In this conversation, Jason Lengstorf shares his journey from aspiring rock star to tech media mogul with Kate Holterhoff, senior industry analyst at RedMonk. Jason digs into his experiences at IBM, Gatsby, and Netlify—and he doesn’t hold back. Jason discusses the challenges of navigating corporate structures, the importance of community in open source projects, and the impact of venture capital on innovation. He also reflects on the current state of GraphQL and front-end frameworks including Next.js, Astro, and Gatsby. In this conversation, Jason outlines the importance of long-term planning in leadership, the challenges executives face in maintaining focus, and the value of doing the ‘boring’ work that improves products. Finally he shares thoughts about his latest project, CodeTV, including insights on innovative content creation in for developer audiences.
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Transcript
Kate Holterhoff (00:13)
Hello and welcome to this RedMonk conversation. My name is Kate Holterhoff, senior analyst at RedMonk and with me today is Jason Lengstorf. He is alumni of Netlify, Gatsby and IBM and is currently killing it as a creator, educator and online personality. Jason, thanks so much for joining me on the MonkCast.
Jason Lengstorf (00:31)
Yeah, thanks so much for inviting me.
Kate Holterhoff (00:33)
All right, so I’ve given the high level LinkedIn bio, but I’d like to hear all the things that I left out. So how do you typically introduce yourself?
Jason Lengstorf (00:43)
Hmm. Well, the fast version is I wanted to be a rock star and that didn’t work out. And so now I’m here. I started out as a musician and I did touring very heavily for a few years back in the 2000s. We were playing about 200 shows a year. And when that didn’t work out, you know, we got to the conversation with record labels and realized that there was no way we were going to be the next big thing. So
I looked at what I was doing and what I wanted to do next and I knew I didn’t want to start another band. I didn’t want to be a musician. just unfortunately economically did not work out. So I looked at what my other skills were and as part of being in the band, I realized I had been operating an agency with a single client. I was doing design, was doing web development, was doing marketing, I was doing street team, community work. I was like, oh, I think I could do this for other people.
So I opened an agency and I started doing that work under a banner, I called it Copter Labs, and then that went for about 10 years. Got little burned out on agency work, got myself stressed to the point where I started having like health problems, and so I realized I needed to get out of that and got a job at IBM where I joined as, you my plan was to be a cog in the machine and just sort of not stress about work. Failed miserably at that, immediately like,
pushed a big project that got me on the radar of a couple of the executives at the company and then spent the rest of my time at IBM at meetings arguing for the permission to do some work that I thought was important. So then I left and went to to start up land, know, like Gatsby. and I joined, I think I was the one of the first 10 people there. And when I went to Netlify, I was one of the I think 75 ish was was the number I joined at. And, you know, just kind of
rode that out until I ended up doing what I do now.
Kate Holterhoff (02:24)
Amazing. And so you focus on the front end here. How did you end up doing that? Are you a self-taught programmer?
Jason Lengstorf (02:31)
Yes, I started because I, you the band needed a website, right? And so I was kind of muddling through that. This is back in the very early 2000s. So CSS was brand new, right? Like I remember building table-based layouts. And every time I built it, I had fun. So I would try to do it again. And I wanted to do something that was cooler. And then I needed to find a way to put our music up. So I learned Flash. And then I wanted the band to be able to update. So I started learning backend and I picked up PHP and MySQL.
It just was always, I could build it one, I could add one more thing and saw that as an opportunity to take it a little bit further and I guess that’s just sort of my personality is if I can do something, I wanna do it all the way and so I kinda keep tugging at threads and learning new skills and before I knew it,
I’d accidentally built up a skillset that was valuable.
Kate Holterhoff (03:18)
Whoops.
No, this is all very good. you know, since I clearly need to go on Spotify right after we record this and check out your band, what band were you playing with?
Jason Lengstorf (03:31)
You’re gonna regret this, but it was called Minus My Thoughts.
Kate Holterhoff (03:34)
Okay, I look forward to all the regrets.
Jason Lengstorf (03:35)
And when you hear it,
I’m the one making those terrible sounds with my mouth. I was the singer and they gave me a guitar to keep me from dancing.
Kate Holterhoff (03:40)
You’re the singer.
my God, I love this so much.
What era are we talking about here?
Jason Lengstorf (03:49)
This was like the Screamo’s Screamo punk era. So around the same time that bands like Fall Out Boy were big, that was when we were doing our touring thing.
Kate Holterhoff (03:53)
yeah.
Wow, this is so exciting. All right, no, I got plans now. Okay, yeah, no, my three-year-old’s gonna love it. This is happening. Okay, so I wanna go back a little bit to talk about your time at IBM. So you were overly competent, it sounds like, to the extent where you were on a trajectory to the moon.
Jason Lengstorf (04:01)
Yeah.
Kate Holterhoff (04:19)
And I wanna know, were you doing front end development while you were there?
Jason Lengstorf (04:24)
Yeah, got hired as, I can’t remember what the official role was, but it was like somewhere between senior and principal as a front-end engineer. And then I ended up being more or less the front-end architect for IBM Cloud. Because the first project that I took on was we had a dashboard that was just really slow. It took over a minute to load. And so I looked into the architecture and I found that it had
It was one of those projects that just had been handed across a lot of teams and everybody added a little bit more on top and people didn’t really want to dig into the bottom. And so I just rebuilt it. I took my team, we kind of planned an idea. I had a really supportive manager who was down to let me try stuff. And we built a prototype of how we could sort of, they call it the, I think I’ve heard it called like the strangler fig pattern where you sort of lay one app.
on top of an old app and then slowly that layer takes over and you can just shut down the old app, right? So it’s sort of a way of incrementally replacing a piece of software so that you don’t have to rebuild all of it at once. You don’t have to get the full, you know, the full green light to do a complete refactor. You can just build something one piece at a time. And so I basically talked my team into shipping that and we saw, it was like a four figure percentage increase in load time.
Which, like, and I need to be clear, this isn’t because I’m a genius, right? This is just because we took the time to look at the problem and we broke it down into, into like, what’s actually wrong and how can we correct that? And then we built it from that standpoint as opposed to like, what have we been told to do and how can we get it done as fast as possible? So that was a really big win. And then that bought me the bandwidth and the sort of the organizational
capital that I was able to pitch another idea that was a little more ambitious. And that was the one that got me onto the kind of company radar. It was at the time GraphQL was brand brand new and IBM is a company that has lots of teams, lots of projects, and they all have to communicate because they’re all interrelated. And you know, in any big team like that, usually the biggest bottleneck isn’t the software, it’s the communication. So this
What I saw was that GraphQL offered an opportunity to standardize that communication through a single point. And so I built this out with my team. We got the proof of concept in place and then we managed to onboard a handful of teams into it. And when people saw how that was working, it made a huge difference in the way that those teams were able to function because they were looking at a single point of truth instead of having to update 30 teams whenever they made a change on something. And so…
That obviously, like there were teams that didn’t want to do that because they felt they would be losing control of things. And so there was some politicking that happened there. And then there were some VPs that wanted to be the ones who could say that they were the ones who led it to fruition. And so they were kind of arguing over who got to be in charge of it. And also the stuff that I was doing was we were starting to touch the trickier parts of the app and everybody wanted to like double, triple, quadruple check that that was going to work. And so
It sort of turned into like a bureaucratic slog there at the end.
