Focused - 34: I Think I Just Got Fired, with Marco Arment

Episode Date: November 14, 2017

App developer, podcaster, analyst, and secret entrepreneur Marco Arment joins us to discuss his journey from college to Tumblr, building Instapaper, getting quit-fired, setting out on his own, and working in bursts of productivity.

David Sparks and Jason Snell spent their careers working for the establishment. Then one day, they'd had enough. Now, they are independent workers learning what it takes to succeed in the 21st century. They are free agents. Welcome back to Free Agents, a podcast about being an independent worker in a digital age. I'm Jason Snell, and I'm joined as always by my fellow host, Mr. David Sparks. Hi, David. Hi, Jason. We have a special guest today.

Yes, we do. All our guests are special, really. But this one is somebody that many people who listen to the show may have heard on his other podcasts, or perhaps they're listening to podcasts on software he developed it's marco armand hi marco hi thanks for having me on the show thanks for being here so you are famously somebody who doesn't have a boss so we thought we would talk to you i think that's the idea i mean i i used to have bosses yeah yeah where do you want to start well i guess just for the folks who don't don't know you marco, just to kind of give a little background, you're an app developer and a podcaster.

You have several podcasts. But when I was thinking about you, are you an entrepreneur? I suppose so. I mean, I am in a business that I created myself that pays the bills. And I'm selling an app that I make as that business. And I'm also doing podcasts where I'm selling advertising. And so I guess, I mean, I would never in a million years walk into a party and introduce myself as an entrepreneur because I would feel like a jerk. But, you know, by most people's definitions i suppose i probably am one yeah i was thinking when i wrote i said marco is an entrepreneur that hates the word entrepreneur

it's worse marco because you you made uh instapaper and sold it and you made the magazine and sold it so you could arguably be a serial entrepreneur that's a low blow which is the worst but i i don't think, I think this is not, there are a lot of business podcasts out there where are, that are deeply into that, this kind of idea of entrepreneurship. And then there's a reason that this is free agents is that we, uh, for whatever reason, I think don't think of it that way because we're a lot of times thinking about being on your own and kind of charting your own path and not necessarily building, uh, building a big company. We're talking about just, uh, controlling our own work and, and doing our own thing. And that's something that we definitely seem to have in

common with you because you've talked about on your other podcasts, um, several times about how you think about having an employee or a helper or a partner or something. And it just doesn't seem to be something that you want to do. You definitely are more of a free agent type than anything else. Is that fair to say? Oh, absolutely. I mean, what I have found in my experience so far, and maybe this will change someday, I don't know. But what I've found so far is that i really work best by myself um i am not a good manager of other people i obviously am not very good at being managed by other people um i tried for a long time but it just didn't work didn't work out uh as as well as as as i wanted and as well as they usually wanted um and just i i found that i'm best

off limiting myself to projects and you know scope of things within those projects that i can do myself um with a few minor exceptions of you know easily outsource things like you know i have an accountant doing things but like i don't want to hire anyone else or contract with anyone else to do like features of my app or or even i don't even hire designers for almost anything like i hire almost no one to do almost nothing because i'm just i i work best alone i like working alone i like doing everything myself sometimes to a fault um and and i'm just not a good manager of people but there's another element to you listening to you on your podcast and talking about your products like Overcast,

which is the podcast app that for a lot of people listening to this show, they're probably listening on your app. But you always, in my observation of you, you are always looking for ways to make the things you make independently support you. I think one of the things we struggle with as free agents is how do you monetize and make money? Because if you don't do that, you have to go get a job somewhere. And I feel like you've always been kind of in the forefront

of your industry and app development of looking at new business models and always be willing to explore and find ways to not only set up a free agent style business, but stay in free agent style business and support yourself. Well, and that's, you know, that's kind of a forced lesson I've had to learn over time. You know, I didn't, I wasn't always as experimental, like with Instapaper, you know, my first big app, once I went free agent E, I really didn't experiment much with the business model there. And it really cost the app a lot of market share. And ultimately, I think it cost it its success that, you know, when I sold it, it wasn't out of business or anything, but I was selling it on like the decline,

not on the upswing. You know, I think people might assume I sold it for a lot more than I actually did. Because when you're selling things on a decline, it's, you're not in a great position. You know, that, that was largely, you know, business model wise, it was failing because everything else was free. And so with Overcast, I have been kind of forced, you know, by, by going into an already crowded market to begin with. And, and by, you you know by the increasing competition that's always in this market i have been forced to be much more aggressive with business model stuff

