Developing Perspective

#208: Sam Soffes.


00:00:00   Hello and welcome to Developing Perspective, developing perspective is a podcast discussing

00:00:04   news of note and iOS development, Apple and the like.

00:00:07   I'm your host, David Smith.

00:00:08   And typically Developing Perspective is never longer than 15 minutes.

00:00:11   But this is a special episode where I'm bringing back something that I did a little while ago

00:00:16   where I do kind of an interview series where I get on a call with a few interesting developers,

00:00:22   designers, people like that who are making things that I admire and look up to and talk

00:00:27   to them for a little bit about what it is they do and how it is they do it.

00:00:31   And today I'm delighted to be joined by Sam Sophis, who is a designer developer of many

00:00:37   things that we'll dive into and talk to in a minute.

00:00:40   But before I get into that, hello, Sam, welcome to the show.

00:00:43   Hey, thanks so much for having me.

00:00:47   It's great to have you.

00:00:48   The ostensibly the reason I said I was going to bring you on and I thought would be interesting

00:00:52   to talk about is, so you're a designer developer of you have your own products, as well as

00:00:57   as consulting products.

00:00:58   And you have been doing this, as far as I can tell,

00:01:00   for about as long as you can.

00:01:03   I have been doing this.

00:01:04   I think you're, like me, were a designer of--

00:01:09   you made apps for essentially day one,

00:01:10   if I'm remembering right, of the app store.

00:01:13   And a little Mac before that, too, which was unique, I think.

00:01:17   Yeah.

00:01:18   Well, there are fewer and fewer people

00:01:21   for who were doing Mac apps back then,

00:01:24   and then who were doing apps at the beginning.

00:01:25   And it seems crazy now, whatever it is, six years later,

00:01:28   to think about even what we were doing back then.

00:01:33   But before I dive into that too much, I was just

00:01:35   wondering if you could give a quick overview of your history

00:01:39   as a developer on iOS and what you do now.

00:01:43   Sure, so I guess I'll just list some notable things

00:01:47   I've worked on.

00:01:49   My first app was called Bible.

00:01:51   It's like a lot of folks use it.

00:01:55   Not so much to my contribution, it just kind of, you know, sells itself, I think.

00:02:00   But then I worked at Hipstamatic for a bit, was the lead there for a little while and

00:02:05   I worked in this app called Cheddar for a while.

00:02:07   That was a to-do list, like service and sold that.

00:02:13   What else?

00:02:15   More recently I guess shares, it's an app for like tracking stocks and then I made a

00:02:19   a blogging platform called Rune that I recently sold and I think that's it. I don't know.

00:02:26   Lots of stuff over the years but I think those are the highlights.

00:02:29   Yeah, I feel a little bit of a common bond with you in so far as when someone asks me

00:02:37   what I do, like, "Oh, I make apps." And it's like, "Oh, what do you make?" And I think

00:02:43   for a lot of people, they're expecting me to have like one thing, like, "Oh, I make

00:02:47   this app.

00:02:48   But I always struggle with, well, how long do you have?

00:02:50   I've got-- I think it's probably developed dozens and dozens

00:02:55   of apps over the years.

00:02:56   And it's kind of nice when you have a list.

00:02:58   It's like, I think I was working out the things that I think

00:03:00   of you as.

00:03:01   And it's things like whiskey shares, coins,

00:03:03   rahoon cheddar, your Bible app from before, Hipstamatic,

00:03:07   and then some of the consulting projects

00:03:09   that I know you've worked on, so tiny and lightly.

00:03:11   And it just sort of goes on and on.

00:03:13   And it's kind of a crazy thing.

00:03:16   How do you think of yourself as when you do this?

00:03:21   Are you identify yourself with the products that you've made or with the system of the

00:03:27   consulting you've worked or the things you've done as an employee?

00:03:29   Where do you identify yourself as now when you're trying to describe yourself?

00:03:34   Interesting.

00:03:35   Yeah, so when I meet people at a party or whatever, someone's like, "Oh, what do you

00:03:41   do?"

00:03:42   I'm just like, "Yeah, I'm an iOS contractor."

00:03:44   Like, you know, what do you work on?

00:03:46   Usually I'll just like save my most recent project because that's what I've been working

00:03:50   on and kind of leave it at that.

00:03:51   I don't usually get into the whole list because I feel like that's boring and slightly arrogant.

00:03:57   I don't know.

00:03:58   But yeah, I mean I think of what I do like I guess to myself as far as like my goal is

00:04:04   to make products that can be sustainable so I can live off them.

00:04:10   Like what you do is like the dream situation.

00:04:14   But financially, it hasn't worked out for me.

00:04:16   So I do consulting to kind of fill in the gaps.

00:04:18   But my focus is my own products, not growing a consulting business.

00:04:25   So the consulting is a means to an end in that way.

00:04:30   But how do you balance that though?

00:04:34   So back in the day, I used to do more consulting and it was always incredibly hard to…

00:04:40   to find the balance between the two.

00:04:43   Where consulting is kind of this one-to-one, very direct.

00:04:48   You do something and it has a very clear outcome.

00:04:52   You have a contract, you spend this hour,

00:04:54   you'll get paid this amount of money for it.

00:04:56   And then with product, it's often

00:04:58   a lot more interesting work.

00:04:59   It's often a lot more engaging or something that I enjoyed.

00:05:02   But it's kind of ephemeral for whether and when it

00:05:06   would actually have a return.

00:05:09   I'm curious how you find yourself balancing that because it seems like you've been doing

00:05:12   this for long enough that you've probably kind of worked something out for that.

00:05:16   Yeah, I mean I definitely have like my secret recipe of running a good client and we can

00:05:23   go into that if you're interested.

00:05:25   Okay.

00:05:26   So, yeah, I only do – so basically I have a bunch of rules for myself and as long as

00:05:32   I don't break them, I found that I'm pretty happy doing what I'm doing because overall

00:05:38   I don't like consulting just in general but paying my rent and feeding myself is kind

00:05:45   of nice.

00:05:46   So I do end up doing it but I feel like under these constraints, it's actually slightly

00:05:53   enjoyable.

00:05:54   Slightly is probably being too harsh.

00:05:56   I do enjoy a lot of my projects I work on.

00:05:58   I guess kind of the first thing is I only do one at a time.