Kate Holterhoff (07:28)
Are you still bullish on GraphQL? I feel like the luster has faded a little bit from that.
Jason Lengstorf (07:35)
I mean, think the thing about any one of these technologies is that they’re all intended to solve a particular problem. And GraphQL is a way to solve communication about data layers at scale. And that’s why it was invented. It came out of Meta because they have a lot of teams that have to be able to share data in complicated ways and you don’t want to have to make bespoke endpoints per service or per UI. And so GraphQL lets you kind of…
custom craft and you can introspect it and get details about what things are and there’s really clear communication about when things are deprecated or moved. And for that, it’s still brilliant. I think what we did wrong is we did what we usually do in tech and we’ve done it many times since where something new gets invented and we say, if it’s good for one thing, it must be good for everything. Throw away all past technology, it was a mistake. We only do GraphQL now.
And when you introduce any technology like that, we’ve seen that happen like we’re doing it right now with AI where instead of building useful things with AI, we’re trying to make AI everything. So it’s mostly garbage with a few good products that would have done a lot better if we would have just focused on the use cases that worked. We did it with crypto. We do it with everything. And so it was, think GraphQL had its hype cycle and now it’s just a useful tool.
Kate Holterhoff (08:49)
Yeah, that’s very politic. I like how you didn’t answer the question. That’s on brand.
Jason Lengstorf (08:59)
I really like GraphQL when it is in the right circumstances.
Like if you have a problem that GraphQL solves, I love it for that. Don’t try to fit it into a situation it doesn’t make sense in. That would be my advice.
Kate Holterhoff (09:11)
Yeah, I like that. Okay, perfect. Yes, so it depends. Wonderful. All right. Absolutely. That’s the only kind that we work on here. Okay, so let’s talk about your time at Gatsby and Netlify. So what was your role there?
Jason Lengstorf (09:16)
The most engineering answer ever.
Gatsby was an interesting one. They they hired me without a job title. So they they basically said we want you to come here because they they thought I would bring something to the team and and so Gatsby, mean, you know as as anybody who’s been following that company knows they they sort of had a spectacular rise and then a even more spectacular crash Where they were kind of taking over the space and then they just managed to fumble every single bag along the way
until they eventually got broken down for parts. And that is sort of, think, maybe something that we could have seen right from the outset when they offered me a salary and had no job description, right? But what that was interesting for, and the reason that I was excited about the role, is that they basically said, come here and figure out what our biggest problem is and then solve it. And that got me into community work. So I showed up and I realized, we’ve got great engineers on this team.
We have no shortage of people who can technically solve problems, but nobody understands how community works and nobody is doing the work to make the people who, it’s an open source project. It is 100 % dependent on the community wanting to be part of it and we’re not doing anything for them. We’re not making the community feel like they have ownership or that they have input or that we’re listening or that we care. So let’s fix that. And so I started building out programs both through technology and through just
community organizing to make the open source contributors feel like they were very much a part of the team. And how do we grow a for-profit company out of an open source project in a way that doesn’t feel like we’ve suddenly gone at odds with our open source users? And for a brief glorious moment there, it was working. And then, you know, things go the way they go and all the things I was working on started.
Started getting undercut a little bit and I did the best I could and and there were a lot of great people there who kept up the Good work for a long time after I left but at the end of the day, you know, like you There there are certain positions in a company that you just can’t overpower and and if they are not seeing things the way they need to be seen It ends the way that Gatsby ended
Kate Holterhoff (11:29)
And you’re a repeat entrepreneur at this point. I mean, you’ve spent a lot of time in leadership roles and seen how companies can thrive. Did you take away any lessons from that?
Jason Lengstorf (11:39)
Yeah, definitely. think the biggest lesson that I learned is, you know, a big frustration for me in venture capital culture in general is that we have reified engineering and we will say things like, you know, somebody has a brilliant business plan and we’ll say, okay, but don’t talk to us until you have a technical co-founder. However, if a technical person shows up and they say, I built this cool toy, they don’t ask, do you have a business plan?
They don’t ask, have you ever run a business before? They don’t ask, do you know how to manage a team or how to, I don’t know, inspire anybody to follow you. They just say, here’s $10 million. And then when you start to ask these people, how are you going to turn this into a business? The engineers will say, we’re gonna build a solution. And the VCs seem to say, we don’t care, we’re playing the odds. Like they’ll either figure it out or they won’t.
and we’ve invested in enough companies that we expect that most of them won’t figure it out. Which is more or less verbatim what a VC told me when I asked him this question. And so to me that’s a very concerning way to approach this industry. And it’s really driven home for me that we can’t treat engineering as like the end all solution. Technology is only useful in so far as it solves real problems. And if I’m basically creating a company that
that funds my hobby of playing with new tech, there’s no way that’s gonna turn into money, right? I might be able to briefly create a hype cycle that gets people to give me a bunch of venture capital, but it will eventually fall apart when somebody says, great, how does this generate revenue? And so I think it’s, for me as an entrepreneur, it really drove home that like, I don’t care how neat the tech is, I have to have a plan for like, why does this exist?
who wants it and how am I gonna make sure that I can get it to people in a way that they find valuable enough to pay for? All the tech in the world isn’t gonna solve those three questions for me. And so now that’s been a huge determining factor in like why would I work with a company? Why would I start a company? Why would I do any of these things if I can’t provide very clear answers to those questions? And it’s also a really good like filter for
When you’re talking to somebody about, you know, what are their business plans or what are their ideas or what do they want to build? You know, if they’re not addressing those questions, to me, that’s somebody who’s, need a business co-founder if they want to go into business and make something. Or they should go find a company that needs like a head of R &D or, you know, somebody who’s not running a business, somebody who is playing with tech so that somebody who knows business can then take it and turn it into something.
Kate Holterhoff (14:14)
I think what’s interesting about that answer is it makes me think a lot about the state of front-end frameworks right now. I think it was Vercel that was paying someone like $8,000 to maintain one of the frameworks, and that was like per month. And so there wasn’t like an actual employee working on it. So it seems like the business model around frameworks and how they’re being supported by
Jason Lengstorf (14:33)
Mm-hmm.
Kate Holterhoff (14:38)
some of these entities that are actually making money, the Vercels of the world, the Netlifys, the Renders, whatever, the frameworks sort of get short shrift in terms of support. And so I wonder about that legacy and how things have maybe changed in the past five years. Are you seeing a big difference in the way that front end frameworks are being supported by more commercial VC backed ventures?
Jason Lengstorf (15:02)
I mean, I think the part that’s been hard is that we ran the, they called it the zero interest rate phenomenon for a while where we just assumed that money was free forever. And so if it was for developers, because developers were so high in demand, there was obviously money somewhere down the road. And so we saw people just dumped, like what does Vercel valued at? Something like $3 billion? There’s zero chance.
that they have enough revenue to justify that valuation, right? They just raised off of hype. And I think that’s true of so many companies in the space where they get these unicorn or what do they call them now? Binocorns when they’re two billion, whatever. Like we just keep making up new words, but these companies that have like in the low millions in revenue with these multi-billion dollar valuations and zero plant.
