Founders Talk – Episode #74

Intensely focused on building a software company

featuring John-Daniel Trask, Co-founder & CEO of Raygun

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This week Adam talks with John-Daniel Trask, co-founder & CEO of Raygun. Raygun is an award-winning application monitoring company founded by John-Daniel Trask (better known as JD) and Jeremy Boyd in Wellington, New Zealand. They have revenues in the 8 digits annually, and have done it with very little funding (~1.7M USD). Today’s conversation with JD shares a ton of wisdom. Listen twice and take notes.



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I think one thing that’s interesting, John-Daniel, is the business you’ve built, from where you’ve built it. I’m here in the U.S, Houston, middle America, and to compete with on a global scale, you’ve done an amazing job building the company. I think the one thing we want to talk about today is that journey for you - where you’re from, and maybe the perspective of doing what you’ve done and the struggles you’ve had from where you’re from; not so much the country, but just not in Silicon Valley. Having to battle some of the Goliaths that might be there. Where should we begin that story for you?

Well, it’s gonna be a long story, which is gonna suit the podcast format.

But yeah, I’ll just start by just giving a little bit of my history. I was born in a town in New Zealand called Palmerston North, and it makes the town I’m in now look really big. It was about a 35,000-40,000 person town. When I was about eight years old, my father bought us a family PC in ’90s. It was a 486SX-25 with 8 MB of RAM and 213 MB of hard drive… And I can almost still tell you how every kilobyte of that disk was allocated, as I was always trying to find space for a new game or programming thing… Because 213 megs was pretty constrictive…

And at about nine years old – this was the Windows 3.1 and Microsoft DOS sort of days… And I just was going through the commands; every command that there was in DOS. So mem, edit, whatever. And I kind of got to QBasic, and I was like “Okay, this looks like edit, but there’s run, and other things in here.” So I started reading the documentation, because this was obviously pre-internet… And I realized I could write programs in here. So I started writing a couple of little programs, and it just blew my mind.

The way that I’ve always described programming to me was that I was a kid that was just mad into LEGO… And in particular LEGO Technics - the cogs and axles, and all that stuff… And you know, you’d always be begging your parents, “Can you buy me this? Can you buy me that? Can you buy me this?” And it’s like “No, that stuff’s expensive.” But discovering a programming language was like finding a box with an infinite number of LEGO pieces, and just being like “Okay, whatever I wanna build, whatever I can dream up, I can do it in the computer, and I don’t have to ask my parents to buy another if statement. I can just do this.” And if I can’t fit it, if I can’t figure out how to do it, it seemed to me that that was a limitation of my grey matter, not a limitation of the computer.

[04:22] Now, I know obviously performance and things have improved, but you could still try to figure out better ways to use it. So I kind of fell deeply, deeply in love with software development at around. And I often say to folks – because people would say to me, “Oh, JD, you learned to program at 9. You must be really clever”, and I’d say “No. The way to think about it is a nine-year-old with no external help could read a bit of documentation and do this.” You shouldn’t put programming on a pedestal, you should say to yourself “It’s actually that easy that a nine-year-old can teach themselves.”

I think we’re starting to see that sort of mentality shift away a little bit as computers and the tech industry have become just a way of life, versus how they were in the ’90s. But that really started me off on the journey. And then I was always a kid that was always sort of looking ahead… I was in a hurry. I always wanted to start in business, make some money… I remember buying cardboard boxes with my brother and working out just how many and $1 and $2 coins I could fit in there, and how much money that would be if we could just fill it up as fast as we could… [laughter] Never did fill it [unintelligible 00:05:22.15]

But you tried.

We did. We did try. So I was like “Oh, I wonder if there’s any future in software…” Again, pre-internet, I put in my Encarta 94 CD-ROM, and I typed in “software”, and it brought up this article about this guy Bill Gates. I was reading that, and I was like “Oh, this guy seems to be doing alright out of software. Maybe there’s some money in this passion that I’ve sort of discovered for myself.”

So that meant that probably from about the age of 9,5-10 I had a pretty good idea that I wanted to enter the software industry. I knew that I wanted to own a business… I didn’t know what the business would do, I just kind of knew that these two things would intersect in a big way. And then through the late ‘90s I sold a software on floppy disks at my high school, and I ran a PC repair business… Most cities now have that mobile PC repair folks that drive to your house, or something… I used to do that in like a 1970-something Subaru, just the most budget car you’ve ever seen.

I applied for one job at the end of university, and I thought “Look, if they hire me, I’ll learn what a real business does. And if they don’t hire me, I’m just gonna keep doing what I’m doing.” And fortunately, they did hire me. So I went and I spent three years seeing what a real business looked like, before striking out on my own.

That’s a lot of history right there, and we’ve only just got to the start, so… [laughs] I’ll take a small breather. But yeah, an obsessive kid would be the way I’d describe myself.

One thing you point out is this infinite box of LEGOs, and I think that’s an interesting perspective to consider… Because logically, that makes sense, because there is no real limit to software. That’s the cool thing about software, unlike hardware, where you do have physical limitations, you’ve got Moore’s Law to compete with, you’ve got CPUs, you’ve got RAM restrictions, you’ve got hard disk restrictions… But with software, I suppose you’re bound by those limits, but that’s the challenge, is to get around, and through, and over all those obstacles.

You must have been a pretty wise nine-year-old to have that philosophy… Where did you get that wisdom? Dumb luck, or did you have some true influence in your life?

Well, my parents did run a business. My father was a [unintelligible 00:07:38.14] worked from home… So that did lead us to talk about a lot of things around finance and business at home. So that definitely had an impact on me.

I’ve often wondered a little bit about this, and I kind of feel that the core – and I don’t really know where this comes from, but in my core, I tend to believe that, as much as I wish there was an afterlife, or some sort of thing, it’s like, you’ve got one shot; let’s do this. If you were to go down to [unintelligible 00:08:11.07] it’s like “Okay, we’ve got a limited amount of time. We wanna do something cool.” And I did fall in love with those [unintelligible 00:08:19.21]

[08:21] I also – not really when I was nine, but once we did get access to the internet, and I could start learning a lot more… Going back to that point about software vs. hardware - learning about people like John Carmack in the game industry, and how he had pushed forward the gaming in graphics envelope in the ’90s - that really inspired me too, as that sort of “Wow, the human brain can overcome the physical limitation, if you apply yourself to those problems.” So that sort of always felt to me – and I do feel a little bit like nothing is really impossible.

And to use the Bill Gates line - and I don’t think people ever really properly paid enough attention to the fact that he repeated this the whole time, which was “Never stop believing in the magic/power of software”, and it’s so true. I still think we’re only merely scratching the surface of what is actually possible with it.

Yeah. Well, you mentioned Bill Gates like it was no big deal, right?

To some degree, right? Bill Gates is probably the biggest person in many respects in software; one of the bigger successes…

Well, it was kind of funny… The other day somebody was on Twitter and they were like “Oh yeah, people hate Jeff Bezos, but we never felt that way about Gates.” And I’m like “Are you kidding me?” Gates was vilified in the ’90s.

He was ruthless, yes.

[laughs] Yes. And even in high school I was buying books… One of my first books was actually “The Microsoft Way”, and it sort of walked through Microsoft up until about ‘97, I think. And that was an interesting book, because it covered, for example, in that time, that they were just crushing everything. Kind of like Amazon a little bit today. If there was even a rumor of entering an industry, that industry’s stock prices would all collapse. It was like “Oh, here comes big, scary Microsoft.” And the book really digs into how – and I do think it was the first time they really slipped… It was when they tried to take out Intuit. And they threw everything of Microsoft money trying to win the personal finance and small business space… And they lost. And they lost to a small competitor. And they did try and throw the kitchen sink at them. And this book really cataloged a lot of that, which was super-interesting to me.

That’s one story I’m not familiar with. What’s the most interesting pieces of the story?