00:06:02   I never like overlap.

00:06:03   I've done it a couple of times on accident now and it's been terrible, like ridiculously

00:06:07   stressful and I always feel like I'm cheating on the other one or something.

00:06:13   So one at a time and then my hourly rate is pretty high and I think that's really important

00:06:21   because when I'm doing something I hate or the client is making me do something stupid,

00:06:28   I'm not like "I just want to quit and give them back their money and go do something

00:06:31   else because I'm just so angry."

00:06:32   It's like the amount of money I'm getting paid kind of outweighs the frustration.

00:06:39   So I'll just kind of stick it out and I'm going to get paid a bunch of money and then

00:06:43   I can take some time off and work on my own stuff.

00:06:45   So that's another important thing.

00:06:50   But then beyond that it's kind of primers around sorts of ideas I would work on and

00:06:55   time frames.

00:06:57   I never commit to releases, I only ever do, you know, I want a block of time or like someone's

00:07:03   like okay you can buy two months of my time for example and great, I'm not committing

00:07:07   to any releases or features or anything really.

00:07:10   They can kind of just do whatever they want with that time.

00:07:12   If they want to change their mind four times and make two different apps, great, I don't

00:07:16   care which has been really nice because it takes all the risk off of me because they're

00:07:21   going to change their mind.

00:07:22   It's always going to happen and now if it's late it's not on me, it's on them because

00:07:26   they change their parameters.

00:07:29   That's been the best thing, is not committing to releases because it takes all the stress

00:07:33   out of it.

00:07:34   It's just like, "I'm going to show up and work and that's it."

00:07:37   It's kind of fascinating.

00:07:38   In some ways, it's almost like you're turning it into...

00:07:41   It's like you're an employee, but it's on a very limited basis in some ways.

00:07:45   It has that same thing.

00:07:46   When you're an employee of somewhere, you're not really committed to a release in a concrete

00:07:51   way.

00:07:52   Or those things, it's like, "Nope, you're just going to keep coming to work and you'll

00:07:55   You'll do your best to get the job done but at the end of the day, it's just your job.

00:08:01   You're just going to go and you're going to keep working at it and it's on them to direct

00:08:04   what you do and how you do it.

00:08:06   I kind of approach it the same way I approach my own products as far as…

00:08:13   I always tell my clients if you're hiring me and you're just sitting in a room and

00:08:15   type like you're spending too much money, there's plenty of people you can hire to

00:08:18   just program.

00:08:19   They're hiring me for all the other added things like input from all the other experience

00:08:26   I have on making all these different apps with consulting over the years and design

00:08:32   input and all this other stuff.

00:08:34   So I'm just running it like I'd be collaborating on a project with a friend a lot of times.

00:08:41   Most projects will come down to or some anyway, they'll disagree with something that I'm

00:08:46   very passionate about and then it's like, "Okay, well, this is something that's just

00:08:49   more of a client thing now."

00:08:51   I'm less of like invested in this like personally but I always like projects that don't come

00:08:57   down to that where I'm like, "This is stupid but I have to finish it."

00:09:00   And the last several have been pretty enjoyable and that hasn't happened which is really nice.

00:09:05   So is it kind of you fall into a pattern where you do consulting for a little while, do a

00:09:12   little consulting for a while, like sort of just build up a reserve and then just take

00:09:16   that reserve and turn it into essentially product?

00:09:19   Like is that kind of, it sounds like what you're saying where you sort of like reserve

00:09:21   just a couple of months of your time, you'll go and be focused on that and then come back

00:09:26   to it?

00:09:27   That's kind of the plan.

00:09:29   It's a lot more informal than that as far as like how I think about it.

00:09:33   For example, last year I did a bunch of work all in a row because I closed several clients

00:09:38   like right after another that were paying like the full rate.

00:09:42   So I figured like well, you know, I don't always have this opportunity.

00:09:45   I might as well go ahead and do it."

00:09:47   And then after I finished targeting my most recent client, I didn't have anything lined

00:09:52   up intentionally and I was like, "You know what?

00:09:54   I'm going to take some time to work on whiskey because I'm excited about it and I've been

00:09:57   working really hard the last several months."

00:10:02   So it kind of varies.

00:10:04   I'd like to do something a little more formal like that.

00:10:06   For example, I have January off and then February, March totally booked.

00:10:11   So hopefully I can take April and May and spend some more time on whiskey.

00:10:16   It just depends on how low I'm willing to let my buffer go before I'm like, "I need

00:10:21   to get some work.

00:10:22   I'm stressed out about this."

00:10:23   Or I suppose how successful your products are too, right?

00:10:25   Yeah, I mean hopefully I can launch whiskey before then and have some actual income.

00:10:29   Yeah.

00:10:30   It's an interesting model though.

00:10:33   I kind of like the philosophy of it because it seems like you're allowing yourself...

00:10:39   You're making sure that you get to do the thing that you really love and want to do

00:10:42   rather than getting sucked into like, "Well, if I worked a little bit more, a little bit

00:10:47   more," you could make more and more money theoretically from consulting and just kind

00:10:51   of get sucked into that full time.

00:10:54   But yeah, I have a lot of demand and I'm definitely like, I feel like if I wanted to, I could

00:10:59   hire some folks and like make a consulting company and do pretty well because I turned

00:11:04   down a ton of projects.

00:11:05   But that's not something I really want to do because there's no end to that.

00:11:09   It's not sustainable at all.

00:11:10   The second you quit working, everyone stops getting paid because you have no actual income.

00:11:16   You're just trading time for money forever which isn't really what I want to do.

00:11:20   I always think I'm pretty goal-oriented and my goal is to do what you're doing basically,

00:11:25   like have my own products that sustain me.

00:11:27   That's always been the dream.

00:11:31   This may sound weird but I definitely go back to we were sitting in Mel's Diner at WWDC one

00:11:37   year and you're like, "Don't do it.

00:11:39   You should totally just stay indie."

00:11:40   I was like, "Ah, alright, you put me over."

00:11:43   And I turned down GitHub and since then every time I'm interviewing someone and almost thinking

00:11:47   about it, I go back to that and I was like, "No, this doesn't further my goals.

00:11:51   You're totally right.

00:11:52   I should keep doing this even though it might be less enjoyable than working at a company.

