RunKeeper: How A Non-Programmer Launched A Huge Software-Based Business

There’s a shocking moment towards the end of this interview when I ask Jason Jacobs what kind of internet connection he’s on, and he says he’s “technically illiterate” and doesn’t know. The guy founded RunKeeper whose app has been installed on millions of mobile phones because it automagically lets runners track and share their runs. How did he do it if he’s technically illiterate and can’t code?

If you listen to this interview (and you should really listen to this one, not just read the transcript, because so much of how he did it is in Jason’s voice), you’ll know instantly. The guy is so passionate about his idea that developers and designers wanted to work with him, even before he had enough money to hire full-time coders. I know that sounds overly simplistic and you want details. The details are in the program.

Jason Jacobs

Jason Jacobs


Jason Jacobs is the founder of FitnessKeeper, the company behind RunKeeper. RunKeeper makes tracking workouts fun, social and easy to help users understand and improve the quality of their fitness.

You can see Jason’s runs on his RunKeeper page.


Full Interview Transcript

Andrew Warner: Before we start, you’ve probably seen posts like this on TechCrunch a lot right? Where they list all the startups that were recently launched at FounderInstitute. I want to call your attention to it because FounderInstitute is accepting applications right now and I hope you apply. If you’re accepted, you’ll have access to experienced CEOs as mentors, you’ll get introductions to investors, you’ll have access to the press and other resources to help you launch your company right. They’re accepting applications right now at


Remember Patrick Buckley, who I interviewed? He’s the guy who came up with an idea for an iPad case, and he built a store to sell it online. A few months after he did that, he generated about a million dollars in sales. The platform Patrick used is Shopify. If you have an idea to sell anything, set up your store on because Shopify stores are designed to increase sales. And, because they’re so easy to use and set up, even if you have a friend who’s not a techie the way you are, if they’re looking to set up their store, you can recommend that they use Shopify and trust that they’ll have an easy time setting it up without calling on your for tech support.

Finally, do you remember when I interviewed Sarah Sutton Fell about how she got thousands of people to pay for her job site? Look at the biggest point that she made when we talked. She said that she has a phone number on every page of her site because, she says, and here’s a stat, 95% of the people who call end up buying from her. Most people don’t call, but seeing a number, a real person that can be accessed by phone, increases their confidence in her and they end up buying. Try this. Go to and set up a phone number that will make your company sound professional, not like one of these freebies, but a professional, virtual phone system that you’re going to love, and add that phone number to your website and see what happens. You got to try them to know why I keep talking about them.

Here’s the program.

Hey everyone. My name is Andrew Warner. I’m the founder of, home of the ambitious upstart. When I say home of the ambitious upstart, I mean I’m targeting a narrow, narrow, very tiny group of people out there on the Internet who would rather not look at the top links on Digg for the day or figure out what’s funny on Reddit, but instead would want to spend maybe an hour of their time listening to an entrepreneur talk about how he built his business and they get fired up by that much more than they’d get fired up by a, I don’t know, Lady Gaga video on YouTube. That’s my little audience. That’s who I fight for every day.

To help me do that, I’ve got Jason Jacobs with me. He had an idea that he was so freaking passionate about that he decided to just jump in and launch a business. That vision became RunKeeper, an app that you can install on your mobile phone to track and improve your workouts. RunKeeper was cash flow positive every month since inception and he just told me before this interview that it’s been downloaded over two million times. I invited him to Mixergy to hear how he got so many downloads, to hear how he got cash flow positive so quickly, and to find out how he stands out in an environment where there are just so many mobile phone apps that it’s tough for us consumers to figure out what’s out there. He’s got two million of us who have downloaded the app. Jason, welcome to Mixergy.

Jason Jacobs: Thanks a lot Andrew. Very happy to be here.

Andrew: Thanks. By the way, is it two million downloads or two million people who have downloaded?

Jason: There’s been well over two million downloads of our iPhone application alone and we launched on Android a few months ago, so we’ve got many hundreds of thousands of downloads there and gaining quickly which we’ve been really happy about. Not just RunKeeper but the overall Android platform has surprised us as well. We’ve recently enabled people to create accounts on the web that don’t have any mobile device as well. We’ve got more and more sources feeding in but the iPhone alone, over two million people have downloaded it in the last couple of years.

Andrew: All right. You told me before this interview you just had this vision and you had to go out there and create it. Don’t all entrepreneurs. . . I know my audience is going to think, “Don’t all entrepreneurs just jump in there?” There were certain things that other entrepreneurs might have done before like raise money. Did you raise money before you launched?

Jason: No.

Andrew: Did you make sure that you had a job before you launched, that you were at least going to be able to feed yourself for the next few years?

Jason: It’s funny. Before I left my job, the two years prior to leaving my job, I was earning market salary and living like a bootstrapped entrepreneur and I was stocking away a ton of money. The reason was, although I had no idea and no team, I viewed myself as a serial entrepreneur who just hadn’t gotten started yet. It was runway to me even before it had to become runway. When the magic finally happened and the stars aligned and I had an idea I was so passionate about that I had to do, I had the luxury of having two years of runway for a significantly reduced personal living expense that I could leave my job and just go after it. That’s exactly what I did. No team, not a line of code written, and just an idea that I couldn’t stop thinking about day or night.

Andrew: Can you give me a sense of how you were living before when you were putting all that money away?

Jason: Before I went into pre-startup bootstrapping mode?

Andrew: Yeah. When you were in that personal bootstrapping mode, where you were just keeping things light.

Jason: Didn’t go out to dinner very often and when we did, my girlfriend at the time, who’s now my fiancee, we mastered the $20 in-then-out Vietnamese place down the street which we love. We cut out the vacations. The stuff, the watches, the clothes, the cars, I was never a big stuff guy, but that stuff got reduced to bare bones. I think part of it was that I was stocking away in runway but part of it was that I was working day and night to figure out that thing to pour myself into, let alone working on it once I actually locked in on it. It was actually a very frustrating process to want so badly to get down the entrepreneurial path and to not either have an idea that you believe in so strongly that you can put a stake in the ground and go wrap a team around, or a team that you believe in so strongly that you say, “I want to go to war with you guys. Let’s go find something to do.” I had neither of those and that was a process to get there.

Andrew: I want to understand that process, but first, because I know a lot of people want to go through that, a lot of people want to have that burst of inspiration that they can feel so passionate about that they would go out and get that army around them. I’m wondering too about you and your girlfriend. Small thing, but it’s significant at the time. You’re dating someone where you have to say, “Let’s not go out and have the great dinners that are available to us. Let’s go to the cheapo, $20 restaurant.” To a lot of people, that first reaction to doing that in the moment would be, “Ugh, we’re not going to have as much fun.” Or, “She’s not going to be as in to me. We’re just dating.” It can also bring a couple together, can’t it? What was your experience with that? How did it influence your relationship?

