Garrett Dimon: All right. Hello. We are here today with Josh Williams who is now just a designer. You might be familiar with his past work, Gowalla, Blinksale, and Firewheel Design, among other things. How are you doing today, Josh?

Josh Williams: Doing great. Good morning. Thanks for having me.

Garrett: All right. Yeah, of course. Of course. No, I’m excited about this. I guess, give us a brief overview of how you got into web, how you started, and the wild journey you’ve been on to get to where you are now, in 30 seconds or less.

Josh: In 30 seconds or less?

Garrett: Take as long as you need.

Josh: Yeah, no. So I actually … I started volunteering at our church when I was a teen as a graphic designer doing an afternoon a week, just working on projects, and so that was when I was 13 or 14. My mom kind of had a graphic design background, so I was doing … It was Illustrator and PageMaker, and just did traditional graphic design work, and then around about ’95, ’96, I had a friend who was hiring me to do some odd jobs and was like, “Hey, you should learn to code since this graphic design stuff is gonna be on the internet at some point.” He pushed me pretty hard into that, and it turns out, he ended up being right, so that was kind of what pushed me to take the stuff that I was doing for print design and start doing it on the web in addition.

I loved icon design. I had a hobby habit of replacing the trashcan icons on MAC OS7 and all that sort of stuff. I nearly got fired for system resource editing at one of my jobs, so you learn things that are fun but kind of nefarious at a low level. A hobby turned out to be kind of a job. It turns out that iconography and that, there was a couple companies doing that at the time in the mid, late-90s like Icon Factory, and they started throwing some extra work my way, and hired a couple of friends, and next thing you know you’ve got a small agency doing iconography and user interface design work for software and that’s what ultimately became my first studio Firewheel, and everything else came out of that. Yeah, so that was my background, just a graphic designer and ended up in the web world, and then also went mobile from there.

Blinksale was an outcome from our studio, just building a service that we wanted to use ourselves.

Garrett: That’s one of the things that I absolutely love about having watched Firewheel over the years is you really … You look at how everything got chained together, and Gowalla even came out of that icon design work. So much of what you did … Blinksale I guess was obviously very heavy on design and I’m sure you’ve got some stories about the lime green that would be great to talk about, but can you talk, I guess, kind of about the transition from how you got into a product and then how you kind of gravitated back and got into what eventually became Gowalla and the path to Gowalla through all the icons and everything else.

Josh: Yeah. So, as Firewheel began to grow … This is the era, 37signals had just launched, Basecamp, there was kind of these early Ruby on Rails apps that no one had really … I mean, this is Web 2.0 if people actually remember that. In the midst of that, we were growing our own services, we were a small organization, and I was increasingly doing more overhead work than actual design work, so the question was, how can I eliminate redundant tasks from my workflow? One of those, obviously, just the act of bookkeeping and invoicing and the like. Inspired by others out there, I thought, “Hey, let’s build a little invoicing service to streamline that process for us.” Turns out, it’s a need that other people have as well. There wasn’t, at the time, a lot of great solutions for that. Blinksale was an outcome from our studio, just building a service that we wanted to use ourselves.

The first version design and build was four or five months, conceived in March or April and shipped in July. The first version was very much one of those, you put it out there and you invest out of the profits of your business. At the time, we were still really a three-person shop, and I hired a contract engineering, Scott Raymond, who ultimately became a co-founder with me at some of the later opportunities. So, you’re using your own profits to build this thing. There’s a little bit of, “I don’t know if this is going to work,” and initially, I still didn’t know and thought we sunk at the time…it seems so small now, but at the time, it was like $30,000, $40,000 worth of effectively of getting company profits that you’re putting into a project like this.

It wasn’t until probably nine or ten months later, when we shipped the second version of Blinksale and then raised the prices that you start to feel like, “Maybe there’s a time in the future where we make that money back where this becomes a profitable endeavor.” This really wasn’t the case of “we shipped it and it was instant success.” We shipped Blinksale. It was still a lot more work, and I think now we could’ve looked at it, and it said, “Okay, well, we spent all that money and now we have this service that’s bringing in maybe a couple thousand dollars a month. That doesn’t really justify the upfront expense.” We pushed it through, and we’re getting there, but I’m glad in retrospect. It wasn’t easy, and a year later we’re finally, “Okay, this might work out.”

