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James Gill

by Josh Pigford. Last updated on February 07, 2024


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This week I chat with James Gill, Founder of GoSquared, which offers real-time web analytics, among other things. James has been working on GoSquared for over 10 years…starting the company when he was a wee lad at the age of 15. In this episode we talk building analytics companies, the role of design, expanding your product outside of your initial idea, the benefits of “real time” analytics and so much more. Enjoy!

Josh: Just to kick things off, you guys in the past, it’s probably been 6, 7 months now, but GoSquared turned 10.

James: GoSquared did turn 10, yes. That is correct.

Josh: Which is a lifetime in Internet years. You’ve just been working on GoSquared for 10 years, right?

James: Basically, yeah. Yeah. There’s a long story there. I think we’re simultaneously one of the oldest startups, while also being one of the youngest teams, I think. It’s a weird combination, and it all basically means that we had nothing better to do when we were like 14 and have kept something going that long somehow.

Josh: You guys started GoSquared when you and your co-founders were what, 14, 15, something like that?

James: Yeah, yeah. If we want to jump into that.

Josh: Let’s jump in.

James: Essentially, GoSquared started as a complete random project when I was in school with my two co-founders, Jeff and JT. We saw this guy build a website called the Million Dollar Homepage. I don’t know if you ever came across that.

Josh: Yes, yes.

James: It was a beautiful homepage of a million uniquely colored pixels.

Josh: The gaudiest looking thing.

James: Yeah. We saw this, and we just thought “Wow, this guy can make a million dollars from a page like that,” and we just thought if that guy can do it with a page like that, surely it can’t be that hard. At the time, I knew nothing about the Web or web design, and my two friends, Jeff and JT, they were super smart, but the Internet was just this complete unknown thing. We just thought wouldn’t it be cool to try and build a website and see what happens? Yeah, we basically started this site with, and instead of selling pixels for a dollar each, we sold squares. That was what got us together, GoSquared. You’d buy a square on our homepage. The intention was to make a million dollars in a matter of days. Of course, that totally happened as 14 year old incredibly [spoiled 00:03:22] kids. No, we didn’t make a million dollars. It was amazing there because it got us together building stuff and it was just really, really fun. It was a good laugh.

Josh: How did you make the transition from selling squares on a page to analytics?

James: We started this and we found that no one knew about what we were doing. We just thought “Oh, we’ll build this thing and everyone will flog to us” and that was absolutely not what happened. Through one way or another, we ended up starting a blog. We started a blog which started getting people to the site and it was mostly focused on design. From that, we started making lots of connections in the design community, and from that, lots of other design-related sites and blogs wanted to put these square ad placements on their websites. We started turning this project from being just a homepage with a bunch of square ads on it to being more of an ad network, and so people started putting these ad placements on their sites. From that, we then started giving them more and more information about those ad placements.

Then, from that, most of the feedback was “Hey, I’m not selling any of these ads and I’m not making any money from this, but I sure love this control panel you give me to see how much my ad traffic is getting and how much traffic my site’s getting.” Basically, we heard this so many times, we felt like why are we bothering with this hassle of selling ads? There’s a few other small players in the space like, I know Google Ads and others that we’re up against. Why don’t we try and just see what we can do by, instead of trying to be this middleman selling ads all the time, what if we just sold the control panel, this analytics view, directly to some of the people that want it? I remember this was probably in one of the last years while we were at secondary school. We just thought, let’s go for it.

We made this quite tough decision to stop working on trying to sell ads, and we shifted all of our focus to trying to sell an analytics product. Essentially, at the time, it was really, really simple, but it just showed you a list of users or a list of businesses who were on your website. It was just amazing because everyone before that seemed like a dump of data from their web logs and web traffic and all these things looked awful. They were greyscale and updated every night. It was just horrible, whereas this was all JavaScript-based trackers so you could see the device and all of the information you needed about businesses. It just felt really human. It was just, until that point from what we could see, most analytics tools had been treating visitors and users as just numbers and just data points. We really wanted to make it clearer that there’s people on your website. Yeah, that was how we got into it, and ever since then GoSquared’s been a very different, non-square related venture.

