Joshua Jenkins: Design, Startups, Leadership, and More! ⚡️
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by kirupa | Interviews with Creative People: https://www.kirupa.com/podcast/index.htm

Joshua Jenkins (https://joshuajenkins.com/) shares a career shaped by making, not posturing: tiny AIM icons, improvised internal tools, startup swings, and eventually design leadership at scale. The throughline is practical judgment. He cares about tools that remove friction, teams that make decisions close to the work, and growth that comes from doing the next useful thing well.

Watch the interview: https://www.youtube.com/watch?v=Hr0omR9fV50
A conversation with Joshua Jenkins | 1h 06m

ABOUT THIS CONVERSATION

Joshua Jenkins has one of those career stories that feels recognizable the moment he starts telling it. He did not begin with a tidy plan to become a design leader. He began by making tiny animated AIM icons, taking on odd jobs, and gradually discovering that improving the thing in front of him was both fun and strangely revealing. That instinct carried into a job at HP, where he built rough internal tools for himself, and later into agency work, where he became the kind of person who could bridge design intent and implementation reality. That bridge role is a real theme here: he respects craft on both sides and has spent years translating between them.

The middle of the conversation turns toward AI and startups, but the tone stays grounded. Joshua is interested in AI when it helps turn a fuzzy problem into a workable starting point, not when it promises magic. That same practicality shows up in the startup discussion. He talks about building around a question people actually want answered, rather than around a trend that only looks good from a distance. It is a useful reminder that good product instincts often sound simple because they are tied to concrete user needs. The glamour drops away and what remains is the work of choosing the right problem, shaping it clearly, and staying close to reality while you build.

The back half is especially strong on management. Joshua describes the shift from individual contributor to design manager during his time at Snowflake, and he is refreshingly clear that the job changes in kind, not just in scope. Design teams need structure, but they do not benefit from borrowing engineering playbooks wholesale. Leaders have to understand how design work moves, where judgment lives, and when to shield teams from noise. He also makes a smart point about learning from both good and bad environments. Strong managers give you models to follow. Weak ones teach anti-patterns you never want to repeat. Together, those lessons form a thoughtful picture of leadership rooted in taste, trust, and operational clarity.

WHAT YOU'LL HEAR ABOUT

- Creative constraints can build lasting design instincts.
- Bridge roles between design and code can become a real specialty.
- AI is most useful when it helps shape a fuzzy problem into a workable start.
- Startup ideas get sharper when they answer a concrete user question.
- Great design leadership pushes decisions closer to the people doing the work.

JUMP TO A TOPIC

- 0:00 - A maker origin story: Joshua opens with AIM icons, early internet making, and the constraints that first shaped his design instincts. (https://www.youtube.com/watch?v=Hr0omR9fV50&t=0s)
- 9:00 - Learning by improving things: He reflects on side projects, pattern recognition, and why useful work often teaches more than perfect planning. (https://www.youtube.com/watch?v=Hr0omR9fV50&t=540s)
- 13:00 - Where AI actually helps: The conversation gets practical about using AI to narrow ambiguity and speed up problem solving. (https://www.youtube.com/watch?v=Hr0omR9fV50&t=780s)
- 26:00 - Starting with a real question: Joshua explains the startup thinking behind building around a clear consumer need instead of a trend. (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1560s)
- 39:00 - From founder to manager: He talks about joining Snowflake and making the jump from hands-on work to design leadership. (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2340s)
- 44:00 - Design teams need their own logic: Joshua describes building a design organization and why it cannot simply mirror engineering structures. (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2640s)
- 47:00 - Leadership speed and protection: This section covers decision-making, team protection, and how healthy organizations keep work moving. (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2820s)
- 53:00 - Learning from great managers: He makes the case that aspiring leaders benefit enormously from working under strong managers first. (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3180s)
- 58:00 - Career anti-lessons: Joshua closes on maturity, anti-patterns, and the value of learning from less effective environments too. (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3480s)

TO LEARN MORE

- Joshua's Website: https://joshuajenkins.com/
- Joshua's X / Twitter: https://twitter.com/joshuajenkins

TRANSCRIPT

The automatically generated captions have been organized by speaker, lightly edited for clarity, and broken into paragraphs for readability. Names and wording may still contain errors.

0:00 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=0s)

Hi, everybody. In this chat, I am thrilled to talk with Joshua Jenkins, someone I have known for over 20 years, both online and offline. He is a talented designer, developer, entrepreneur, and design leader. We talk about everything from how he got started to the cool things happening with AI and design. We also spend a lot of time discussing what it is like to be a manager, transition from being an individual contributor to a manager, and discover many things along the way. I hope you enjoy it. Josh, it is great to finally meet like this, even though I think we met in person around 2006. Does that sound right?

It has been a while. I think it was on the University of Washington campus. You were there, and I was interning at the time. We met there, and of course we have known each other online for ages at this point. You have been sharing cool things forever, and I have always felt that you wear many hats effectively: designer, developer, design leader, startup entrepreneur, and more. I think we will touch on all of those things as we go. I would like to start with the question I typically ask: What is the first thing you remember building?

1:13 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=73s)

Okay, that's an interesting question, and I'll start by saying thanks for having me here. It's great to be here. The first thing I remember building was back in the AOL Instant Messenger days, which was a long time ago. People listening now probably have no idea what that even was, but this was probably around 2000, 2000, I don't know, something like that. I was basically making animated GIFs for those little avatars and icons—your AIM icon. That was the first thing I really remember making: frame by frame, pixel by pixel.

They were tiny, like 16 by 16 or 32 by 32, super constrained, and I'd make these goofy little animated faces and things like that. I was probably around 13 or so.

2:01 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=121s)

Wow. And what tool were you using to make those?

2:03 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=123s)

To make those? It was actually before Photoshop, because I couldn't afford Photoshop. I don't even remember exactly what it was. It might have been something more obscure and weird.

2:19 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=139s)

Yeah, those were fun days, because back then 16 by 16 was actually a massive amount of real estate to work with. Nowadays it's almost invisible. Back then most screens were like 40 by 480 or 800 by 600 if you were lucky, maybe 1024 by 768, so 16 by 16 felt huge.

2:35 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=155s)

Yeah, it's crazy how different it is now.

2:37 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=157s)

The other funny thing is that with higher-DPI screens now, all those old 16-by-16 pixel assets from 20 years ago just look awful today. It's hard to bring that world forward faithfully.

2:50 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=170s)

Yeah, I mean, I think there's like two, like there's people that like kind of try to Faithfully scale things up in like the grid right and keep the crisp lines. And then there's all this stuff now where people are like feeding it into like you know, AI and generative stuff and right, and then it's like you know, blows up a 16x16 thing into like a, like a physical Avatar. It's crazy, yeah.

3:08 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=188s)

Yeah, and the next complication is like: okay, you figured all that out, you got it perfectly sized. They need to share it somewhere. And you know where do you go? You go to like Twitter or Instagram or so on, and they happen to scale it and compress in their own way up and you're like: great, you know, I spent all this time doing this, I know, and now I can do it anymore.

3:24 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=204s)

Yeah, I think there's like a generation of people that work on screens and probably feel this pain all the time, or it's like. You know, I think a lot of us spent so much time with like pixel precision and like just getting things to like be precise, and then all of this, yeah, million screens and different networks and all this stuff, and it's just like this constant losing battle. But until they get to like, I think like maybe like another 2x on like retina, you can still kind of tell you know, so we're not quite out of the woodwork, we're like you can just do whatever.

3:50 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=230s)

Yeah, like, I guess like the 8K screens might be the ones that can ultimately do this for you, because the funny thing is that Vimeo came out a long time ago and they were all about like, we're not going to compress your videos as much, we'll give you really high quality videos, and so a lot of like designers and people cared about high quality visuals, end up uploading to Vimeo and it's actually really cool. But the downside was the whole network effects and everyone just kept going to YouTube because it just it was YouTube.

