In this RedMonk conversation, Jack Bridger, host of Scaling Devtools and Developer Experience at Layercode, chats with Kate Holterhoff about founders. Jack shares insights from his interviews with founders on the importance of understanding users, overcoming fear in business, and challenges faced in the startup ecosystem. They also discuss marketing strategies around the role of differentiation, and the debate between bootstrapping and seeking venture capital, and the necessity of sales teams in DevTools.

Links

• LinkedIn: Jack Bridger
• X: @jacksbridger
• Jack Bridger, “I interviewed 100 DevTools founders and this is what I learned,” Scaling Devtools, 7 October 2024.

Transcript

Kate Holterhoff (00:12)
and welcome to this RedMonk Conversation. My name is Kate Holterhoff, senior analyst at RedMonk. And with me today, have Jack Bridger. Jack works in developer experience at Layercode and is the host of Scaling DevTools, which is a podcast that I was lucky enough to guest on last year, I believe. So Jack, thanks so much for joining me on the MonkCast.

Jack Bridger (00:32)
Yeah, thank you, Kate, for having me. It’s an amazing podcast and just listening to it today and it’s learned so much. And your episode was definitely one of the best ones we’ve had, especially on YouTube, very popular on YouTube. I think you talked about the rise of front-end developers as kingmakers.

Kate Holterhoff (00:48)
Ooh, is that right? I didn’t realize.

Yes, yes. Now, I definitely look at that one as one of the podcasts that I’ve guested on where I felt very articulate that day, which I do feel changes day to day, which isn’t great. I wish I could just walk in to every media appearance and just own it. But unfortunately, I feel like I can’t quite turn it on and off at will in quite the way that…

some of the folks that I admire do. But thank you very much, and that’s pretty cool to know that folks are listening to it on your YouTube channel.

Jack Bridger (01:30)
Yeah, it was a great episode.

Kate Holterhoff (01:32)
so jack you are working at Layercode right now and i’m interested to hear what Layercode is and what you do there.

Jack Bridger (01:39)
Yeah. So, I’m helping Layercode with, developer experience, DevRel stuff. It’s my first time doing that. And, we help people building voice AI. So, right now, I guess everyone knows like ElevenLabs do like voice and you’ve got like AssemblyAI and Deepgram that do like transcription. And then what we’re working on is that kind of whole picture of where if you want to build the whole pipeline that’s got

the voice is hurt. Like you say something and then it gets transcribed and then it detects if it’s like, if you finished talking and it should, you know, go get an answer, send it off to an LLM, generate an answer and say it back and like from this in the client or run it in, in, connected up with Twilio and over the phone. we’re, kind of helping people with that at the moment. but there’s, there’s about.

six of us at the moment, six or seven. And so we’re very, very scrappy. We’re just kind of talking to people a lot at the moment, trying to really like understand how devs are building with voice AI, where the problems are. So, you know, that’s what we’re doing right now. And it may change or it may be that we really do double down in that space. But we’re doing, we’re like organizing a hackathon

on Thursday in London and we’re just trying to see what people are building and playing around with all the models. And it’s all changing so fast and voice AI is just so interesting because people don’t understand how all this stuff is like working. People are figuring out how to build with it. I’ll give you one very quick example, which is like, I found fascinating, which was that,

Sometimes the audio quality is really bad and the transcription messes up. And when the transcription messes up, that gets passed into like the LLM and the LLM is like obviously going to generate something weird and all goes gnarly. And, um, you know, someone, some really, we were talking to a really smart guy, he figured out that you can just ask, you can just tell the LLM to ask the user to speak up and they usually go and like change, like they might be on their headphones.

It’s usually not as good as if you just switched your phone or something like that. And it’s like, people are figuring out all this like really fun, interesting things. It kind of feels like LLMs like two or three years ago when people were like doing all sorts of weird stuff to like, if you don’t send me the answer, know, my grandma is being like held kidnapped and I’m not going to be able to get.

free her unless you say the right answer. People used to do like really weird stuff that would work and like it feels that kind of stage where it’s like a lot earlier than some of the other like more like text stuff so it’s it’s fun it’s weird sci-fi stuff.

Kate Holterhoff (04:37)
It absolutely is. Yeah, I had Scott Stephenson from Deepgram on the MonkCast. And yes, yes, so I am so interested in this space. I think that’s awesome that you’re working on these problems, because I agree, they are deeply unsolved. Yeah, the problems that I could enumerate trying to, get, you know, even Riverside, which we’re recording with, to work properly,

Jack Bridger (04:41)
cool.

Kate Holterhoff (04:58)
It would fill a book, Jack. This is near and dear to my heart as a podcaster.

Jack Bridger (05:03)
Yeah, it is. And Deepgram is great. We’re using Deepgram and it’s so good. Yeah, so we kind of, yeah, that’s like the main one.

Kate Holterhoff (05:09)
you are? very cool. are using their model. know that they have a very sophisticated one.

