June 27, 2022

Solving Specific, Expensive AWS Problems with Corey Quinn

by To Comply or Not To Comply

Show Notes

I invite Corey Quinn to take a break from his podcast hosting role and join me on the opposite side of the table on To Comply or Not to Comply this week. As the Cloud Economist at the Duckbill Group, writer of the Last Week in AWS newsletter, and host of the podcast Screaming in the Cloud, Corey is an expert in Amazon Web Services (AWS). Corey joins me in this episode to talk about developing his business focus, being profiled by the New York Times, and making the decision to invest in my startup, ByteChek.


Timecoded Guide:

[04:23] Finding a business niche and understanding the value of the Duckbill Group’s AWS expertise 

[11:56] Explaining where the humor of Last Week in AWS comes from and how Corey keeps a lighthearted yet snarky and amusing perspective on AWS issues 

[18:10] Delving into Corey’s vision for the investment portion of his career and what his motivations were for becoming an investor in ByteChek

[26:42] Being featured in the New York Times and explaining the reactions that both he and others had to the article about him

[29:34] Noticing the role that fatherhood has had in his career and how Corey has learned to better prioritize his schedule and his family 


How did you develop the focus on AWS for the Duckbill Group?

Although I point out the criticisms specialists in tech often receive, Corey is quick to defend the Duckbill Group’s focus on AWS. His reasoning? It pays well and it’s a very important problem to fix. It might seem like a source of strength to be a jack of all trades or a generalist, but Corey says that there’s rarely a market for generalists. Instead, people and companies alike approach specialists to solve their problems, wanting to pay the money for their expertise rather than take a chance on someone they only knows a general overview of their issue or problem.

“People don't want to reach out with expensive problems to generalists. They want to reach out to someone who they believe specializes in the exact problem they deal with and that they want to get solved.” 


What is the feedback like for your Last Week in AWS newsletter?

Corey’s Last Week in AWS newsletter has developed a really decent following over the span of his career, starting only as a fun way to share news and skyrocketing from there. Even with the increased popularity of his newsletter, Corey’s surprising news is that he actually rarely receives email feedback from subscribers. He receives positive feedback in-person, especially from peers enjoying his takes on the latest developments and finding humor in the snarky statements he makes, but Corey finds that email responses and feedback are hardly the norm for him, only receiving the occasional typo correction. 

“Increasingly, I find that when people have problems with what I write, the easiest way to fix that is to have a conversation with them and add a little context. Sometimes I'm wrong, sometimes I'm not, but it's always a conversation that leads to better outcomes as a result.”


What was that experience like, to be in the New York Times, talking just about who you are and what you bring to the space?

Although Corey has a following in the AWS space, it was a big surprise to him for the New York Times to reach out for a profile on him and it provided him with an incredible perspective of the impact of what he does not only with Duckbill Group, but with everything involved in Last Week in AWS. This was a source of stress for Corey, who definitely worried about what would come from such a high-profile publication covering his occasionally snarky work, but he’s been incredibly pleased with the response so far and hopes it continues to elevate his platform and spreads the words about the common issues of AWS

“Believe me, I deserve a lot of criticism for the things I say and do, but it was a really interesting experience, start to finish. I didn't expect it to get the level of attention that it did. I didn't expect the positive business outcomes that came out of it, and I'll be forever grateful.”


Why are you open to sharing your fatherhood journey with folks out there and how has being a father played a role in your career?

As a father myself, Corey’s dedication and care towards his two children inspires me to continue to share my journey through fatherhood out in the open. While motherhood has become an increasingly visible talking point as we discuss tech work environments, fatherhood can also have a massive impact on the decisions we choose in our careers. For Corey, he’s quick to admit that his fatherhood informs his decisions to unplug from his work on the weekend. He’s willing to set strict boundaries with himself about when he’s working and when he’s not, especially when it means he can be there for his children as they grow up.

“There's always going to be another RSA coming to town, or there's always going to be another event where I'm invited to keynote, but I'm not going to get these years of having young kids back. I want to spend time with them as they grow up.” 