00:11:57   I'd rather have the flexibility to pursue my goals versus working at a company for many

00:12:02   years doesn't really get me further towards doing that very directly anyway.

00:12:08   So yeah, I mean it's the kind of thing where if you know what you want, then you just kind

00:12:14   of have to keep doing whatever you can to make that happen most directly.

00:12:20   There's nothing wrong with going and working for a company, working for someone else or

00:12:23   doing consulting full time or whatever.

00:12:25   It's kind of just you do what you can in terms of making that work if that's what you like

00:12:30   to do.

00:12:31   else in mind, if working on products

00:12:32   is what really excites you and gets you going,

00:12:34   then pursuing that actively and strongly

00:12:38   makes a lot more sense.

00:12:40   So I remember back that conversation.

00:12:41   I remember us sitting in MEL's talking about it.

00:12:43   And it's funny, because years long ago now, where I--

00:12:51   it's funny.

00:12:51   I might give different advice now in some ways,

00:12:55   having seen how hard it is to actually make

00:12:58   a run at making products.

00:13:01   And having been able to keep at it in my own business,

00:13:04   but it gets harder and harder every day.

00:13:08   But it's definitely-- I think the advice still works, though,

00:13:10   in terms of if you know what you want,

00:13:13   like if making products is really what you enjoy,

00:13:16   then find whatever way you can to make that happen.

00:13:18   Definitely seems to still be good advice,

00:13:22   rather than working towards something

00:13:25   that you don't really want, even if it could potentially

00:13:28   be like whatever, more money or more prestige or whatever like other thing it is that you

00:13:33   could kind of measure and say that you know it was better.

00:13:37   Yeah, well it's interesting.

00:13:39   So like that was right before I launched Cheddar and I was like planning on doing it full time

00:13:44   and you were like encouraging me to do that which was great and I'm so glad I did.

00:13:52   But now I think it's less of a – this is really hard and I know a very small amount

00:13:59   of people that make money on just their own apps and enough to sustain themselves.

00:14:05   But it's kind of like less stressful now.

00:14:07   Before like Cheddar was like this has to succeed or I'm like totally broke and out of money

00:14:11   and this is going to be the worst, which is kind of what happened but I recovered.

00:14:18   But now it's like, "Oh, it's fine.

00:14:20   I'll just go do some consulting for a month or so and build back up my buffer and on to

00:14:26   what I was doing, which is nice.

00:14:29   I'm not like betting my whole livelihood on a text editor succeeding, which is a pretty

00:14:35   dumb thing to do.

00:14:36   So it's nice.

00:14:37   Yeah.

00:14:38   I mean, it reminds me of in a funny way like the thought that just popped in my head.

00:14:41   I had these friends a couple of years ago who the way they structured their life and

00:14:46   their work was they love travel.

00:14:48   That was their thing.

00:14:49   just traveling. That was what they enjoyed most. And so the way they worked is they would just go

00:14:53   and work. They'd pick a trip that they wanted to go on. We went to go and tour Italy. And they

00:14:59   would work out how much that that was going to cost. And they would just go find jobs,

00:15:03   like whatever they could find, work for however long it took to get that amount of money,

00:15:07   like living as cheaply as they could. And as soon as they had the money, they quit their jobs and

00:15:14   I went to Italy.

00:15:15   And I always kind of admired that perspective of just like,

00:15:20   no, this is what I want to do.

00:15:22   The end isn't the job.

00:15:23   The end isn't the money.

00:15:24   The end is the goal of what they wanted to do.

00:15:28   And then in some ways, there's a little bit

00:15:30   of parallel to that of trying to understand--

00:15:33   step zero is understanding what it is you actually want to do.

00:15:36   Absolutely.

00:15:37   And being realistic about that.

00:15:41   I'm curious, actually, what is it about products

00:15:43   that you enjoy most? Like, is it that the freedom to do what you want to do or the,

00:15:48   like, just the process of doing it yourself or people you get to work with in that?

00:15:55   There's a lot of things. I mean, partially of what I'm doing, like my current situation

00:16:00   with like consulting and working on my own stuff, like the freedom to kind of do whatever

00:16:04   I want and just the flexible schedule and where I work and stuff is really nice, but

00:16:10   That's not really a part of making products.

00:16:14   I guess the part that gets me excited is building something that I've envisioned that in theory

00:16:22   will save me time or be very useful to me and then to share about it and everyone be

00:16:27   very excited about it as well.

00:16:30   So to just know that I'm making something that's not just going to spend forever making

00:16:34   this thing and just use it by myself but that all these people are going to be excited and

00:16:40   a lot of using it on a daily basis and maybe I'm helping make their day slightly better.

00:16:47   I think it's just really exciting to build something that is impacting lots of folks.

00:16:52   I guess that's the biggest thing.

00:16:54   I don't know.

00:16:55   Sure.

00:16:56   I guess it's feeling that connection to what you've made something and then someone uses

00:16:59   it and it's a feeling that's hard to describe in a way.

00:17:05   I got an email, I think it was last week or the week before,

00:17:08   from somebody who was using my pedometer app.

00:17:11   And he was talking about it's like this 80-year-old cancer

00:17:14   survivor who said it was a part of their--

00:17:18   getting them healthy after treatment.

00:17:21   And it's one of those like, whoa.

00:17:24   It puts what you're doing in a different perspective.

00:17:28   And being able to have that connection to your work

00:17:31   that even if I've worked-- when I worked in bigger companies

00:17:34   or done consulting.

00:17:35   You get to the end and you ship the thing, it doesn't feel like it was yours in the

00:17:38   same way.

00:17:39   Yeah, I don't know.

00:17:41   When I worked at Hipstamatic, I had a lot of say in things or other companies, whatever.

00:17:49   Or especially at Seesaw, I guess, since I was employee number one and kind of leading

00:17:53   engineering.

00:17:54   But anyway, we'd ship and I was very invested in it as far as my time and thoughts and everything

00:18:00   is this app.

00:18:01   So when people use it, it was the same similar thing although it wasn't all me, it was still

00:18:06   a pretty cool thing.

00:18:07   It's definitely diminished.

00:18:10   Maybe the thing that's more interesting than that as far as – I mean I think that's

00:18:15   just making something in general is exciting to see people use it.