and also i have you know this is a very turbulent industry like whatever is true for this year or two it's probably going to be different next year or two. And everything is so turbulent and so hyper competitive in the app business that if you aren't willing to experiment with things, you're not going to do very well. All right. So let's talk a little bit about how you got to be a free agent. I mean, did you, when you were in college or young, were you always someone looking to get out on your own? Was this something you planned? Not at all. I, you know, I came from a family that was fairly traditional. You know, we, you know, you go to college, if you can, you go to college, and then you get a good job,

and you work that good job until you retire. And that's it. Like, that was the plan. And that was all I knew of the world the idea of like starting a business sounded like this crazy thing that like well only you know business people do that i'm not one of those people who starts businesses um that that whole thing was was a foreign concept i was intimidated by the idea so much so that i never even really considered doing it. So I followed the path I thought I was supposed to follow, where I went to college, barely. Like, I barely graduated. My grades were terrible because I'm a terrible student. I actually graduated late. I failed a required class last semester and had to do, you know, like the ceremonial walk at graduation without

actually getting a diploma and then do it by mail a few months later. I mean, I was a mess of a student. And then I went out and got the first job that would hire me. And it was a good job in Pittsburgh with a software company there. Worked there for a couple years, then moved to New York for basically relationship reasons that, you know, my then girlfriend, now wife, was only basically getting jobs in New York for her field. So, we came to New York together and started our life here. And, you know, in order to move to New York, I had to get a job in New York. Of course, the idea of coming to New York with no job was completely, you know, unconsiderable to me that's a word now i guess

and so i went on went on craigslist and found jobs and took this job with this weird guy named david who was seemed suspiciously young who wanted us to make php web apps for people and so i went to go work for him and a months later, the next app he wanted to make between consulting clients was this idea he had called Tumblr. And we started building that. And eventually that took off and replaced the consulting business completely. And then I was the programmer at Tumblr. And for a while, it was just me and David.

And then eventually we hired some more people to help out. And it became so big so quickly that it kind of took over our lives very quickly. And I found myself kind of thrown into this massive, like, high-volume, high-attention web scaling world trying to keep up with this crazy site called Tumblr that was growing like crazy um and i had no idea what i was doing you know we were david and i both were pretty much learning as we went um it was it was a solid four and a half years or so of lots of stress but also lots of learning new things and forcing ourselves to be in this crazy situation and get through it. And it was a crazy ride, you know, like the, the way that, you know, I never worked at Apple, um, but I've heard stories of people who have worked there under some of the crazy Steve jobs eras, like the lead up to the original Macintosh or the lead to the original iPhone, um, or the iPod even. And the stories

that people tell often have a similar theme which is like man that was like the the hardest i've ever worked in my life i learned the most i've ever learned in my life but i'll never do it again that's basically the theme of those stories and that's how i look back at my time at tumblr um it was a crazy ride and it was invaluable with you know professional development and and intellectual development and everything else but man was it crazy and i was i was really starting after you know after four years there i was really starting to burn out pretty badly uh and the company at the time was in a terrible position to have their lead engineer be burning out. You know, they were still needing to scale like crazy and they were about to have to

take a major step in scaling, which is basically switching from dedicated servers to co-location. Like they were going to take this massive new step, re-architect a lot of the server stuff like that, that was necessary to keep up, hire a bunch of additional programmers and sysadmins and database admins and everything. So like hire a big staff, change everything about theadmins and database admins and everything so like hire a big staff change everything about the way things were hosted like that was that was

the next logical step that they had to take and i was not at all either qualified or up to that job at the same time i have been building this thing on the side, this app called Instapaper. And I couldn't do iOS development at Tumblr. We had an iOS app, but it was just this contractive thing because I didn't have time during the day to do the iOS app. I had to be running the servers and programming backend stuff.

