James Brady - VP of Technology at Teespring

(Joel Beasley at 00:00:00) Hello, my friends. Today we are talking to James Brady, the CTO at Teespring, and we discuss opening up and taking more risk as the organization scales, building habit loops to achieve your goals, and the expansion of product development. All of this right here, right now on the Modern CTO Podcast. This is the Modern CTO Podcast. It's James Brady.

(James Brady at 00:00:34) Hey, Joel.

(Joel Beasley at 00:00:35) How are you, my friend?

(James Brady at 00:00:36) I'm doing well. Thanks. How are you?

(Joel Beasley at 00:00:39) Amazing. Your audio sounds really good.

(James Brady at 00:00:42) Thank you. That's the nicest thing anyone said to me. I think we all care a lot about audio quality right now with the quarantine, right?

(Joel Beasley at 00:00:49) We do. We care about audio quality. We care about video quality. And yeah, those two things. And then we care about bandwidth, making sure that...

(James Brady at 00:00:58) Yeah, there's not...

(Joel Beasley at 00:00:59) Too many people at home on the internet.

(James Brady at 00:01:01) That's right. Yeah. Strange times.

(Joel Beasley at 00:01:04) Where are you calling in from?

(James Brady at 00:01:06) I'm currently in Spain, in northeast Spain. And we have been living here for a few years, and I'm already remote. I was remote by default beforehand, actually. So for me, for us, the audio quality bandwidth stuff has been a pain for maybe two or three years rather than rather than six months.

(Joel Beasley at 00:01:28) Now have you been remote for a long time? Like, have you always been remote?

(James Brady at 00:01:33) Yeah. Not always. So my first company, we were sort of bouncing back and forth between London and San Francisco. So I guess partially remote. There's a couple of years, 2014, 2015, where I was in an office in San Francisco, but apart from that, yeah, over the last 15 years or so, I've been remote.

(Joel Beasley at 00:01:54) And I thought this was so interesting. You found this thing called a micro village in Spain. Tell me about that.

(James Brady at 00:02:02) Yeah. Yeah. So by a micro village, I don't know if there's a dictionary definition, but the place that we live, there's around about 200 people living here. And we know a lot of them, obviously, as you'd expect with a village that size. And it's just a really nice close-knit, very friendly community. Doors are open all the time, that kind of thing. So, you know, before here, we were living in London, which is 10 million people or whatever, and then before that, San Francisco. So it's a big change, but one we were aiming for and definitely found a different pace of life, let's say, here.

(Joel Beasley at 00:02:41) So do you like it?

(James Brady at 00:02:42) Yeah. I love it. I mean, the thing is we decided that we wanted to be close to a big city. So we're about an hour away from Barcelona. And that was deliberate and really important because, you know, we like going to restaurants. We like going to shows, to the cinema, to galleries, and this kind of thing. And I think it would have been a bit much. It would have been a bit oppressive, a bit limiting if we just didn't have any way of doing that stuff. But the thing is we found living here, we can dip into the city when we want, and then the default mode is very relaxed and relaxing, which is, you know, the right way around for us.

(Joel Beasley at 00:03:23) Nice. Yeah. I live in a more rural area, and then there's a big city about an hour away. So when we want the big city stuff, we go in there. And when we want it to be more quiet, we just kind of hang out around where we live. But it's not like the micro village concept because our producer Jake had been out there last year for vacation, and so he pulled up pictures and was showing us all about it. And I thought it was cool because around 200 people, that's really close to the Dunbar number. You know? So you can really know the people in your village.

(James Brady at 00:03:52) Our tribe.

(Joel Beasley at 00:03:57) Yeah.

(James Brady at 00:03:57) Yeah.

(Joel Beasley at 00:03:58) Okay. So you want to hear a mystery we're trying to figure out here?

(James Brady at 00:04:02) Oh, that sounds interesting.

(Joel Beasley at 00:04:03) Yeah. You know the answer too. Because all right. In your LinkedIn profile, it ends with forward slash GoodGravy. Now we were talking about this in the meeting trying to figure out what this was, so we took bets. Right? I thought it was a Slack GIF thing that it would be really funny if you do Giphy on Slack that it would have this amazing meme for good gravy, but it couldn't match anything. Got no results.

(James Brady at 00:04:26) Okay.

(Joel Beasley at 00:04:27) Adam thinks it's because it rhymes with your name, James Brady, good gravy. And then Jake thinks it's because you like biscuits and gravy. So which one is it?

(James Brady at 00:04:37) Well, I don't know if I should tell you. I mean, it's not racy or anything. I just I'd like to have something of an air of mystery around me. I didn't even realize it was generating this air of mystery.

(Joel Beasley at 00:04:47) It was buzz. Yeah. It was on the homepage of People.com today.

(James Brady at 00:04:52) Exactly. Everyone's talking about good gravy and no one knows why. No. So I will tell you. It is partly, I think it was Adam's guess that it rhymes with my name? It's partly that. Yeah. It's also something of a not very often heard, but something of a phrase in the north of England, which is where I'm originally from. And it's kind of like, good gracious. You'd say good gravy as a sort of, you know, I don't believe that, you've taken my breath away, kind of thing. I think it was actually because I was signing up for Twitter and the handle that I normally use had already been taken, so I just kind of chose the first thing and it snowballed from there. So not quite as exciting as your guess, I'm afraid. But yeah, that's where it comes from. It's a kind of an English chatter phrase.

(Joel Beasley at 00:05:46) Oh, nice. Yeah. And so it's your Twitter handle too?

(James Brady at 00:05:49) Yeah. That's right. Although I will say that I never post or look at Twitter. So...

(Joel Beasley at 00:05:54) But what about when you're at conferences? You do it then? Like, if you're at a conference, do you Twitter? Because they want you to. They post the signs everywhere.

(James Brady at 00:06:03) I know. I know. No. I, so I actually, the most I was at re:Invent towards the end of last year, and yeah, I didn't tweet. So no. I know I'm not, I feel kind of, the reason I'm all kind of umming and huffing and puffing is that I do think that I probably should, given my role and trying to build a profile and all that kind of stuff. I just I'm really conflicted about other aspects of social media, which I can get into, but maybe isn't sort of CTO focused.

(Joel Beasley at 00:06:38) Yeah. No. I completely, what I do is I have a team, right? And because I try to stay off social media as much as possible and try to connect with myself and get, I found out that I happen to need, as an individual, my needs for quiet alone decompressing time are pretty high. Like, I like to spend a lot of time alone. If I don't get my alone time, I feel awkward and burnt out. So, you know, that affects everything from your relationship with your spouse to, it's just something that you have to be aware of, right?

(James Brady at 00:07:11) Yeah. Yeah. That's true. Did that realization line up with you moving to your current more rural setting?

(Joel Beasley at 00:07:18) No. I was actually born in this place where I live right now.

(James Brady at 00:07:22) Oh, really? Yeah. Okay. Okay. Yep. Yeah. Because I think for me, it definitely did. I don't know if it's correlation or cause, but definitely that kind of different pace of life thing that I mentioned is more than just the how much traffic there is in the street or something. It really kind of feeds into a slightly different take on what one's life is about. And, you know, there just isn't that much point in doing loads of tweeting in a tiny village where no one speaks English. But just kind of enjoying the kinds of things you were talking about and, you know, a bit of self-reflection and going for a walk with the dog and a bike ride has sort of filled the space that maybe Twitter used to take up for me a little bit.

(Joel Beasley at 00:08:10) Yeah. I definitely had to figure out how to self-regulate in the sense that, yeah, I can make myself as busy as I want to be even though I live in a rural area, right? And so I guess the theme for me for the past five years is figuring out what is true over longer iterations of time, right? Because you get a shorter iteration of time and you can get real excited, want to go, go, go. But then you notice that as you go through these cycles, as you cycle through years, that you just learn how to live a little bit better, right?

(James Brady at 00:08:44) Do you think there's any value in those high frequency cycles? Like, has one of them turned out to be actually this has unlocked some new passion for me, for example?

(Joel Beasley at 00:08:56) Yeah. So I think that humans are pretty good with intense activity and then rest. That tends to be the thing. I've put my schedule to where it's fixed. Like, it's exactly the same thing every day. And then, and then I've changed it to be, because I found that monotonous pretty quickly and boring, and I just didn't like it. So what I do right now is I do six-week sprints with myself. So and then I'll take three or four weeks off, and I'll do six weeks, and then three or four weeks, and then six weeks. And so I'll go to the gym every single day for six weeks, and then in the non six weeks, when I'm off, I'll go four times a week instead of seven days a week, right? So I go back and forth...

