Marketing Duckbill Group

Matthew: Hello and welcome to Developer Marketing Stories. My name is Matthew Revell.

Adam: And I'm Adam DuVander. Today we are excited to welcome Corey Quinn of the Duckbill Group. Normally you see and hear him screaming at clouds talking about Amazon bills, but today we are going to talk about the way that they get customers, the way that they work with developers, and also need to speak to that business leader audience.

Matthew: And before we speak to Corey, I'd like to just share with you about Developer Marketing in Practise, which is a programme of coaching and training that Adam and I are running. Now, if you are someone who is moving from marketing into developer marketing or you're looking to level up your DevRel career, or maybe you are a technical person, a developer who wants to come over onto the dev dev marketing side, then this is for you over a period of six to 12 months, depending on which plan you pick. We'll give you one-on-one personal coaching, and also we'll put you through a training programme. They'll give you the frameworks, the understanding, the concepts, and the measurements that you need to succeed in a developer marketing career. So go to developer marketing to find out more and to apply to be on the programme. Now though, we're going to speak to Corey.

Adam: Corey, welcome. We like to know if you could take us back to that moment when you decided to start Duckbill Group.

Corey: I think that that is a good way to view it only in hindsight where you look at the history of that anyone has done it seems like there's a path and plotting inevitability between this is where I went from here obviously to the next thing, then obviously to the next thing. I didn't have a freaking clue. It turns out I'm one of the best in the world at a very specific skill, which is getting myself fired by surprise from jobs. And after that happened for the umpteenth time, I couldn't stomach the idea of just getting the same job again with different faces because when you're in the DevOps face, it doesn't matter as much what the company does in most cases, whether you are shipping boxes or streaming bits, it really doesn't matter. Keep the site up and it's just a question of different tolerances. It is more portable between companies than most engineering roles. I suspect. The problem that I had was that, okay, if I don't want to do this same thing of running DevOps teams and being a DevOps myself, and that is how I singular it, you can deal with it.

Then I decided that there was, let's say something else. What can I do that let's me apply the skillset in a way, ideally as a consultant? Because one of my problems is when I get bored, I cause trouble, and that as a consultant when I get bored, that means the engagement is done and I can move on. So it was a question of, okay, what expensive problem would people be willing to pay a fixed fee for? And I know how to solve in relatively short order because as soon as you start billing by the hour, you're lost. When it comes to independent contracting, there's Jonathan Stark has this whole book series up Hourly Billing is Nuts and he's onto something in that sense, you're going to work aspirationally about 30% of your time as a consultant on the billable thing that you do.

The other 70% is stuff that you have to keep the lights on, accounting, marketing to new customers, servicing existing ones, relationship building and the rest. And I looked back at my own career, what problem did I have that I would pay to make go away. And it was pretty clear to me that the AWS bill was one of those things that cropped up at the least convenient time. It has not been baked into any of our planning. You don't get points for saving on it. There's no glory there. I just wanted this to go away so I can get back to doing the thing that I'm ostensibly good at as a DevOps engineer, who can I just throw this to? And there really wasn't anyone like that out there. So I figured, all right, well, we'll give it a shot. Worst case, I just do this for six months and then get a real job again.

Adam: Was there anyone who said, that's crazy. You've had these DevOps roles before. You know that it translates between companies because you just said that, right? Why not go and you get the next one?

Corey: Only one person, and everyone that I spoke to about this idea had a negative approach on it, and he was one of the founders of Heroku, I'm not kidding. And his exact feedback was, well, I don't see how you turn this into a $500 million exit. Okay. I don't think that that was in the list of things I needed in this life to be happy. I mean power to people who can get there and pull it off. I don't need a yacht fleet. I basically am okay with just paddling around in the backyard and a dinghy. Everyone else thought it was great, and it was, oh my God, I would love to be able to just go and throw that to someone else and not have to worry about it. I did talk to some people who led me down the wrong path. Joe Ruscio and Pete Chalo, both of whom were people in my orbit who themselves were terrific folks working on the AWS side themselves. Pete later became our first principal cloud economist here, and I thought this was the common case, not the exception case.