You're trying to keep the trains running. Exactly. And because David and I, we didn't know what we were doing. And so we should have hired more programmers earlier uh but because we we waited on that we thought we can handle it if we don't have time to hire anybody right now we're too busy and because of that we waited way too long and so the like we had like no time to for me to be playing with ios apps but i really wanted to so i was doing on the side in the

evenings and weekends i was doing instapaper and that was taking off and it was actually financially doing so well that i could have quit my job at tumblr to go to instapaper probably six months before i actually did and i kind of wanted to but i didn't want to leave tumblr stranded and i was also really really scared to go out on my own because i had never been self-employed before i had always worked for someone else and the idea of well you know it's doing well this month but what about next month and what about after that like and i was i was trying to buy a house and trying to like you know start a family i'm like this is gonna be this is a terrible time for me to like lose certainty. I have this good job. Let me just

keep plowing through at it. Even though I was burning out quickly, I no longer needed the money because this paper was doing well enough at that moment, at least. And it was about to take this massive turn into an area that I was not at all qualified to lead. Fortunately, an area that I was not at all qualified to lead. Fortunately, David Karp is smarter than me. And he basically quit fired me. He it's, I got quit fired. I, you know, he, he basically took me to, to, you know, a bar on the corner from the office one evening. And he said, look, this is, you know, I see the problems here. we need someone else in your position to do what we have to do next and i know you don't want to work for someone else so you know basically i think it's time for you to go and you know and those weren't his exact words but in the friendliest way possible

he quit fired me and you know and i'm like wait a minute like i walked home i like so so you know tiff my wife came to meet me at the office because she worked nearby and so we would walk back to the train together and on the walk home i'm like i think i just got fired but i think this is everything i want because what he was going to do he he he was allowing me to leave guilt-free on not not my own terms but well on my own terms basically but just i didn't choose the timing and he was forcing me to go do instapaper full-time which is what i had wanted to do anyway for months before that i just didn't think i could get out of tumblr and he then gave

me an exit and i i got all my stock i i was on like the air and their insurance until i was ready to get off of it like everything was as smooth as possible and he basically like escorted me into the freelance life which i had been dying to do anyway and so it was probably the best thing that ever happened to me and i became independent it's interesting to think about his thought process there because obviously his thought process was he needed somebody to like a cto or you know somebody that he felt like was not what you were going to want to do or be able to do and and the next step was logically then that you would report to that person and you're like oh that's not going to work you know yeah and he knew that too and he knew it right so he knew it's like what what did he know

that you were doing instapaper on the side and and all that oh yeah he was he was fully and he was very supportive of it because you know he he knew that you know i was the kind of person who liked doing side projects and he could tell that i was really enjoying getting more into the apple community as opposed to just like the web development community and and he was into in the apple community also but not to the degree that I was. And he could tell that that was really where my passion was going. But that, you know, so he, I mean,

he's pretty good at, you know, reading people in that way. And he knows what people want to work on. And so, you know, he could tell that not only did I have something on the side, which he knew about, you know, full, you know, I didn't keep it from him. So like, not only did he know something on the side, which he knew about, you know, full, you know, I didn't keep it from him. So like,

not only did he know I had a safety net, but he also knew that I would rather jump into the safety net to keep working for him. And so he basically gave me those graceful legs at possible. Yeah. You were lucky there. Cause I, we hear from a lot of free agents and I think myself and maybe Jason to a

certain degree included was, uh, at the jobby job, we did not want everybody to know about all our side stuff. And it would not have been, it would have been frowned upon, frankly, if we had let people know what we were doing. Oh, yeah.

Well, I mean, honestly, I don't know how I would have kept it from him. Even if I tried to keep it from him, that wouldn't have lasted very long because the app was actually doing pretty well at that point. But I was very lucky to have that kind of situation where he knew where he was he knew about it and he was okay with it and actually supportive of it like he even sent me to wwdc a couple times on tumblr's dime even though

he knew i was really there for instapaper um because you know he he sent his web developer to the apple developer conference and i i never i never even saw the source code to the ios app i never did any work on tumblr's ios app um so it's like i you know he he was very supportive uh but you know he you know he and i went back a few years at that point and and you know he wanted to do right by me and and so it really worked out well and had he had i not been forced to go indie at that time this was in late 2010 i'm not sure how long it would have taken me to try like i i probably would have like you know if i wanted to leave tumblr probably would just try to get another job somewhere or something like the idea of going indie had just

never occurred to me to really do like to really commit to and i was i was afraid because i had never done it and the uncertainty really was very frightening. It can often take a push that that's definitely what happened with me that I, uh, you know, I, I went through the sequence of layoffs and finally told people like, look, I can't, I can't do this anymore. But it was, it was very much like those external actions were the things that pushed me out because I could have gone years earlier and never did. Right. Because it's like, well, you know, cause you, something you mentioned that I actually, if I can get back into sort of your, what you were thinking before you had that conversation with David, you said, uh, Instapaper is doing well enough that I could, that I could