(James Brady at 00:09:42) On your time off.

(Joel Beasley at 00:09:44) I go back and forth between difficult and extremely difficult.

(James Brady at 00:09:48) Okay. Okay. I see. I should try that. Yeah. I mean, I never go to the gym, so I feel like I'm letting the side down here. But that's interesting. So it seems like maybe, so do you find yourself doing the same stuff within that six-week sprint and then the time off? And just switching between the two different modes is enough variety to kind of keep your brain interested?

(Joel Beasley at 00:10:14) Yes. Switching between the intensity is enough variety to keep me interested in the long term. On the short term, they are different. So every single one of those days I'm at the gym is a different workout. It's not the same workout. So seven days, seven different workouts. So there's, you know, by the eighth day, I'm doing that first workout again. So I haven't done this exercise in eight days, right?

(James Brady at 00:10:36) Yeah. Yeah.

(Joel Beasley at 00:10:36) So there's variety there. And then I also, I'm always testing new ideas and new concepts. Like, some days I play this game where I'm like, all right, I'm just gonna focus on what's the one thing I can do today to win today, right? And so then I put all my focus around that and, you know, I just, I have to keep it interesting with myself, playing the game of life.

(James Brady at 00:11:00) Yeah. There was a, there was a time, it was in 2015 when Keith Rabois, who you may have, he's an investor, and he was COO, I believe, at Square before that. Anyway, he was an investor in Teespring where I currently work. He came in to give a bit of a kind of management advice, I suppose you could call it. And one thing that really stuck with me there was he was talking about as a team scales, you should be able to take more risks because you place more bets. What he warned against was that if you have a kind of stack rank of things from really easy sort of one-liner things right at the bottom, there's a middle band which are challenging, but you kind of know how to do them, and then the stuff at the top, which is terrifying and you'll probably fail, but if it works, it'll be transformative. It's very easy to fall into that middle band. You think I'm making progress, I'm doing hard things, I'm not doing all the gimmes. But if you scale that up over a team of 10, 20, 50, 100, 500 people, no one is doing the big swing stuff. And what you actually should be doing is having 200 people there just doing insanely difficult things that'll probably never work because the 10 folks that'll actually succeed, the tide will raise all the ships, and it'll work out better for everyone in the end. Which, and the reason I mentioned that, that really sounds a lot like what you, you know, the kind of one thing today sort of deal. It's really easy to look at your to-do list and check off six things, including the one which is make sure my calendar's up to date. You know? You get as much of a dopamine rush from taking that one off as you would from the really big kind of write up this kind of architectural road map or something. Whereas what we probably should do as leaders especially is, you know, take those big swings and tackle that stuff head on because it's kind of on us to do that. You know? It's really tough for someone with a bit less agency to take that freedom, take that independence.

(Joel Beasley at 00:13:08) Yeah. It's interesting because we have to be more vocal about the fact that they're allowed to fail, because especially as it gets a bigger group, because people, they don't want to. So it's not enough to just say you want to and put it in your corporate values. You have to constantly encourage it and promote it. So how did you get involved with Teespring?

(James Brady at 00:13:32) Yeah. So I've been with Teespring since 2015, beginning of 2015. And what happened before that was I was running a startup with a friend of mine for a number of years, for five or six years, and we both felt that our learning had not flattened off completely, but I would never claim that, especially in a startup. But we weren't really quite as challenged as we had been before. We were looking to join a larger company, learn from some people that had done more things. It was basically our first job. So we moved the whole team, the startup team, to join Square at that point. And what we found there was, for me personally, anyway, was it was a much larger organization. It was hundreds and hundreds and hundreds of people. And, you know, we had some agency in that we were running our own kind of area of the company, building our own product with our own processes and own code base and all the rest of it, and our own team. But what I learned there, what I learned at Square was that I learn best through trial and error. And a key part of trial and error is that you need a fast feedback loop. You need to be able to try something, and then the quicker you can learn from that, the more that you learn in total over time. And that was really tough at Square just because, you know, it's a financial company, so we have to be quite careful, and it's got very kind of rigid design guidelines and just a larger organization. So the reason I joined Teespring, to actually answer your question, was they seem to be in a sort of a sort of Goldilocks point where it was smaller than the startup I built, but it was a lot...

(James Brady at 00:15:15) It was larger than the startup I built, but it was obviously a lot smaller than Square. And it seemed like somewhere where I could operate at a higher level than just kind of individual line management, but also really try something out. Throw the wheel this way or that way and see if it works, see what happens, rather than six months later at Square. Like, maybe it would work or maybe it wouldn't, but there's so many other different confounding factors. It was quite hard to learn from that. So that's why I initially joined them in 2015, and I've—that was in San Francisco.

(James Brady at 00:15:47) And then over the years, I've changed locations a couple of times to London and then here to Spain. And yeah, sort of risen through the engineering team and currently the VP of Technology there.

(Joel Beasley at 00:16:00) So are they doing things like you mentioned? Like, are there teams that are focused on just making big swings there at Teespring?

(James Brady at 00:16:09) There are. I think we could formalize that better, and it's something we've been talking about recently. So I came across—there was a really useful model for this I came across recently that I'm thinking about rolling out, which is mentioned in Sense and Respond, the book Sense and Respond, which is really excellent. And I think it's maybe a model from McKinsey. They talk about three horizons—Horizon One, Two, and Three, where I'm trying to get this—we should run it. I think Horizon One is the kind of money-making day-to-day core business stuff that you're trying to tweak and optimize. Horizon Two is we've validated the user need, but there's still some more investigation to be done. We're still finding product-market fit, basically. And Horizon Three—I think I've got this the right way around, the One, Two, and Three—is we have no idea. We know this—we don't know if there's any going to be any users.

(James Brady at 00:17:08) We have no idea how much they would pay. It really is, you know, embers in a fire. So yeah, we definitely have a number of teams that are working on the bread and butter, the core stuff. I'd say looking at the teams, we've got some Horizon Two. And we've got one team who just recently launched digital products on our platform. So we're really kind of taking a bold move away from our traditional business model and very much into this kind of virtual digital marketplace kind of idea. I would say that is one of these kind of bold bets where we had some kind of indication that there was a market there. There was some people kind of working around, like hacking our system and other systems to make this work, which is always really, really interesting when you see that from users. Right? And so we decided to formalize it and make it into a team.

(James Brady at 00:18:02) And yeah, they just launched—I think it was publicly launched a week or two ago.

(Joel Beasley at 00:18:08) Oh, that's pretty cool. So you could sell digital goods now?

(James Brady at 00:18:10) Yeah. So, you know, initially we are thinking about and our creators are working with things like filters you can download. If you're following someone on Instagram, you can download the filters that they use. There's people that have been selling ebooks, like coloring books for their kids to keep them occupied during the quarantine. There are people selling sewing patterns, knitting patterns, that kind of thing. But, you know, if you look at the full scope of what that could be, it's—you know, we're really just kind of nibbling around the edge here. It's—there's a lot of scope that we're kind of rapidly going after that. I can't go into full detail, but yeah, we've got kind of big goals for that area.

(Joel Beasley at 00:18:58) So I was actually on Teespring's website when I got the Slack message that you were coming on the show. I was like, no way. I was like, this is exciting because we decided to—like, we just recently built out the studio, like made it official versus me just being at, like, the office computer.

(James Brady at 00:19:17) I've got to say, you've got a really nice background.

(Joel Beasley at 00:19:19) Thank you. That's a fake wall. It's foam.

(James Brady at 00:19:21) Don't tell me this.

(Joel Beasley at 00:19:23) I know. I know. I'm not supposed to do that. They're like, don't do it. Don't do it. I'm like, it's a fake wall. It looks—it's so good, though. Shout out to Jake for that. Like, so it's a foam board. He built this custom wood base, but then there's this wood wallpaper stuff added to the foam board.

(James Brady at 00:19:41) If you kind of leaned violently in the wrong direction, it would just kind of crumple into a heap.

(Joel Beasley at 00:19:48) No. It's actually very sturdy. Very sturdy.

(James Brady at 00:19:51) Oh, yeah. Foam. Okay.

(Joel Beasley at 00:19:52) Yeah. Jake's a good contractor-type person. So yeah, he made it really good, and then my wife painted the wall. This is called Space Black.

(James Brady at 00:20:00) Oh, nice. Okay.