You know everything was there, you know from like high quality, you know animation stuff, but also like music videos and you know Cat videos, all that stuff. Right, yeah, and this is like the market, for it just seems to keep going to an interaction that doesn't really help us too much. Yeah, I totally.

4:26 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=266s)

Agreed. They're mass-media platforms, and the formats they support end up dictating the form.

4:32 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=272s)

So that's the first thing you remember designing, and then you eventually became a designer in a much more full-time sense, both personally and professionally. How did that transition happen?

4:47 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=287s)

It's an interesting question. I managed to get a couple of odd jobs when I was in like high school, like, getting paid hourly to, you know, skin, a site or something like that. Right, I think that would probably like be first kind of dip into like professional, but it was very, like you know, I had no training. I didn't know what that world looked like. I was just doing like stuff, right, and then I took a detour through like college and like early jobs.

Was very far from this stuff, but, I worked at HP of all places, in I don't know two thousand, I don't know three, let's call it- and I had this kind of random job where, basically, like I went around to like different offices and I like found where people's printers were and I like put them on a map and I was like, okay, like you have this type of printer and then, like, put it on a map and I plot this thing all out and you do little interviews with people, how much you print, what kind of stuff you need to do whatever, and the tools we use are like super cumbersome and then, like.

I made some random like HTML, PHP, like totally crappy thing, but like something that helped me do that a little bit. And then I would like spend my time like making that thing nicer and I was like I really like making this thing nicer- and I didn't know it at the time, but I'm effectively doing like UX design or like product design for a customer of one which is me, and like this was not sanctioned in any way. Right, this is like not like this was not like hey go, we like you doing this, keep doing this,.

But I realized I like doing that and, then I started to kind of look out there and see like what other kinds of ways to actually kind of apply that thing would be- again, having no idea what the industry looks like, having no idea about anything, and eventually found my way into agencies, I guess in Portland, Oregon. So, I was working at a, some smaller and some larger agencies, basically doing like web work or like random creative work, right,. But even that was super interesting because, like, I've always come at things kind of from a weird sideways way.

So I'm this kind of I kind of got hired as kind of the digital guy. You know. They kind of just like sort of Jack of all trades and just kind of do stuff, knows enough about design, knows enough about coding, can kind of bridge the gap. Like I'm working with, like you know, like legit graphic designers right, who are like color theory and typography and like grids and all this kind of stuff and, like you know, you think you understand this stuff and then you see people who like live and breathe it and you're like oh wow, no, there's like a whole deep Universe here.

I don't understand at all. But yeah, so I ended up at agencies like that and, you know, super cool to get to like kind of be around these other skill sets and kind of grow from there and there's a bunch more hops after that. But that's kind of how I, how that's how I formally got into like design, like into agencies.

7:24 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=444s)

Do you think your formal education helped as you started doing more business-oriented work, or was it more that you were experimenting, trying things, and learning that way?

7:33 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=453s)

Yeah, I'm not exactly a formal-education success story. I dropped out of, I think, four or five colleges. The cool thing to do is drop out of Harvard; I dropped out of community college, which maybe is even cooler. Formal education exposed me to some ideas, but I wouldn't say I learned useful web-design skills in college.

8:04 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=484s)

It definitely seems like you were passionately interested in this, though. Even if formal education wasn't really your style, you still knew you wanted to be in the industry, and you worked hard to learn those skills in other ways.

8:20 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=500s)

It's fair, I think, there's always been like a genuine to sort of curiosity and interest, and I think that's what's Driven, that's been that through line, through everything right. It's always been like what's the next interesting thing, like what do I want to learn? That kind of stuff. So, yeah, the, sort of wanting to figure it out part has been very helpful. Yeah, you know, you can see.

8:37 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=517s)

That in so many examples of people who end up being you know, who just enjoy what they do, is oftentimes just like curiosity in that drive and almost that grind itself. Sometimes, you know, I think too many people spend way too much effort trying to optimize for like the ideal environment to build something in a scalable way. I'm like you know, just start, just start and just do it. You know it might take you hours upon hours, but getting it done and the things you learn indirectly through that probably far more valuable than kind of the perfect solution at the very beginning.

Strong, strongly agree, strongly, co-sign, yeah, and I think more often now, you know, because I've never. I'm not a designer, nor am I a developer, I'm a product manager, but I get to work with all these disciplines on a regular basis and often in the back of my mind I can see that pattern coming through all the time and I've seen people like, wow, at first you know they understand what's going on. I dig a Little Deeper.

It's always the case where they just spent like I don't know, it's like 10 000 hours thing, but Gladwell is truly a number, but it's an idea that they spend a lot of time doing something that only they sell the real value in it, but it ended up paying dividends for them eventually.

9:36 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=576s)

Yeah, I agree. If you can find your own path, that's probably going to work better than just following a prescribed one, because your curiosity and motivation will carry you through it.

9:51 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=591s)

I also feel like you're not only a designer, but that you have a pretty strong understanding of programming too. How did that come about?

9:56 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=596s)

About I would. I definitely do not have a strong understanding of programming. I have a sort of begrudging, like I need to program to realize things I want to do, but the degree to which I'm bad at programming I like cannot overstate. If I, if I'm working on something actively for like a week, I can kind of remember things. But if it goes away, like I wrote this, all this code a week ago that I was really proud of and I was looking at it like yesterday and I was like I have no idea what this is or how it works or anything like that, and constantly.

So, like, I just want to start there, which is like you know, programming's hard and I think some people take more naturally to it than others. But, yeah, I think it started from. It's actually funny. I think it honestly like probably started from your forums back in the day. I remember there was like I think you had like a how to make snow on a on an HTML page like thing tutorial. Yeah, right, things like that. I just didn't know that was possible, right, and so it was a curiosity, was kind of oh cool, and they could do these kinds of things.

Preceding that even, actually, I remember when I was using Netscape Navigator and, it had like an inspector panel thing and I remember going to, The New York Times website or something and, going to the inspector panel and it would let you. It was very different back then. It kind of made it feel like it was like a wizzy wig, like you were actually editing the page. And I remember going to like the page and like editing the title and then being really scared to hit the like save button because I was like, oh my gosh, am I like defacing like the New York Times? Is it gonna stay?

Because I don't know how anything works, right, and so, anyway, like all this kind of stuff, I'm just like I had no idea how anything worked, and so I think it was just this like slow process of like picking stuff apart and, eventually I would like have goals and tasks. You know like, oh, I want to accomplish something, but at first I'm just like, literally just like poking stuff. I'm like I don't know, I didn't know anything. These things existed, you know, so long-winded answer, but something like that.

11:54 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=714s)

I mean, that's pretty much how the world was back then as well, because I think, you know, I think both you and I kind of grew up together at the same stage of the internet and technology and all these things had like GeoCities and Lighthouse, and you know, I think, like MySpace was just coming about and you, there was no guidance. There's no like real tutorials or best practices or anything like that. There was no like O'Reilly book on like here's a definitive guide to how you build a proper web. I was like, totally what was like? Was it webmonkey, webmunk?

You had this, like you know, really cool, like bright colors, and they're like here, so you create a list and things like that. Yeah, I remember, like you mentioned Netscape right again, Netscape Composer was one of the first Ides that I ever used for like because it came free with their browser, then switched over to FrontPage Express because at that time, IE was having more of the cooler capabilities than what Netscape had. And yeah, you're right, you know we're probably dating ourselves like.