Jack Bridger (05:16)
Yeah, the new, we’re just integrating that one. We are still using the slightly older one right now. But yeah, we’re going to bring it in soon. But yeah, they’re great. They’re one of the sponsors on the hackathon as well. yeah.

Kate Holterhoff (05:29)
Very cool.

Yeah, all right.

Shout out to Deepgram. That’s awesome.

Jack Bridger (05:38)
Shout out Deepgram

Kate Holterhoff (05:38)
Fantastic. OK, so I invited Jack on the MonkCast today to talk about founders, because it’s something that I guess I kind of take for granted on the MonkCast. We have founders on here, but we don’t talk about what it means and lessons about that. So I want to start by getting a sense, Jack, about why you have been so interested in founders on your own podcast.

Jack Bridger (06:03)
Well, I think it’s because I’m someone that’s founded two or three startups and some of them have done okay, but they haven’t really gone on to the kind of heights that I’d hoped. And so I think it’s that kind of like journey for like wanting to learn for myself what the best people are doing and trying to see if like, if that will lead me to, to be better. so the podcast is really quite a

in a way selfish endeavor, because it’s just, it is just asking questions that I have. And, and, know, but hopefully there are also a lot of other people that are trying to become better as founders, better in dev tools, better at growing dev tools. And so I think it does resonate. And I try to use that as the kind of the guiding light of like, would this be interesting to me? And if it is, it’s probably hopefully interesting to other people.

Kate Holterhoff (07:01)
Yeah, I think that’s absolutely the case. So many folks that we talk to are looking for those insights. And what I like about your podcast is that you collect them in one place and reflect on them. And to your other point, every podcast is selfish. mean, we’re all just here trying to figure things out. And they’re fun. Part of the medium, I think, is the fact that this is an actual conversation and not just, I don’t know, a of rote set of bullet points or a pitch deck or something.

Jack Bridger (07:32)
Yeah, absolutely. It’s more fun. I think, yeah, if it was just writing articles every week, I think it’s, that’s tough. And then also like one person doesn’t have as anywhere near as many insights as if you just talk to a different person every week, because they’re an expert in something probably. So yeah, I agree.

Kate Holterhoff (07:53)
I know, I like that characterization too, because it is like collecting all of these smart people into one place and having them reflect on something that is meaningful to such a large number of us. mean, even folks who don’t have ambitions of founding a company, I think are interested in what makes some successful and others not. I mean, we all…

have to interact with these companies on a day-to-day basis. And a lot of founders they’re larger than life. If we think about folks like Steve Jobs, there’s a sort of glamour and a magic to it, which is hard to put into words. And I think that’s why there’s been so many biographies written about these folks.

Jack Bridger (08:36)
Yeah, yeah, takes an interesting person to want to do it. Yeah.

Kate Holterhoff (08:39)
Yeah, okay. And so, Jack, I was really interested in your blog post, which you published almost a year ago today. You interviewed 100 DevTools founders, and this is what I learned. That’s the title. So I will obviously put that in the show notes here. I, you know, as I was reflecting on this, it was interesting to me that that blog post came out when a lot of folks…

through Y Combinator and just in the media were reflecting on what was called founder mode. Is that a coincidence that founder mode and this blog post came out at the same time?

Jack Bridger (09:17)
I wish. think it was just because I reached 100 episodes and Adam Frankl I don’t know if you’ve had him on the show, yeah, if people don’t know him, they should get his book. great. Developer Facing Startup. And he was VP of marketing at three different DevTools unicorns. And he calls himself the Triceratops on occasion.

Kate Holterhoff (09:24)
Yeah.

I have not.

Jack Bridger (09:46)
And, but he’s brilliant. And he, I had coffee with him and he was like, you should write an article that’s called, I spoke to a hundred founders and this is what I learned. And so that’s why I wrote it just because he was like, this is, this will be a great article. And it took a long time. I think I spent over a hundred hours on it. Actually. It’s like, it was, it was kind of just trying to sift through and see what, what, like, what did I learn? Because everyone says things.

in a different way and people, think there’s a lot of like recency bias and like what people are focused on at that time. And, also some things are very specific to what kind of like DevTools sounds niche to some people. I don’t have to tell you this, but like it, it like what works for one company doesn’t work for another one. And even if they’re in the same space, even if they’re both selling database products, look at like

PlanetScale and Supabase, just do their marketing completely differently. so it was trying to find the things that were actually common among this and rather than just listing out like 100 completely unrelated points from each episode. And I think the number one really that I took away, which was like, I think everyone…

succeeds does this is like talk to your users and it’s not a very novel thing because this is literally what YC say is like write code and talk to your users but I do think that that was like the most

common and also like meaningful thing. And this is also what Adam Frankl says in his book. His book is largely about building a technical advisory board and kind of asking people questions around if you could wave a magic wand at something, what would it be? And this is now that I’m working at DevTool startups, at a DevTool startup, Layercode, there was like the one thing that was like,

we, if we’re talking about growth, I don’t, it doesn’t feel like we should actually be thinking about, you know, writing, writing memes or, you know, trying to write really good content, trying to do any of these things until we actually really understand our users well. or for our case, it’s even not even users it’s about, because we’re really early. It’s like trying to understand the people that could be users and talk to them and understand like