So I dramatically overshot where I needed to be in order to be convincing to the people that I was working with. And I mean, I was good at what I did then, but I look back now and I didn't know anything compared to where I wound up. I'm still learning things about this space that is mine. There's an entire, I guess, movement of fake it until you make it. That doesn't necessarily work. You have to actually have a skill because otherwise people are paying you for something you don't know how to deliver, and all you're doing is setting fire to your own reputation. In that case,

Matthew: Once you had the idea of what product or service you could offer, how did you find a way to describe that to other people that would make sense to them?

Corey: Positioning is marketing and it's deceptively complicated. It took me about two months to come up with the phrase that fits into a sentence. I fix the horrifying AWS bill, and that is very intentionally crafted. Most people who are happy will hear that and think, oh yeah, fixing the horrifying bill. It's horrifying because it's surprise and it's expensive. When you talk to finance, it's horrifying because of its lack of predictability and its susceptibility to be an unbounded growth problem. Whoever hears that takes away what they need to. From that statement. It took a bit of wordsmithing to get there and naming things is of course the devil,

Adam: And that does get it. An interesting point that I think is in many dev tools, which is those multiple audiences. I mean, you have the dev who you have one of their headaches, right? But you also have, in this case, the finance team's headache and it might be a different one for different dev tools.

Corey: Eight years in, I have not been able to track down the watering holes that the finance and procurement people consistently hang out at. Most of the way that my work tends to lead to engagement is someone in engineering brings me to their attention. When it becomes a problem, the AWS bill is a highly fixed point in time where people care about it. I can talk to you about it today and you could not care in the least about anything about it. We are recording this on October 1st. October 3rd is when the bills generally start to come out, and in two days from now, you're going to care very much about that bill because your boss is going to be screaming at you, great.

Three or four days go by and there's a new fire burning, but this one doesn't go away on its own. So in a week you won't care anymore. So there's a fixed point in time where you have to care. This is also partially why I don't just run my mouth on social media about AWS billing to the exclusion of all else. That is just, it feels too promotional. In some ways that doesn't resonate with me. It's a buy my thing, buy my thing, buy my thing. No, I want to build the audience.

So they stick around and every once in a while I will mention the things that I do so that I become synonymous with the problem in people's mental SEO stack. But no one is going to hang out if I just make billing jokes all day. I assure you they're not that funny.

Matthew: So you've made your social media personality for want of a better way, describing it, a part of you're very much a presence. Has that been a conscious choice of how to promote the Duck Bill group?

Corey: Do you think I did this by accident? I mean, honestly, it's one of those things where, yeah, my last job that I got surprised fired from was at BlackRock where their social media policy was shut the hell up because we are regulated and we will kill you with a stick if you get a regulator's attention. So I basically had to sit there and stew and keep my personality to myself, and when I went independent, suddenly I didn't have that restriction anymore and I figured, all right, I have a maiden name. I can go back to using my middle name. Corey Quinn can vanish into the ether, but I have to know, will my personality get me into the same amount of trouble that every mentor, coach, parent, teacher, casual acquaintance person I share an elevator with, et cetera, has told me it is for my entire life. They're probably right, but I have to know, and somehow it worked.

The humour is also, and I think people miss this, it's for me because I am profoundly ADHD and I get bored easily and want to move on to new and exciting things, keeping it fresh with how sarcastic can I be? What new humorous take can I take on this without crossing lines where I'm hurting individual people or just turning into a jerk? How do I tow that line and I do get it wrong. I want to be very clear. I'm not sitting here thinking, oh, I've never gotten it wrong and offended people I have and it sucks. And the trick to an apology is you actually have to mean it and you have to do better than you did yesterday.

Matthew: So if you were talking to someone who isn't naturally good at social media and getting out there, would you recommend that they just steer clear of it?

Corey: I had 1500 Twitter followers when I started doing this, and it took me seven years to gather them. So I assure you I was not doing this as somebody who was good at social media. The quick quip, the rapid response, the having fun in the town square really aligned with Twitter, I assure you, I have never yet found a way to make my brand of humour work on LinkedIn. Those people have no sense of humour. They're too busy, effectively affiliating themselves as best I can tell, and I just find the entire approach to be noxious. I have nothing but respect for people who can market effectively into that and have humour that works, but I just find it so soul sucking to be on that site.

Adam: So that sounds like follow the follow what does feel natural?

