Chad Fowler CTO Microsoft Startup Advocacy

(Joel Beasley at 00:00:00) Today we are talking to Chad Fowler, the CTO of Microsoft Startup Advocacy, and we discuss what it means to be venture funded, common mistakes founders make and how to avoid them, and how you can become an expert on a subject through the process of writing a book. All of this right here, right now on the Modern CTO podcast. Here we go. This is the Modern CTO podcast. You know, I was just talking with a technical leader in cybersecurity at Cisco.

(Chad Fowler at 00:00:40) Mm-hmm.

(Joel Beasley at 00:00:40) And right before this call, and he says, "Oh, is he related to Martin Fowler?" And I'm like, "I have no idea."

(Chad Fowler at 00:00:48) Maybe.

(Joel Beasley at 00:00:49) Maybe?

(Chad Fowler at 00:00:50) Maybe remotely.

(Joel Beasley at 00:00:52) Third cousin? We'll go with third cousin.

(Chad Fowler at 00:00:55) Yeah, could be. We should actually check that just to really set the record straight. We don't know.

(Joel Beasley at 00:01:01) We'll do DNA testing. We'll do, like, a 23andMe. We'll get 23andMe CTO on the show, and then we'll get both of you on the show, and then we'll do the mouth swabs. We'll throw me in there just to make sure that we're not somehow related.

(Chad Fowler at 00:01:15) Yeah, of course. We don't seem to be, though.

(Joel Beasley at 00:01:19) And your history—I mean, you're Chad Fowler.

(Chad Fowler at 00:01:23) I am. I have been since I was born, too.

(Joel Beasley at 00:01:28) So yeah, it was interesting because I saw that Twitter happen, and then a couple people mentioned, you know, my book and my resources. And then later I got the Google ping, and I was like, "Oh, there's Chad." And then I was like, "Why does that name sound so familiar?" And I'm sitting there thinking, and then I realized. So I look you up, and I start looking through your books. I'm like, "Oh, I have his books. Like, they're in my office." I was reading you years ago when I was out in Portland, and I went to, I think, Powell's Books, like a very large bookstore. And I went and I just grabbed a stack of Ruby books, and I read through them all to learn just different designs, testing, couple different things I was really interested in at the time. And they were the good books that I kept around, and so it was very cool to see that.

(Chad Fowler at 00:02:16) Yeah, cool. Sometimes I forget that I've written books. I tend to forget to mention that when I introduce myself these days.

(Joel Beasley at 00:02:23) Yeah. "Hi, I'm Chad Fowler, the writer of books." "Which book?" "No, no, no. I'm the writer of books. Like, I just write books." Have you read this one, Peter Thiel?

(Chad Fowler at 00:02:33) I have read that one.

(Joel Beasley at 00:02:34) Yes. This is the one. So I read the back, which prompted the purchase. And then I had, you know, read a little summary, and I was like, "You know what? Peter Thiel's like the person to read if you're gonna read, right?" Like, if you want to know about startups, right, why not talk to one of the most prolific investors, period?

(Chad Fowler at 00:02:57) Yeah, and entrepreneurs.

(Joel Beasley at 00:03:00) Yeah, and entrepreneurs. Yeah, we just talk. This is the podcast.

(Chad Fowler at 00:03:04) Okay, good.

(Joel Beasley at 00:03:04) Yeah.

(Chad Fowler at 00:03:05) I'd like to welcome myself to the podcast, then.

(Joel Beasley at 00:03:07) Oh, yes, yes. We don't really acknowledge the audience. They're more like—thanks, Jake. We can be as off or on topic as we want. Really, what we found when I started the podcast is that people just like listening to us talk about technology stuff. And if they buy the person, then they're interested in what they have to say as far as experience and advice.

(Chad Fowler at 00:03:33) So you're running the podcast like it's a product, and you're doing funnel optimization.

(Joel Beasley at 00:03:38) 100%. Yeah, we bring value to the market, and the only thing we're interested in is how to do that better.

(Chad Fowler at 00:03:46) Yeah, cool.

(Joel Beasley at 00:03:47) Yeah. So you do that with your books, right? You take an iterative approach with your writings, like always reaching out to people and engaging and finding out what they want to hear about?

(Chad Fowler at 00:03:55) I guess. I mean, it's been so long since I've written a book, it's hard to even remember. Maybe with books, it's not quite like that because it's a more monolithic process and, frankly, an outdated process, I think, which is partly why I was saying I forget to introduce myself as an author, because it seems like everyone's an author now. And the fact that someone bothered to print what I wrote on a bunch of paper and ship it all over the place is not so exciting these days like it used to be. You know? Like, you were talking about going to Powell's and picking up a stack of books. That's not what people do anymore. It used to be. Like, I used to go when I was starting out because I'm self-taught. I was a musician. I got excited about programming. Are you too?

(Joel Beasley at 00:04:44) I mean, I play drums and guitar. I used to play electric drums and saxophone.

(Chad Fowler at 00:04:49) Oh, cool. I think you told me that. Saxophone is my main instrument.

(Joel Beasley at 00:04:52) Yeah, alto sax for about a decade.

(Chad Fowler at 00:04:56) Yeah, nice. Alto is my main thing, too.

(Joel Beasley at 00:04:58) Oh, nice.

(Chad Fowler at 00:04:59) But, you know, back in the day I would go to Barnes & Noble—that was the one that was the main one back then. Then Borders came out, and that was amazing. And I would go and buy so many books. It was hard to get them to the car and then just sit and go through them and literally read all of them. Maybe not cover to cover, but most of them. It's not like that anymore. You know, there isn't like this—

(Joel Beasley at 00:05:24) You don't do that anymore?

(Chad Fowler at 00:05:25) No. Come on. What bookstore do you go to and find—

(Joel Beasley at 00:05:28) Amazon.

(Chad Fowler at 00:05:29) Books that you actually—yeah, but that's not—it's not the same anymore.

(Joel Beasley at 00:05:33) But look, they give me my books. And look at this, this is a whole stack of books right here. You see that? Those are three different boxes of books.

