Sam Soffes / Seesaw - Part 3

Well, we’re back. This is a part three, Sam…

Part three, I’m honored. Only part three so far, so it’s great.

Yeah, I’ve never done a part three on this show before. I’ve never done a part three show of anything, actually. So that’s a first of firsts.

It’s an honor.

I’m actually excited to have you back on the show, because I think a lot of people look up to you, both your courage to do what you’ve done, to start your own company, and just in general, they’re fans of Sam, that’s what I like to say. They wanna see you succeed; you’ve got a lot of fans out there that really wanna see you do some awesome stuff, they enjoy the stuff you’ve built… And for those who are listening that are catching up, if this is the first of Sam’s show you’ve listened to, you should probably push pause or just stop or whichever makes the most sense, and go find part one and part two and listen to those and then come back and listen to this, and pick up where we’re about to leave off.

Part one, Sam, was pretty much your history, and part two was pretty much product-focused. We talked about Cheddar a lot, we talked about Nothing Magical… I can’t recall all the nuances we talked about, but that’s the gist. And I guess just for lack of those who may not know who you are, who exactly are you?

That’s a deep question.

It’s changed, right? It’s changed a lot. No pun intended.

Well, I guess I’m primarily an engineer and designer. I worked on a lot of different stuff, so… I don’t know. I made this product called Cheddar, and yeah, some other stuff. I mean, listen to one and two, there’s a lot.

Yeah, listen to one and two. That’s your intro, you’ve got like two hours of intro, basically; two shows.

Yeah, that’s good. I mean, more than you’d want to know about me, it’s there.

Yeah, and some personal stuff, and we’ll probably get into some personal stuff in this show as well… So recently, 13th November - not long ago, earlier last month - you had posted this latest blog post, which I guess is essentially a bullet point list of things we can talk about. We’re not gonna dive into each and every one of these and just basically dissect this post, but they certainly provide a guideline for this conversation we can have. I like the way you open that post up where you say “My work history is pretty hilarious”, and I thought that was pretty much the case when we’ve talked in part one and part two… If you were in any other industry and you looked at your resume, you’d be like “What’s wrong with this guy?”

It’s pretty funny, friends here don’t understand. Like, “You haven’t had a job for more than a year?” I was like, “Well, I had one for a year and two months.” They’re like, “I don’t understand.” I don’t know, if you think about it, the iPad came out 3-4 years ago; things change pretty quickly. The iPhone was even out five years ago.

That’s an entire new economy based on that thing that wasn’t there, and ways of life, new types of businesses…

Yeah.

…new studios that are totally focused on iPad-only applications, or iPad-only design studios, you know?

Yeah, it’s insane how quickly things change. I mean, if I didn’t do my own thing, I would have gone to college and graduated a year ago, and I’d still be at my first job, I’d be a junior engineer, not doing anything useful… Versus like changing jobs a lot - it’s been great, because I’ve had a lot of different experiences, things that I wouldn’t have done otherwise. It’s the same with contract work; just doing all these different projects is interesting and really great.

You know, I have this saying that I lean on that was actually sung by – I’m gonna look up the song while you’re responding, but in this song he basically says “My scars are who I am”, and he talks about his path in life. You’ve had kind of a unique path in this work history. You just said that if you had gone to university or to college, that you would have graduated last year and you’d probably still be a wet behind the ears engineer, too. So what do you say about your path when somebody asks you about what you’ve learned on your path?

Yeah, I mean… A lot of people ask “Should I go to college?” because I didn’t, and I make that pretty well known. We talked about this a lot before, I guess, but it’s like, if you’re doing computer science, you don’t necessarily have to – like, not going to college I think I learned way more than if I had, just from like learning professionalism, and the different things of like having jobs, and how silly HR is, and all this stuff that you don’t learn… I don’t know, I’m really happy with the places I’ve worked, even the places I’ve worked that in hindsight I didn’t like – or I guess at the time I didn’t like, but in hindsight I’m glad I had those experiences. Regretting your past constantly doesn’t do anything for you. It’s already done. Learn from it and move on.

And for those who happen to be curious about the song I was talking about, the artist name is Nathan Lee, and the song is “You’re not alone.” It’s a pretty deep song, so if you listen to it… It’s not a love song, but it’s a love song in some sort of way, and that’s all I’m gonna say about that.

You and I are on the same page when it comes to the education thing, because – not so much education, I guess going to school. I didn’t go to university or college either. I went into the military when I was 18, served the country, got out, was an idiot, drank too much, did stupid things, and I guess after saying the next thing I’m gonna say, or after I say “did stupid things”, I got married at a very young age, far younger than I probably should have, but… Something beautiful came from that. I have an awesome daughter, she’s gonna be nine years old this January. So one of the best parts of my life is from some of the stupidest things you do. Great things can come from and do come from times in your life when you’re just an idiot, and you’re just kind of bouncing around.

At the same time, I’m a product manager at Pure Charity, I’ve done a lot of cool stuff in the web industry, and like you, I’ve got some battle scars, but I didn’t go to school either… And had I gone to school, maybe I wouldn’t have had the opportunities that I had, or met the people I met, or have the same outlook I have on this chaotic, uncertain industry that we work in, where it’s okay to bounce around like we do.

Yeah. Well, it’s funny because I’m seeing as I write this post and I can announce all this stuff and everytime I have a post with this kind of title, I have one of my friends - we were roommates in 2008 or something - who laughs at me every time, like “Oh, he’s changing jobs again.” At one point he and another friend had a running bet on how long I’d be at a job.

[laughs] That’s not nice

So it’s like, “Well, it’s funny, I don’t care anymore. Yes, I’m changing jobs, don’t worry about it.”

That’s fine. There’s no problem with that. So let’s talk about change then. We dove in your history in part one, we talked deeply about Nothing Magical and your product Cheddar in part two, but things have in fact changed. You’ve got Nothing Magical still there, you’ve got Cheddar still out there, but what’s come of your life recently?

So I no longer do Nothing Magical full-time, which is a big change. I have a real job again and I live in Kentucky now, not in San Francisco, and I’m also engaged. So lots of big stuff. That’s like the bullet points I guess of all the changes.

That is all the bullet points, and when you were on the show last time you were talking about how you had an ideal apartment that you wanted to rent, and how much it might be or it might not be, and that was in San Francisco, and I believe you even said that you would never leave or that you would never desire to leave San Francisco.

Indeed. I definitely said that.

But you did leave San Francisco.

I am sitting in cold, rainy Kentucky right now, so it’s good. Yeah, so I moved shortly after we talked last in San Francisco to just a cheaper apartment. I was saying I wanted to get a studio because I didn’t have any stuff and it was awesome, but then I got a one-bedroom apartment instead of a studio. I was really happy with it, I started to get stuff again, and then kind of after I got settled, just got a bunch of stuff again after not having anything, and moved to Louisville.

And you moved all your stuff.

I did, and it was really painful and expensive, so…

Yeah, it would have been a lot easier if you just kept not having stuff, right?

I know, as I was packing all of it, it’s like “I haven’t even used this yet. I just got it.”

“It’s still in the box! I’ll just not open it. I’ll open it in Louisville.” That’s crazy. So let’s rewind and talk about what happened at Nothing Magical. There’s some key events I wanna key in on there. You ran out of money, you had an opportunity to take on a co-founder, that didn’t quite happen, and I think the running out of money part - which came first? Was it the being turned down, or was it the running out of money part first? Which came first?

It was kind of all the same. I had the summer before - or two summers before; the summer before; I don’t know… The summer before, yes. Okay, whatever. I worked for Hipstamatic before I was an employee there, as contract, and they were paying a lot, an absurd amount. So I just had like, I don’t know, a lot in savings. 50k, 60k, or something, and I had put it all on Apple stock, which turned out to be a really great investment. So I was just living on my Apple stock when I left Hipstamatic. I was like “I’ve got this, I have a huge runway, I can make it to the end of the year no problem. I’ll be way profitable before then.” You know, a little cocky.