Are we solving a problem that they actually care about? Or is this just way down the list of priorities? And I do think that if you don’t do that and you’re working on something that is just not a priority, it’s going to be such an uphill battle. And you do see it sometimes I do speak to some founders and I’m not necessarily their target audience, but if I kind of fall into a little bit, if I feel like it’s just, it’s just like a nice to have or something, it’s just.

you do get that sense that it’s just not gonna, it’s not gonna take off and no matter how good you are at everything else, if you’re solving a problem that no one cares about, it’s just like not gonna happen, I think.

Kate Holterhoff (13:07)
Yeah, I appreciate that because you’re right saying it’s understanding users. That’s the number one lesson. But it’s more complicated than that because you have potential users and all users aren’t the same. So understanding one user, maybe there’s some overlap with other users. I mean, I feel like an entire book could be written on that subject, which I assume that you’re occupied in at all of your free time, know, composing this book, understanding the user, you know, right, the paradox.

Jack Bridger (13:36)
Yeah. Yeah, that would be, absolutely. And, know, obviously like user researchers and stuff do this all day long, but I do think it’s hard though. One thing as well was like, and I don’t really have a good answer on this, but like there is that, there is this kind of contradiction. I’d be interested if you have a view on this, but there is this feeling that you should.

be a user and you should be the target audience. And I think that a lot of the founders that do well are building for themselves. And then, but it still feels like you should also talk to users, but maybe that is the kind of cheat code that if you are the user, probably a lot of your friends are also the same. And it’s just easier to just, you know, I think Colin from clerk was talking about how

at his, he didn’t do YC. did the, there’s another one in SF. I forget the name of it. But similar to YC and he would just watch people use Clerk and just ask them, you know, what, what are you doing? Like, why are you doing that? Like, what do you think is going to happen here? And so I don’t know. Like I think talk to you, talk to your users, ideally be your user.

easier I think as well but I don’t know it seems like the thing that’s the biggest driver.

Kate Holterhoff (15:12)
Yeah, I know. And that’s so tough, too, because it forces these founders to do it all, right? To not only be the charismatic leader that’s writing the blog posts that everybody wants to share on X or LinkedIn, but also they have to understand the financials in this fine-grained way. But then they’re also developers. That’s a lot to ask out of one person.

Jack Bridger (15:35)
Yeah. and, and then that’s also the other thing is that like, it’s, it’s really hard. And I do think there is some level of like, this is the really, like some people are very good and it’s like, that’s that’s like not such a fun topic, but like, I don’t know. You do see that like some of the people that do really well, just like, they are just so sharp and obviously so energetic. And it’s a,

I don’t know, like that’s the part that it’s hard if you’re doing a podcast on like how do you improve things? like, it’s like kind of hard that part because it’s just there’s some innate part to it think as well.

Kate Holterhoff (16:17)
Yeah. I think one of the things that I took away from this blog post was the fact that founders, often their first startup doesn’t succeed, and then they take those lessons to the next one. I’m thinking of David Mytton, who is the co-founder of ArcJet. He says something to that effect. And the lessons that they take to that second startup aren’t always the same, right? So he, for instance, talks about having a growth engine as being…

so hard, right? the idea of growing the user base, is, you more difficult than trying to get, a good product and, even getting folks to kick the tires. It’s like, how do you expand from there? How do you scale?

Jack Bridger (16:56)
Yeah, yeah, yeah, he, was.

Kate Holterhoff (16:58)
Do have a theory on second founders or repeat founders?

Jack Bridger (17:01)
I mean, yeah, I’m sure I think it’s you, learn to be better. I know for myself, like I just, it’s hard to, for that part, it’s really hard to be like an outsider. I guess like, so you can see that pattern that people started another one, but I know for myself, like my first one was better than my second one. you know, you do learn and I don’t know.

But I do think there’s also another case where like sometimes the pain of like why the first one failed is like the driver for the next one. like, WorkOS, like Michael, I know that his, his big thing was that like, he worked with Dropbox and that they, Box kind of took their lunch a little bit on the enterprise side of things. And I think he had this challenge as well as previous startup.

of like trying to build enterprise features, kind of, like seeing the pain of if you miss the enterprise market as well, like, I mean, I think both of those companies did well anyway, but like, can kind of lead you to like, okay, this is the thing I want to do next. cause I do think like there’s like maybe when, when they, when they do things, like, I guess most people’s first startup is often like,

something for students or, you know, like they’re building like order lunch when you’re on campus or something like that, like where it’s just like a problem that they see, but then they start building that and then they run into like other problems that are a little bit more like less obvious to people. And then probably that’s like a bigger business as well where like it’s just the space they see. But yeah, I mean,

It seems like most people that do really well have done other businesses. think Guillermo Rauch, for instance, like had sold a company to Automattic? The company behind WordPress and stuff like that.