This entire audience has no clue what's going on, but you'll be surprised, though, like the demographic information I get from like Spotify and so on, it's a it's around exactly our age, which is not surprising topics we talk about. So we're basically talking to each other, you know, and that's the audience, right, perfect, yeah, I mean, if you want to go for the younger audience, I guess, just you know AI replace all the netscapes with Tick Tock and you know it'll be fine. Oh yeah, but speaking of AI, have you dabbled into AI to kind of help your coding go further?

13:07 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=787s)

In terms of coding, the one place I've found AI especially helpful is when I know the end state I'm trying to get to, but I don't know what the thing is actually called. I don't use Copilot or anything like that. I'm a little bit of an old man about new tools, so I have my usual set of things at work and mostly stick with them. I know, like there's an algorithm or there's a formula or something. I don't know what it's called. I don't even know how to search for it.

I'm not good enough at math to know what like the math to look for whatever, and so I'll just type in like very dumb things into ChatGPT and just you know, just describe the thing, and it'll- often spit out like some, morsel that will give me something googleable, right, so that I can actually find like a tutorial or something. But in terms of, like you know, I did play around a little bit with like the could I just automate myself.

Could I describe the stuff I'm doing well enough for it to just spit out the stuff I'm doing and I didn't quite get there, but I'm- that's more a limitation of myself, my prompt engineering skills, than I think like the tool. I think you probably could.

14:12 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=852s)

Yeah, I think that'd be interesting to see. I do like to play around with it all the time to see, like, how good it is. I do find that you know, ChatGPT, Bard and others are really good for like it's all the training data they ultimately train against, right? I think there's such a shortage of high quality training data for animations and visualizations in general because when I ask it to like you know, here I have a column of text: make it, optimize it like sort it or whatever, and write the code for it. Does a fantastic job. Both of them like copy and paste, the bullets paste.

Then it just works. No need to worry about it. I asked it to actually figure out: create me a performance Darfield effect, kind of the old windows screen savers, right, like you know, of it zooming in. There are many ways of doing that. You know the proper way is actually you create a fake Z, you know like three-dimensional area, and you are just that, and it changes the X and Y and scale and all these things appropriately, and every single example that came back from ChatGPT and Bard were literally just the same as like just x, y and scale.

You know, not bad, not a bad Solution by any means, but the perspective is off. The spaceship going right in the middle of it start and fly around you know, and it wasn't quite meeting it there, and, no matter how much I prompted it just gave me very inspirational the same thing.

Ultimately, the point where it just doesn't work at all, like it so required me to write coding, so I think we have a ways to go, but what I'm most impressed by with AI, though, is like Midjourney and Stable Diffusion and some of those things, because I'm not a designer, like I cannot design my way out of, you know, any kind of situation, and so I really enjoy seeing like that kind of capability exist for everyone. Just type in verbally what I want to do. And even like Adobe has Firefly, where they have some really cool things there. Have you played with any of those by any chance?

I haven't, honestly. I'd be curious, though. Like I know on your you know your website and your tutorials- you have pretty good graphics and feel very like tailored. Are you using, like, AI to generate?

16:00 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=960s)

No, I actually write them all. I still do them by hand. To me, that does not really count as art, though. It is basically me going to a whiteboard, drawing something, adding a caption, drawing an arrow, or including a screenshot or visual. I guess it is part of PowerPoint art in my world. Really.

16:19 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=979s)

That's an important distinction. So you're talking more about the illustration side of things, correct?

16:26 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=986s)

On the illustration side of things, I did try using both of them—well, not Stable Diffusion so much, but Midjourney—to see whether I could get something useful out of them. Like they, you know, I think, only until like maybe, like maybe a few months ago, was text actually legible and properly done. Like there's always a joke is, like you know, characters are like odd number of hands. They can tell yeah, exactly, yeah, it's really something like that.

That's, like you know, classic example: AI, but no one ever tried like put some text in there to see how bad that comes out right, and so I think there's still a little bit of ways to go there. But I do anticipate that happening eventually, though, because a lot of what I'm doing here is very repetitive, you know. It's like here's their vocal image, here's some lines, here's some text, and then, like you know, probably like some icon that is through into the Twitter Emoji set and that's pretty much it.

So there's no level like the creativity doesn't go beyond a certain limit which is perfect for AI systems to figure out.

17:32 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1052s)

What to do. Yeah, exactly, you can actually theoretically come up with like a fitness function here where you're like, hey, like this is accurate, right, versus like illustration, which is like completely subjective right. So obviously it's a totally different like Universe for quality and ensuring it right.

17:47 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1067s)

Yeah, and so, yeah, I think there's, you know, probably like maybe six months to a year away from having more of that, because I figured it went from like six fingers to now having text that look good, to actually having people pretty much like creating videos that seem pretty, decent. For the amount of time it takes to create things without you actually touching an animation to our video tool, that's quite impressive.

18:08 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1088s)

Yeah, the speed at which this stuff is moving is crazy. I feel like it's almost like a full-time job. I think there was like a couple months where I was paying attention on a daily basis and I kind of felt like I knew was going on. I haven't been paying as close attention the past couple months and it's like you're saying text is working now didn't know that. So like things are just moving really fast. Yeah, the funny thing is that.

18:25 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1105s)

I think it's been almost a year now since the latest ChatGPT wave, and maybe a little under a year for the newer image-generation tools, but the pace of change has been wild. And now I'm at the point where like okay, I know everything that's going on in this area. You know, with enough effort with AI, though, like I think it's almost like you know- we releasing the water from a dam somewhere and the water just keeps flowing. No one really knows how much more water is left on the other side. So you never get to a steady state, you never figure out.

Like okay, I learned all these things now, but then suddenly something brand new comes out that takes what you learned before into a whole new level of productivity. Or like I don't understand this now, like I need to relearn things like language. It was not really a thing like a year ago, but now that's the way you got to do it, to train things or a vector, databases and things like that, like just even conceptually keeping up to speed, you know, ignoring the technical details.

Even that is hard and the funny thing is like I spend a lot of time- my full-time job in some ways- to kind of keep up the speed on this and even I'm all completely yeah, I mean it's interesting. I mean, when I was still working, at Snowflake and just like other, like engineering friends in the field and stuff like that, one of my favorite things was always just to find the smartest person I could and just ask them to explain to me whatever was going on.

And I had people drawing me out like the Transformers or llms or like whatever pieces you know, like and like you can see them, like thinking they understand it, and then like working through it and they're like, oh crap, it's actually like a little more complicated than I thought it was and like obviously they all you know get there and they're all Geniuses. But, yeah, it's, I think just like the. Yeah, I think, yeah, I think you said it all right. I think just like the thing, the Black Box.

Nature of it I think is just interesting too right, like even the people that are building them don't know how they work fully right is my understanding. Maybe people do. But like I was reading, like I started reading, like the Wolfram, like 6 000 million, like page long thing, like walking through how llms work, you know, and it's just like trying to build it up from like first principles or just like basic building blocks and it's just like, yeah, you just can't and it's crazy.

20:30 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1230s)

Yeah, it's like the layers of abstraction needed to make sense of it are just massive. Like I never learned machine code or assembly. But you know, I'm glad it exists because it allows me to do all these higher level things I'm doing right now. But at some point- you know whether you kind of want to or not- you can kind of go: okay, how does my code go from like what I'm writing to what's going to happen? Or how does my visuals go from like the pictures on screen to something actually manipulate and make modification, to Vector raster and all of these things?

I think with AI there's just so many unknown areas. It's kind of you're just trying to find it, you're just trying to find a gripping somewhere. Okay, I'm gonna grip. I understand this basic part of it well enough to start as a point where, like, okay, I don't know anything about me, I don't think below me or the side of me, but I know enough of where I am right now to make this work. I think with AI you know a lot of us in this boat.