Kate Holterhoff (15:42)
Yeah
Jason Lengstorf (15:55)
You know and you’re like, okay. Well, what are you gonna do? They’re like, I don’t know AI is cool Maybe we should make something for AI and it’s like that’s your plan. How are you valued at a billion? it and you know, it is what it is, but the thing that I found really difficult is in the mid 2010s Open source was that like AI every company saw if we build a popular open source framework then question marks and then profit and so they saw the you know, the React thing where we Meta was able to kind of
take over the whole developer mind share by releasing React and GraphQL. And they kind of saw these big things happening where they were really able to dominate and hire. But I think what we were thinking like, you can sell pick axes to the miners. But open source isn’t a pickaxe you can sell. It’s specifically something that you release to gain mind share, to get people to come work for your company. It’s a big company like Affinity Play.
So to start an open source project from zero and expect that to be profitable somehow almost inevitably means you have to go build a cloud, which is what we saw Netlify do. It’s what we saw Vercel do. It’s what we saw Gatsby try and fail to do. It’s what we’ve seen all of these companies do is they build some kind of thing that you then have to pay them monthly to host. And so it builds incentives in these companies where they have to make something that
generally hamstrings their framework in order to force people to pay them. And in some cases they get that really wrong. Like in Gatsby’s case, they basically broke Gatsby unless you bought Gatsby cloud, which is why Gatsby died. And in Vercel’s case, they’re playing really dirty pool with Next.js where they force all the ecosystem maintainers to build like out of the source code, like custom hacks and adapters to make Next.js run off of Vercel because they know
that the money is in getting people to bring their Next.js projects to Vercel. So if they make that easier for people to take it off, it directly affects their bottom line, right? And they’ll say that they’re not doing that, but they’re like the source code, the actions are much louder than words here. And you know, if they wanted to be open, they would have an adapter layer like Astro or Svelte are the ones that are truly open. And so the thing that I worry about and the thing that the thing that I think is is sort of being demonstrated in the
the bit of a downturn here is that we’ve become very dependent on open source in this way, but we have not figured out a way to fund it. And so ultimately what it’s gonna probably come down to, and this is the part I’m worried about, is that the giants are gonna end up kind of owning these frameworks, and some of them will be good at maintaining it. Like Facebook is good at maintaining React because it runs their core product. But if IBM were to suddenly buy
SvelteKit or Astro or one of these frameworks that’s out there, they’re not running it as like their main money-making service. So how much maintenance is it really gonna get? Like we saw this with Netlify. Netlify bought Gatsby and it’s effectively gone dark as a project because Netlify has no business dependency on Gatsby. It was sort of a boondoggle for them to grab. that is what I’m worried is gonna happen is that we’re gonna see sort of a collapse of open source, like funded open source.
because companies are basically gonna grab it because they wanna be a big company that owns a framework and then they’re not gonna have it tied to their core business use case. And so eventually the business always wins and anything that’s not core to the business gets pushed to the side and becomes sort of like a when we have time, which is never. And so it kind of goes back to what it was originally, which is a group of volunteers doing stuff when they have time and building stuff that’s cool. And hopefully maybe this time we don’t inject millions of dollars into it and break it.
Kate Holterhoff (19:33)
on the volunteers note, I found the news article that I was thinking of. as Vercel was sponsoring Astro, they’re sponsoring at $5,000 each month towards ongoing open source maintenance and development. as a sort of, I don’t know, I guess if you’re not going to acquire the framework, which maybe there’s some good to that, allowing them to remain sort of indie projects. Yeah.
Jason Lengstorf (19:40)
Mm-hmm.
Well, and Astro
itself is a venture funded company. so Vercel is, is spending by, well, I think they’re not anymore. think Netlify actually one upped them and paid more. But you know, Netlify and Vercel have been fighting over who gets to be the Astro primary sponsor for a few years now. But the, you know, the outcome is, is like they’re paying into their foundation, which they use to pay their volunteer open source maintainers, which is currently the best model I’ve seen.
Kate Holterhoff (19:58)
Good point.
This might be old. Yeah.
Jason Lengstorf (20:20)
Like I think Astro does it better than most. However, at some point Astro is going to have to make money. And I just don’t know how they’re going to do it. Like they tried a database play that didn’t work. And so what happens next? And it’s just hard to say because at some point the board is going to say, all right, you’ve had enough time. It’s time to make money. And this is what kills every startup because you kind of watch the turn. The startups…
Kate Holterhoff (20:20)
Okay.
Jason Lengstorf (20:45)
They they they’re running they’re killing it. The community loves them They’re doing so good and then the board says time to deliver like deliver revenue and they float in some kind of like COO other like spreadsheet guy who cuts all of the things that made the open source project work because they can’t draw a direct line to ROI and then they’re all confused when the project starts to fail so they cut harder and and then you know, eventually it just falls in disrepair because that’s you can’t run it like a
You know like a hedge fund. It’s not about like finding efficiencies open source and community are human centered things and Efficiency in human centered things doesn’t it doesn’t work the way that it works on a spreadsheet the the efficiencies are in scale and you have to be willing to put money into the communities in a way that you know does create ROI like you know if you go and spend a bunch of time
being kind to people, if you spend a bunch of time treating people well, that always leads to better outcomes. We see it personally, like when we get job offers or our friends come and recruit us when they go work at cool companies. We see it professionally when you go to an event and you meet somebody and your sales team has a chance to have dinner with the prospect that you couldn’t get to take your call and suddenly they’re interested and they want the demo because they spent some face-to-face time. Like we know that this stuff works, but you can’t draw a direct line.
to, funded a bunch of local meetups or we found a way to empower a bunch of younger developers to learn. And then six to 12 months down the road, they go make a choice at their company that they just got hired at to bring our tool in, which does turn into conversion, which does turn into money, but you can’t attribute it, right? And so those programs all get killed because they’re too squishy. But that really is what makes it bottoms up developer led growth motion work.
It just doesn’t compute in the Hedge Fund private equity spreadsheet mind, you know?
Kate Holterhoff (22:42)
And so you’ve seen this in practice during the acquisition several times. All right. You’ve seen this repeatedly.
Jason Lengstorf (22:45)
Several times, unfortunately. It’s the same, it’s the same,
like it’s, what happened to Gatsby. It’s what’s happening right now at Netlify. It’s why Netlify went from industry darling to having effectively dropped off the map. Like they don’t even get listed anymore. When you talk about hosting, it’s, Cloudflare, it’s Vercel, It’s AWS. Like where’s Netlify in that list? They’re gone. And it’s because they cut all those programs.
Kate Holterhoff (23:07)
And I’m interested in what that transition was like during the acquisition because yeah, Gatsby was just so well known for treating its developers so well, maybe too well. They were the ones who would pay you to interview, correct?
Jason Lengstorf (23:19)
That was a program. I that might have been my program. That was something I pushed for was like, if you did a take home, we paid you for the hours that you did the take home because we didn’t… My argument was we didn’t need somebody to do a take home. We could figure out if they were qualified for the job based on how they talked about code and how they reviewed a piece of code and all that. If there was an insistence to do the take home, then just pay them. I think we fix it at like 70 bucks an hour. We just pay you for the time. If you’ve got four hours to do this, we’ll pay you…
Kate Holterhoff (23:24)
well.
Jason Lengstorf (23:49)
280 bucks, you know, so that you’re not, so that you get paid for making the effort. And like you had to get through a lot of rounds of interviews. It’s not like we were just offering 280 bucks to everybody who applied to the company. It was, you know, we probably paid 10 people per interview, per job opening to do the take homes.
Kate Holterhoff (24:06)
Yeah, but right on. mean, that’s great. It seems exceptional too. Did others start doing that after you?