Keep up with our guest, Corey Quinn, on LinkedIn, Twitter, the Last Week in AWS website, and the Duckbill Group website

Read the New York Times article about Corey Quinn and check out Corey’s podcast, Screaming in the Cloud

Connect with AJ Yawn on LinkedIn and Twitter

Follow ByteChek on LinkedIn and Twitter, or learn more about ByteChek on their website Listen to more from the Hacker Valley Studio and To Comply or Not to Comply


AJ 00:15
Alright, welcome to another episode of the To Comply or Not to Comply podcast. I'm your host AJ Yawn, founder and CEO of ByteChek, the only all-in-one cybersecurity compliance automation solution in the market. I'm joined here by a friend and one of the funniest people in tech, Corey Quinn, who is the Chief Cloud Economist at the Duckbill Group. He also runs Last Week in AWS, which is an AWS newsletter with over 31,000 subscribers, and probably least importantly, but most important to me, an investor in my startup, ByteChek, as well, which we want to make sure we are clear about here from the beginning. Corey, thank you for joining me.
Corey 00:55
No, thank you for having me. I'm always willing to indulge my ongoing love affair with the sound of my own voice.
AJ 01:02
Absolutely. Corey, this is the first time we flipped the tables here. I've been on your podcast and now, I'm on the other side and I'll tell you being on the interview side is a lot harder than being a guest, so I salute you for all the times that you interviewed me. And hopefully, we have a good time here with you on the other side of the table. Do you do this often, where you’re actually on the other side of the table?
Corey 01:22
I do from time to time, though certainly not nearly as frequently as I sit around on the Screaming in the Cloud podcast interviewing other folks. There's a lot that you have to worry about when you're a host, because you never know how a given guest is gonna go. Is someone going to be one of those people that starts rambling for 15 minutes, and you can't get a word in edgewise? Or, are they going to answer a complicated question with a single word response and you're scrambling to figure out how you're going to possibly fill up the rest of the airtime? It's way easier on this side of the table.
AJ 01:51
Right. Yes, I've experienced both of those, and I don't necessarily know if I figured out how to handle them just yet. Luckily, there's some great editors behind me that make the podcast sound great, but Corey, I know we know each other very well, but for the folks that are out there that are listening, that this is their first time hearing from you, which I would be very surprised of, give us a quick background of your history and what you're up to now.
Corey 02:13
Sure, the short version is that as an employee in the SRE/Engineering space, I was one of the best in the world at getting myself fired from jobs. Eventually, I wound up getting tired of that, I figured out, "I'll go hang out a shingle as an independent consultant. Let's find an expensive problem that I can solve relatively rapidly from a position of expertise." And the horrifying AWS Bill seemed like the thing to do. Fast forward and now, we're now an 11-person company and the only problem we solve is fixing the AWS Bill, either in terms of cost optimization, usually read as lowering it, or helping companies negotiate their large-scale contracts with AWS directly. And that's been fun, it's been obviously a very interesting place to hang out, but where people tend to know me better from is, what started off is that consulting efforts marketing direction, which is LastWeekInAWS.com. I gathered the news from Amazon's cloud ecosystem, sort out the things that I don't find personally interesting, take what's left, and every week, I wind up sending that out to a whole bunch of people, where I'm gently and lovingly making fun of it. And for whatever reason, this is not a common storytelling path that people like to go down, so I tend to stand alone in that respect. And it's really neat watching me throw stones at a $1.2-trillion company. As of this week, their stock price continues to be in decline, I'm a little worried that when they dropped below the four-comma mark, am I now going to be considered punching down? But that's a problem for future Corey and, you know, Amazon's stockholders,
AJ 03:46
Right, absolutely. And so, you went from engineering to now poking fun, or now helping customers solve some really challenging problems with our AWS bills. If anyone here has an AWS Bill, you know exactly the problem that Corey helped solve, because I'm confused right now just sitting here about my AWS bill. And talk to me about just that path, Corey, you mentioned getting fired a few times, but going from engineering to deciding to be very niche. And I know there's a saying, especially in my space, the riches are in the niches. Was this a decision based off of you thought, "I'm going to just be insanely focused," or how did you get to helping people with their cloud bills?
Corey 04:23
A common mistake when you're trying to go out and set up your own shingle as an independent consultant is you want to be as broad as possible, but the more you do that, "Oh, I'm great at computers," people don't want to reach out with expensive problems to generalists. They want to reach out to someone who they believe specializes in the exact problem they deal with and that they want to