We're like there is no area where you understand enough to even have a solid gripping to know, like, which direction do I go through next, and you're right, even people who are experts in this field- they have a very narrow slice of it that understand really well. And it has to get narrower, because the field just keeps getting broader and deeper, very, very quickly. Yeah, you have like.

21:33 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1293s)

Exactly. That kind of teeny-tiny expertise can be out of date in five minutes. It's tough. It's very mile-wide, inch-deep.

21:40 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1300s)

Right, exactly, and so at some point, you know, we'll get to the you know area where the water hits. The hits the edge of the rivers and it's like, okay, you know, we know where the edges are now. Let's take a step back, take a deep breath and now go and then reverse, engineer basically the output into what's going on. But right now, even though the outputs are just randomly increasing in quality and Speed and Performance, and so- and yeah, it's gonna be interesting seeing, like you know, all these super computers going to like smaller computers and then your own devices Now can do like AI and things.

But it's a democratization of AI. I think it's like the new thing because we've had AI forever, like you know your credit cards, being able to tell you, oh, someone is using this thing, are you sure it's you? And you're like that's actually me, but good, call on that, you know, and things like that. Or you know airplane bookings and so on. It's always been there forever.

Or, I think for me a fair example, all the photo editing tools or even just like photo galleries, where you upload your own photos, type in words and be like beach, and then he just knows, like you know, like 10 years like, wow, that's really cool, but now you and I have the power to build something that is exactly this, and then every startup, every day, seems to be adding a Twist to it, which makes it pretty compelling.

22:46 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1366s)

Yeah, there's so much going on there. I think the one of the sort of side effects of this that I'm excited about is just the amount of people, working on gpus, and so you know like gpus are going to get like faster, more efficient, like whatever they're gonna. They're just gonna be totally commoditized Beyond where they are now, I assume, and you see so many people just squeezing every, ounce of power out of GPU. So you see cool new graphic stuff like every day too. If you follow kind of Graphics World, even like there was a hot thing in the past week has been like gaussian splatting.

Have you seen this? It's of the train right of the train engine in webassembly. Yeah, that's the popular demo. Yeah, so basically, just like I think it's like a handful of photos and then it just figures out that it basically makes a point Cloud out of like ovals or like blobs, and then you can just real time move around. It's super cool. It's super cool and I feel like maybe I'm overstating it a little bit, but my sense is that, like, this stuff is a little bit Downstream of all the AI stuff because there's just so many eyes on gpus, right.

23:47 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1427s)

Now? No, completely agree, because you know one of the big things that AI is going to help with greatly is an asset generation. You know, when you look at like, how complicated it is to generate 3D assets. Like you know, some of people I know work on Unity games and, like the editors, like they love the editing environment but they're like the hardest part is getting high quality models and they pay companies that literally take a camera on the back of a truck and, like you know, Drive hundreds of miles taking pictures and videos of, like a scenery around them, like you know, roadside and things like that.

Imagine a world where all of these are dynamically generated procedurally through just code and then the technology exists to smooth it out, make it look really good. That trained demo for me was like this is mind-blowing in so many ways because I felt like only a few months ago I was watching like the cityscape being designed really realistically and I was like, oh, this is actually pretty cool. Like you know, I can see geometric shapes and look, you know, the bridges and things look real. So now having a train where I'm like zooming in, I'm like, okay, I want to see where the imperfections are.

You can see it if you focus really well, but it's on par with like the best hand generated. You know games, 3D visuals you might see elsewhere and I think developers said that the actual human work to do that wasn't very large. This is the training and the generation part that took a little bit longer, which is like amazing. Yeah, it, yeah, it's mind-blowing. I mean, the math on these things is so well, so far beyond my like comprehension.

But just the fact that, like you know they're, they can- I forget the right terminology, but you know it- has real-time Reflections and stuff like that, right from like a couple of photos, I can just figure out how things reflect and things like that. It's just completely crazy. But anyway, this is like people can't see what we're talking about. So this is maybe not the best thing, but it's super, cool.

Yeah, I mean, you know, I think for those watching on YouTube, I try to put like a video of it overlaid on top of both our faces, so this would be, like you know, as awkward as it can be, but perfect, yeah, but no, I am always impressed by that. So yeah, so yeah, AI can kind of make a lot of these things that are hard, easy, but if you don't know what you're doing, sometimes you might have to spend a little bit more time figuring out where the AI went wrong so you can debug it and figure out what's happening there. So, all right, so you know.

So you've been doing all this work and then you decided to build your own company. Tell me more about that.

25:54 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1554s)

Yeah, let's see. So, I was on another brief break at the time, after, going to a startup that didn't end up handing out, and, a co-worker of mine that had worked, with me at Dropbox before that startup, I started working on a new project and the basic thing, the way he kind of explained it to me- was like, he wanted to figure out what he could do as an individual to make a dent in climate change, like if I recycle more, if I stop Flying, or if I buy an electric car or whatever, like which of these things will actually be like matter the most?

And like, how do I actually work through this kind of thinking from kind of a more consumer kind of level, right, like, where's the Google docs for this or where's the Dropbox paper for this? And I was like, oh, that's kind of cool. Like I don't know, like I'm not an expert in this space at all. I think it's a totally compelling question, and it also sounds like, you know a compelling design problem, right, and so, we ended up working together. So, his name is Brian Smith and, yeah, it's interesting because, that was.

I think that was kind of the Inception and then, like startups, like we had many detours along the way- like this thing for one period of time was a way to it morphed into like a way to diff like your financial model from like Excel and render it on the web and give you like a like a GitHub diff style thing, and then at some point it would turn into like a data visualization tool for like data journalists, and so then it was like a way to kind of suck in like data from anywhere on the web and like kind of get like cleaned.

Relatively clean- data that you could like kind of work with and then eventually kind of morphed into this more just like traditional bi SQL editor thing. But, I'm kind of getting ahead of myself, but like yeah, I mean, it was kind of just like this curiosity around, like could you build a tool to like solve this problem for like our kind of personal need? It was not some sort of hey, we have this like massive business idea that's gonna like change the world. It was just kind of this thing should exist, let's make this thing.

27:58 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1678s)

Yeah, and I remember when you- I don't remember the parts of the very early series of startup, but definitely when you had the data visualizations of like here's some data, here's gonna visualize a really nice way. That's when I really noticed it, because at that time I was at Salesforce and Salesforce just bought Tableau and so I was like, okay, what is this Tableau thing? Like? You know why, you know what is so interesting about it. Salesforce had to buy it. So it's like reading up on all these kind of activities.

And then your art- your tweets actually came out quite a bit and you know the part I think that's also like interesting about what you're describing is your ability to simplify and share ideas visually in the Twitter, and I took a tweet like form. I think that's highly understated. It's actually very well done. Like I remember all the time like some of the most effective things I always see is like, okay, that's a really nice idea but visualized poorly, or it is described absolutely awfully, but you seem to have a knack for being able to have that marketing side totally figured out.

28:52 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1732s)

Interesting. I feel the exact opposite. I feel like I am aggressively bad at Twitter and tweeting, but interesting to hear. I would say like the one thing I would just say on this is like, empathizing with no one caring about what you're doing is really important skill. If you're doing anything visual or like design, right, like you just have to like, you have to completely just whatever work you put into whatever output, like you have to just eat it. Doesn't matter how long it took, it doesn't matter how hard you tried. Like you just have to eat it and you just have to like.

Assume like the worst critics are out there and just kind of you can optimize for that or you can ignore that or whatever. But I think like, if you kind of just like take that, it helps a little bit. Right, it's like if you're if you're a harsh critic of whatever you're putting out, it helps. I think so, and that's why we.