(Chad Fowler at 00:05:40) Physical paper books.

(Joel Beasley at 00:05:41) You want to do some unwrapping real quick?

(Chad Fowler at 00:05:43) Sure, why not?

(Joel Beasley at 00:05:44) Let's do some unwrapping. Jake, we're gonna need a knife. One second. That's a serious knife, Jake. All right, Chad, I'm so excited, man. Look at this knife.

(Chad Fowler at 00:05:53) Yeah, that's quite a knife. You live in the South, really.

(Joel Beasley at 00:05:55) Yeah, this is Jake's knife. This is not my knife. Jake is prepared at any point in time to go to war, I believe.

(Chad Fowler at 00:06:05) Well, we all are in the South, right? That's part of the culture.

(Joel Beasley at 00:06:08) Where are you at in the South?

(Chad Fowler at 00:06:09) I'm in Arkansas.

(Joel Beasley at 00:06:11) Oh, nice. You're in a safe space. Like, that's a space where you're not gonna get attacked first, so you can have some planning time. Like Florida, we're surrounded by water. We're primed for attack.

(Chad Fowler at 00:06:24) Yeah, that's true. There's no reason to attack Arkansas. It's already killing itself, basically.

(Joel Beasley at 00:06:28) Oh, no. We need to get some Tony Robbins and Zoloft shipped to Arkansas. Oh, man. So you don't go to bookstores anymore. How many paper books do you order now?

(Chad Fowler at 00:06:41) I don't know. I've kind of started getting them again, but it's not a very good format, really. Especially if you travel a lot, you've got to carry this thing around all over the place. It's heavy. Like, I remember I used to travel to Europe, and my suitcase would be heavy because I had so many books with me when I went on vacation. But the worst thing is all of these books that you're about to pull out of this box, if they're technical books, they're already obsolete. And you don't know which parts are current and which aren't. The software doesn't ship like it used to. It ships every day, all the time. As a technical author, that's also very frustrating if you're trying to maintain a monolithic book about technical stuff, and they keep shipping changes. Like, when I did the Rails Recipes book in 2006, I had to hurriedly change a bunch of stuff, and we worked with the Rails core team so that I could release it right when I think it was Rails 1.0 came out. That's when I released the book. So at least I could say this book is relevant for Rails 1.0. But by Rails 1.1, it was not up to date anymore.

(Joel Beasley at 00:07:45) Some of the principles, though—like, most of the book was useful still.

(Chad Fowler at 00:07:49) Sure, but that's a pretty lame medium if you have to immediately start apologizing for it.

(Joel Beasley at 00:07:55) Is that what your experience was? Like, did you get a lot of outlash from the book?

(Chad Fowler at 00:08:02) Like backlash, you mean?

(Joel Beasley at 00:08:04) Yeah, I'll make up "outlash." Yeah.

(Chad Fowler at 00:08:06) Outlash. Yeah, I like outlash. I'm okay with that.

(Joel Beasley at 00:08:07) I'm okay with the words. I make words come out of me all the time by accident that don't really exist, but people know what they mean because they sound like the feeling.

(Chad Fowler at 00:08:19) Maybe outlash is a word because you do lash out, right? So I decided recently that when you talk about feedback, the unit of measure should be "a back of feed," that you can say, like, "How many backs of feed did you get from that podcast interview you did, and were they positive?"

(Joel Beasley at 00:08:36) Yeah.

(Chad Fowler at 00:08:37) Similar.

(Joel Beasley at 00:08:38) I like that. Backs of feed.

(Chad Fowler at 00:08:40) Yeah. I don't know if I got backlash or outlash from Rails Recipes, but there was definitely a bunch of maintenance involved. And the frustrating thing is—I mean, fortunately, by then people were doing PDFs. In fact, Pragmatic Bookshelf was one of the ones that led the way in doing, you know, publishing PDFs of books. They weren't DRMed or anything. So we could keep releasing new versions of the book, but if you bought the paper, then it was just out of date within months. Totally out of date.

(Joel Beasley at 00:09:12) That's so sad. But now we have digital.

(Chad Fowler at 00:09:15) Mm-hmm. But you—

(Joel Beasley at 00:09:16) You do a lot of maintenance to the books.

(Chad Fowler at 00:09:18) I did then, yes. I haven't in a long time.

(Joel Beasley at 00:09:20) Yeah. I don't think there's much need for the maintenance. Like, you put it out, it's relevant to what it is. People in that moment consume it because they need it and the market wants it. And then later when enough change has happened, you put out a more relevant book. I mean, you could have written a book for every major version of Rails, and I would have bought each one.

(Chad Fowler at 00:09:42) But you've written a book. You know that that's a pain. You don't want to actually do that.

(Joel Beasley at 00:09:48) Make new books?

(Chad Fowler at 00:09:49) Yeah, constantly make new books.

(Joel Beasley at 00:09:50) I love it.

(Chad Fowler at 00:09:51) I always—oh, wow. You are strange. I always say that everyone who says they want to write a book, they actually want to have written a book. They don't want to write the book.

(Joel Beasley at 00:10:02) I love it. I'm obsessed with it. I've actually already have five books planned, and I have another one already complete. I just don't want to release two right back to back.

(Chad Fowler at 00:10:10) What's your next book, then? The one that's complete.

(Joel Beasley at 00:10:14) Leader Bits. Bits of Leadership.

(Chad Fowler at 00:10:17) Yeah, that's nice.

(Joel Beasley at 00:10:18) Yeah, yeah. I take little—I take concepts from—here we go, book number one, pulling out of the box.

(Chad Fowler at 00:10:24) See, that one's not obsolete, so that's a valid playbook for this right there.

(Joel Beasley at 00:10:29) Right? See, I'm buying valid. My strategy is to buy things that deserve to be in this medium, right?

(Chad Fowler at 00:10:36) I do that, too. Yeah, I have right here on my desk I have a book called Scrapbook Notes and Blueprints by William Parker, who is a free jazz bass player.