get solved. And people often will ask me even now, "Oh, you're going to branch out into GCP and Azure?" No because we are subject matter experts on AWS. We'll make that shift if we start seeing industry-wide trends away from AWS being the market leader, but we can move a lot faster than the industry can on things like that. Being at the top of the mental SEO stack for a very specific, very expensive problem is one of those things that just pays an awful lot of dividends. It's counterintuitive. You think, I'll wind up doing architecture work as well, because cost and architecture and cloud are very much the same. Or, ooh, can you also handle advising on our cloud migration? And while we could, the honest answer is, is that we are way better at doing the same very specific, very challenging, but also very bounded problem and becoming effectively, the world experts on that one problem. Having something that resonates with people who are experiencing it and feeling that pain? It does more than any marketing campaign is going to be able to achieve, it's your best effort. It's basically triggering the Rolodex moment. You describe what you do, and someone pops up with, "Oh, I know someone you need to talk to." Because people don't go out and talk publicly, at least the big companies, about their painful AWS bill. So, I've got to be noisy enough that they can find me on their own.
AJ 05:59
Exactly, yep. And I think that's advice that I would give you know, anyone, whether you're starting a company, whether you're trying to break into the field, whether you're running a company and you think, for some reason, you need to do multi-cloud strategy. Focus is one of those things that you should really think about. You run an 11-person team, and you talked about, "We are all very, very good at AWS." And I can hear detractors out there, like, "Well, you're limiting those people to only learning AWS," and I tell people that are breaking into this field to focus on one cloud provider. I don't see a legit reason for people to consider themselves, quote, unquote, experts across multiple cloud providers, because I think that's frankly impossible with how fast these cloud providers are changing things. I just 100% agree with everything you're saying they're around focus, and it just being a superpower when you lock in on something. And like you said, people don't go to solve problems for the generalist. They want to know that, "If I'm spending five, six figures on a problem, that the person that I'm spending that money on actually knows how to solve that problem and have some proof points that they have."
Corey 06:58
Yeah, to be clear, we also bias for hiring senior people. It's challenging, in a small consultancy
operation, to bring someone into an engagement who is new to the space. Again, people don't hire junior people to solve very expensive, very difficult problems in an advisory sense. So, I hear what you're saying, and the detractors as well, "Oh, you should find some way to start uplifting folks who are new to the space, or you're holding your existing staff back." Well, the existing staff is here because they're already very good at the AWS bids when we find them. And as far as finding a way to bring new folks in, I agree with you. It's just a lot easier said than done.
AJ 07:37
Yep. And speaking of that, running the 11-person team, mainly senior folks, and we're in this kind of new, I don't know if it's a new era, but people care more about how they're treated at work, and they want to have work not be something that kills them and destroys their lives. They would actually like to live life outside of work. Talk to me about running a small business where you obviously know all of your employees, you know them well, you have to interact with them a lot, and that takes a certain level of leadership, but also hiring senior people, who come in with a lot of background, who come in with a lot of scars, who come in with a lot of experiences that you're trying to make sure fits what you're doing there at the Duckbill Group.
Corey 08:15
We make it a point here to ensure that this is not one of those jobs that you have to basically sacrifice your nights and weekends into. There's a reason that we focus around a very expensive, very painful problem that is also bounded to business hours People don't have a 2am billing emergency. If they think they do, it is far likelier that they're having a security incident and the bills can catch up to the rest of that later. We have had a couple of weird moments where we have simultaneous clients on opposite sides of the world. So, we have to run a little ragged for that and reinvent, especially on the media side of the company, it's always a rough, rough week for everyone. But by and large, we're trying to build more of a lifestyle company, where people don't have to wind up sacrificing themselves for the future of
what it is we're trying to build here. My business partner, Mike, and I view this as being the last job we'll ever have, and we're not so old that the remainder of our career is something you can take care of in a sprint. It's a marathon. So, how do we wind up doing this in a sustainable ongoing way? We treat people well, we don't play ridiculous games. Easy example for that, one, is we have a 401 K match that vests instantly, an it's one of those free money stories. We're not tight, like even Amazon themselves has a 50% match, we match to 100%, but okay, and you have to be there for three years or you don't get a penny of it. Yeah, in our case, it's instant vests. As soon as the pay period closes, that money is yours. We're not here trying to manipulate people's behavior. We ask everyone in the interview process: What is your job after this one and how do we help you get there? No one works here because they can't find somewhere else to work. They're here because we strive to offer them something that is very challenging to get somewhere else.