Then I got into it a couple months in… I didn’t really change how I was living. I mean, I sold all my stuff, but I still definitely wasn’t living as lean as I could have. And my apartment was like $3,200/month, which is absurd. I mean, San Francisco is expensive… But it was a really nice apartment, even in San Francisco. So my burn was just a lot, I was going through a lot each month, and got down to I guess - in what month, September? I don’t know. I was like “Okay, this is a problem, I’m going to run out of money. I need to get a new apartment, and I don’t know if I can afford a deposit on any one. This is gonna be interesting.”

So I was thinking about maybe I’ll raise some money so I can keep doing Nothing Magical, and went in and got my – so Nothing Magical was a Delaware incorporation. I was getting a bank account set up at Silicon Valley Bank, even though I never finished that, because that’s a lot of work… And then I just started talking to people, different investors or friends or angels or whatever, and I was like, “Yeah, here’s what I made. It does pretty well, but I don’t wanna make productivity apps, I wanna make something else.” Cheddar is fun and I like making it because it’s a product, but I don’t enjoy to-do apps. I don’t think anyone really gets excited about to-do lists.

Can we camp out there for a second? So if you don’t like to-do apps, why would you base your entire burn rate, your run rate and all that stuff on that one – I mean, I know you had other ideas obviously, but that was the one you were devoting all of your time to.

Yeah, I mean, when I was leaving Hipstamatic I decided to leave, and there was actually - the last time we didn’t talk about this… There was a huge – I think it’s Inc. Magazine (inc.com I think) did a big story on Hipstamatic and everything that happened, and the story behind me leaving… It’s pretty funny. Anyway.

Wow…

We can talk about that if you want.

You’re famous, huh?

Well, it was like – I’d been in Inc. before once, because I was complaining at some guy and they quoted my tweet of me complaining to this guy… It was like, “Yeah, I’m in this magazine for complaining on Twitter! This is awesome!” And I wasn’t named, but it was like “That’s my tweet.” And then it was like a huge thing on – there was a three-part super long article on just Hipstamatic and their reaction to Instagram getting purchased. They recently laid everyone off, all of their engineers, designers, office manager - everyone except the founders, basically - and just the story behind all that. Anyway, I guess if you’re interested you can go read the article, it’s super long.

That was published recently, the Inc. post?

I think like a month ago, two months ago… Something like that. Anyway, so right after I left Hipstamatic, I decided to leave and didn’t really have a plan. I was just like “I’m leaving.”

Well, for those who weren’t following at the time - I know that some have listened to one and two - can you just roughly paint what month, what year was it that you left Hipstamatic?

April of this year, I think… 2012.

Okay, so this is still 2012 then, that you’ve done these… So Sam’s still catching up even.

Yeah, it all moves pretty quick.

It does move pretty quick.

Yeah, so in April I left Hipstamatic and didn’t really know what I was gonna do; I just kind of like sat down and home… And this was still when I had a bunch of stuff, and was like “Well, I guess I could work on Cheddar”, because I had done it like a year ago; I had started on it like a year ago and had a bunch of beta testers… [unintelligible 00:15:45.15] was one of them, which was pretty cool. He didn’t really use it, but he signed up.

Because markdown was in there, is that why?

No, markdown wasn’t added until right before I launched the second time.

I’m just throwing some jokes, but that’s good.

Well, sorry. [laughter] This is harder than when I’m in person. We should totally do one in person sometime, it would be fun.

Yeah.

Anyway, so I was like “You know what, I’ll work on Cheddar, because I already have it. I’ll knock it out in like a couple of weeks.” I had just used Stripe for the first time in another project and was completely blown away, so I was like “I’ll just put it up online, charge a couple bucks for it, and then go to the next thing”, thinking I can just do it, leave it, it will be sustainable and I could go to the next project. “I don’t know what that is yet, but whatever, I’m gonna do Cheddar and then go from there.”

It turns out it took three months to finish it, and in that time I sold all my stuff - we’ve kind of been through that. But anyway, at the time I was just like “Well, I just need to make something, it needs to make some money” and I’ve started on this and kind of know what I wanted to do, so that’s what I’m gonna do. It was just like a minute of me sitting on the couch in silence, like “Alright, done. That’s what I’m doing.” That’s kind of how I make decisions, I do things pretty quickly.

You seem a little whimsical when it comes to that. And I don’t know if whimsical is a really negative word to use in that instance, but it seems like – not so much that you change with the wind, but that it doesn’t take much to persuade you to go a direction.

I mean, I’ll kind of just objectively weigh the pros and cons of something, and then it’s just like “Okay, done.” I’m not like “Well, let me think about it for a couple of days.” It’s like “Okay.” I mean, right now I’m convinced that this is the right thing, so that’s what I’m gonna do. Occasionally, I’ll revisit a decision, but for most things I’m usually pretty like “Okay, this is fine. Done.” I don’t know.

So it’s April, you quit Hipstamatic, you started Nothing Magical, your first product was Cheddar, you hate to-do apps, you don’t have a ton of money to burn but you’re burning through it because you have a decent chunk go into your rent alone, and then other bootstrapping costs, like incorporating and lawyer fees and whatever else comes into play. We’ve heard quite a bit of that, but then you ran out of money. Was it a surprise? That’s my biggest question mark - was it really a surprise or were you expecting it and you were just kind of like dreading it?

Well, at first I was really stressed about it. I sold all my stuff, I took a couple contract jobs to supplement my income, and I was like, “Okay, I need to be as lean as possible.” Then I think a month or so in I was like, “Well, I guess I can go to Tahoe this weekend” or “I guess I can do this”, because I’m looking at my balance in my bank account and I’m like “Wow, I have so much money. This is great! This isn’t as much stress as I thought it was.” Then a couple more months later I was like, “Okay, this is a problem. I need to either do some contract work or find a job, but I’m definitely – I don’t have much time left.”

Right around that time I was thinking about investment and I started going on that route. Investors didn’t like that, because I was like “Yeah, I don’t wanna make any more productivity apps” and they’re like [unintelligible 00:19:28.10] because it’s usually older guys, you know? They’re like “Lightning doesn’t strike twice.” It’s very like older by the book, playing it safe… And it’s like, “Well, yes, but Cheddar was just more of like look, I can make something that makes money by myself really quickly.”

It was a test.

Yeah. Like, “Give me some money and I’ll make something for real. This is child’s play. It’s a to-do app. That’s the Hello World of any web framework.”

I think it was actually David Heinemeier Hansson, he was actually debating back in 2005 when he made the infamous whoops video, he was considering blog? to-do app? blog? to-do app?

Yeah. I mean…

You didn’t find that funny? That wasn’t funny to you? Alright…

Sorry.

I tried a joke and then there was no jokes there…

Sorry. [laughs] I’m terrible.

You’re being serious and I’m throwing a joke in there, so…

You’re trying to lighten it up, it’s good.

That’s two for me. Two no-jokes. I’ll just go ahead and stop.

You’ve got one more. You’ve got one more.

I’ll try it one more time. I’m just reinforcing the fact that the very first demonstration of Ruby on Rails was a blog or a to-do app, and I don’t really think David was on the fence blog/to-do app, but I thought that was a good joke.

Oh, I thought you were serious about it, like he was actually on the fence about it, like you had read something; I was like, “Oh, I hadn’t seen that. That’s… Okay.”

“That’s enlightening, I can’t believe it. That was so close.”

Yeah, I was like “I can see that, alright.” But if you look at Simperium or Meteor or any [unintelligible 00:21:07.09] all to-do apps are like the example app.

Right. Well, it’s because it’s user interaction, it’s creating a record, it’s the state of a record, it’s that user interaction back to the record of “Should it go away? Should I change the state of the record?” It’s a good example, I think.

It is.

It certainly shows that you have a good commanding skillset of writing stuff back and forth in a database and dealing with user interaction. I think you did Cheddar well; I think it was certainly what you tried to make it be, where “Hey, I can build this and make money at it, but give me money for real and I’ll make something for real.”

Yeah, I mean, what makes Cheddar good is not anything technical. Anyone can make a to-do list. It’s like all the other stuff - the design, and the interaction, the fact that there’s apps for everything. That’s more of what I was showing - the fact that it’s a to-do list doesn’t matter. That’s like a really tiny amount of the code; the rest is animations and design and all this other stuff.