(Joel Beasley at 00:10:48) Oh, a free jazz bass player. That sounds—my first instrument ever was a bass guitar, but it didn't stick with me for some reason. Yeah, I had it. It was a Carlo Rubelli.

(Chad Fowler at 00:11:01) It's not a good young person instrument, really, because you don't get the limelight.

(Joel Beasley at 00:11:05) Yeah, I was, like, eight, and they gave me a bass. And I was like, "Why a bass?" And they're like, "Well, your cousin has drums and your brother does guitar, so you get the bass." I was like, "Okay."

(Chad Fowler at 00:11:17) Big design up front. Yeah, family band.

(Joel Beasley at 00:11:22) So this is a good book. You enjoy this book, right?

(Chad Fowler at 00:11:25) I read that in paper on a cruise ship.

(Joel Beasley at 00:11:29) What—where were you cruising to?

(Chad Fowler at 00:11:31) It was—I would like to say before I mention this that I considered myself—my wife and I considered ourselves to be unlikely cruisers. That feels like such a suburban way to have a vacation. But we were sent on a cruise by my company, and we chose the Baltic Sea so that we would be surrounded by old people instead of, you know, people trying to party and drink like crazy.

(Joel Beasley at 00:11:58) That is true. Yeah, I'm not a big party drinker person.

(Chad Fowler at 00:12:04) Yeah, but you don't—yeah. Certainly wasn't back then.

(Joel Beasley at 00:12:09) So how old are you now? You're early twenties, right?

(Chad Fowler at 00:12:13) Yeah, 44.

(Joel Beasley at 00:12:15) 44, nice.

(Chad Fowler at 00:12:16) I just turned 44 four days ago.

(Joel Beasley at 00:12:19) Oh, happy birthday to you, Chad. We'll edit that for sure.

(Chad Fowler at 00:12:27) No, no. You've got to leave that one in. I'll be really angry if you don't leave that in.

(Joel Beasley at 00:12:33) So here's the problem with books. We were talking about—you were talking about the problem with books being ephemeral, right? They don't last very long. And by the way, that's my word of the week. So ephemeral. Yeah, I don't know. I saw it, and I really enjoyed it. And I was like, "I'm gonna just inject this into my vocabulary for a little bit."

(Chad Fowler at 00:12:52) Just use it in every conversation at least once.

(Joel Beasley at 00:12:56) Yeah, for sure. That's—yeah, until the next word comes along. So the problem with books, other than the ephemeralness—there's a new word—of their nature, there's, like, 12, 14 things, like, in every book, like good pieces of information. But if you don't do something with that information, it's just gone. Like, unless you act upon it—knowledge, everybody's like, "Oh, knowledge is powerful." And for a while, I was on that train, on that ship, on that cruise ship. Knowledge is powerful. But now I'm like, knowledge is the potential of power. So I have this book here. It's got knowledge in it, which is potential. And if I give you that book and you consume that book, you simply transfer the domain from the text of the pages to your mind structure, right? And so it hasn't done anything yet. It's still—the potential is just being transferred, and it's not until you take action with that potential and use it that it actually does something and it actually exerts its power. So knowledge is the potential of power, and then the actual exercising of that knowledge is powerful.

(Chad Fowler at 00:14:10) I agree with that. Although, there is an implicit assumption there that I think is carried with books, specifically that medium. And the implicit assumption is that the knowledge contained therein is valid and correct.

(Joel Beasley at 00:14:24) Yeah. It's a trust medium. It's got way higher trust than anything else.

(Chad Fowler at 00:14:29) Right. Because you believe that it's vetted by a publisher, and really, the fact that you're holding this paper thing with a designed cover and all that gives it more of a feeling of authority than it even deserves because, you know, who are these publishers? You don't know them. It's just like having a college degree. You don't understand really the accreditation process for MIT, and I doubt—did you go to MIT?

(Chad Fowler at 00:14:56) I didn't.

(Joel Beasley at 00:14:57) I did take a course at MIT.

(Chad Fowler at 00:14:59) Forget MIT then.

(Joel Beasley at 00:15:01) No, let's use it. Let's beat them up for sure.

(Chad Fowler at 00:15:03) I'll be—

(Joel Beasley at 00:15:03) I'll be in Boston later this year, so I'll be like, "Hey, we rocked you on the podcast."

(Chad Fowler at 00:15:09) But, you know, we all assume a CS degree from MIT is a great credential to have.

(Joel Beasley at 00:15:16) Yeah. It's branding.

(Chad Fowler at 00:15:18) But why? Yeah. We don't know. I didn't go there. I haven't seen what they learn.

(Chad Fowler at 00:15:23) I haven't seen anything really about MIT other than I know some people who went there and they seem smart.

(Joel Beasley at 00:15:29) You want the general population to think critically? Because that's not a thing that'll happen.

(Chad Fowler at 00:15:37) I don't think they will. I'm fine with that. But I'm just saying the college degree and the fact that this book is printed on paper and distributed by O'Reilly, those give it some proxy for authority that they don't necessarily deserve.

(Joel Beasley at 00:15:54) Oh, look at the guy on the quote on the front of this book called Scaling Teams. It's by Michael Lopp from Rands in Repose. I actually just got into their Slack channel. Have you been into that?

(Chad Fowler at 00:16:04) I have, yes. I spoke at a conference with Michael last year in Sweden.

(Joel Beasley at 00:16:10) What?

(Chad Fowler at 00:16:11) He's one of those people you make fast friends with, and we spent three full days almost all the time together, and then I haven't spoken to him since, but I consider him a friend.

(Joel Beasley at 00:16:23) Those are the best relationships. Right? When you get with someone, you click with them, it's just like, we're here, it's now. You get along great, and then three years can pass. Then the next time you're in that situation, it's just like, boom, you're right back at it.

(Chad Fowler at 00:16:35) Yeah, exactly.

(Joel Beasley at 00:16:37) Yeah. Low commitment, and it's highly rewarding. I like that. And, actually, the person I was just speaking with that I mentioned at the beginning of the call from Cisco, he just got back. He was referred to me by this company called Naked, N-A-K-D, which is one of the largest clothing companies, brands, in Sweden, but they're spelled N-A-K-D.