Josh: When you guys actually started selling the analytics product, was that 2007 or something?

James: No, I think it was later. Later than that.

Josh: It as 2008 or 9?

James: 2009, maybe. I think mostly it kicked off when we made … The tool, at the time, we called it LiveStats. It was quite a catchy name. It was just a list of your businesses online. I think, because we had had the blog going, we had been putting out a lot of design content, and Smashing Magazine kept tweeting out some of our stuff. Just by chance, they tweeted out our marketing page for LiveStats and it just suddenly sent a ton of people to the site, and a large portion of them actually wanted to sign up for what we were doing. It took us off guard, because until that point, it had been really tough getting anyone to want to sign up.

Suddenly, Jeff and JT, who are my co-founders but are also the engineers of the three of us, they were like, “Oh man, what are we going to do? We’ve got this one shared server. There’s no way we’re going to scale for this.” Suddenly, we had some good problems, like we can’t keep up with demand rather than no one knows who we are. It was an exciting time and it kind of made us think maybe we’re on the right track with what we’re doing.

Josh: At that point, Google had acquired Urchin.

James: Yes. You are an informed man.

Josh: I was building stuff then too, so I remember using Urchin, and then Google acquiring it, all that stuff. This would have been a couple years after that. At that point, though, would that have been your main competition in the analytics space or was there something else? was there a thing called AW Stats?

James: Yeah, AW Stats. There was a webalyzer as well, I think. They were always bundled with your web hosting, and they were somewhere.

Josh: You’d have to hit up cPanel.

James: Yeah, exactly. Always some panel somewhere. I bet there’s so many people listening to this podcast right now thinking “What the hell is all this? This is nonsense.” Yeah, that was what it was like back then. The graphs were not interactive at all. They were all images. It was horrible.

Josh: Everything’s shoved in a thousand tables deep of all sorts of just gross stuff.

James: We never set out to try and build something that tried to compete with Google Analytics in a way, because what we were always doing was much more individual, visitor-based, and it was much more of a focus on who are the people on your site? Google had always seemed to be much more of an aggregate level thing and showing graphs and charts, whereas we would try to show you much more like, “Hey look, there’s 50 people online right now and there’s normally only 10 people online. Look at all these people. Some of them are on your pricing page. Why don’t you go and try to talk to them and chat with them?” We always saw ourselves sitting in this weird space. It was not quite analytics, but we always found it hard to know what to call it, really.

Certainly, as things evolved, I distinctly remember, we were actually in San Francisco for a week just meeting some friends because we’re normally ever in London, and we were talking to some people. We were actually talking to some investors and we met some other people and they were like, “Oh, what’s it like now that Google’s released their real time view?” Oh my God, what the hell? This same week, so much had happened. Yeah, basically Google rolled out their real time view. It does some of the job for some people, but certainly that space has changed so much. It’s gone from being no one really cared at all about web analytics back when we kicked things off in 2007ish, 2006, back in those days. It’s gone from being something no one really cared about to being an incredibly hot space. It’s been fun keeping up and seeing how everyone’s taken different angles on this.

I think one of the challenges we’ve always had is there’s so many different angles you can take on trying to help a business understand what the hell’s going on with their website or their web application. You can look at that in a million different ways. A lot of it is about just being opinionated and trying to make things as simple and as obvious to people. I think one of the things we’ve always tried to differentiate on is being easier and simpler than everything else that’s out there, and that real time differentiator that used to exist is more of an assumed factor now. Even though it’s still definitely a big part of what makes us special, but what we really try and go for now is just simplicity. We take care of it. You don’t have to worry.

Josh: On the real time thing, what do you guys see as the big benefit of having real time versus historical views of things?

James: I think they should be using combination, but I think one of the factors we find is just incredibly engaging to have the team always seeing the pulse of what’s happening. For instance, this week put up a couple of blog posts and they’ve been driving way more traffic to the site than usual. There’s just this real energy among the team to see that happening in real time, unfolding in front of your eyes. It’s almost like watching the news as it’s happening. I think, especially for a product team, often the feedback maybe is at the end of the week or the end of the month, whereas to see things happening instantly, it really gives a buzz that motivates the whole team, I think.