go out on my own. When I talk to people about this, the challenge is you look at your income from your job and your side project and you're like, well, yeah, I could live on the income from the side project, but it's awfully nice to have two of them, right? How did you do that calculation of I could live on Instapaper? Oh, I mean, it was, you know, first of all, it was basically like a dumb month to month comparison so it's like well this month and last month it did well enough that it surpassed my income from tumblr for those two months but like you know the month before that it didn't right so it was it was a big question mark there and and for the and my immediate plan at that time was well why throw away the second income like yeah if i i am doing

both right now if i can just keep doing both why throw away all that income because you know like i i don't come from money i come from a very lower middle class modest family background and so the idea of just passing on good money was crazy sounding. Like I would, that, like, that does not exist in my mind at that time. Like I would never have done that. And so the idea was like, well, why should I quit this job? That is totally fine. Uh, that it's a good job. Why, why leave it? Cause when I don't have to. Yeah, I do think that your background plays a big role in this. I mean, you talked earlier about, you know, in your family, you got a job and you work the job. So you got the gold watch. And that was that. And, and I'm sure that

really sets your mind because, because I'm the same way. I talked about this in the past. I had depressionary parents and they pushed me very hard to get a good job and to keep it. And I didn't get pushed out. It took me 22 years to voluntarily jump. 22 years, you know? So, you know, I do think, I mean, looking back at, you know, your family situation, like where your parents, I guess it wasn't really encouraged for you to go out and just go out on your own growing up. because you know like like even when i took the job at tumblr you know with which at the time was taking a job with this crazy young guy named david in in the city my mother was trying very hard to convince me to take the offer i had from bloomberg instead i had two offers to come to new york the other one was at bloomberg

um and and the bloomberg job would have really been a terrible fit for me and i could tell that even from the interview um but it was a big established company and it was like it seemed way more stable and yeah my mother was very concerned like wait you're gonna go work for some guy instead of this nice big company with this offer they have a building why yeah exactly a big building too yeah my parents would have had the same conversation with me i totally understand and honestly and had had bloomberg not been such a an abrasively awful fit for me like i mean really we it was a terrible interview i should never work there uh but you know had that interview gone

even slightly better i would have taken that job anyway because i was thinking the exact same thing i was thinking like you know moving to new york is incredibly intimidating because everything here is so expensive like i if you know just by making the move here just by like getting a security deposit for an apartment and everything like i depleted my savings of having worked two years in pittsburgh just to move here so it's like i'm gonna start over and if you go a month or two without a job in new york that's a pretty big hit to your finances when you're like 25 so that was it was a huge risk and really the only reason that i that I took the job with David at all he was he was in a shared office and it was shared with um a cartoon producer uh and and so the the whole thing was like decorated

with like bright colors and like preschool children's characters on the walls and everything i'm like what is this place are you the boss like what what is going on here like it was very very strange um but yeah it worked out pretty well in the end this episode of free agents is brought to you by squarespace enter offer code free agents check out to get 10 off your first purchase make your next move with squarespace which lets you create a website for your next idea you can get a unique domain award-winning templates and more so if you want to make something that exists on the web, you can go from nothing to a full site,

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make your next website. So despite having your parents or despite the inclination to want to keep a job, at what point did the seed get planted to say, you know, I could go on my own? It was really only when Instapaper started making real money. That was like, even when I was doing Instapaper and it was getting a lot of users, the idea taking it full-time seemed crazy and totally you know not even under consideration because you know i i had tried side projects on the web before and they you know they they never amounted to much um you know and i even i had like ads on my blog and stuff but those didn't amount to much either and so it was always like at best some decent side money every month coming in um but it wasn't until newspaper started

making like a full-time salary worth of income every every month and it's pretty good one too that's when i started realizing oh my god this is real but that was also you know this was late 2010 where i where i went to indie here in early 2010 was when the ipad launched the very first ipad and instapaper sales went through the roof during that time but i also realized like this could just be temporary because what if the ipad is a flop you know what if it's a fad or what if like i just saturate the market really fast and everyone who wants instapaper on the ipad is buying it now and that's why my sales are so good right now but then are they still going to be good in a year or in two years like will i just saturate the market and then this income maybe won't be enough to go full to have gone full time

anymore um so you know i had all these questions about about the reliability of that income which i think were warranted like looking back on it it was a crazy roller coaster and it wasn't that reliable uh but ultimately i didn't even consider making the move until it was making so much money that there was actually some buffer there that like even if it made you know 30 less next month or 50 less next month i wouldn't be underwater so take us through what happened when when you went out on your own with instapaper like obviously you're in the app store, you're relying on, this is the days of no, uh, no in-app purchases, right? No subscriptions are happening.