AJ 10:00
That's awesome. Where does that come from? Is that past experiences and you just want to build something that's different than what you grew up in? Or, is this just nature of growing Duckbill and realizing this is the way you would build a company?
Corey 10:13
I'm better and cynical. If I wanted to burn through people as in a sprint to an outcome, I would structure things radically differently, but I'm building with an eye toward the long term, where I don't need to hit arbitrarily close-in deadlines, or certain revenue percentages, or, again, no shade whatsoever intended on this, but we have no external investors. Our largest customer is a low single digit percentage of our revenue here and, as a result, that’s the freedom to mouth off to big companies, because I can't actually get fired. There's no external pressure or external impetus that's driving us to behave in ways to benefit the short term at the expense of the long. More cynically, I also believe that you can sell out exactly once in your career, so make it worth it. So, yeah, if someone winds up coming along and wanting me to pitch a multi-cloud strategy that I think is ridiculous, and I start doing it, yeah, you can expect me to announce my new VP role at IBM three weeks later, or something like that, because that's the one time I get the sell-out. But for some reason, people are not rushing to acquire us in that sense, and that's okay. I didn't build this to sell it. I built this because this is where I want to be.
AJ 11:17
I think Twitter would break if you showed up as a VP at IBM, I think the entire website would crash. It'd be very difficult to put Twitter back together after probably weeks of chaos.
Corey 11:31
It would be an interesting revelation, but it's maybe a fun April Fool's Day joke, but I'm not a big fan of
lying to people once a day. I made that mistake once, years ago, where I referenced that I was
marrying a friend of mine. Next tweet was to her husband, I still to this day, have people who think that she is my wife because people don't read the whole thing and it takes a while for people to catch back up on these things. So, yeah, I've learned my lesson about jokes like that.
AJ 11:56
I bet. So, Corey, you're obviously one of the funniest guys in the industry, one of the funniest people I know, and it comes out in Last Week in AWS, in your newsletter, and I think the reason why people respect it so much, at least in the industry is because you know what you're talking about. You actually know what you're saying. It's not just jokes for the sake of jokes, but talk to me about like, where did that come from? Did that personality just start in college? Were you a stand-up comedian at some point? How did this come out? Applying it to tech is an interesting way to take an approach of sharing news in what's going on in the largest cloud provider in the world.
Corey 12:31
I am deeply ADHD in a whole bunch of different ways, and that means I'm great at some things and terrible at others. It's right on the 10 that attention span is one of those things that I've always struggled with. For me, I have the tacit acknowledgement going into this, that I'm talking about what has changed in cloud computing services. Let's be very blunt for a second. That's incredibly boring. And to sit there and tell the "just the facts, ma'am" style of delivery, I don't have the patience to write it. So, I know that no one's going to have the patience to read it. My goal instead is: How do I tell a joke about a given release, that isn't the same tired old joke and doesn't go too far into the point where I now have to apologize to people for it? It keeps me on my toes and that's why, five years in, I'm still finding it
engaging and fun and I haven't gotten bored and wandered off for something else shiny. It's really, for me, that I write these things, and the fact that other people seem to like it, it's found a niche in which it resonates, I'll take it. I'm grateful to find that out. I expected it not to. I had metrics all set up for, "Great, at what point do I acknowledge that this effort has failed, and it's time for me to spend the energy on something more productive?" I wound up getting that and hitting that subscriber number before I launched and okay, here we are.
AJ 13:46
That's awesome. What is the feedback like? Do you sometimes get the "that was a little bit too far,” or “keep going” type of praise? I imagine the replies to the newsletter coming back are all over the place.
Corey 13:59
There are times that I could be forgiven for not thinking anyone actually reads what I write, because the most common response is nothing. You can hit reply to those newsletters and go straight to my inbox, and the reason that still works is that people very rarely do. And I think, "Is this thing on?" But then, I make a mistake or I typo something and oh, do I get emails coming in. And that reminds me that, yeah, I do, in fact, wind up having people reading this thing and it's great to see it. It's great to wind up seeing just how much of this stuff does resonate, but most of the feedback I've gotten has been in-person, which means that once the pandemic started and we stopped doing events for a few years, I started getting a lot less feedback until I was very far out of line or something was really out there. So, it's mostly been trying to navigate in the dark. Now that I'm able to go out and visit with humans again, it