Jason: I’m enormously lucky in the sense that I found someone who not only cares a lot about me and vice versa, but who grew up around entrepreneurship. Her father was an entrepreneur and her mother was a public school teacher but was also very, very active in different events and thought leadership positions around the profession of teaching. Her parents were just really, really busy growing up. It’s in her blood. She also was working full-time and going to school part-time carrying three classes in a night MBA program at the time.

Part of it was that we were both really busy at the same time, but another piece was just that she was used to it. She’s drawn to passionate, ambitious people. Of course, she does miss doing the things that normal people do, but I think overall, she knows that letting me go after my dreams leads to a happier me which leads to a happier her. In return, I make sure that, although the profession is very demanding and all-consuming, that she gets the attention that she needs. It’s quite hard to balance everything and we don’t even have children yet. The people that do this once they’ve got a child or a family with multiple children, kudos to them.

Andrew: Yeah. I don’t know how they do it either. We’ll both find out soon hopefully. Well, not too soon. [laughs] What is the process of finding that company that you’re so passionate about that you’re willing to spend all your time on? How did you do it?

Jason: I was a liberal arts undergrad and then all my experience since college was working in small, high-growth, venture-backed technology companies. The interesting thing for my journey is that I got to a company a year out of school that was 100 people and two years later, when I left, we were more than 700 people and publicly traded and had a nine billion dollar market cap. It went down as quickly as it went up. This was ’99 to ’01, you remember those days I’m sure.

I got addicted to the process of building companies from small to big. I was specifically drawn to technology because of the pace of innovation and the excitement. I worked in these technology companies, but it was mostly in plumbing. It was things like data storage and optical networking. I always said to myself that it’s not the widget that I’m passionate about, it’s the company building process. When it came time to build my own company, which I knew for a long time that I wanted to do, I was initially not focused on passion because I just assumed that the passion would come from the company building process, and so when I looked at the domain to focus on, I looked at market opportunity rather than passion. I think in hindsight, that was a big driver of my frustration, because I would look at one idea in clean tech and another idea in enterprise software. I thought, “Well, geez, I’m passionate about none of these things, but it doesn’t matter if I find the right market opportunity.”

During that process, I got so frustrated that I said, “I got to find a place to channel all this ambition while I’m figuring this out.” That’s when I started training for my first marathon and it ended up being really fortuitous because during that training, it was an 18-week program that I followed and I used a bunch of the existing tools that were out there as far as the GPS-tracking watch and the chip that goes in your shoe from the big sneaker company and these online websites and communities and all these different things. It started out as two different conversations where one conversation was, “What about this idea? What about that idea?” The other conversation was, “Man, as a user, I’m personally frustrated with this fragmented experience on having as I prepare for this race. This could be done so much better.” It took me a while.

October of 2007 is when I ran that race. Going into early 2008 was when I really started looking more into this concept of combining my two loves, fitness and technology, and specifically starting around the sport of running where I had really gotten to know the existing tools and was very frustrated with my experience and had personal pain in an area that I was really passionate about. That was a big epiphany for me that I could combine my love for company building with a domain that I was also passionate about and happened to be a very big, very fragmented market that was being disrupted, or would be disrupted, by a bunch of innovation and technology that was coming in the years to come.

I was ready then to just jump and go figure this out because I said, “I want to make my living at the intersection of fitness and technology. I believe strongly in this space and there’s enough opportunity here and I’m passionate enough about it that I can see through the ups and the downs. My hypothesis is that this area of tracking is one that is fragmented and ripe for innovation. If I’m wrong, number one, if I fail gloriously and this goes nowhere, I’ll be a failed entrepreneur, but at least I’ll finally be an entrepreneur. Number two, fitness and technology, there’s so much opportunity that as I’m failing, I’ll really get to know what else is going on and I can pivot into something bigger and better and I’ve got a long enough runway to take a reasonable shot at figuring this out.”

May of 2008, I left my job because I was sitting, I was in a very demanding profession. I was working basically from dawn till dusk and it was all-consuming. I was sitting here with this idea that I couldn’t stop thinking about and it was like, “Wait a minute. You’ve been waiting for the last five years to either find a team to go find something to do with or an idea that you’re so passionate about. The idea finally comes and you’re going to sit nights and weekends in coffee shops and chip away at it? Get out there and attack this thing.” That’s what I did.

Andrew: How’d you know it would be a big enough market? You said when you were looking for opportunities, when you were looking for that startup, you wanted to find a market that was big enough and you knew that you’d be passionate enough to build a company you cared about but you wanted that big market. How’d you know this would be a big enough market? I don’t see enough people running out there. I see more people at McDonald’s than I see out on the street running. The people who are running, I don’t know if they’re so athletic, they’re so concerned with their time, that they’re even wearing the GPS watches or that little pod that stinks that you attach to your shoe.

Jason: Right. Made by the terrific apparel and footwear company.

Andrew: Quick sidetrack here, Olivia wore that to the marathon here in Buenos Aires in Argentina. She trained with it, she trained with it, she trained with it. She was so proud of how fast she was going to be. She got to the marathon and she realized that it was completely off. Completely off. That little pod, because it comes from a brand-name company, it’s Nike, we think that it’s perfect. It sticks. That’s why I’m a little bit frustrated with it. That’s why I kept expressing that. Going back to the business at hand here. How did you know the market would be big enough?

Jason: That was a very timely anecdote because I too was a Nike+ user when I was training for my first marathon which was Chicago 2007. It was the one where it was over 90 degrees. They canceled the race halfway through. I finished before they canceled it, but I digress. I was using the Nike+ system as I ran for this race and I didn’t think that it stinks. I actually thought that they were incredibly forward thinking and that they were really onto something.

What they showed was if you take a sensor and put it on an athlete while they’re doing their physical activities and you feed that data back to a system online where you can keep that data over time and you can bake in social accountability and game mechanics and analytics and coaching and all these things to make this solitary, lonely activity that you do more game-like, more fun, get more insight, get more coaching to drive ongoing improvements, that was incredibly powerful. You could see by the way people responded, and sure it was a generation-one system in the sense that it was a pedometer and it required separate hardware and you need a certain pair of shoes and it’s only for one sport. In my head, it was like, “Wait a minute. If something that is doing these things is getting people so excited, why is it only for one pair of shoes with one technology for one sport offered by a company that’s core business has nothing to do with fitness technology? Why doesn’t someone carve that out and build this as an independent fitness technology company that does this across all different data types, all different devices, so it shouldn’t matter if you use a certain pair of shoes or need a certain technology? No matter what you use to collect this data, you can participate in this independent system and it’s across all data types in broader health and fitness and all sports.”

Nike was actually the biggest data point that I had that there was a massive market here because look at the success they were having in this very narrow focus. For us, when we left to do this, we were exclusively running focused and we are exclusively running focused. One interesting note is we are going to be running focused indefinitely. We’ve got so much to do in running; it’s a very big market. When we incorporated the company in June of 2008, the product was RunKeeper and the company was officially incorporated as FitnessKeeper Inc. The reason is that this was never just about the sport of running. We are going to make sure that we build a system that does this right for the sport of running, but ultimately, there’s no reason why the kinds of things we’re doing, the concepts we’re putting in, couldn’t be applied to, not only other sports, cycling, hiking, walking, skiing, weight lifting, but even other areas of health and fitness, your weight, the food that you eat, how you sleep at night, your heart rate.