That was still, I think, very early in that software-as-a-service days, and it started to grow. It’s funny because I was maybe 25 at the time, and after the second version, I got a call from Sequoia Capital out in Silicon Valley. We were still in Dallas. He was like, “Oh, have you ever thought about raising money for Blinksale? Would you like to come out and talk to us?” I didn’t know a thing about that world, so I got a plane with an attorney friend of mine, and we went out and spent a day at Sequoia. I wouldn’t even say we pitched them on it because I didn’t know what a pitch was. It was more like, “I’ll show you what we built.”

I remember when we met with an investor, whose name was Roelof Botha was like kind of a superstar. I had no clue, at the time, who he was, and I remember Roelof asked, “Oh, what do you think that there’s a chance that you could grow Blinksale into a $50 million a year business?” I was just like, “What?” Honestly, I think it probably scared me off is that realization of, “Oh wow, this is the outcome that they expect if they’re going to invest in a company like what I built here at Blinksale.” That was the farthest thing from my mind, a number like $50 million. The funny thing now, let’s fast-forward 10 years, and I look at it, with hindsight and what I know about the industry and what I know about venture capital, and I think, “Oh man, we totally could’ve done $50 million a year with that.” I look at some of the companies that have actually grown and filled that space, and they’re really profitable successful companies there. That was, in some ways, just a naivety of my part of what could be there.

Now that it’s said, I still don’t know that I would’ve wanted to do that. I think financial software is really hard. It’s one of the reasons why I ultimately kind of moved away from it and chose to focus on other things, but certainly, I think the validity of the idea at the time, and what I still think is still a valuable service today.

One of the other ideas that we had, again, building for designer tools, was this thing called IconBuffet, and it was kind of this crazy community for designers who wanted to swap stock icons. For us, it was really just a marketing gimmick to, again, sell our stock services and market our products.

Garrett: Yeah, absolutely. I think what’s really interesting in that, too, is that Blinksale … What was the timeline around that versus kind of starting to move into other apps and doing other things? What was the sequence of events that led you to go … I mean it sounds kind of like, “Okay, we don’t want to be in financial,” but what are the other things that led you away from Blinksale ultimately to focus on other areas?

Josh: We talked a little bit, before I got out, about what was the transition like from a pure services company to a product company. As Blinksale grew, probably as we reached…again, we launched in 2005…It was well into 2006 before that maybe there’s a light at the end of the tunnel. Then another year passed. You get into 2007 and Scott, we hired full-time at that point to work on Blinksale. We hired another engineer to work on it. I had a team building up, and it had grown into basically being half of our operations revenue, so half was coming in from Blinksale and half was coming in from client work. The thought from me was were there other ways that we can continue to invest in products divert ourselves from having to do as much client work and to continue these flows.

One of the other ideas that we had, again, building for designer tools, was this thing called IconBuffet, and it was kind of this crazy community for designers who wanted to swap stock icons. For us, it was really just a marketing gimmick to, again, sell our stock services and market our products. It turned out that community took off and had legs itself. It made money, but not significant amounts of money, but the community was super vibrant. There was tens of thousands of people on there that were swapping icons, and it was just this weird thing at the time.

One of my clients, at the same time, was a fellow named Shawn Parker, and some people may know him as Justin Timberlake from the Social Network. Shawn, who is nothing like what Justin Timberlake portrayed him to be, but it’s still funny. Shawn took one look at IconBuffet and was really intrigued with what we had built, and this was, well, about 2007 when Facebook had launched, you know Facebook platform. It was the first time they had opened that up as third-party developers. Shawn, I’m oversimplifying it, but basically said, “You should take IconBuffet and put it on Facebook platform, and just make it a game. Forget any of the market, your design studio stuff. Just take the basic mechanics of, ‘I’m trading and swapping pixels,’ and put them in a social environment and it’s got to be a success.”

It turns out Shawn was pretty prescient on that. We ended up building this thing called PackRat, which was a social game that pre-dated Farmville and all the Zynga games but very much shared some similar mechanics of what we had built with IconBuffet. You unlock these icon cards, very, very rarely, you swap them with your friends, and we built a business model around it. Again, it turned out to be cult hit type success, never the bajillions of users that Farmville was pulling down for a team of, at the time, of seven, 10, 12 people. It was more than profitable. We did really well off of PackRat.

It was at that point that, now we had PackRat that was legitimately doing major revenue, and Blinksale was still a thing. I was kind of forced to do this. Quality was important to us and so there was just a question, where do we want to invest our time? We couldn’t do both, and so we had to decide where did we want to put our eggs. What basket do we want to put them in, and so we made the decision to do our thing with PackRat because it was obviously growing faster and had larger revenue. Sadly, that was when Blinksale just wasn’t getting the attention that it needed, and it still had plenty of customers, still profitable, still doing its thing, but we weren’t getting to bug fixes fast as we wanted to or adding features as fast as we wanted to.