(Joel Beasley at 00:20:02) Makes the logo pop. But what we were doing—where we are going to get, like, hats and mugs and t-shirts. And the most important thing to me—here's the most frustrating thing on the planet. So I go on Amazon and try to buy—like, see a cool shirt and it comes and then the shirt's like, it's got the logo on it, but it's like a crappy shirt. It's, like, not a good shirt. Right? And so I don't want to wear it or it doesn't fit right or whatever. So I wanted, like, really high quality. So I started Googling around for, like, what t-shirt companies have the highest quality base.

(Joel Beasley at 00:20:34) The base—I can just put something on. And I came across your site and the UI was just so beautiful and you guys had good reviews. And so I said, okay, let's order some stuff. Like, let's make sure this—it's hard because not every provider out there—it's weird because providers will specialize in one thing and do it very, very well. Right? But then we need five things. Right? And so we're going to have to piecemeal together different providers because we want, like, mugs, hats, like all this different stuff.

(Joel Beasley at 00:21:03) But we came to the conclusion that there's not going to be one provider that gives us everything, but right now we're designing a shirt to be ordered through Teespring, so we're really excited about that.

(James Brady at 00:21:14) Okay. Well, we should talk. I'm not sure what other kinds of products you'd be interested in, but there's some which are, you know, reserved for maybe sort of more established users on the platform that you can design and sell through us. And yeah, if they match what you're looking for, I'd be happy to open that up for you. But I think what you mentioned—a really interesting point there—I thought you were going this direction of needing to kind of piece together lots of different things to bring it all together to kind of actually deliver the thing that you want in the end.

(James Brady at 00:21:51) That's something that we care a lot about, and we think it's something which is really going to be—it is and will be even more so—our kind of key differentiating factor from us versus other competitors in the space. In that, we aim to have a turnkey top-to-bottom experience which fuses the designing process at the beginning, the e-commerce experience that buyers are interacting with, plus all of the fulfillment supply chain as well. And we take that very, very seriously. And, you know, if you order something, especially in the US, that is more than likely going to be coming from an actual warehouse which we own with our staff who are doing the QC.

(James Brady at 00:22:40) And we kind of own that whole process from start to finish. And that means a few things. Firstly, it means that in terms of the user experience, just the pieces are more joined together. You can cobble together stuff to create a sort of a SaaS version of this user experience, but because we own it all from beginning to end, that just kind of happens naturally more or less. And the second thing is to do with quality. And it is—we don't have competing incentives here. Because everything is joined together, it's not that the person who's making the mug or the hat or embroidering the bag or printing the sticker or whatever it is—that person isn't incentivized to just do something kind of crappy and get it out the door. Because in the end, they are, you know, through a few steps of separation, they're getting paid by the users' sales activities and the users becoming repeat customers and all that kind of stuff. So in the end, we want for you as a creator to have the best possible experience and for your fans as well, which means that in the end, our quality is only going to improve rather than this being this kind of slight dissonance, impedance mismatch, misaligned incentives kind of thing if the e-commerce experience is not run by the same folks who are actually making and delivering the thing in the end.

(Joel Beasley at 00:24:05) Yeah. Can I tell you what our, like, perfect-world scenario is?

(James Brady at 00:24:09) That would be really useful. Yeah. Okay. So I'm writing this down.

(Joel Beasley at 00:24:12) The idea came up because I had this company called X-Team on the podcast, and they're an engineering company. And the guy—the CEO—was wearing this, like, really cool shirt. It was like this face of a tiger or something. And but it was custom done with art. And so I said, that's so cool. He said, I can send you one. He's like, they're private. It's internal only for our team, but I can send you one. I said, okay. After the call, he sent me a link. And I clicked on the link and it was just like, here's your gift, you know, here's the shirt, select your size, and then enter your address and it'll—and then I got the shipping thing. So he gave me something, but I got to configure it a little bit.

(James Brady at 00:24:49) Okay. Configure, like, size and—

(Joel Beasley at 00:24:52) Just size.

(James Brady at 00:24:53) Just size.

(Joel Beasley at 00:24:54) It was just strictly size. It was just like small, medium, large, extra large. Right?

(James Brady at 00:24:58) Yeah.

(Joel Beasley at 00:24:58) So I go, okay. So I got to pick my size. But the reason is because we wanted to do these, like, boxes—like swag boxes for guests. Right? But we don't want to limit it to just things that are indifferent to size, like a mug or a wristband or a sticker. We wanted to have, like, you know—they could pick a tumbler in there or a mug and, like, then they could pick the size of their shirt. Like, maybe two or three things that aren't size-related, and then they could pick the size of their shirt, and then they get this little branded swag box. It goes to whatever address they choose. We're not sending emails back and forth, going through their PR people. You know, hey, can you give me Kevin's address? You know, all this stuff, and where does he want it sent? And it's just after the show, I just give them a link, and it's their custom swag box. They configure it, enter in their information, then it shows up where they want it to with their tracking number.

(James Brady at 00:25:45) That's a really good idea. I don't think we'd considered that one.

(Joel Beasley at 00:25:50) I haven't found anyone that does it the way—like that.

(James Brady at 00:25:55) Okay. I'm going to take that and claim it as my own. Nobody's listening to this. Right? I can just say it's my idea.

(Joel Beasley at 00:25:59) Zero. Yeah. That's so funny. So another thing that I noticed too that bonded me instantly with you was this concept of atomic habits. So one day in my life, I'm going through it. Somebody sends, like, a YouTube video to me of, I think, his name is James Clear. Right? Of James giving a talk, and he gives this—I was just enthralled by it. I couldn't stop watching it. And so I buy the book, and I buy the action tracker and my habit trackers and all that. I've just—I would say the desire was there for me, because I try new things all the time. But that framework, that mental model of how habits work and how they create your future was given—articulated clearly—by this guy, James. And so I just fell in love with it. What—how has it changed your life?

(James Brady at 00:26:52) Yeah. No. I completely agree. I think it's the same—you know, I've read my fair share of self-help-type books in the past, but my issue with most of them is they tend to be quite prescriptive in terms of follow these five steps that life coaches hate, and you'll be a billionaire in a year. You know, it's such kind of one-size-fits-all kind of thing. And I agree that is much more of a kind of general framework, and here is, by the way, cited links for the sort of research for why this is how your brain works. Yeah. No. The thing which—it's a small thing, actually, but the thing which really kind of proved to me that it works—I used to bite my nails. I mean, it's such a small thing, but I bit my nails for, like, thirty-five years, which is a long time to do something on a daily or weekly basis. Right? And I was always embarrassed by it. I didn't like the way my—I didn't, you know, it looks weird. It looks horrible, and people kind of catch me doing it. I feel a bit embarrassed.

(James Brady at 00:27:58) Anyway, I put a bit of a plan in place for what to do instead of biting nails—the whole kind of cue, craving, response, reward loop that he talks about—and kind of slotted a few pieces into place. And within, I think it wasn't long—within a month, it was done and finished with and easy. And I don't know, it is the kind of thing where because I really wanted to stop doing it beforehand, it became a bit of a sort of self-fulfilling thing. Still want to get back into that place. But yeah, that was the kind of—an easy version, I suppose. One thing which we're trying to do at Teespring, and which I'm—it's actually one of these experiments I was talking about of kind of experimenting on yourself—is could the same principles apply to a group, to a team, to a department, to a company even? And what we're doing is we are saying that for every single pull request which goes into this repo—it's our oldest repo, it has the most problems with tech debt because, you know, it's been around for ages—every single time you make a change, you have to do even the tiniest little bit of tech debt cleanup.

(James Brady at 00:29:14) It can be fixing an apostrophe in a comment. It could be even sort of writing down in a Jira project, I found some tech debt over here in the repo. That's good enough. It's just more than zero. It's just kind of lodging in people's minds that there is this thing that I need to do. So we've got our prompt for that. I've got—I personally sort of congratulate people, thank people, and send out statistics for us to kind of build up the habit loop of people doing it and kind of nudge people when they're not doing it. And, again, we all suffer from tech debt. It kind of bites us all from time to time. So there's the underlying desire to fix it, which really helps. We're not kind of forcing it through. People kind of want to do it. It's just a question of how do we structure the thought process and the culture and the habits so that we have a way of kind of chipping away at it.

(Joel Beasley at 00:30:08) Yeah. I love that. Whenever I notice my discipline slacking, I just go to, like, do the smallest thing. Like, I don't want to work out that day. It's like, okay. But I have to go sit in the gym parking lot for fifteen minutes. I just have to drive my car to the gym parking lot and sit there. And then once I'm there, I'm like, ah, I'm already here. Let's just go in. Right?