You're really relying on new people finding Instapaper and buying the app. Yeah. I mean, that was the business model for the entire time I owned it. Really. I did eventually add a one dollar a month voluntary subscription um to just to get basically nothing uh i think i think i i think i gave you search archives or something like that because search was expensive and i couldn't index everyone's articles um but that was a feature almost nobody used um you were mainly paying because you liked me basically like

that was that was the reality of that um but like that was like for the most part it was entirely dependent on just well when you want the app you pay you know first for the first year or 10 bucks and then after that it was five bucks you pay five bucks for the app eventually i think i lowered it to four it doesn't really matter um but yeah first you know upfront payment and that was it and that had a lot of benefits and a lot of downsides and i would imagine your your revenue was choppy. I mean, you sort of mentioned it. Like, did you go on your own and then the money was solid for a while and you felt good?

Or did you go out and then start to see variance and immediately start being, you know, concerned about how the money you're making was not stable? It did really well for a few years. Like, it had a really nice run um and it it wasn't immediately obvious that it was going to crash uh but certainly like you know like i 2010 was like the ipad year i think 2011 was the that was its best year total during the time i had it and maybe during all time it just slowly started declining after that and that was that was probably from a number of factors um one of one of the big ones obviously was that i had pretty major competitors all of which were free

and then apple made reading list and that was built into the os for free and so like it was it it's a very hard sell in the app store if your app is four or five bucks up front uh and then there's another app next to it that's free that purports to do the same thing uh you're gonna have really hard time selling that app it's not impossible you'll sell some uh but like the the ratio is awful for like how many people will just go to the free one instead um so that's and then eventually you know with paid up front you saturate a certain you know certain parts of the market and then you don't make money from those people anymore and so you might have someone who really

loves the app and uses it every day who paid you five dollars four years ago um but you're not making anything else from them anymore and that's kind of a problem you know it it's okay when the market is continuing to grow as the iphone you know did for a long long long time and the ipad did for a little bit shorter of a time but we had still you know still had a few good years of growth there but then once the growth like once fewer people are getting their first iphones and their first ipads that pay up front model starts to slow down pretty dramatically. And so presumably your revenue starts to go down and you start to think to yourself, what am I? At some point, are you motivated by looking at revenue going down or thinking that the revenue is inevitably going to go down and thinking what am i going to do next is that a motivator when you're making decisions about what projects you're going to work on or are you do you have a like a list of projects that you'd

like to work on and uh and they just sort of present themselves how do you decide i'm going to do a podcast app and i'm going to stop focusing on insta paper well for me it's all about like looking at the direction things are going and and i have not always been good at this and i'm going to stop focusing on instapaper well for me it's all about like looking at the direction things are going and and i have not always been good at this and i'm still not very good at it but i i've been slowly improving my my ability to see this and react to it over time um but you know with instapaper i started seeing it go down and i tried some things to boost it back up and they just weren't working it was just it just kept going down and the in absolute values it was still making decent money every month but once you see a downward trend that doesn't seem to be reversing itself you should be concerned

even if the absolute numbers are still very good because you know those kind of like long-term trends it takes a while usually to turn them and you might never be able to turn them. So like if you're seeing a consistent downward trend, uh, for me at least that that's time to start looking at, you know, something that can replace this, um, or, you know, or looking for a way out basically. Um, and so for Instapaper, I didn't really have anything i was dying to do immediately i i briefly did the magazine uh which was not successful it was it was a fun project i'm

glad i tried i learned a lot doing it uh but it was you know financially in the app store it was it was pretty much a complete bomb. And again, don't assume I made a lot on that sale either, because when you're selling an app that you consider fairly worthless, it turns out it's hard to sell it for much of anything, because everyone else is looking at the same numbers and trends and stuff that you are when you decide to sell it, because it's plummeting to the ground. So that was fine. And I sold it to Glenn, and Glenn plummeting to the ground um so that was fine

and i i sold it to glenn and he he you know glenn fleishman was the editor at the time that i had hired um and he he did his best to try to save it and and even he couldn't keep it alive and he had way more experience than i did with magazine stuff so if anyone could have done it it was him and even he couldn't do it so i don't i don't blame him at all but anyway so you know i had i had done this kind of audio demo thing because i've always loved dealing with audio uh always and i i had done this little audio processing demo app like just like over over a couple of nights you know a few months before i sold instapaper and so the magazine was kind of crashing instapaper was being sold and i realized you know let me go back to the audio demo i did because i had prototyped what was smart speed and