Jason Lengstorf (24:12)
You know, I’ve seen a couple people do it and the thing that bugs me is that like this is this is one of those things that it’s so easy to become legendary as a company because the bar is underground. we like offering somebody $280 to interview at your company because they’re going to do four hours of unpaid work. Otherwise is not that is not a complicated thing to do and the amount of money that you will spend on hiring and recruiting and getting
Kate Holterhoff (24:14)
Okay.
Jason Lengstorf (24:39)
You know what I mean? Like you’ll spend so much money on contract recruiters, on posting on job boards, on all those things. If you pay people to do their take home, they will recruit for you. They’ll tell everybody about how good the experience was. And that was what we had. We had people knocking down our doors to come work at Gatsby because they heard how good it was to work there. And as soon as those programs fell apart, everything else did too. And I think this is the part that’s really hard is like,
You’re never done building a good company. You’re never done building a good reputation. the instant you take the, like you are always applying effort. And as soon as the effort eases up, everybody, you know, people just go, I guess that’s not a focus for them anymore. And they’ll look for who’s caring.
Kate Holterhoff (25:20)
Right. What was it like after the acquisition? How long did you stay at Netlify?
Jason Lengstorf (25:26)
So this is actually the irony of it is I left Gatsby long before the acquisition. I left Gatsby in 2019 and I went to Netlify. I actually intended to leave Gatsby and do what I’m doing today, this like independent content thing. But Sarah Drasner hit me up because she was the VP of Developer Experience there.
And she said, you should come to work for my team. And I said, no. And I found out later that when we got off that call, she looked at her husband, she goes, just wait, he’s coming. And sure enough, she called me again and she was like, listen, you have always worked alone. You’ve always done all these things. You’ve all had all these opportunities to grow. And so I went over to Netlify and I got to work with Cassidy. I got to work with Sarah. got to work with.
Tara Manicsic and Phil Hawksworth and it’s just this absolutely fantastic team, right? And then when Sarah left, she tagged me to be the next VP. And so I ended up taking over that role. did the best I could. I don’t know if that was the right thing for me to do. Like executive leadership is a whole different skill set. It was the first time I’d ever done anything like that. I’d been a manager several times in the past and like,
You you only know what you can see right and and so there’s there’s always the you get your own blinders when you when you do a job But what I actually quit over was the Gatsby acquisition And not not in not entirely but like I I had been making the case internally at Netlify that what we really needed to do was double down on
Kate Holterhoff (26:56)
Go on.
Jason Lengstorf (27:04)
the way we interacted with the community. And so I was advocating for, let’s make our company conference feel like the Academy Awards. Like, let’s really go in on the production. Let’s get behind the scenes. Let’s do red carpet. Let’s have, a kind of a sports center desk where there’s running commentary about, you know, add some color in between talks and, explain who these people are and what they do and why what they’re talking about is interesting. Let’s do…
Actual good commercials like let’s bring developers into our fold and like come up with funny stuff about what it’s like to be a developer and make commercials. Let’s do custom content. I wanted to make you know reality TV about companies building using these new techniques that we were pioneering at the time. You know the Jamstack thing at Netlify. I was like let’s get companies to come and do a Jamstack build and show the process like really follow them and do like a reality documentary kind of thing.
And they were into it. Like we got a couple of those things done. You we did a remote conference during the pandemic that was sort of Saved by the Bell themed. It was super fun. Cassidy and Phil Hawksworth and I got to do a, you know, we dressed up in nineties gear and we customized a suburban house. And there’s a whole story about that and all the things that went wrong with it and how we managed to pull it off. But then, you know, they did some commercials.
We dressed up Phil Hawksworth like a robot and did a series of like, what if your tech stack was one of your coworkers and kind of shot it like The Office. And we dressed up my wife, Marissa Morby, we dressed her up as a developer in two universes, one that was very like drab and kind of businessy and one that was a little more like fun and startupy and said what it’s like to work with and without Netlify and followed this developer in two universes across their day. And those were super fun, right? Good returns, people were really understanding what we were doing.
And then the board just decided it was time, Netlify needed to be profitable. So they started looking for like ways to become profitable and solutions were like, we should acquire Gatsby, we should do this. And I was like, no, we should not do that. We should double down on this. This is working. And they, we just couldn’t agree. And so I ended up leaving to go independent. They ended up acquiring Gatsby and as you can see Gatsby kind of has faded into nothing. So, you know, I’m not going to say I told you so, but.
Like, yeah, just, I mean, I still love the Netlify team. I have a lot of love for that team and most of my commentary is just born out of frustration because I know what it’s capable of and it’s just hard to see. It’s hard to see anybody you know who’s like, they’ve done something so good. Like it is objectively one of the best things on the market and they just cannot figure out
Kate Holterhoff (29:17)
This is a safe space.
Jason Lengstorf (29:41)
how to focus long enough to tell anybody about it. It’s such a bummer to see.
Kate Holterhoff (29:44)
So that was your foray into executive leadership, is that right? Okay, and so what were your takeaways in that domain? How did it differ from other management positions that you had had?
Jason Lengstorf (29:47)
Yes.
Um, I the the thing that I think scared me the most when I went into executive leadership is I had always assumed that the people in the VP the SVP the C level jobs were like these extraordinarily seasoned and and just almost clairvoyantly experienced people and When I got into the role, I was terrified that I was just gonna be so outclassed
because I figured I’m, you know, I’m walking in, I’ve been an engineer forever. I’ve only really not been an IC a handful of times and usually for not, not very long. So what am I going to be able to bring that they don’t already know? And then I, when I walked in, I think the big shock for me was realizing that like the people in executive positions are, are typically the people who sort of wouldn’t back down from the unknown. And that is a really good quality.
but it does not mean they know what they’re doing. And so, so many of the meetings that we had were the VPs in the C-level at Netlify staring at a whiteboard going, what the hell do we do? And then we’re just, know, is there an expert we know who has some insight to this? Is there a pattern that we’ve seen before that we could try? Like, how do we navigate this? And so we’re, you know, we were all bringing our best efforts, but we had…
And I’ve seen this now that I’ve had the chance to talk with more executive leadership teams and especially in what I’m doing now, I have a lot of calls with founders and VPs and stuff and it’s just the same everywhere. Nobody knows what they’re doing. And the thing that’s really hard is we all have our past experience to draw on, but there is no such thing as clairvoyance because every single one of these startups is in a world that’s never existed before. And every time some company, you know, when chat GPT came out,
The world changed in a way that every playbook that existed before Chat GPT is now a little different. You can’t run it the same way. When the pandemic happened, same thing. All the things that worked in 2019 don’t work anymore in 2020 and beyond. So what’s the playbook now, right? So all we have is our combined experience and then our instincts about how we can get similar results in a new world. And that’s sort of
You know, that’s why I was pushing toward this media thing, this TV for developers thing, is because my hunch is all the value that we were getting in 2019 when we would go to conferences, sponsor local meetups, et cetera, et cetera, we’re not gonna get people to show up at local meetups right now. I think that appetite’s coming back. I think in a couple years, we’re gonna see that come back in a big bad way. But right now, it’s not there. So where are people connecting? It has to be online. So how do you get somebody to connect online? You make something they haven’t seen before.