00:18:19   But I think the thing that gets me excited about doing it myself is no one can tell me

00:18:23   that I have to do this like the wrong way in my opinion.

00:18:27   That's been like, especially doing so much consulting, you know some clients like, "No

00:18:32   one has to be this way."

00:18:33   I'm like, "This is stupid but okay."

00:18:35   Like none of that, you know I can make something I'm like totally 100% proud of and not you

00:18:40   know like, "Well this is dumb but I don't have any control over it."

00:18:43   Which has been a theme over a lot of my work over the years.

00:18:46   Or you know, "I built this whole thing and no one's going to launch it or they're going

00:18:49   to mess up the marketing side or you know."

00:18:52   I hand it off this great thing and then they're just going to kill it.

00:18:56   Which has also happened a bunch of times.

00:18:59   Most of the apps I've worked on are in the store.

00:19:01   So I don't know, maybe avoiding that plus a combination of just reaching people like

00:19:07   we were saying.

00:19:08   Yeah.

00:19:09   It is kind of tragic.

00:19:13   Number of friends in the industry who I talk to about who are… the amount of time that

00:19:19   is spent every year building things that never see the light of day.

00:19:25   on the consulting side, on the internal products,

00:19:28   in terms of other--

00:19:29   or it just feels kind of tragic that you

00:19:33   could spend so much time and energy on something,

00:19:35   and then it just ends up not going anywhere.

00:19:38   Yeah.

00:19:40   It's got to be super discouraging.

00:19:43   I mean, there are things that I build that I don't ship,

00:19:45   but it feels slightly different because of a choice I've made.

00:19:49   I make something, and I'm like, yeah,

00:19:50   this isn't actually very good, or it's not as cool

00:19:53   as I thought it would be.

00:19:54   - Yeah.

00:19:55   - Versus someone else, you know,

00:19:57   for somewhere else in the organization,

00:19:59   someone was like, you know,

00:20:00   this isn't really what we want to go

00:20:01   or we've changed direction or.

00:20:04   - Yeah, 'cause at that point

00:20:04   you're just trading time for money.

00:20:05   You're not actually like, you know,

00:20:08   arguably you're not making anything

00:20:09   because you've, whatever you made,

00:20:11   you're just throwing away.

00:20:12   And then you're not getting that reach to people,

00:20:13   which is, you know,

00:20:14   like the very fulfilling part of making things.

00:20:16   It's like, well, I might as well like go,

00:20:18   just go work at Starbucks or something.

00:20:19   Like I'm not doing, I'm not making software here.

00:20:22   I'm just like typing and deleting it.

00:20:24   This is stupid.

00:20:24   So I don't know, I was very discouraged

00:20:28   and it was like earlier in the year,

00:20:31   'cause Seesaw, my previous full-time employer,

00:20:35   sold and then the company that bought it turned it off

00:20:36   and I was like, you know what, that was like

00:20:38   hundreds and hundreds of hours of work

00:20:39   and it's all just gone now.

00:20:41   Like, why am I doing any of this?

00:20:42   This is so stupid.

00:20:44   So I was like, you know what, I'm gonna do hardware.

00:20:45   And I worked on a hardware product

00:20:47   for like the first two months and then ran out of money

00:20:49   and I was like, all right, time to do some consulting.

00:20:52   And through that process, this is lightly, I kind of like started enjoying iOS again.

00:20:58   But yeah, recently I was very like, I hate all of this.

00:21:01   I'm done with this like stupid silly loop of building things and throwing them away.

00:21:05   So it also helped like focus on my own projects a little more than just like aimlessly consulting,

00:21:12   which has been good.

00:21:14   So yeah, one of the interesting things.

00:21:17   So I remember, if I'm remembering right,

00:21:19   Cheddar, which was your sort of to-do manager app,

00:21:22   what you did as a subscription, if I'm remembering that.

00:21:25   Am I remembering that right?

00:21:26   Yeah.

00:21:26   It was like a sort of like a freemium subscription

00:21:29   kind of model.

00:21:31   And it seems like where you're heading now

00:21:33   with your newer stuff--

00:21:35   I don't know if it's been fully specified with Whiskey, which

00:21:38   in case anyone doesn't know, it's a markdown editor.

00:21:42   It's like it seems you're heading more towards the--

00:21:46   like classic products that you buy rather than services

00:21:51   that you subscribe to.

00:21:54   And I was curious if that's just happenstance

00:21:57   or if that's based on your experience

00:21:58   that you had with Cheddar in terms of if the goal is to make

00:22:04   that the focus, if that's an intentional turn away or change

00:22:10   or if it's just the way it happened to work out.

00:22:13   - Yeah, it's definitely intentional.

00:22:15   Kind of the idea is like, so Cheddar didn't do well,

00:22:21   especially that freemium model.

00:22:22   And it's like a, so the pricing was it was a free app,

00:22:26   you got unlimited lists, unlimited tasks if you paid.

00:22:30   And if you didn't pay, all the same stuff,

00:22:32   you only just had two lists.

00:22:34   So I made it like two bucks a month,

00:22:36   which is like as high as it seemed reasonable

00:22:38   to charge for unlimited lists and a to-do app,

00:22:42   which seems super arbitrary and people are like, "Well, there's all these other free

00:22:44   to-do apps.

00:22:45   Why would I pay for this one?"

00:22:46   Sure.

00:22:47   I mean, it's sinking and there's reasons but it seemed just so arbitrary to charge $2 for

00:22:52   a to-do list and a lot of people didn't pay it.

00:22:55   So I was like, "Okay, I need to do a business plan and maybe I can make some money off of

00:22:59   this."

00:23:00   I ran out of time before I got there.

00:23:02   I ran out of money rather.

00:23:04   So I feel like if I make anything similar, like some sort of platform that's useful,

00:23:11   some utility, a lot of people wouldn't justify paying for it.

00:23:15   So I just like, you know what, I need to come up with something better and I know like there

00:23:20   are several markdown editors that do very well as far as like multiple, like run a multiple

00:23:25   person company off of just the income from that.

00:23:29   So I was like okay, well there's some money in this market and it's something I'm very

00:23:33   passionate about.

00:23:34   Like Cheddar had a lot of markdown features.

00:23:36   I've been like really in love with markdown for many years.

00:23:40   So I was like, you know what, I'm just going to do something regular.