becomes something that's a lot easier to dial in and get feedback on. It's nice to also be reminded by talking to humans that, "I love what you write," is a common thing that they say. People don't generally bother to send an email or a tweet about that fact. Instead, it's, "Here's your problem," so it becomes overwhelmingly negative. I'm learning to work through that. It's a challenging issue, just because originally, I was sending this to a few people and well, the audience got bigger with time.
AJ 15:14
Right, yeah, and kind of that constant every week, you're putting yourself out there, you are writing something, and you're making that commitment to, "I'm gonna see if this works." And then, only hearing back when there's a typo, that makes sense for our community. It makes complete sense, it's on brand for us, for sure. I know a lot of my friends, they get all of their AWS knowledge from your newsletter, like, that's where they're start is, that's their source of truth when it comes to AWS. And I think it's, again, a testament to the fact that you know what you're talking about, and it's not just snark. How does AWS feel about Corey Quinn and all of the newsletters and snark that comes there with?
Corey 15:51
Great question, because I've wondered that for a long time myself. It turns out that any large company and to me, a big company is one that has 200 people working there. Yeah, Amazon's a smidgen bigger than that with their 1.6, 1.7 million employees. Some people love what I do, a couple people, of course, obviously don't like it and take it very much askance and that's fair, but the vast majority of folks who work there have the most egregious response, which is that they've never heard of me yet and I find that it's simply untenable. By and large, people enjoy what I'm doing, or they're not subscribing and that's fine. I view myself as being someone in the relative cheap seats. No one at this company is required to listen to me, or the things that I say are not inherently right, just because I'm the person that says them. Increasingly, I find that when people have problems with what I write, the easiest way to fix that is to have a conversation with them and add a little context. Sometimes I'm wrong, sometimes I'm not, but it's always a conversation that leads to better outcomes as a result, at least in my experience.
AJ 16:52
Yeah, absolutely. And you've attended Reinvent in the past, I think you just came from RSA as well. At Reinvent, are you there speaking? Are you there evangelizing with potential AWS customers? I know you do a daily recap that gets posted on Twitter, but are you interacting with AWS there at Reinvent?
Corey 17:10
Oh, extensively, I tend to talk to people in a whole lot of different places. Reinvent has always been entertaining, I used to give talks there. These days, I tend to do my own media side show called, Requinnvent, spelled exactly like you think it would and that lives at requinnvent.com. But to be clear, we talked about disclosures at the beginning of this conversation, Amazon, Google, Oracle, and a few other companies out there pay me for advice around a lot of these things. I have existing business relationships with these folks and every single one of those agreements has always come with the explicit contractual term and understanding that you're paying for feedback, you are not paying for editorial control. And to their credit, none of these companies have ever tried to get me to stop talking about a certain thing. They've often tried to make sure that my understanding of what I'm talking about is fully developed, which is appreciated, but yeah, "Stop talking about x," it doesn't work. As soon as I start saying yes to that, I may as well just go work there. Eh, I'm not interested.
AJ 18:10
Right. I think there's a lot of people out there that are interested in seeing Last Week in AWS,
Requinnvent, Screaming in the Cloud, and the Duckbill Group continue and you not going to work at Amazon at all. You now are an angel investor, along with all of the many things that you have done in your past. You took a chance betting on young black founder trying to do something in the compliance space. Talk about your vision there for yourself in the investment space. Should founders start DMing you to pitch you on a regular basis here, Corey?
Corey 18:41
The way that I saw it, it was a problem that I dealt with previously, I was a SOC 2 control owner at a startup and I made a pig's breakfast of it, going through the various compliance forms for onboarding for financial institutions and the rest. I made the early days mistake of, "Oh, I'm just going to talk about AWS as if it were a data center," you can probably imagine how that ended up. I wound up having to go and talk to Amazon about, "Hey, can I give this large bank a tour of US East one?" Yeah, it turns out, the answer to that is no. Let me just save everyone a whole mess of time. And learning how to tell stories in a way that was technically accurate, but also wound up resonating with what auditors were looking for, that took a lot of energy from me. When I talked to you as a guest on my Screaming in the Cloud podcast, I was struck by the way that you talked about the problem, the way that you saw it, and you had a far more baked understanding than my half-blind, groping in the dark type of approach was,
so it was that you seem to know what you're talking about this. I kept you in mind and when I saw that you had fired off a hiring splurge, it was "Ah, any chance that round still has any room in it?" It's one of those “vote with your wallet” type of moments. From where I'm sitting, I try not to spend a whole lot of my time investing in other companies. You are also in that very sweet spot, where you are orthogonal to the industry that I spend a lot of my time in, but you're not central to it, to the point where I need to wind up disclaiming my investment in my interest every third time I write a newsletter or a tweet. It's far enough removed from what I do that I'm not beholden to the audience to wind up having to remind everyone that yes, I do have an interest in ByteChek. It's the perfect level of distance for what I do.