That’s one part of it, and then also we often use it to pick up on new things as they’re happening, so it might be that someone else has written a blog post about us, or someone’s mentioned us on social media. They may not necessarily have at-mentioned us, and you can immediately see traffic coming in from that tweet or that URL and just engage when it’s actually relevant. It’s so different to be jumping on something the moment it’s happened compared to 24 hours later. There’s a lot of benefits there, and also in terms of what you can do under the hood with APIs, if you, for instance, know your top 10 support docs in real time, then reflecting that to your end users in real time is also a really powerful thing. It might be that everyone’s suddenly having an issue with a new feature you brought out. You want that help doc that they’re all going to to be the number one thing that people see. Yeah, there’s a lot of really handy things you can do when you have that information up to the second, instant.

Josh: How do you avoid, us is sort of also in the financial analytics side of things, how do you avoid analyzing all the things? There’s this urge to “We can throw a graph on that.”

James: Yeah, analysis paralysis.

Josh: Right, and how do you guys make the decision to not just pile on the graphs, basically?

James: There’s two factors to that. There’s one, us internally as a team knowing what to measure, which is I see one side of the answer to that. There’s also us building a product for other people and deciding what other people need. I think that the product, it’s always come down to trying to understand our customers as best we can, and understanding what they want from the product and trying to make sure we push it forward in a way that makes sense for them, because I think if you don’t have a clear enough idea of who you’re surveying or why you matter to them, then it is really hard to make these calls. Whereas I really believe, often the most opinionated products are the best.

If you decide you want to be focused on a small but fast-growing SaaS businesses, that takes a lot of decisions off the table in terms of you don’t need all these publishing-related metrics or you don’t need all these e-commerce related metrics. You want to be focusing. I think that’s exactly what Baremetrics, actually, has done fantastically well. Baremetrics may not be terribly helpful if you’re trying to sell canoes at your Shopify store, but it’s not meant for you, and there’s probably other tools out there that are great for you. If you’re running a Saas business, you definitely care about MRI. You definitely care about the numbers you see on the biometrics dashboard. Thinking as deeply as we can about the reasons we’re being used and the people that are using us, that helps us focus that in the product.

Then, internally, we track a lot of stuff. We track so many different metrics and numbers, but we’re very cautious of making sure we only talk or discuss as a team on a regular basis a selection. Those mostly relate to the overall funnel of the business, and that’s how well are we doing at attracting new people to the site, what’s our site traffic, what’s our conversion to trial, how many trials, is that going up, hopefully yes, and then conversion to becoming a paying customer. Then more the financial metrics like you guys report, so what’s the average MRR of a new customer coming on board? What’s our overall MRR like? How’s it going up? How’s it going down? That can sum up the entire business, really, at a higher level.

I think what we’ve tried over time is to get those numbers as tight and as nailed down as possible, so that every week we can actually compare back to the previous week or the previous month or the previous quarter with consistent numbers that always report in the same way, whereas there’s a lot of other numbers that are changing all the time. More product-focused things. Often you might be seeing if a new feature you rolled out last week is getting the reaction you thought it would, and that’s going to be a much more … Most of the product changes we do, the metrics change quite frequently as well, so it’s a bit harder to compare on a longer term timescale with how many people click the Upload button on this screen, that kind of stuff.

Josh: You guys have transitioned, certainly not away from, but you’ve added some additional stuff on top of the analytics space. Live chats, to me, seems like the biggest jump away from being …

James: A big step, yes.

Josh: What was the impetus for doing that at all?

James: I’d say maybe 2 years ago, we made this big step from being just a web analytics offering. We used to just have this web analytics dashboard, and we decided the web is just a part of what businesses actually have now. A lot of people have a website, they have an application, they have an iOS app, an Android app. We introduced a product about a year and a half ago called People, GoSquared People. It was essentially a cross between an analytics tool and a CRM, and it was all about having one definitive place to understand your users, understand your customers. We built that primarily out of our own needs, because every time someone would get in touch with us or one of our customers would be talking to us, we would be looking data up in about 10 different tools. We’d have a help desk, we’d have a user system, we’d have some hacky MySQL front end thing, we’d have a billing system and no biometrics at the time.