Corey: The hard part for me, it took me four years to realise and really internalise that screwing around on Twitter was actually doing work and not just me killing time waiting for the next thing. It's that old work ethic of I used to have a crappy boss who would, I'll never forget this. I worked at that job for 90 days, which should tell you a lot. Then I quit. At one point I was on Reddit looking up something on r slash CIS admin, and he wandered past and he is like, is being on Reddit really the best use of your time right now? And I was a director level employee and it's yes, yes it was, but I can't stand this. I have to find somewhere where I'm only accountable to myself and of course to my clients. But it turns out that if you upset clients and don't have a great outcome, word spreads word will spread either way and a significant source of our business is word of mouth referrals and people who hire me again after we had done a successful engagement with them or they had changed companies and or a contract expires, it's time to negotiate it yet again. It went super well last time. Come on back in. It's not that big of an industry.

Matthew: So you went from that initial, okay, I'm going to do this thing.

Corey: I did it for two years and then I hit a plateau. My business partner, Mike Julian was similarly doing consulting at the same time, and we'd been friends for a decade. He would introduce me as his friend and I would correct him and say, no, no, your best friend. He said that at one point on a recording, so I sound boarded it and I hit a button and I can interrupt him with his own voice saying, Corey Quinn, he's my best friend, and I do that whenever he gets uppity because that's the kind of jerk that I am. But he was doing his application performance monitoring consulting, which he was having problems with because when you are a consultant in the monitoring space, people like the advice, great, now go ahead and implement it for us. As soon as you get bogged down implementation, it changes the nature of what you're doing, and he was having trouble growing his business. As a result, I was doing just fine, but I lack process.

I'm always chasing novelty. I would have people express interest and I would forget to give them a quote for a project. We're talking just leaving money on the floor. We were here in this room for three days trying to figure out what us working together would be like. I had a revelation in the shower. I pop out soaking wet and I call him, I found the thing to collaborate on, come run my company, and it worked and we grew significantly beyond that. But as we're sitting here in this room for three days beating this together, I'm checking email periodically and leads are coming in and he stares at me. He's like, why don't you make a shit load more money than you do?

I was making a few hundred grand a year at the time, but yeah, again, by that point I was basically at replacement salary for senior SRE at a tech company money. The first year I was making 80 grand, and the hard part is living in San Francisco is at any point I can say, screw this. It's a Wednesday. By Friday, I'm going to have a job paying me that 300 grand a year at a big tech company and I don't have to do all this other non-core stuff that I feel like I'm failing at. I also don't recommend this path for most people to be clear, I'm here because it's really the path of last resort for me. If there were another path that worked for me, it would've been easier and I probably would've been less frantic chasing it down.

Matthew: Has part of what you've done to evolve the business over the years been going beyond that initial, I know you said it took two weeks to come up with the description of the elevator pitch of what you're doing, but two months. Two months, sorry, but if you worked on a broader kind of pitch over the years to win over the people who might be a bit more sceptical,

Corey: You know how I can tell that you two are very much in the engineering space. It's because you believe that the entirety of the duck bill groups business comes from me, the engineering side of it? Absolutely. Yes. I tend to have a significant outsized presence here, but it's not our only source of inbound leads. My business partner Mike, has a lot of following and a lot of respect in the finops side of the world, the procurement folks and the rest. I view the AWS billing problems through the lens of being an architectural problem, and for a lot of folks it is, but at a certain enterprise scale, which is now our bread and butter, it stops being an interesting engineering problem and starts instead becoming a central planning. How do you end up managing the AWS bill when you have 1500 different teams consuming it and you're not in a position to start passing edicts across the board? It's a different style, a problem, a different category of problem, but a lot of our engineering customers have become those larger customers. All roads lead to Rome, so to speak. I'm just more of a Remus in this case. Well,

Adam: And let's talk about some of the sources because you also have podcasts and newsletters and things, right? And those aren't, like you said, those aren't saying lower your AWS bill, the podcast, right? It's

Corey: Right. All of those things are things I wanted to exist, and the last week in AWS is a terrific example. I wanted to see a single point that rounded up all the news that was relevant to me and economic side of it, which is all of it from AWS discarded, the self-promotional nonsense that they throw in there all the time that they're, well, it's a partner thing, so great. Some partner in Dallas is super excited about a thing you've never heard of. Good for them. I don't care, and I put this out for, you're going to do it for six weeks. If I got 250 people to subscribe, I'd keep doing it. I didn't want to just be sending this out like a family newsletter or something.