Kate Holterhoff (19:05)
I feel like I cut you off when we were talking about David Mytton. Did you have any other thoughts on his quote?

Jack Bridger (19:11)
just the, like, on, David Mytton, part that really stuck with me is that, I had this really funny experience where like, I think it was the first time I’d ever been to San Francisco and, I was going to have coffee with Yoko from A16Z. And I was like taking pictures outside because I was like, my, this is like coming over from London. This is like, kind of like the church of like.

Silicon Valley, right? Like, and I went inside and I go downstairs into, she, takes me down to like this basement in the building. And then the first, the first voice I hear is like this East London accent. that sounds like it’s just like one of my mates at home. And it was Tony from Inngest. And then the second guy I met was David, who’s also British. And, they were just like both working down there in the workspace. And, David said to me,

growth is really hard. Like products is easy. I know how to build a product. Growth is really hard. And they, I think they do say that about like second time founders, like cliche of like first time founders focus on product, second time founders focus on like distribution. And, it definitely seems like that was his big takeaway. And I guess between those two startups, he was running console.dev, which probably gave them a lot of distribution.

People don’t know console.dev is like a really good newsletter on dev tools. send like a weekly roundup of different tools and they analyze like good things and bad things about them, which is that kind of USP. And he built this huge newsletter. So he obviously got very good at creating content and distribution.

Kate Holterhoff (21:01)
Yeah, that’s awesome. All right. So I want to make sure that we touch on some other points from this post, I didn’t realize that you spent so much time on it. So I certainly don’t want to give short shrift to any of the major points here. So I want to talk about this idea of the fear gap and the knowledge gap. So you mentioned that finding first customers often comes down to like fear rather than lack of knowledge. And I don’t know. The idea of fear in business is fascinating to me. would you mind, like, I guess, that idea out a little bit?

Jack Bridger (21:37)
Yeah, I think that some people, you know, I’m guilty of this, like think a lot about things and…

imagine all the ways it won’t work and they’re trying to over complicate it. Probably start a podcast, that sort of thing. Like start a podcast to become a better founder rather than just doing it. Right. so, other people, I think just do it and you know, like it’s that, I think there is this huge, like fear obstacle where I don’t think I,

Kate Holterhoff (21:56)
There you go.

Okay.

Jack Bridger (22:17)
I think it’s great if people listen to Scaling DevTools, like, please listen, you know, but I think if you never listen to it, it would be totally, you know, that’s totally fine. And you never listen to any experts, but you just go out and just try things and fail and like, you know, launch on Product Hunt, like tweet about something that you’re not necessarily, not necessarily people like put it in front of people. It’s kind of scary. Like

watching someone use it can be quite scary sometimes, like doing a demo, like when it’s quite early. I think Jake from Railway was talking about this recently that the biggest advice that he got early on in his career was just launch and just put it out there and like, don’t be afraid. I kind of questioned him a little bit on that, like he gave some really interesting answers that

because I was thinking, well, okay, that makes sense. And if you’re launching a social network, you know, go launch it fast, you know, test, see if people like it. But if you’re launching a database or, know, you’re launching like a media processing API or like something where people are going to build their businesses on top of yours, then, you know, maybe you should have a bit of fear. Like maybe you should be afraid to like afraid of this thing going down.

But his view was just that at the beginning, you know, it’s just inconsequential and you just got to put it out there fast. so I think when I say fear, it’s really, it’s about speed. And I think if you’re too afraid to put it out there, it’s just, you’re just wasting time. And people know this, everyone knows that like, it’s the kind of thing YC say all the time. It’s not.

unique stuff, but there’s a very big difference between like knowing it and doing it. think, and, can say for me personally, anytime I’ve just put like the worst that can happen is no one cares. And, it’s very rare. if someone insults you or like says it’s terrible, it’s actually usually a good thing. Cause usually when someone thinks it’s a terrible idea, someone else thinks it’s like a great idea. And that’s better that no one caring at all. I do think just overcome the fear, put it out there. Like, I think that’s a big, big one.

Kate Holterhoff (24:53)
Yeah, it struck me as huge. a thing that I tell myself pretty often is what’s the worst that could happen? And I feel like there’s an element of that. I also joke around with my front end friends about, you know, no one’s going to die because of an app, right? So, you know, whatever you need to tell yourself to overcome these, I don’t know, the debilitating fear that keeps us from doing what we need to do.

Jack Bridger (25:19)
Yeah.

Kate Holterhoff (25:19)
I think is valuable. So yeah, keep saying it. We need to hear it.