When I think about the vision that we’ve got, we do ultimately want to build this virtual layer that makes the world healthier regardless of what they’re doing to make that happen and give them more accountability, give them more access to their data, give them more coaching, give them this fun and game mechanics and all the things that are going to get them off their butt and stay off their butt. We happen to think that’s a big idea and in order to ultimately get to that big thing, we’ve got to do that really right in one place and so we are very tunnel-visioned, narrowly focused on nailing it for the sport of running for the indefinite future.

Andrew: You got a fan in the audience. Corey Clark saying that Nike+ has nothing on RunKeeper. You said “we” when talking about the launch. It was just you at first, or was there someone else with you?

Jason: That’s also an interesting story. When I left my job, it was just me at the time and I was aggressively talking to everybody in the local community, both trying to figure out what skills you need to build a web service, because I had never built one before, never done any product management, never been a developer, never done any front-end design, never started a company, never done anything consumer, so there were a bunch of firsts here. Like anything else, it’s not scary to do it, it’s just a question of getting that knowledge. The best way to get that knowledge is to talk to as many people as you can that have done it.

That’s what I did and along the way, not only did I learn the different skills that are required, but I also learned how to assess to has those skills and I also got to know a whole lot of the people that had those skills during that process. I had no outside funding. I did have a decent-sized personal runway, but every dollar that I put in out of my pocket to get the company started was a dollar less of personal runway. That two years was going to shrink really quickly. I talked to a bunch of web development firms that said, “Hey, we can get this website launched for you. It will cost you 50 to 70k to get your first prototype built.” If I was putting that kind of money in, the sand in my hourglass was going to run out [interference].

Once we uncovered what was happening with smartphones, that was a really big epiphany because we looked at how powerful these mobile devices were getting and how many things were consolidating on these mobile devices. Things like a camera or an mp3 player or all these things that you used to have go out and buy an expensive standalone device. Increasingly, these smartphones were good enough that you don’t need to have to go out to get that separate device. We looked at fitness tracking and we said, “These devices are all going to have GPS in them going forward. Why don’t we do the same thing with smartphones in fitness tracking and enable people to use their phone to do this fitness tracking so they don’t need a separate GPS watch?”

We were especially excited about the iPhone, both with the App Store model that we. . . May of 2008, I left, the App Store launched July 12th, if that frames things from a timing standpoint. We were really excited about the iPhone both because of the App Store, but also because Nike+ had already gotten people used to running with their iPod and the iPhone had the iPod built in. We went around town and said, “We’re going to build this iPhone application that enables fitness tracking.” Everyone said the same thing, “No one’s going to run with their phone.”

Andrew: Who’s “we” by the way who’s running around doing this?

Jason: I found three guys who said, because the initial concept was I’m going to build a web service and it’s going to integrate with any different input to collect this data. If you have a Garmin watch, if you have a Polar heart rate monitor, if you manually input your data on the web, no matter what you do, you can participate in this independent fitness system. That’s what I set out to build when I quit my job.

Andrew: I see. First, it was going to be a web app that integrated all these different inputs. Okay.

Jason: Yep. It actually still is, but we’ve been very selective with starting with smartphones as the first two inputs into the system, the iPhone and the Android. I was setting out to build that and I found three guys who said, “We can build this for you nights and weekends. We all work together in our day job. We did a project together two years ago and we had a blast, for our day job. It went so well but then we all got pulled into different projects and this could be a way to get the band back together nights and weekends and do something really fun.” I said, “Well, geez, it’s only been a few weeks since I left my job and I already have three guys telling me that they’ll build this nights and weekends for equity. I won’t even have to use my precious capital at this point. This is terrific. But, I already quit my job. My personal runway is tanking, and what I really need is a co-founder. It’s great to have this option, it’s a lot better than nothing, but I don’t know if I can hitch my wagon to a team of moonlighters. Hey, guys, this is awesome, I love this. This is way better than not having this discussion. Hold this thought, I got to keep talking to a few more people.”

The very next people I talked to said, “Hey, we can build this website, but have you thought about doing an iPhone application?” This was a small, two-person development shop. I hadn’t thought about building an iPhone application, but immediately when they said it, I said, “We have to do this. This is incredible. This is awesome. This has to happen.” This was late May, early June of 2008. The App Store was launching in July. If my memory serves me, they had just gotten one of a very handful of developer licenses from Apple and they hadn’t built their first iPhone app yet. They agreed to cut their price drastically to get their first iPhone app built and basically get someone to pay for their development curve. I got to get started on a product for orders of magnitude less because number one, they wanted to do it, but also it was a much smaller development effort than a big web service. I engaged those guys, paid them out of my pocket cash. Went back to the moonlighters and said, “Hey. Guess what? I’m ready. Let’s rock and roll. By the way, everything we talked about is the same as far as the vision of what we’re building except we’re also going to plug in this iPhone application.” They all said, “Why do you want to do that? That’s stupid.” I was persistent. I said, “Trust me. This is going to be so big. This is incredible. This is where things are going.” I just knew. They were on board with it at that point. They came around really quickly. I like to tease them that they didn’t, but they did. We were off and running.

All of a sudden, I’ve got three nights-and-weekends moonlighters and a small development shop with two people, so five people besides me working on this, meeting several times a week and using very little capital and we’re off. We’re off to the races. That’s the “we,” three moonlighters and a two-person development shop.

All of a sudden, I’ve got backing now, I’ve got five people behind me. I’m going around town saying, “Look what we’re going to build.” Everyone said, “No one’s going to run with their phone.” I said, “Well, geez, this is interesting. This phone that everyone says is too big to run with, granted it’s bigger than these little, tiny GPS watches, but it’s actually no bigger than the iPod two generations before that that everybody ran with, the big white brick.” It’s just a perception thing because more is law. Everything keeps getting smaller and lighter and faster and longer battery life. This is just the beginning of the smartphone revolution, so yeah, it might be big now for some people, but over time, the phone keeps getting smaller, the GPS gets more accurate, the battery life gets longer, and we’re already seeing this if you look at the Android devices and now the iPhone 4 that’s coming out or that’s out. That device is orders of magnitude more powerful than the 3G that we started with in July of 2008. The other thing is that the phones are just the first two inputs into this system. Ultimately, we’ll integrate with a Garmin watch. We’ll integrate with, I mean, we already do integrate with manual mapping on the web.

These are the things in my head was let’s start with a smartphone, it’s the shiny thing in the room that everyone wants to talk about. It’s where things are going. It’s immediate revenue because we can charge for these things and not only that, if we point the data from these smartphones back to this community, this community we set out to build from the beginning, if I want to get my data off of that smartphone app that I’m using, there’s only one place to do it. As far as raising awareness around this web community, if we didn’t have that app, it would have been search engine optimization or Google Ads or who knows how to build initial awareness when you start from nothing.