Charity Majors tweeted about it two weeks before it launched, 550 people signed up and it's been growing ever since, and that is just an excuse for me to keep on. It forces me to keep up with what AWS is doing. It forces me to find new ways of being creative longer form, and don't underestimate this at all. I can wind up in people's email inboxes every week whenever I want to and I have something to say, and that means I'm not subject to algorithmic curation. I'm not at risk of de platforming when another douche bag buys a social media platform I use, it winds up really leaving me in control of my own destiny. The screaming in the cloud interview podcast. On the other hand, I almost didn't care in the first six months whether anyone listened to it or not.

It was an excuse to talk to people I had no business speaking to because can I talk to you about your AWS bill results in who the hell are you get out of my office? Whereas would you like to be on my podcast as I'm sure you folks are discovering means, oh great. Let me clear some time and we absolutely would love, I love that this out of my own voice. I'm going to indulge it wherever I can and it became something more than that. I'm almost 600 episodes in and I haven't gotten a DHD bored with it yet because every conversation's different

Adam: And now thinking again about marketers of dev tools, maybe they're not the face of that podcast, but what are some things you think that they could pull from that experience to help people buy their DevOps tool?

Corey: Well, part of it too is I didn't honestly know when I started doing all of this, whether it would be a sustainable business. There was a great chance that 18 months from then I was going to have to pivot to something else. Well, what am I going to need for that pivot? Well, I'm going to need an audience to tell about it. I think that people lose sight of themselves in the job that they're currently in. Done right. Someone who does developer marketing and engages with an audience will develop a bigger brand in their audience niche than the company that they work for, barring Google or something. Great people will follow you as you go through various things, and that is one of those things that is important. It can last a career.


I've always said that you can sell out the audience exactly once because they won't be around for it a second time, so if you're going to do it, make it count. Nesting doll yacht money, okay, maybe I'll have that. Maybe I'll wind up pitching multi-Cloud is a great solution and AI is everything, and now I'm an SVP at IBM for six months and then six months after that, no one will ever hear from me again. Yep. That's the selling out and taking the money and run doesn't interest me. That also means I've rejected sponsors over the years when they have not been able to successfully convince me that using their product as directed would not cause harm because I'm not going to sit here and show for something that's crap.

Matthew: Is there a tension between having sponsors on a podcast or a newsletter that is also there to drive inbound for your own company?

Corey: It's a good question and it's rare that we wind up having a direct call to action to come and buy things from us, but no one generally cares. I always tried to make sure that this podcast sponsor was not someone that competed with the guests company. That would've been a little on the awkward side, but it hasn't been an issue. I also worried unnecessarily as it turns out that, okay, I make fun of companies on Twitter. Are they going to not want to sponsor me? Well, AWS has been a recurring sponsor, so clearly it's not as big of a deal as I thought, and in something like 150 sponsors over the eight years I've been doing this, I've only seen twice where someone said, ah, you made fun of us on Twitter. We're not interested because what the intelligent marketers get, they really do get this, is that almost nobody is going to say, oh, I am not going to do business with you because Corey said something snarky about you.

But a lot of people will absolutely say, yeah, ignore the internet clown. This is the first I'm hearing about this company that could be useful for me and maybe it solves a problem that I have. I'm purely top of funnel. That's important. I also don't tend to misunderstand that a newsletter or a podcast is anything other than top of funnel. All it is doing is telling people about a thing that should already perform slash convert. I do my damnedest not to ever be someone's first experience with podcast or newsletter advertising because expectations are unreasonable, and if you don't have a functioning sales funnel, all I'm doing is taking your money away and I have this ridiculous idea that I could do more business with people over the long term than if I just do a cash grab once and then take the money and run an old timey business philosophy that our grandparents might've recognised

Matthew: Out of the newsletter, the podcast, the social media stuff. Is there one aspect that's that you think is more impactful for generating inbound than the others?