Is there anything, considering the saturation – we talked about this in the past shows we’ve had you on… Is there anything about – because we’ve talked about how to-do apps are, it’s a pretty saturated market; you’ve got a number of known competitors, a number of known competitors that actually offer this stuff for free, some that really provide good value and have paid versions of them… Is there anything that in hindsight when you’re looking back at what you had done with Cheddar and what could be possible, is there anything you would have done differently with it? Because you obviously could have made money with it and you did make money with it, it just wasn’t – from what I understand it wasn’t a ton… Not enough, obviously, to keep you afloat, because you wouldn’t have made the changes you’ve made, but is there anything you would have done differently with Cheddar looking back on things, knowing what you know now?

I wouldn’t have done the API, I wouldn’t have done the Mac app, and I possibly would have switched from Backbone on the front-end on the website. Because doing the API took a ton of time… And I’m really proud of the documentation and all of that. A couple people made apps for it and there’s like an Alfred extension, but all of that – developer support there, there’s a lot of stuff, and if I ever wanna add something quickly, it’s impossible because I have to add really nice API support for it, not just something thrown together… Which has its pros and cons.

And then the Mac app as well - I’m not good at Mac development. I hired a 17-year-old to help me with it, and he did a really great job, but it was just like… You know, he’s back in high school now and it’s like…

He’s not around to help out.

Yeah, it’s just like this big distraction and it’s still – it’s in review within the App Store right now actually, but it’s just not even close to my standard of quality. I don’t know if I’ll actually release it.

So is that from a coding standpoint or from a “how it actually works” standpoint?

I mean, interactions, I guess; just making custom controls, custom interactions, and really nice animations and stuff on the Mac is just really challenging, compared to iOS.

Right.

If you wanna make a custom text field and password text field, it’s like two lines of code. But if you wanna do it on a Mac, it’s like hundreds, twice, because you have to do passwords all completely separate. It’s really terrible.

Anyway, I wish I wouldn’t have done it, because it was a big distraction. Better I had just done a WebView in a Mac app for now, and then maybe made a better one later. Personally, I don’t use the Mac app at all, because it’s terrible. The web app works so much better.

Well, your WebViews are really good; I never really understood why you’re trying to focus on the Mac app when it made more sense to focus on product and focus on anything that made money growth, you know?

Yeah. I should have absolutely worked on the team’s product and not the Mac app or the API, and moved quickly on those fronts to drive revenue sooner first. Because before, my strategy was like “I wanna make it the best possible experience on every platform”, and if I’m trying to make the best possible experience, a native Mac app is better than a WebView. I think that’s kind of a hands-down argument. But I didn’t realize how long that would take, I guess is my problem. Because if I had done all this in like a week, and I had a really great Mac app and a really great iOS app for iPhone and iPad, I had an API and a website that works everywhere, and an Android app that’s just wrap around the WebView, now I have this really great product and now if I can add teams on top of it, they kind of have no reason not to, because it’s like “Oh, it doesn’t support my thing” or “There’s not a native app…” It’s like, “Well, there is. There’s everything. There’s no excuse to not try it” was my thinking at the time. So it’s definitely flawed. I should have stayed focused and not spread myself too thin… Because I did all of it. It’s a lot for one person.

Let’s camp out on that exact phrase you just said, “staying focused”, because I’ve had the chance to be on a couple podcasts, you said you were on The East Wing recently, or not long ago… I think maybe even before you were – after you were on…? Was it – I think it was after part one, but before part two.

I think so, too.

I love Tim Smith, I love his show; I actually had a chance to go on there and talk about things I do. I couldn’t believe it, but he wanted to have me on that show as well. So on there, he asked me - and I get asked by a number of people, because I’ve done this show for a while and I’ve talked to some pretty cool people like you and others about your past, and get a chance to glean into the rights and the wrongs, your path, your bumps, and your bruises, and get a chance to learn from the things you’ve done right and the things you’ve done wrong… And the main question people wanna know - because everybody wants the TL;DR, they wanna know “What’s everything that you’ve learned from this show, Adam? Without me having to listen to 35+ shows” or whatever it is. And the thing that always rings to my mind is staying focused. So many people on this show have said “I wish I had just stayed focused.” So what does that mean, like, when you say that about this, “stay focused”, what would have been stay focused? Not so much the exact details; sure, if you wanna go into those, fine, but what does staying focused mean as it meant to success for Cheddar?

What made Cheddar great was the real-time syncing and the design, and the iPhone app and the web app worked really great together. That’s what made it great, and then I tried to do all this other stuff, and I should have just focused on the core product and made, you know – there’s a lot of things you can’t do that are really annoying; you can’t move a task between lists on the web. There’s a bunch of silly things; you can’t delete a task, you can’t see a task you’ve deleted or you archived… There’s just a bunch of stuff I really need to – core features that should be done that aren’t, because I spent all this time on other stuff.

If I had just focused on the product and made the core product better, and then expanded the teams, like was the original plan, I might have not had this opportunity. But whatever, it was a good experience and a very hard lesson in how valuable it is to stay focused.

Yeah, I’m really – I mean, I’m sad for you to have to learn that lesson; I mean, you’re young… Let’s not – if you’re listening to this and you’re bummed out because Sam’s got this bad life, don’t. Sam doesn’t have a bad life.

[laughs] I don’t, it’s great.

Sky’s the limit. You’ve got a full life ahead of you, Cheddar is not the end of you, it doesn’t define you, it’s not who you are… It’s a good lesson. I think one day in your life, you’re honestly gonna reflect back on maybe this moment in particular, but moments in and around what you’ve done… I mean, you had some major courage to do what you did. Not everybody would take $60,000 they have in a bank account and not - for a lack of better terms - burn it, like you have.

Yeah.

It doesn’t mean it’s gone forever… Sometimes – like, you hadn’t gone to school to learn what you know; it doesn’t mean that you didn’t spend the money that it takes to learn what you know.

Indeed. That’s pretty funny. That’s funny, I like that.

So I think in some way, shape or form, whether it’s the school of hard knocks, which is why it’s called that, or it’s actual university - either way, somehow, some way we all pay our dues. And it can be monetary, it can be through blood, sweat and tears, it could be bloody knuckles, punches in the face, whatever you wanna call it… I think this could have been your time, and it’s good.

Definitely.

So let’s talk a bit more about learning, because there’s yet one more sucker punch here. You pursued a co-founder, and that co-founder was a good friend of yours. Can you open that up for me?

Sure. Well, so I was getting low on money, talked to a bunch of investors, pitched them, and like “You know, I want you to make productivity”, and I was like “No, no, no, I wanna do other things.” They’re like “Well, I don’t know…” I was like “Well, I have a possible co-founder that’s also Rails/iOS, really great engineer.” They’re like “Oh, well talk to me when he’s in. That’s interesting.” They’re like, “Okay, now I’m interested.” And that happened with at least four different people I talked to. They were like friends, and had a lot of money, and would definitely invest if I had a right pitch for them. So I was like, “Okay, well, great.”

I had a friend I’d been talking to since I started, like “Hey, you should do this with me.” So my friend Kevin Smith (@kvnsmth on Twitter) super awesome guy, hired him at Hipstamatic a year ago (December), and one of my closest friends… Anyway, so he had just left Hipstamatic a couple months later. This is - gosh - summer, I don’t remember which month.

June?

I think so. Maybe July. June or July, I don’t remember exactly. Something like that. Yes. No, early August. No, late July, early August, something like that.

Early August.

Oh, hilarious! I’m looking at my calendar; Founders Talk, and then that same day, dinner with Kevin. Amazing.

No way, wow.

Yes. I think I even mentioned it on the part two, like I have a potential co-founder and I was excited about it. Maybe I didn’t mention it.

Yeah, I recall you mentioned something about a potential co-founder… I mean, obviously – those who are listening to Sam talk about this, you’re probably wondering “What’s the significance here?” There’s a lot of good documentation, blog posts, people talking in the startup world, especially in the tech startup scene where having a co-founder significantly increases your chance of getting funded, so obviously, Sam, you were bootstrapping to get funding… That’s part of your story here, so please continue.

Well, I mean, the goal originally wasn’t to get funding, because I thought I would be profitable. Then I realized I couldn’t be, and then if I could get funding - and not a ton; I was only looking for like 200k-500k, which sounds like a lot of money, but if you think about it, a low salary in San Francisco. That won’t last very long for two people, especially with other expenses.