(James Brady at 00:30:26) Totally.

(Joel Beasley at 00:30:27) But that little—that little lie to get that fire started is so useful.

(James Brady at 00:30:33) Yeah. And not skipping a day is one of the key things, or not skipping two in a row, right, is a kind of key thing that he touches on. Yeah. That's interesting. He, I think he gives an example of someone that even went to the gym for 15 minutes every single day and refused to work out for, like, a month or something, to the point where at the end of the month, he was just so frustrated. Like, I'm coming all this way.

(James Brady at 00:30:58) I'm changing into my gear. I'm just kind of sitting here like an idiot. I might as well do some exercise and, you know, that's how he got the ball rolling, as you said.

(Joel Beasley at 00:31:10) Yeah. No, it worked for me. I was close to 300 pounds. Like, I was really overweight.

(James Brady at 00:31:14) Really?

(Joel Beasley at 00:31:15) Yeah. Yeah. And when I was younger, I got hit by a car, and then I was in a wheelchair for, like, a year. And then, like, halfway through my rehab, I fell and then re-broke my right leg. And so that extended, like, the wheelchair-ness for another six, eight months.

(Joel Beasley at 00:31:30) And then I just got really depressed because I was active and everything before that, and I couldn't play sports, and I had to ride the short bus to school because that was, like, the one that had the wheelchair thing on it. And it, like, I just got depressed, and I didn't want to leave my room. And then I just had, like, a couple dark years. And then I came out of it, like, in high school, and I was just, like, I want to participate in life. I want to have girlfriends. I want to, like, you know, play sports. I want to, you know, get back into life. And then I, you know, lost the weight over a couple years.

(James Brady at 00:32:06) Wow. That's quite a story.

(Joel Beasley at 00:32:08) Yeah. Difficult things, man. There's always, I find whenever there's great people, there's amazing adversity in their past.

(James Brady at 00:32:14) Right. Yeah. Well, you must, I mean, it must be interesting seeing the patterns and the differences as well, doing this podcast. Right? Like, I'm sure there are some times where you're like, oh, yeah, this one again, you know, that kind of that pattern. But, uh, yeah. I don't know. I've not heard a story like that before. That's that's pretty extreme.

(Joel Beasley at 00:32:34) Yeah. I mean, and just to be real, like, there are definitely times when, you know, we're, like, over I think we've recorded over 300 or 400 episodes. We've released, like, over 200 of them. And so what happens, it'll be like, alright, this is becoming routine. Like, when we pitch topics for the show, we're like, alright, what topics are we going to talk about or what areas, you know, who is the guest? What, where are their interests? And then what areas do we want to talk about? And so we've just developed, like, production meetings and ways to make it interesting. And so now I specifically sit down and figure out, like, what am I going to be interested to talk about over the next couple months, and then who's, like, an expert there.

(Joel Beasley at 00:33:15) Like, we had this cool guy on, Rafael Duran. So he was the creator of a documentary called The Cyborgs Among Us, which is on Amazon Prime. And it's all of these people all over the world that are, like, injecting electronics into their bodies and turning themselves into cyborgs. It's pretty cool. Yeah.

(James Brady at 00:33:32) I've not heard that one.

(Joel Beasley at 00:33:33) Yeah. It's pretty neat.

(James Brady at 00:33:34) That sounds fascinating.

(Joel Beasley at 00:33:35) Yeah. And he's in Barcelona too. He's really

(James Brady at 00:33:38) Yeah. Okay.

(Joel Beasley at 00:33:40) He's a really cool guy. Yeah.

(James Brady at 00:33:42) Yeah. I'll I'll try and reach out to him. I mean, I'm always looking to build my network, especially here. Yeah. Especially with cyborgs. That sounds, yeah.

(Joel Beasley at 00:33:52) It really is because there's, like, the medical world that's pushing it forward, so he covers that a little bit. And then he covers the underground world where, like, when the people need to inject themselves and stuff, they go to, like, tattoo parlors. They do it, like, under the table type deal. It was all very fascinating. But before I forget, when we were talking about, like, media production and all of that with social media, so this might be useful for you. So I try not to be on social media, like, addicted to it because I did that for years and it just yielded negative results. Right?

(James Brady at 00:34:22) Hmm.

(Joel Beasley at 00:34:22) All that time. And so the way I've scheduled it is we have, like, a team of people that'll post, but we decide the content ahead of time. So we will decide the content in the meeting. So they're still my thoughts, my ideas, like, all of these, like, you know, as a team, we come up with the best content and everything to post. But then the actual labor, act of posting it is not done by me. So I'm not sitting there waiting for videos to upload and then getting distracted and commenting. And then what I do to keep, like, for me is I just will schedule, like, an hour one day a week, and I'll go in and I'll check all my notifications. I'll respond to the messages. People send me messages from the show all the time.

(James Brady at 00:35:05) Right.

(Joel Beasley at 00:35:06) And I love it. Right? Just makes my day. But so I use a team to help me, but I'm still getting my thoughts out there. And so that's something you could probably copy with, like, a social media team member, or you could have them, like, set up a schedule for you, put thoughts out if you're interested in that.

(James Brady at 00:35:24) Yeah. For sure. I mean, look, I, as I said, I definitely see the value in it. It's the cost-value trade-off that seems a little bit murky to me. But, yeah, being able to kind of manage the costs in the way that you said sounds really interesting. I think a bunch of kind of more, even more celebrities than you, Joel, are kind of, you know, right, only in terms of Twitter. You know, that they'll send a tweet out and and that's it. They just don't really ever look at comments because

(Joel Beasley at 00:35:57) They're crazy.

(James Brady at 00:35:59) Like, yeah, I'm sure they are for some people. And once you get to a certain level, there must just be so much that you couldn't process it anyway. You know? It's sort of it's always going to be lossy at that point. Anyway, yeah, that's definitely not a problem for me and my 34 followers.

(Joel Beasley at 00:36:17) Yeah.

(James Brady at 00:36:18) I'm just looking for excuses at this point, I think.

(Joel Beasley at 00:36:20) No. We don't have a huge following online either. So, like, I mean, people when they're doing the podcasting, they're running, they're at the gym, they're working, they're in the car, they're on the train, you know. And so I don't follow, like, my favorite radio station on, you know, LinkedIn. Right?

(James Brady at 00:36:40) Yeah. That would be odd. I could put it that way.

(Joel Beasley at 00:36:42) Yeah. So it's it's always fun. But, you know, we we try. We do the the best we can. And and it's all, like, this learning process of what we like, what we don't like, what works, and then ultimately, you know, we have to see how it fits into the business model. Like, our model is bringing value to the listeners. Like, that's our model. And so we have to look at everything through the lens of does this add value to listeners' lives?

(James Brady at 00:37:08) So do you, is the way that you use social media there as a feedback mechanism and, you know, if the listeners are saying this is great, you should do more of this kind of thing or, you know, this question was killer or something. Is that what you're looking to get from it, or is it more that's that's a way you can tell people, hey, there's a new episode of the podcast up and and sort of prompt them to go and download it and enjoy it.

(Joel Beasley at 00:37:32) Yeah. So it's a couple things. So the thing that I care about is knowing what people want to hear about. So I send out emails to people. Like, I literally pick 100 new people a week, like, 100 new CTOs, and just send them a cold email and say, hey, here's some interviews I have coming up. I need some inspiration on some questions. And then we have a newsletter. So between the newsletter and, like, polling and then the cold outreach, we have a really good mix of, like, what people want to hear about. And it's it's interesting because none of them are connected, but the topics all move together.

(Joel Beasley at 00:38:07) So at different times of the year. So we do that. But then we also, like, most of the content we post is clips of, you know, insight or advice from our listeners. Right? So we put that out there. Here's some sound bites, some good things to think about, some quality leadership insight. That's why a lot of people like the newsletter and then follow us on LinkedIn. And then we put a bumper at the end of the episode that says, you know, reach out to me on LinkedIn and say hello. And and then I always engage with them and ask them what they want to hear about. And that's actually my job.

(Joel Beasley at 00:38:42) So that goes into my hour of of social media a week. But then we actually go over everything from whether it's from newsletter responses, from the cold outreach, from, you know, that process I just described about the podcast outro. And we we write everyone's first name and last initial down and then their questions, and we we blend that into our prep. And we don't, like, it would be weird if every five minutes I was like, shout out to so-and-so for the inspiration for that question. Right?