voice boost basically um and i i had this idea for a while of you know real-time audio processing on you know for a podcast player and i just assumed that the iphone hardware just couldn't handle it yet or it would it would either be too slow or you could do it but it would burn the battery too much and so i just assumed like this really can't be a thing yet uh fortunately i was wrong um you know when i when i made this prototype i realized that it was actually totally doable and and without even like too much craziness like without even too much effort of trying to optimize it it was totally fine and and without even like too much craziness like without even too much effort of trying to optimize it it was totally fine and i could indeed run these effects in real

time on at the time i think even an iphone 4 or 4s and it was it took like no time at all to do and so i i had the idea like you know i would like to build a podcast app, but I don't really, like, I wasn't sure if I had the skill or the time to build an entire podcast app, because they take a lot of work. There's, like, podcast apps have a lot of different screens, a lot of different edge cases, like, a lot. They're surprisingly complex apps. And there's usually a back end to them as well so there's other pieces yeah and well and at the back end i wasn't so you know like running servers and stuff like i because i had the experience at tumblr i was pretty good at that and and i knew that i knew what it would take not necessarily that that it would that it would be like you know totally free you know time or money wise but i at

least had a really good idea of what it would take. And running a podcast app servers is way lower needs than running something like Tumblr. And so to me that like the idea of running service for that was kind of like a vacation compared to where I had come from with Tumblr and even with Instapaper too, like it's paper was getting pretty complex and pretty expensive at that point. and i and i again i knew like podcast apps needs would be much lower than even instapaper let alone tumblr so but the main reason i didn't want to do it is you know a instapaper was still fine i hadn't yet realized i should probably sell it so it was still fine um and then b i didn't have time because i was running instapaper in the magazine and then c i i had assumed that the market for a podcast app, because in 2010, podcasts

were very much a thing. But, sorry, this is past 2010. This is probably 2013 or so. Podcasts were very much a thing and they were growing, but it was still a pretty specialized market. It was still very far under the radar uh you know it was it was really it was it was a niche or a niche i don't know how to pronounce that anyway so uh then tumblr sold to yahoo and so i got some money out of that and i realized i

now had a cushion and at around the same, the magazine had already failed or was failing. And Instapaper was becoming unwieldy to manage. And also everything was going down. So I sold both of those things. And I had nothing to work on. And that's when I decided, let me make the podcast app. Because now I have the time.

I have nothing else to do. And I want to do something. and since tumblr had sold i i had a cushion of basically safety money so that if i invested like a year into building a podcast app and then it turned out that it was terrible and that there was no market for it i wouldn't be financially destroyed i wouldn't have like my savings wiped out or anything else um you know i still had to do something but i had you know i had i had some buffer um and so that's what when i decided you know what let me just make what i want to make right now and see if it works and that was overcast so a little bit of a combination of seeing where things are going and having an idea and and uh and circumstance sort of led you to go

from doing instant paper to doing Overcast. Yeah. This episode of Free Agents is brought to you by FreshBooks. Go to freshbooks.com slash free agents and enter free agents in the how did you hear about us section to get a 30 day free trial. As Jason and I have spoken about on the show, you need to get paid if you're going to be a free agent. If not, you're just got a hobby. The good news is that's a lot easier now than it used to be, and you can do that with FreshBooks. FreshBooks offers cloud accounting software custom-made for freelancers and free agents.

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There's no credit card required. All you have to do is go to freshbooks.com slash free agents and enter free agents with a space in the how did you hear about us section. If you're going to pull off this free agency thing, you've got to have getting paid down and FreshBooks is there to help you. We thank FreshBooks for all of their support of free agents. I think we should talk a little bit about what life is like for you in terms of getting your, getting your job done, what works for you in working on your own and what, um, maybe you struggle with, you know, do you have a, what's it, what's an average work day for you? Like, do you have a set schedule? Do you have things you do at certain times? You know, you, you, I go into the office at this time and I work