So I had asked him way before, and he just found out he was having a kid, and he was like, “I just can’t. I need a stable thing right now.” I was like, “No, I understand.” And then I was like, “What if we get money? The two of us, we could definitely get money.” I still believe that whole-heartedly. If he had joined, we could absolutely go get the money we needed. And he was like thinking about it… Because he’s the opposite of me. He has to think about decisions a lot, which is a great balance, because I’m very impulsive. When we worked together at Hipstamatic, it was perfect.

So he’s like, “Okay, we’ll have lunch (it was Friday, or something) on Monday, or something.” I was like, “Okay, great.” And he turned me down. I had even overnighted business cards with his name on it, because I was so confident, and I was gonna surprise him at lunch. Then he said no, and I was like, “Oh, man… I’m completely screwed. I’m really sad I can’t work with my friend”, because I was getting lonely working alone in my apartment anyway, but… And we could have made some great stuff; there’s a bunch of great things that could have happened, but on the other end, it was like “Now I don’t know what I’m gonna do. Financially, I’m completely screwed right now.” Because that was my ticket out, to get money. Now I have nothing. I have to either go get contract work or get a job. Because Cheddar – it’s too late; I can’t make Cheddar this profitable in the time I have. I’d run out of money.

I was really depressed for a week at least. I just sat in my apartment and didn’t do anything for days. It was terrible. But hilariously enough, right after Kevin had said no at lunch, we walked South Park in San Francisco to get coffee or something (I don’t remember). And I ran into Aaron Gotwalt, who is now the CEO of Seesaw, and we talked for like not even a minute and he’s like “Yeah, we’ll get lunch sometime, whatever.” I gave him my card.

I had lunch with him the Monday after Kevin had said no, so I just sat alone in my apartment for a week, didn’t do anything. I got up the next day, ate lunch at like 10:30 on that Monday, because I was so bored and depressed… And I looked at my phone and I was like “Oh, I have lunch with Aaron today.” I had typed the text message to cancel, like “Forget it, I don’t wanna go. This is stupid.” I was like, “You know what, fine, I’ll go. I haven’t left the house in a bit…”

A bit…

Yeah, it was – I’d go to the corner store and get a frozen burrito and a Dr. Pepper and go back to my apartment. The guy was like, “Hey, how’s it going?” I was like, “Hey, yeah. I’m here again. Shut up.”

“Shut up, just give me the burrito.”

So while I was doing Nothing Magical - this is sad - I gained like 60 pounds; ridiculous. Or maybe like 40. It was a lot. I don’t remember how much it was exactly before, but… And being in San Francisco, it was not healthy, because I just stood alone in my apartment and worked, and I’d get a frozen burrito and a Dr. Pepper, because it was like really motivating. And a Red Bull occasionally. Yeah, super terrible.

Oh, man…

I just got a gym membership this week, now that I have moved, and I finally got my bike repaired… I was in a wreck, it was terrible. It was broken for a bit. Anyway, so now I’m like excited to get healthy.

I’d have to say it like this, Sam, it doesn’t sound like the last 6-8 months of your life have been very healthy for you.

Oh no, not at all. I ate terribly, and didn’t exercise, because I had no commute… Yeah, it was not good health-wise.

Right.

But I now have insurance. I didn’t have insurance at all during Nothing Magical, but as of 1st December I have insurance, which is great.

Do you get sick often?

No, actually I haven’t been to the doctor since I was in high school, which is probably a problem, so I’m gonna go to the doctor and get a check-up. I haven’t been to the dentist in a long time… You know, it’s just stuff you do when you have a real job, that I just haven’t done.

You know, there’s a lot of people that – this wasn’t exactly a topic I wanted to veer off on, but there’s a lot of people that look at, I guess, maybe people you and I, that we’ll take risks like that, like start your own company, go a couple years without having insurance, or not have a 401k or the security - and sometimes false security - of a full-time job and think we’re crazy.

There’s pros and cons on both sides of the fence, honestly… It’s not like one is much better than the other, but maybe you’re like me - and I imagine you are - where I can’t be happy unless I take at least some of that risk and figure it out, because if not, I’m always gonna be sitting there with some level of regret… Like, “Could I have done it? What if I did do it?”

Yeah, I was thinking – you were saying about all the risk and stuff, and it’s like, I didn’t really worry about it, but no, I think you’re right, if I had had… So we talked last time, I turned down GitHub, which was really hard. I think if I worked at GitHub this time – because that was right before the Cheddar launch. It was like a couple weeks before I launched, so I wasn’t even done yet… And that was like part of the way they were really interested in me, because they saw it and were really impressed (the beta) and like, through other friends. But if I had been working at GitHub this whole time, I would definitely be like “What if Cheddar had done really great and I was living off of it?”

Now I know that I still suck at running a company, but I learned that, again – because before I’ve lived on my own, sold my own software, and ran out of money and got a real job. So this has happened before. But anyway, I guess it’s good to learn again. I have things to do better next time.

Well, if you keep doing this - the definition of insanity is to keep doing the same thing, expecting a different result, just so you know… I’m not calling you insane, I’m just saying – that’s all I’m saying right there.

No, it’s good. I’ve done contract work full-time before twice, three times now, and every time I completely hated it. I was always telling my friends, if I ever decide I’m gonna do contract again, tell me I’m stupid; I’m not gonna listen to you, but tell me I’m stupid, just so later I’ll know extra that I’m being stupid. So it was like, “Okay, I’m not gonna do contract work.” When I run out of money, I’m just not gonna do it; I’m gonna hate it… It will pay really well, but I just don’t care. I will hate life. I’d rather get a job than do contract work. Because honestly, if I did that, I wouldn’t have time for Cheddar.

If I take an hour and watch TV, it’s like “Well, I’ve just lost a couple hundred dollars”, or however much my rate is at the time. I don’t know, it’s just hard to enjoy anything, because everything’s hourly. I don’t know, it really messes with my head.

Yeah, I feel you. I wanna talk about GitHub, but only after we talk about this quick thing here… So you know I host a different show called The Industry Radio Show with Jerod and Drew [unintelligible 00:41:06.27]

Excellent.

Thank you. And we recently had Chuck Longanecker on this show, who’s famous for Hello Bar, and he runs Digital Telepathy, which is an awesome agency actually in your previous neck of the woods… And one thing we talked about on that show - I’ll link to that in the show notes by the way, so if you’re listening to this, we talked about following your bliss, your genius; we talked about that on that show… And you say with this tone like “I hate contracting work” - well, I think it’s because it is not your bliss. And just because you aren’t able to do something that was uber-successful financially with Nothing Magical (and even Cheddar, if we’re gonna go down to the product level), I don’t think that you were not following your bliss though, right? Because you said – and that’s where I think we can kind of play this into the conversation around GitHub and what that’s gonna lead into…

But they saw something in you and a desire to hire you because you were following your bliss, you were creating something, so I think you’re definitely a creator, and it depends on how you gauge and measure success, whether or not from a startup perspective Nothing Magical and Cheddar may in some eyes be a failure. But in some eyes it may also be a success, if you’re measuring it based on what you put out and how much you put out. Right, lines per code, LOC, that might be a huge success, if you were measuring it based on that; or happiness level for you with what you were creating. It depends on what you’re measuring, you know what I mean?

Yeah, I mean, the three months of me making it and the next month or so after were some of the best times of my life as far as like – you know, people would ask me [unintelligible 00:43:04.22] I work for myself, I really like it. Or they even heard your show and are like “How did you turn down GitHub?” It’s like, “No, I completely love what I do. I would never do anything else”, which is funny that I’m doing something else now.

It was a really great experience, and I’m glad I did it. Obviously, GitHub would have paid a lot more than my zero dollar salary, and I’d be with some of the smartest people in the world; I completely love GitHub, and I’m really glad I tried and kind of failed. It was absolutely worth the experience.

Yeah, I’d say you can say you failed, kind of, in like parentheses, or something like that, you know?

Well, Cheddar still makes money. Not a lot, but…

It’s not enough.