Well, imagine Intuit wasn’t an upstart by any stretch; they were still a significant business, but they were effectively an ant compared to Microsoft. Well, imagine if somebody came along today and they said “Oh, Amazon’s gonna go into competition with them”, and Amazon tried to do everything as anti-competitively as possible, and still lost. That’s when you kind of go “Oh…” What’s the line from The Avengers movie? If you can make God bleed, that’s all you need to do. People will stop believing.”

Intuit. They were TurboTax, QuickBooks… And I suppose they eventually acquired Mint, right?

So they became a Goliath, as you mentioned, in the personal finance and tax space.

That’s right. And Microsoft was absolutely trying to obtain that category. They even, I believe, tried to acquire Intuit back in the day… But yeah, I found that interesting.

It’s funny, I’ve never really been a person that’s wildly into sports, and last year I was delivering a speech to my old high school for the folks that were leaving… And they talk a lot about – because I knew I was an odd kid, that I knew exactly what I wanted to do, and I realized that was not common… So I said “Who here knows what they wanna do?” There were about 400 people that were graduating… And I would say less than 5% of the hands went up. That’s what I kind of expected.

[12:08] And as I was leaving, I had this realization that for high school - which, in New Zealand, high school is the last school before you go off to university, if you go off to university - it’s less about the what, but I think that high school is focused heavily on what do you want to do. And I don’t think a lot of them realize that most people [unintelligible 00:12:26.06] business is just competition. If you thrive, you like to be on a team and you like to win, it almost doesn’t really matter what it is that you’re doing; the what is far less relevant than maybe the how.

And in particular, I went to an Old Boys school, so this was 400 boys. Shifting that sort of framing to the fact that it’s kind of like you’re playing a sports game for eight hours a day, five days a week, that sounds far more exciting than “Do I wanna clean drains? Do I wanna wash cars? Do I wanna write software?” That’s actually quite hard; but where you derive your value is competition, I think.

Or at least for a subset of us.

And not everybody has that feeling. I know that some people thrive in competition, and some people just – I don’t know; maybe it’s not part of their DNA to compete. I suppose that’s, to some degree, competing by not competing, right? Because you sort of forfeit it.

What’s interesting, I think, is that you called yourself an odd boy in the fact that you knew what you wanted to do. And I guess my question to you is really 1) how did you know? You’d mentioned that 5% of the hands gone up, and how you sort of expected that, so that means that you have a predisposition, that you think that those coming out of high school on their way to university, 5% seems like a number to think about “Hey, I know where I wanna go in life, and what I wanna do.” Because I think – you know, do we begin life knowing what we wanna do in life? I think that’s kind of the journey; it’s like, what’s the end game, to some degree… And even in many ways our whole life is about choices; we’re the sum of our choices. We’re also the sum of who we surround ourselves with.

Oh, yeah…

So in many respects, people don’t think about how important and how influential their crew is, so to speak; their inner circle, their family, their friends… This is super-crucial stuff. But yet, you knew what you wanted to do.

You walk into some categories here that are, I think, difficult to discuss, especially if we’re in a forum like Twitter, because there’s a strong narrative of like almost “I have no agency over myself. Everything has happened to me, and therefore everybody else somehow owes it to me to fix this.” And I think there’s a lot of people that are gonna spend a heck of a lot of time in their life blaming and not taking action.

Now, that is not to say that folks do not necessarily have systemic or other issues holding them back. The mistake is thinking somebody else is gonna fix it. I’m not saying those things don’t exist. But you hit on a really interesting one there, around who you surround yourself with… And I’ve been pretty militant on this point, even through my teenage years… And I’ve heard a saying once - you’re the average of the five people you spend the most time with… And I don’t think it’s wildly shocking that some of the folks that seem to have the most challenges or seem to have the most problems, and then you look at the folks they associate with, and you sit there going “This is an entire system set up to hold you down. You are choosing to stay in there.”

Now, there are times when you don’t have a choice. I was very fortunate to have wonderful parents, fantastic siblings. I had a great experience being raised. I was very fortunate to have the capacity to play with a computer, to have the free time for that. There were certain privileges. But once you’re out in the world yourself, you do have a strong ability to then choose who you spend your time with. And it may sound ruthless, but there are certain people where I’ve sort of started to become friends with them and then gone “Actually, you know what - this is not gonna take me where I want.” And I’m not talking about just a business goal; I’m just talking about “Do I really want to dwell on these topics day to day? Is this where my mental cycle should be going?”

[16:23] And probably because I was a bit of a nerd as a kid, I often think of myself a wee bit as like a computer. I often just think, okay, let’s say your brain was the CPU. And like I said, let’s say you broke it down. Why would you choose to allocate a certain percentage of your CPU cycles to something completely non-productive or effective for you? That’s just a waste of tim. You wouldn’t run an app on a computer today just to burn out one core, because you felt obligated to do it, but it didn’t give you anything in return, right?

So it can sound kind of – I don’t know. It sounds negative, it could sound ruthless, but frankly, the people that are bringing you down, get rid of them. The people that are helping you up, double down on them. I was always very aggressive at trying to find people that were maybe 5-10 years older than me, that I could learn from, that could teach me. That first job that I got out of university, my first thing that I was – I was like “Alright, who owns this company? Who are the directors on the board? Who do I wanna understand how they’re thinking? Because this is going to help me better understand what we’re trying to achieve here, and it’s gonna help me basically not smash my head against walls that aren’t gonna move, because you get to know what they actually want to achieve in this business.”

I know some of these things – you get people that kind of go “Wow, how did you think that?” It’s like, you just look at the situation. The business is here, you have shareholders… Everybody knows that’s how business kind of works, right? Like, what do they want? Because that’s why it’s here.

Yeah. People underestimate mindset. They underestimate mindset, which is what you were studying there - a mental framework. Who owns the business, who are the board of directors, what do they want, what is their mindset, what is their mental framework… And then also the environment, which is those you surround yourself with. People underestimate the impact of those three things - how you think, which is the soil of your brain; the things you think and how you think, your mindset, your mental framework, that’s the soil from which you grow your life. Your brain is what powers everything you do. It makes you you, right?

And then your environment. The environment you place yourself in, those you surround yourself with - people underestimate those key factors there. And back to what you had said before in terms of circumstances, and the environment on Twitter, and the fact that people wanna blame other people, or in your words back to you, “Someone who’s gonna solve their problems for them.” I think you’ve gotta take some charge; take charge of your life in those regards.

And there’s some circumstances where there’s obviously some details that need to be fleshed out, but in the grand scheme of things, you are the product of your environment you place yourself in, and the choices you make.

And you are also the product of the challenges, problems and opportunities that you do inherit.

Sure, absolutely.

But you do gain more and more say over yourself with time. And I think that’s the thing… You could sit down and you could draw a line down a piece of paper and look at the things that you can and can’t control… To give you an example - again, in that first job I started as a graduate software developer. I moved to Wellington with $200. Because frankly, while I’d made a little bit of money through high school and uni with these jobs and things that I’ve been doing, the side hustles, I was also quite aware that the last vacation at the end of university was probably the last time I was gonna get two months of nothing until I retired… Which I may never do. So it was kind of like “Alright, I’m going out big here. I’m gonna spend everything I’ve got.”

[19:54] So I moved down to Wellington with $200 in my pocket, I got this job… And then, of course, I’m in an environment, and you’re going “Okay, so what do the shareholders want? Okay, cool.” Now, somebody might go “But what if I don’t want what the shareholders want?” Well, the next thing I did was kind of go “Right, we have a staff share program. How many shares do I have to buy in this company before I could start to make a credible argument for pointing me to the board of this business?” I do wanna have a say on the environment. Firstly, I don’t wanna alienate the people that are the directors and operators of this business. Secondly, I wanna find a path so that I can be one of the directors and operators of this business, start to look at the shareholders list, figure out who I’m gonna have to try and buy out, figure out how I’m gonna get the capital to do this…

I was fortunate that while it was a fast-growing business, it wasn’t a massive business, so it did look like it was something that was within my capability to do over a few years. And the other thing, too - I’m gonna keep coming back to Bill Gates, since we’ve touched on this topic…

I like it.