for this time. How does, how does you, How do you structure this life of you on your own developing Overcast? So when I worked at a regular job for other people, I always had this problem where my productivity would come in these crazy bursts about maybe once or twice a week. And so I'd have like, you know, one or two, two you know multi-hour bursts of productivity a week and the whole rest of the time i would basically be you know wasting time like browsing the internet or doing kind of mindless tasks that didn't really need to be done or that i or that maybe i could have done differently or could have automated or something like that and that is still exactly how i work today like i still don't have a consistent productivity window where it's like i don't just arrive in the office at nine in the morning and have you know four

hours of productivity and then take and then eat lunch and then have three more and then turn my brain off for the rest of the day like that that is never how i have worked and it's not how i work now in many ways i envy people who can do that i wish i could do that but but that's just not how i work um so the way i work is basically really inconsistent and erratic and impossible to schedule or manage so i might go two weeks without touching code or i might have like three days of just massive productivity where i am just plowing through things and making a really really great update or solving some really hard problem um and it's just it's totally all over the map and this applies to both like the macro level of like how

many days a week am i productive as well as just like the periods during the day like you know the hours in the day in which i'm productive vary all over the map like sometimes it's the morning sometimes it's the evenings it's like it's all over the place do you have any way of knowing when you're going to get into one of those zones i mean can you like force it or does it just kind of happen i i wish i knew but i don't i i can be fairly sure when I'm not going to be in one of those zones. So if we're cleaning up after dinner and my wife and I are trying to clean up after dinner, put our child to bed, and then we're trying to decide, do we watch TV together or am I going to go in the office and work? I can always tell at that point, can my brain handle work right now or not? Like, am I in a working state of mind or not?

And it's very clear to me whether I'm not. And so then I can just like, all right, we're going to watch TV tonight and I'll work tomorrow. But other than that, I really, it's, I wish I had more control over it. This is, I mean, you know, you said like what works and what doesn't. We're bleeding this into each other because ultimately what I find the most challenging about working for myself is trying to have any kind of regularity in my schedule. And just that, you know, the general topic of time management. I'm terrible at it. I always have been from the moment i i went indie uh to the present day i'm terrible

at time management scheduling consistency of the time uh i do get the work done like i i do what i need to do but it's a pretty wild question about when that's going to happen but you're not it doesn't sound like are you like a deadline guy you know some people flourish once you know they're 48 hours from deadline that that's not really even a consideration is it well i do have deadlines that are that are you know externally imposed usually so for instance like whenever apple releases new hardware like i have to make sure my app works on that hardware you know on day one if possible uh so like stuff like or like new versions of ios come out or like apple releases a beta that breaks everything of mine like stuff like that i i have to deal with that so usually it's like the apple product cycle externally imposes deadlines upon me which i do respond generally

pretty well too but other than that there aren't really any the other thing is for the other half of what i do really which is podcasting uh that works totally differently like that like everything i've said so far has been about programming uh podcasting i do it with other people on a schedule and the deadline is this has to be out this week or this month so podcasting i do totally differently because it's a totally different kind of work and because i'm kind of forced to but programming is all over the map for me that's i it's a totally different kind of work and because I'm kind of forced to. But programming is all over the map for me. It's funny. I feel some similarities there where, yeah, for a lot of the same reasons,

podcasting tends to be much more regimented because you are dealing with other people and it cannot be asynchronous. It is asynchronous. You're talking to other human beings at a set time. And then everybody wants you know your podcast comes out the next day or two days later or whenever and so you got to do that and then for me like my writing it's similar it's like i've got some deadlines and all but whether i write that story on tuesday afternoon or wednesday morning or whatever it's sort of like

i can write at any time and so it's a little bit so i've got some squishy stuff and then some rigid um more rigid structure which is not bad i i you know it's i mean it it's got to be nice in a way to know that every wednesday night you're going to record atp and you know that that's on your schedule and that and then you're going to presumably edit it thursday something like that yeah and yeah so like the podcast schedule it really imposes a lot of welcome structure to to my week because normally there wouldn't be much also it helps a lot is once our kid got old enough now he's in school and so now we are all you know subject to the school schedule basically so right you know if i want to get a lot of work done during the day it's best to do it during the school day um Um, and so that, and, and when, when certain weekdays have no school for some reason, whether it's holidays or other,

you know, school events, um, then I, I feel that I, and I have to plan for that. I do. All right, well, is, is today going to be a family day? Are we going to be traveling? Cause it's like a three day weekend or whatever else like that all, that all plays into my schedule, you know, externally. Um, but for the most part, I'm still, that all plays into my schedule, you know, externally. Um, but for the most part, I'm still kind of all over the place. Well, one of the advantages I think of your independence is that you, you basically work for yourself. I mean, you, in the true word, sense of the word, like you don't have 15 clients that you have to juggle their priorities. It's, it's your app that you're working on. It's your podcasts.