It probably existed in that state for about six months or so before a fellow … I don’t know if you know Brandon Cotter. He’s part of that Dallas, Texas space. He came along and said, “Hey, you’ve got this thing. Do you have any interest in selling? There’s the business there, and I put the time into it.” I had known Brandon for a while. I didn’t seek him out on the thing, and it turned out to just be, I would say, a decent situation in terms of finding somebody who wanted to put the effort in and put a team around it. For us, it was a way to move it to a home where it would get the attention that it needs while we were focused on something else.

In a lot of ways, it was one of those decisions that seemed really natural and kind of made itself at the time. There wasn’t a lot of serious thought. It was just the right move to make, both for us and for the Blinksale product and community to have a dedicated team behind it that can give it the attention that it needs. Again, it’s, I would say, a little bittersweet. Then I look back at it, and it’s like I haven’t played the hand that was PackRat and Gowalla, and you see that. You look back like, “Well, that other hand could’ve been pretty good too.” I think they were both viable businesses, and we chose to move one on in its current state. It was all a successful endeavor for us. I’m glad that we did it. It was a great opportunity to sell it off at Brandon at the time, and Doublewide Labs, who continued the work, but it’s your baby.

I look back at it at times and think, “What would it have been like to have continued work on it?” Because I do still think that the idea and the space was one that was good. That’s where we kind of parted ways with Blinksale and dove full time into PackRat. I think the outcome of PackRat and that experience of building it is we realized that we had built this community that basically had gamified sitting on your butt for 10 hours straight in front of Facebook. We were looking to do a game because we knew, “PackRat is going to get this big, and it’ll go on, but what else can we do that allows us to keep growing here?” At this point, it’s 2008, 2009. Apple releases an iPhone that has a GPS in it and this crazy idea of, “Okay, let’s take the same mechanics again, icons that can be found, discovered, traded, and put it into the real world instead of trading icons in front of your computer, we’ll get you to go out and explore the real world to do this.”

That was kind of the genesis of the idea behind Gowalla. You know, let’s just make icons for all the places and you can go out and collect them. Then it turned out that was popular, too, again. No super prescient foresight on that one, just happened to strike a chord that I think a lot of people got into. That was again early days for an iOS as well. Now, there’s so many things and so many interesting ideas, and back then, it was still very green field and fresh. I look at, even from a timing standpoint, though, and from an IP standpoint, the success, especially last summer with Pokemon Go, which had very similar characteristics to what we were doing with Gowalla. It actually shared a board member as well, so there’s a little bit of shared DNA there. I think it speaks to the fact that the idea was a good one. The timing and technology has evolved a long way, so I think you still have these opportunities to build these big hits. I think the Pokemon IP certainly helps a whole lot in terms of raising awareness.

We raised $10 million. You know, at that point, there’s one of those questions of how do you justify the outcome. We were spinning through that money.

Garrett: Just a little.

Josh: Yeah, just a little. I think that I’m really proud of what we built with Gowalla. It was, I think, special for the time that it existed.

What do you want me to talk about from that?

Garrett: No, no. This is good. I’ve got a slew of questions from all this. One, there’s definitely no doubt that everything that you all created was loved by the people that used it. Not just like, “Oh, this is a neat app.” There was a really passionate group of users around everything that you built. I think that speaks to a lot. I think a lot of it, like you said, it’s just the kind of market forces and timing can play such a role in how that all works. I absolutely love how there just wasn’t a master plan to any of that. So many people, I feel like, set themselves up, and they want to have that perfect idea. They can say, “Let’s go all in on this idea,” and they wait forever and ever before they actually commit to anything and really try it. Then nothing ever happens.

it’s not always going to work if you just go chase every idea that comes into your head, but the idea of pursuing these different channels and really pursuing them, not just dabbling in them, but saying, “Let’s go do this.” One thing connects to another, and you can see the exact line, even Blinksale. I’m sure a lot of the technical experience you gained from that factored into PackRat and Gowalla. It’s interesting to see how just by doing things, one thing leads to another, you learn, you gain experience, you’re pushing your boundaries, and you’re taking it one level further every time and obviously with no plan. You just were doing. I think that’s a huge thing that people can learn from, to just go out and tinker and play. Then commit to it and really kind of follow it through to the end and see how it plays out.