(Joel Beasley at 00:16:58) And so we had Nicholas on the show. He was the CTO. He went into that company. I think they had thirty-four people, and they were $20 million. And they had a lot of technical problems because the shop software wasn't shipping, and they were online retailer primarily.

(Joel Beasley at 00:17:14) And he came in there, reworked everything, boom. They went from thirty, sixty, ninety people from $20 million to $100 million inside of two years because they got their technology right.

(Chad Fowler at 00:17:23) Wow.

(Joel Beasley at 00:17:24) Yeah. And so he referred me. So then the Cisco technical leader was over in Sweden looking to expat to Sweden and meet some people. And so Nicholas met him and then referred him to me, and then I did a call with him this morning, and now we're talking to Chad Fowler. Happy birthday to you.

(Chad Fowler at 00:17:47) I didn't expect this to be such a disturbing experience.

(Joel Beasley at 00:17:50) Yeah. There we go. So let's talk about a day in the life of Chad. So you're traveling. You're speaking at conferences. This is what you're doing mostly?

(Chad Fowler at 00:18:01) Yeah. I have a new job. So the day in the life of me has gotten different, and it's hard to tell you what the average is now. But I work at Microsoft.

(Joel Beasley at 00:18:12) You work at Microsoft?

(Chad Fowler at 00:18:13) I do.

(Joel Beasley at 00:18:15) What are you doing at Microsoft? HoloLens stuff?

(Chad Fowler at 00:18:18) No. I am in charge of a thing called Startup Advocacy. And so I work at Microsoft because I was CTO at Wunderlist, and Microsoft acquired us almost three years ago. And I became the general manager for that product team for a while. Then I had to move back to the U.S., and I became CTO of the division that Wunderlist is in, which is a hodgepodge of stuff, including the software for the new Surface Hub 2 thing that was announced today, which is going to be pretty amazing. It's a whiteboard.

(Chad Fowler at 00:18:53) And really, I wanted to get back into the startup world because that's where I belong. And rather than leave the company, I was introduced to Charlotte Yarkoni who runs this group under—you may know of Scott Guthrie. He's my boss's boss. He's sort of famous in nerd world, especially in Microsoft corners. My job is to shape the new voice of the company to the startup community, both in and out of the startup community.

(Chad Fowler at 00:19:23) And the people that are on my team are all CTOs-in-residence at the accelerators around the world. So in the two months I've been in my job, I've been traveling all over the world going to these accelerators and meeting CTOs of local startups in London, Berlin, Paris, Tel Aviv, et cetera.

(Joel Beasley at 00:19:45) And so you run the team of CTOs-in-residence at the accelerators?

(Chad Fowler at 00:19:51) Yes. Yeah.

(Joel Beasley at 00:19:53) And are they being employed by Microsoft or the accelerator themselves, or does Microsoft contribute? How does that work?

(Chad Fowler at 00:20:03) So the accelerators in this case that I'm talking about are the Microsoft accelerators. It's called ScaleUp, and it's for Series A level companies that have revenue and they're looking to scale up sales and get into enterprise, government, et cetera, which are places that Microsoft can really help. Because we're obviously big in large enterprise clients, government, health care, education, places where trust is really important.

(Chad Fowler at 00:20:32) Microsoft has a huge presence. And so we're trying to take the power that we have and apply it to the startup community and amplify what startups are doing.

(Joel Beasley at 00:20:43) You guys are trying to do some good.

(Chad Fowler at 00:20:45) We are. Yeah. My philosophy for my team is help first, sell last, and if you never get to the selling part, it's fine.

(Joel Beasley at 00:20:52) Yes.

(Chad Fowler at 00:20:53) So my daily life is really just meeting with startups one call after the next and seeing how I can help them. And if it happens to be something that Microsoft can do, that's great. If it's something I can personally do, that's also great. I tell people, feel free to abuse me. Look me up on LinkedIn and see who I know, and I'll try and connect you if connections are helpful.

(Chad Fowler at 00:21:17) I'll help you review your pitch deck for funding. I'll help you review your architecture for your service that you're building, and all the people on my team are similarly like-minded and ready to do the exact same sort of work.

(Joel Beasley at 00:21:31) Wow. That's amazing. That's what we do. We do that at the podcast. I'm constantly connecting people, different CTOs to other different CTOs. And just whenever somebody needs help and they reach out, we kind of—either I jump on—I call them micro calls, which are off-the-show calls where I just jump on and hang out and answer questions and direct them to the right place and just kind of air traffic control relationships the best I can.

(Chad Fowler at 00:21:58) Yeah. That's good.

(Joel Beasley at 00:21:59) It's rewarding. It feels way better than anything else.

(Chad Fowler at 00:22:04) Right. And I think, you know, as a company, if you take the approach of just helping people, it's not just altruistic because, ultimately, they will see us as a valuable partner. But it also feels good and you see the positive influence you have on the world immediately as opposed to having that be an abstract thing. Instead, we see revenue as the abstract thing and helping people as the concrete thing, if that makes sense.

(Joel Beasley at 00:22:30) That makes total sense because we exist to bring value to the market. And so who doesn't want a capable, helpful individual on their team?

(Chad Fowler at 00:22:39) Right. So who are your listeners?

(Joel Beasley at 00:22:42) So our current numbers are 72,000 active listeners, which means they listen to at least one episode a month. And they break up into the CTOs, current CTOs, experienced CTOs, new CTOs, and then next generation, which would be software developers, project managers, individuals that want to move up into a technology leadership role.

(Chad Fowler at 00:23:09) Right. Yeah. That makes sense. And how can we best help them?

(Joel Beasley at 00:23:14) So typically, the feedback that I get is that they get value by hearing about you, what you're doing, and then any specific areas—I'm thinking here. So you do the startup thing. What's the most common mistake that you see when people come in these frequent meetings that you do with reviewing pitch decks and things like that?