AJ 20:25
Yeah. And I would say, you know, one of the things that was really cool about having you in the round, aside from our relationship and that aspect of it was, I've sent out a lot of updates, I sent out an update recently about ByteChek transitioning to a four day work week, and you were one of the investors that responded to it and said, "Hey, I support this decision." And it means a lot to just have people that actually, like you said, are paying attention to these things where you send something out, and someone replies, like, "Oh, people do get this, and they actually do care." So, I think one of the things that a lot of, at least early stage startup founders worry about from investors, is just the level of engagement. What's going to happen? Are they going to be beating on their necks? And I've found, at least in your case, and other people's cases, that it's a lot more support than the other side, where obviously, you want us to do well, and you want us to succeed, but it's more than that. I think, especially at the stage that you invested in, you're betting on the person, and I felt that support throughout and I think that's a testament to definitely who you are.
Corey 21:19
The way that I see it, my role as an investor is not to sit here and tell you how to do your job. I don't have the bandwidth context or time to wind up giving any meaningful advice on that. If you take a look at ByteChek and figure, "Yeah, a four-day work week is who we are and what we want to focus on," you're almost certainly right, as opposed to my cheap seats approach of, "Well, more people work, the more good things happen. Go to a six-day work week and lock the bathrooms except during these times." Like, no, this isn't the Amazon Fulfillment Center here. You know how best to run your company, I'm just making sure that when I see things that are likely to be somewhat controversial in some quarters, I make my voice known as far as, "Yeah, I think that you're making the right choice." It's important to me that you treat people humanely, every conversation we've ever had has included strong elements of that. And frankly, if we're looking for things that are just gonna burn through people, well, my investment thesis is gonna have to change somewhat. I'm not too terribly concerned about it.
AJ 22:15
Right. Yeah, I think that's the piece about just company building that you've talked about that I
obviously care a lot about that I think is overlooked. We talk a lot about scaling. I think one of the keys to scaling the company is being able to retain employees and not having employees want to leave you every time they get ramped up and then, you're constantly just having to hire. People put a whole lot of focus on hiring and how fast you can hire and how fast you can scale the company, but one of the things that you hear so much about startup founders is how bad cultures are. And you think about it, it's this very young, inexperienced person that has a great idea, builds a nice product, gets a bunch of funding, and next thing you know, they're 27, 28 with 100 people that they're responsible for, and they're supposed to be a leader. Chances are, that's probably not going to work well.
Corey 23:00
No, it's an orthogonal role. There are a few different patterns of it, and all of them have their challenges. People are occasionally able to twist themselves into being able to fulfill that role. Other times, they step aside and have someone else come in. Other times, they wind up being able to go to where they want to be, without having to meaningfully deviate from their starting principles and how they got there.
I think that there are a lot of different paths, I'm certainly not going to say any of these roads are easy. I do know that on some level, how you wind up treating people in these moments, especially the tough moments, are the defining characteristics of this. Because anyone can say the right things when times are good. When you're starting to look at the rough moments, what do you do then? Well, that's the stuff that define a career and define a reputation. So, I don't have a whole lot of insight to give. We had 10 years of very good economic behavior. And now, we're seeing a bit of a pullback, and everyone's starting to freak out. Oh, okay. Yeah, this has always been written in the cards, that there's going to be a correction at some point. Honestly, I've never identified myself as an investor before, it's always a weird thing to me, to be very direct and irritate some people, I'm sure. I find that, "Oh, I'm an investor in these companies," as being part of a bio, what you're fundamentally saying is that the most interesting thing about you is that you write a check. And for some people, that is almost certainly the case, but for me, I aspire to be a little bit more engaging and interesting than that.
AJ 24:24