It can’t be another webinar or another live zoom call or another, you know, we all, all the developer content looks exactly the same. So how do you stand out in that noise? Right. And, and so I’ve veered away from what you were originally talking about in, in, the, I think on the executive front, what I really learned is that the, the thing that I’ve started to really admire in leaders is their ownership of not knowing and their willingness to
to have conviction in their guesses. Because what I’ve found causes the most pain in companies is that so many leaders aren’t quite sure what they should be doing. And instead of gathering evidence, making a plan, and then seeing that plan through to then measure, they gather evidence, they make a plan, they start it, they get nervous, and they change it. And so you can never really execute, which means you’re never getting feedback.
And so now the company is this in this constant state of turmoil where you don’t have results to measure against you only have well, what can we deliver in three days because that’s how long the attention span is before the plan is going to shift. And that’s really not a productive environment for anybody to exist in. So leaders who can make long term bets and by long term, I mean like six to 12 months. Let’s like, let’s not be ridiculous here. but if you can commit to an idea for six months and say, we’re going to try this. And if I’m wrong, if I’m really wrong, you should replace me.
But if I’m only kind of wrong, let’s measure why, let’s figure out what happened, what we thought would happen, where’s the delta, what’s not happening, and then let’s make a different plan. But if we never get through the plan, then we don’t know if it would have worked. Like any sufficient marketing effort is gonna take six months before people even understand that you’re marketing, right? So to try a marketing effort for three weeks and then say, well, that was a failure, new marketing plan, there’s no way to ever get success.
in that world. And I think the same is true with products, it’s true with engineering organization, like anything that you’re doing, you have to have the patience and the conviction that the plan was good enough when we made it.
And we don’t have good enough information to upset that apple cart. We should see it through and then keep all these notes about things that we think might be better to then use when we’re doing the retro on what happened. And so to me, that’s sort of the thing I’ve tried to take as like my executive leadership experience is it’s not my job to know. It’s my job to be confident enough that people can trust me to let them do work under a given plan for long enough to get results.
Kate Holterhoff (35:11)
That seems to go across a lot of the organizations that I’ve seen as well. Usually has to do with hiring on a new person in the C-suite who maybe gets rid of the plan from their predecessor and decides to implement something new. So all the work that’s been done on this by the engineering team maybe has to be got rid of and so it was just meaningless, which creates a lot of problems with burnout, I think, for developers as well when it’s like, suddenly I’ve got a new.
Jason Lengstorf (35:29)
Yeah.
Mm-hmm.
Kate Holterhoff (35:36)
boss here and they don’t like this, they feel like they’re not gonna get a bonus if this is their predecessor’s ideas. Yeah, it’s easy to get real cynical talking about this. I’m interested, you said it was that the executives get nervous and that’s why they changed the plan. Are you able to put any pressure on that idea? Like what does nervous look like and is it always nerves?
Jason Lengstorf (35:57)
I mean, I don’t know if it’s always nerves, but what I observed is that we have a group of people whose core skill is not backing down from a challenge. And that requires a certain type of like idea-based, you’re always kind of throwing things at the wall, you’re willing to wade into an unknown conversation and
and make a decision. But the challenge is that there’s a difference between having the confidence to like take on an uncomfortable conversation and having the courage to like own that decision. And where I see the nerves come in is that if, you know, if we’re talking and you say, I don’t know how we’re gonna solve this problem. And I say, all right, tell me what you know. And then we talk about like, all right, all right, well, what if you tried it like this?
And then I come up with solution, right? Well, great, that’s why they made me a VP. Now if I don’t let you go and do that, and instead, the next time I have a conversation, I go, ooh, I got a new idea. And then I call you and I say, forget what I said yesterday, I got a new idea, right? Now you are starting to fear any time that I show up in your DMs, right? And I didn’t do it because I’m a bad person, or because I’m unorganized, or because I hate my team, or because I wanna fail. I do it because I wanna succeed.
And because the skill set that I have refined the most is my ability to like ideate and make decisions. So my nerves as a leader are if I’m not ideating and making decisions, I’m not doing the thing they hired me for. And so to say we already made that decision, everybody sit tight, let’s let the team cook. That feels like an abdication of duty, which then makes you feel like you’re gonna get replaced because you’re not delivering, right?
And so that’s what I’ve seen is that the execs will get really antsy when a plan is in action because they’re like, well, but now I’m not doing anything. They start making new plans and new plans and new plans because plans are what executives are supposed to do. So the challenge, I think, is figuring out what are the phases of being an executive. And so for me, I would try to break it into sort of like three pieces. was making a plan.
Right, that was really fun. I got the team together. We did these big whiteboarding sessions. We would come up with our big plans for the year, all the ways we were gonna take over the world. And then the second phase was protection. And my entire job became, I turned my back to the team and I said, you holler if you need me. But then I was just like, all right, executive, stay away. Like, and I spent a lot of my time gently chastising my coworkers and saying, do not get into my team’s DMs. If you have an idea, it comes through me.
And then they would come to me and they would say, want to change this. I would say, no, you don’t. Right. And my whole job was to say, listen, I will do that after this, but you need to provide a very ironclad business justification for ripping up all of their last month’s worth of work before I’m going to go and whip the plan around. And typically, if you start saying like, why is this more important than that? The argument starts to fall apart. And a lot of it just becomes like, well, I just felt like I needed to change something. Right. And if that’s the answer.
Kate Holterhoff (38:38)
Hehehehe
Jason Lengstorf (39:03)
great, I’m not gonna do it. That’s like no hard feelings, we can do it later, but it doesn’t supersede what we’ve already planned, right? Then, after you get the plan, the third thing is to then turn around and measure it and share, right? And so your job as the executive is to be a megaphone for the people on your team who did good work to understand where the strengths and the opportunities were in the work that was done.
And then to kind of set the boundaries for the next phase of planning so that you can repeat that cycle over and over again. And it doesn’t have to be a long cycle. It can be quarterly, right? And every company can afford a quarter of focus. And in fact, every company would probably be running 10 times faster if they consistently focused for one quarter at a time instead of ripping up the roadmap every other week. but it’s hard. mean, even when I, I’ve made that as my explicit focus, like that was my goal. would write it on my sticky notes and like,
put it on my laptop, like don’t make any new decisions today, just protect people. And even then it was so hard because people would come in and they would start, you get new information, the board comes with some new report, you hear a press release from one of your competitors and your instinct is immediately go, we can counter that, here’s how we’re gonna do it. And then you’re like trying to pull resources off of something and it’s like, my God, what am I doing? I’m doing the thing, I gotta stop doing the thing, we have a good plan. And because I’m nervous that this PR came out.
doesn’t change the fact that this plan is still a good plan, we should do this plan. But yeah, it’s a hard job.
Kate Holterhoff (40:31)
Yeah, I can tell. I love that you foregrounded protecting your team because I think all the best leadership that I’ve interacted with in my time has done that. That’s been their primary goal. Like, how am I going to make sure that my team is able to work successfully, happily, in a way that’s going to benefit the organization as a whole? And I’m curious, so were you always within the engineering team then or were you ever in product?
Jason Lengstorf (40:49)
Yes.
like when I was at Gatsby, there wasn’t such thing as like engineering and product and marketing. was just one team, right? And so I sort of sat across a lot of it. at Netlify there toward the end, my, had this, this wonderful counterpart in Lauren Sell, who was the VP of marketing at Netlify and she ended up getting a different job. And when she left, we didn’t have a, like an immediate recovery plan.
So I ended up being the VP of marketing in an acting capacity for a while against everyone’s better judgment. was like, they were like, you can handle this, right? And I was like, absolutely not. And they were like, you’ll be fine. And so, you know, I worked heavily with product, but never in the product org.