(Chad Fowler at 00:23:36) Yeah. That's a good question. The most common mistake—I'm going to probably tell you more than one, and neither will be the most common. But, you know, off the top of my head, one category I see is startups, they have some passion for an idea for a tool they want to build, and they're so focused on the technology around the tool that they don't get what it takes to be venture funded. And the difference between a venture funded thing and, say, an app you would build and put on an app store.

(Chad Fowler at 00:24:05) You know, the way that you need to approach these challenges is really different, and not everything should be venture funded, obviously. Most things shouldn't be. But, you know, when you're going for venture funding, you need to have an idea that is about scale, and you need to have a really grand vision around it. And I often see people coming looking for venture funding and what they have is a tool and not something that can ultimately build into a platform. So I tend to ask people, imagine that it's eight or ten years from now and you're about to IPO and you're the CTO or CEO, founder, and you're about to do your roadshow.

(Chad Fowler at 00:24:43) What in this imaginary scenario do you tell the people on the roadshow as potential investors about your IPO? And, you know, they're starting out with, I don't know, some—let's, I'm going to make one up so that I don't actually talk about a real startup, but let's say they're building a tool for error detection in JavaScript and web pages, and it's just great. And literally, I look at it and I say, this is great. I love this. But when you step back and you ask yourself that question, like, what is the big picture value this brings to the world?

(Chad Fowler at 00:25:14) It's hard to see going from "this is a much better tool than the one that we all currently use" to "this is a company that is worth billions of dollars." And if they can't figure out a path, a make-believe version of that vision, it's probably not a venture fundable company. So, you know, you have to start thinking about that. And then so what I usually do is I say, give me that crazy vision.

(Chad Fowler at 00:25:40) I know it's going to be wrong, but tell me your daydream of what your company is like on the IPO day. Now back me up to the ridiculously pragmatic version of what you're going to do right now. So it's okay if right now all you've got is a tool that helps with error tracking of JavaScript on web pages, as long as there are a set of steps that I know aren't going to be the real steps, but I believe they could be from here to that IPO event. But I see that you have a framework for thinking about this as a business.

(Joel Beasley at 00:26:10) Yes. So you can see that they think deeper than just the right now.

(Chad Fowler at 00:26:14) Or broader or bigger, maybe not even deeper. You know? Sometimes technologists are too deep, and they just care about the depth of the technology, and they're not thinking about the value of the thing they're creating. Or they are, and they just don't get that, you know, as an investor when you're receiving a pitch like this, you're not evaluating "Is this a good thing?" You're evaluating, "Is this a good thing that I believe can be big enough to, let's say, return the entire fund that I've raised as a venture capitalist?"

(Chad Fowler at 00:26:44) And the reason that you need to do that, you know, I'm not sure if all the listeners know, but the way venture capital works is they go off to investors. VCs go off to investors and they pitch, and they say, "Invest in our fund, and we will be your proxy to the startup world. So we'll be doing high-risk investments, and you can just trust us by owning a percentage of what we're doing." Right? They are high-risk investments, and therefore, most of them will fail statistically.

(Chad Fowler at 00:27:12) And if you're not betting that every single one that you invest in will return the entire fund, then chances are you will end up losing money. That make sense?

(Joel Beasley at 00:27:23) That makes complete and total sense. Yeah.

(Chad Fowler at 00:27:25) So startups, if they can think about the perspective and be empathetic toward investors and understand the entire chain of where the money comes from, they'll get a better idea of how to present themselves and even strategically how to position themselves if they plan to be a venture funded company.

(Joel Beasley at 00:27:42) Dude, way to bring the value. So I was—that's in my head because I did private equity due diligence for several years. But I have never talked about on the show that connection between you're going to pitch the VCs, and the VCs have then gone and pitched independent people to get their money and funds so that they can be their arm of investment in the market. I've never explained that. I knew it, but, yay, Chad brought it out.

(Chad Fowler at 00:28:05) Yeah. And, you know, sometimes those people, the VCs are pitching, they're called LPs, and the LPs are sometimes fund of funds or something, or they're a fund manager for someone else. So there really is this hierarchy of they had to pitch someone in some cases. And in every case, it ends up really being about trusting the person, you know, believing in the credibility of the person you're talking to. Even if you're a VC, if you're a founder of a startup, you ultimately just have to convince someone that you get it well enough so that, you know, everything is going to be different than you expected.

(Chad Fowler at 00:28:42) So the investor needs to believe that you're going to react in a way that is valuable and agile at the right step.

(Joel Beasley at 00:28:50) Yeah. I just finished up Ray Dalio's Principles. Have you come across that one?

(Chad Fowler at 00:28:55) Mm-mm.

(Joel Beasley at 00:28:56) So he is a $170 billion fund manager, and, yeah, he is in the top five wealthiest people, influential people in the world. He just keeps a real low profile. But he has a book basically that came out, and he's like, "This is how I run business and how I run life" and 1,700 people at that company, that hedge fund. So it's called Bridgewater, but he has this concept that he talks about called believable people in his book. And it's this recurring theme he continually talks about.

(Joel Beasley at 00:29:27) So when you were discussing that, it was bringing that up in the back of my mind, like, yeah, believable people, and he discusses the different traits of believable people and how he identifies them. And I liked it so much because I have a chapter in my book called Validating Experts. And so I was really interested in how the same thing that I've come across and found to be true, other individuals have found to be true too. That's always exciting for me.

(Chad Fowler at 00:29:54) Yeah. That sounds good. I like that term, believable people.

(Joel Beasley at 00:29:58) Me too.

(Chad Fowler at 00:29:58) And it seems like the people who aren't believable are the ones that aren't actually listening to you most of the time. I don't know why. But somehow empathy and being believable seem to be tightly connected.

(Joel Beasley at 00:30:09) Listening and being believable, tightly connected. Yeah. It is. Because the people that listen understand the pulse of the market.

(Joel Beasley at 00:30:17) You can't understand what all the greatest Ruby developers think about structuring systems unless you've listened to all of them and then can form your opinion and try what they've expressed and have your own experience built on top of it.