I mean, it more than breaks even, so… There’s a terrible bug right now. If you subscribe in iOS via in-app purchase, they’re not auto-renewing subscriptions due to like a really stupid App Store restriction… So I have to expire your account - if you buy three months - of three months and then be like “Hey, you need to buy another three-month credit, or you can pay with Stripe and it will auto-renew.” But right now it doesn’t check, so everyone that’s paid in iOS - I probably shouldn’t be saying this - has it free for life until I fix this. So I’m losing out on a bunch of money, but I just haven’t had time to work on it. And also, I need to “Hey everyone, this is what happened. I’ll give you two more free weeks, and then you have to pay.” I have to explain and be nice about it, instead of just turn everyone’s account off and be like “Now you have to pay me.”

I could do teams in like a week if I were to just sit down and do it. I just need to make time and do it. I don’t know. It’s really pathetic that I can’t even make time to charge for my product, but whatever. Here we are.

Well, people won’t hold that against you. So let’s talk about GitHub, and then we’ve got a couple other topics we’ll talk about as well. I believe we talked about GitHub in part one, if I’m not wrong. If not, definitely in part two; I know we’ve talked about it on this show before, so for those who are listening for the third time with Sam’s story, you know that Sam was offered a job at GitHub and he took it, and then took it right back. It was like a two-week period where you were hired at GitHub, and they were even preparing for you to come - not come there, but be a part of the team, because everyone there is pretty much distributed. They do have an office, but you don’t have to work at the office is what I’m trying to say. But you turned them down… The biggest question I think I have here is really – because you’ve been honest with everything else, I really wanna know if you’re really bummed out for saying no, and if you really have some extreme regret about not going there. Because like you had said, decent salary, some of the most smartest and brightest people in our programming industry today work there, from all walks of life. Everything from .NET to Ruby on Rails, to Git… All the really smart people work at GitHub. Not all of them, let me just say that… A lot of them. Because I don’t work there and I’m smart, so… [laughs]

That’s right… Hilarious. There’s definitely some regret. I mean, it’s the biggest offer salary-wise I’ve ever gotten. Money doesn’t really motivate me, but on the other hand, having a lot of it isn’t a bad problem. The thing I regret the most I think is not having the chance to work with their team. I would have been like 80-something or 90-something, and right now they’re like 140, or something. They’ve been growing like crazy.

So it’s a really pivotal time for them, and I think it would be really cool to be there and experience that, even if I wasn’t gonna stick around. But you know, they were like “We don’t want you to be here just for a couple months, we want you to be here for a long time.” I was like, “No, I know.” Then, when I was quitting that, when I emailed Chris, the CEO – it was only a couple days by the way; it wasn’t like…

Oh, I thought it was a couple weeks, sorry.

No, it was a couple days. It might have been like two or something. Maybe it was a week, I don’t remember. Anyway. [laughter] Anyway, I think it was definitely in part one, if that matters at all.

Yeah, go back to part one and listen. I’m pretty sure it was part one.

Yeah, because that was before Cheddar came out, and then part two was all after Cheddar came out. So the part two secret was with the Wunderlist thing.

Right, right.

Anyway. I was like, “You know what, I would love to work at GitHub. I have immense respect for you, your offer is really generous.” But it was like “You know what, I think I’d be really mad at myself if I never gave Cheddar a chance, and I’d probably just quit in a couple months and go try it. Because I’ve always wanted to do my own thing, and now I finally get to do it, and I feel like I’m quitting before I even start.” That’s when I wrote that blog post Staying Strong. It’s like you know what, I really need to just focus and do my own thing right now, instead of – because like “Well, you can still work on it if you work here”, and it’s like “I know, but it wouldn’t be the same.” I don’t know, I’m really glad that I turned them down and I had the experience, but on the other hand when I was running out of money that would have been nice. But I don’t know, the predicament I’m in being like “I ran out of money”, it was like “You know, this is a good experience too, and I’m excited to learn from it.” I don’t know, I guess the definitive answer would be “I don’t wish I worked at GitHub today.” Not that I – I’d love to work at GitHub and they’re amazing, but today I don’t wanna work at GitHub, and I can say that consistently, since I’ve turned it down.

Well, there you go.

So there it is.

I think you’re quick to make decisions, but it’s also important to make decisions and be firm and believe in the decision you made, because if you always second-guess yourself, you’re always sitting on quicksand, right? And it’s just not a good thing for your brain to be doing things like that.

Yeah.

So I guess we’ve kind of come to the point where we’re talking about – I guess roundabout the overarching theme we’ve been kind of talking about is a bit of failure, a bit of learning, and ultimately now leaving indie development, because you’ve… Like, we started this show by saying you’ve got a lot of fans, and a lot of the fans really are rooting for you because they really – I think a lot of people really appreciate indie developers, and you’ve been this indie developer for a while and they wanted to see you succeed, but you’re leaving indie development and you’re taking on a full-time (yes, you heard it right) job.

Yeah, it was really sad… I didn’t announce it until November, but I really started in August. I was just like ashamed to even have a job, and also kind of afraid that people would freak out that I’m not working on Cheddar full-time… But they probably figured it out, since I kind of quit saying anything.

David Smith (@_davidsmith on Twitter) was really encouraging me to do indie development, and I was like “Well, I had an offer from GitHub” and he’s like “Okay…” I could tell he was pretty disappointed. And thinking back to that conversation a couple days later is when I was like “You know what, I am gonna do my own thing.” That was one of the things that put me over the edge. And thinking when I was accepting the Seesaw offer, before I was signing the paper, I was like “You know what? David is gonna be disappointed.” And not that I’m even super close friends with David, but I was just like “Everyone in general, I feel like I’m letting them down for failing with Nothing Magical’, but whatever… I have 100 T-shirts in my closet, so yeah.

Well, you’ve said the name Seesaw, but let’s give a proper introduction of exactly, I guess, for a lack of better terms – do you even know what it is?

I know what it is, you don’t.

Okay, so you know, we don’t. But you can’t tell us the details, because it’s not allowed.

Unfortunately, I can’t say more currently. We have a Haiku on our homepage; it’s like “Make decisions fast, with the help of trusted friends. When in doubt, Seesaw.” Oh, I think we have an About page. There’s a little bit of stuff. I mean, it doesn’t really say anything; you still won’t know what it is… But anyway, I’m working on it, I’m employee number one. We’re an app to help people make decisions, I guess that’s all I can really say. It will hopefully be out early next year. I can’t really say. I feel so cool to have secrets, I don’t know.

Yeah. I love secrets.

I can remember turning down Apple at one point, just to like “I can’t tell you what we work on.” But I would have worked on new maps, so I’m glad I turned that job down, because people would hate me. Anyway…

You wouldn’t have a job.

I’d be fired. Tim Cook would just – done. Anyway, so I don’t know if you heard of CoTweet… Are you familiar with that?

Yeah, absolutely. So I guess if you don’t know - for the audience - CoTweet was this product around Twitter, to help enterprise companies share a Twitter account, so like @coke or like Ford, or Starbucks, or whatever, all these brands have a bunch of Twitters, and they can sit there and they can all share the account. Twitter really loved them, they were really successful, and they sold a couple years ago; two years ago I think, a year and a half, whatever. They sold and did really well.

Now they’re starting again, it’s the three founders of CoTweet, and I’d met them through Kevin, the co-founder that turned me down. And I was really excited from them telling me about the product, and the fact that they’d been successful in the past, and we raised our funding really quickly; I don’t know if I’m allowed to say, but… Surprisingly fast. So I was like, “Wow, these really know what they’re doing”, and I was just really excited to work with people again, and to get out of my apartment and go to the office, which is funny, because now I don’t work at the office anymore. But yeah, it’s just really exciting to be with a team, making something again, versus just by myself making every decision.

So when you say “working with a team”, what’s a typical day like?

Sure. Well, I guess I’ll – currently, we have five people, including myself. There’s the designer co-founder, the engineering co-founder (which is also the CEO, which I think is pretty cool; and our business guy). Normally, I’m not a big fan of business guys, but he’s really awesome and super valuable, so that’s good.

Anyway, then myself, so I’m employee number one, and my title is VP of Engineering, which sounds super cool and impressive to [unintelligible 00:55:07.09] people in Louisville, but it’s a five-person company, so it’s not really – I mean, it’s a pretty relative term… Like, “I’m the president of my own little apartment”, you know? It’s silly. Anyway. Then we have one other Rails engineer… Which is really cool. I signed the papers to hire him. I’ve never done that before. I mean, I hired a ton of people at Hipstamatic and other places, but not like – you know, I recruited them, but didn’t like get to sign the paper. But it was cool, like “Yeah, I’m hiring your right now.” It was fun.