…but he has this saying where he says “People overestimate what they can achieve in one year, and underestimate what they can achieve in ten.” And you see that all the time, which is like “Well, if this is gonna take me –” And to be fair, I can almost segment a little bit… Well, it’s probably worth saying for a handful of people that may be very upset hearing some of these things - these are all broad generalizations. There’s always an exception to these rules. But generally speaking, I’d say that the more success somebody has, the longer-term horizon they took. There will be people that go “If I can’t end up influencing this business or whatever this situation might be within one month, then it’s their problem. And it sucks.” Maybe it’s one year, maybe it’s three years. There was no way a guy with $200 was gonna buy a meaningful amount of equity in the business right at the start.

And somehow you did.

Actually, there’s a story there. I got so much –

I assume you did, at least…

I got very close, and then there was one shareholder that I needed to buy out, who had agreed he’d leave the business… And he said “Okay.” It was just a verbal, and then he backed out. And his reason for backing out was actually that he had retired, and this was one of his last things that connected him back to the working world, and he loved the excuse that he got to kind of rock into the office and chat with people. So I really didn’t begrudge him on sort of going back on that… But that was actually the turning point where I thought “Look, I’m not actually going to achieve this mission here. If I’m gonna do something, and I wanna be in charge, I’m gonna have to strike out on my own here.”

So at that point was when I went to two people; one of them was my co-founder for a short period, so I won’t dwell on that. But the other guy, his name is Jeremy Boyd. So just to make our company really good today, the co-founders are JB and JD, and we have an internal joke that if your name starts with J, you’ve got about an 80% likelihood that we’ll hire you in the recruitment process…

Anyway, I said to him, “Alright, we’ve gotta go do something ourselves”, and he’s like “Yup, alright. Let’s do this.” And so we struck out and started our business there. And to be honest, I wasn’t upset that I couldn’t get to where I needed to in the last business. I understood that guy’s point of view. It was just the right time. I’d saved up a lot of money through those few years, because I’d been so obsessed with trying to buy stocks.

I will say, my mother, when I first started down here, she’d bring me up and just tell me, “Hey, look, you need to enjoy your life. Go and spend some of what you’re earning on stuff that you want, like a mountain bike.” And I was like, “No, no, no. I’m not gonna spend any money.”

And it’s probably worth noting at this point that I would describe myself as aging down. 13 to about 25-year-old JD was a pretty serious dude. I was the guy at university that had a briefcase and a college shirt. I was that idiot. I was the guy I’d probably tease now. I didn’t own a pair of jeans until I got to about 30 years old… And now that I’m in my late 30’s, it’s kind of like pretty [unintelligible 00:23:53.24] But in part it was because I was really focused on “I want to build up this machine. I need to get this. I need to stay focused on this. I wanna be really good at it.”

[24:07] Even when I was working as a software developer back at that first company, I would come home every night and do about 3-4 hours of extra work just learning, because I didn’t like the fact that I was the guy who’d been coding since 9, and suddenly I didn’t feel like I was the smartest guy in the room anymore. And I actually somewhat enjoyed that, because it brought out that sort of fight in me. I was like “Right. Well, I’m just gonna learn faster than everybody else. I’m gonna win. I’m gonna do this.” And that’s always part of my psychology, and it’s not always healthy…

To use my mother as another talking point, she reminds me that – I have a younger brother; he’s a year younger than me. And he got a wiggly tooth before I did. And my brother goes “Oh look, my tooth is wiggly.” You know, cool… And we go to bed that night, and I come out at like nine o’clock at night to tell my mom that my tooth has come out, because I apparently – I don’t remember this… I had apparently laid in bed and ripped a tooth out of my mouth to beat my brother… And she said I just had blood pouring out of my mouth, and this tooth… [laughs] And going “Now that I’ve beat him…” [laughs]

So you’re relentless. By any means necessary, you will do it.

I don’t know if I’d rip a tooth out these days, to be honest. Again, maybe the aging down, but… [laughs] Now the teeth aren’t gonna grow back, so they’re a little more valuable. [laughs]

Right. So at what point then – and you mentioned JB is your co-founder at Raygun…

We’re at that point of the story now. So why error tracking, why error monitoring? You’d mentioned university - what did you study there? This first job - what were you doing? How did you get to this space in particular in software?

Yeah, so we actually didn’t start off there. We started off building some other software development tools… And you know, this was where things actually got murky, because my vision for my future was to own a software business. I didn’t actually know what it was gonna do. In a weird way, my goal, my purpose to be the owner of a software company had been with me for about 12-13 years at this point… And once I got there, it was kind of like “Hey, hang on a minute… Now what do we do?” All this time thinking about this, and I kind of got to this point…

So we actually muddled around for a few years, building different things… They were liked products; we could wipe our own face. The business was making money, which was good. But we also did some – we bootstrapped the business, so we did consulting work… We actually had Microsoft New Zealand come to the party on day one of founding our company and give us a quarter of a million dollar contract. And that was really our seed capital.

We built some software for Microsoft that demonstrated how teams should build modern web apps, and they used that as demoware around the world. Now, that actually came out of the relationship that Jeremy had built with Microsoft New Zealand. And this goes back to your point of who you associate with, where are you investing your time. He was putting a lot of his time into supporting the local software development community, running user groups and all of that… So he was well-known and well-liked, and generally appreciated in the local software community. Surprise… It worked out for us.

And to use that famous Steve Jobs quote, “You can’t connect the dots looking forward. You can only connect them looking back.” Jeremy wasn’t supporting the community because he wanted a deal out of it; he was doing it because that’s what he loved to do, and then this positive came. So he had actually put in not expecting anything out, and then got something out of it. And that was hugely valuable to us.

[27:49] Over those few years we also partnered up and built other companies. So we were fairly well-known as being a pretty good software development team, high-performance software, good outcomes… But we took equity in those companies. So we built New Zealand’s largest philanthropic website as the technical partner, where we owned a part of that; we built a business valuation SaaS company, we build an email mining software company… We did a few things like that on the side. That was all good.

In 2012 we decided we were gonna build the error tracking software, and that we were gonna call it Raygun. Now, our company at this point had actually been called Minescape… And I’ll tell you want - nerds naming companies, man… How did we come up with the name? I mentioned we had three founders at the beginning… And we basically all just came up with these names, put them in an Excel file, ordered them, and them we all scored them one to ten, and then we added those three rows together and sorted the sum, and then we just went with the top one, which was Minescape.

And I remember there was this one right down the list, Raygun… And I just remember thinking – well, it was actually Railgun, but anyway… It was from JB, and I just remember thinking “That’s the stupidest name for a company I’ve ever heard of.” [laughter]

Oh, yeah…

And we were trying to come up with this name for this product, and it had now been like five years or something (4-5 years), and it had always stuck with me. And I was like, “You know what - the fact that I keep thinking about this must mean that there’s some intrinsic memorability to this name.” So we called it Raygun. I thought Railgun was a touch too esoteric maybe towards the gamer community, that maybe played things like Quake and Unreal… But to a more normal person, they wouldn’t know what a railgun was, so that’s why we went with Raygun.

You got me, I must be normal then, because I don’t know what a railgun is.