Jack Bridger (25:23)
Yeah. Yeah. I do think as well, sometimes like maybe spending too much time on Twitter is bad as well, like, cause it’s just like a personal thing. But I feel like, I don’t know if it’s just the algorithm, but I just see like so much like fighting and people like insulting each other and saying like, Oh, look at this company’s like blah, blah, blah. Like it’s just, I feel like if you just get that out of your head, like who cares? Like, I don’t know. It’s yeah. And all those people.

that are getting insulted, like usually they’ve done incredibly well anyway. like, you wouldn’t act, it wouldn’t actually be that bad to be in their position if it just feels like it when you’re like sat at home like, what if people say that this is terrible code or something? I don’t know.

Kate Holterhoff (26:09)
Yes, yes. The fighting on Twitter especially, or X rather, is, I don’t know, well known for that. And yeah, I can see how that would be particularly debilitating just to see that happening. Because yeah, I mean, it’s not real life, you know? It’s just a reflection of, I don’t know, a facet of what is going on that doesn’t, I don’t know, really have any bearing on the reality. And it tends to be, you know, the most

what bombastic personalities they get all the time. But I think you’re right on, it’s the algorithm. It has nothing to do with value or how articulate the argument is or whatever.

Jack Bridger (26:41)
Yeah. And it’s like a lot of the time this stuff is good anyway. Like I think like, it’s like easy to just not do stuff because you’re worried about like getting slammed. But often like, even when someone gets slammed, it’s like, usually it’s because they have a different perspective. Like I have this, like I see, I think the one I see the most is like databases, right? Like it’s like, they fight all the time. So you see like, yeah, like the…

Kate Holterhoff (27:15)
We’re talking to you database people.

Jack Bridger (27:20)
But I always

think it’s like, it’s always like, so the one you see a lot is like Neon and PlanetScale, like, and I’ve always liked fighting, right? But I always think that the fighting is good for both of them because it’s kind of like an ideological stance where like they just believe and focus on different things. like Neon, it seems is like really in on like, like vibe coding and powering like a lot of like, they’re kind of like vibe coding tools.

PlanetScale its whole thing is like enterprise and like just being really like rock solid and stuff like that. And so when they kind of fight, it’s like you kind of learn, okay, like you learn like what they stand for anyway. And so like, it shows up in people’s feeds and like, feel like it’s, they probably would, I feel like they’d both disagree on this, but like from an outside perspective, I feel like it’s good for both of them. And so.

I don’t know, this is a massive side tangent, but I think that often what we like, we get, I personally get like affected when I see this sort of stuff and I’m like, no, I don’t want to be the one that gets like insulted. But actually if you’d like step back and think it’s probably quite good for both of them. And if you’re in that position, then it’s great.

Kate Holterhoff (28:37)
I think you’re absolutely right. Yeah, I mean, was just talking to someone about Vercel and Cloudflare going at it on Twitter. So yeah, I mean, it’s constant. And that’s just topical.

Jack Bridger (28:44)
Yeah.

Perfect example.

Yeah, it’s like, and suddenly it’s like, are you Vercel? Like, are you team Vercel or are you team Cloudflare? And it’s like, but that’s actually great because they’ve collapsed the whole universe to being like Cloudflare or Vercel. But like, what about the number three one? Like, you know, no one’s talking about that. So like, you know, it’s good to be in the fight.

Kate Holterhoff (29:07)
Exactly.

Right, right, I know, and it brings awareness to both their products. And so, yeah, it seems like a win overall, even though maybe it’s kind of foolish. I don’t know. Yeah. No, this is good. I actually, I think this kind of ties into one of your other points, which is about the idea of differentiating your product and sometimes doing it in a silly way. So you use examples like Clerk’s van outside of YC and Wondergraph’s astronaut at conferences.

Jack Bridger (29:18)
Yeah.

Kate Holterhoff (29:37)
And I love these examples because I enjoy the more bizarre the conference marketing the better, know, the more outrageous the more fun the more whimsical, you know, all of this is for the good as far as I can tell. yeah, and so it seems like maybe this is also true online, right? So as long as you can differentiate yourself, maybe be a little ridiculous, you know, maybe draw a target on yourself. This is all, you know, this is all part of it. This is part of the game.

Jack Bridger (29:59)
Yeah. Yeah, I think so. It’s just like, stand out. Gonto (Martin Gontovnikas), who was the VP of marketing at Auth0 back in the day and like all the way from like, when they were really small to massive. he has this line, which I just love, which is like, it’s better to be different. No, it’s better to be different than be better. And meaning that like, you could focus on being like, if you work really hard, you might be like, able to write content that’s like.