Kate Holterhoff (41:37)
OK, and the reason I ask is because a lot of this sort of behavior that I have encountered from other folks that I speak with has been the product team having ideas that they want engineering to then build. And that sort of enthusiasm for new features that may or may not be called for by the customer or that just seem kind of cool and like, now it’s AI, right? I tend to hear it.
positioned as like product versus engineering. And I don’t know that it necessarily has to be a versus situation. It sounds like it wasn’t in your experience. I don’t know. Have you heard it framed that way?
Jason Lengstorf (42:11)
My experience has been that every org is its own worst enemy. So what I noticed was I would watch engineering, or actually, I mean, let’s start with product because product was guilty of this too. Product would, they would run off and they would try to create something and every product manager was on the hook to deliver a feature, right? And so they would,
Kate Holterhoff (42:15)
You
Jason Lengstorf (42:33)
hopefully be talking to the user research team and they would be coming back with something that had some data, but not always. But then they wanted to prioritize it and we had something like 15 product managers at Netlify and at IBM they were called product owners, they, God, there were dozens of them. And every one of them basically felt their promotions rode on them delivering features. So.
There was a huge push from the product team to say, like, I have the right idea, we should prioritize my thing, this is the thing that we should work on. At the same time, the engineering team was, I just learned about this new tech that would revolutionize everything. I just had this idea for how we could rewrite our caching layer and improve this thing. Or, just realized that we could build this thing that’s sort of like the competitor’s thing, but it’s better in this way. And so they’re internally farming new features.
that then they want to ship. Sales is doing what sales does and they need something to sell, right? And so they’re always pushing for something new because new things allow them to make new phone calls and try to get new leads or rekindle old conversations with a new offer. Marketing needs something to launch, right? And the thing that I always struggled with is, you know, we have such short memories at companies and we built a good product.
Like, especially if your company is revenue, like if you have growing revenue, people are paying for your thing. What are they paying for? You don’t need a new thing to get people to pay you. They’re paying for what you have now. So what is it? How can you talk about that in sales? How can you talk about it in marketing? How can you improve it in product? How can you, you know, it doesn’t need to be net new. And I think that we are very bad at this in tech startups where we think that the only value that can be added is new things.
And we don’t want to do the work of like, we’ve got a pile of user research that says, our navigation is hard. We should do a, like, go fix the navigation in our app. Nobody wants to do that. That’s not fun. That’s not innovative. We don’t get to write a cool blog post about all the cool stuff we did for that. We just did a thing that made our users’ life better and now they want to pay us more. Right? And the same thing is true across all sorts of areas of these apps. Like there was a project that we did at Netlify where we just
We’d been slowly complaining about the fact that our docs, our marketing site and our app looked like three completely different companies because they were built at different times with different design systems and they had, you know, the fonts didn’t match up, the colors didn’t quite match up and everybody complained about it, but we would never prioritize it because it wasn’t a new feature. It wasn’t a new thing. Right. And I remember we, we finally prioritize it. I put together this big cross-functional thing. we call it web cohesion week.
And I was like, give me like five people from each of these teams. Let’s put them in, it was Lauren’s house in Austin, Texas, and five days, like give me these people for five days. We’re going to solve this problem. And it ended up being one of the best things that we’d ever done for morale. The customers were talking about it. The product felt better, which meant people were more excited to work on it. People were sharing screenshots. It was this, this huge, like little lift that made a huge difference. And
Those are the sorts of things that actually make products better. Like shoving AI in a place that we had no business shoving AI doesn’t make a product better. It’s a boondoggle that makes you think you shipped a new feature. What actually makes the product better is looking through the user research and realizing that literally everybody who talks about your product says, just wish they would do X and then doing X even if it’s super boring and is like tech deck cleanup. But we don’t have the.
We generally lack the ability to like buckle down and do boring work. We only want to do new and shiny because new and shiny is what gets noticed and promoted and talked about in the magazines.
Kate Holterhoff (46:17)
I love that you’re hitting this very appropriate note of cynicism that I like to cultivate on the show, so thank you for that.
Jason Lengstorf (46:20)
Ha ha ha ha ha ha ha ha ha ha
ha
Kate Holterhoff (46:23)
So we’ve alluded to the through line of creating content that has existed from the beginning. so I’m excited to talk about your newest venture and how all of the lessons that you’ve been learning along the way and all the connections that you’ve made have led you to your newest
company and so talk to me about what you’re doing today and how it’s building on all the wonderful things you’ve done so far.
Jason Lengstorf (46:48)
Yeah, so I got my start in performance. was the lead singer of a band. I was doing shows every night. I really loved that. I liked the kind of connection that you get with somebody when you do that kind of performance. And I’d been missing that for a long time. And that was what got me back into the community work. I saw this opportunity. It was a great way to connect with people again and do stuff that wasn’t just technical. was both, right?
And so when I was at Netlify, the same thing, I saw these opportunities. We could do video, we could do more interesting stuff that helps us connect with people. We can tell our stories in a way that’s actually fun to watch instead of trying to guilt people into watching a webinar by putting a white paper behind an email sign up or whatever it is. We can do these things that would actually get people to engage by choice, not by clever marketing design. And so I got a taste of this at Netlify where I got to do a handful of these projects.
I left because I couldn’t get them on board with my full vision. And that’s fair because it was a completely unreasonable vision. I was trying to put together like multi-million dollar marketing budgets to go and do full media productions of all sorts of interesting stuff. And I hold to it that it actually would have been far better than what they did and would have gotten better results. But doing it independently I think ended up being the right call because it forced me to think small.
So what I started out by doing was the standard thing that a lot of folks do when they go independent as content creators. was working with companies, making tutorials, doing the stuff that you see on a lot of YouTube channels, and I was immediately thinking, like, this isn’t sustainable. I’m not gonna be able to do this forever. I don’t like that kind of work. This isn’t what I signed up for. So I started looking at, nobody’s gonna give me a half million dollars to go make a TV series. I have to prove that I can make a TV series.
before anybody would ever consider that.
Kate Holterhoff (48:38)
It sounds like there is some banging going on in the background. just, you know, want to point that out.
Jason Lengstorf (48:43)
Yeah, we’re actually doing construction on the set for Web Dev Challenge as we speak, so we’re putting together some new, like, a big display and some custom walls, and I’m really excited to show that, actually. It’s gonna be a whole thing. There we go.
Kate Holterhoff (48:58)
Get out, that’s great. So I love that your TV show is like part of this episode of the podcast then. It’s like we’re drawing it all together. We’re bringing it in. All right, fair enough.
Jason Lengstorf (49:03)
Hahaha!
And so I started looking at how do I scale this down and I did a remote version of a show that was 4 web devs build the same app idea. So I gave some friends of mine a prompt, they built a demo and they recorded themselves doing a demo of it and then we all like recorded ourselves kind of going through it and talking about what we liked. It was a really simple format but I’d seen it done in photography. There’s a woman named Jessica Kobeissi who had done
like four photographers shoot the same model. And then a guy named Andrew Huang in music production did four producers flip the same sample where he gives like a specific constraint to a group of producers. They go make a song and then they all like, you know, show off what they did and then listen to each other’s music and react to it. So I knew that the format worked and I wanted to try it. So I tried it, it worked really well. And I was like, okay, but I want more. I want to do this in person. So I worked with companies and I got
DataStax whose DataStax is great because they have basically been down to fund all of my wild ideas with no proof. I have like, Lauren Goll and Carter Rabasa over there, I’m like, hey, I have this wild idea and they’re like, how much is it? And I’ll tell them and they’re like, yeah, all right, let’s do one. And they’re just down. So they funded the first web dev challenge, which is like great British bake off, but for web devs.
where we fly people out to Portland, they build apps together, we film it in a reality TV show style, we’ve got a full film production crew, we have them demo in person and all this. it’s been just a runaway hit. The series, I think, has crossed a million collective views and it’s had wild success from partnerships ranging from tech companies that wanna get involved to BenQ monitors.