29:42 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1782s)

Meet generalizing poorly here. But I also think that because you know, you and I guess, like are used to creating content is putting it out there all the time. We grew up in a world where there was no Instagram, there was no Twitter, there was no like real-time feedback where you could be like: oh my gosh, half people don't like what I'm doing. There was not that. The feedback loop was so time consuming and long that it just became second nature to be like: this is going to share this out, like what's gonna happen? Like will anybody see it? Maybe, not. Who cares?

Right, whereas I feel like the generation of designers and developers is people coming up today is in the back of their mind. This has this fear that everything they're doing is being judged, will be tracked forever, and this portfolio they're building is always going to be available somewhere. Like do some hesitation where you know we talked about earlier, just ship it out there's, get it out there. You know? See what happens unless you know, you know we formats were the MVP, I think, like that became a term, but I think you and I probably had the idea of MVP even before.

Those formal thing was like I'm building something, let me just try it out, put it out there, see what people say and then iterate on it in the open. I feel like that has gone down quite a bit in terms of like the art, like and the Creations I see people sharing these days. Yeah, I 100 agree. I mean, I think the.

30:47 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1847s)

Yeah, I think you can kind of track this history, kind of looking at like Instagram. I think it's probably like the best example where it's, like you know, started out as this like casual place to post photos that you're doing stuff with your friends, and like it was just like chill, no one cared, I'm having coffee, whatever.

Twitter was like this when you started too, and then it turns into, you know, a bigger Network and a bigger Network, and it becomes kind of almost like you're, yeah, your permanent record to like put something on like your feed, and then they come up with stories or steal stories or whatever you want to call it. But, like you know, okay, here's our escape hatch where you can still do casual sharing. But you post on Main. You know, yeah, it's like your permanent record and this is going to go with you everywhere and that's just permeated. Everything. Now, right, and I think I'm stating the same thing you're saying.

But, like, it's interesting where, it is scary right to like put something out there and be like attached this to me for all time. The good thing is it's like I'm very mixed on this. I like, I mean, I have a very love hate relationship.

Like every social network, I've deleted all my everything's many times and sometimes I'm like I'm professional, sometimes I'm not professional, so like I'm very scattered shot on this, but like I do think that, they're sort of a there's a balm a little bit which is like: okay, everyone's posting a lot of stuff and so like your stuff is just gonna drop a drop in the bucket, so don't worry about it so much and just kind of get out there and do your thing.

But the other side is like that's true in real time, but you also have the historical record where you can go like look at someone and you can like scroll back and be like: well, this group up dude, 10 years ago, and it's a little weird, you know, it's a little weird. So I empathize with the people who are skittish, but it also is sad because I do wish there was a more exploratory, like kind of world out there where people weren't afraid and people were taking bigger risks and just being a little weirder. And we do seem to have like lost that.

32:31 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=1951s)

A little bit, yeah, and I think the other angle also is that the way content is surfaced to you and I is very algorithmic and there's a pattern of what follows is like: you know, here's the kind of content that's going to be trending and make it, you know, seen by other people and here's the con that will not. So indirectly, your behavior is also influenced by: do I want people to see this? If I do, here are the things that I need to do differently. So the authenticity of like- here's why I think- is I want to create. Is it now? It goes through multiple layers of.

I need to adjust this, tweak that at this and make all these things. Because if I see one more video on like how Mr Beast does his video thumbnails, like, I get it. He makes good thumbnails, but not everybody. What about the authenticity of like people doing quirky things- and it happens every time, right and another. Some new networks can come up, being like we're for the Indie developers and designers. You know we don't care about our popularity. That becomes hugely popular and then it either gets sold to a bigger Network or it stays and it becomes very popular. Where again you have this thing?

Where like, how do you, how do you surface content without overwhelming people with like a billion things like? Deviant Art is still around and I see them like having the exact same challenge because I think during our time they were the place we went to. It's like a hip Community where just like throw things out there and see what happens. They're still trying that right now, but when you have like tens of millions of people, it becomes very, very difficult to maintain it. Yeah.

33:54 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2034s)

Yeah, there's the maintenance side of it too. One thing I think about is just how breakneck the pace is at which new formats keep emerging. Ad placement next to what's the right length, what's a good, you know what's a good opening paragraph, like all this stuff, right, and it probably took I don't know hundreds of years to develop or something, or decades. And then now he's just like: okay, new Social Network, new, pattern, new Norm, new way to game the system. And then just another, one another, one another, one another one.

It's exhausting, right, and so I think there's also just like a very like unnatural, non-human scale evolution of, like the way that, like, we build community on the internet too. This sounds very Doom and Gloom. I'm glad this stuff exists. I get exposed to cool stuff all the time. I find all kinds of neat stuff, but, it's a weird time. It's a weird time and I just feel like it's accelerating, which is weird.

34:48 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2088s)

Yeah, it really is. Speaking of upcoming new things, are you interested in AR and VR and some of that world?

34:54 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2094s)

Going on there. I am looking forward to getting a Vision Pro and, just like you know, putting it on and like walking into a wall, but, I so far have had- not, I haven't had- a very successful or interesting kind of relationship with the stuff that exists today. Like, I have a couple of like the VR headsets and stuff and, just like the motion tracking stuff, I get very harsher emotion sick and I just like it can do it for like five, minutes and then I'm like out of it. I would say the technology and the Vision Pro seems amazing.

I can't wait to actually try it in terms of just, you know, using your hands and like the eye tracking and all this kind of stuff. And I think there's gonna be a lot of cool, new ways just for people to like experience visual spatial stuff. I don't really know, you know how to say it. It's just like a whole new, whole new terrain and I think very interesting things will come out. My fear is that it's, somewhat of an isolating technology, right, and so, this kind of slow trend of like what we're doing right now, right, we're on screens together.

It's good we're connecting, I'm glad, but, you know, more people sitting on their couches plugged in all day is not a world I'm super excited about, so I'm very mixed on it, right, I think like yeah.

36:10 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2170s)

No, I completely agree with you on it, you know, I think it's just that I might think COVID didn't help much in terms of like normalizing video calls and some of these activities. And yeah, I think the Motions against part is saying I really, you know, I completely relate to it, because every time I use any of those devices, after like what five minutes, I'm like sweating profusely, I'm like, wow, I basically look like this brand, like a 5k or something in like 10 minutes. And that's where I think the Augmented Reality Part I think might help a little bit, because the parts are peripheral, like everything.

So like based on reality. So I'm turning head around very quickly. It can be like, okay, the room is still adjusting, you know, at the right speed. It was supposed to like lagging, even subtly, but yeah, until we tried out, do? I want to know? Because after the hololens that had its you know pros and cons and I definitely felt a little bit of like you know, more thickness from trying that as well.

I never could try to Google Glass, but to me that was the right form factor because it's just a glass and it's like you know, walk around with it because I think eventually it's going to get to the point where I'm looking forward to, you know, like kind of a newer link like thing, where I was like, you know, just open me up, stick a chip in there, then I'm good and I know where to charge something, to carry nothing with you, because, you know, I was always a skeptic of this, but I got Lasik about like a couple of months ago or actually a year ago at this point.

Right, okay, my good experience. I'm like, wait a minute. My vision went from like something like you know, it was like it wasn't bad, but it was like still, you know, blurry if I didn't have my contacts in. Now I have, like 2010 Vision. I can actually see, like even better than like without you know, with that, even with glasses, I'm like that's amazing. This is a kind of biohacking that you know, you always read about. It's like the end of humanity.

I'm like, sign me up for more things if there anything like that comes up, and so that kind of probably changed my perspective on like where does Hardware end? Where do humans actually begin, which is probably another whole terrifying World in its own way.