00:23:42   I don't have to deal with servers or things being down or browser bugs.

00:23:47   I'm just going to build a regular old app.

00:23:50   Like it's going to charge one time and I'll get all my money and move on.

00:23:54   Maybe I'll do something like Sketch.

00:23:55   If I put out a huge update, I'll make it a separate app and you have to buy it again.

00:24:00   I don't know.

00:24:01   That's more complicated though since there's iCloud stuff involved with that.

00:24:05   Or maybe not now with iCloud Drive I guess.

00:24:09   It was kind of just like, you know what, I'm bad at services, I've learned.

00:24:16   I really enjoy making web services but running a service and charging, it's just another

00:24:21   level of commitment I feel like.

00:24:23   If a server's down, people are going to complain versus a text editor, someone has a problem

00:24:30   with it, cool, I'll get to it when I get to it and it's not that big of a deal.

00:24:34   I think that matches up a lot with my experience.

00:24:36   It's just like I have things on both sides.

00:24:38   Like I have-- like Feed Wrangler,

00:24:40   which is like a subscription-based,

00:24:43   or I have things that are just straightforward transactions.

00:24:48   And there's certainly a lot less anxiety

00:24:50   about the things that are straightforward.

00:24:51   It's like the person buys it, they like it, great.

00:24:54   If they don't like it, they complain to Apple

00:24:56   and they'll get a refund.

00:24:57   And it's just not--

00:24:59   there is-- obviously there's pros and cons.

00:25:02   It's nice.

00:25:02   But a subscription, it's nice.

00:25:04   theory recurs and goes on into the future.

00:25:07   But there's something also kind of nice about having it be super straightforward.

00:25:12   Everyone knows exactly what they're getting in the transaction.

00:25:16   You're giving them some software, they're giving you some money, and that's that.

00:25:21   Yeah.

00:25:22   I mean, also, it's a lot more freedom.

00:25:24   So for example, when I was doing Cheddar and then got hired at Seesaw, I still had Cheddar

00:25:29   for a bit before I sold it.

00:25:31   And I sold it because it was just overwhelming.

00:25:33   Running a service, even though I wasn't doing hardly any engineering, just support and answering

00:25:38   questions and all that sort of stuff was really overwhelming as far as the amount of free

00:25:43   time I was taking.

00:25:44   I feel like something like a text editor, you can build up a good enough FAQ and alright,

00:25:53   we've answered everything.

00:25:54   It's a text editor.

00:25:55   Just type in the text editor.

00:25:58   So if I were to take a full-time job or something and still had whiskey, it would be very low

00:26:02   stress versus if I had some web service or even I'd considered building a web service

00:26:08   for like syncing notes that was basically whiskey with a backing service and a web app.

00:26:13   And I think that would be way more stressful.

00:26:15   So I mean I like the idea of not being super tied down to – I feel like once – like

00:26:20   for example if you decided to like quit updating one of your apps which I'm sure there are

00:26:23   several you don't work on since you have so many, it's not that big of a deal versus

00:26:27   I feel like if you just totally ignored your service, you can't really do that.

00:26:33   Yeah.

00:26:34   I mean, it's interesting.

00:26:35   I guess in some ways, it's that there's a difference in some ways of the difference

00:26:39   between it being passive versus active.

00:26:42   That there is something kind of-- and I've noticed this myself.

00:26:46   I'm more and more trying to avoid things that are active.

00:26:50   Or maybe an embedded word is synchronous versus asynchronous.

00:26:55   If the thing that I made, it just exists off on its own and it is completely self-sufficient.

00:27:03   I do it, I put it out there, someone can use it, that's great.

00:27:07   Versus in order for it to be useful, it has to be constantly interacting with something

00:27:11   that I control or manage.

00:27:15   Every time recently that I've done that, it just adds more complexity to my life in a

00:27:22   in a way that the products that I've made that are largely

00:27:25   self-sufficient--

00:27:27   like I have a recipe organizer.

00:27:30   It's essentially self-sufficient.

00:27:31   Like the person gets it, and they're adding recipes to it.

00:27:34   But it's mostly on them versus things

00:27:37   that are deeply active.

00:27:40   There's always things to be doing,

00:27:42   because it's sort of built in that way that, fundamentally,

00:27:46   it can't just be standalone running on--

00:27:49   it's like it's running on their hardware.

00:27:51   their network.

00:27:52   It's all the stuff that's just on them.

00:27:54   Right.

00:27:55   Yeah, I feel like a lot of what Cheddar, especially the service, people were excited about it

00:27:59   because I was updating it constantly.

00:28:02   It was very tied to my personal brand as far as I'm involved so people like it.

00:28:07   It doesn't necessarily mean Cheddar is great.

00:28:11   I think some people liked it because it was good in my opinion.

00:28:15   It was very tied to I'm working on it and me.

00:28:17   I think that could be said for a decent amount of your products as well.

00:28:21   You know people are just fans of you so they're going to get all of your stuff.

00:28:24   So when I quit working on Cheddar full time, everyone is like well I'm going to quit

00:28:27   using this now because I know Sam is not working on it anymore and the whole point of this

00:28:32   was to see it kind of progress and that's stopping so I've lost interest.

00:28:36   I feel like that expectation isn't really there with a standalone native app.

00:28:41   And that was kind of like I've just done…

00:28:43   I just sold Rune like two weeks ago and that was a service, a blogging service, which is

00:28:49   a pretty intense project.

00:28:54   I started whiskey like right after or actually after selling cheddar I guess.

00:28:58   So it was kind of like I'm going to work on something next that's going to be simple and

00:29:01   stand alone.

00:29:02   I don't want to deal with any of this.

00:29:03   I'm not saying I won't ever do it in the future but this is like my next project and it's

00:29:07   just taken me a really long time to build.

00:29:09   I started it last December and I'm still working on it.

00:29:12   Granted I've done a lot of full-time freelance since then.

00:29:15   Yeah.

00:29:16   But it's funny.

00:29:17   One of the things that reminds me of is how I'm often so envious of game developers.

00:29:23   Where I think about people who make products, who make games, where it's not uncommon for

00:29:29   a game to be released and then never updated again.

00:29:34   Or never like has one little bug fix update and then that's it.

00:29:39   And yet, it probably the hours that are spent in that app and using it are dwarf anything

00:29:47   that I've ever made.