So railgun, in a basic sense, is where you take a metal rod, you coil wire around it outside of it, and effectively use an electromagnetic pulse – sorry, you electromagnetize the coil to force the projectile out very quickly. They are actually deployed these days on some of, I believe, the U.S. – I’m not a military guy, so apologies to anybody where I get this wildly wrong… But a couple of the battleships and whatnot that the American Navy have - they can fire very long ranges, very strong projectiles from them. And therefore, in the ‘90s and in the early 2000’s they were common in computer games. But generally speaking, you’re not running around with a handheld railgun. They’re more mounted on a ship… But anyway. Complicated to explain. It doesn’t sound like error tracking at all…

But we built the error tracking software because we were reflecting a little bit on how we had built software in the past, and why was it that the software that Jeremy and I wrote was generally considered to be higher-quality than what some other folks did. And I don’t believe that for a second that it was because we were somehow just better programmers… It was because we had always instrumented our software to tell us about the errors, and it would just send us an email. We did this back in 2004 when I’d started at this company; I actually learned it from Jeremy. So we thought “Why don’t we build an entire product around this?” Like a workflow, and make it so other people are like “Surely if we find this useful for getting in front of bugs before customers even realize, then that’s a good thing.”

And so we built it, we put it into market in 2013, and it went out the door, and we just at the time thought of it as one of the many products in our catalog. I will say, recurring revenue versus one-off sort of stuff - oh, my goodness; my hair is thin, but I would be bald if it wasn’t for recurring revenue. Starting the month at the end of where last month was, rather than starting the month at zero and having to try and get up - it was a powerful mechanic for our business.

Anyway, we put that out, and later that year, around August of 2013 we got approached by a mid-sized U.S. tech company to acquire our business to obtain the Raygun software. And that was the moment where Jeremy and I – again, we’d bootstrapped to this point. We kind of sat back and went, “Hm… We might be on to something here.”

[32:03] It was a little bit different. We had actually sold off some of those other businesses that we’d built or been part of building, but we were like “Oh, okay, we should raise a little bit of money and try and go a bit quicker here.” So we did.

We went out and raised at that point 1.3 million dollars, kiwi. So it would be about 700,000 USD… So, like, nothing. And as part of that, the people that invested were actually more or less the folks that we’d built those other businesses with. They were like “This is our time to invest back with you guys. We know and trust you.” And that was pretty cool. I really appreciated them.

It was also – I’ve been told before by some folks that are generally more successful than me that this was a bad idea, but I was one of the largest investors in our own round… Because you always hear the question about “Oh, dilution” and “Founders made bad decisions because they don’t wanna dilute, but actually the value at the end is better” etc. And I was like, “Well, the best way to try and reduce my dilution is surely just to invest alongside everybody else.” And so I did that. That’s worked out well, and the business took off. It really took off for us.

And I know the video is not gonna be in the podcast, but effectively, imagine your classic hockey stick. As much as I hate talking about hockey sticks, there’s actually a really, really interesting point in here, which was there’s this inflection point, and people would say to me “What happened there?” And I’d say, “Well, that’s when we raised money.” And they’re like “What did you spend it on?” and I was like “Nothing.” They’re like, “What do you mean you spent it on nothing?” And I was like “We didn’t spend it. What we did was – it actually just gave Jeremy and I the confidence to ignore all of our other products and just focus on the Raygun product.” Because now we had this buffer that we could afford to ignore the other products. And just the act of then having the entire team in the company - and it was only like 5-6 of us at this point - focus on Raygun was what generated that revenue uptick; the growth took off, the awareness blew up.

We then – you know, the classic thing, “Good luck begets more good luck”, we got a great write-up from somebody in the industry who didn’t even… They actually knew us, but didn’t know that it was from our company at the time, and they wrote this amazing review online, and they had a very popular blog, and that exploded the customer base for a good few months. And really – I know we’ll talk about it, but effectively, the rest was history.

So yeah, that’s kind of what led us to getting to where we are today.

Intense focus. That’s interesting. So you hear these stories about “What could you do if you focused on a certain problem?” But that’s really interesting, that your uptick was based upon raising money and not spending it… But having, I suppose, the assurance (you said confidence). What I do these conversations for is for nuggets like that; to hear somebody say “My success today, one big portion of it was because we intensely focused.”

Yeah. The thing that was interesting to me with that - and I think it’s probably what you’re trying to say here - is I read this all the time. “Say no to things” etc.

And I hadn’t actually had ever had a time where I could point to something, where I could say “Applied focus got this result.” You could kind of muddly assume it was working in places, but it was never as stark as that situation.

I always find that interesting. I read a lot of books, and there’s books I read where I said “Man, I wish I could just internalize every word of this”, because in theory if you actually read books and retained all of the knowledge, we’d all be super-geniuses pretty damn quick… Which is actually why I’m a big believer in reading the good books multiple times…

Oh, yeah.

[35:59] …because I think what that does is it actually starts to strengthen various neural pathways. And I won’t say “Oh, I read this, The Microsoft Way, in 1998” or something. I’ll think I came up with an idea, not realizing that those pathways were already set from reading something in the past. I’ll probably think I’m really clever for coming up with it, when it’s actually straight from a book. But I’ll never remember the book. So… Re-read the books.

You were onto something with psychology, because that’s called neuroplasticity.

Right, yeah.

And your neural pathways - you know, neurons that fire together, wire together.” So the more you run those neural pathways, the more strength they have to continue running. So imagine if you just keep building this road and refining it and making it easier to go faster from point A to point B, and you constantly refine and optimize. That’s what you’re doing with neuroplasticity. So when you re-read these books, which I totally love - that’s a great idea - my question back to you is which books have you read multiple times and have been your favorite? So two books, one book, any book. What’s your favorite to read twice, or three times?

It’s a good question.

I’ve got one…

Yeah, what would you recommend, first?


Essentialism. I’ve not read that one. I will write it down.

It’s not minimalism… So it’s not minimizing. It’s focusing on only the essential. The vital few, versus the trivial many. And that’s kind of what your story is, JD, in this example where you got this investment, and you had this uptick, you had this intense focus… You focused on the vital few, versus the trivial many.

That’s true.

So when you do that in life, with intention, and potentially with the right kind of environment, the right kind of people around you, you could do amazing things over ten years, versus a terrible thing in one. Re-say the quote to me again, one year versus ten year?

People overestimate what they can achieve in one year, and they underestimate what they can achieve in ten.

Yeah, exactly. And my favorite chapter of that book is – I don’t know the chapter number, but it’s called “Protect the asset.” It’s generally about sleep, so getting good sleep. But more so about self-care and taking care of you… Because you can only be the you you are if you’re you.

That is bang on. I’ve never – and I know this has become cliché these days for some folks to say “Oh no, I actually get a lot of sleep.” I’ve always been a big sleeper… Even as a teenager. I’d have LAN parties…

Oh, yeah.

You know, get together, plug them in, and I’d be the guy that - especially if I was hosting - would be like “Okay guys, it’s got to midnight. I’ve gotta go to bed.” I’d have a sleep and then I’d come back out at about seven o’clock in the morning. They’d all still be out, red-eyed, and I just – I didn’t have it in me. I didn’t even have it in me at 16 or 17. I was never a night owl. But yeah, I’ll check that out.

One thing that is also interesting was around the time we launched Raygun was when I took up running… And let me be the first to say, I am not a runner. That was a good wee while back now. I’m a plodder at best… And it is definitely a mind over matter situation.

What’s a plodder? What does that mean?

Imagine – I mean, I’m not overweight, but if you saw me running and I look like I’m kind of awkwardly doing it, like I’m muddling through it…

You know, I’m no gazelle. Let’s put it that way. I’m not bouncing along. You know, you see some runners and it’s like they’re just floating along…

Yes. Feet barely touching the ground, just gliding…

[40:14] Yeah. Every footstep for me is kind of like Thor landing on Earth… Like, you know, “Let’s smash into the ground.” [laughter] It’s very awkward. Anyway…

But yet you love it.

Well, I did it because at this point I was getting to about 30, the metabolism is starting to slow down… I love computers, I have a desk job… You know, the weight is starting to come on… It’s those sorts of things where you’re going “I need to (as you say) protect the asset. This is an investment in me.” And what I actually found was really useful - running alone, and having the time to think.