(James Brady at 00:39:14) Yeah. Well, as long

(Joel Beasley at 00:39:15) But we get it.

(James Brady at 00:39:15) Yeah. As long as you're kind of covering the topic and and getting insights on it, that's, I'm sure people actually want to hear the answers rather than hearing their name in the podcast. I hope so anyway.

(Joel Beasley at 00:39:25) Yes. Well, actually, it's pretty surprising. Most people don't want their name mentioned and they always have this interesting

(James Brady at 00:39:31) Even beyond that.

(Joel Beasley at 00:39:32) Interesting reason. I know. People are pretty shy about that stuff. They're like, oh, like, there's always, like, a story. Like, I don't want my coworkers to know, or, I'm like, that's so weird, but I get it. Some people just want their privacy, and I'm pro-privacy, so I get it.

(James Brady at 00:39:47) I guess if it's a really basic question, like, I don't want people to, I don't want to admit that I don't know how to be a manager given I've been a manager for 10 years or something. You know? But, yeah, I mean, all the all the more important to ask those questions if you're not sure or if you're looking for a different perspective.

(Joel Beasley at 00:40:02) Have you ever dealt with that, somebody who's been a manager for 10 years and they they don't know how to ask for help?

(James Brady at 00:40:08) Gosh. Don't know how to ask for help. So, yeah. Yeah. So my, I kind of skipped over a slightly boring gray chapter when I was describing my my professional. I worked for IBM for two years in the UK as a software engineer, but, yeah, I I I don't know quite how they decided how to arrive at who was going to be a manager there, but, I don't know. It it wasn't the people that had an issue. It was the the whole kind of ossified structure of how the of how the company worked meant that there was a lot of kind of following inherited wisdom about how teams should be run, products should be developed, management should happen in general. So and and, you know, questioning feedback loops, trying new things was was anathema inside of IBM. So I think I think the organization kind of set those folks up to not value that kind of self-reflection.

(James Brady at 00:41:12) Right? Like, they they somewhat thought they had all the answers because, you know, they had been such this such a huge player in the industry for for so, so, so long that it it wasn't really looking, at least in the area I was working in, it wasn't looking for, like, fresh new ideas and sort of, maybe we should try something crazy here. So it's sort of leaders, which which probably held some people back.

(Joel Beasley at 00:41:35) Yeah. Well, they they also had the disadvantage of they existed during the era of command and control was the management style.

(James Brady at 00:41:45) Right.

(Joel Beasley at 00:41:46) And so you have this huge ship that's got a 20-year history of this being the way, and, like, let's rank people and all this stuff. And all these different weird, you know, 1980s, early 2000s management styles where we're trying to get it right as a people. Right? And so then they have all of that culture rolling into this new future where that culture is the opposite of what works and what we have found to be really, really useful. You want this decentralized, empowered, intelligent culture that can take a scientific, literally science, scientific method approach to everything from features to business models to

(James Brady at 00:42:25) Yeah. That's right. And there was there was definitely people bringing those ideas into IBM at the time, including in, Hursley, which is where I was where I was working. But it was, they were, you know, they were literally in a different building and and sort of, yeah, they they were doing something quite odd according to everyone else where it was it was just agile. You know? It was it was, like, fairly established at that place. It's 2006, 2007. Right? So it's not like it was a spring chicken as a as an idea. And, by the way, so you mentioned 20 years there.

(James Brady at 00:42:56) The the product that I was working on, that if you were working there for 20 years, they would have done a major release of the product 13 times during that length, during that spell of 20 years, which in terms of, you know, what I mentioned before, if you're in terms of feedback looping, place of of of learning from what you've done, that's tough. You know, that's half of your career, and you've done something 13 times. It's it's really hard to get good in that in that way.

(Joel Beasley at 00:43:25) And now we ship daily.

(James Brady at 00:43:27) Exactly. Multiple times a

(Joel Beasley at 00:43:28) day. Yeah.

(James Brady at 00:43:29) Yeah. Yeah. Absolutely.

(Joel Beasley at 00:43:31) So you have an awesome blog. Right? I was I was a fan. We went over, like, the content and everything, and, you know, it's always it's always interesting. I find that the people who have blogs and have content and ideas that they've taken the time to articulate and write down in detail, it always makes the prep and the conversation, like, so much smoother. But I was curious to you and your career because I'm always encouraging people to write. Like, if you don't know what to write about, start writing about that. Right?

(James Brady at 00:44:03) Oh, that's a good one. I like that.

(Joel Beasley at 00:44:04) Yeah. And then, I didn't come up with it. I just, you know, heard it somewhere. But and then the other one from Gary V, which I like a lot is, document don't create. So don't feel like you have to go create this huge beautiful blog post on this idea and be this thought leader. Instead, just, like, document what's going on in your learning, your current learnings, consistently. But I want to know, like, directly from you, like, has writing helped in your career?

(James Brady at 00:44:33) I think it definitely has. I don't think it has in some of the direct ways that it no doubt has for other people. So, you know, I'd I write the blog primarily for me is to remember. I find the actual act of writing incredibly valuable of, like, ordering my thoughts. If I'm having a conversation with someone and I can link them to it, it kind of short circuits maybe a lot of back and forth to continue the conversation, not to shut it not to shut it down, to be clear.

(Joel Beasley at 00:45:04) That's a good distinction too.

(James Brady at 00:45:06) Yeah.

(Joel Beasley at 00:45:06) Because it's funny because my mind actually went to shut it down. Like, my default, I was like,

(James Brady at 00:45:11) Oh, I didn't realize that's how it sounded. I was like, oh, no. No. No. But, yeah, you know, if if I've, that can kind of help move things along along a little bit maybe. But, you know, for for some for some people, you know,

(Joel Beasley at 00:45:23) you know,

(James Brady at 00:45:23) Like Gary V, for example, right? He, no doubt, blogging and social media has completely opened up a ton of different things for him because he's so prolific and because he's got a wide range of interests, and he writes really well also. I don't really view it that way, but I think there's a definite strong second-order effect, which is just I feel more capable as a technology person from having forced myself really to write things down and think carefully about, you know, what is right and what's wrong and what do I think is important. And yeah, that's kind of helped me make career decisions.

(James Brady at 00:46:03) It's helped me decide, you know, how I learn best. It's helped me kind of focus on particular technologies or mental models or whatever it is. I think I probably, like, the Atomic Habits thing might be a good example here. I might well have stopped at, "Oh, I've stopped biting my nails. That's nice." I actually, kind of writing down a couple of—I did a couple of blog posts on Atomic Habits and, like, you know, ways we're using them at work and then a sort of layer on top, which I personally found useful. That kind of encouraged me to keep going and sort of see some benefits and effects in other areas as well. So yeah, I put a lot more effort into blogging than I do into social media. I feel like, you know, I think for some people, really condensing something down into a great, pithy tweet can take a huge amount of effort and work and skill.

(James Brady at 00:47:02) But yeah, I find for what I get from blogging, I just find it more useful. It's not about reducing something to 140 or 280 characters. It's about fleshing out a thought and then maybe condensing it down a bit. But yeah, no, I definitely recommend it for anyone, you know, whether you're a manager or sort of on the technology track or senior or junior or whatever. If nothing else, coming back to it in the future and realizing that you had already thought about something or, "Wait, I've read that book, but I can't remember what the takeaways were." That sort of lazy memory thing, or outsourced memory thing, is not to be sniffed at either.

(Joel Beasley at 00:47:46) It's also about, like, back to your comment on posting on social media and putting effort into the thought that you're going to push out into the world. It's also audience. So when I'm writing my investor updates, I know there's a bunch of people that have money invested in me. They're going to read every line of that, right? So it's going to be articulate. It's going to be designed to give them the information they want upfront, but then also drill down deeper. You know, it's just like the care and the craft of writing that update every month. I try to keep it one full page and update them on everything in the business, and I do that every month.

(Joel Beasley at 00:48:22) And I approach it like I write a first draft, then I do a second draft edit. And I've gotten a lot better at writing after doing the book and everything. So I've just condensed that process of multiple drafts down a little bit. But then I send it to a third person to read and then make any final edits or grammar things, and then I send it out. But that process is a very different process than when we're drafting a LinkedIn post.

