what we want.” And I think that is so special and unique. And part of it is very much lucky, but it’s also when you put yourself out there kind of in a big way, like-minded people will seek you out as well.

Corey: I take the position that part of marketing, part of the core of marketing, is you’ve got to have an opinion. But as soon as you have an opinion, people are going to disagree with you. They’re going to, effectively, forget the human on the other side of it and start taking you for a drag on social media and whatnot. So, the default reaction a lot of people have is oh, I shouldn’t venture opinions forward.

No. People are always going to dislike you for something and you may as well have it be for who you are and what you want to be doing rather than who you’re pretending to be. That’s always been my approach. For me, the failure mode was not someone on Twitter is going to get mad about what I wrote. No one’s going to read it. That’s the failure mode. And the way to avoid that is make it interesting.

Alex: That is a hundred percent relatable to me because I think when I was younger, I was scared. I did worry that I would get in trouble for what I posted. But I realized these people I was worried about, they weren’t going to help me anyways. These are not people who are going to seek me out and help me but then say, “Oh, I saw your content, so now I can’t help you.” They were not going to help me anyways.

But by being authentic to myself and putting things out there, I attracted my own tribe of people who have helped me, right? A lot of my early results from content came not because I reached my target customers; it was because somebody resonated with what I put out there and they carried my message and said, “Hey, you should talk to Alex.” Something special happens when you kind of put yourself out there and say an opinion or share a perspective that not everyone agrees with because that tribe you build ends up helping you a lot. And meanwhile, these other people that might not like it, they probably weren’t going to help you either.

Corey: I maintain that one of the most valuable commodities in the universe is attention. And so, often there’s so much information overload that’s competing for our attention every minute of every day that trying to blend in with the rest of it feels like the exact wrong approach. I’m not a large company here. I don’t have a full marketing department to wind up doing ad buys, and complicated campaigns, and train a team of attacking interns to wind up tackling people to scan their badges at conferences. I’ve got to work with what I’ve got.

So, the goal I’ve always had is trigger the Rolodex moment where someone hears about a problem in the AWS billing space—ideally—and, “Oh, my God, you need to talk to Corey about that.” And it worked, for better or worse. And a lot of it was getting lucky, let’s be very clear here, and people doing me favors that they had no reason to do and I’ll never be able to repay. But being able to be in that space really is what made the difference. Now, the downside, of course, when you start doing that is, how do you go back to what happened before?

If you decide okay, well, it’s been a fun run for you and Ironclad. And yeah, TikTok. Turns out that is, in fact, for kids; time to go somewhere else. Like, I don’t know that you would fit into your old type of job.

Alex: Yeah. No, I wouldn’t. But very early on, I realized, I said, “If I’m going to find meaningful work, it’s okay to be wrong.” And when I went to big law, I realized this is not right for me. That’s okay. I’m just not going to get another big law job.

And so, when people ask me, “Hey, now that you’ve put yourself out there, you probably can’t get a job at a big firm anymore.” And that’s okay to me because I wasn’t going to go back anyways. But what I have found, Corey, is that there’s this other universe of people, whether it’s a entrepreneur, smaller businesses, technology companies, they would be interested in working with me. And so, by being myself, I may have blocked out a certain level of opportunities or a safety net, but now I’m kind of in this other world where I feel very confident that I won’t have trouble finding a job. So, I feel very lucky to have that, but that’s why I also don’t worry about the possibility of not going back.

Corey: Yeah, I’ve never had to think about the idea of, well, what if I go have to get a job again? Because at that point, it means well, it’s time to let every one at the company who is depending on the go, and that’s the bigger obstacle because, let’s be honest, I’m a white guy in tech, and I look like it. My failure mode is basically a board seat and a book deal because of inherent bias in the system.

Alex: [laugh]. Oh, my god.

Corey: That’s the outcome that, for me personally, I will be just fine. It’s the other people took a chance on me. I’m terrified of letting them down. So far, knock on wood, I haven’t said anything too offensive in public is going to wind up there. That’s also not generally my style.

But it is the… it is something that has weighed on me that has kept me from I guess, thinking about what would my next job be? I’m convinced this is the last job I’ll ever have, if for no other reason that I’ve made myself utterly unemployable.

Alex: [laugh]. Well, I think many of us aspire to find that perfect intersection of what you love doing and what pays the bills. Sounds like you’ve found it, I really do feel like I found it, too. I never imagined I’d be doing what I do now. Which is also sometimes hard to describe.

I’m not making TikToks for a living; I’m just on the community team, doing events—I’m getting to work with people. I’m basically doing the things that I wanted to do that led me to quit that job many years ago, that big law job many years ago. So, I feel very blessed and for anybody who’s, like, looking for that type of path, I do think that at some point, you do need to kind of shed the safety nets because if you always hang on to the safety nets, whether it’s a big tech job or a big law job, there’s going to be elements of that that don’t fit in with your personality, and you’re never going to be able to find that if you kind of stay there. But if you venture out—and, you know, I admire you for what you’ve done; it sounds like you’re very successful at what you do and get to do what you love every day—I think great things can happen.

Corey: Yeah, I get to insult Amazon for a living. It’s what I love. It’s what I would do if I weren’t being paid. So, here we are. Yeah—

Alex: [laugh].

Corey: I have no sense of self-preservation. It’s kind of awesome.

Alex: I love it.

Corey: But you’re right. It’s… there’s something to be said for finding the thing that winds up resonating with you and what you want to be doing.

Alex: It really does. And you know, I think when I first made the move to technology, to sales, there was no career path. I thought I would—maybe I thought I might be a VP of Sales. But the thing is, when you put yourself out there, the opportunities that show up might not be the ones that you had always seen from the beginning. Like if you ask a lawyer, like, “What can I do if I don’t practice law?” They’re going to give you these generic answers. “Work here. Work there. Work for that company. I’ve seen a lot of people do this.”

But once you put yourself out there in the wilderness, these opportunities arise. And I’ve been very lucky. I mean, I never imagined I’d be a TikTokker. And by the way, I also make memes on Twitter. Couldn’t imagine I’d be doing that either. I learned, like, Mematic, these tools. Like, you know, like, I’m immersed in this internet culture now.

Corey: It is bizarre to me and I never saw it coming either. For better or worse, though, here we are, stuck at it.

Alex: [laugh].

Corey: I really want to thank you for taking so much time to speak with me today. If people want to learn more about what you’re up to and follow along for the laughs, if nothing else, where’s the best place for them to find you?

Alex: The best way to find me is on LinkedIn; just look up Alex Su. But I’m around and on lots of social media platforms. You can find me on Twitter, on Instagram, and on TikTok, although I might be a little bit embarrassed of what I put on TikTok. I put some crazy gnarly stuff out there. But yeah, LinkedIn is probably the best place to find me.

Corey: And we will put links to all of it in the show notes, and let people wind up making their own decisions. Thanks so much for your time, Alex. I really appreciate it.

Alex: Corey, thank you so much for having me. This was so much fun.

Corey: Alex Su, Head of Community Development at Ironclad. 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 insipid comment talking about how unprofessional everything we talked about is that you will not be able to post for the next six months because it’ll be hung up in legal review.

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.
Newsletter Footer

Get the Newsletter

Reach over 30,000 discerning engineers, managers, enthusiasts who actually care about the state of Amazon’s cloud ecosystems.

"*" indicates required fields

This field is for validation purposes and should be left unchanged.
Sponsor Icon Footer

Sponsor an Episode

Get your message in front of people who care enough to keep current about the cloud phenomenon and its business impacts.