Now an official sponsor of the show because the devs that are working are using BenQ monitors and you know It’s good for them to see professional devs using their stuff and I actually really like those monitors So it was like a huge win for me because I got to upgrade the setup And like, you know, and and so it’s these these this really kind of natural It’s a very natural way to get developers to try a thing and so in like DataStax the first episode They wanted people to know that they offer a vector database
Kate Holterhoff (51:03)
Ha!
Jason Lengstorf (51:17)
I was like, great, let’s build an AI app that is not a chat bot. And they were like, that’s brilliant. So we just, that was the entire prompt. It was like, all right, devs, you’ve got four hours, build something that’s not a chat bot that uses AI. And everybody just kind of went off and did their thing. And so everybody used the vector database thing and we get to see them put it together. There’s open source code. It’s like, it’s basically a webinar, right? It’s four different developers using this tool.
and then showing how they use this tool. And you choose to watch it because it’s way more fun than like a canned use case demo. It’s actually interesting. You get to see them struggle and get it wrong and then undo their work and start a different path. And you get to see them talk to each other about what they’re working on. And you see somebody else get inspired because this dev had this idea and they go, that’s brilliant. I should do something like that. And they start kind of like building off of each other. And it’s fun to watch, right?
And so that kind of proved the model and allowed me to do, I did 10 episodes in season one and I’m currently booking season two, which is probably gonna be 12 episodes and I’m gonna move to teams of devs this time. teams of two devs instead of individual devs. Just so that we get a little more collaboration and seeing people work. And I also was able to put together a game show. It’s kind of like Wheel of Fortune and Jeopardy and Hot Ones is like a web dev trivia show.
You get answers wrong, you gotta eat spicy bites. But all of these shows are kind of built off of formats that we know work. We all watch Jeopardy, we watch Wheel of Fortune, we watch Hot Ones. So why not make something like that tailored to web development audiences in a way that lets a company build community affinity? As a great example, Deno is brilliant because I started putting together Leet Heat, the game show, and I said, hey, we’re feeding
the contestants, their spicy bites on chicken nuggets, right? We got like, I thought it would be funny to get dinosaur nuggets because it was an easy thing to eat and it’s kind of funny. And then while we were doing a test play, somebody said, you you should talk to Deno about this. And I was like, that’s genius. So I emailed Deno and they immediately were like, yes, we’re the official chicken nugget sponsor of Leet Heat, right? And it’s the most, first of all, my favorite contract I’ve ever written in my entire life is like official chicken nugget sponsor.
But also the, you the outcome is that now you’ve got this company being silly and talking about what they do, but in a very kind of one of us way, like the way that devs sitting around a dinner table would make jokes about the companies and tools that we use. They’re part of that conversation in a way that makes us feel like these are humans. We want to be friends with them. I want to hang out with the Deno team, right? And that makes me feel more likely to
reach for them in a project in the future than I would if they had done some cold corporate like standard webinar. And I think we tend to underestimate how much just being a person lends to the value of an exchange. And this TV format, I truly believe is how companies can just be people. Like send your team to me.
Let’s make something silly together. Let them be themselves. And then when the rest of the community sees them being themselves, they will say, I kind of like their style. want to see more about what they’re about, right? And it’s never about the tech. The tech is always so similar that you’re kind of fighting on like specific features, like number of gigabits or number of milliseconds. It doesn’t matter. What matters is that you want to be aligned with a company that feels like your kind of company. And you learn that by who they are, right?
And so to me, that’s sort of the next frontier here. That’s what we were doing with events before. You would go to an event to meet the people that worked at these companies. You would get good vibes. You’d go through the vendor hall and you’d have a really good conversation at a booth and you’d go, you know, I like them. I want to use that. Right? It wasn’t about the swag that you got. It was just the people. It’s always people. And so how can we scale people? You put them on video instead of in person. You can meet more people that way.
Kate Holterhoff (55:19)
Okay, well, so I’m really interested in your thoughts on, yeah, getting developers excited about, not only products, but these technologies. And so I’ve been really inspired by like Adam DuVander’s writing. And he talks about the way to reach
developers as having a lot to do with education. So instead of marketing to them, you educate them. And I feel like a lot of the content that I’ve seen you produce really gets to the heart of that. so when I’ve watched some of your video series where you have on folks like Laurie Voss, Chris Coyier, it reminds me of those recipe sites where you begin by just having a conversation and explaining how your day is going. And then it’s of the recipes in there.
you know, towards the end, and then, you know, there’s some jokes and you get to, you feel all warm and fuzzy. I love that format. And I feel like your TV show is sort of an extension of that where you’re, you know, showing the human side, but education still seems to be a really important part of this. What is your, how do you approach that?
Jason Lengstorf (56:17)
Yeah!
So I have, this is a philosophical rabbit hole. basically where I’m at is I a big belief in education, but not education in the typical pedagogical, I am the teacher, you are the student. I think more about
where I learned the biggest lessons in my career and it was almost always through sitting next to somebody and watching how they solved a problem and learning a little tip or a little trick or I would see the way that they would work through a problem or get themselves unstuck and I would say, hold on, what was that? What did you just do? And that type of, I heard it called tacit knowledge exchange and I really find that to be
one of the most important parts of how a developer levels up. And I think that’s why in other trades you have like the apprenticeship and like journeyman and that sort of thing is because you need to sort of watch somebody with more experience for a while to start picking up their traits and their like unconscious habits and the little things that they just know that they could never explain. You just have, you kind of have to see it, like observe it and go, why?
And then they’ll explain why they did it. Because when you watch somebody give a demo, the demo is rehearsed. They worked through it, they got through all the bugs already, they’ve got an end result they’re working toward, and they’re gonna show you the happy path. What they’re not gonna show you is when they forget what the name of the config item is and they start getting an error, how do they turn that error in their brain into the knowledge that they need to go back to that config? Sometimes that’s really easy because the system has a good error messaging system, and sometimes it’s really not. And you just kinda have to know.
And the first time you hit that error, you Google it and then you go on Stack Overflow and then maybe you get into the forum for the open source project and you say, I just got this error, what does this mean? And then somebody who knows will tell you. But if you’re watching somebody work, you get to see all that happen in a heartbeat. Right? And so one of the things I love about these shows is we have these moments where developers talk about their experience or they’re actively doing something. And in both cases, you get these unconscious moments of tacit knowledge exchange where I’ll talk about, know, I’ve been
writing code for over 20 years at this point. And so there’s a lot of stuff that I just forgot that I learned. know, it’s like playing music, you know, if you’ve been playing music for a really long time, you’re not looking at the piano going like, that’s this note and that’s this note and that’s this chord exactly. You’re just playing because it’s sort of like language, right? Like I’m not thinking about the English language when I’m speaking to you right now. I’m just speaking English because I’m so confident in my ability to speak English that I’m basically using it as an unconscious translation from my thoughts.