00:29:49   Because it's a different set of expectations.

00:29:51   Like customers don't necessarily expect there to be a constant stream of like making the

00:29:57   game doesn't necessarily like need to be constantly updated and improved or added new features

00:30:01   to it.

00:30:02   Like it's a different kind of like treadmill that they're on where they can just drop it

00:30:04   in.

00:30:06   And then it's the same thing forever.

00:30:09   Yeah, it's interesting.

00:30:12   I've been talking with a couple of folks about this kind of idea of apps as pieces of art.

00:30:19   More designer friends as you probably guess.

00:30:23   When they're like, "I'm making a piece that's via paint or whatever medium," you kind of

00:30:30   spend all this time and energy on it making this great thing and then you're like, "Alright,

00:30:33   here it is.

00:30:34   You can enjoy it now.

00:30:35   And with apps, is that a thing we can even do?

00:30:38   I mean, you at least need an update once a year when the new OS comes out and breaks

00:30:43   everything.

00:30:46   But I feel like that's not something that, at least in our genre of apps, isn't really

00:30:51   possible.

00:30:52   But for a game, I think it's totally possible because it's so enjoyable on its own versus

00:30:57   I feel like the content of the game is the gameplay versus I feel like the content of

00:31:01   a lot of the things we create is us adding new features.

00:31:05   The app is the content versus a game,

00:31:09   the content is the experience, which is interesting

00:31:13   to think about.

00:31:14   I mean, it's definitely something

00:31:15   that I've been thinking about a lot.

00:31:19   How could I get into that racket?

00:31:22   It seems awesome to have the experience of I

00:31:25   build something, I put a lot of time energy into it,

00:31:29   They put it out there.

00:31:30   And in some ways, it almost seems like--

00:31:32   they just move on.

00:31:33   And it just sits there merrily, I guess,

00:31:38   merrily getting revenue without really-- and everybody's happy.

00:31:44   It's not like people are complaining that, where's

00:31:48   my new update?

00:31:51   It seems like everyone's happy.

00:31:52   But for productivity or utility apps,

00:31:56   There's this different mentality that everyone has.

00:31:59   Or it's like, is that on us?

00:32:00   Are we just thinking that adding features is, well,

00:32:04   that's what we do.

00:32:05   And we don't actually really need to.

00:32:08   I don't know.

00:32:08   Interesting.

00:32:09   So I count seven apps on your page.

00:32:11   Is that all you have in the store, or do you have more?

00:32:14   I have many more in the store.

00:32:15   OK, yeah.

00:32:16   So recently I've been going through this thing

00:32:19   of trying to simplify, because I had so many projects.

00:32:24   So I've recently just sold and gotten rid of all of them except for two and one I just

00:32:29   open sourced and kind of will probably not work on anymore unless I get some PRs and

00:32:35   submit them and still work on whiskey.

00:32:38   So it's basically like shares and whiskey and then coins is now open source and it's

00:32:42   free and people do whatever.

00:32:45   Do you like gracefully abandon things or are you just kind of like, "Well, I'm just

00:32:48   going to leave it there and kind of forget about it."

00:32:50   How do you handle that because you have so many projects.

00:32:53   To me that was super overwhelming.

00:32:55   I just need to focus on whiskey and try to ship this thing.

00:32:58   It's been forever.

00:32:59   I don't have time to deal with feature requests for all these other things.

00:33:04   It's funny because I feel like I get, at a certain point, I just got used, I just got

00:33:09   comfortable with knowing that I'm never going to be able to please everybody, which is,

00:33:16   in some ways, kind of obvious that you can never please everybody, but it took a long

00:33:20   time before I would give myself permission to believe that, I think. That like, you know

00:33:25   what, like, there are going to be people who are grumpy about the thing that I made, but

00:33:29   even if I change what they're asking for, it's someone else is going to be grumpy. And

00:33:34   like, there's a never ending supply of grumpy people. And so I just, at some point, you

00:33:39   just have to get used to the fact that that's gonna, that's just like, that's just life.

00:33:43   And so for me, I think I just, it's sort of like, like, intentional neglect, maybe is

00:33:51   like the good like kind of phrase for what I tend to do where I'll get something to a

00:33:55   point that I think it's pretty solid.

00:33:56   I think it's useful.

00:33:57   Like it's not nothing's broken, broken.

00:34:01   Like it's, you know, not crashing all the time.

00:34:03   It's kind of working.

00:34:05   And then I'll just like, leave it there.

00:34:10   And as much as I can, it'll just kind of run along on its own until such time as either

00:34:16   it's-- if something does break, like iOS 8 comes out or a new device comes out or something

00:34:22   like that, where either it's compelling for me to build something, where I look at it

00:34:26   and I'm like, oh, man, this would be so much better.

00:34:29   I could take advantage of whatever.

00:34:30   I could make an Apple Watch thing for this.

00:34:32   I could make an iPad version for this.

00:34:34   I can take advantage of something that's really cool and affirm that it makes me excited.

00:34:39   then I'll go ahead and build that.

00:34:41   Or if iOS update breaks it, then it's like, well,

00:34:43   either I have to decide, do I want to keep working on this,

00:34:46   or do I want to pull it?

00:34:47   And typically, what others end up doing is I'll just

00:34:49   do enough work to get it working again and move on.

00:34:53   Move on again, put it back on the shelf,

00:34:55   and let it kind of sit there.

00:34:57   Because in some ways, I think it's a funny thing.

00:35:00   If you spend too much time in our little world of developers

00:35:04   and designers, it's easy to realize

00:35:06   that most of your customers don't care about things

00:35:10   in the same way that you care about things,

00:35:12   that they are perfectly happy using the thing the way

00:35:16   they've always been using it.

00:35:17   And in some ways, I've had-- some of the biggest explosions

00:35:24   of customer anger against me are when I--

00:35:27   I thought I was making the app better.

00:35:29   And I changed-- did a big update.

00:35:32   And it's totally fresh, super cool.

00:35:35   And I put it out there and I liked it the old way.

00:35:38   Why did you bring it?

00:35:39   I got used to it the other way.

00:35:40   I liked the way it worked the other way.

00:35:43   And at a certain point, you're just kind of like,

00:35:45   well, maybe I'll just leave it that way.

00:35:47   And the people who like it now will continue to like it.