With us, we had tons of press before we even launched because everyone wanted to talk about iPhone applications and then anyone that used our iPhone app could also use our website. We were off to the races there, but the funny thing was that all anyone talked about for the last two years was this great iPhone application. In my head, we’ve gone around town, we’ve started on some panels and things because we’ve got Time Magazine Top 10 iPhone app of 2009 and over two million users and all these accolades, this big passionate growing global community. It’s been teriffic what we’ve done. In our head, this was always this big, disruptive system that we’re building where it’s the iPhone’s the first input device that gets the data into the system, but it’s the social experience we’ve enabled, the analytics we put in, the coaching we put in, the game mechanics we put in, the community features, the sharing, all the things that really drive, improve physical behavior over time. That’s what RunKeeper’s about.

We haven’t spent a lot of time out talking about that stuff because if everyone wants to think we’re just this little iPhone app, that’s fine because it just gives us room to run. Everyone says mobile applications are a lifestyle business and you can’t make any money on apps. To be honest, the app downloads have been very powerful from a seed funding standpoint to enable us to focus on building great product and managing community without having to worry about going out and burning a lot of cycles raising cash to keep the lights on. They’re not even in our business plan. If you look at our big picture, the one-time download is just not that interesting. We think what is interesting is the fact that more than half the people that have ever bought our pro application in two and a half years are still active on a monthly basis.

Andrew: Really? For something like this, half the people who paid for the pro version are still using it?

Jason: 54%.

Andrew: Wow. Most people give up on the gym membership February, March, for sure by summer, they’re done. Let me ask you a few questions here. Let me jump in here. First of all, I’m wondering how much, roughly, did it cost you to build that iPhone app?

Jason: The initial release?

Andrew: The initial release.

Jason: Ten grand.

Andrew: Ten grand to get that first version out? Okay. It costs 10 bucks to download it right?

Jason: It does, but keep in mind, we’ve had dozens and dozens of releases since then and that the RunKeeper system that the iPhone app users are experiencing, isn’t just the app, it’s the integrated web service. You can’t put a price on the. . . I forget the number, I wish I knew it off the top of my head. The lines of code that are in the RunKeeper system as this point in two and a half years was a number that blew me away.

Andrew: Just a little bit of math here. How many people have downloaded the paid version?

Jason: Out of more than two million users, we’ve got, it’s double-digit percentage, low double-digit percentage that have converted to pro.

Andrew: Minimum 10%, 200,000 people.

Jason: Yeah. . .

Andrew: 200,000 people at 10 bucks a pop, two million in revenue. That’s what we’re saying when we say that you were seed funded by your customers.

Jason: I heard a stat the other day that said that the number one app in the app store does about five million dollars. Five million a year, except it’s a one-time download so it’s not really five million a year. It does five million. Everyone says, “If the number one app in the App Store does $5 million, how can you build a big business around smartphones?” For us, we’ve consistently been in the top 100 in gross revenues in the whole App Store, 300,000 applications. The numbers we do are significant for an early-stage company as far as that revenue that’s been coming in. We want to build a billion-dollar company. We want to change the way people engage with their health and with all forms of physical activity, ultimately. To get there, there’s no way that those downloads are going to get it done for us, but the powerful thing about smartphones is less about the download revenue that it creates and more about these unbelievable integrated systems that can be built and that are truly transformational as far as what it enables people to do themselves, whether they’re out and around using location-based technology or on the web with this frictionless data input that comes. . .

Andrew: I’m sorry to interrupt. I just want to ask one more question about the financials and if you feel uncomfortable saying it, then don’t reveal anything. I’ve been getting a lot of flack lately from the audience for being too pushy or too persistent with the financial questions. How much are you comfortable saying that you’ve generated in revenue from the paid app?

Jason: If you look at that number one, if the number one app in the App Store does five million and we’re in the top 200, it’s safe to say that we’re lower than that and more than six digits.

Andrew: More than six digits, lower than five million you’re saying?

Jason: I will say that that’s only one revenue stream for the company. We’ve got RunKeeper Elite which is our web subscription service, purely optional. It’s $5 a month or $20 a year. We only put it in place a few months ago and we’ve got many thousands of users are now paying us on a monthly basis. Over time, we’re big believers in freemium. We’re big believers in building a system that brings tremendous value to everybody for free and then giving them, showering them with so much value, and giving them a taste of what’s possible that they want more and more and more and then giving them a bunch of other stuff optional for paid. We never want them to feel like their arms are being twisted to go and pay us.

In fact, if a user is going to be free for a lifetime value, we actually see tremendous value in that free userbase, because we’re building a lifestyle brand and to us, that userbase is the best sales and marketing that we could possibly have. A rabidly passionate userbase, regardless of whether they’re paying us or not, those are our best friends. Our plan is to always keep all the users, including the free users, very happy, but to give the advanced users, the ones that want to get at all these, the coolest stuff, the ability to get those things if they want to. If they’re going to pay us a few bucks here and there to get access to those things, what we found from the users who have been paying us so far is that they don’t mind. In fact, if anything, they’re the ones that are riding us to get down this development road map faster because they see as well as we see how much potential this system has and how little of it we scratch the surface of.

Andrew: I’m sorry to interrupt again. The only reason that I keep interrupting and I know the audience, again, keeps getting on me for interrupting too much in the interview, but I have to because there’s so much that I want to ask you about. It’s hard to squeeze it all in. The next thing I want to ask you about is management. Did I just lose the video? No, I didn’t. Okay. Management. When you hire a dev team, how do you make sure that they produce what you need when you’re not one of the developers who’s part of the team? Then I want to also ask you about how do you manage moonlighters, guys who have other things going on besides your project?

Jason: We’ve got. . . Go ahead. Finish your question.

Andrew: Let’s start off with the dev team. How do you manage a dev team?

Jason: First of all, we have no moonlighters anymore. There’s nine of us on the core team and we are actively growing. As I mentioned, we’re not living large by any stretch of the imagination. In fact, we’re obsessively frugal, but we have managed to put a sustaining structure in place that’s enabled us to be ramen profitable, so that we can continue to aggressively grow and stay lean as we power through. The moonlighters, the biggest thing when we did have moonlighters was a misconception that people had around town was, “How did you find people that are willing to work for free?” I didn’t look at it that way at all. In my mind, althought we weren’t cash rich, our equity was the most valuable currency that we have. I fundamentally believed from the beginning, even when we had nothing, that this was going to be a humungous, world-changing company. I still believe that.

The people that we brought on as the initial moonlighters were not people that are used to making $200 an hour as a contractor and I’m talking them into forgoing their contractor rate for equity. These were people that were sick of contracting and sick of punching the clock and wanted to make meaning but didn’t have the personal means to go salary free like I did because they hadn’t planned for it like I had or for whatever reason. These were people that were itching to go and be co-founders and although they were moonlighters, from the beginning, they acted the part. These guys, our CTO, he was working north of 40 hours a week with a day job and still stayed in very good standing with his day job.