I would be out running, and I’d go “Hang on a minute… I’ve missed a trick here. There’s like $50,000 we could make at work if I just did this thing.” But I wouldn’t have had the time to think about that.

Now, what I’m gonna do is I’m gonna come back to your book question just quickly… I’m a big biography reader, and I would look at stages in my life. In my teenage years I read a lot of self-help books - Tony Robbins, stuff like that. In my 20s I went to a lot of business books; usually a touch more biographical than like “Here’s how to run a business.” And then in my 30s I’ve definitely gone far more heavy on the biographies.

So the two books - and more recently I’ve read a lot of, a few times - one is The Snowball, which is a biography of Warren Buffett… It’s a huge book; if you wanna workout your biceps, buy the book. Otherwise get the audio version. It is huge. It’s a big book.

A thousand pages or so? Eight hundred?

Yeah, I think it might be eleven hundred pages. It’s a big book.

Wow. Okay. That’s a book.

Yeah. What I like about that is - look, no doubt, Warren Buffet is a shark; that dude is ruthless. But he’s also a person who has built an entire brand around integrity. And again, a lot of people won’t know this now, but there was a time in the late ’80s, early ‘90s where he actually acquires effectively a controlling stake in Salomon Brothers investment bank in New York… And they basically do some really dodgy stuff. He’s on the board, he’s on the hook, effectively. The CEO walks out and he ends up being appointed.

Now, this was before a lot of us would have been paying much attention, so we don’t know it, but he ends up having to testify to some Senate committee, and literally, it comes down to the government to choose whether they’re going to effectively kill Salomon, or they’re gonna keep it alive, and it all comes down to the fact that Warren Buffett is willing to put his reputation on the line for Salomon that he’s gonna clean it up. And the [unintelligible 00:42:47.03] committee comes out and says “I’ve told our people - if you lose money for the firm, I’ll be forgiving. If you lose one shred of reputation for the firm, I will be ruthless.” I might be screwing it up a little bit… But you know, it’s an interesting read.

I like the paraphrasing. Even if it’s a paraphrase, I love it. People underestimate – maybe that’s sort of generalizing, but I’ve even at some point underestimated the value of reputation. And what I’ve learned, I would say, in helping build this business, Changelog Media, is it’s about relationships, and that’s reputation. You can’t have a valuable relationship if you don’t have a good reputation, or worth working with. And that’s everything. It’s everything for our business, is reputation.

Absolutely. So hearing those stories – because obviously, he has to be aggressive to have created the outcomes he has… But I think the general social narrative is the people who are successful are somehow bad people. And I don’t think he’s a bad guy. I think he drives a hard bargain, and he knows what value looks like, and he’s gonna assert his position. But he seems to always act with integrity, and that has always been a key part of his success. So it’s a bit counter to the broad narrative…

[44:10] Another book that I’ve read through – well, two books really. I’m gonna end up with three. They’re all biographies, but they’re highly related… One is called The First Tycoon, and the other one is called Titan. You may have heard of these books.

The First Tycoon - the subtitle is “The epic like of Cornelius Vanderbilt”, and Titan is about John D. Rockefeller and the rise of Standard Oil. Obviously, their two worlds are somewhat connected, in that Vanderbilt was the richest person in America prior to Rockefeller… And effectively, Rockefeller really takes off in part because the deal that he does with Vanderbilt. There’s some crazy stories in there. And to put it in context, depending on which measure you use, Bezos is still pretty broke compared to Rockefeller. I think the current estimates are that Rockefeller would have a net worth of somewhere around 660 billion dollars in today’s money…

But young Rockefeller is getting into the oil trade, and he goes down to New York from Cleveland, and Cornelius Vanderbilt basically controls all the railway lines. And he’s gonna go and see Cornelius Vanderbilt. And he gets this thing saying “Cornelius Vanderbilt will see you at this address, at this time”, and he goes back and he’s like “Well, the fact he can send me a telegram says he knows where I am. He can come to me.” And this was like a 20-something-year-old upstart that’s got nothing going on, saying that to the richest guy in the world – the confidence in this guy was just ridiculous.

Now, admittedly, part of his confidence came from this personal – he was highly religious, and he believed that God had tapped him to make as much money as he could to do good for the world, and so he acted almost like a religious zealot in his own belief.

Anyway, he meets with Vanderbilt - well, actually with an agent of Vanderbilt’s - and he does this deal. And I’ll get the numbers wrong, but it effectively says “I’m gonna do 60 tankers–” well, they weren’t tankers, but “60 carriage loads worth of oil a day on your network.” And they sign this deal.

And Rockefeller has to go back to Cleveland, because he’s only producing about like 10% of that number a day right now, and suddenly he’s gotta find the product to put on all these trains… And he ends up effectively controlling the railway network because oil becomes the product that’s moving around the place.

So anyway, these two books - they’re both ginormous books. What I like about them is both the general business lessons that are in there, coupled with the fact that you get a really great history of the growth and development of New York before anything had been discovered in America. Vanderbilt starts out where it’s still not even called New York. It’s a Dutch colony, and they end up putting boats on the water. And then you kind of follow through the two books, and by the time you get to the end of it, the gold rush has been covered, the Panama Canal is under development… You actually get a history lesson.

I like those books because I’m never gonna go and buy a history book. I’m gonna buy a business biography. If I can get two things for the price of one, and now I know the history of America, that’s a win for me.

I like biographies, but I never considered the fact that they’re history lessons of (I suppose) different eras of time through somebody’s story. It would make sense that that’s the case, but I never really considered that as a gold mine in terms of like history and business all in one book. That’s perspective. And what’s interesting there, as we think about today’s time. Railways, oil - these were physical things; these were distributions, so to speak, for product. And we’ve gotta think about today, what are our distribution channels. Almost even comparing Amazon as it relates to what’s the main thing you see UPS and FedEx drivers carrying? Or even USPS drivers, here in the United States, for example. A lot of the times it’s Amazon boxes, of sorts.

[48:07] At least one or more in every handhold of a delivery person coming to my home is like Amazon. Or somebody else, my neighbor’s or whatever. So that’s the thing that’s moving things. And in many ways, Amazon has their own delivery channels. now. They’re a Goliath on that front, in terms of distribution and moving product and stuff like that.

Effectively all major companies – if you wanna talk about building (I guess today would be) a trillion-dollar business, you’re effectively trying to construct a toll booth at a critical juncture to the market. What is the App Store if not a toll booth to access iPhone users? What is AdWords with Google if not the gateway to the internet for everybody, right? They’re standing there, clipping the ticket.

And this is the thing - Amazon almost has more of these than anybody else, which is why I’m personally really bullish on the Amazon model. I mean, you look at Amazon Web Services, and there’s a common – actually, sorry, I’m going all over the place here… But the saying is “If you spend a dollar offline, some part of that is probably going to Warren Buffet. If you spend a dollar online, some part of that is probably going to Jeff Bezos.”

You see these people who go “I’m not gonna give any money to Amazon, because I don’t like how they’re treating their warehouse workers…” We could go into that one for a while, but anyway; moving past that. And it’s like “Cool, so how do you boycott most of the internet?” Because he’s making money when you go and visit Reddit. It’s on AWS. He’s making money when you go anywhere here. It’s always “How do you put yourself on those junctures to the market?”

Now, I’m not saying every business should, but if you wanna build something truly massive, you’ve gotta find those sort of pinch points.

So in terms of size then, are you trying to build something truly massive?

You’ve got some wisdom from these biographies, you obviously have some vision for where you wanna go… At nine years old you knew what you wanted to do… Are you building something truly massive? Where you’re at today in terms of Raygun and the business it is doesn’t mean that that’s where you’ll be throughout your whole lifetime. You may move on to something else… But what are you trying to do?