(Chad Fowler at 00:30:32) Yeah. And you can't communicate really, you can't communicate well at all unless you're empathetic. You need to understand who you're talking to. That's why I asked you who your listeners are and what they want, because otherwise I'm just sitting here talking.

(Joel Beasley at 00:30:47) I love it. But I promise you, though, that I have the conversation structured in a way that they will definitely bring value. Also, realizing when you write the books and you're just you, right, and you go about your experiences and you have your family, but people will build up things in their head. Right? We're really good at that and create these structures in their head. So the act of, while I'm listening to you, I'm understanding how the audience is perceiving it because I interact with them so much. And so just by you being here and talking, even about the most abstract things about books and the medium of books and things like that, they are just very engaged with it, and that's bringing them value.

(Joel Beasley at 00:31:35) The act of being around Chad Fowler is useful because as humans, we have this superpower, this hidden superpower. So if I were to consume all of your content, like let's say Tony Robbins. Like, I'm going to consume all of Tony Robbins' content. I'm going to listen to his audio. I'm going to read his books. I'm going to go to his seminars. I'm going to do all of this stuff. I can completely consume all of his. And what I will get, the superpower I'm referring to, is the ability to start processing thoughts similar to that individual. So the more I'm around them, the more immersion I am around this person, the better ability I have to think like them. And then that's what we try to do here on the podcast is to have great CTOs and great leaders on constantly so that this next generation, they will binge listen or they'll completely consume all of these episodes, and then they'll have the macro ability to start thinking like these great technology leaders.

(Chad Fowler at 00:32:28) Yeah. I have a chapter in my book, The Passionate Programmer, called "Be the Worst." And the gist of it is, it's from a Pat Metheny quote, the guitarist. His advice to young musicians is always be the worst player in every band you're in. The premise is exactly what you're describing, that if you surround yourself with people that are better than you, you level up. You start thinking like them. Some of it is the filter because, you know, you see what they do, you hear what they do, and you start to filter, as you're saying, process information through that filter. You can't process it like them. You can only process it through the model you've created of them, of course. But the other is that you end up with different expectations for yourself when you're around people who are better at something than you are.

(Chad Fowler at 00:33:17) So probably the biggest kickstart that I had in my career was I went to this training thing. It's one of the only times I ever took any sort of a class about software development. It was called Extreme Programming Immersion. And it was in 2001. It was very early in the days of agile software development. It was actually before the Agile Manifesto was released. I remember because while I was there, Dave Thomas from The Pragmatic Programmers sent me a message.

(Joel Beasley at 00:33:47) Dave Thomas! It's a little known. Yeah, I love it.

(Chad Fowler at 00:33:51) He sent me a message on IRC, I think, with a link to agilemanifesto.org, encouraging me to be one of the first signatories outside of the Snowbird, Utah meeting they had while I was at this thing. But it was Bob Martin, his company was running it, aka Uncle Bob.

(Joel Beasley at 00:34:10) Uncle Bob?

(Chad Fowler at 00:34:11) And Ron Jeffries was a teacher. It was all the original agile, you know, extreme programming people. Kent Beck was there.

(Joel Beasley at 00:34:18) Oh, I like him too.

(Chad Fowler at 00:34:20) Yeah. And in fact, Kent—I mean, it was really all of them, but Kent was really the one that sort of flipped the switch for me. Being around him and all those brilliant people for a week, I actually said to my coworker as we were driving back from this course, because it was out of town, we'd driven to it, I felt so much smarter that week just being around those people. Like, it brought me up to a new level. And I told him, I need to work with people like that all the time so I can always be like that. And I think the only way to do it is to become one of those people. So that became my new goal in my career path. What does "become one of those people" mean? Right? Publish books and speak at conferences and do whatever it takes to gain a level of notoriety just so I can be associated with them and hang out with them.

(Joel Beasley at 00:35:07) Yeah. Are you describing me?

(Chad Fowler at 00:35:11) You're doing the same thing.

(Joel Beasley at 00:35:12) This is the podcast. I mean, I didn't realize that people wanted to talk about the craft and that there wasn't a place to talk about CTO craft and specifically with the CTOs and the technology leadership. So when I wrote the book, I started reaching out to people and asking them, before I publish the book, you know, am I going to get flamed? Because I was nervous putting myself out there for the first time. And then they turned into these great conversations, which we started sharing, and then eventually that became the podcast. And I found it incredibly easy to call up Intel and say, "Hey, I want to talk to your CTO about CTO stuff," and then just set a date. Like, it's kind of cool.

(Chad Fowler at 00:35:51) Yeah. You get a lot of access to people. The same thing happened for me when I started and co-organized RubyConf and RailsConf, the official conferences for those technologies. And the people that I was able to meet by, for example, organizing RailsConf keynotes, it was really amazing. You know, so we had Kent Beck and Bob Martin, all those sorts of people as keynotes. Obviously, David Hansson, I knew him from earlier days.

(Joel Beasley at 00:36:18) DHH.

(Chad Fowler at 00:36:19) I love that you do. You're like the rapper that stands behind the main rapper in his entourage. I'm a big fan.

(Joel Beasley at 00:36:25) I'm the hype guy.

(Chad Fowler at 00:36:27) Yeah. Yeah. That's what it is. The Flavor Flav of the group here.

(Joel Beasley at 00:36:30) But I really, the thing, though, is that I legit—this is like me. Like, I legitimately, this is what I love. And to be—

(Chad Fowler at 00:36:40) You're a real life hype man.

(Joel Beasley at 00:36:43) Yes, I am. And it's like the least sexiest thing in the world. Be like, "Yeah, I'm a CTO hype man. I know all the CTOs. I love them and I support them." Like, I geek out when somebody comes up with a new perspective of how to look at technology leadership, or they solve some problems in some interesting way I didn't think of. Right? Like, that's what I enjoy. And so writing apps for, you know, seventeen years and coding and then getting to sort of come out into the space of what I've been seeing my whole life is just, it's exciting to me. And all I want to do is two things. I want to meet great people, right, in the space, and I want to bring value to the community, which I've been a part of my entire life. And so the podcast allows me to do that. Writing allows me to—writing is the best way I found to teach myself. Like, one of the best ways. Like, I write, I learn, right? And then I write about it and I take some—and then I go take some experience and I go edit my writing. And then that process is the best process for me to enjoy my life.