Andrew: Because of this, because of this passion that we’re seeing in the interview right here, because you believe this is going to be a billion-dollar company, not a lifestyle, small app that sells for 10 bucks and everyone’s excited that you sold a few hundred thousand of it, you see something way bigger than what people are excited about now and you just kept evangelizing it to the people who were working for you so that even though they had other jobs, they felt your passion.

Jason: From the beginning, the thing, to this day, I’m absolutely most proud about, and there’s a lot that I’m proud about so far, I can’t see the stream, but I’m hoping there are some RunKeeper users that are watching this right now, but the userbase that we have in the community is absolutely incredible. I’m tremendously proud of that. Even prouder of the internal culture of this team. If you look at this team, across the board, everyone is enormously talented at whatever their core responsibilities are, but each of them, on the sneak, also bring all these other skills and they’re strong personalities, the timing as right as far as where they are in their lives and the risk profile that they have. They also really fundamentally believe in their gut in what we’re doing and how we’re going about it.

One of the things, I don’t know if it was luck or intentional or what, but one of the things we’ve been able to foster here is that we’ve got a process for how we roll things out that, it’s very user-driven with the feedback, but it also goes through this internal assembly line where it’s basically taking a slab of beef and putting it in front of a bunch of pitbulls and these guys go and bang heads but what ends up coming out, you’ve got all these healthy tensions and checks and balances, and the final product that comes out, it just works time and time again. We’ve got this system down so that we feel so confident that as long as we know what our big picture is and we continue to put one foot in front of the other that we are going to get there because we feel like we may have a small team and limited resources, but that we execute better than anybody.

Andrew: How much management was involved with the dev shop? Or did you just say, “This is what I need,” and they figured it out?

Jason: That’s an interesting question because I think there’s definitely a different dynamic on the core team versus a vendor. We actually had a very strong partnership with that dev shop for a long time. We’re actually, as of several months ago, we don’t work with them any longer but they did a really good job for us and played an important role in getting this company. . .

Andrew: There’s a big risk in hiring a dev shop. You’ll see the companies that investment, or seed funds, like Y Combinator, aren’t going to fund an entrepreneur whose core development is done by a dev shop. You’ll talk to, and I’ve talked to lots of entrepreneurs who aren’t developers who hired dev shops who they trusted with the product and then they ended up getting bupkiss. They ended up having to spend a lot of money for something that didn’t work. For you, it worked so beautifully, that for $10, you can get an app that actually works, that people can download and get a sense of what you’re doing and even use and enjoy. How did you do it? That’s what I got to find out. Did you just luck out that you found the right guys?

Jason: No. What it came down to was the core team, the people that started moonlighters that are now co-founders. . .

Andrew: I see. The friends who are moonlighters, who co-founders, were helping you manage them.

Jason: On my left, actually, the way I lay it out in my head, this is funny, but it’s this. . . My background’s recruiting, sales, business development, got my MBA, people, people, people. I’m all the way on the left, the runner, the product visionary, the guy that beats his chest all day long. All the way on the right, the first guy to come in was this muscle technologist who doesn’t just write a ton of code but can also take a step back and think about architecture and strategy and scalability and he’s just been phenomenal. If it were just him and I, what would end up happening is that I would go and support the users, because I did all the customer service support until recently, I would go and support the users and get all this feedback, throw it over the fence to him, and one at a time, he would just go and build everything, one after the other after the other. That doesn’t scale.

A really key hire, or it’s not a hire because he came in from very early, but an incredible skillset to add to the mix was a product guy. Here’s a guy that was trained as a developer but who moved into more product and product management after several years of writing software code. He sits right in the middle where he can work with me on the business side, on strategy and modeling and things like that, but he also, as all this feedback is coming in from the users, he’s a filter that says, “Okay. Here’s the product plan. Here’s the road map. Here’s the order we’re going to do things. Here’s the things that make the road map. Here’s the things that don’t. Here’s the things that will make the road map someday, but we got to shove them for now because they’re not strategic.” Not only that, but for each of these things that are on the road map, here’s the blueprint for what they should be, how they should look.

Then we got a front end guy who’s making things pretty and usable and everything like that. By the time they get to that developer to build, now he’s managing several developers, everyone’s in concert. It’s not a handoff, it’s very collaborative. The reason it got done successfully with the vendor was because when that vendor got them, and we had some hiccups along the way, but we got it to the point where by the time it came time to bite off a project, it was, “Here’s the screenshots. Here’s every screen. Here’s every button. Here’s what we need. Here’s the flow. Here’s all the different use cases. Here’s the fringe scenarios we need to account for.” It was literally laid out on a platter so that they could just go and say, “Okay. We get it. We understand.” Even then we had weekly calls to make sure that through that development process, they didn’t work in a vacuum and there were no misaligned expectations.

Andrew: I see. All right. In many cases what happens is the person who’s hiring the dev shop will say, “This is what I need you to build, go do it,” without giving details and without understanding what they’re looking for as far as a blueprint. One other thing that you told me in the pre-interview is that you had a weekly meeting, I think it was, with the guys who were working with you.

Jason: At one point, it was me and seven moonlighters. I had been advised by everyone under the sun not to do that because you don’t want to hitch your wagon to a team of moonlighters because life gets in the way. Soccer practice or vacations or day job emergency or whatever it is. This project, to me, my livelihood, would always take second fiddle. It gets back to what we were saying before about choosing people that were in it for the right reasons. We met every week, sometimes twice a week, as a team over at MIT which is right down the street from me. We’re here in Boston. We acted like a team. We felt like a team. We felt like an in-the-trenches, early-stage startup, same excitement, same energy level, everyone just as excited as companies that had a more traditional startup structure with everybody living in the same house Silicon Valley style, working around the clock. We felt that way even though I was the only one in it full-time.

What happened was that, for us, as the model started working over time, one at a time, these people who had all been working together for over a year, getting a corporate culture, getting used to each other, getting that synergy and complementary skills, they ended up coming in one at a time, but it wasn’t some hire off the street. We were already a team before that even happened.

Andrew: How’d you keep them together on days when you weren’t in the same room? Was there Skype that you were using to chat with each other? Was there something else that you used to stay top of mind with them? Was it just email?

Jason: Politically, I should say that when they were on the clock for their other thing, we didn’t communicate at all. That’s my answer. I will say that there are a plethora of online tools out there, such as this. I feel like you’re sitting right across the table from me right now. Technology is such that, everybody’s local which has been huge because there are times when the only way to solve something is to get in a room and get in front of a whiteboard, otherwise, everyone’s just going to be popping blood vessels in their forehead. Those times come up and when they do, it’s a great luxury to be able to get in front of that whiteboard. Day to day, working just like this, whether it’s the instant message, or Skype, or phone, or email. We do all of those things and it works very well.

Even today, I saw that Netflix, I read an article on Netflix the other day and they have a vacation policy that is they have no vacation policy. Everyone they hire works really hard and when they get tired, they take a break. That’s how they work. There’s a huge amount of trust that comes into it. Philosophically, I love that. I love hiring people and surrounding myself with people that are truly passionate, ambitious, hard-working people that I get along with, we enjoy each other’s company, we respect each other professionally, and we share a common vision.