I’m not sure which of the two questions I want to go to first. I guess, let’s go ahead and continue this out, so Gowalla gets acquired by Facebook. How was that experience in terms of, here you are, you built this hugely popular thing, but just the way it was going and with Foursquare and all the other surrounding forces, how did that play out, and how did it feel making that transition and going from being a founder to an employee, again? Well, not again, for the first time probably for you really in a while.

Josh: Yeah, it is truly one of the first times for me, certainly in that capacity. It was certainly a difficult transition for a couple of reasons. One, ultimately we ended up raising, just due to the attention of the space, we ended up raising a little over $10 million for Gowalla over a couple rounds and had some just stellar investors and fantastic folks that we were working with there. We raised that money, and at the time, again, Foursquare was raising money as well aggressively. Both companies were raising that money somewhat under the assumption that someone in this space was going to become the next Twitter or the next Facebook.

The location sharing was going to become like a network in and of itself, and so the investment money that was coming into these companies was somewhat predicated on Gowalla being a social network or Foursquare being a social network. Ultimately, that didn’t play out as designed for either company, and both are gone. Obviously, we sold to Facebook. Foursquare’s changed their business model and has found a different path to sustainability at this point. At the time, those were the pressures and that was the expected outcome.

Facebook ended up launching a check-in feature, and when things started to look more clear that Facebook’s going to gobble the social side of this up. We raised $10 million. You know, at that point, there’s one of those questions of how do you justify the outcome. We were spinning through that money. We didn’t have enough revenue coming in to justify the overhead of the headcount that we had hired kind of on this expectation that we’re going to go exponentially up into the right, and so you’re forced to reconcile the, “Well, do we go out and raise a bunch more money, to kind of fuel the fire now the space is starting to cool a little bit? Or do you kind of get everybody out, in so many ways?”

It was really difficult because we were not at an advantageous position, being number two player in the market, to raise money, and we needed to. It was one of those, we’re either going to be insolvent in six months, or we have to find an outcome. Fortunately, the outcome for us was Facebook. There’s a number of other places we could’ve ended up. We could’ve ended up at Yahoo or something like that. Nothing against Yahoo, but Facebook was a great place for us to land, high quality people there, and we were able to land in a way that it wasn’t too rough. I say that in a sense that it was actually rough in a lot of ways, but it could’ve been disastrous and it wasn’t.

The tough thing for us, it was an era where Facebook was growing. They were trying to acquire talented design teams. Our team fractured going through the acquisition process. A bunch of folks didn’t continue on with Facebook and it sucked. It sucked for us as a team to have to have some of us go on and some us didn’t. I really hate the fact that we ended up in that situation. I hate the fact that Gowalla doesn’t exist as a product that we did not find a way to make it sustainable because I think there’s something beautiful there, and the ideas and things that I’d love to re-explore. When it’s all said and done, it could’ve been much worse, and everyone kind of got out with their shirt on. For some of us, we moved to California, and we went to work with Facebook. I ended up working on location and events and pages and a number of products there as a product manager.

It was a really great learning experience to be with a larger company like that and see what the process and the rigor was up in an organization that when we joined had 3,000 people and when I left had close to 7,000. It was pretty crazy watching that happen and being a part of that. It was, for me, having run … Thankfully, my one started for, at that time, probably 10 years. Then to jump and go from like, “Hey, I’ve run a start-up, which is a win in and of itself,” to now I’ve landed on a really high velocity large company. There was no rest for the weary on that one. It was just kind of jumping from one fire into another but an enjoyable experience, good people.

it’s one of those places that you know, at times I think I could’ve stayed there longer, but I ready to step out and try some of those things again. I still have to leave a lot when we were doing this Gowalla and felt like we had not fully been able to explore some of the things that we wanted to. After some time, that’s when I made the decision to step back out and start Last Guide, which was co-founded with Adam Michela, Soopa, who would’ve been at Gowalla and gone on with us. Keegan came over. Some other former Gowalla people were part of that, and we hired a really great team. A super talented team, former Apple, former Dropbox, former Facebook people kind of go back into global location space again. Last Guide was a very interesting period for me in the sense that, I think esoterically, we had in our mind we kind of knew what we wanted to build. It certainly wasn’t concrete by any means, but we had a lot of amazing people who wanted to come work with us. We raised a small amount of money and it was enough to like, “Okay, let’s hire these and we’ll figure it out as we go.”