That has been the biggest thing and has been one of the weirdest things about this whole space for me is like, how much of writing the check is the personality of the investors. A lot of investors I speak to are like that, where I went through that raise and I just did not connect with a lot of VCs because I'm just like, "There has to be more to you. There has to be more to who you are as a person," but it's a weird space. I'll tell you that. It is a weird space to be in, especially nowadays, with the market and, like you said, what else was supposed to happen? It's kind of what I've been asking. We saw this coming, if you have been paying attention, this was going to happen at some point, and now there's all this panic and now everyone's really scared. I think what I've learned is it's posturing. The market was in a place where founders were in a great spot, we had a lot of power. Now, the market switching, and now the VCs have power. So, they have to make it appear that terms are going to be changing, the way this
process is going to work a little bit, you have to work a little bit harder. And I wish we can get away from the posturing. We're building companies, you all have the money to invest in it, let's just have the conversation without the posturing, but obviously, it comes with it.
Corey 25:28
From my perspective, it's also so much of the VC world is, "Well, I won a lottery once and as a result, I'm going to sit here and tell the rest of you how to win a lottery to win." It makes remarkably little sense from the way I see the world. It's always been something I do with a small portion of my investable assets, just for fun every now and again. I have no illusions about making this a full-time job, I don't pretend to know what differentiates a founder who's going to succeed versus one who's not. So, as a result, I just tend to bet on people that I enjoy talking to, that I have a good feeling about, and the problem that they're working on is not actively ridiculous. Compliance is one of those things that no one is excited about. No one gets up and says, "This is the job of our company is, number one, to become compliant with the relevant regulations." Because if you say that, there are suddenly a whole bunch of other questions that I feel I need to ask immediately, such as who's getting indicted over there? But it's something that companies need to do. It's important, it's painful, it takes a lot of time and energy, and anything that smooths that path seems to me to at least be a slam dunk. It's one of those expensive problems that I would pay to make someone else's problem, same as the AWS bill. So, I feel they're spiritually aligned, at least in that.
AJ 26:42
Unsexy businesses. You know, people always shoot for these flashy things, but solve a really important problem for people that they're going to pay a lot of money for. It doesn't matter if the 13-year-old is going to like your app, or the consumer that's 21-year-old is gonna like your app, that does not matter. Solve really important painful problems. A lot of times people ask me: How did you get into
compliance? Well, I was working in this space, and I saw that this sucks, and there needs to be a better way to do it and people were paying a lot of money, and actually were happy with how it sucked. They're like, "You're doing a great job." I believe this could be a lot better than what we're doing, if we had some software here to help us. I think that's great advice. Corey, one of the cool things that happened to you last year, you were featured in New York Times. What was that experience like, to be in one of the world's leading publications, talking just about who you are and what you bring to the space?
Corey 27:30
I was as surprised as anyone. I got the phone call from a reporter that I've spoken with previously, and he said, "I'd like to do a profile on you. What do you think?" And my response is, "Who is this really, because that sounds like an amazing prank, if you think about it," but no, it turned out to be real. He'd spoken to me about a number of articles that he had worked on before, and he enjoyed our conversations I suspect, in part, because I wasn't trying to sell him anything. I wasn't trying to convince him that, oh, he should instead talk about my company, for example. Instead, it was, "Okay, here's where your take is on the current industry and here's where I think you're right, and here's where I think you might be a little off base." But it's based upon what I would want to read as someone who didn't understand the industry myself, not, "Ooh, I'm trying to use this for self-advancement." And then, he offered to a profile on the at which point it was, "Oh, dear." And he did warn me, along the way, that this is not going to be a PR puff piece. We're going to be talking to people who might have negative things to say about you. And it's, "Wait? You mean, you're gonna talk to my dad? How's that gonna play out?" But I was very pleased with what came out of it, I was mostly worried that I was going to find out a whole bunch of things about myself that no one ever bothered to tell me. I try to be something of an open book here, and if you don't like what I say, please, my door is always open. I have a long history of not dragging people for criticizing me. Believe me, I deserve a lot of criticism for the things I say and the things that I do, but it was a really interesting experience, start to finish. I didn't expect it to get the level of attention that it did. I didn't expect the positive business outcomes that came out of it, and I'll be forever grateful.
AJ 29:07
That's amazing. I'm sure it was nerve wracking to wait between the time of talking and you know, like, you're like, "Oh, what are people gonna say about me?" And then it getting published. Was it just like, you were literally waiting for the day, or did it just pop in?
Corey 29:20