Andrew: Where do you get your energy? How does somebody get energy like that?

Jason: I do have a cup of coffee in the morning, once a day. Even if I didn’t have it. . . I think my parents asked that question too.

Andrew: Did you always have that even growing up? You were this kind of energized?

Jason: Yeah.

Andrew: Okay.

Jason: Some people get more mellow, I’m probably going the other way. I’ve been like this since I was a little kid.

Andrew: Let’s see what else I got here. I’ve got a note here to come back and ask you about a ton of press. How did you get so much press early on?

Jason: It was a combination of things. Being one of the first 200 applications on the iPhone, it was, if you didn’t get a ton of press as one of the first 200 apps on the iPhone, you’ve got bigger issues. Some of that was timing. Some of it was also the way we went about it. From the beginning, we tried to really build a product that people love and actively engage with our community and listen to them. We were pretty early on being a brand on places like Twitter and engaging with our community as that ran and speaking with a human voice and not corporate speak and just being regular people and being ourselves and being tranparent and accessible and approachable.

From the beginning, we had this community that immediately started forming around it. Some of it just came from our community out spreading the word and love and that helped plant seeds all over the place. Others of it was that, I can think of many times over the life of the company when we didn’t just blindly send canned. . . I’ve never done a press release. Never done a formal press release. We talked to the press like people. I can still remember the first time we got featured in TechCrunch. It was because I had corresponded with TechCrunch and they were sort of nibbling around and then they went quiet on us and it didn’t look like we were going to get featured and I sent the guy an email and I said, “Hey. I’m at your conference. I’d love to give you a demo.” He said, “Meet me in the back in five minutes.” I gave him a demo and week later, we were in TechCrunch and the New York Times. Dedicated article, front page of the New York Times’ Business section with a picture. Stuff like that.

We looked at people that had written about, when people like Nike had come out, when people like Garmin had come out and people that we knew, like Wired Magazine, or different writers that we knew were passionate about fitness technology and said, “Hey. I saw that you’ve written about the next big thing in fitness technology back in 2005. Well, I figured you should know about the next, next big thing in fitness technology. I’d love to share what we’re doing.” We were very targeted with who we approached. We tried to approach people who we felt like our message would resonate with. We talked to them like people and told our story. That seemed to work for us.

I will say that we’ve never hired a PR firm, we’ve never done a formal press release, and lately we haven’t even been spending any time on it because, like yesterday I found out that we. . . Jake, what did we get last week? What was the [??]? Oh yeah, we were one of the 49 best apps in, best mobile apps on any platform in PC Magazine yesterday. We’ve been doing no PR and the reason is that we’re so varied with the things we have coming on the product side that if we can just get this stuff out there, the community and the brand recognition we’re going to get just from this growing userbase is going to generate way more buzz than any PR could possibly do.

Andrew: What about the way that you ran? Can you tell people how you ran the marathon? That’s the first time that I ever saw a picture of you and got to know who you were.

Jason: Yeah. That actually was a big one for us. Two Boston Marathons ago, about three weeks before the race, I had been asked, I went to high school with a professor at Emerson College locally, who teaches a social media class, which I thought was pretty cool, pretty forward thinking on Emerson’s part to even have a social media class. He put me with a group of six students and we were their client for the semester and their goal was to do a marketing campaign with us. It was very loosy goosy, undefined. It was up to us and the class to figure out what to do. We were brainstorming with the class and they said, “Let’s do something around the Boston Marathon,” which was three weeks away. I said, “Well, okay, but what?” Someone said jokingly, I think, “You can run the marathon dressed as an iPhone.” Immediately, it was we have to do this because if we’re. . .

A lot of it comes back to gut just like we say no to everything, we’re laser focused, then we find something we love and put all our eggs into it. It’s just how we work. It was that moment where it was like, “We have to do this, whatever it takes.” Number one, iPhone was the hottest thing in town. I guess this was April 2009. Number two, we were big on humanizing the brand. On Twitter, it was the catchword of the day where we don’t just talk about features and product, we talk about making fun of each other or cool things that we read, running the pouring rain this morning, or whatever it is. We try to engage with the community and talk to them like people. What better way to humanize the brand than to literally run as a giant version of us? We did that.

I had done no training for the race. I didn’t have a number so I didn’t know if I would be able to officially run the race. We just started scrambling. We found, as we got down the path quickly, that there was a lot of drama. If we were going to invest in this and put all our eggs into doing this marathon campaign, what if I don’t get a number? What if we don’t find a costume? What if I’m not trained enough? What if my injury comes back in my heel which was starting to act up? There was all this drama and it was like, “Wait a minute. Why don’t we film the process of pulling this campaign together so that if I don’t make it to the starting line, we can at least pull people behind the scenes of this crazy group of college kids pulling together for a little marketing campaign for a startup?” That’s content. We did that and we launched this series of teaser videos leading up to the race that filmed all these crazy kids running around, having a blast, pulling together this marketing campaign.

On race day, by the time I got to the race, I woke up the morning of the race, again, the second time we were in the New York Times, dedicated article, talking about this crazy RunKeeper running the Boston Marathon dressed as an iPhone. It got a bunch of traditional media, a bunch of print media, a bunch of, it was on all the tech blogs and even cooler was with social media, as I was running, the Twittersphere was going bananas. When I finished the race, because I was tweeting during the race, we were tracking it with RunKeeper and I was taking photos. In fact, Apple hadn’t enabled backgrounding yet, so I had to have two iPhones with me, one to do the tracking and one to take pictures. When I got done, the picture of me crossing the finish line, within 10 minutes, had been viewed like 800 times. Then there was a following campaign which was, “Look at the success these college kids had with a gorilla marketing campaign and got Superbowl caliber ad exposure for free.” That was covered in Adweek and PR Week and all these other places. It was a big hit.

Andrew: Does the iPhone battery last for the full marathon while it’s doing GPS?

Jason: Yeah, at the time I was using a 3G device, so you had to do a few tricks. You had to use the top button to sleep the screen so the screen didn’t stay on and if you turned 3G off, you get a little more juice from it, and if you turn the music off. It did make it through and it tracked beautifully. I actually still have that route on my profile on The new phones that are coming out, even the iPhone 4 has a much longer battery life than that. What you’ll see, as each of the subsequent devices come out, the GPS keeps getting more accurate, the battery life keeps getting longer, the phones keep smaller and more. . .

Andrew: I could run a marathon, when I get my iPhone 4, I could run a full marathon, listen to a podcast or listen to several podcasts throughout the marathon and not have the battery drain?

Jason: Shouldn’t be an issue.

Andrew: Oh, all right. Assuming I’m fast enough. Virality. Was there any virality built into the app that helped you spread it?

Jason: It’s funny because it’s been two and a half years now and we’ve literally spent, our resources have been so precious that we made a conscious decision to block out partnerships, block out distribution, no race presence, no advertising. Everything was just about building a product that people love, making it social to use, so that just by using it, it spreads, and then managing and supporting our existing community. That’s all we’ve done. We’re actually starting to turn a corner where we’re going to start to do a lot more interesting things.