In retrospect, I would’ve kept the team small again, but it was like, these incredible people want to come work with us. How do you say no? We kind of grew that team up a little bit. We shipped a product called Goji that was kind of an experimental keyboard built on top of the platform that we ultimately wanted to build with Last Guide. It never saw the light of the day. The general gist was that, in Gowalla, there’s a feature called Trips that was very popular but never got the love that it wanted, so we kind of wanted to re-explore, how do you make these self-contained guides, if you will, and serve them up in a contextualized way? So that if it was a sunny afternoon, we could say, “Hey, heres a list of beer bars with patios you could go hang out at right now,” and push those to people.

There’s a lot of really cool ideas that we had, and again, we shipped Goji, which was kind of a preview of that. Then right in the middle of that, we were about, I guess a year into Last Guide, my grandmother passed, and my father, whose cancer had been in remission, his cancer came back. This just blew up my year. I ended up having to, over the course of basically six months, be gone attending to family for three or four of those, and it’s just not a good mix for venture-back start-up. For anything, I look back, and it’s like I’m happy with the things that we built. I structured the pacing of the company a little bit different and then sometimes this shit happens and there’s nothing you can do about that.

A bunch of folks didn’t continue on with Facebook and it sucked. It sucked for us as a team to have to have some of us go on and some us didn’t. I really hate the fact that we ended up in that situation.

Garrett: I’m vaguely familiar.

Josh: Yeah, no doubt, right? It is what it is. We gave it some thought about it like, do we reboot it so to say? Do we try to put a little more fuel in the tank and jumpstart it again? At the time, I was exhausted, and I think Soopa, Keegan and some of the others, we all were. It’s just, we had been part of the team. We had been working at Gowalla together, we spent time at Facebook together, and now we’re working on this and it was just like, “We need a break.” I wasn’t in a healthy place.

Garrett: I completely relate. That is in a lot of ways very similar to what I went through with Sifter in deciding, “Okay, I need a break from being …” It was a different scale obviously, but it was all on me to carry everything, and it was definitely not something I was up for, so I completely relate. In terms of bootstrapping …

Josh: So you hit the big red button. It’s like, “I’m out.”

Garrett: Yeah, exactly. I don’t think I’ve had any regret, but there’s constantly a, “You know? I wonder. Could I have let it falter for a few months, kind of regained my composure and gone at it again? Would that have been the right thing for customers? Would I have been happy doing that? I don’t know.” There’s always going to be questions, but I feel like ultimately, it was the right decision, and that’s kind of the most you can hope for.

Josh: Well, you’re in a similar situation as me too. I think our families are like similar stages, and you also reached that place, too, of realizing, when I was 25 and I didn’t have any kids and I had a certain capacity and certain bandwidth you can do this. Now all of a sudden, you realize, “Wow, you know, the stress that I put on myself also has these downstream effects.” You do have to ask yourself, what’s the trade-off? I think for me, it was just that realization, there’s a season for everything. This isn’t that season, and I need to take a step back.

Garrett: I know, now working at Wildbit, I’ve even joked with Chris and Natalie Nagele, at some point, I’m not going to be able to stop the itch. I’m going to want to go try something again. I don’t even know what yet or when, years from now I’m sure. Yeah, it’s one of those things that there’s an ebb and a flow to it where doing that, seeing the people that do that non-stop for decades. I don’t know how they do it. They’re machines.

One thing I definitely want to hit on is bootstrapping versus raising money. We’ve kind of touched on it that raising money puts you in a whole different category of pressure and different expectations. In hindsight, having done a little bit of both, and going through that and had the outcomes you’ve had, what do you see as the pros and cons and based on that, what would you do differently in hindsight?

Josh: Let’s see. Some of the pros and cons, I think, are well-trod paths. There’s obvious ones like with kind of bootstrapping is you’re in main control. You’re not giving up equity to somebody else. You can grow at your own pace and control your own outcomes. The cons of course is that you’re limited to the speed at which you can grown. You may or may not see that as a con. It’s just a lot of work. Again, you may or may not see that as a con, but the act of bootstrapping Blinksale and bootstrapping IconBuffet as one of the early things that we did where … it didn’t happen over night, and so you are having to kind of do that on the edges. You have to put in this extra time on top of the time that you’re doing your services to pay the bills or doing your day job or whatever it happens to be. You have to realize that time’s going to come from somewhere, and it’s going take that extra work.