50 % more concise and more explanatory than your competitor. Or you could just do something completely different to what they do. And I think he advised Clerk and they were just like turning up to YC with like a van and cookies and stuff. And that stands out. then I think other companies start doing it and it stands out less and you have to find something different again that…

I think that’s the, if you’re the one that’s like copying after everyone’s done it like 10 times, I think you’re probably not going to get much value, but like, think people were even talking about this today on Twitter about this like really flashy launch video used to be a differentiator. Now everyone’s doing it. So no one cares as much. And so it’s like, you’re always trying to be like different, which is easier said than done because

kind of takes a bit of confidence, kind of takes a bit of like, you know, risk appetite. And kind of also like being very, very in, I think it comes back to like understanding your users. Like if you’re very clued in to like, if you talk to your target audience every day, if you understand the cultural references that they like, or like, you know, what they would find interesting if you know, like, if you know that

the all the YC startups go through here and like they all need this. I’ve seen Mintify do stuff where it’s like YC survival pack and stuff like that of like if you know your audience very well then you you can be different while also like resonating but I think like if you’re just like totally off base and like just being a complete weirdo for no reason it’s probably not gonna resonate but yeah I don’t know like I think

definitely something to focus on. But I, again, now I do think that if you’re at the early stages and you’re just like focusing on this, it’s probably a bad use of time. But for most of the startups that do this have already gained some level of like adoption and found their target audience and stuff. Um, which also then makes it harder to be, to be different because a lot of the big ideas are driven by founders who, know,

have been quite unconventional people in their lives. But once you have a whole team and you have marketing meetings and stuff like that, it’s probably like, and you have charts and you’re measuring how much growth you got and what your budget was last week and stuff like that. Probably just gets infinitely harder to just, I don’t know, just say that you’re gonna spend all your marketing budget on an astronaut suit or something like that even though that’s probably when it’s most useful. I don’t know, it’s hard. Not many people do it because it’s hard, think, especially as the company grows.

Kate Holterhoff (33:38)
Yeah, it absolutely is. A thing that we end up talking a fair bit about a RedMonk is influencers and their value. I mean, I’m thinking of like Jason Lengstorf and his CodeTV and a lot of the fun things that he’s doing. I mean, he didn’t say it in quite this way, but what he impressed on me is this basic lesson of trying to stand out, trying to be fun, and finding those connections with some of these different companies that are interested in reaching developers. Yeah.

It’s not easy, but it creates this opportunity for the nexus of creativity and marketing that really seems to be gaining a lot of momentum. For instance, he mentioned that one of the sponsored little gimmicks was that Deno sponsored the dinosaur chicken nuggets, I guess, that they were eating.

Jack Bridger (34:20)
Hmm.

Kate Holterhoff (34:33)
I didn’t actually see that episode. I should look for it. I love this idea, because the dinosaur-shaped chicken nuggets are certainly an iconic food. And everybody loves Deno’s logo. That’s a strength there.

Jack Bridger (34:44)
So, so like they

filmed the lunch and it was chicken nuggets and they’re sponsored by Brilliant. Yeah, there you go.

Kate Holterhoff (34:49)
This is my understanding. Yeah. And they’re the official dinosaur chicken nugget sponsors. So anyways, I’ll have to dig this up. I’m yeah, I know it was it was was a cute idea. And I don’t know, I guess like leaning into the strengths is important. I’m also thinking of how Bun has this super cute logo as well. And, you know, and they do these amazing videos. So, you know, there’s

Jack Bridger (34:56)
That’s hilarious.

Kate Holterhoff (35:16)
There’s a lot to be said for trying to make sure that you’re reaching that audience. it’s almost becoming, I guess, a signal of investment in the product. If you’re willing to do all of these things around it that maybe aren’t tied to just the feature parity or whatever, that it signals that you’re going to be maintaining the documentation and that this isn’t going anywhere fast. All of these things are new ground.

Jack Bridger (35:34)
Mm-hmm.

Kate Holterhoff (35:43)
just in the sense of like, it’s not the sort of thing that, you know, developers, you know, had to or requested, right? It’s sort of unspoken that you’re looking for this, these fun ideas when you, you know, walk through the tables at a conference, right? And yeah, so standing out, I don’t know, I feel like it’s kind of an evolving thing. And so what it looks like is changing quickly. And I’m sure with like AI slop is only going to change quickly, more quickly.

Jack Bridger (36:13)
absolutely.

Kate Holterhoff (36:14)
yeah, I don’t know. It’s an interesting lesson and something that I’m seeing as well.

Jack Bridger (36:20)
Yeah. I think this AI slop is probably like a accelerant of this. think where people, if you can be immediately, obviously not AI slop, then it’s, it’s more valuable. And I think doing things differently is, is probably the way like, you know, just like an advert, like, did they generate this advert with like using the same AI audio generation as everyone else? No.

This advert is like, dino chicken nuggets. you know, it’s like, yeah, just doing it differently. I don’t know.

Kate Holterhoff (36:57)
Exactly. Yeah. Okay, very cool. All right, so let’s talk about content creation and the sort of dilemma around that because you mentioned it earlier, but you’re advocating for like founders to create content internally rather than like hiring content writers. So you’re focused on documentation at Layercode. Is that right?

Jack Bridger (37:19)
That’s a very big part of it. Yeah. Is this, there’s only six of us. it’s kind of, yeah. Yeah. There’s only six of us. So it’s kind of like, I’m the DX slash DevRel, whatever you want to call it person. So write some small amount of code, use the product a lot, write docs, like talk to users, like.