To date, we’ve been an extremely obsessively product-focused company. Little stuff like autosharing to Facebook and Twitter has been absolutely enormous for us. The reason is, from the user’s standpoint, if I know before I head out on my run that my run’s going to be automatically shared on my Facebook profile, I am going to push myself to run harder and to have a faster pace and finish strong because the world is watching. It’s the same phenomenon as if you’re actually running in a race and you have all the crowd on the sidelines that are pushing you to go harder, or if you have a personal trainer at your side that’s keeping you motivated. Just that little social accountability is a very powerful scene.

From a growth standpoint, the clickthroughs on those, on places like Facebook, are off the charts because that’s interesting content to your friends when they see wow, you just did a 20 miler in the pouring rain. I’d like to see that. They look at it, but not only are they seeing the race you did and commenting on it and encouraging you, but it’s also much more powerful than a banner ad or flashing lights because that’s not us saying, “Hey, look how great we are.” It’s an implicit endorsement of someone saying, “This is my running tool of choice.” That word of mouth has really gotten put, and it’s a cliche, but it’s gotten put on steroids with all these electronic tools to spread this stuff and it’s the reason why companies like Zynga have grown so quickly with these social games.

Andrew: Do you have a percent of clickthrough rates on that or do you know what the clickthrough rates are on that?

Jason: I don’t offhand, but I know that we had more inbound traffic from people clicking on shared Facebook runs last month than we did from people searching on Google.

Andrew: Ah, wow. I see Charlie E. in the audience is saying he’d love to work in an environment like this. Danno [SP] agrees with the reasoning on how to get the app spread. AndrewSG posted a link, I guess, of you at the marathon in the costume. All right. I think that’s all my questions here. Let me say this, by the way. One of the reasons why this was such a good interview is because you’re connection is incredible. I feel like I can see you like a human being, we can actually have a conversation. I love it. What kind of connection are you on? I got to tell everyone else to have that connection.

Jason: I don’t want to give away the fact that I was a liberal arts undergrad and technically illiterate. We are on an Internet connection.

Andrew: Oh, this is so interesting. Really? You don’t even know what kind of connection we have, but you’re still able to lead the development of this incredible product, both the Android app, the iPhone app, and the website, because of the people that you have there?

Jason: We have got an absolutely incredible team. I feel very fortunate about the people I get to work with every day.

Andrew: Speaking of your team, who’s Jake? I saw him CCed on the email where you and I were introduced and I saw him in the audience here.

Jason: Jake, I had a real difficult problem which was. . . For the last two and a half years, as CEO and founder of the company, I also, my job title should have really been customer support because it was about literally 70% and plus that my time was spent supporting and managing the community, whether it be on Twitter, on the Facebook fan page, through emails, in the support forum. As our community has grown, it’s taken up more and more of my time and it’s been harder and harder to do it adequately at the same time that my other responsibilities have also grown now that, as a company, we’re doing so many other things.

It was definitely going to stunt our growth if we didn’t, basically, get in someone to hand over the reins and take over that community management, but at the same time, it’s been such a big differentiator for us that I couldn’t just hand it over to anyone because it had to be someone who had the same personality and voice to the users, who was also passionate about fitness, who was a user of our product. There were a number of things that it had to be. Also, you didn’t want someone who was a career customer support person, we wanted someone who had ambitions to take over the world who was going to come in doing this critically important thing for the company, but then over time, do more and more for us.

Jake Cacciapaglia, who is about 20 feet to my right and probably bright red right now, he came on a few months ago and it’s been a god send because I couldn’t imagine turning over the reins to really anyone, but I knew that it had to happen and I haven’t had any issues dumping more than he can handle on his plate. I’m always just dumping things over and it’s not a dump because I can do it with the confidence that it’s going to get done well. Every hire we’ve done in the last few months has been a critical one, especially for such a small team. Getting someone like Jake in has been a tremendous asset for us.

Andrew: AndrewSG in the audience brought up an issue I should have brought up here, the design. Beautiful, stunning. By the way, Jake, if you’re listening to us now, come on camera, let’s say hello to you.

Jason: Hey, Jake. Come here.

Andrew: The design, who did it?

Jason: [claps] Yay. Jake Cacciapaglia.

Andrew: [laughs] He doesn’t want to do it, huh?

Jason: Oh, he’ll be here.

Andrew: Oh, there he is. All right. He’s coming out. Hey, Jake.

Jake Cacciapaglia: Hey, guys.

Andrew: Dude, that was kind of cool that you jumped right in there. The other company that did that was Balsamiq. Suddenly I get Peldi from Balsamiq doing the interview, he had someone from his company in the audience, answering questions, and dealing with people one on one. It’s such a cool thing for you to do.

Jake: Everywhere where the community is.

Andrew: Cool. Are you a runner, too?

Jake: Absolutely. Yeah.

Andrew: How often do you run?

Jake: Sometimes six days a week.

Andrew: Six days a week. Morning?

Jake: I’m probably overtraining at this point.

Andrew: Donnie in the audience is saying you’re a sick runner. Apparently you do train a lot.

Jake: [laughs]

Jason: Actually, you know how they say that you should hire people that are smater than you? I actually did an even tougher thing, which was hire someone that’s a better athlete than me.

Jake: So it’s not true.

Jason: I enjoyed being the fastest one on the team for a little while, but I have lost that distinction.

Andrew: Oh, so you’re out running in the marathons?

Jake: Not yet.

Andrew: Not yet.

Jake: We’ll see.

Jason: He’s humble.

Andrew: I got to say this, too. It’s not part of the focus of this interview, or of any of my work here at Mixergy, but I got to evangelize running. There’s nothing like running, for not just getting you in shape physically, but mentally. When you’re at your worst moments, you go out for a run, when you hit that three mile point, don’t you get into a place where everything just becomes clearer and you’re looking at life in a more optimistic way?

Jason: I don’t know what I would do without the sport of running, honestly. It’s stress relief, it’s therapy, it holds my body together physically, it gives me time to think about big, important problems and get a fresh perspective, the endorphins when you do a big run, there’s nothing like it. I’m biased of course, but it’s been a big part of my life for a long time before RunKeeper.

Jake: It’s a constant adrenaline rush working at RunKeeper. You got to find outlets. Running is definitely something that is a necessary outlet for me.

Jason: Never a dull moment is definitely a term that we hold dear to our heart.

Andrew: I see people in the audience are telling me they’d love to work there too.

Jake: Thanks a lot, Andrew.

Andrew: Bye. I’ll see you online. You know what the other great thing about running is? You can do it anywhere. You don’t have to wait for the gym to be open. You don’t have to get special equipment flown in. I love cycling, but I’d have to bring my bike into different cities if I wanted to bike through them the way that I like doing it. Running, I just bring my sneakers, any pants, any shirt, and I just go out there and run. I’ve run in Buenos Aires. I ran in California, in Paris, wherever I am. Love it. I love it. I can’t stop talking enough about it. I should. Let’s go back to the design because that is the focus of this interview. How’d you get the design to be so freaking beautiful?