Anyway, we work with Campfire a bunch. So we usually just like get on Campfire and see what’s going on. And we have a rough bullet list in Basecamp of like “Here’s what we need to do”, and I’ll kind of like just go through and like “Okay, well I’m gonna work on these things” and then I put those things in my Cheddar list, which is silly of me…

I actually just recently - two weeks or so - started using Cheddar. I hadn’t used it since Kevin said no, pretty much. I was just like, “Ugh…” That was a terrible couple weeks before I started at Seesaw. And then when I started at Seesaw I was like, “Well, I’m working on this all the time. I don’t really have time to even open or look at Cheddar”, so… Anyway, but I’ve been working with Cheddar, which is nice. And I’ll just kind of go through and work on – I work on an iOS product as well as the web, so I guess we have an iOS app… That’s new information. I don’t know if I’m allowed to say that, but whatever. I mean, you can figure that out, as I am a primarily an iOS engineer and I work there.

We can probably guess, yeah.

So I kind of go back and forth with the designer on – he’s @kyle, isn’t that epic? That’s such a great Twitter name, @kyle. Anyway, he’s our designer. We work on iOS, or mobile web or other stuff. I’ll kind of hop back and forth between Rails, but not a ton. I’m trying to stay focused on iOS right now. I was hired to lead all the engineering, but at this point, since our CEO and our other engineering hire can do Rails, they stay pretty focused on that and I stay pretty focused on iOS for now, which is nice.

We usually just talk in Campfire all day, and get stuff done, and we send out builds through TestFlight almost daily, or multiple times a day, it depends.

So if you’re on TestFlight, that means you’re probably at least having a beta audience; is that just yourselves, or…?

Currently, it’s just the company and our investors, and like wives and stuff. It’s not very big. We have a big list of beta people we’re gonna launch to soonish, which is full, so no ask, sorry. I mean, obviously, Adam Stacoviak can have it, but… We only get 100 slots from Apple, so… Sorry, I’m just the messenger.

I wouldn’t mind trying it out, yeah.

Yeah, I’ll hook you up. Yeah, I mean, I’m in San Francisco a week a month; next week is my week in San Francisco for December… And it’s good to kind of be back and see – I mean, this is the first time I’ve been back since moving, but I’m excited to get back and see friends, and eat at my favorite restaurants and just be in San Francisco, go to events… It’ll be good.

So I’m kind of glad that I had the opportunity to travel a lot… I mean, a decent amount, I guess. It’s one of the things I’ll definitely miss - it’s going on in Louisville as well, but… Yeah, it’s a pretty good setup. I’m really happy with it.

Alright, so we’re at a point where we can probably talk about I guess something a bit more current. If you’ve listened to part one of Sam’s conversation with me here on Founders Talk, we talked about something a bit more personal for you, Sam… We talked of something personal here where you were turned down, but this was a co-founder, but in part one you were turned down as well, and it was something a bit more personal than the co-founder… It was an actual potential marriage.

Yup.

But now you’re engaged, and it’s a funny story.

It is. It’s pretty funny… When we were shopping for the ring, it was like “So, have you been engaged before?” It was kind of like a huge joke, and it was like, “Um, yup.” It was like, “Oh”, and it was really awkward for a minute, it was kind of fun.

So yeah, I was recently in Louisville - gosh… October, I think? Yes, October. Maybe September; I don’t know, whatever. No, it was definitely September. Whatever, it doesn’t matter. Recently… Helping my mom; she was moving back temporarily from Louisiana. I grew up in Louisville. Anyway, I happened to run into Ellen at Starbucks; Ellen is my now fiancée. We talked for a bit, and then I went home and didn’t really think about it.

Then we were talking again a little while later, and we had sort of dated right after I wasn’t engaged, when I was like 19 or something. It was silly, because I was in Oklahoma and she was in Louisville, and it was like – this was like once or twice, but it’s like “Well, this is never gonna work”, and none of us had plans to move… She was in school, and I still had my first real job.

So this time around we’re like “This is really cool” and “I’d be willing to move to Louisville just to see if this is something worth doing, and whatever. So we talked a lot, and she’d kind of visit and whatever. And then I was in Louisville to visit - I was only there for a week - and we were talking about it a lot… And we had kind of talked about it even before, one of our very first conversations, and it’s like “You know what? We should get married.” Like, “Yes, absolutely.” We both felt completely the same way from the very beginning this time around.

So two weeks after really starting to even like talk to each other again for the first time in a while, besides just like at holidays and stuff, we got engaged, so… Pretty crazy. My best friend from high school - his now wife’s little sister is Ellen. So I’d hang out with them with my friend at their house occasionally, and that’s how we met. So I don’t know… Pretty crazy.

It’s always funny, like “How long have you been dating?” I’m like “Well, like two weeks…” “Oh, well…” People instantly judge me, but it’s like, whatever, I don’t care.

Well, that’s good. I don’t think I’m the first one, but I’ll be one of the first of many to say “Congratulations!” That’s a beautiful thing, man.

Thank you so much. I honestly couldn’t be happier. It’s spectacular.

I think it awesome that you’re back in this place, and you’re heading back to what I think could be a happier and more healthier lifestyle. I can personally tell you having a good woman in your life makes all the difference. Because when you’re a lonely bachelor and all you do is work on Cheddar - or whatever your Cheddar might be for you - you can, like you said, gain 40 pounds, go and eat a frozen burrito and a Dr. Pepper and that’s okay; we make that okay, but women, they’re like “That’s not okay. That is NOT okay…”

[laughs] I’m having dinner tonight, and a frozen burrito and a Dr. Pepper sounds like pretty spectacular right now. But we’re actually cooking dinner together after the call, so it’s definitely a big contrast, but it’s great, for sure.

So let’s talk about this – not so much the moving piece of it, but you went through this phase where you sold everything, and then you went and you rebought it all. And you talked about how that was kind of refreshing in some capacity, because it’s like getting to do it all new again, but I’m not sure if I agree, because I don’t know if I would wanna have all the stuff I have now, which I’m not really that fond-fond of my stuff; there’s a few things that I really hang on to, which is a huge downer for me, but ultimately I’m not really attached to my stuff that deeply… But I wouldn’t wanna go and sell it all, and then go and rebuy it all again.

[laughs] Well, financially it’s pretty stupid, but I had a really big deposit from my really expensive in San Francisco, so when I moved to my cheaper apartment and I got a big check back, I was like “Okay…” And my first day I biked to where we were working; at the time, we were working in The Mission in San Francisco, which is like a 15-20 minute bike ride from my house… Closer to 15, I guess. And San Francisco is hilly; it’s not super hilly that route, but you know, whatever. I biked to the office, whatever, biked home for the first time… I got to my apartment and I was like, “Well, all I have is my desk and my bed. I need a couch.” I immediately understood why I had a couch before - because I had a job when I had a couch before, and I’d come home and like sit on the couch. And now it’s like, “Well, I just biked home, I’m tired and I don’t wanna sleep and I don’t wanna work… I need something else.” So I was like, “Okay”, and instantly right then I was like, “I’m getting stuff.” So I was like, “Okay, I’m gonna go get a TV, and I’m gonna go get stuff again.” Kind of funny.

So what were the first five items of stuff that you went and got? A couch was number one…

I bought a couch, yeah. I actually have a Pinterest board – I don’t really use Pinterest that much, but I usually have like a wish list and I’m cataloging things I have. It’s kind of weird. I’m sure it’s like “Please come rob me”, but whatever.

I bought a couch, and a TV. My TV stand from my last apartment – well, I was actually using like an end table before or something, but it was one of the things I couldn’t sell, so I just kept it… So I already had a TV stand, which was nice. When I bought my TV, I got an Xbox at the same time, which was probably one of my worst purchases the second time around, because I haven’t really played it at all; I don’t really have time, but whatever.