The flip-side is, ultimately for me, being able to build something with your own hands and know at the end of the day, this is mine. It’s satisfying and fulfilling to do that. I think if you have a business model where there’s obvious money that’s coming off the back. It makes a lot more sense to bootstrap as long as you can because, again, you kind of prove to yourself that this is valid.

Raising capital, I think, there are certain things where, again, market timing and such that there’s an obvious advantage to being able to move into and market quickly and establish yourself and scale a product faster. There are reasons to do that. I think for Gowalla, at the time, what we were trying to do and how we were pitching it, I think raising money was the right thing to do at that time, in that window.

The flip-side to when you do that, the outcome expectations are different, and it certainly was with regard to Silicon Valley style of venture capital. These investors want a legitimate outcome, and we’re talking not 10x, we’re talking like 100x, 1,000x, massive, massive outcomes, which mean when you go and you raise money, you know a few million dollars from one of these firms, there’s an expectation that these companies are going to have. $100 million, billion dollar outcome, not like, “I sold it for $10 million,” not like, “I raised $2 million, we sold it for 10, and now it’s a success.” That’s not the game that’s being played. “I raised $2 million and then $10 million and the $20 million and then we sold this for a few billion.”

That’s a really aggressive game to play, and I think that there’s a lot of companies right now that are being started that aren’t coming into it with that mindset that it’s like, “I’m going to raise money but ultimately what I want is a lifestyle business outcome.” I hate the term. A lot of people hate that term, but I think the outcomes are different. I think there’s a lot of companies that are raising money right now that shouldn’t be. The outcome will never justify what was raised to put in.

This is actually one of my things now. With the gloss gone that Gowalla’s not going to become the next Facebook social network, the ideas that were there I think were interesting and I have some concepts and things that I would love to re-explore, but I have a really difficult time thinking about them in the context of re-exploring it as a venture-backed company. I think there’s a lot of things that I would try to re-explore under the guise of, how can I bootstrap this again effectively myself?

What’s difficult is that nothing exists really in between. There have been a few outfits like and some others that kind of exist in this seed-structure financing that have expectation of a different outcome. I would love to see more of that. One of the difficult things that does not exist right now or is much more difficult is the ability for small business to go and get a loan.

My parents built this amazing landscape company in the Dallas area. It was a traditional small business. It employed 30 people, and lots people went shopping there every weekend to buy plants and flowers and shrubs. It was your typical American small business. It was a lot of hard work, but it was a success story of a certain scale. They did that because they were able to get a loan to build some greenhouses and to prove that they had this idea that they could get capital for and pay it back in, we’ll say reasonable terms. You can’t just go down your bank and get loans for that sort of stuff. On the flip-side the private market is generally over in debt towards venture capital, so I think there’s a market for something that kind of exists in between. People like are doing that but there definitely needs to be more of things that allow you to like, “Hey, I could use a little capital, but at the end of the day, the intent is to pay this back with some interest.” I still own my thing.

Garrett: Absolutely. There’s middle ground on the spectrum right now. There’s not a lot of coverage. It’s bootstrap or go raise money and start that timer on yourself.

Josh: That’s right.

Garrett: But there’s not a lot of middle ground. I love the ideas that is pursuing and talking about. I know I’m kind of excited to see how that shakes out and if it gets more people interested in healthy returns instead of economical returns.

Josh: Yeah, that’s right. That’s where I think, it’s like if you’re in your mind, if you’re that guy who hears the investor say, “Hey, can you grow this to $50 million a year?” and you’re like, “Absolutely, I can.” You have that confidence level of that. I get it. That’s the outcome I’m going for. Then go out and raise that money, but if in the back of your mind you’re like, “Oh, I actually never thought about that, and I don’t know if this business is even capable of even achieving anything like that.” Then I think you need to question, “Why am I raising this money?”

Garrett: Yeah, very true. We’re starting to get along on time, but there’s a couple more things I want to hit on. One, talk a little bit about what your plans are now with designing or are you just taking a step back after the roller coaster you’ve been on and catching your breath? How’s that going?

Josh: Yeah, after we dissolved Last Guide, I just decided, “Hey, I still got kids. I got college education to pay for at some point for them,” but I didn’t want to jump into starting another company, I just couldn’t. So, I thought, “Hey, I love design work, I love working on early stage products, I love working on early stage brands,” so I just do it for some other people. I’ll go work with some friends, help them out in their companies and then just go back into design consulting again. I started doing that about a year and a half ago. I did work on some interesting projects with different folks and in the midst of that, my wife also decided that she wanted to jump back into school and go to culinary school, so that precipitated as us moving out of San Francisco up to Napa where she’s in culinary school up right now. For me, it was just a matter of, “Hey, I can still continue doing design consulting from wherever.” I go out to the city every other week or so, work with clients down there, otherwise, work from the house here, where I am right now.