My personal view – I always treat everything as a learning experience. I think that there is a broadly accepted untruth that a lot of very successful people had a clarity of vision right out the gate… When the reality actually is that if you’re a strategic thinker and you kind of do a check-in frequently about where you’re at, and you adjust your sight… Again, I’ll lean on our good friend Bill Gates - he has a quote from early Microsoft, which is “One day Microsoft might be a large company. It might employ 30 people.” Bill Gates didn’t set out going “I’m going to dominate the entire industry.”

One other Microsoft story that a lot of people aren’t aware of is that their original internal motto was “We set the standard.” That was their view - anything that was gonna happen in computers, they wanted to at least be the one that’s setting the bar. And I think that was actually the signal really about the ambition. So ambition [unintelligible 00:51:21.08] but the other two kind of adjust based on the current situation.

All that is to say is that I have very large ambitions. Raygun is a part of that story for now. It may not be part of the story forever. It may still be a piece of the story.

I personally – you can probably piece together from some of the people I’ve referred to in here, like Warren Buffett… I’m a big believer in the power of SaaS businesses, and the idea of having multiple revenue streams, and things like that. So the potential to one day have a portfolio of companies that are all sort of acting in unison, or at least part of my “conglomerate”, if you will… That’s probably a little bit what I’m starting to map out. Don’t hold me to that - it might change over time - but that’s kind of what I’m thinking.

[52:14] The other thing - I know we talked about it before we actually jumped on here, but we haven’t discussed much… I’m down here in New Zealand, and one thing that’s going on here is our country is the largest exporters of agriculture. We make great meat, we have a lot of land, low population density… Software and technology is our number four export at the moment for the country, and I am a huge, huge believer that software should be New Zealand’s number one export. As you noted as well, New Zealand is tucked right down the bottom of the South Pacific. We are in a world where climate change is a thing. The miles to market is hugely problematic for us. Why would we focus on industries that play to our natural disadvantages?

Compare that to, say, my business, where it’s like “Well, we can host our data anywhere.” Time to market is measured in milliseconds. There’s very little in the way of a Carbon footprint of trying to get something from New Zealand to the world if it’s on the internet… And you even asked before we started about the challenges of getting to market. Well, thanks to the internet, it would be more work to not be an international player. A lot of people don’t know we’re a New Zealand business, to be honest. We don’t flaunt it in any major way… But this actually plugs a little bit into my own purpose, which is I would like to be a significant contributor to getting the IT exports from New Zealand to the number one spot, and being a significant component of that export revenue for New Zealand.

Now, that might not sound like the ambition of an Elon Musk or a Bill Gates or anything like that, but it’s kind of where my next steps lie… Because if I can achieve that, then the question becomes the next size of the game, like how do you take it from there.

Again - one year, ten years. What are we gonna do? [laughs]

So what’s your rough range of years for that then? Ten years, or less than that? What does it take to do that? What are some of the steps you have to take?

Well, to put it in context, if you were targeting today doing about 25% of the export revenue of the country, it would be about a two billion dollar a year revenue run rate company. So I would say you’d need closer to the ten-year than the one-year mark on that one…

But that’s the thing, I’m hungry for that challenge, and I actually do see a leadership coach; I have for a few years. And I was talking to her the other day, I was working on some of these plans that I have, and she said “Well, what do you think the next step is?” and I laughed. And she said “Why are you laughing?” I said “Well, because my immediate thought is I need to go and do these things.” And she was like “Yeah, well the issue is that successful people almost never struggle with the how. You will always figure out the how. That is kind of what’s actually made you successful. And it also means that it’s the thing that you usually wanna actually go and do, because it’s “Easy for you”, it’s enjoyable.”

You know, you go to the gym for the first time in a few years and you hate it, because you don’t work that out. But solving the how is something that you do all the time. “Okay. New problem - how are we going to overcome it? New problem - how are we going to overcome it?” So you start to overly optimize on the how, and you forget to think about the what, and is this the best what that I should be putting all of my how effort into?

Yeah. You think of them like resources, your How and What…

…and I think the other one is Why.

Absolutely. This comes back to…

Personal purpose.

Yes. And I actually touched on it a little bit earlier in our conversation - I struggled a bit with purpose, because I had this goal, which was to own a growing and successful software business. And I achieved that. But a goal is not a purpose, and I’ve confused the two of them. And then when (again) my coach would be like “What’s the purpose?” I’d just keep struggling with this question, because it wasn’t coming to me.

[56:16] And again, I’ll share a Bill Gates one… Their original one was – and it’s funny; they’ve kind of tweaked this, but Microsoft was founded based on Bill Gate’s vision of a computer on every desk and at every home. And the bit that they usually cut from that off the end was “Running Microsoft software.” That was not the bit that was in the public very much. And I was like “Man, you know what - this guy’s amazing. How do you have that clarity of vision and purpose so early on?”

Anyway… Where I’m going with this is that I learned for me it wasn’t to look at what I wanted. It wasn’t to look at it in a positive light. It was actually to figure out something that made me really, really, really angry. Because anger is a signal. Anger itself is almost a useless emotion other than to almost be like an interrupt to your brain, of like “This is important.”

Now, it may be a boundary violation, it might be whatever the heck it is; it’s kind of irrelevant. But it matters. And that was when I was like “Oh, you know what?” This is where I’ve actually focused on the New Zealand piece - I love this country, it’s a great country. I have lived in other countries. I actually lived literally over the road from day one Amazon’s headquarters for three years in Seattle. But that’s where I was like “Why the hell are we wasting all of this Carbon footprint?” New Zealand could have an amazing culture if it actually just hitched its wagon to the transformation that is the software industry around the world? And I’d kind of been a bit tepid about it in the past.

So that was when I started to go “Oh, well if I’m getting (to use the Twitter words these days) triggered by this situation, maybe my purpose is actually to try and resolve that situation, or at least be a contributor to fixing it.” That was the magic for me on kind of going “This is it.” It was figuring out the hill I was willing to die on…

Which is the struggle. I think we seem to have some direction young, some ambition maybe; that’s what really drives us when we’re younger, in through our twenties… And somehow we get to – it doesn’t have to be thirties or forties, but some sort of age of maturity. And somebody else’s version of maturity might be 25. 30. 35-40. But the point is that at some point you begin to really think about this thing of purpose, what really matters to you. Your words was “What hill are you willing to die on?” And I think it takes a little living to find that out. A little of dislike and like of life, a little bit of experience, dare I even say wisdom, to sort of gain some experience, to really truly appreciate the hill that you’re willing to die upon… And the Why, and the How, and all the things.

And this loops right back to the start, which is there are things you can control. Find the thing that actually matters to you, and then put your life’s work into resolving that thing… Rather than sitting on Twitter and raging. [laughs]

Nobody says “You know what - my purpose is to solve the issue of this orange egg on Twitter.” [laughs]

Exactly. Well, JD, one thing I think you’ve been keying on, but I’m curious if you for some reason may have a list… But what are some things that you do that keeps you sharp? You’d mentioned running, obviously you like to read biographies, you’ve quoted Bill Gates more than anybody I’ve ever talked to, which is just fine…

Oh, I could keep going… [laughs]

I bet you could, and I love that. And I like this aspect about you - you’ve got a business coach, as you’ve mentioned… What are some of the practices that you do to keep you sharp, to keep you focused, to keep you on the track that you wanna be on? I think that’s what we all want - we want to be on a track we wanna be on… Because what is a track? It’s pretty straight, generally smooth - hopefully; unless it’s a rusty track… But what things do you do to keep you on the track you wanna be on?

[01:00:15.28] Nobody’s asked me that question before… And I think you noted it earlier - it’s keyed into a lot of what we’ve talked about, like the people you surround yourself with. I’ve got a really great set of friends. Some of them in Seattle, some in other parts of New Zealand, and others around the world. I stay in contact with them and I’m just always learning so much from them… And this might sound silly, but I often find myself thinking “Gosh, I really want to ensure that I’m contributing value back to them, because I’m deriving so much from them.”