I think that’s it, big things-wise. I mean, I still don’t have a lot of stuff, I just pretty much have a couch and a TV, and that’s – oh, and I bought a bed, too… This is the dumbest thing I did. I sold my bed right before I moved, like weeks before I moved to my new apartment in San Francisco, which I was only at that apartment like a couple months, before I moved here… Which by the way, if you need an apartment in San Francisco, I know a place, and it would help me out a lot.

Anyway, I sold my bed right before I moved, and then I got in the new place and I was like “Well…” – because I kept my mattress, I just sold the bed, which was great, because the last of it… It was really minimal, like mattress on the floor and my desk - that was all I had… Which was awesome when I was in that mindset. That’s when I was really freaking out when Kevin said no, and I sold my bed, because I was like “I need more money.” I made $200 on my bed, which was terrible. So then I ended up buying literally the same model of bed, virtually identical. I mean, it’s not this exact same one, but it’s the same bed. So I was like, “Well, that was stupid. There goes a couple hundred dollars.” I guess that’s it, I don’t know.

But then I kind of went nuts, and then I bought a Sonos system - I forgot about this - which by the way, Sonos is awesome, and I’m completely in love with it. But I had like a speaker in my bedroom, and my kitchen, and then I even mounted one in my bedroom, so I could listen to the music in my shower… And one plays my home theater speakers. So everywhere in my apartment I had the same music playing, it was all in sync.

I went a little overboard, because I got the first paycheck and I was like, “Okay, whatever…” And then I got my second paycheck and I was like “Whoa, more money got into my account! This is crazy! It keeps coming!” The first time I was like, “How did I get all this money?” I was like, “There’s gotta be a mistake somewhere”, because I was used to just seeing my balance slowly going down, you know? And then it went up once, and I was like “Whoa, this is awesome!” so then I went a little overboard. Sonos is probably the most excessive thing I have, but…

I was wondering what it was, because I went to your Pinterest board, and this is kind of a neat usage of it, but my first thought is “Do you own all the things in this list?” Percentage-wise…

So for this apartment – pinterest.com/soffes/apartment; surely you’ll link it. Yes, all of this is in my apartment.

Everything, all this stuff?

Yes, yes.

I didn’t expect all this stuff to be in your apartment, but I was thinking like “You don’t need all this stuff”, but I guess maybe…

I mean, there’s not a lot – actually, the fan got thrown away in the move, but… There’s a couple things - most of it is all the computer stuff, and then speakers and kitchen appliances. There’s actually not that much if you thought about placing it in cabinets and stuff, or whatever. My apartment is still pretty sparse. Because before it was sparse – before I sold all my stuff, I still didn’t have a lot of stuff. I mean, I don’t know.

It’s interesting, and my fiancée kind of makes fun of me for this, she’s like “You only have really nice stuff.” It’s like, “Well, yeah, I guess you’re right.” And I’m thinking about it, I was like “Okay, I need to buy a toaster.” I mean, a toaster is kind of a bad example, but we’ll say a toaster… Like, “I need to buy a toaster.” Well, if I wanna spend $20 on a toaster or like $60 on a toaster – I mean, I’m not gonna buy a toaster anytime soon, which is probably far from the truth, but… It’s like, “Well, I might as well get a nice toaster, because there’s no reason to not enjoy making toast every day.” And actually I never eat breakfast or make toasts, so the toaster is probably a really stupid thing, but like… I don’t know. I have a really nice receiver, and I have like really nice speakers, and I really like music, so that makes me a little happy. I don’t know. With some things I don’t care, like the toaster, for example. I don’t have a super nice toaster, I just got one that looked cool. But I don’t know, for some things it’s like “If I’m gonna buy it, I might as well get the best one.” If I have the means to do it, then that will be great. I don’t know.

The toaster is funny because I didn’t even think that was a toaster, and for those who are listening, I’ll share this link in the show notes so you can certainly follow along with what we’re talking about here… But it’s pretty funny to me because this is total guys’ stuff. I do find it funny that you’ve actually put handwash on the list, but I guess you’re just being thorough.

Oh yeah, I mean… I went through and did like almost everything. This is like a pretty accurate representation of all my stuff. The coffeemaker and the grinder were a surprise for when Ellen came to visit. She likes coffee, and I don’t like coffee at all, but I got a coffeemaker.

Can we tally up how much you think roughly this is all retail?

Oh, gosh…

I would say $25,000.

Oh, you think? I was thinking like five would be a lot.

Really?

Let’s, like–

Well, a Thunderbolt display is $1,000.

Oh, that’s true…

That speaker alone is almost a grand, so you’ve gotta have two of those. That’s 3k so far.

So the monitors are, yeah, $800 for the pair. The nice speakers are like $800 for a pair, or a thousand for a pair…

And I own Sonos, so I know that that’s not cheap, but it’s not expensive either.

It’s like $1,200 I think in Sonos, or $1,600…

Okay, so I’m gonna change my number to $15,000, because you’ve got a tube amplifier…

That’s like $100, $200.

Oh, really? I was expecting more than that. I was expecting like $1,000.

That’s like $400. The record player is like $300. I don’t know, I think it can all be definitely under 10k, for sure.

Okay, 10k. Let’s say 10k. I’ll give you 10k.

But that was like my deposit in my last apartment. Like I said, really expensive. So I was like, “You know what, I have this check from my last apartment, so I’m just gonna make this apartment great.” So that’s what I did.

Yeah, I can see that. I like your style. You’ve got a coffee grinder and everything, you don’t mess around.

She doesn’t like the red appliances, which is… My coffee grinder and my toaster are matching, and they’re both red.

Yeah, I’m with her. I think Ellen’s smart. I think the red appliances –

You don’t like the red ones?

Neah…

Oh, they’re awesome.

I guess if you’re living in San Francisco maybe, but in Louisville I just can’t imagine that that’s hot.

Well, in my super modern apartment everything was all white, and then like fake hardwood floors, and the red toaster looked awesome.

That’s super modern.

It was really cool in my first super modern San Francisco apartment… But definitely in the more traditional Kentucky apartment it definitely looks silly, I’ll agree… But anyway.

You know, if anybody’s bored about this conversation we just had about stuff, for a lack of better terms, I think it’s just… It’s an exercise, and you said this best, actually, in your reverse minimalism post, where it’s an exercise of extreme minimalism flip flop. It’s a rewind. When you first started Nothing Magical, you left Hipstamatic, you were like “Let me get rid of all my stuff because I have a really expensive apartment” and you sold all your stuff.

Then not much long later, you went and pretty much repurchased all the things that you had before. I think it’s just kind of funny, the hand that life has dealt you sometimes. I just think it’s funny. You got home one day after riding your bike and you’re like “I’ve got a bike, I’ve got a desk, so “I need a big couch!” Just the way your mind works makes me laugh, so…

Well, I’m hot and I’m sweaty, and I don’t wanna go to bed and I don’t wanna sit at my desk, because I’ve been working all day. The logical thing is like “Alright, I need a couch”, and I went and got one the next day, so…

So let’s round off then, let’s talk about the future. We know that – does the future have anything to do with Nothing Magical, anything Cheddar? Are you done with it? What’s going on there?

No, so Cheddar [unintelligible 01:14:55.10] and I attempted to just like…

Pull it?

I mean, so in the App Store, if you make a name, you make an app with a name, then you have X number of months to use it, and then they’ll send you an email like “You have 30 days to use this name, or we’re gonna take it away from you and you’ll never have it again.” So I was like, “Well, I should submit something, because I don’t want Cheddar to go away in the Mac App Store.” So I think I’ll probably still release it, maybe I won’t, I don’t know. But I’ll definitely open source it. That was the plan from the beginning, to open source it once it came out. So right now it’s private. I’ll probably keep doing Cheddar; that’s kind of the plan. Because I’ve toyed with the idea of just like, it’s all open source, it’s all free, donation where like “Please pay me so I can pay my Heroku bill”, and if it gets to the point where it’s costing me a lot of money to pay Heroku, I’m just gonna turn it off, and you can hustle it yourself if you want or do whatever, I don’t care.

That was the plan for a little bit, and the more I thought about it, the more it made me sad because I worked so hard on it and I wanted it to be good. And it can make money, it’s just like, all the startups that just wanna get a bunch of users and all this stuff, it’s like “Just don’t be lazy.” It’s not the most difficult thing in the world to monetize your product. Just take your time and do it. It’s just me being lazy. Cheddar can make money and it can more than support itself if I just spent the time on it. I just need to make the time for it and do it. I think Cheddar will be around – so it’s not going anywhere anytime soon.