00:35:50   And I can worry about-- rather than worrying

00:35:52   about trying to invent and carry along this group of people,

00:35:57   I can just work on something new and put it up next to it

00:36:00   and find a new market for it and find a new group of people.

00:36:04   But that's kind of the approach I take.

00:36:06   And so far, it's been worked all right.

00:36:07   There are certainly apps in the store

00:36:09   that don't get really any love or attention from me.

00:36:14   And they continue kind of off doing their thing.

00:36:18   And I think, functionally, that's the only way

00:36:21   that I've been able to keep doing what I do.

00:36:23   Because if I didn't do that, if I

00:36:25   felt like I had to be always working on everything,

00:36:29   then I'd never--

00:36:30   I'd just be paralyzing.

00:36:32   And so I just kind of get used to the fact

00:36:34   that there are a lot of things that I could be doing that I

00:36:38   don't.

00:36:40   But as long as things aren't totally broken,

00:36:43   people are happier than you'd think they would be, I suppose.

00:36:46   Yeah.

00:36:47   Interesting.

00:36:49   Yeah, that's good.

00:36:50   Yeah, I don't know.

00:36:52   I guess it's a funny thing to say.

00:36:53   But it's a weird thing for, I think,

00:36:54   a lot of in our kind of--

00:36:57   like Apple development generally, I think,

00:37:00   kind of engenders this feeling of perfectionism, maybe.

00:37:05   But you can take the other extreme

00:37:09   as extreme pragmatism and being like, well, if it works,

00:37:13   it works.

00:37:13   And rather than sitting there having this feeling,

00:37:18   you have to keep making it better and better.

00:37:21   You just kind of let it do its thing.

00:37:22   And I guess maybe picking up what

00:37:24   we were saying a minute ago, if you can try and make it

00:37:26   so that it's kind of self-sufficient,

00:37:28   that whatever, like my pedometer app,

00:37:32   it's entirely self-sufficient.

00:37:33   It just sits there because it's all

00:37:35   based on the data on the person's phone.

00:37:37   It doesn't matter if-- there's nothing for me to do with that.

00:37:42   I could add new features to it and certainly have

00:37:44   a roadmap of stuff that I've thought about.

00:37:46   But I am able to just kind of push it off to the side

00:37:51   and look onto the next thing.

00:37:52   And once you get comfortable with that,

00:37:55   It's taken me years to get feel like I can just say that's no, that's fine.

00:38:00   I'm not.

00:38:00   I'm just not going to think about that app for a while.

00:38:03   And then, but it's, you know, it still sits there, make making some money for me.

00:38:08   And like a lot of, like a lot of my products don't make very much money on

00:38:11   their own.

00:38:12   Like they wouldn't be a business.

00:38:13   I couldn't sustain myself on their own, but once you get a handful of things that

00:38:18   you can or that in aggregate means you can.

00:38:21   Right.

00:38:24   I had kind of gone down the path of I'd like to focus on one thing and put all my effort

00:38:29   into that and be in whiskey now and maybe something else down the road.

00:38:35   So I was just shedding all of my things.

00:38:39   But I don't know, maybe that was the wrong call.

00:38:41   Well, it's just different.

00:38:42   This is the fascinating thing and this is why I thought it would be great to have you

00:38:45   on because it's easy to romanticize making a living from products.

00:38:54   know a lot of people who I talk to in a community about what I

00:38:58   do. And it's like, I mean, you think you've been said it's like,

00:39:00   it's sort of like, oh, living the dream, right? Oh, I make my

00:39:02   living from products. It's like, no, it's actually like, in some

00:39:05   ways, I look like the dream from like, when I dream, I dream in

00:39:08   some ways of just like having a regular job. Like, this can be

00:39:13   more of the nightmare sometimes, because it's really hard. It's

00:39:17   enjoyable. Like I, I do it because I enjoy doing it. And

00:39:21   Like, it allows me to do things that aren't work that I really love.

00:39:27   Like the things that it allows me to do in my, you know, just in life more generally.

00:39:31   But it's like, it's really hard to make a living from products.

00:39:34   It's not, it's not necessarily always awesome.

00:39:38   Like you hear about all the, you hear about all the, you see this, you know, like the

00:39:42   few successes in the world.

00:39:45   And it's easy to want to do it.

00:39:46   But the reality is, it's like, no, more like I've shipped probably-- I don't even know

00:39:52   what it is at this point.

00:39:53   It's a pretty high failure rate.

00:39:55   And that's pretty discouraging.

00:39:57   When you ship something out, you put a lot of time into something, it goes out into the

00:39:59   world, and then no one cares.

00:40:02   And that's pretty common for products.

00:40:05   And the reality is that's just the way it is.

00:40:09   You just have to be able to keep at it, I suppose.

00:40:16   - Yeah, it's really interesting too,

00:40:18   'cause you're not in San Francisco obviously.

00:40:21   And here doing this is kind of like, why would you do that?

00:40:25   It's kind of the attitude.

00:40:27   The thing here is to go raise some money

00:40:28   and start some venture-funded company

00:40:30   and flip it after a year or two

00:40:33   and not actually make things that make money.

00:40:35   So it's kind of interesting to be in this world.

00:40:39   Well, I kind of trust out of it,

00:40:41   but in the city, I guess that's the world

00:40:44   of that sort of mindset.

00:40:45   I just want to make something that makes enough money to comfortably live.

00:40:49   I'm not necessarily interested in making hundreds of millions of dollars.

00:40:53   Sure, that would be pretty cool, but that's not the goal.

00:40:57   The goal is to live off my products.

00:40:59   I think if the goal is to make hundreds of millions of dollars, go work at some startup

00:41:03   and keep playing the lottery on that front instead of playing the lottery on the product

00:41:07   front.

00:41:08   I don't know.

00:41:09   It's interesting.