Ignoring the things we’ve sort of lightly covered on throughout this talk, and probably pretty important - it’s about what I don’t do. If I was listening to this point, I would probably be thinking “This guy is really focused. He seems to be really driven, and he’s put a lot of effort into reading these things, and understanding, and thinking about it. That sounds bloody tyrant to me. [laughs] That’s a lot of work.” I actually do put a fair bit of focus on “What do I do for my downtime? How do I disconnect?”

I do have an 18-month-old son named Henry, and he’s been wonderful. He’s a great distraction. I try to spend time with him. I’m a very engaged father with him. I allocate a decent amount of time to playing around with computers at home, and I play Starcraft too a lot. Very old game, but I enjoy that… And I do try to block out those times to not be working, to not be on the mission, so that when I’m on the mission…

I’ve never really enjoyed so much when there is a Superman sort of narrative around very successful people. We’ve talked about people like Warren Buffett, right? I’ll be honest, I think the people that are maybe the top 100 financially successful performers in the world, I think they have some sort of mental problem. And I don’t mean that in a derogatory way. I just don’t think that it’s natural, and I don’t think there’s anything wrong with them doing it… But you kind of realize they’re just wired very differently. They’re deriving a lot of life satisfaction from that level of obsession.

I’m obsessed, but I’ll be honest, if I had a billion dollars burning a hole in my backpocket, I’d probably choose some things to do with my time around my son and family, rather than ignore them and just make the next billion dollars. I’d still wanna make the next billion dollars, but I wouldn’t do it at the cost of all of those other things.

Yes, the sacrifice.

Yeah. Sorry, it was a bit of long-winded, waffly answer, but it’s actually more about finding that downtime, and letting yourself think. In fact, I’ll draw you one more story. This actually goes back to the Titan book about Rockefeller. And I have a theory here… Because Rockefeller actually defined effectively the modern management structure of the executive team. Back then there was no telephone lines, there was nothing, and yet he was running a multinational business. We think it would be hard to run a large business now, but you’ve actually got instantaneous global communication networks, you’ve got software that’s telling you what people are doing. You’ve got your finger on the pulse. These were people with chalkboards that were gonna take a week or a month to get a message across an ocean. How the heck did they run these businesses, and run them successfully? It’s a bit of a conundrum.

One part of the book Titan talks about John D. Rockefeller’s day. Now, this was obviously far beyon when he did the first deal with Vanderbilt. He was now a very wealthy man, and had a lot of people in the business. And his day would largely be to come to the office, read through his letters, there’d be a chalkboard in his office to chalk up the price of oil, and whatnot.

[01:04:00.05] He would have lunch with the executive team, he would never sit at the head of the table, and he’d go back to his office and he would lay down on a couch that was in there and have a little bit of a nap, and somebody would come in and read him some stuff while he would lay there with his eyes shut, and then kind of move on.

And you read this stuff, and – I know, again, today you would be like “Yeah, but if you’re really rich, you can get away with it.” You couldn’t get away with it today. I actually think that in a weird way, despite my love of computers, having a device in front of you that screams for your attention and gives you to the millisecond updates on things is really unhealthy. And the reason it’s really unhealthy and why there is such a success differential is because you’re not getting any time to think. And this connects back to why I like running. It’s the thinking time. It’s the time where all you’re left with is you and your brain, to contemplate. And Rockefeller had a heck of a lot of time to contemplate versus a modern executive would have.

And that’s where that value comes from. I will also just say they also had a lot less legislation and stuff back then, and you definitely do not read the Vanderbilt or the Rockefeller book and expect a story on integrity, like The Snowball. But… [laughs] It was just one thing I kept wondering about; I was like “Hm…” You know, we talk about emails, and watching all these metrics and dashboards around the office, and it’s like “I don’t know…” He kind of demonstrated that that’s actually not a key to success. It’s just a thing that makes us feel like we’re being productive, but we’re not thinking.

Being busy, essentially.

Being distracted. Interruptions, distraction… I agree. If we spent more time with our brains intentionally, to contemplate, as you say, I think we’d have – I’d give a challenge to anybody to take that time, to do what you say. Actually plan your downtime. I’m glad you said that, rather than the things that you do; it’s the things you don’t do.

Because I think if you intentionally spend time with yourself, contemplating what your end game might be, what your values are, what your why is - not just the how, as you’d mentioned, because that seems to be pretty easy for those that might be listening to this show, or even be curious about entrepreneurship and running things and being a leader and all those different things. That’s the easier part, is the How, not so much the What or the Why.

And if you spend time with yourself intentionally - I like your idea of running, although I’m not a runner. For me it’s mountain-biking. I get out there and do that, and that’s my time to think, so I can appreciate that. Reserve time in your calendar to think.

Yeah. One thing I think that has helped me immensely was doing things even when other people thought it was weird. When was the last time you took a day of annual leave, and your whole purpose for that day of annual leave was to think about your goals and what you wanted to achieve in life? And you maybe took a pad and you might go and sit in a local park or in the wood, take a walk and do one day. I will guarantee that almost nobody would do that, despite the fact that that would be potentially the best use of your time for the impact on your life - just sit down and write that stuff out.

And I’m not saying that as an insult to anybody. I’m sort of the same. Sometimes I sit there and I go “I wanna diagram something out, but I don’t wanna put the pen to paper until I kind of know roughly what I’m gonna do”, and it’s like “JD, why are you trying to save one sheet of paper, to slow down actually…? Just do the second one with what you learn as you go.” All these things in your mind–


Yeah. “Don’t do this, don’t do this, don’t do this…” And you’re like “Ah, screw it.” Just do it. Go ahead. You can’t go and sit in the woods, writing, every single day. That won’t get you there either. But having a [unintelligible 01:07:43.21] is pretty useful.

I think what your point might be is it’s kind of easy just to blame the phone, I suppose, or the distraction, the machine in front of you, screaming for your attention, to use your words back to you… It’s kind of easy to blame that. In some cases it’s mindset, in some cases it’s habit… But I think we’re getting to this default gear. The default gear is what we do, and we never take that time or appreciate what that time might give us if we slow down enough.

And I think that’s the thing… And that thing, sitting down in the park, writing and contemplating, might be what you do. That variation for me or someone else might be different, but it’s the time to consider. That’s what we often don’t do. We’re so just distracted and interrupted with our busyness. Because I think like “Gosh, if I did that, JD, I’d probably go there and sit there and–” well, I don’t Instagram anymore, I’ve given it up… But I might be “Let me check my email. Does somebody need me somewhere else?” I might be distracted with my potential need somewhere else, rather than my need right then and there.

So too often are we just like in our default gear. We need to shift…

Absolutely. And don’t be afraid of looking weird. Two examples of this… One, the richest guy in New Zealand – and I realized, by the way, that I’ve referred to a lot of things in this podcast around somebody’s wealth… And I don’t actually subscribe to the view that your wealth is your success. It’s just a measure. So I’m not as hung up as I may seem on that. But New Zealand’s richest man is a guy called Graeme Hart. He’s worth about 12 billion dollars, and I think about half of the world’s packing - think Starbucks cups, and stuff - are actually produced by his firms.

Anyway, he’s quite an enigmatic character. He’s not well-known. And that’s another one - everybody think you have to be well-known. This guy’s built a 12-billion dollar fortune and he basically has done–

He’s unknown almost.

…he’s done like one interview in 20 years, as far as I can piece together.

He can go to the grocery store no problem.

Oh, sure. Absolutely. But I was really interested in this, because he was a tow truck driver, and he went to a university in New Zealand and he wrote his MBA thesis on how he was gonna build this organization. I actually wanna go to this university and see if it’s in their library, his work… Because he basically then just went and executed his plan, and he’s built this astronomical organization.