If somebody were out there now - and somebody was out there at one point in time - desiring to either buy it or buy you, or whatever… So if you got an offer from somebody to buy Cheddar, would you sell it?

Oh yeah, absolutely. Hands down. Like, it’s past the point where I enjoy working on it, it’s more of like I’m maintaining it because all my users were so nice to support me, it would be completely selfish for me to just take their money and not give anything back to them. I definitely plan on supporting Cheddar and making sure it doesn’t break. I definitely have some features I wanna add, just because – this doesn’t feel done to me. It’s like a song I’ve been writing that I never finished and can’t show anyone, because it’s just not finished. It’s that kind of feeling.

So a part of me just wants to finish it just to like finish it for myself, but on the other hand, if someone wants to buy it from me, I would be ecstatic to just sell it to them for not a lot, and move on. Down payment on a house, or something. Because Wunderlist offered me money for it, and it was like “Well, you’re gonna have to work here” and I was like “Well, I don’t wanna work here.” That was kind of like the thing. But they didn’t offer nearly as much as I wanted, and I think given the same offer now, [unintelligible 01:18:03.05] I would be a lot more like “Yeah, okay. Sure, let’s do it.” Because the whole point of it wasn’t to make a great to-do app, it was just to show that I can make something and make a great product, and I feel like I’ve proved that I can make something, and I feel like it’s a good product for the amount of time I’ve spent on it. I mean, it can be better, and the perfectionist in me - it’s never finished, I’ll work on it for the rest of my life… But realistically, I would enjoy my side-project time spent – I would enjoy my time more spent on other things. I’d rather be hyper-productive on a different project than take hours just to do something silly in Cheddar because I’m just not motivated.

Yeah. So I can imagine that at least a small portion of your users listen to this show, at least a couple, at least a small handful, so if you had a chance to speak directly to them in this scenario and thank them or say anything to them about their support of you, what would you say?

I mean, first I need to thank you, because a bunch of people found Cheddar from Founders Talk, so thanks again for having me; this was great. But to the Cheddar users that either came from Founders Talk or just are listening, I mean, you made that five months of my life when I did nothing but Cheddar as much as humanly possible, you made that the best time of my life, because without people using it, it was just like me sitting in a room, typing, for no reason. It was exciting getting up and seeing all my replies on Twitter; people were really excited about it, and support emails, and people were just like – I’d get emails just like “Hey, I think it’s really great what you’re doing. Keep it up!” It’s like, “Yes, this is awesome!” I was so fired up every day to work on it, so thank you for your support. Even if you’re not paying, thank you just for downloading it and checking it out. I appreciate you very much.

And then I guess on to the true future, and the way we normally close this show is the horizon question - what’s on the horizon for you, Sam, that no one knows about? Or maybe a few. Something super secret that you can tell us about. We obviously know you’ve got a [unintelligible 01:20:40.27] going on with Seesaw, so we won’t bug you about that, but anything else?

I’m trying to see – I’m scanning my post quickly… Yes, okay. Well, I mentioned it – whatever, I’ll be more direct. We’re getting married in September, which is very exciting and a little scary. Not scary – I’m like totally “Yes, I’m marrying this girl and it’s gonna be spectacular.” But planning a wedding is really hard. I don’t know if you’ve – I mean, I know we were talking about it before the show, that you planned a wedding and it was hard.

Actually, I didn’t plan the wedding. My wife planned the wedding. I participated… [laughs]

There you go. Well, I’m trying to contribute a lot, and it’s a stressful time. But anyway, after September - and our wedding will be spectacular - we’re most likely moving back to San Francisco, which is pretty exciting. That’s not 100%, but it’s very certain. That’s really exciting; I’m excited to be back in San Francisco with my new wife, and it’ll be great.

I’ve only been at Seesaw for a bit. I plan on staying until we sell, or something crazy happens, I don’t know.

That’s like a whole conversation on its own, that phrase you’ve just said…

Which one?

“I’ll only be there for a bit, or until we sell.”

No, I mean, I plan on being there until it’s done.

Okay, so I misheard you. I was like, “So you don’t plan to be there that long, or until you sell… That doesn’t sound like you’re really excited about your product.”

No, it’s great. I plan to be there a minimum of two years, which is a really long time for me.

Yeah.

I mean, being employee number one and having complete control over all the technology and technical hires and a lot of things - it’s really great. I really like it a lot and I’m excited to be around, and hopefully… You know, before I’ve had stock in startups and it’s never ever been remotely valuable, and I have a bit in Seesaw and I am very confident it will be worth something in the not too distant future. That’s pretty exciting.

Those are definitely hopeful words from you, for sure. On that front, in terms of two years down the road, and the future, and the fact that you’re employee number one, you’re building the team, you’re managing the team, I think that what’s – if you ask me, at least, I would say that what you thought was possible through Nothing Magical and Cheddar in the fact of somebody else believing in you that you could, I think this is a very big chance for you to prove that, because you’re at the center of a previously successful team of people who built CoTweet, and we both know that they were able to walk away from that deal with a decent amount of money in their pockets and a lot of learning under their belts… So you get to work with some previously successful people, helping them build their team and be a part of their product development. If you’re able to accomplish that goal, I can imagine the next adventure, if it’s not always this adventure for you, could be that much brighter, because I don’t think you failed at Nothing Magical; I think it kind of got you to where you wanted to go. It may not have been the exact outcome you wanted, but I think some of the results are probably similar to what you desired.

Yeah, I mean… Like I was saying before, I’m really happy with Nothing Magical, and it’s not going anywhere. I’m keeping the corporation and Cheddar, like I was saying. I can definitely see going back to Nothing Magical full-time after we sell or something, or whatever. Or maybe it’s a different incarnation with other founders, or whatever. My time as an independent developer or a founder is definitely not over.

For now, I’m happy having a stable job to support my future wife, and being in a small company - because I’ve never been in a company this small - there’s a lot of new experiences, and I’m really excited to learn. I don’t know, I think it’s a good next chapter for me, growing up a little, so…

Next chapter, yeah. Well, Sam, let me be the first to say it, I’m excited for you; I wish [unintelligible 01:25:48.06] blessing upon you to you and your wife and your future. I know that you’re a wise young fellow, that has had some chances to do some cool stuff, and I commend you for not backing down. It takes a lot of courage to make the choices you’ve made over the last 9-10 months. I think that you’ve met some extreme challenges and some extreme uncertainty going down the road you’ve gone down. But I think the coolest thing I think at least I take away from these three conversations we’ve had, diving through your history, is that you kind of – you have no fear, you know? I mean, there’s a little fear there, but it doesn’t stop you from doing, and that’s really awesome, man. I’m really excited to have had a chance to share your story with everyone else, and for those who look up to you and those who wanna learn from you, that they’ve had a chance to hear an uncut, unedited version of the last year of your life, basically, and I guess then some beyond that, but mostly around the last year.

Yeah.

Anything you wanna close with before we say goodbye?

Yeah, I mean on that, I think we talked about it in part one or two - that thing on how to learn, just go do it. I think anything taken away from all the stuff I’ve done, I definitely have always been qualified for the jobs I’ve had… I mean, in high school I said I would make this YouTube competitor thing for a guy and I had no idea about video encoding, or even good web development, and I just started doing it and learned about it. So there’s really nothing stopping you from doing anything. Just go do it. If you need to learn something, learn it along the way while you’re doing. I don’t know, that’s a very important thing to me, and I think I definitely wouldn’t be anywhere near where I am if I just didn’t go do things, so… Go do things.

Go do things. So if you’re listening to this show and you’re on the edge of your seat, you’re thinking “Man, I should go do some things…”, Sam says “Go do some things.”

Go do it.

Well Sam, thanks so much for taking the time out of your life to share this time with me and to share your story. Again, I really appreciate how honest you’ve been about so many things that many people aren’t very honest about, honestly. That’s super cool, and I really thank you so much for doing that. For those who are listening to part three of Sam Soffes, thank you for listening and thanks for all your support of this show and myself. Keep following, this show will not end; it will likely never end, so… Keep listening. Until then, that’s it.