(Chad Fowler at 00:37:51) Yeah. Martin Fowler told me years ago that whenever he wants to really learn a subject, he writes a book about it. When I heard that, I thought it sounded backward. Like, I thought, when I was young and foolish, I thought you write a book, you're already an expert in the subject. But then I wrote Rails Recipes. And when I did that, it was the second book that came out on Rails, and I was not actually doing Rails full time yet. I wasn't really that interested in web development. I was a Ruby programmer for several years already, though. And in the process of writing Rails Recipes, I became literally one of the world's leading experts in Rails because I read all of the source code, constantly talked to the Rails core team about what was going to be happening in Rails and what the wrong and right ways to do things were. And I met all the people who were leading the way with the technology. But before I started, I could basically just do a hello world in Rails because I was not so interested in it.

(Joel Beasley at 00:38:46) Yeah. I had Ryan Singer on the show.

(Chad Fowler at 00:38:48) Oh, cool.

(Joel Beasley at 00:38:49) Yeah. You know Ryan?

(Chad Fowler at 00:38:50) Yeah, from Basecamp now.

(Joel Beasley at 00:38:52) Yeah. Yeah. So he works with—I think the top three people at the Basecamp are David, Jason, and Ryan. They kind of work together.

(Chad Fowler at 00:39:01) Yeah. That sounds right.

(Joel Beasley at 00:39:02) So I wasn't going to bring it up, but I'm curious to know now because of what you do with the constantly reviewing stuff. So we have—I've been doing the show and the book and stuff for the past year, right? And all the conversations that we've had, I've learned so much talking with all these CTOs. And then I've been out of product for the first time in my entire life, like, not actively designing a product for, you know, almost a year. And that kind of is something I also love too. Like, I don't just want to completely let go of it, right? So I had this series of calls, like, five or six calls back to back with CTOs who were experiencing rapid growth, and they just kept bringing up this type of conversation about finding great leaders or, as they expand from thirty, sixty, ninety, like, how do they cultivate leadership? And that was the topics of conversation that we were having. And I get a lot of feedback from the book about leadership. And then I read a lot of leadership books because I'm personally very interested in technology leadership. And then I decided that we're going to do this startup using all the principles we have about the market and how we bring value to the market. And actually, the opposite is not taking VC and going for your first customer. So the idea is that we will go—the value has to be great enough to the market that the individuals in the market that will be customers of your product will actually exist in the market because there's such a demand. And then we have to be okay with what the market says.

(Chad Fowler at 00:40:32) Yeah. That last bit is the most interesting thing you said, I think. We have to be okay with what the market says. And maybe that is one of the top things that founders don't get that I talk to. The ones that aren't making it and that ultimately don't, I think they're not okay with what the market says. They have an idea, and they're so passionate about the idea, they become myopic. And if you don't know that word—

(Joel Beasley at 00:40:59) It's next week's word for you.

(Chad Fowler at 00:41:01) I love myopic. Yeah. They become myopic, and they can't see that maybe their idea just wasn't a business. Maybe it's even, like I said about the other topic, maybe it's a good thing, but it's not a business. And if the market doesn't want it, it's not a business.

(Joel Beasley at 00:41:17) Well, yeah. And it can be a good thing. The market could want it and then not be willing to pay enough for it to be a business. You can want something and then not be willing to hand over enough value for your business to operate.

(Chad Fowler at 00:41:29) Right. So, you know, there might be some amount of, "Well, we're not communicating it properly." Sure. But once you've tried a couple of ways and it doesn't stick, the market has spoken, and it's time to change direction.

(Joel Beasley at 00:41:40) And it's about reducing the space between. So I'm not interested in continuing building and setting up meetings, one big meeting in like three weeks. I'm interested in two or three meetings a day. I need to get through ten, fifteen people who would be customers, and it's going to morph with potential customers because they're going to say, "Look, this is valuable. It's just not valuable at the rate you did it. We would probably have to do something like this," or "Here is what this value would mean to us." And then I would have to restructure the business in a cost production way to meet what the market would tell me. "Yeah, you know, it may not be this, but we'll give you this for that." And then I have to then structure my business and cost to see if it makes sense to bring it to the market.

(Chad Fowler at 00:42:23) Yeah. It makes sense. It's a fun experiment.

(Joel Beasley at 00:42:25) Yeah.

(Chad Fowler at 00:42:26) I'll have to have a look.

(Joel Beasley at 00:42:27) Yeah. I mean, again, I just—the other reason I really like it is because it gives me the excuse to be constantly extracting leadership lessons out of these great books. By the way, I'm going to extract a leadership lesson out of your The Passionate Programmer book.

(Chad Fowler at 00:42:43) Excellent. Yeah. Let me know what you do.

(Joel Beasley at 00:42:45) Because, I mean, I like you, Chad.

(Chad Fowler at 00:42:51) I like you too. Let's make this awkward.

(Joel Beasley at 00:42:54) Let's do it. Yeah. I think Jake can edit even some music in there that'll make it even, like, get more attention.

(Chad Fowler at 00:43:02) You know, if I had video, we could really make it awkward by sitting silently for a while and just looking at it. It wouldn't translate to audio very well, I don't think.

(Joel Beasley at 00:43:11) Oh, man. I'll flip your—I'll do something with your picture maybe. Like, make the eyes go back and forth or something. So if there's any—is there any way I can bring you value off the top of your head? And if not, anytime that ever comes up that you need to use me or leverage me or the platform, whatever it may be, you just let me know because I'm here to serve the market, and you, my friend, are part of the market.