It got deferred a couple of times because of other things happening in the market, as well. So it's like, I'm sitting there and I'm not sleeping a lot that week and checking my phone in the middle of the night. And then, it finally hits and, "Okay, here we go." I certainly got some letters.
AJ 29:34
I cannot imagine the anxiety leading up to that. This has been awesome, Corey. One thing I want to finish up on, it's something that's common to both of us is, we're both fathers, and we're both relatively public fathers, where we share a little bit of our fatherhood with the communities out there that we're on. Just talking about, like why, for me, at least, I'll say at first, being a father is the most important thing in my life. It's the thing that I care the most about, and I think, oftentimes, especially in tech, you don't really hear a lot about the fatherhood aspect of what we do. You hear a lot about the other aspect and mothers in this field and how they're going, but dads are also going through a lot of the same stresses that everyone else goes through as parents. I think it's cool to see another dad out there sharing being a dad, and all of the ups and downs that come with it. A lot more ups, especially for us girl dads out there, but talk to me just about why you're open to sharing some of your fatherhood journey with folks out there and how it's played a role in your career.
Corey 30:29
I live something in the public eye, based upon who I am and what I do. And it's important to me that, when I do certain things that sometimes come at a cost, that I talk about in an effort to start normalizing it. Easy example, I don't even respond to text messages or Slack messages from my business partner on the weekends. That is family time, that's the end of it. I've stopped going to a lot of events in-person, which is easy to say now there's a pandemic on, but just on the grounds of there's always going to be another RSA coming to town, or there's always going to be another event I'm invited the keynote, but I'm not going to get these years of having young kids back. I want to spend time with them as they grow
up. The last aspect, as well, is it was a pain in the neck to find a way to codify this in a way that made sense in our employee handbook, but our ethics policy distills down to: I have two young kids. Someday, they're going to ideally asked me where the college fund came from. And when that day comes, and I explain, I'm not going to be ashamed of the answer. It's not going to be things like, "Oh, I wound up basically tracking my audience and selling their personal information on the dark web, or endorsing, or empowering things that I don't believe in." It might mean that, "Oh, why are we going to state school instead of a private school?" "Well, because I made some choices, once upon a time and given the choice, I'd make them again." Now, let's be clear, this is an incredibly privileged position. I'm not worrying about food on the table tomorrow as I make these decisions, but that does grant me a bit of flexibility to really be intentional about who I do and do not work with, how I wind up talking to people who are active in the space, and effectively, it's the question I get to keep asking myself: How do I want to be remembered?
AJ 32:08
Yeah, great question to ask yourself. I think that's amazing that you don't answer any Slacks or text messages on the weekend. I'm a pretty boundary-set guy where I set some boundaries, but I have not gotten to that level yet, though, Corey.
Corey 32:22
To be fair, if it's that important, he'll call me, but that's the nice thing, working with companies like this and dealing with billing problems. It is strictly a business hours type of problem.
AJ 32:31
Similar to our customers, like no one cares about SOC 2 on Sunday. It's not a thing that's top of mind, the world's not going to end if you didn't get your SOC 2report on a Sunday afternoon. I think oftentimes, the reason why people don't set boundaries is because they think they can't. And I think they're taking themselves a little bit too seriously, thinking that they can't take a break. And I probably could, I think that's a good thing for me just to have a little nugget in my head to say, "Do I have to respond to Slack? Do I have to look at these things? Can I take that time off?" I think I might be able to, and be able to get that space. And like you said, if it's a phone call, you know, they'll get through to you. But Corey, thanks again for coming on here, thanks for allowing me to be on the other side of the table interviewing you on my little podcast here. I definitely appreciate it. Any last words for the audience before we hop off here?
Corey 33:13
Fundamentally, the same thing I tend to advise everyone to do. Make sure that when you're making these decisions in the day to day that it aligns with your longer term, ethical direction. That's the reason I wound up deciding the ethics policy for the company well in advance of anyone trying to give me money for things that I would find unethical. It's way harder to say no when there's a suitcase full of money on the table in front of you. Figure out what your boundaries are and then stick to him. Without that, what have you really got left?
AJ 33:39
Amazing advice. Thanks again, Corey. This is a wrap for the To Comply or Not to Comply podcast. Thank you all for listening. And, like Corey says at the end of his podcast, please leave me a nice rating. And if you didn't like it, leave a five-star rating, if you did like it, leave a five-star rating and say really bad things about me in the comments of stuff. Thank you again, and I'll see you on the next episode.

Approachable Empathetic People Leaders with Andrew Alaniz

July 25, 2022 To Comply or Not To Comply