(James Brady at 00:48:54) Right. Yeah. But it's interesting that it sounds like the process you go through is very much like writing a book, right? Like, you kind of have these ideas flying around in your head. You do a couple of drafts. You use an editor, potentially a copy editor as well. It's that process, but kind of miniaturized and happening every single month. I don't know if—I'm sure if you are Bill Gates, that is the process you go through for writing LinkedIn posts or really anything, probably. But yeah, I think the act of going through the drafting and then having someone look at it and say, "Oh, you know, you've misspelled this word," or "This punctuation's wrong," or "This isn't clear"—that in itself is super useful, right? I would assume that now, having done that many, many times, with the trial and error piece, you need less from the editor, and the drafting goes more quickly and that kind of thing.

(James Brady at 00:49:56) And you kind of lose out on that practice if you just have a thought, blurt it out, post it up, go about your day. You don't really go through that kind of mental process of, "What is it? What is the essence of what I'm trying to say here? And what's the best way of describing it? And can I draw a diagram to explain it better?" And that in itself, just getting it down clearly in your mind on the screen, on paper, is what I find most valuable.

(Joel Beasley at 00:50:23) Yeah. It's like asking good questions, right? You just have to constantly refine what that question is because it's just so important, right? Like, if you get a good question and you spend some time—I actually have a little process or technique that I use for engineering great questions, right?

(James Brady at 00:50:42) Okay.

(Joel Beasley at 00:50:42) And so when I'm working on a project and my favorite great question is, "What's the one thing that I can do today that'll push my business forward in a meaningful way?" And what it does is by asking that question—think of it like, you're an engineer, right? Think of it as some sort of filter or scope, right? It scopes out all the nonsense that your brain would iterate through and only is going to return—I mean, you know, if we wake up one day and we find out that we are just computers and we're in some sort of infinite loop or we go from organic to non-organic back to organic, I would not be surprised. Because if anything, I've found that I very much operate like a computer. The language and the questions I submit to myself are equal to the responses, right? Like, the quality of the questions equals the responses.

(Joel Beasley at 00:51:29) So it's so fascinating how we work as people. You think a lot about this type of stuff, don't you?

(James Brady at 00:51:38) Yeah. Well, yes. I think I was just wondering whether or not that's the kind of common pattern that everyone would agree with, the way that you sort of phrase your thought process and the way that you phrase the kind of mechanism of your mind. Because obviously you and I think that way. I don't know if everyone does, and I think there's plenty of room for people that don't think that way and want to just kind of have a wild idea and run with it and see what happens. And, you know, they're probably not going to be as effective as an accountant, but maybe they'd be a fantastic artist or something like that. My—one of the reasons I do think about this quite a lot is my wife's an author, and she runs an artist's residency from our house here. So we get a lot of people coming through staying with us. Obviously not at the moment, unfortunately, but in past years. And that's really—you know, my kind of, as you might expect, my social network in San Francisco was fairly homogeneous, and, you know, there was a lot of white dudes and a lot of techies. And that, I think, in retrospect, is an issue.

(James Brady at 00:53:00) You know, being able to see that not everyone thinks in the same way and that there is a kind of huge range of neurodiversity and thought patterns and there's a great amount of value in those different things is really important. And I think it kind of, in a way, it hooks into, in a very real way, it hooks into how I think about hiring as well—who we want to bring into the team. It's quite easy to think up exam questions or tests or whatever your interview process looks like, which you know you're good at. And you think it's a hard question, but you think you'd be good at doing it. I think that's quite a kind of common pattern from what I've seen. And that, you know, in a way, that sort of reduces the chance of someone that just thinks in a different way but could be a fantastic addition to the team. It reduces their chance of joining you. And if you do that too much for too long, then you end up with a monoculture, kind of blinkered thinking, just because everyone is more similar than they are different. So obviously, kind of diversity in terms of underrepresented groups is super important for a host of different reasons.

(James Brady at 00:54:17) But in addition to that, just people that have different perspectives and come from different backgrounds and would be able to think in a different way, I think, are also really important and for some of the same reasons, but for some different reasons as well.

(Joel Beasley at 00:54:32) Yeah. I mean, I'm a huge fan of diversity of thought. I was actually talking to my wife the other night. She went and was doing this Enneagram test. I think that's how you say it. So she was sharing her results and, you know, so I was reading about it and then she was having me take the exam. So I was learning about the validity of it because it was the first time I heard about it. So, like, what is this? What's its origin? And then so I was just going through that.

(Joel Beasley at 00:55:02) And what it opened my mind to is—well, I would say reopened my mind because it's just something that I do from time to time. Like, you know, that awe of looking into the sky and seeing the Milky Way and realizing we're so small and insignificant. But you can't do that every day, right? Like, there has to be time between these experiences. So it was one of those beautiful moments. I was like, "Oh, this is great. This is actually classifications for different types of neural patterns," as you said. And so it was just interesting to me because I've always been really into getting different people's style of thinking because it's so boring if somebody thinks like me. I don't even need to ask them what their opinion is, right?

(James Brady at 00:55:44) Yeah. Well, I mean, doing a podcast must be a great way of doing that, right?

(Joel Beasley at 00:55:48) Yes.

(James Brady at 00:55:49) Yeah. I hadn't heard of this one, Enneagram.

(Joel Beasley at 00:55:54) Yeah. Apparently it's pretty popular.

(James Brady at 00:55:57) Okay. Yeah. So it seems like maybe this maybe this fads and fashions, kind of changing fashions, because it used to be that Myers-Briggs was the one, right, like 20 years ago. And then I believe there's the Five—what's it called? The Five Traits personality test as well, which I think they use in sociology. But this is—I don't know. I think taking a range of different tests and seeing if they line up probably seems like a helpful thing as well to sort of cross-reference.

(Joel Beasley at 00:56:27) That's exactly what I would do. Just take all the different tests and then see what happens. But then there's also, you know, I would say this was a useful exercise of figuring out, or just reminding myself about, the different styles of how people think. Because I'm around myself so much and I interact with myself at such a large volume that I just have to remind myself from time to time that not everybody thinks like me or not everyone's as excited as me about different things, right?

(James Brady at 00:57:02) Yeah. No, totally. I think, like, one of the ways this comes out is—I mean, it is a cliche of how you kind of need to explain things multiple times or kind of walk through an explanation multiple times before it really hits home because it's so clear in your mind because you've done the thinking, you've written the blog post, you've done the investor update, whatever it might be. But yeah, you sort of assume that everyone's in the same frame of mind. They've got the same—they've done the same amount of thinking in the run-up to it. So, you know, even if you have the same personality type or pattern of thinking, you still need to take into account the frame of someone's mind and what context they're coming from as well when explaining stuff or trying to explore a topic with them, that kind of thing. It's—yeah. Who was it that—it was someone at Square who kind of recommended this approach to me, but their guidance, which has really stuck with me as well, is rather than walking someone through your thought process—meaning, you know, you take their hand and step by step, like, "Well, there's this and there's that and there's this and there's that. You put those together, then it means this"—if you just put them in front of you and kind of ask them open questions and get them to explore the space in their own way, firstly, it means that when they—well, when/if they end up in the same place as you did, it's just much more of a—it's built on a much more solid foundation. It's not some inherited knowledge which they kind of trust, but not really. It's something that they felt came from them and their own reasoning. And secondly, and in many ways more importantly, they can end up somewhere different because they've brought a different perspective to the discussion. And all of a sudden, you're like, "Oh, crap. Yeah. No. That's actually a really good point. I didn't see that." And if you just kind of walked them through the steps that you'd taken, it stifles that debate or it kind of works around that debate or—you don't get value from the other perspective and from the person's context.

(James Brady at 00:59:17) So, yeah, again, really effective for both those reasons.

(Joel Beasley at 00:59:20) Yeah. It's interesting. It's like if your goal is to sell it, then the idea of speaking first and walking people through your decision-making process is exactly what you need to do. But if your decision is to understand if your assumptions are right, then you have to go with the Simon Sinek "leaders speak last" type deal, right?

(James Brady at 00:59:41) Yeah. That's a great distinction of what are you trying to do. And I think, um, so, you know, in my role, obviously I interact with lots of different vendors who we either already use or they're trying to pitch us on something. And there seems to have been a bit of a shift over the last year or so where, if I'm talking to someone in sales, rather than them kind of pitching me and giving their value proposition, it's very much like, "We want to learn"—I mean, they've kind of always said, "We want to learn about your business," but it seems more authentic now. And we actually are kind of walking through, "This is my main pain point," and it's not through the lens of what they offer. It's through the lens of what we need, which, I mean, sounds simplistic when I say it that way, but I've had multiple years beforehand of getting on a call and it's, you know, it's a template presentation. They've just changed my name on the first slide, and they kind of walk through as always. It's true with everyone else. And for obvious reasons, that doesn't really hit home as much as the other one, which you're kind of building relationship and building rapport and building trust.