(Chad Fowler at 00:43:40) Well, thank you. I am out to help startup CTOs. I want to know them, and I want to help them in whatever ways they want. So if you help them know that I want to do that, then I'm happy.

(Joel Beasley at 00:43:53) We get an insane amount of outreach. I get—because the book that I wrote, people find from going from developer to CTO. It's like a very specific path that they're looking for. And currently, when they're searching those terms, they get my articles and they find the book, and then they buy the book, and then they reach out to me because I'm constantly engaging with people and asking them what they think and, you know, wanting to provide them value. So if there's any way that we can think, like, I can pass them along to you or you could pass people along to me to help—I currently have no business model, by the way. This is a passion project as my sort of way to give back to the world from my previous technologies that I've been able to build and do well from. So, yeah, this past year I have just built a team, got an office, have a studio, do it as professionally as possible. We currently have four or five people on the team, four people in house. And then I was like, if I build a megaphone and bring the market enough value, then the market will—it'll work. You know? Like, something will come up. An opportunity will arise, and then I'll have a chance to even give back on a larger scale.

(Chad Fowler at 00:45:13) Yeah. Well, you know, I'm in a fortunate position that I personally don't have a business model other than being employed right now, but I'm able to be employed by a company that cares enough to allow me to just be out helping people and getting a salary for it, me and my team. So we're in a similar situation in a sense, although I have less at risk perhaps.

(Joel Beasley at 00:45:38) Yeah. I don't know. I do risk in a way that isn't risky, if that makes sense.

(Chad Fowler at 00:45:46) Yeah. Yeah. In our field, it's hard to really screw yourself up too bad.

(Joel Beasley at 00:45:51) Yeah. Yep. I only risk what I'm willing to put into something. And I don't do the bottom of the ninth thing.

(Chad Fowler at 00:46:01) You know, good advice to everyone, I'd say.

(Joel Beasley at 00:46:04) Yes. Avoid bottom of the ninth guy. The person who has experience continually getting out of tough situations is putting themselves in difficult situations. It's just a different way to look at it, right? Oh, that guy has a lot of experience in a ton of horrible situations. We want him on our team. Hold on a second, guys. Maybe that person's putting themselves in there. Two questions to wrap it up. The first question is, if you go back in a time machine, you get to hang out with Elon Musk. He has a time machine. You go back and get to talk to yourself ten years ago at thirty-four, right? Almost four days to the day, and you get to give yourself a piece of advice. What would it be?

(Chad Fowler at 00:46:48) Oh, ten years ago. For a second, I thought you were going to somehow weave Elon Musk deeper into this, and I'm glad you didn't.

(Joel Beasley at 00:46:56) Surface Elon Musk.

(Chad Fowler at 00:46:58) So yeah, if I had a time machine, I'm talking to myself ten years ago. I think, what was I doing ten years ago? 2008. I would tell myself to more quickly get myself out of the business of trading hours of my life for money.

(Joel Beasley at 00:47:17) Oh, that's such a good one. Yes. Keep talking.

(Chad Fowler at 00:47:23) I knew you would like that one, but that's it. I mean, we're all—even my book, The Passionate Programmer, is really geared toward people who are trading hours of their life for money because that was my mindset, and that's the mindset of most human beings. And actually, the fact that I even say that comes from a place of privilege, you know, because I'm able to risk enough to think the way I do now. But here's an example of something completely irrelevant from a specific to CTO perspective. In the last several years, sort of by bad luck initially, I have found myself being a landlord of rental houses. Had I started that longer ago, I could retire right now, probably. Not that hard, and it's not something you have to be rich to do. So that sort of thing, you know, thinking holistically about how to set yourself up so that you're free, I think is the advice I'd give myself.

(Joel Beasley at 00:48:27) Yes. That's it. I just say yes to that. Yes.

(Chad Fowler at 00:48:33) I agree with myself.

(Joel Beasley at 00:48:34) Yes. I agree with yourself too. And then the last thing is, people want to find out more about you. I see you're pretty active on Twitter. Twitter better than LinkedIn to reach out to you and say hello?

(Chad Fowler at 00:48:47) Yes. Much better. I reply to all tweets directed toward me. And LinkedIn, I reply to very few of them, but I accept every invitation on LinkedIn. So please find me on LinkedIn and add me as a connection because I want to have the most connections of anybody on LinkedIn. That's the only reason. No. That's it. Yeah. I probably won't talk to you on there, but I want to be your friend.

(Joel Beasley at 00:49:17) You want their integer?

(Chad Fowler at 00:49:19) I have 6,565 connections on LinkedIn.

(Joel Beasley at 00:49:24) Oh my goodness. Do you really?

(Chad Fowler at 00:49:26) I mean, that's pretty lame. That pales in comparison to my Twitter numbers, but here, I'm accepting 19 more right now.

(Joel Beasley at 00:49:34) Dude, Chad, I'm looking at your picture on LinkedIn. Why didn't we have video? You look like a rock star.

(Chad Fowler at 00:49:41) Oh, I am. No, I'm a jazz star, actually. Yeah.

(Joel Beasley at 00:49:47) Yes. Alright. That was great. Thank you so much, Chad, for coming and hanging out, man. This is awesome.

(Chad Fowler at 00:49:53) Oh, thank you.

(Joel Beasley at 00:49:54) Ever in Arkansas—I'm actually going up into Murphy, North Carolina to the mountains this weekend for some hiking with the family. But the next time, I'm going to look at your conference schedule or follow you on Twitter to find out when our paths will cross at a conference so I can get a high five and say hello.

(Chad Fowler at 00:50:11) Alright. Good. And a selfie, obviously.

(Joel Beasley at 00:50:13) And a selfie, of course.

(Chad Fowler at 00:50:15) Yes. Alright then. Thank you.

(Joel Beasley at 00:50:17) Thank you so much, Chad. You have a great day.

(Chad Fowler at 00:50:19) You too.

(Joel Beasley at 00:50:25) Thank you so much for listening to the Modern CTO Podcast. Share this. Get the word out. Thank you guys so much. I couldn't do it without you. I appreciate it. You guys are the absolute best.