In the same way, I’m doing brand design work again, I’m doing some product design work, I work with one or two clients at a time, and I really enjoy that work. I enjoy working on early stage stuff and it’s nice working on somebody else’s problem, where, at the end of the day, it’s not like I’m not the one having to deal with the problems.

Garrett: Yeah, it’s their problem.

Then right in the middle of that, we were about, I guess a year into Last Guide, my grandmother passed, and my father, whose cancer had been in remission, his cancer came back. This just blew up my year.

Josh: it’s their problem, but it’s fun. It’s fun to work with, again, I think, small teams where you can build something in that environment. I spent a lot of time working, over the last year, on an email client called Astro, it’s a mail box style native Mac and iOS email client that exists in a Slack area. I’ve been working on that, doing a couple of brand design projects. At the same time, I’m back to the, “Okay, well how do I … I want to do my own projects again but I don’t want to do a company right now.” So I’m like, “What do I do?” Some of my other … I’ll tell you my other little side thing. Over the holidays, I made this crazy calendar. This goes to my love for iconography and the like. It’s kind of the same thing, I thought, “Oh, I’m going to do a calendar for some friend and on all the holidays I’m going to sub out the dates for emoji and replace Christmas with a Christmas tree and Easter with a chick coming out of the egg, and so on.” So, I get this calendar.

I’ll show you what I’m doing over here. I’ll hold it up. It’s like one of the early computers. It was like all of the unit calendars, it was in a code for all these unit code characters. You can see the little black ones here, all the icons. So I gave it to my friends and it turned out that everyone started asking where they could buy them, and I’d never intended that because I just took a short rent of them. So now I’m like, “Okay, I’ve got to do this for real now,” so I’m gearing up to a lot of the unit calendars, some other stuff, start producing my own products again and we’ll see. At the very least, still some things on the side. It’s nice to work on some things that I’m interested in and I find fun.

Garrett: We’ve seen where your creative endeavors end up pulling you, so be careful that you’re not in Sand Hill in a couple of weeks raising $50 million for your calendar business.

Josh: I know. Trust me, I’ve been down the path enough times now. I actually really cannot complain about my life one bit. At this point, I live in a really small town and my kids go to school a few blocks from where I live. My wife is working an externship at a Michelin star restaurant right now, tending their garden and working their grill. It’s pretty great. I don’t want to go back to Sand Hill and do that at this point because I’m pretty satisfied with my design work and maybe my calendar. For the time being.

Garrett: It is really funny, the parallel. We’re moving to a town of 3,000, our girls will be two blocks from school, you can walk everywhere type of place, and that’s what’s appealing right now. Slow down, stop the whole constantly feeling like you got to do more and grow and grow and grow, just take a step back and breathe. It’s been …

Josh: it’s exciting.

Garrett: We’re not there yet. The moving process is pain, but theoretically, it’ll be good.

Josh: Yeah, healthy.

Garrett: The one biggest question. Looking back at all this, and this may be kind of the same, it’s kind of a two part question. Through this whole journey of yours, what’s been the worst day? The roughest day, just to get through that day. How did you get through it? And then, if you could go back to the very beginning and tell yourself one thing and know that you’d actually listen to yourself, to do differently, what would that be?

Josh: I think there’s probably two days that stick out. One was the day that kind of come to the realization that we’re going to have to sell Gowalla to Facebook. I say “have to” in the sense that we were incapable of continuing as an independent organization. You come to that realization like, “We’re not going to be able to raise funding the way we want to, we’re going to have to sell to someone.” You feel helpless, especially knowing that users believed in you, the employees believed in this vision, you were all building this thing together and it’s not going to work out. There’s an overwhelming sense of deployment, both in yourself, and the unknown of, “What are we going to do now?” It was horrible. I remember we were just in the deepest pit. It’s weird to say, “Oh, you’re selling to Facebook and everything,” but at the same time, it wasn’t what you were … and it’s no fault of Facebook’s at all. That’s just the nature of what we were.