(James Brady at 01:00:55) But also, we're kind of—if we get to the end of that and they say, "You know what? We're probably just not a good fit for this, that, and the other reason," that is—you know, I would go and recommend that company to everyone who would listen to me because, you know, they've been authentic and we've explored something together, and I feel like that's a useful experience for anyone whether they use the product or not.

(Joel Beasley at 01:01:17) Yes. Yeah. Do companies with their honesty and trust. I mean, plus it's like, as a business owner, it's like that's—I want to operate the business that I like, a business I respect, right?

(Joel Beasley at 01:01:29) It's like I want my people to figure out, you know, are we useful for you? You know, what do they actually want? When I go into sales calls, like when we're buying technology, before I go into the sales call, because usually it'll be like my team — I'll give you a specific example. It was with like ZoomInfo.

(Joel Beasley at 01:01:47) So we needed outbound. We need like B2B contact information.

(James Brady at 01:01:52) Right.

(Joel Beasley at 01:01:52) They had it. We had another system we were using. We were looking for some like three specific features that would allow it to be more efficient and we couldn't find them. So my team came to me and they said, "Hey, we want to do this." It's like we check the quality of the data.

(Joel Beasley at 01:02:07) It's there. And I said, they're like, "What sort of questions do you have?" And so I wrote my — I thought deeply. I went through. I said, "Okay.

(Joel Beasley at 01:02:13) If you guys want to do it and it's better, that's great. Here's what we need from a technical perspective. We need these three abilities." And when we got on the call, it was like, you know, just whatever canned presentation that they were going to give us. But then I just stopped it.

(Joel Beasley at 01:02:26) Like I'm like, "I'm not going to sit here for 45 minutes so you feel better. I've got like other things to do. I've got 20 minutes. Do you have these three features?" But the cool thing was, and why I definitely liked them, is they instantly snapped out of that.

(Joel Beasley at 01:02:37) Right? And we're just like, "Okay, here you go. You know, yes, we can do this. No." You know, so on and so forth.

(Joel Beasley at 01:02:42) And we became a customer. And it was, you know, so far they've been a great company and everything. But the point of that story was a few years ago I stopped like letting the salesperson do any of the presenting to me without knowing. So like if they don't ask me within like the first two minutes of the call, like what are the points and the takeaways and what do I need to make this happen and what's going on in my life and how did they — it's like it was like an inefficient process we all kind of fell into of like let me show you what I've built and figure out how to map it back to you. And now it's just like we know all the ins and outs.

(Joel Beasley at 01:03:21) We know exactly who our target audience is. You tell me what your pain point is, and we know if we solve that pain point or not. And you know your pain point, there's like less — there's less noise and more signal. Right?

(James Brady at 01:03:33) Yeah. Yeah. I mean, there's a place for the kind of expansive vision of what the company plans to be and, you know, the kind of space that they see themselves in and that kind of thing. But yeah. No.

(James Brady at 01:03:46) I completely agree. In the first call, you don't want to hear the pitch, like the capital P pitch. You just, is this going to be useful? Is it going to be more useful than I'm already using or whatever? I wonder if — so are you familiar with Steve Blank and his customer development process?

(James Brady at 01:04:06) No. He wrote a book called Four Steps to the Epiphany where he details this, and it's more aimed at product managers, I would say. But it gives you a kind of structured approach for how to figure out what you should build as a technology company, which is, as the name would imply, is very much focused around the customer. It's like discovering the customer, validating that they pay for something, validating what features they need. And there's a clear parallel here between what he's talking about in terms of a product development process and then a sales process of, rather than kind of blurting out all the stuff that the product can do, which may or may not be relevant, engaging with the person on the sales call and, you know, what is it that you need and how does that match up with what we do?

(James Brady at 01:04:56) And, you know, I'd never thought of it in that perspective before, but you could probably extend the kind of product development, customer development process into, okay, now we're on sales calls and close that feedback loop, which, you know, isn't as tight as it needs to be very often. I would say, you know, someone complains to customer service or a salesperson fails to make a sale, but we don't — I don't know if — I don't know if people are necessarily — I'll tell you that I don't think Teespring are good enough at kind of closing that feedback loop of exactly why did this buyer have an issue and like how — let's kind of feed that really kind of directly into our iteration process. And why didn't we manage to close this person, or why is this person having an issue with the platform? But yeah, it's not two discontinuous phases. It should be kind of one continuous loop, right, where we're kind of building something, selling something, they're using it.

(James Brady at 01:06:01) We're building something, we're selling something, yeah, they're using it. I don't think — I hope people aren't listening to this thing and thinking that's exactly what we do already and these guys are idiots for not doing it. But, uh —

(Joel Beasley at 01:06:14) No. I have a question though about the — so I've seen every possible structure of team. But one of them that I saw that I thought was pretty interesting is where they'll have like a team, but they'll have like an account executive, a business development rep, customer service or account person, some sort of like engineer, right? And they'll all like sit physically near each other or would be on a team so that what you get is they'll also go back away and connect with their whole teams. Like so all the engineers will go back and connect with all the engineers and come back.

(Joel Beasley at 01:06:52) And it was just an interesting way to pass information because then the engineer sitting there while the salesperson is like complaining to the BDR that they didn't get the sale because we didn't have this feature. And so that information just finds its way in.

(James Brady at 01:07:05) Here.

(Joel Beasley at 01:07:05) I'm sure there's plenty of successful ways to do it without that setup, but I thought that was pretty fascinating.

(James Brady at 01:07:12) Yeah. I completely agree. Like, we — it's those sorts of people who — is that — it's those profiles that need to be talking all the time, all the time. It's something that we've always had at Teespring, this idea of splitting the teams into vertical stacks rather than horizontal slices. So we've never had a front end team, a back end team, database team.

(James Brady at 01:07:38) It's always been product-focused teams that we call pods. You know, this is the group of people that are responsible for this type of user or for this experience. And there's front end engineers, back end engineers, a dedicated product manager, and so on and so forth. What we're doing right now is actually moving much more towards what you described where let's broaden that out even more. It's not just engineers, engineering managers, and product managers that should be talking all the time.

(James Brady at 01:08:07) We're going to bring in a marketing person, a salesperson, someone from operations and supply chain, someone from data. It kind of depends on what the team needs, but let's just get them together. They should be in the retrospectives because it's the kind of overall functioning of that group of people that needs to be retrospected. Don't know what the past tense of that is.

(Joel Beasley at 01:08:32) I'll buy it. Okay.

(James Brady at 01:08:34) Yeah. Thank you. Stick with me. It gets better. And it's actually mentioned in — I can't take any credit for this at all.

(James Brady at 01:08:40) It's also in that Sense and Respond book of, you know, these kind of cross-functional independently operating teams that should have a clear intent, goals — as in like metrics, APIs — and also constraints of it. You know, you can't use the brand in this way. You can hire this many people. But yeah, in order for that group to be as successful as possible, they need to not — we're trying to find a way of reducing the kind of the siloing of knowledge or experience or function within a department, and we're sort of elevating to primacy.

(James Brady at 01:09:17) This cross-functional team, something that we haven't kind of fully done yet, but I'm really excited about rolling out really, really, really shortly, actually.

(Joel Beasley at 01:09:27) I'm actually pretty pumped up about that. It sounds — why don't you come on like next year and we could talk about that? We'll see like how it's gone, what's up, what you've learned.

(James Brady at 01:09:37) I would love that. It holds me to it as well. I know I've got 12 months to not just roll it out but figure out and make it successful. Or if not, I'll have a good story about how it fell flat on its face.

(Joel Beasley at 01:09:46) Yeah. Either way, it works.

(James Brady at 01:09:48) That's true. I like that. Yeah.

(Joel Beasley at 01:09:49) Yeah. So what's some — what's some insight or — I guess the question I want to ask is what is one of those truths that you've learned like over and over as a leader? Something that like it's a lesson, it's come up multiple times throughout your career?

(James Brady at 01:10:08) That's a good question. Come up multiple times is a tricky one. I think the one I would pick out is that — I don't know if it's just me or if it's engineers in general, but we do tend to maybe sort of, if not oversimplify things, we want to kind of jump in, roll our sleeves up, get building. This is a really tricky problem. We're going to crack it like a nut.