We’d have all these different tools, and it would be like, “Who the hell is this Ben guy?” Ben is 5 different people in 5 different tools. The primary purpose of building the People product was to have a definitive understanding of who Ben was, who each of our users and customers were. From that, what we really believed was if we can do that, if we can have that definitive understanding of the customer there, then that will enable us to do a heck of a lot more in terms of how we communicate with users, how we talk to them, how we treat them, how we interact with them. As soon as you got that data in one place, the logical next step is all right, I can see all that, but I really want to do stuff with that.

That led us down the route of working on all sorts of different ways of taking action. We started with integrating with a bunch of different tools, and we built WebHooks and APIs to hook into things like MailChimp and all sorts of tools like that. The more and more we did that, we were just talking to customers as much as we possibly could and really, the thing that came from it was these integrations are great, but it’s such a pain still switching between all these tools. It would be so much better if it was just all in one place. That was what led us down to doing live chat.

Live chat was actually something we had hacked around with and experimented even back in the days when we were building out the original stuff we were doing with LiveStats, because we had always had this view of individual visitors. At the time, we pushed you off to Olark to go and chat with a visitor when he wanted to talk to someone. That was okay, but given that we’ve always been trying to build something that’s simple and easy and really nice and friendly, it always seemed crazy that we were doing so much complex analysis and data stuff, and then we would often push you off to another tool to do the valuable bit, which was the action. It just made sense. If we’re already doing so much hard work, why don’t we start doing more of the actual really valuable work bit, which is the taking action bit.

Yeah, it’s taking us down a very different path than what we’ve been on in the past, but from what we’ve seen, it’s working out great. Our customers seems to be really liking it and the feedback we’re getting is really cool. To be really helping people in their daily jobs, it’s so much more exciting to know that there are people that come into the office every day and they sit down and they use GoSquared to get their job done. In the past, that’s always been sort of true because they’ve relied on our metrics, but not it’s like they’re literally logging in at the start of the day and they’re inside the tool all day. It’s an honor, and it’s something we do take very seriously.

Josh: There’s almost been these stages of web tools where so much historically has been really reactive, where you take a look at things, you process all the analytics and you make decisions to do things in the future, but there’s so much. Because the Web has gotten so personal, you almost have to be able to take action on this stuff as soon as possible, and you can. It’s better to be able to react based on a set of criteria and react right then instead of a week later, sending a survey or something like that. You might as well take care of it right then, and then you can aggregate the responses and all that kind of stuff.

James: Yeah. It just seems like, when you look at the space like so many companies still treat their customers so badly. They make it so hard to talk to their customers, and the way they talk to their customers is such an impersonal messy way. Most customers don’t enjoy dealing with the businesses they actually do business with. It just seems like there’s such an utter lack of innovation there, especially as you get up to bigger and bigger companies. It just seems like there’s so much opportunity to improve there. It’s a crowded market in terms of offering a live chat solution, but we certainly don’t view ourselves as just offering this set of features.

We really believe that there’s so much opportunity to improve. We’ve always been trying to improve the way businesses understand their customers, but I think more and more it’s becoming how businesses just interact with their customers. I just think that market is phenomenally huge, and if you can take just a small bite out of that. It’s really nice being able to say you improved not only the businesses that you do business with, but also the customers of those businesses as well. I think we’ve been trying to do that.

Josh: Changing subjects a little bit here, do you still do a bunch of the design stuff on GoSquared? I know you did early on.

James: We have had various designers on the team. We have had a fantastic designer called Ed who’s been on the team for about a year, but he, unfortunately, is still at university, and he’s just had to go back and complete his final year of uni. He was doing a bit of design, a bit of iOS engineering as well. Yeah, it’s always been a bit of me and a bit of Ed and in previous times we had other people. I probably would be shamed in front of the CEO convention for saying this, but I still do a lot of the design work on GoSquared. It’s something I absolutely love doing. I feel like it’s one of my strengths and I really enjoy it, but I know there will soon come a day where I need to step back much more on that.