And I think that we do that with code a lot. We do that with any skill once we get sufficiently good at it. So there needs to be a moment where somebody can interrupt you and say, why did you do it like that? Why did you make that choice? And then we can explain our reasoning, but we would never, I would never sit down and say, okay, list of topics to teach people and come up with those things. They just won’t. They’d never even occur to me to teach. And so, so I’m really into this idea of trying to expose
Actual development. That’s why the premise of learn with Jason my live stream is 90 minutes that I do not prepare for I don’t even know how the tools work when I start that live stream I intentionally come in with no idea what’s going on because I want to struggle I want to ask the beginner questions I want to get it wrong and then have them explain what I did wrong because that I think is what makes it possible for somebody who’s watching to say I can figure this out You know they and then when they start
and they hit those bugs, go, I saw Jason hit this. They can go back to the video and they can watch that part and they go, yeah, that’s how he solved it, right? Those little things are, it’s just so hard to figure out how to turn that into a curriculum. It sort of has to happen naturally.
Kate Holterhoff (59:59)
Yeah.
I love that idea. It does seem to run counter to the way that I typically learn online. If I’m trying to learn a particular technology, go on YouTube and I say, hey, I wanna accomplish this task or I wanna learn this particular stack or whatever. And then I want the shortest version possible, right? So talk to me about who is watching these videos then, because I feel like I, in my haste, wouldn’t look to your video immediately.
Jason Lengstorf (1:00:25)
Yes.
Kate Holterhoff (1:00:34)
However, if I was vibing, you’d be the one that I would like have a glass of wine and, hang out with my friends. So talk to me about who’s watching this. I guess that would extend to your TV show as well.
Jason Lengstorf (1:00:35)
No.
So I think of it as the way that I, in becoming a better writer, you can read the dictionary and the thesaurus, and you will. They’re tools when you have a problem. I’m trying to come up with this word, let me look it up, right? You know the problem is well-defined, you know exactly what to do. Most of the time in writing though, it’s not about which word to use or the specific thing you’re trying to say, it’s about how do we say this in a way that is going to connect, that’s gonna land, that’s gonna paint a picture that people truly understand?
And that’s not something you can Google for. It has to be something that you pick up. And so to do that, you read. You read fiction, you read nonfiction, you read articles, you read clever writers on social media. And all of that is sort of like slow training on being a better writer. If you’re observing it from the standpoint of like what makes writing good. And I think of it the same way. Like if you are trying to figure out what an error message means, you won’t go to my show and you shouldn’t. It would be a silly thing to do. It would be kind of a
distraction from what you’re trying to accomplish. But if you are interested in like how do really skilled programmers do the things that I do, like what makes somebody a senior versus an entry level dev, then you can watch this in the same way that you would read fiction or that you would, you know, you would read somebody else’s writing if you’re trying to become a better writer. It’s not active study. It’s observation of people who have done something that you want to do. And, and you sort of
passively are consuming the content, but there are moments where you’ll say, what was that? Like, I do this with cooking shows all the time. If I wanna learn a recipe, I go to the recipe and I hit the print button so that it just shows me the recipe. But a lot of times, instead, I will go watch somebody like J. Kenji López-Alt make something that I’ve made a thousand times before, not because I need him to show me how to make that recipe, but because I wanna see the little techniques that show up, like.
when he uses a chopstick instead of a spatula to stir scrambled eggs, why? And he’s got reasoning and he’ll explain it, but he would never make an article on why to use chopsticks instead of a spatula to stir scrambled eggs. And so that’s kind how I think about it, is it’s the little skill thing. it’s sort of a, I would say the stuff that you can’t find tutorials for that only emerges in natural conversation or natural observation.
That’s the content that I always want. That’s what I watch. I want to see cooks cooking because that will make me a better cook. I want to read great writers because that’ll make me a better writer. And I want to watch great developers because that’ll make me a better developer. I think it’s the sort of that cliche of you become the sum of the five people you spend the most time with. I think that the same is true of like, if you consume content of people who are doing something that you want to be great at, you’re going to absorb the things that
they’re great at and that will become part of what you’re great at as long as you are pairing that with active practice.
Kate Holterhoff (1:03:36)
Yes, that is extremely inspiring. you’ve shifted the way that I’m thinking about this. I very much appreciate how you’re framing it. I like the idea of it being like a conscious decision. I know we’re getting to time here, but it also is reminding me of when I speak to folks about what is the role of the developer profession going to be in our age of AI.
where a lot of junior development level, skill sets are being offloaded to AI code assistants at this point. And so whether or not you’re a doomer in terms of the amount of code that’s gonna be written by AI or just have it sort of in the background, I think there is something to be said for.
Jason Lengstorf (1:04:06)
Hmm.
Kate Holterhoff (1:04:18)
up-skilling and leveling up our abilities. And so I think that if you’re catering to the developers who are looking to become exceptional, that is a niche that is really only gonna become more important to fill.
Jason Lengstorf (1:04:27)
Mm-hmm.
Yeah, exactly, and I also think in the age of AI, it shifts the work, it doesn’t remove the work, right? And the thing that I’ve always noticed is that what makes things valuable isn’t the yes or no ability to solve a problem, because if that was the case, then we would all do literally everything on Fiverr because it’s a dollar to get somebody to do a job, right? But clearly, there are a lot of factors other than price and strictly complete.
that make us make choices about what is, what we should spend time and money and effort on. And AI is the same thing. AI can spit out a very similar looking thing every time you ask for it. If you want anything beyond that, you’re still gonna need somebody who can be creative, who can turn it into something else, who can add a feature that hasn’t been invented before that AI can’t pull from its data source to predict. Like,
There’s always room for humans. And I think the thing that’s really important is recognizing that no matter what the skill is, if our intention is to continuously be learning and upskilling, then it kind of doesn’t matter if the framework goes away or if we all shift from JavaScript to writing prompts or if we all, you know, if AI completely dries up and something new comes up in the future. All of those things are still gonna be
pulling on these skills of being able to understand and interpret and deliver something that is unique and interesting and connects with humans. And if we can make sure that we’re always just learning and curious and interested, then we’ll always have a valuable skill set regardless of what the tools are that are being used to create it.
Kate Holterhoff (1:06:08)
I love that. And I know that you and I could keep talking for another two hours. I’m gonna have to have you come back on the MonkCast so that we can hit all the other bullet points that were in my notes here. But before we do go, can you explain how folks should be following you online? What are your preferred social channels these days? Are you doing any speaking in 2025? How should folks be keeping up?
Jason Lengstorf (1:06:32)
I am doing some speaking. I’ll be at CityJS London. I think that’s in April. I’ll be at, I believe, at the Lead Dev in New York. I don’t remember when that is. Probably end up in a few, Render ATL in, I believe that’s in June. That one’s great. And then I am on Bluesky. My handle is @jason.energy, which is also my website for my personal stuff.
And then if you want to look at the other stuff I’m doing, it’s Codetv.dev.
Kate Holterhoff (1:07:00)
Wonderful. And I will see you at Render ATL. You know, I’m in Atlanta, so I never miss that one. I’ve really enjoyed speaking with you, Jason. 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 are watching us on RedMonk’s YouTube channel, please like, subscribe, and engage with us in the comments.
Jason Lengstorf (1:07:05)
Alright.
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