Corey: Absolutely not, because if I did believe that, I wouldn't do it. I would wind up focusing on the thing that works and that's it. I found that there is a bit of a funnel to this. Almost anyone at least once upon a time will click the follow button on Twitter. Some significant portion of them will sign up for an email newsletter. Some smaller subset will listen to a podcast and almost no one will sign up for consulting services.

Now, the difference between almost, and actually no one is enough to build a thriving business on as it turns out, but I found that meeting people where they are is the right way to do it. At least for me, the fast response witty quip on Twitter is great, but instead of sending a tweet, can you imagine if I emailed you all every time one of those thoughts crossed my head after the eighth email in an hour, you would absolutely be smashing that unsubscribe button and probably my face because shut up already. No one wants to hear it in this constant stream, so the longer form curated approach, okay, a weekly roundup of things I've seen that's a lot better.

I would also advise people don't make the dumb mistake I did and put the word weak into or weekly into the title of what you do. It forces a publication cadence. That has been a challenge. I took my first significant amount of time off, not including the births of my two children about two months ago. I took a six week sabbatical, spent about half of it underwater abroad, and it was great not having to think about this stuff for once. I hear this CrowdStrike thing didn't work super well. I don't know. Not my problem. I was underwater diving

Adam: And yeah, what happened for those six weeks to the things with weekly in the name

Corey: My business partner took over and wrote it in his own personal style for the newsletter and we just put the podcast on hiatus. Part of the challenge is the way that I've done this is it's very hard to scale in that people are intrinsically signing up for an email newsletter written in my voice and other people's material fits about as well as other people's shoes do. I've done some AI experiments. Can I get things to a point where it can possibly sound like me? And the answer is yes, but it just nails the snark piece of it. It doesn't have the insight pieces, and it's not just the shitty jokes that keep people around. Maybe there's a future where that changes, but I haven't seen it and I keep a relatively close eye on it.

Adam: So going back to a couple of things you said that I think people listening can pull something from, you talked about someone follows you, someone subscribes to the newsletter, right? As it goes down, those numbers get smaller, but if you can make the top wider that the numbers work out, I could see something similar with where at the bottom, someone signs up for your tool, your dev tool that you're marketing, but I think that expectation that you're asking for more and more of them in each step.

Corey: I don't have a process that flows people from one to the other. I'll periodically remember to tweet about the newsletter, sign up for this thing in the newsletter. I'll mention the consulting stuff. I link to all the podcast episodes, but there's not a hard sell, and I think that that is where people wind up getting it wrong. Maybe this works on some folks, but I signed up to a talker's email newsletter this past week where they sent out some piano lessons.

All right, that's an ADHD obsession from time to time. I'd love to putter around with it, and he's emailing me three times a day and it's a constant upsell to buy his course rather than delivering the value upfront, and it's written in that salesy dialect that just makes me instinctively cringe. I haven't unsubscribed yet just because I don't think of it at the moment, but I need to do that just because this does not resonate with me now. I'm not telling him he's doing anything wrong. He is targeting a much broader audience, and maybe in the aggregate this works better, but it's not me. One thing that's never been far from my mind is that when I write the newsletter and then record its podcast equivalent and then put that out every week, I'm taking roughly a year from humanity and consuming it. I have to respect that. I have to honour that where I can't just phone it in.

Matthew: It feels as though everyone we speak to on this podcast is saying the answer to developer marketing is have good product and have good content and have good relationships, and I wonder if we should just close it out there and that should just be, we should just put that on a website instead of having a podcast.

Corey: The end. Yeah. The problem is is that it's difficult to do that and it's impossible to do the relationship piece of it and authentically you have to actually like people. I wear my heart on my sleeve. It is never that hard to figure out what I think about something. Much to my chagrin. I realise that my face has subtitles, so my wife will periodically have to elbow me when I'm bored to tears in a conversation like, oh yeah, that's right. Put the mask back on and pretend I care what this person's talking about. I don't know how you sustain that, so I invite people that I want to have on the podcast. I talk to people who are doing interesting things.

I try to remember there's a human on the other side of anything that I'm making fun of. Now, there are people that sometimes misunderstand this and they almost have a parasocial relationship with their own employer where you are a $2 trillion company, give or take, and the fact that I said, this service that came out is not great for customers. I know you worked on it extremely hard. Terrific. It's still not where it needs to be, and customers depend on me to call that out. I'm not saying you're a bad person. I'm not saying your work was without point. I am saying you're not done and there's more work to be done, and some folks, more often junior folks tend to think that that is just me crapping on them unnecessarily. That is never my intention, but you don't get to choose how people hear the things that you say sometimes.