It’s been important, because design’s just so important in everything we do and it isn’t just “What is this button going to look like?” It’s really, as you know Josh, choosing what to work on, choosing what really deserves to be in the product, cutting the stuff that doesn’t deserve to be there. Design decisions come into so much of what being a CEO actually entails anyway. I’m guilty of still doing quite a lot of design.

Josh: To me, I would think people that are designers or engineers a lot of times start off. It’s the whole maker versus manager conversation. I think as long as you can balance the two … I think there’s marketing-heavy CEOs, there’s product-heavy CEOs. I would say both of us are probably product-heavy. We tend to look towards the product itself as a way to move a business along.

James: Absolutely, yeah. It’s such a huge opportunity. Often, there’s this discussion of oh, is this a product task? Is it a marketing task? Is it a sales task? I think product impacts all of that. The product is integral. There are so many changes that we made to [pass 00:28:19] the product that had a massive impact on marketing and sales. There’s just such a blurring between those different disciplines, in my opinion. A lot of the best marketing stuff is really product related.

What you guys are going, some of the stuff like the off the shelf calculator thing, you’ve got to work on product stuff that draws people in. I think that’s certainly how I view it. I don’t view it as in isolation. While the best product doesn’t always win, I think it’s so hard to win without a fantastic product that really, really solves some problems.

Josh: The product stuff, you can use the product as marketing, right? You guys that have those public OS uptake stuff.

James: Oh, the global metric. I literally just working on that for tomorrow’s, maybe not, the Sierra and the iOS 10 announcements, which Apple definitely won’t release because they’re so secretive. Yeah, just about to put those out. That’s a perfect example, yeah.

Josh: That’s like a mini product.

James: Yeah, totally.

Josh: That stuff works really well from a marketing standpoint and it’s got a much longer shelf life.

James: This is the thing. That kind of content just keeps on giving because the number of blogs and new sites that link back to that, we just build that one thing and ensure it stays up and is reliable and just keeps on giving back and giving back. We get a ton of traffic from that. I wouldn’t say it’s always the most focused and highest quality traffic. It certainly helps to get our name out there more. There’s often an element of serendipity in someone may see it and then see another blog post we do at another point and then gradually realize, “Ah, this is the right thing for me.” Those graphs are really helpful content.

Funnily enough, one of the pieces of content that performs the best in terms of driving traffic to us but not in terms of sending us customers is back in 2007, we made these icon sets. Some of them made the front page of back in the day, and they still account for … They are often the top trafficked pages on our entire site. It’s unbelievable.

Josh: These free icons.

James: Free icons, yeah. You get a lot of people that want free icons coming along, and sometimes you’ve got to say “You’re not the right people for our product.”

Josh: I think when you’ve got a product like that where, depending on the stage of the business, the size of the business, the designer or the developer a lot of times influences what gets used.

James: Absolutely. The number of times we’ve had creative agencies, web design agencies that come along for those icons or the cheat sheets that we made or things like that and they end up coming back for more resources and more resources. “Actually, we do need analytics. We do need chat. We need some of the stuff that goes with building as a product, because our clients would love it or we would love it,” and so, yeah. I think with content, I was talking to the theme a bit about this this week, but I really think you’re doing it wrong if you’re only looking at how many businesses came today? How many of them signed up for trial? How many of them became customers?

The returns of doing that content just build up over months and years, I think. It’s compounding over time. It’s about building a name people trust, and I think that is so hard to measure, but I’m convinced that it’s worthwhile.

Josh: A lot of times, people look for these quick wins on the marketing stuff, and the reality is it takes a lot of time.

James: You guys are machines on that. With the Baremetrics blog and you got your open startups and your Twitter account. Your Medium and you have your blog. I don’t know how you manage to churn out so much.

Josh: It’s the only thing I do.

James: Other than this podcast.

Josh: The podcast is a part of it, right? The unofficial goal is to put out a piece of content every day of the week. In some form or fashion.