37:53 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2273s)

Yes, that's interesting. You took tiny steps along that path, and now you are saying, “I am going to go the whole way. Just wire me up.” I think the Neuralink idea is to skip your eyes and go straight into the brain. I am on the other side of the fence on this one; I am a little terrified of Neuralink. I hear you, though. Going straight into the brain feels like a much bigger step.

38:16 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2296s)

There's a, there's a leap ultimate from you know you had a startup and you know, I believe it was sold to Snowflake, correct, yeah, So you know that's, huge in its own way. And then you, at some point, you shifted from being essentially a designer to being a manager of designers. So how did that transition work? How was the big learnings in terms of like, how you had to adapt to a new world?

38:36 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2316s)

Yeah, that's an interesting one. The TL; DR is that Snowflake bought Numeracy, because we were doing innovative web work around data visualization and querying, and at the time Snowflake was much more of a database company trying to build better tools around that experience. It wasn't really the right tool at the time, and it also wasn't a modern web stack. So they brought us in, and pretty shortly after that there was still an open question: is this going to stay a supplementary product, or are we going to fold a lot of this thinking more deeply into Snowflake itself?

Or you know, we're gonna bring our stack into Snowflake and kind of keep the UI similar and kind of rebuild the existing stuff inside of this like Numeracy was the name of the startup, inside of this Numeracy, UI, and then kind of, go from there, that's gonna be the New Foundation, right? So anyway, with that, they were like, okay, well, who should be the person that's going to kind of lead that effort from, like the design side? Well, maybe the designer from that thing, which is me, and yeah, my boss, who is that a product? Basically was like, do you want to try this like design management thing?

And I was like, you know, maybe, and we had a bunch of conversations around it and, ultimately I landed on like, hey, like this is a huge learning experience. Like these, kind of opportunities don't just kind of show up that often. This is certainly not the path I thought it was on, but, yeah, let's give it, let's give it a crack. And you know I got a lot of support from him over the years. But, yeah, I spent, a few years, building up the early Design Team, all the way to when I left.

It was on the order of 30 plus folks on my team who were doing, you know, all over the world doing all kinds of interesting stuff from user research to design operations, to just like product design and like a bunch of other things and, yeah, super interesting. Maybe I'll pause there. I think you had other questions, but I feel myself going.

41:14 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2474s)

On and on. No, actually, that's actually. I always enjoy hearing more about it because the shift from being an individual contributor to being a manager is a huge one, because there's really no guidebook. Or just like back in the internet days- right, early days- of Internet- there's really no guidebooks that are actually applicable, because it's so context sensitive. You know, every situation is very unique. Every environment you're operating in is very different. You know Snowflake is very different than Salesforce and Google, than Microsoft or any of these other companies.

So, like whatever best practices exists in the, you know, LinkedIn thought pieces are absolutely not going to be applicable to your case. So how do you manage a transition? You know you mentioned you had good guidance from your manager at the time, but there were a lot of things you just had to learn along the way. It's what's the most biggest learnings.

41:56 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2516s)

I mean, everything was a learning. It's super interesting. I mean, I think like, probably like the core. The core learning for me, honestly, is: just like people don't operate like you operate like whatever it took for you to get to where you are is not going to work for other people in the same way you're saying like this is like this generic advice that you're going to read isn't going to apply to like the context you're operating in. It also doesn't work for your team, right, and you shouldn't hire a bunch of people that are just like you either.

Right, like you theoretically could hire a bunch of clones, but I don't think that's smart. And so, yeah, I just like you know, like I think like the things that motivated me- this is like almost bad to say, but like I'm kind of shame motivated. I'm kind of I just like if something's bad in my name's next to it, I just like can't handle it.

And so, that motivates me to try harder and push and push and push, and it's not necessarily the healthiest thing and it's not like the thing I would like encourage other people to like develop, but you know, useful for me, whatever, and so like working with like new folks and just figuring out like new ways to like motivate people and new ways to talk about, kind of you know what's good enough and one's done, and like all that kind of stuff. Those kinds of things were like not the things that I thought would be as challenging.

You know, I think I kind of naively assume there's kind of, just like a shared understanding of like anything right, like quality or rationale or whatever, it is, and just learning that like, oh, everyone, actually thinks about things completely differently, and that's, the benefit, that's the benefit of building a design team. Is it like you get exposed to different ideas and you kind of you know, materialize that stuff in different ways, but yeah, people are different than you. That was that was a surprisingly challenging learning, like everyone's, not you.

43:40 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2620s)

Did you also get to do some design work there, or were you full-time just managing people?

43:44 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2624s)

Managing people. At the time I started hybrid, so I think this is very common in like new managers, particularly in design. Like design is a field, right, it's still like relative, relatively like Mason field and like, I've worked at a handful of like series engineering companies and like engineering kind of people kind of know how to run like an engineering team at like a serious scale and stuff, but design teams are a little different, all a little weird. So, and also like, leadership doesn't always know what to do with designers, right.

So, yeah, I was doing design when I started managing, which is like, when I look back on it, you know it's like, okay, just join this company from a startup. You need to figure out how to like a learn what this new company, does, and then you also need a charter path forward that like makes sense for the company. You also need to adapt this thing to this other like alien thing. And then also, you know like figure out how to design is like design some new features at the same time and figure out how to manage people at the same time.

Was doing a little bit of that for a little while. Painful, interesting, interestingly, probably useful honestly, to design with like the early team, to kind of build credibility, you know, and like Rapport, and that stuff does kind of radiate out over time like your credibility does kind of you know matter, like in that way. But painful,.

45:01 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2701s)

You know there's so many studies. You know. The ones I do tend to agree with are that, whatever discipline you're becoming a manager in, you should still be qualified to be an individual contributor. If it came right down to it means, if you're a design manager, be able to both appreciate good design identified, critique it properly and be able to do things just like it for an engineering manager. You should still be able to understand high level coding Concepts and maybe even write code as well. Same with product management and so on. And do you feel that is also relevant?

45:28 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2728s)

In your field as well. I think it is. I think it's interesting, like at a certain point it has to break down right, like you can always start from the other end, which is like there always has to be a CEO and there always has to be you know people under the CEO and eventually like theoretically functional leads or you know whatever we can do, the GM model- but, I think it helps a lot. I think at some point I'm biased on this, but I think you do want someone leading the function who does actually have that credibility too.

But you see models where there's totally successful leaders of like design organizations who, didn't come from like a product design background. They come from a writing background or operational background or whatever. And it works. It's just. It's just a different. Depends on what you're optimizing for. I guess it's like the short way of saying it right. Like, if you're optimizing for like world-changing, game-changing design, you probably want someone with like the design background. If you're optimizing for scaling, maybe you want operational background. You know there's different ways of looking at it, exactly I think.

46:29 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2789s)

You hit it exactly. We use different terms for different kinds of people: zero-to-one people, operators, and so on. It really does depend on the stage the product is in. If you're trying to build a product from the ground up- very different set of teams- you need to be able to- you know, work in ambiguity even more so than normal and be able to take decisions very quickly, which means they probably have a sense of what is good and bad across any discipline there's currently, you know, currently- operating in, and then you get to the point where, okay, now we're more of a mature product line.

How do we make sure that we don't break things too much? And there's a whole different set of things. Think about, it's one thing to go from like zero miles per hour to 30 miles per hour in your vehicle, then go from 30 to 45- very different set of skills and the people who might have built the 0 to 30 mile per hour solution probably bored or their mind. They have to basically just incrementally move the needle to like make something move better, and it also do the company's culture as well.

You know, in top-down cultures there might be like slightly, a little bit more impetus on the person who's making the calls, having enough domain expertise to not say something or do something or guide the team interaction. That is completely, you know, off the rails, whereas in a Bottoms Up culture it could be there's a little bit more wiggle room, where decisions are often made by the people who are actually closer to the actual work and less so on the leadership. This has to. I guess number would just be an umbrella to protect them.