Adam: Well, and I think that gets to that authenticity and building that trust that I think is often missing on the marketing side because they want every message that goes out to be pristine and polished and have a link to sign up for their product.

Corey: Part of me wishes that I, instead of doing the a AWS billing thing, I focused more on a dev tool because that is more directly aligned with my audience does. I could actually convince people to buy that thing as opposed to go talk to your finance people about this place. It's a more direct shot, but I do know this about myself. I see ITing with sponsors, so it would have to be true for anywhere that I worked. I would have to believe strongly in the product itself because otherwise, what am I even doing here?

Adam: So say more about that. You think if you were in the sponsor's shoes, you would have to believe in that product.

Corey: Oh, if I worked as a developer advocate or for a dev tools company or a developer marketer for a dev tools company, I would have to earnestly believe in the product that I worked for, and that shows with some of my sponsors where I'll get the script and I'll just completely ignore it. Like, yeah, in hell with this, I'm their customer. I've been using them for a while. Let me tell you why I love them enough to give them money every month, and that resonates. Now, I don't tell them it's coming, and I certainly can't sell it that way because the first time I say that about something I'm not enthused about, remember subtitled face, it'll show and no one will believe me again, but there are products I get excited about. Tail scale is a great example. Local Stack is another, and disclaimer, I am an angel investor in Local Stack, so don't think that I'm just, that'll come out someday. It's like, aha. That small amount of money you put in is absolutely why you're shilling for them for years. No, I put the money in. I like what they're building. That's the way that that works,

Adam: And you provide feedback to a sponsor when they give you the script that looks like shilling.

Corey: I provide feedback on the internet whenever I use a product, so that's sort of the other problem of it, but yes, I also ask how much my team ask this because there's more than just me over here. People tend to forget that we are about 10 people give or take right now, and there's a piece of this where it's how much am I allowed to play with the script? There are times I will flat out say, I am not reading this script as written. You are unnecessarily picking on an individual despite the fact that they work in a big company like by name, no, I'm not starting a war with a distinguished engineer, full stop. There are things where, okay, you are saying something that is unsubstantiated and I cannot back it up. Your URL has five sub-levels in there. No one is going to read that. Let me give it a short URL, my snark cloud, URL Redirector, let's just use that. Everyone's happier for it and things of that nature, but I also don't necessarily tell people they're doing it wrong.

A perfect example, an early sponsor wound up advertising an ebook in the newsletter, and I was convinced it would perform terribly. It crushed it, and I know this because of what they told me afterwards. I'm not sitting here looking at deep analytics on this stuff, and it's rare. You find out from sponsors what works and what doesn't. I was also somewhat surprised that I have no tentpole, long-term sponsors that have been doing this for years. Everyone comes and goes. They'll come back, but people want to liven it up and migrate around. Good for them.

Matthew: You mentioned those after a couple of years, the business plateaued. I wonder if there are other setbacks that you encountered?

Corey: Lots of them. The question is which ones are germane to the audience? I'm a terrible manager. I learned that the fun way. I've found that I am very bad at doing rote and recurring things. A lot of what I do to scale myself is anything that doesn't need to be me. I delegate to a team member. Getting an EA was transformative for me, but these are all down the path things. I think that there's also the idea that if you don't love what you're doing and you start waking up dreading work, it's time to change things up a little bit.

There are times I go on significant long sojourns where it's all right, I'm going to just spend a month learning this new technology that a customer's using just because it's an excuse to get hands on with something. I did a dive the start of this year and picked up Kubernetes for the first time because I ostensibly lost a bet with the internet about its relevance five years later, and I gave a conference talk on it. It went super well, and I still run a Kubernetes in my spare room because I continue to make poor choices, but it was a fun diversion from the constant all cloud, all cloud, everyday cloud type of problem that I ran into. Find ways to play with it, find ways to mix it up, be a genuine, authentic person. I think we're craving that authenticity right now seems to be in short supply.