And I think that structure, if you can do it really makes the, you know, the burst work that you're describing, uh, makes it a viable option. Yeah, exactly. I mean, it's, and part of that is just like the nature of what I do, like the nature of apps. Like, you know, if, if again, if you're a podcaster or if you're a writer for for magazines with deadlines or you know like like there there are lots of you know lots of other businesses where i don't know where i wouldn't have this kind of freedom but yeah it is it is pretty nice to have this you know to have my own products in that way you know the other the downside of that though is like because nothing is forcing me to release on a certain schedule or to or to build fusion a certain schedule

it's very easy to either slack off for a while and to then not update the app frequently enough or hard enough or whatever or to invest time in things that delay it that i probably shouldn't spend that time in um so like like to invest in like basically a big time sink feature or or a big time sink effort you know whether it's modernizing this part of the code or you know doing this this big complicated feature that maybe isn't worth this amount of time that stuff becomes a much more common pitfall. So let's look at the, this is sort of my last question, which is looking at the future a little bit. Can you conceive of doing anything else or are you ruined for other things now in terms of your work? I mean, I understand that the world is going to change and who knows what we'll have in podcasts. Wasn't a thing, now it is

a thing. Maybe it won't be a thing again in the future who knows but in terms of just your work style if you can manage it um is is you know is this it for for the foreseeable future for you is this the the how you want it to be oh definitely i have no plans to change that i mean i might change the things i work on although i honestly have no immediate plans to change that either. But, you know, I might change the types of work that I do or the specific projects I do, but I intend to work for myself for the foreseeable future or basically as long as as long as it's possible or as long as as long as that's what I keep wanting. You know, whenever I've thought about any other option, I mean, you know, I've had I've had a couple people here and there like, you know, want me to come work for them or I've thought about going to work for someone else. commute into the city probably, or just having to deal with that, all the additional overhead and inflexibility that that would bring to my life. Meanwhile, right now I'm here and when my

son comes off the bus at three o'clock in the afternoon, I'm here and he can walk around to my office and show me the cool thing he made in kindergarten today. And I'm here for that. into my office and show me the cool thing he made in kindergarten today and i'm here for that and if we need to like you know go do to go run an errand in the middle of the day i can do that too um i just started getting allergy shots again it's like this long-term thing has been on my list forever uh to finally try to fix my my horrible seasonal allergies so two days a week i'm now going to go to a doctor's office and have to sit there for an hour in the middle of the work day like i i have the freedom to do that now because i don't have to clear with my boss that oh by the way can i have like two afternoons off every week for the foreseeable future like that you know good luck with that right um all these things that when i

was employed were a huge pain to try to like work around or to try to get permission to go run these errands. And I never had a full-time job at the same time that I had a kid. But I really feel for people who do that because trying to share family time with children, especially with a full-time job like you just get so much less time with them than if you're home even if you you know close the door to the office all day and don't let anybody in or are on a different floor of the house or whatever else like that you still then don't have a commute or things like that like it's and you can still like take a day off if you need to um there are downsides to that you know like when i take a day off no one's covering for me just work isn't getting done like it's not like nothing keeps going without me like it just

doesn't happen until i get back so no progress is made i can't really leave for too long or stop working for too long uh but i'll take this trade off like as long as i can do this as long as this is still a viable business for me to do i plan to keep doing this and anything that would involve changing my lifestyle whether it's going to work for someone else or even like you know taking on investment and making this a big company and hiring people which would then make me still have to go into an office every day still still have bosses, the board, the investors. I don't want that. I don't want that at all.

I really just like the way things are, and I intend to keep doing this as long as I can. Well, sounds like you're pulling it off. Thanks. Yeah, so far. Well, Marco, thank you so much for spending time on Free Agents with us. Thank you so much for having me. This was a lot of fun. And to everyone out there, of course, we are looking for for your feedback our next show will be one of our new regular shows

where we talk and we also answer your questions and read your comments you can do that by emailing us hit up the contact us link at relay.fm free agents or take advantage of those new longer tweets to send us your comments at free agentsentsfm on Twitter. And of course, we'll be back in a fortnight to talk about whatever issues David and I are grappling with. But until then, David, it's been a pleasure. As always, Mr. Snell. Bye, everybody. Bye. Thank you.