Kate Holterhoff (37:21)
big part of it. okay. so talk to me about like creating content. what does that look like? it’s on all of you. okay. man.

Jack Bridger (37:47)
help with marketing if we do stuff like organize hackathons, lots of random stuff. yeah.

Kate Holterhoff (37:52)
man, okay,

thanks for helping me to understand a little bit better about what you do. Yeah, but does that speak to that sort of larger idea from your piece on founders?

Jack Bridger (38:06)
So in terms of the job or the or content.

Kate Holterhoff (38:11)
Yeah, yeah, like

what, how you approach writing content. So we’ve talked about how to be different, but I feel like creating good content is its own subject. So I don’t know, like how are you taking some of that lesson to what you do at Layercode?

Jack Bridger (38:17)
Yeah.

yeah, I think, I think,

I think like when you don’t understand as I’m as I broken record, but I think like as someone, you know, what I’m going to say is like, talk to the people, talk to the users, right? You know, obviously I, you know, right now I’m doing like more like DevRel, but my last jobs were, you know, writing code as, as a, you know, software engineer, but I still don’t.

Kate Holterhoff (38:41)
to the users.

Jack Bridger (38:58)
understand the challenges of like, can’t be like, I get what it’s like to build with voice AI. It’s like a completely new space to me, I’d built some kind of like hacky things, tried to make like a Scaling DevTools, like voice bot thing. But when you talk to, when you talk to people building a voice, like they, they get things that would just never have occurred to me. They have problems that

Kate Holterhoff (39:04)
Mm.

Jack Bridger (39:26)
would never have occurred to me. They even just the terminology they use, like I was calling it transcription. No one calls it transcription. They call it speech to text. And it’s just like these small things that I think if you just dive right in, you’re like, start like trying to write like all the top 10 ways to, you know, make a great voice AI products. And then you just try to like,

Kate Holterhoff (39:37)
Mm.

Jack Bridger (39:56)
go Google around and like find what other people have said and just bring it all into an article. It’s like probably not going to do very well. Whereas if you go talk to like, you know, I mean, this is where probably like, you know, speaking to like you guys stuff like that, right. But just like really spending a lot of time talking to people actually building voice AI, take those insights, like share, share what you learned. Like that’s better piece of content or like just go build something and try to get beyond just like the hello world.

and write about the stuff that you learned and then maybe send it to a few people that have also built with voice AI. That’s going to be better content. But also at this point, you know, it’s always like a balance where I feel like we do do some content, but it’s also not like a huge priority for us right now because our bigger priority is like actually figure out what we can bring to the bring to the table that

is actually really helping people and solving a problem that people actually care about because, you know, we have a product and stuff, but like, I think we’d all say that we’re not at the point where we’re really able to just rock up and talk to like a serious voice, not just someone who’s heard about voice AI, but someone’s that’s really building with voice AI that’s really understands like all the different players. And we can say, okay, look, we stand for this.

this is where we’re better than these guys. Like this is where we’re worse. You should use us if this applies to you. And we’re not there yet. And so for us, everything is about just like getting to that point. And so the content is really like kind of a, like a few, like a side product of like a, what’s the, know, like if you’re, if you’re creating oil, you’re making, making petrol and you also get plastic or something like.

It’s like, it’s a byproduct. Content is only a byproduct for us right now. We’re like, so we’re just talking to users, not because we want to create content, but because we want to like make actually like a good product. And then we will also try and like share, like create articles about like what we’ve learned. Or like we might create a, we want to create a concept, some content on like real time, open AIs, real time API because

we think that that’s very interesting and we want to learn more about it. And like, if you write, create content, it’s like you learn about it because you’re forced to and stuff like that. But we’re not, we’re not very focused on creating content for the sake of it right now, because it’s like, I feel like it wouldn’t land anyway, probably. And if we were just like, how do we do Cause we just, I think until you really understand the space, like you’re not going to create really good stuff. I think, I don’t know.

Kate Holterhoff (42:54)
Yeah, yeah. Okay, fair enough. Okay, so I want to make sure that we don’t talk for too long about this, but I want to do some quick hits here. So another thing that you talk about is whether or not DevTools should be in San Francisco. So what is your take on that? Should they move to SF or no?

Jack Bridger (42:57)
haha

Okay.

I feel like it depends on what type of DevTool. Like, yeah, I think if you’re like, I don’t know, like it, yeah, no, basically no, you shouldn’t, you don’t have to, but I do think if you’re like, if you’re selling to all the DevTools and like cool San Francisco startups go to San Francisco, I don’t know, maybe like.

Kate Holterhoff (43:17)
That’s a fine answer.

Jack Bridger (43:38)
Probably is the best place to be, but you know, like not everyone is there like Supabase and PostHog, loads of like remote startups. You know, there’s some great companies in like London and Sweden and stuff. But I mean, yeah, it’s obviously the best place to be, but not everyone can go there and I don’t think it’s like the defining factor.