The only time I really ask people for money directly is my annual charity t-shirt drive that winds up raising money for 8 26 national, the creative writing programme for kids. I'm not here selling various screwdrivers or whatnot. It doesn't make a lot of sense for me. Something I considered and rejected after I did the economics was, what if I made a version of the newsletter paid member only? It's a seductive idea, but this is tech. The long-term value of a sponsor, two-way sponsor of someone getting the newsletter, becoming a prospect, becoming a lead by becoming a customer for that company. Given the size and scale of these enterprise deals, one success story pays for sponsoring everything I do for the next 10 years. The long-term value is insane, which means that I can charge commensurate sponsorship rates, which means I punch above my weight. For the audience size, one of the best ways I can think of to diminish that value would be to charge too little for it. Oh, just pay me $5 for this. Great. Doesn't make sense.

Well, what if you just write the same thing but have a paid version without the sponsorship ads? You can't do that with the New York Times either, and there's a good reason. Think of the pitch for half a second of, Hey, you want to advertise in this thing where the most engaged most well-heeled people with disposable incomes can pay not to see the thing that you're talking about. Do you want to sign up? It's a terrible pitch, so it just leaves me twisting in the wind where I don't put a tip jar out. It's just I want you to spend a lot of money with me or no money with me. I'd rather charge nothing than only a little bit because it devalues everything else you do attendant with it.

Adam: Okay, so let me have you put on your cloud economist hat for a dev tool here then, because oftentimes you hear dev tools are going upmarket. They want to sell to the enterprise, but then there's this seductive self-serve that I as a dev want to be able to play with it too. Should someone be thinking about the five $50 a month, whatever the low plan is, if they're maybe getting some interest in free or open source usage, should they try that or should it be about setting the sites on the big deal?

Corey: It's highly dependent on the nature of the business in question and the tool as well and the general shape of things. It is a significant weeder function to just weed out the folks who can successfully transfer a dollar from their bank account to mine for one. Another mistake that I see people making across the entire industry is mistaking enterprise problems as just small and medium business problems that are scaled up.

It's a different category of problem. Are you sure that the thing that you have built respects the nature of the enterprise complexity, both organisational and technical? Do you have the full court press to wind up doing a sales motion to enterprise folks? I have the easiest sales pitch in the world for an enterprise. If you pay us money, you'll turn a profit on that engagement in the first 20 minutes. Most of the time it is a slam dunk ROI story, and it still takes months and months and months to go from prospect to closed deal. It takes time. It's slower and there's a lot more moving parts that have to be addressed, whereas someone who can self-serve, sign off the website, great. Awesome. Is it expensive to serve as those customers? I don't know what percentage of them start becoming significantly larger customers. I don't know. If you only want to have large enterprises use your thing, then the only people who will be using it and talking about it are the small folks who go through that entire sales cycle.

If you have something that's available for anyone to kick the tyres on and play with, then there's going to be much more of a network effect tied to that of word of mouth, people telling other folks about it, assuming that it's good and solves a real problem. What I also see is a lot of tools that look frankly quite derivative where, oh, it's an observability tool. You're the what? I have 20 of those already. Which ones do you replace, but we're the 21st. Great. Maybe it solves a problem, but I have a hard time believing it just because I've been sold to that same bill of goods so many times. Differentiate yourself. I've never been a big fan of doing what everyone else is doing.

Matthew: You mentioned that long sales cycle. Do you have a process of how to keep those prospects engaged throughout that and you said you've got like 10 people. Do you have dedicated sales and marketing people who help progress those relationships, or is it mostly you and other senior people?

Corey: Yeah. Do I have a process? Absolutely not, but April Palmer, our head of sales sure does because she's very good at these things in a way that I am very not good at these things. I get brought in for some of the high level conversations, absolutely, but I am bad at remembering to follow up with things I just learned.

It's a common ADHD failure mode where it's like, oh, it's been eight months since we talked. It's so good to hear from you. It's like, frankly, I forgot you existed completely until you showed up in front of me. Oops. That is not the stuff that great sales relationships are made of, and that's not something that I ever was particularly great at, but there's a story. We have multiple sales and marketing folks who work on that extraordinarily well, and that is their skillset. I'm not going to take credit for their work. I'm bad at it.