(James Brady at 01:10:43) And I think when we take that approach, it means that we don't go through that sort of learning, exploration, validation, bringing people along, bringing people together within the team, doing that kind of customer development process thing that I mentioned. You know? Like the reason that I was first familiar with that book in — must have been, sorry, ten years ago or something — where we had, we had as a team kind of jumped into solving mode. We sort of had a bit of a hint that there was a problem over here that could be helped with technology, and we just kind of jumped in and started writing code, which kind of worked, but doesn't really scale, and it definitely doesn't last. You sort of have to be lucky. So to kind of abstract that out a little bit, I think it's — I think it's that you need to be humble about what you know, what you don't know, and clearly identify where risks or assumptions are and not just kind of jump into something.

(James Brady at 01:11:51) I think I certainly personally get very excited about a new project or a new idea and kind of jump into solving mode, writing code, pushing stuff up, trying things out. And at best, at best, you can kind of, if you're lucky, you can kind of invalidate an idea quickly with that approach. But I think it's just way cheaper in terms of time, in terms of money, in terms of emotion by doing something much lighter weight with a sort of a prototype, a wireframe, a conversation, a survey, a look at competitors, whatever it might be. So I don't really have a kind of pithy one-liner for that, but I think it's —

(Joel Beasley at 01:12:33) Oh, well then we're going to have to cancel the interview. Okay.

(James Brady at 01:12:38) Oh, I thought we were just about to get started.

(Joel Beasley at 01:12:42) Yeah. Well, this is just the intro banter.

(James Brady at 01:12:44) Okay. Do you see what I mean?

(Joel Beasley at 01:12:47) I get exactly what you mean.

(James Brady at 01:12:49) Yeah. Yeah. And the reason, unfortunately, that is it's a kind of a truth I've learned again and again is because, you know, I'm an engineer. I love solving problems. I love diving in.

(James Brady at 01:13:00) I love solving hard problems. I love challenging myself and like, you know — what I'll be — I'll be talking with my wife about this. It would be nice if this service existed, this website existed. And rather than like validating it's a good idea or that anyone else would be interested apart from us two and the dog, I'll be like, "Well, the crucial thing here is it needs to be running on Kubernetes, which I've not used very much before. So I'll set up a — just quickly set up this Kubernetes cluster, and then the deployments will be super straightforward."

(James Brady at 01:13:30) You know, two weeks later, I'm like a bit more comfortable with Kubernetes, but it doesn't really — I've not actually really solved the problem. I've solved the problem I wanted to solve rather than actually kind of saying, where's the biggest risk, the biggest uncertainty? What's the best use of my time to actually move this idea forward rather than to kind of combine my career slash hobby, which is coding? You know?

(Joel Beasley at 01:13:57) Well, let's say we've got like an engineer. Right?

(James Brady at 01:14:00) Okay.

(Joel Beasley at 01:14:01) And this engineer is newer in their career, and they've been building and building. But professionally, their experience is 99% just building. Here are some specs. This is what we're going to build. Yeah.

(Joel Beasley at 01:14:12) Let's get started right now. Here's step one. Here's step two. Let's build, build, build. So imagine that's like your brain would be like the operating system and that builder is like the builder program in your operating system.

(Joel Beasley at 01:14:24) Right? But you're newer. Right? You're less experienced, so that's like one of the only programs you have to even run. Yeah.

(Joel Beasley at 01:14:30) And so as your consciousness starts shooting instruction about like, "Hey. Let's build this technology." The program that's going to pick it up is the builder program, and it's going to start issuing the stage one commands. And so what you have to do is like build these other programs in your mind and like set them up and do your automation with them and make sure you filter them around so that it's less about just running the building program and more about this like larger problem you're trying to solve and value you're trying to bring. Yeah.

(James Brady at 01:15:01) Yeah. You are not joking about treating your brain like a Turing machine. Like it kind of comes across very strongly.

(Joel Beasley at 01:15:08) I got — we can talk about my morning routine, which I call my boot sequence. I'm nerdy. Yeah. Sorry.

(James Brady at 01:15:17) But no, no. I think you're right. It's — I don't know if you've heard this little — I don't know if it's a truism or just a saying, but they say that there are three types of engineers. There's people that love solving hard problems. There's people that love designing beautiful things, and there's people that love sort of solving a sort of high-level problem.

(James Brady at 01:15:38) There's sort of — they take a maybe a slightly more product-y approach. And I think it's kind of an oversimplification. You can get good at all three. You can love doing all three, and you can kind of grow those over time. But no, I agree.

(James Brady at 01:15:52) Like you, if you're lucky, you start off being kind of half decent at one of them, and you need to add those other tools into your toolbox. I think — where the — to kind of connect two thoughts here — one of the benefits I'm hoping to see from that kind of cross-functional team approach where we bring people together and say your mission is to make this thing successful rather than your mission is to ship this thing. It gives, especially junior engineers, much more visibility into the totality of what makes software valuable. And it isn't getting it shipped. It is people using it, finding it useful, continuing to use it, paying for it, and whatever else.

(James Brady at 01:16:40) And, you know, that feedback loop being more clearly presented to them and being something that the team values and that the team should be talking about KPIs daily, it really kind of accelerates that learning process, right, where, yes, they'll be getting better at writing good code through mentoring, pairing, practice. But there's also that kind of daily reinforcement of it doesn't matter if people don't use it. It doesn't matter if you all don't like it. So it kind of enforces that as they work on stuff sprint by sprint as well. I'm hoping that happens because that's like a huge win for the personal development, career development of people, especially more junior folks.

(James Brady at 01:17:23) I think it also is helpful for less technically inclined people, like the non-engineers who are a part of that cross-functional team. If they are presented front and center with how annoying it can be to—if you've rushed out a prototype to see if something is even interesting, and then we're like, it is interesting, let's move forward, let's do a V1—if they can see on a daily basis or a weekly basis how frustrating it is to work on this kind of slightly junky foundations that underpin the prototype, that's a hugely useful thing for them to have in their toolchain as well.

(James Brady at 01:18:02) And they can have really good, rich conversations with engineers at Teespring and beyond. You know? It's something that is really transferable into other companies too.

(Joel Beasley at 01:18:12) Yes. Look, so we definitely have to have you on next year. Are you down for that?

(James Brady at 01:18:17) Yeah, for sure. A year from now, I wonder what we're going to be doing quarantine-wise. That'll be another interesting topic.

(Joel Beasley at 01:18:23) Well, if you're in the States and you're not quarantined, you can come by here. We have the studio now. You can see the—

(James Brady at 01:18:29) —slate wall in person. Yeah. I can lean on it and destroy it. I'm sure that's kind of the look I have.

(Joel Beasley at 01:18:34) We'll keep you—

(James Brady at 01:18:37) —far from—

(Joel Beasley at 01:18:38) —the wall. Okay. Okay. No, this would be great because we literally got through like a third of the things. We didn't even get to the Nick Bostrom stuff and all that. But we will save that for next time, and then I'll continue stalking your blog and looking at your cool ideas. But I'm very grateful to have met you. I really like you. I hope that you're a person in life that I know in twenty years, right?

(Joel Beasley at 01:19:00) Because—

(James Brady at 01:19:01) Thank you.

(Joel Beasley at 01:19:01) —you have really good ideas.

(James Brady at 01:19:02) That's a very kind thing to say. Yeah, this has been a really fun conversation. We sort of covered a lot of ground, I think, and managed to—the thing that I really enjoyed is that we managed to connect a few of the dots as well, including in ways that weren't evident to me before until we started talking through them, which is always a good sign for having learned something.

(Joel Beasley at 01:19:23) Yeah, it's what we do. We try to just explore ideas. So I don't care if people don't have a pithy one-line thing. It's like, you have an idea that's a good idea, and we can talk—that's how you get ideas better, is by talking them out with other people.

(James Brady at 01:19:37) 100%. Yeah. Yeah. Thank you so much for having me on. It was a blast.

(Joel Beasley at 01:19:42) Thank you so much. Have a great night.

(James Brady at 01:19:44) Okay. Thanks. Bye-bye.

(Joel Beasley at 01:19:47) Thank you so much for listening. And if you found this episode useful, please share it with a friend or colleague who you think would get value from it. And if you have topics that you would like to hear discussed on the podcast, either add me on LinkedIn or send me an email: [email protected]. Every time I get an email or LinkedIn message, it absolutely makes my day and inspires me to keep going.