00:41:10   It's yeah, it's it. I don't think I'd work. I don't think I fit in very well out in San Francisco. Like, every now and then I have conversations with like, I guess I guess you caught like recruiters or people like that who kind of like trying to, and you kind of describe what I do. It's like, I don't really get what you're doing. Like, why aren't you like, why don't you, you know, why don't you get some some funding and hire, hire 10 to hire 10, you know, hire 10 engineers and two designers and go crazy, like, you know, see if you can blow it up. It's like, well, I guess but

00:41:40   that sounds more like that sounds exhausting. Like, I'd

00:41:44   rather, I'd rather not, I'd rather just kind of tinker away

00:41:49   in my basement, I suppose, rather than that, than worrying

00:41:54   about that. Yeah. Like, I don't even know. Of course, it's like

00:41:58   living in San Francisco, like it sounds super expensive to it is

00:42:03   very expensive. Like that's why everyone has to make hundreds of

00:42:05   millions of dollars on their, their stuff. So that's, that's

00:42:08   That's how they're gonna pay rent.

00:42:10   - Yeah.

00:42:11   - And it's just like this very crazy self-fulfilling

00:42:14   kind of mindset where you're,

00:42:18   the goal is to go big.

00:42:21   And that's your definition of success

00:42:23   rather than your definition of success

00:42:27   just being like a normal, comfortable life

00:42:31   that where you can kind of do what you wanna do, I suppose.

00:42:33   - Yeah.

00:42:35   I have a number in mind that's fairly low, less than I've made at other companies definitely

00:42:41   of an annual total income and once that is achieved I can fulfill all of my expenses

00:42:49   and live comfortably and great, now I'm doing what I want to do.

00:42:54   I can work for myself.

00:42:55   That's been the goal.

00:42:57   I don't really count consulting and working for myself.

00:42:59   >> No, it's definitely different.

00:43:02   It's that, but I don't know.

00:43:05   Maybe we'll get there with whiskey, I suppose.

00:43:07   >> I don't know.

00:43:08   I mean, I'm not that optimistic about it personally.

00:43:10   Like, a lot of people are really excited about whiskey and personally I'm very excited about

00:43:15   it just as something I'd like to exist, but I don't think that -- I have a hard time believing

00:43:22   that just the traditional app model will do that well.

00:43:26   I feel like subscription has to be the thing or it won't be successful long term because

00:43:31   a year from now, everyone has it like, "Okay, now what?

00:43:34   I've made all my money."

00:43:37   But I don't know how I can make whiskey a subscription.

00:43:40   That would be ridiculous.

00:43:42   It's a subscription for a text editor.

00:43:47   I considered in-app purchases for like deep integrations.

00:43:50   So like a super deep integration with like Cloud App for example or Dropbox or Evernote

00:43:55   or something like that and you can purchase a big add-on.

00:43:59   But still it's not that sustainable and I feel like it would just make people mad that

00:44:03   they paid 20 bucks for a text editor and have to pay even more money to get all the features.

00:44:09   So I don't know but I'm just trying to finish it and then I'll figure out all that stuff

00:44:12   I guess.

00:44:13   But I think the thing that the experience that I've had is you have a big surge of people

00:44:20   at the beginning, like the normal kind of like you have a big launch hopefully, better

00:44:24   press, get a bunch of kind of like a big wave of money to try and kind of pay off the development

00:44:29   time. And then it settles down. And as long as where it'll settle down at some point,

00:44:34   and hopefully that point doesn't have to be what your goal is. That point just has to

00:44:40   be something. And then this, I guess my model is then I'll start working on something else

00:44:45   and hope to eventually over time layer more and more of those on top of each other. Because

00:44:51   avoids the like, a year later everyone has it, now what do I do?

00:44:55   It's like, well, what you do is for the last nine months you've been working on something

00:44:59   else to be your next thing, to layer on top and then layer on top of that and layer on

00:45:05   top of that.

00:45:07   Being all in on one product is really hard to feel stable or to feel secure.

00:45:12   Yeah.

00:45:13   Interesting.

00:45:14   I like that a lot.

00:45:17   Because making something new is exciting.

00:45:18   Yeah.

00:45:19   I mean, it's the best part.

00:45:20   >> Yes, for sure. Interesting. This has been a significant conversation.

00:45:27   >> Sure. I'm glad. It's fun. Hopefully it was useful to other people, too. I get a lot

00:45:33   of feedback from people who talk about, "Oh, I want to make products. I want to do it."

00:45:39   It's like, "Well, do you? What does that mean to you? What are you actually trying to accomplish?"

00:45:44   Hopefully we've dealt with some of those. I'm glad you said yes to come on and talk

00:45:49   about it.

00:45:50   So I guess I'll probably wrap up there.

00:45:54   If people want to reach out to you, feedback, what's the best place for them to find you

00:45:58   online?

00:45:59   I'm Sophis, S-O-F-F-E-S on everything.

00:46:04   So Twitter, GitHub, whatever.

00:46:06   Great.

00:46:07   And I guess be looking for…Whiskey is in open beta now, right?

00:46:13   Yes, it's useWhiskey.com if you want to check it out.

00:46:16   Great.

00:46:17   I love that it's almost like watching it come to life in real time.

00:46:21   I've been using it since the first beta and the app is a totally different app now than

00:46:26   it was then in terms of functionality and it's kind of like watching it be assembled

00:46:31   in front of me so that's kind of cool.

00:46:32   I recommend that experience to anyone else if you write in Markdown which you probably

00:46:38   should.

00:46:39   Yeah, I just started tracking my issues in the public as well on GitHub and I'm pretty

00:46:45   open about all of it.

00:46:46   even live stream working on it in Xcode and whatnot.

00:46:50   It's been really good to have people excited about it before launching because it's taken

00:46:54   so long.

00:46:55   I kind of lost interest.

00:46:57   So I'm getting some of that nice, fuzzy product reach feeling before I'm finished.

00:47:03   So it's kind of helping me stay motivated.

00:47:05   I recommend it.

00:47:06   Nice.

00:47:07   Yeah, that seems like a pretty good approach.

00:47:09   You'll have to start doing that, start live coding my coding sessions.

00:47:15   It's just like me messing around, working on some feature.

00:47:18   And then I get tweets all the time like, "Hey, are you doing another one of those soon?"

00:47:22   I mean, I guess.

00:47:23   I'm just typing right now.

00:47:24   If you want to watch, okay, I guess.

00:47:27   There you go.

00:47:28   It's performance art.

00:47:29   Yeah, yeah.

00:47:30   All right, great.

00:47:31   So anyway, thank you so much for coming on.

00:47:34   I really appreciate it and talk soon, I guess.

00:47:37   Yeah, thank you.

00:47:38   Thank you.