Jason: We got lucky. It’s going to seem, pretty soon, like a lovefest when I talk up different people on the team, but we have absolutely incredible designer. Perfect example, when I was talking before about each person on the team bringing so much more to the table than just their core thing, this guy, he was a musician, he is a musician. He went to Berklee, undergrad, Berklee School of Music here in Boston. He DJs, he plays a bunch of intramural sports, but he fell into design and he’s entirely self-taught. He doesn’t have any of the big, fancy training but he’s incredible.

Andrew: He’s one of the guys who was moonlighting with you at first?

Jason: Yep.

Andrew: How do you do it? How do you get all these people around you? If we don’t leave people with an understanding of that, I think we’ve missed a big portion of this story.

Jason: I honestly, I think part of it is that I see so clearly what can be and in my mind, it isn’t about coaxing people to join in, it’s really just about letting them behind the curtain to see what I see. I think that’s how they view it, too, where we’re all in this together and we fundamentally believe what we’re doing will have the potential to change the world in a significant, disruptive way for the better. All of us are really excited about the opportunity to be a part of something like that. Part of it is the people, that we all like each other. Part of it is that we’re all mission driven and we’re chasing the same mission and we believe strongly in it. Part of it is that it’s not just that we like each other and we want to hang out with each other, but there’s a tremendous professional respect amongst the team for each other’s capabilities and also there’s the right mix of skills where we’re not too top heavy, we’re not too development. . .

Andrew: How did you know that Tom would be a good designer for this and not just a musician who was dabbling in design? How’d you know he could give you the right look?

Jason: A big piece of that comes back to the benefit of, there is actually a benefit of starting in a moonlighting capacity which is, you can get people in, throw them together and let them get to know each other, and it’s like a try before you buy. By the time he stepped in, if he didn’t step in, we joke with him that one of us would have gotten his hands and the other would have gotten his feet, because it was just so obvious that he needed to be here. I honestly feel that about every single person on this team. We’ve met a lot of people. Even when we’re not hiring, I spend time talking to people all day long because we know, over time, if we go and do all the things we plan on doing, we’re going to need a ton of people and the best people.

Andrew: Were there people early on who you were thinking of working with or maybe started working with but it didn’t fit just right?

Jason: Not really. There’s only been one instance of that so far and it was less about skillset and more about timing. It was somebody who had a bunch of kids and kids in college and a big mortgage and different things going on and I think just adding this environment. . . This is a very exciting environment, but it’s also not for the faint-hearted. It’s demanding and it’s stressful and I think from a timing standpoint, it just didn’t make sense to add this to the portfolio of things that were on his plate.

Andrew: I’m sorry to just get so deeply into the trenches on this, but I’m just wondering how you end up with such good people. Did you look at their portfolios before you started working with them? Did you work with all these guys before, at a past company? Was there any experience before you hired them or before they came on board as moonlighters even that let you say, “Yeah, they’re probably going to be right for me. We’ll work together for a little bit and if it does work out, then we’ll work together full-time”? Was there anything before then that let you know?

Jason: I’d done a bunch of functional roles in venture-backed companies and most recently, I spent two years at a boutique retained executive search firm working with tier one venture capitalists to hire CEOs to run the companies they invest in. Assessing talent is something that I’ve done for a long time. That’s a piece of it. A piece of it is that the guys we have are very high caliber and they’re the kind of people that when they go some place and they leave, people follow. That’s also happened. I’m sorry and happy to say.

I think the other piece of it, and I don’t want to get cheesy philosophical here, but karma’s been on our side. We’ve really tried to do the right thing from the beginning and for whatever reason, everything’s felt like destiny for us thus far. Tom’s a perfect example. He used to work with our CTO’s girlfriend at a company and then we met with three different people and all of them, besides her, said, “You should talk to Tom Boates. You should talk to Tom Boates. You should talk to Tom Boates.” They’re all people that we trust and respect. When we finally got to Tom Boates, it’s was like, “Look. I’ve never met you before but I feel like I’ve known you for a long, long time.”

Two of our other guys, our product guy worked at a company and they were like his bash brothers, the guys that go and do the hardcore development for the projects that he manages. He’s known them for years and worked with them in a professional capacity. You can basically go right down the line. We didn’t know everyone in advance, but we also, almost without exception, the people we brought in, if I’m iffy on someone, I don’t have to say anything to anybody and each of them come out of there with the same feeling. If I’m like, “Man, we have to have this person,” it’s also tended to resonate across the board without. . . It’s not that they see my reaction and feel like, “Oh, well I better feel that way too.” I honestly think that we’d pass the Pepsi challenge. I would be interested to do that test, no preconceived notions or guidance, then you don’t know if it’s up or down and what do you think?

Part of it is that we meticulously crafted. Part of it is just dumb luck. I think that, too. I don’t take it for granted. If we shed this team and we all had to go our separate ways, I don’t know, I’d like to think we could rebuild a team like this because we know how to do it, but it just may never happen again. I told each of these guys that this is not a transaction. They’re not being brought in to make this company successful. I said, “If this company’s financially successful and then I go to do something again and you guys say, ‘Hm. Should we go with him? No. I wouldn’t do it with him again,’ then this company was not a success.”

Andrew: All right. This is a great place to leave it. Let me just add a couple of notes to the end of this interview. One, first an apology, then a note of thanks. The apology goes to the transcribers who, if you guys want to get paid twice as much for transcribing this interview, shoot me an email because you deserve at least twice as much because I know it’s more than twice as many words per minute.

The second thing I got to say is I got to thank Court [SP] over at Scavenger. I had someone from Scavenger scheduled to do an interview today 15 minutes before he was on a flight. He couldn’t make the interview. Court, instead of saying, “Hey, Andrew. Things happen. There’s rain coming down somewhere, the plane can’t get off the ground, I don’t know what is going on.” Instead of saying, “Andrew, go figure it out,” he said, “Let me introduce you to a guy who I think you should meet who can cover and come in last minute.” Thank you to Court from Scavenger.

Thank you Jason for coming in last minute like this and doing this interview. You didn’t know 15, 20 minutes before we did this interview that you were going to come on here and I’m so grateful to you for coming on and being such a great guest.

Jason: Thanks, Andrew. It’s really been a pleasure to be here. Sorry about the words per minute. Thank you to Court as well for making the introduction and giving us the opportunity. We’ve been fans of what you’ve been up to for a while and I’m honored to have been a part of it.

Andrew: Thank you very much. I cannot wait to be back in the U.S. in less than two weeks to get RunKeeper working again. I don’t have GPS on my iPhone down here, but I cannot wait to get back into it.

Jason: Less than two weeks, that’s going to give us some time to put out some pretty significant improvements as well. Good timing.

Andrew: Awesome. All right. Thank you. Thank you all for watching. Bye.

Jason: Thanks, Andrew.

Andrew: Cool.

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