Matthew: Some developer tools, companies or infrastructure companies or whatever will have one or two people who are very, very much in the face of the company. They're very prominent in particular communities. I wonder if you as someone who plays that role for Duck Bill group, if you have advice for marketers on how to reign someone like you in when necessary,

Corey: In what sense? When is it necessary to reign someone in? I mean, when I have a strong enough opinion, the company will adjust to accommodate it. I am the company when you own it. You can do an awful lot of things like that.

When it comes down to you need to spend more time talking about these things, well, okay, let's have a discussion on how that looks. It's a collaborative experience across the board. It is not necessarily something that's going to be generic where, oh, just tell them to tone that part back. Don't worry. When people spend a fair bit of their time talking about things that aren't directly germane to the thing that you do, I mean, okay, maybe get concerned about that if they're on a keynote stage at a big tech conference, never mentioned a thing that you do. Okay, that seems like a foolish choice, but there's given there's take for everything. People are never one dimensional.

Matthew: I was just thinking right now we have one particular experience or situation while we're recording this, where a very prominent member of a particular open source community is potentially doing damage to that community standing

Corey: As a WordPress user. Myself and WP Engine customer, I've been working with WordPress for a long time. I ran it at large scale at Media Temple before GoDaddy bought and killed them. I have a lot of love for the WordPress community that their founder is currently setting a fire because the takeaway is not WP Engine bad and wordpress.com good. It's this whole platform is inherently unstable and there's no separation whatsoever between the foundation and the company and the dictator for life who runs the project, and that makes me very hesitant at this point to move forward with anything.

WordPress, we run our sites on WordPress, and now I'm really thinking hard about whether that's going to be the case for the next thing I do. So yeah, when someone goes completely tilting at a windmill like that and basically sets fire to the reputation, that's not exactly the common case, and that's a scenario where, okay, you're a developer marketer and you need to reign in someone. How do you reign in the head of the company? That's a tricky thing to do.

I've always had relationships with my team and tell them on day one then, okay, great. If you think I'm going too forward a particular direction, please say something. I may not agree with you, but I'll hear you out. That's the way that this works because other people's perspective is extraordinarily important. Even folks who are on his own side, this, in this case, Matt Mullenweg, are absolutely taking away from it a sense of, Ooh, he is really not doing this in an intelligent, thoughtful way.

Adam: One of the things you had mentioned about reigning someone in is allowing that freedom to talk about things that aren't specifically about the product, and can you talk more about why that is important for them to do?

Corey: Because if you don't have someone doing that, then it's pretty clear that every answer that they have to anything, any question they respond to is going to be, oh, this product, it does everything. I think that if I can't find an example of a developer advocate pointing out something where their product is not fit for a given task, then I have to question everything else that they're going to tell me.

There is always a use case where this is a terrible way to do it or the product is not ready yet. In that sense, if you lie and tell me it is, I'm going to find that out during the proof of concept super quickly, and I'm not going to believe you a second time when you tell me things. There are cases where we have to go ahead and get in front of everyone and talk about ai. Do you really, because there's a lot of fatigue about that going on in a lot of communities right now, the community of people who have ears.

Matthew: So Corey, as we come to wrap up, I'd love to know if you were able to give yourself advice. Do you eight years ago, knowing what you do now about how you've promoted and brought Doug Bill to potential customers? Is there anything that comes to mind?

Corey: Sure. Not sure how Jermaine is for other folks, but I would've separated my own brand a little bit more from the company sooner. We've been attenuating it for about half of the company's life now and it's going reasonably well as evidenced by this conversation, and we're doing that in such a way that it is not broadly entered the awareness of folks.

Everyone has a different perspective on the thing. People look at our team page of who works here, and I swear some people are convinced that everyone else's job is to sit there and clap while I do everything. That is not how it works. I do not have enough hours in the day for anything reasonably approaching that, but I would say delegate more and sooner. Obviously don't tie everything you do to a weekly cadence that doesn't go well, but other than that, that everyone's going to have an opinion on what you're doing, but you have to live with the consequences. Make the choices accordingly.

Matthew: If someone hadn't come across you before now, which seems unlikely, but where would you direct them to learn more?

Corey: That becomes a separate problem as well because, alright, now there's so many different places. Where do you drive people for the analysis of AWS News last week in aws.com, duck bill group.com, if you care about AWS bills at Quinnie Pig on social media, if you enjoy shit posting.