Kate Holterhoff (44:06)
okay? all right now i got another one. the bootstrap versus vc decision. where do you land on that?

Jack Bridger (44:13)
I think if someone who raises more money will like have a massive advantage over you because of like the scale, then you should raise money because if it’s just like a very, very, very difficult problem and it’s about speed and stuff, yeah, like, but if you don’t need to, then, I don’t know. Like this is, I used to have a strong opinion on this, but I just feel like

Just, I don’t know, like I’ve got so many friends, some of my friends, some of my best friends are like bootstrapped and doing really well. I’ve got a really good friend, Elston, who’s built this company, Tiiny.host, and it’s just like simple web hosting and they’re doing really well. He’s probably making like a lot of money personally. So it’s embarrassing him here, but I think he’s pretty public with his numbers and stuff and he’s got like a small team and he loves his life and

we grew up in the same town and stuff and he’s, he’s brilliant. But there’s also obviously like, if you’re, if you want to build a massive company, then you obviously need to raise like, obviously, but like, and it’s very rare. Like you have counterpoints like Atlassian and stuff, but I guess like almost all of the massive companies were VC. I don’t, I don’t know. I think just do what you do, what you want to do.

Kate Holterhoff (45:42)
It’s okay if all of the answers are it depends. So, but yeah, I appreciate hearing your personal journey with this, how it’s changed over time. So I feel like this is still working. This bit is still doing it for me. So this is good. Okay, last rapid fire question. Sales teams for dev tools. Do you need them?

Jack Bridger (45:45)
Yeah.

Okay, okay.

I think that they do need them. I’m going to say depends, I’m sorry. do they work? Do they work? Absolutely. I think like people often just think they just don’t work and they absolutely do. That’s just a load of rubbish. Like people that think that devs don’t get sold to are just like living under a rock, to be honest, because it’s like so easily disproved. I mean,

Kate Holterhoff (46:11)
Just lean in, it’s good.

Mm-hmm.

Jack Bridger (46:31)
You just go look at how many sales reps AWS has like, it’s probably like thousands. I mean, so if, if developers don’t buy stuff from salespeople, why does like AWS is not just like donating that money to poor salespeople, you know? So it’s like, I think that’s the biggest thing that I don’t hear as much these days, but I feel like a few years ago that was like quite.

in where people would just be like, it’s all PLG, like dev tools don’t need sales people. It’s like, well, I mean, it’s just a channel. It’s like, do you need to post memes on Twitter? Like, no, you don’t need to post memes on Twitter. You know, could it work for you? Maybe, you know, maybe it will work for you. And I think it’s just one of those where like, yeah, they, a lot of

DevTools should have salespeople. I think that the, even the, there used to be this thing that people talk about, like the minimum, like ACV for it to make sense to have salespeople. And the one I always heard when I, I worked in sales for two years and yeah, before I went into development, it’s kind of,

unusual. And at the time it was like 25,000 pounds for like $30,000 was like the thing that people would say is like the minimum deal size to make sense to have salespeople. But I’ve spoken to, I spoke to my old boss recently, who used to be the VP of sales and revenue, or VP of revenue at Stack Overflow. And big part of that was selling to developers with their team’s product.

And, you know, he was saying that you could, if you sell stuff that’s only like $900 of ACV, but if you sell, if you can sell like a lot of them or, you know, in a short space of time and it doesn’t take, it’s not like a complex sale, then you can have salespeople and like, so I don’t know, you can, you can definitely have them. And I think that probably seems like they’re probably underused because it’s unfashionable, um, among DevTools startups.

So maybe there is some like hidden, like maybe you can do well with sales people, because not many people do it at a small stage.

Kate Holterhoff (49:07)
All right, well, I think that’s a good place for us to wrap up. I’d like to end these things with inviting you to tell us where we can keep up with your musings, Jack. mean, obviously everybody should go ahead and subscribe to your podcast so that they can keep up with your latest guests there, but are you also active on any social channels?

Jack Bridger (49:27)
Yeah, am. For my sins, I am active on Twitter, X @jacksbridger. then yeah, check out Layercode.com and Scaling DevTools if any parts of it piqued your interest.

Kate Holterhoff (49:47)
Fantastic. Well, I’ve really enjoyed speaking with you, Jack.

Jack Bridger (49:50)
Thank you so much, Kate. It’s like so interesting. you know, I think as my theme was all about understanding your users, I think what you’re doing is RedMonk is really, really important. And, you know, probably I think DevTools, you know, spend investing money and time and research is going to be a very good investment. and

The podcast is great as well. So thank you for doing it.

Kate Holterhoff (50:15)
aww. that means so much to me. thank you. and it’s been a pleasure having you on.

Again, my name is Kate Holterhoff, senior analyst at RedMonk. If you enjoyed this conversation, please like, subscribe, and review the MonkCast on your podcast platform of choice. If you’re watching us on RedMonk’s YouTube channel, please like, subscribe, and engage with us in the comments.