Yeah, that sounds like there's a whole separate, probably podcast on that topic for like a company, like a Snowflake doing design at that kind of company right, where it's like the designers typically don't come with deep domain knowledge on like database, internals or you know ETL or like whatever right and figuring out how to like build that, knowledge throughout the organization and like how do you balance like the sort of technically correct, maybe that comes from the side.

Or like top down, like how do you stitch together like eight, like random complicated things, or like Bottoms Up, like genius idea that emerged out of like the woodwork, like all that kind of stuff is like very interesting too and like, you know, it's- I think it's a slightly harder playing field than your consumer apps, which is like you can just kind of empathize with like the problems and you just like, yeah, like you probably want to be as bottoms up as possible, versus like an Enterprise kind of thing, where it's like.

It's all kind of got to make sense together somehow, and actually, you know, a lot of smart people are working on this in, like, different places. It all has to cohere. That's tricky. Yeah, very much so.

And you know, also like getting back to the manager role in some ways is that when individual contributor, your number one goal is like, okay, you know, have this task, how to make the best thing possible, and like you know, and ship it and make sure you know that's all the right things and, depending how senior you are, your criteria and went off for Success might be, you know, broader than your immediate team.

When your manager often found that in many situations, you see the end result, you see exactly how this should be done, but it's not in your best interest to tell someone here's what's going to happen if you go down this path, and so this balance you have a strike between: like the right thing for the product is to make sure this error does not happen, but the right thing for the growth of this individual is to go, think through the process, make the mistake, learn from it so they become more effective as an individual contributor and one day, when they become a manager, they can also take these skills forward.

And those tensions are often like no one ever talks about it or writes about that. But that's those. Are like that's the art of management, which I find always very confusing. I think it's the right thing. I.

49:49 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=2989s)

I think it really is an art. If there were a science for it, I would love to read the paper and make this easy. You want people to learn their own lessons, but there is tension because that slows the business down in the short term and may create challenges with coworkers. You have to let it happen judiciously. If you find the energy to write that tutorial, I think it would be helpful for everyone. Balancing learning against short-term business needs and coworker challenges is the difficult part.

50:18 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3018s)

Oh, I'm still learning. You know every day, like I think I mentioned before, like I optimized for only large companies, because at some point you realize the skills you learn are click or you know either apply to small companies or large companies, and if you want to be a domain expert in that field, you have to choose one and stay in that particular Lane. And so, for me, I'm like you know what. I have this knack for understanding organizational politics and drama and chaos, and so I'm just gonna go into large companies, because the things I learned here only work in large organization.

If I do this in a smaller area, it's going to be like: either I'm completely like giving guidance- that is way wrong- or I need to learn a whole lot more at this point, which you know might just be way too much to kind of do this, and I always look for what are patterns that I can use to generalize so much of this, and again, it's so contextual. There is no real pattern in terms of this right because, for example, you mentioned that you're reporting to a head-up product. There's many situations where it's worked out really well.

You know where a person of a different discipline you're, you know you're working with that person. You know their manager, and it's been very successful. I've also seen many cases where it was absolutely did not work out well because the context awareness and the appreciation for the little details that only someone who's done that at an IC level or at a manager level long time ago would actually understand. Like how does something go from where you were headed to where it is now? And so again, there's no pattern I can come up with.

So if I ever wrote anything on it would basically be a condition of if else statements and say like if the next paragraph will completely contradict that because they're, you know, it's all based on people, it's all people, it's all. Yeah, Dynamics, time pressure goal: yeah, it's a lot, it's a lot, but yeah, I think that the functional important thing is actually interesting. Maybe like a quick note on that.

52:00 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3120s)

I think one area where I got lucky was with the head of product I reported to the whole time, Christian Kleinerman. He was awesome. He basically created an environment where I could learn the job while doing it.

He was just basically was like you know, you're the domain expert run, I'm gonna give you sort of company priorities and like I'm gonna like kind of keep you on the rails in terms of like the big, the big picture, but didn't get in the, didn't get in the in the weeds or in the in the way with, the design stuff, and I think that's a good model sort of, you know, sort of the keeping you, keeping you pointing in the right direction but letting you do your thing, and sort of in that sort of you know, learning from your managers and kind of working with your team.

You know I had, I had- a research reporting to me and it was like kind of, the same thing in reverse and I had a user research and you know, was lucky to kind of try to get to emulate some of that kind of stuff too, which is like cool, like you're the expert, like go, do your thing I'll. Help point you in the right direction, but I'm not going to get in the way and like tell you the study's wrong, or you know your findings are wrong or whatever. So, I guess if there's a point I'm trying to make here, it's that, you know, working for a good manager.

I think if you're becoming a manager and you want to become a manager, you need to work for a good manager. I think if you're trying to become a good manager and you just work for some random person, you're gonna have a much harder time.

53:15 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3195s)

Completely agree with you, and you mentioned the word luck about two or three times here and I think that's actually a critical part of it because, oh yeah, when you're working for a small company, you know the chances of you being able to better have an idea of the team culture and how you know individuals work and so on. Greater, you know I'm not going to say give it 100 chance because I'll get 50.. It's probably the best odd to give any situation of the sword, but in a large organization there's so little insight you have into how things go, because the larger organizations, the more microcultures exist.

You know you could be in an organization that's historically known for a certain type of operation, but you could be in a team that is very different.

You know the leadership team of the team has a different way of doing things and you could actually be like: wow, that's actually really cool and I expect that you know, in terms of this- and that's one of the things I always like think about when I write- you know I do a lot of time mentoring other PMs and other people who are like about to enter, join the career and they always explain like having a good manager is the most important thing of all.

Yeah, everything else can be arranged, can be moved around and things like that, but the first couple of manages you have, especially early in your career, until you get a good, solid idea of, like this is right, this is wrong here, so I'm going to do this, and so on, be able to defend it. Having that level of you know great people to guide you is absolutely critical and it's one of the things where it's just an industry overall, we don't do as good of a job on it because everyone is your best foot forward during the interview process and you have such little insight both on both ends.

The company hiring you has really insight into like who exactly you are in terms of how qualified it's, your portfolio, they see your ability to do various tasks, but it isn't until you actually join you get a good feel for that person is, and vice versa as well, because oftentimes if you're working in a cross-functional role, it's not just your manager, it's a quality of the people that your manager is working with. Yeah, that play a big role as well, you know. So it's one thing to have like a fantastic manager and then very low agency peers.

They didn't have to, like you know, negotiate with and so on, and these are all things that you never know until you actually joins. So the luck part is often critical and you know if I ever do write a book, they'll be on. How do you maximize luck? How do you increase the chances of your situation? You can be more successful, and I think those go back to do you enjoy what you're doing. Are you really good at what you're doing as well? Because just put the hours in and you're really good at that.

Those are the kind of tangible skills that aren't going to guarantee that you won't be in a tough spot, but at least it'll give you enough ammunition to at least survive the first couple rounds of a zombie wave. Yeah,.

55:35 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3335s)

Are you getting better too? I think that is another important question: Do you want to get better? Growth is really important. Another interesting dynamic for me with these kinds of companies is that you mentioned deciding you want to remain at large corporations. I assume it took you a while to reach that realization, and you did not start there. Is that right? That journey toward choosing a large-company environment is interesting to me.

56:02 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3362s)

That is correct. That is correct. And for me it was interesting because I still- I still do cryptocom even now, yeah, and so for me that gives me the balance of like. When I have a day, I'm just like, okay, all I did today was just push an email back and forth between 10 people, made zero progress.

Let me quickly just do something on the side that gives me the satisfaction of this day wasn't a complete wash, so that kind of gave me the balance where I can go fast, break things and do the stuff that I do on the side, but also kind of do the things at a larger company.