James: I was inspired by reading, I think, Hitten Shah put out a piece and he referenced something [Hopspot 00:33:16] was companies that have over 16 blog posts a month get about 3 times as much traffic as those who only put out 5. I was like, “I’m going to see if that’s true or not.” The team just laughed at me. They’re like, “You are not going to survive if you do that.” I know you’ve been asking me a lot of questions, Josh. Forgive me for asking you one. I was going to say you have the Baremetrics blog with your fantastic posts and images. I was going to ask, though, something that’s been in my head. You have Medium as well. How do you decide between those two? I know this is getting a bit deep on the subject of content marketing, but how do you decide what goes on Medium, what goes in the blog? Have you found differences between the two, because we haven’t got anything on Medium right now, and I’m just wondering should we?

Josh: There’s a mixture of stuff. We started reposting older blog content on Medium, a lot of times slightly updated, but there’s certainly been some original stuff that we’ll post. It’s sort of a gut reaction thing. A lot of times what’ll happen is I’ll tweetstorm something, and so that’ll be 30 or 40 different tweets. Then I’ll condense that into an article or at least organize it into an article. I would say the Medium stuff almost works better for the more personal stuff. The thing that’s done the best for me as far as something I’ve posted was when I posted something about when a VC sent me an email asking about how we were only doing X MRR. That made a lot more sense to post there. The Baremetrics blog, I try to keep it a lot more actionable. Like, here’s what we’ve done, here’s what we’re doing.

James: How to do a video …

Josh: How to kind of stuff, whereas Medium tends to be more of just stream of consciousness kind of stuff.

James: That makes a lot of sense.

Josh: I don’t know. I’m still torn on having content in all sorts of places. I read Gary Vaynerchuk’s Ask Gary V book. I read it a few months back, and he is hardcore about posting stuff on all sorts of places in what he would call the native format.

James: Replicating, duplicating it.

Josh: It’s duplicating it, but it’s also not trying to funnel everything through a single source. We do these startup tip videos, these little 30- to 60-second little videos. I post those and I’ll upload it to Twitter, so it shows it as Twitter instead of just a YouTube link. Same with Facebook. I think the idea is that those tend to get surfaced more by those platforms when they’re posted in the platform’s medium. I have no idea. We may end up, in a year trialing, just bringing it all back into the Baremetrics blog.

James: It seems like a lot of people have been moving to Medium as their primary blog. I’m not sure why.

Josh: I’m not totally sold on it.

James: I like my GoSquared stats.

Josh: Having an email list really has paid off for us, and it’s so much easier to collect the emails on a blog. From a business team perspective, what size is your team right now?

James: We are 10 full time at the moment.

Josh: Are you all in the UK?

James: We are. We’re all in one little room in this office. Yeah, we’re not hashtag remote at all.

Josh: Is keeping everybody in the same place, was that intentional? You wanted to build…

James: I just thought it would be more affordable to have everyone in London, in the center of London. Anyone who knows London, it’s not the cheapest place to have a team right now. We originally were remote when we were doing this at school. we were all working from our own wherever, like Jeff’s shed or whatever. I think when we came to London, we were working out of a co-working space and we just started to build the team up from there, but I think we’ve certainly found it easier building a team in one place to just have everyone aligned. We have a stand up every morning, and everyone shares what they’re working on. We have a roundup at the end of the week. Crack some beers open, celebrate what everyone’s managed to ship in the week. I think that’s worked really well for building a strong culture within the team. I know everyone talks about culture and it’s like “Ugh.”

I think if there’s one thing I’m really proud of at the moment with GoSquared, it’s having an incredibly passionate, very hard working team that they’re just obsessed with making sure we build really great quality stuff and get it in front of customers as fast as we possibly can. That’s been really tough to do. In the early days, we really struggled with this, and I think part of it is being in the same place, making sure we’re all aligned. It’s so hard to get 10 people aligned doing something and we’ve learned through many, many mistakes and difficult times how it can go wrong and how easy it is to get 3 people thinking something completely different to another 3 people or 2 people working on the same thing in different ways for the wrong reasons.

There’s just so many things that go wrong as soon as you increase the number of people. I swear there’s some sort of name for it, but when you have all of the dots in a ring and you draw lines between all the different possible connections between all the dots. Every single additional dot adds however many lines. It gets so, so much harder, and I think at the moment we just found the best thing is everyone in the same place, everyone working to vaguely similar overlapping schedules, and it just helps so much with just keeping everyone aligned and together.