I was kind of obsessed with this guy, and I was clipping every piece of newspaper, and anything I could find, and sticking it to the door of my bedroom when I first moved to Wellington here. And people that come over – because it was a flatting situation, and you had flatmates… And they’d be like “What the heck is this guy up to?” and I was like “Well, this is what matters to me, and I’m not ashamed.” And around the computer, I had all of this stuff about source code to help me be a better programmer. And it was like “You’re a weird guy. People put up pictures of sportsmen, or semi-clad women. That’s what’ normal 20-year-olds do, not this.” And I just didn’t care.

I will admit, early on before I was married, dating women, it was always a bit of an awkward conversation starter if they did come back to my place, because it’s like “Wait, you’ve got all these pictures of this 40-year-old dude on the back of your door?” “Yeah, trust me. Trust me, it’s okay.” [laughs]

But except those oddities, the second one – and this is more of a bit of an oddity that I just wanted to share with the audience, because one thing I used to think a lot about was how to motivate yourself. You have those days where you’re cranking. You’re ready to absolutely just [unintelligible 01:11:22.01] out of the stadium… And then you have other days where you’re just like “Man, where did that feeling go? Why am I so down today?” And I used to think “God, if there was a pill for motivation, I’d take that every day.”

I mentioned The Avengers movie… I’m a big fan of the Iron Man movies, because - unsurprisingly, geek into business loves the idea of a guy that just sort of hacks at stuff at home…

Of course. Tony Stark.

Yeah, exactly. So I actually bought some video editing software years ago now - probably 7-8 years ago - and I went through those movies and I cut out every scene that I found to be like “Yeah, this has got me humming.” And I condensed it down into about a 12-minute clip, and I was like “Okay, this is the closest I’ve got to this pill.” If I wake up in the morning and I’m thinking I’m just not feeling it today, put that on, crank up some music, get myself in the zone… “Right, you’re gonna Tony Stark this day.”

[01:12:19.21] Now, I know the video [unintelligible 01:12:22.02] I can see you smiling; I know everybody I ever tell this to is like “Well, you are a weird cat, JD.” And I’m like “I don’t care. I end up motivated. That’s what I needed.” But I see people who wouldn’t even do that in secret, because it feels weird, and it’s like “Just be weird. We’re all weird. We’re all just pretending we’re not…

I’m a little weird, JD. I didn’t buy editing software to edit Iron Man clips down to a motivational video for me, but…

…that is inspiring. I think what you do though however, is you’ve gotta find your motivation pill. And for you, that was you.

Absolutely. That’s right. I’m sure this video clip would do nothing for anybody else… [laughs]

I like the idea of owning your oddities, your weirdness. I do that. We don’t know each other in the world normally, we haven’t hung out, but there’s some things that I do that are unique, that I only do in seclusion. If I do some of these things that I might do in private time, they’re nothing weird, so to speak, but they’re just peculiar… Not like I don’t think anybody else does. So I appreciate those things about me, and I definitely have taken that advice where I’ve gotta find my motivational pill. It’s not the same thing every single day. Sometimes it’s music, sometimes it’s hanging out with my kids…

I love it when my son says – you know, I’ve gotta go to work, I’ve gotta get some things done, and he says “Dad, can you play with me?” “Yeah. Totally. I’ll give you five minutes. I might not give you the full hour, but I’m totally gonna sit down because you asked me.”

But that five minutes or ten minutes that I sit there and play with him with trucks in the sand, or building some LEGOs for those few minutes - he loves it, I love it, and I walk away with purpose. So that’s my motivational pill sometimes. It might vary throughout life or through the days, but I definitely have to hand it to you - that’s something, to edit that clip, for sure.

[laughs] You get out what you put in.

Since you have your son, I’ll mention this then - for me, it’s my micro-moments. So Covid life, things the way they are now - it’s kind of always been that way for me, because I’ve always worked from home. I’ve always had a home studio. So day to day, generally, because of Covid-19 and Coronavirus hasn’t really dramatically changed my home environment, except from for a while there my kid just didn’t go to pre-school, and we generally just didn’t leave a lot. So that was the one thing that could sort of change.

So I always worked from home, so I always had to battle that sort of “Dad, will you play with me?” versus having to be busy and go to work and do different things and be responsible. So that’s sort of how life was for me… But for me it’s micro-moments. I will walk out and make some tea or some coffee or get a snack, and my family is my break room. So those are my micro-moments. I love that. I’m gonna eat that up - for me, my motivation, my fuel, is those micro-moments. And I’m so thankful for them. I’m truly thankful for them, because I get to spend that five minutes where my kids says “Will you play with me?” and my answer isn’t “No.” That fuels me. My heart’s desire is to say “Yes.” Or mid-interview here with you, this conversation, he might pop in. He hasn’t, but he might… I’d say “Hey, do you wanna say hi to JD?” Maybe not on the camera, whatever… But the point is I won’t say “Get out of here, I’m busy.” “Come on in, say hello.” And then properly leave once it’s time, but I’m not gonna tell him/my kids they can’t come in here. Now, obviously, they don’t have to distract me all day long, but the point is the micro-moments.

[01:16:11.13] You’ve gotta really appreciate what you’ve been given. It might be family, it might be friends… For me it’s kids and my wife and my family; for others it’s different. It’s not always the same shape or the same size. The point is enjoy those micro-moments you’ve been given in life, and appreciate them. That’s my Tony Stark ten-minute clip.

Well, the whole story of Tony Stark becomes one of being a bit more present… And that’s the thing. I suspect that a lot of the listeners, and yourself… I’ve found having a kid was certainly really powerful for bringing me back into the now, and not just being like “What is the next thing?” To kind of quote Tony Stark, if you will, in the first movie he says “There is nothing else. There’s only the next mission.” And then his story arc finished with he has a daughter, and he sort of realized that there’s more to life than just focus on the next mission. And that has been really helpful for me, having him around.

We had a pretty intense lockdown in New Zealand in May; you may not have heard. We’ve now managed to effectively eradicate Covid from the country twice, which is good… So we’re largely living normally, without any international travel… But there was about eight weeks or so where it was heavily locked down. And as I mentioned, there’s a lot of wilderness around where I live, and so just every day… He was going to daycare prior, but I’d strap him to the front pack - he would have been about 13-14 months, so he was not too heavy at that point - and we’d go out for a walk through the forest. And that was my daily thing that I was always looking forward to. It was with him, and it was thinking time, and it was exercise.

Oddly enough, I look back now and I realize, if it wasn’t for the Covid lockdown, I would never be looking back on those memories and being present in those times… Because I would have just kept doing a bit of the work stuff. I do do the stuff at home, I just wouldn’t have had those daily walks for eight weeks, which were really nice.

Yeah. You have to appreciate those things. And it takes intention and slowing down to appreciate those things… Because things move by so fast. Like you’d said, the next mission… Gosh, if that was all life was, you couldn’t appreciate the little nuances that make your life what it is… To even do it in the first place.

That’s right. And you can get a little bit myopic on those things when you are a driven person, and not (what’s the saying?) stop and smell the roses… For sure.

Yeah. Well, JD, I thoroughly enjoyed this conversation. It does have to end… Listeners, thank you so much for tuning in this long. Hopefully you will have gone to the show notes, checked out some of the books that JD and I have talked about… I will do my best to show-note – we do have our show notes on GitHub, so they are open source, and if you can do that, I’d gladly accept the pull request for links that are relevant to what we’ve talked about in the show. If it’s a book, if it’s a quote, if it’s a Bill Gates thing, if it’s a John. D. Rockefeller thing, if it’s a history thing, if it’s your favorite book - drop it in the comments; we love that.

JD, thank you so much for sharing this time and this wisdom with us. I truly appreciate it, thank you.

Thank you for having me. I really appreciate it, too.


Our transcripts are open source on GitHub. Improvements are welcome. 💚

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