I did not, yeah, right, I did not know this is exactly what I wanted to do, but once I got into it and once I made enough mistakes and learned how to not make the same mistakes again, I realized the skills that I have right now pretty much qualifies me to be more successful in a larger organization than it does in a smaller one. Yeah, I think..

56:49 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3409s)

I guess two things. First, the point about having Kirupa. Com on the side is super important. Same for me: while I was figuring out this management stuff out and feeling stressed out, making weird art on the side was really helpful. So like I agree with that. But the. Reason I asked you about the question about it didn't take you time to figure out that you wanted to run a large organizations - is because I do have this feeling that the generation, the younger Generations now are all kind of in a Sprint mentality of like, pick the perfect company and just climb the ladder as fast as you can.

And I think, like that was certainly not my experience, like when I got into this stuff and the world was different then. Design was a much more nice field, but I just got exposed to a bunch of different stuff and I think that was extremely useful and so, like we were kind of talking about the importance of having a good manager. I agree, I also think it's important to like get exposed to less successful or like less, yeah, less effective, like working Styles and things like that.

Like I've learned all kinds of like anti-lessons throughout my career and like those were as valuable as like the positive lessons, right and so, I do think it's an interesting thing now where, like at least in the design field, because it's maturing, it does feel like there's a little bit more of that sort of I don't know what the right, the right word, just institutionalization or something right- where it's like you know, just like get in, pick the right thing, climb, and I think people should be a little more. It just takes a little while to figure out, like what the right fit for you is right.

58:42 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3522s)

No, completely agree with you, and I absolutely agree with you- or comment on- it's also good to be an unideal situations where you might have a crappy manager and things like that. Like I would say that some of the best learnings- and things have actually had things to do- was under a series of managers who I would say were not very good, and that gave me more confident section some ways, going like: okay, you know, this is a weird situation, but let me try to understand. What is it that they bring to the table that makes the organization still value them?

Because I always found that poor, effective managers are enabled in some form of fashion. Like you know, there's a case where they are, you know, poor in the next six months, a year later, they're ultimately, you know, managed out or up, you know, whatever the, however, the company decides to deal with poor performance here. But in many situations, though, I feel that they've been that way, in that position, for a long time and they aren't doing any repercussions of it, and it kind of makes the question like: wait, is it me, am I the problem here?

Am I the one who is just not able to relate to what this person is doing, or are they doing other things that they cannot see? Because as a manager, you probably know that your reports are very limited insight into what your day-to-day job often is and the amount of heroics you probably do on the side to make sure their day jobs are, you know, going the way they do often goes under, unknown and underappreciated and so often try to figure out like, hey, what are they doing that? I don't see that might give them an edge.

It actually makes them very valuable to the organization as well, and those things have been very valuable. You know, in terms of internalizing, like, okay, this person isn't doing these things here, but were they doing that makes them successful and what can I learned from that? You know, like, if the managers, even your manager, aren't getting along, I feel like your time in that team or a series is limited. Anyway. You don't be there for a long time.

So the moment you learn what it is that makes them valuable the organization- you take that with you and you say like, okay, how can I apply this in a hopefully a better way than my manager did, but still take some of the positives and carry that over into like large organizations. This goes back to like why large organizations are ones that I specialize in, because those kind of things are often not really done as much in smaller companies, where you know the culture Clash is too evident.

Either you're out very quickly before you get to learn it, or your managers out very quickly before you get to learn from them, and so larger decisions give you the kind of the buffer where just bad decisions and bad individuals can Thrive for a little bit longer. Yeah,.

1:00:51 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3651s)

100. I agree with that. I also think it's important to at some point decide if you know, feel like you align with, like whatever the incentives are for the organization that you've kind of figured out by like looking up or looking out or whatever right, so, yeah, all that stuff's really really good. I think there's that Curiosity, that mindset of just kind of trying to figure out how it all fits together. Benefits everyone, right,. So this is again like my plug to I don't know who: just yeah, this like straight line approach I think is never the right, the right thing.

I think it's just like, yeah, try to figure it out, try different things, like all that kind of stuff. So, yeah, plus one.

1:01:28 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3688s)

Yeah, like the whole idea of like the game of chess analogy often like it makes more- makes it more clear. The longer I'm in like a large organization, my scope keeps increasing and I'm like, yeah, there might be cases where here's the obvious path, but if I take this path, how will all these other people in periphery react to it, in even their own organization? How will they react to it? And how do I navigate in a way that, depending on your style, you know you could, you could be definitely one of those people. It's like you know what's in it for me.

How can I make sure I win or my organization wins at the expense of everyone else? But if you want to think about how to make sure that everybody wins, you know, in certain fashion, how do you game this out? And so for me, like all the video games I used to play- you know I've played a video game in like last three, four years now- in many ways is because I've taken all this role-playing games I used to play, you know, on my screen and now I applied to the real world and sitting there going like, okay, I have a 20 chance of this conversation going on this way.

What is this. What is the secondary option where we both walk out of this feeling like we did something, you know something good. Or do I just roll the dice here, just say, okay, I'm just gonna do this and you know and see what happens so many times and I find that's exactly like what your day job is sometimes. Yeah, that's a.

1:02:34 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3754s)

That's a good analogy or a good tool set. I guess it's very, very analytical. I think I probably would have benefited from doing some of that. So that's another tutorial you could write. Well, I mean the space Skyrim play, Skyrim, Fallout, any of those kind of games where you're pretty much throwing the deep end and you just have to slowly grind your way into, like, having the skills needed to survive, and then a lot of it is going to be talking to people and choosing options in conversations that you know either lead to what you wanted to happen or the opposite.

But nice thing about being able to save the game and you can reload it again. It's a little bit more difficult to do that. Yeah, that's funny. No, that's a good. That's a good. That's a good analogy. I like that, yeah.

1:03:12 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3792s)

Yeah, I know we've been chatting for quite some time, so one last thing I wanted to ask: I noticed you've been experimenting with generative art again.

1:03:24 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3804s)

Oh man, that's my current white whale. Superficially it just looks like interesting, maybe cool visual stuff you can see in a browser or on social media or wherever, but it's something I've done on and off forever. But it's just like a bunch of like triangles that were like mirrored, so like basically random triangles, basically just like ugly butterflies or something. I don't know and but like, just like that sort of ability to create something on a screen that is like super human speed, right, like you can just get something like out and it can have a Time component and all this stuff, whatever, like.

I think that's like a very interesting problem space. So, fast forward to. I'm now doing this for probably 25 years or something, which is insane, and I don't think I've progressed 25 years worth of like skill or anything like that, but I have progressed 25 years of hand ringing, so I spend a lot of time, picking apart, like, what I'm doing and why I'm doing it, and is it interesting and am I contributing anything to anywhere? And so I've just taken the fun out of it. And I still like doing it, but it's, I'm trying to figure out what the next steps are.

So, yeah, for those who those aren't aware, you can go to my website, Joshua jenkinscom, and like there's just a bunch of web browser-based animations, column animations, I call them work sunscreen. And, yeah, it would be good if I had something smart to say about this, because it is something I'm taking kind of seriously, but it's also, it's. I'm in the early stages of figuring it out.

1:05:33 - Kirupa (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3933s)

No, I think it looks fantastic. For those watching instead of listening while driving or sitting in traffic, I am going to put it on the screen so they can see the animations you have been posting. That will be great. Josh, thanks again for chatting. This has been fantastic, and we should absolutely do it again soon.

1:05:51 - Joshua Jenkins (https://www.youtube.com/watch?v=Hr0omR9fV50&t=3951s)

Yeah, thanks for having me on. It was good to reconnect.


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