And then, the second was in the middle of Last Guide, my dad’s cancer came back. He actually ran away. He was on a bad medicine trip and ran away from home in the middle of all that. That was right when we were at a critical point as well. I had to do everything and literally go find dad and there was that realization, same thing of, you have employers that wanted more out of this and there’s nothing you can do to change this outcome at this point. It’s like, “What, are you not going to go find your dad now?” Instead, people are going to sit around wondering, what are they actually supposed to be working on for the next several weeks while we’re sorting our life out?

In both cases, now with hindsight, I think the thing … I don’t know if there’s anything I could have changed. But I think time has a way of … when you’re in the midst of those things, everything is tough, there’s no light at the end of tunnel and you’re just done. Retrospect, you look back and there’s a realization that it’s not the case and as horrible as those moments were in the midst of them, they were, it sounds cliché but, a little bit character producing. Ultimately, it shines a little bit of light on, at least for me, what’s the most important in life? I had this realization that the relationships with my coworkers at Gowalla were ultimately very important and the relationship with my family has been very important over the last couple of years as I dealt with some of the stuff.

In the midst of all the business dealings and decisions, you do kind of have to finally ask yourself, “Okay, at the end of the day, is it more important to me we raise this money or get this deal done? Or do I do right by people?” I’d like to think I’ve done a decent job of that. It’s hard. You can’t please everybody and I know when I look back, situations with certain coworkers were even starting to message me. I dropped a ball on that one and it sucks. You have to come to peace with some of those things. Not everything is going to be right, but there’s ways that … time doesn’t stop. There’s more that can be done. You can, I think, continue building.

What’s great is, for me, I was on vacation last week my my family in Hawaii and randomly bumped into a woman who was one of our earliest employees at PackRat and Gowalla. She actually, just turns out she’s moved there. It was so amazing, we haven’t seen each other in ages. Really fantastic to still have these relationships intact, even though the adventure that you went on together has long since come to a close, so I think keeping those connections, those relationships strong is really important because, ultimately, none of these things you can build on your own, even if you own the whole thing and stuff. None of us are working a vacuum and keeping these relationships strong is really important.

Garrett: it’s interesting that it’s almost always, whenever I ask people, it’s so frequently times where people feel like they let people down. Either their team or customers or whatever it is, it almost invariably comes back to that. In a lot of cases, it’s raising funding and having to take pay cuts or let people go, or whatever it is. It comes down to that, everybody’s toughest day is when they’ve got to tell people bad news or buckle down and make something work when you’re a bad situation. It’s interesting.

Josh: That’s right.

Garrett: So, the last part of that then, if you could go back to about 2004, 2005-ish and give yourself some advice to do something differently, what would it be?

Josh: To do something differently …

Garrett: Doesn’t have to be huge, doesn’t have to completely change the game.

Josh: I think that, for me, if I look at the part of my life that, I hate to say suffer, but it’s probably the best way to describe it, that suffered the most, where I sacrificed the most was probably family impact, especially when my first daughter was an infant, my second daughter was born. We were raising money and it was high stakes. We got it high stakes for whatever reason. It put a lot of stress on my family, I was traveling a lot, and there’s a lot of things that you think, “Oh, this one thing is the thing that’s really important, it’s going to make a difference,” and you look for a lot of, what are these big hits that are going to … that all of a sudden are going to be the thing that changes your trajectory. Chasing those big hits, if you will, you can pull a lot of time from other things that are important. I think that’s the one thing where, again, bootstrapping a certain way, at least changes the pacing.

You do have to ask yourself, what’s the trade-off? I think for me, it was just that realization, there’s a season for everything. This isn’t that season, and I need to take a step back.

Garrett: You still feel that way.

Josh: Still feel that way. But, that’s one of those things that, looking back, I would tell myself, “Hey, don’t chase these opportunities at the expense of people that you’re going to be living your whole life with.” I feel like, as much as I’ve had a reasonable number of successes and failures, there’s not a lot I would change. I look at it like, “Well, this has actually been a pretty interesting journey.” I’ve learned a lot and I feel to the very least I work on things that have stayed true to the sorts of things that I’m interested in and I’m happy about that. That part I feel like I’m very pleased with. If anything, you don’t sniff the crap on your own shoes too much. But otherwise, I feel like it’s been a good journey.

Garrett: Right on. All right. Well, that is all I’ve got for you. We kind of ran a little long but I think it was worth it.

Josh: It was good fun.

Garrett: Thanks for taking the time to do this. I really appreciate it and I’m sure all the listeners will as well.

Josh: Awesome. Thanks, Garrett.

Garrett: Thanks.