Josh: To me, we’ve got a remote team, but there are certainly days that I wish we were all in the same place.

James: Yeah. I hold my hands up because I know this is unsexy to say. It’s difficult as well because you read a lot of good stuff out there of how it works for GitHub or how it works for Buffer, and I just think every team, every company has different ways of doing things. It would be a pretty boring world if everyone was the same, but yeah. I really believe this is the best thing for us at this stage. It may not always be that way, but right now, it certainly helps add some certainty to the day of everyone will be in, vaguely across these hours, in the same place. It’s much easier just to have chats and communication. Everyone has lunch to get as well. It’s really nice. We just hear about everyone’s extremely exciting weekend.

Josh: Whenever we have team retreats …

James: Yeah, they look really fun.

Josh: As a team, that’s everybody’s favorite time because we get to actually hang out, and all our conversations aren’t just work related. It’s hard to pull off the watercooler chat kind of stuff that creates the basis of a relationship when you’re just doing it all over Slack. Sort of wrapping it up, but whats the biggest — this could be a business thing or a product thing — hurdle for you guys? What’s the hardest problem you’re trying to solve at the moment?

James: That is a good question. To pick just one. I think at the moment it’s a pretty critical point for us. I feel really, really excited about where we’re going in product, and I would happily talk all day about product an design and engineering. I think on the sales side of things, it’s a big debate right now. Do we really, seriously, go after larger customers and go after annual contracts to have more of an outbound approach and start having some phone conversations and things like that? We’ve traditionally always been this very inbound marketing self-service kind of business, and it’s worked tremendously well for us to build up the company to this point.

Certainly, what we’re finding is that where we’re going with the product, with the business, there’s a lot of education to be done with bigger customers that don’t necessarily buy into the way we see the future, and you can’t self-service your way into some of these customers. You need to educate. You need to sit down and help implement often. I guess that’s a big debate right now. Can we, at our current size, do that and go outbound? Do we decide we don’t want to do that yet? Hold off and keep the self-service thing and just ramp that up more? If we do want to go outbound, does that mean hiring some more people on sales and marketing? If we do that, then what’s the knock on impact of that? Do we suddenly become Wolf of Wall Street style and everyone becomes greedy?

That’s, I guess, a big debate right now. Do we go more enterprise-y on sales? It’s tempting because you close these bigger contracts and you can massively change revenue by closing one deal. My concern as well is like you suddenly get into this situation where you become very dependent on a small number of large customers and that’s another really dangerous place to be.

Josh: You touched on the culture thing before. It changes that too because it goes from let’s serve lots of businesses to the enterprise thing just changes even how you do the product, right?

James: Yeah, absolutely. There’s so many things the enterprise needs. All this certification, all of the check boxes checked. We do have some large customers, and that worked nicely.

Josh: I think it’s scary to me, having a handful of really big customers.

James: Yeah, yeah. You get into this situation where you have the tail wagging the dog. There’s so many pros and cons. The solution is to have lots of big customers.

Josh: We have the same number of large customers as we do small.

James: Exactly.

Josh: Wrapping it up, how can people get in touch with you?

James: Sure. I’d like to try and keep it very simple. Basically, everything’s at GoSquared. That’s our Twitter handle. I’m on Twitter as JamesJGill, all one word. Yeah. That is me.

Josh: Right on, right on. That’s all I got, man. I appreciate you.

Josh Pigford

Josh is most famous as the founder of Baremetrics. However, long before Baremetrics and until today, Josh has been a maker, builder, and entrepreneur. His career set off in 2003 building a pair of link directories, ReallyDumbStuff and ReallyFunArcade. Before he sold those for profits, he had already started his next set of projects. As a design major, he began consulting on web design projects. That company eventually morphed into Sabotage Media, which has been the shell company for many of his projects since. Some of his biggest projects before Baremetrics were TrackThePack, Deck Foundry, PopSurvey, and Temper. The pain points he experienced as PopSurvey and Temper took off were the reason he created Baremetrics. Currently, he's dedicated to Maybe, the OS for your personal finances.