Jake is the President and Founder of 10up, a leading agency with more than 125 remote employees, designing and building great websites, apps, and tools for content creators, using open platforms like WordPress. Jake has been building with web tools for two decades, and his company serves clients like ESPN, Microsoft, and Adobe.
What Your Favorite Motivation or Business Book?
Can You List 3 to 5 Life Success or Leadership Principles?
– If you feel like everything is under control, you’re not moving fast enough.
– If you want to see something change, start by being / modeling the change you want. – Start by assuming positive intent.
– Great service comes from a genuine empathy and desire to help others succeed.
Here’s The Full Transcript Of Our Interview With Jake Goldman
Jonathan: Hi there folks. Welcome back to episode 228 of the WP-Tonic show. My co-host Kim is not joining us. She has gone back to Florida and found her house still standing. But she’s got a little bit of repair work to do. So she won’t be joining us this week. But I think you can understand that folks. I’ve got the great pleasure of a great guest coming back to the show. He’s one of my favorite WordPress people. That’s Jake Goldman, President and Founder of 10up. Like to quickly introduce yourself to the listeners Jake?
Jake: Sure. Thanks for those kind words. I’m always happy to come back on the show. As Jonathan mentioned, I’m the President and Founder of 10up. We’re a full-service shop focused on using open source tools like WordPress to build amazing websites and tools and apps for content creators. Started 10up about 6 years ago. Have spent about, geez, losing track of the time now, 15 years working in technology and web and different sort of web applications. Right now I focus most of my time as President of working with our team on everything from sort of business development and sales to account management to strategy on some interesting projects to sort of all the million hats you wear, even when you somehow have 125 people working with you, still manage to wear an awful lot of hats and manage to insert yourself in a lot of places where you feel like you can provide some leadership. I live relatively close to you near Sacremento, in the suburb of Sacremento. That’s probably all about people are interested in.
Jonathan: Oh, you’re a man of many hats. Let’s put it that way. So I’m the founder of WP-Tonic. We’re a maintenance support company. We help you with WooCommerce, Membership sites or literally anything that you need a trusted partner that’s part of the WordPress community. We’re your people. Jake, let’s start with a couple of 10up things that have been in the news. You recently acquired Lift. Basically, what were the faults about that and how’s it going?
Jake: Yeah. I think we’re still I think buzzing on cloud nine about that acquisition. That entire team, the four of them, all four of them that joined us, including their partners Brad and Chris as well as the two other members of their team that are joining us, a couple of Engineers, including a front-end Engineer, have all been fantastic. The goal of that acquisition was, there’s a few goals. The largest goal was, although I think we do fantastic and creative work at 10up, we saw a real opportunity to add more of that leadership to the team and strengthen our portfolio a little bit, be a little bit stronger in our ability to compete and tell stories and have the time to focus on doing outstanding design. I thought Brad, Brad Miller in particular from like a how to position pitch, tell a story about design and Chris Wallace from executing and leading and delivering on great design, were really powerful additions to our team. They have some great stories in their portfolio, including Emmy nominated work that I think really lifts up, no pun intended, our own portfolio. I also think that, sort of that was like one of the main goals of doing an acquisition. The other reality is, as we spend time with them and just got to know them as potential partners and people, we found remarkable overlap in sort of our vision, what it is we want to accomplish within the space, the kind of customers we work with, the kind of experience that we’re trying to create for customers. And so, I think you put the opportunity to grow 10up and this just feels like a natural place for two teams that are, to join up and work together rather than occasionally competing and bumping into each other in a different direction. So that was sort of the impetus in terms of how it’s going. It’s still relatively early to say, “3 years in we’ve, it’s been a clear return on investment kind of a thing”. It’s only been, I think, not even 3 months since we’ve done it.
But I would say so far all of the things that we were hoping for are panning out. The talent that was brought into the team, Anthony and Christain are incredibly natural fits to the rest of our production team doing great work. I love working with Brad on some of the deals that we’re pursuing. We’ve had some luck there. I think is Chris is just starting to make a real impact, at the beginning of making a real impact in a larger design team at 10up. Just even on small things like helping us with some of the brand work that we’re doing for ourselves and some of our own market has really had an impact. So all the right signals, all the right feels a few months in.
Jonathan: That’s great. Do you think in general there’s going to be a lot of companies in the WordPress area that are going to merge together in the next year, 18 months?
Jake: Yeah. It’s a good question. I’m always cautious when I’m bringing out my crystal ball.
Jonathan: I do have the occasional good one.
Jake: 12 months is a relatively flies by. I don’t know how much activity we’re going to see in 12 months. I do think when we look at, when you talk about the next few years in this space and sort of make it a little bit of a broader horizon, my instinct is yes, that I think we’ll see more of that. I think when you look at the way the space is maturing, when you look at sort of like, I think you can look at this space and I want to be cautious about overstating my case. But I think you at the space and to be bit generalistic say there was a real peak between 2010, 2011 and 2014, 2015 where WordPress sort of turned a corner in its capabilities as a CMS which at a sort of right time and right place in terms of some CMSs growing out of a large part of the market. And in absence of good solutions, let’s call it below WordPress, and really had a boom period where there was a lot of publications, a lot of sites that made a migration to WordPress, that looked at it differently, that chose to go a different direction in platform, that were redesigning around that. So there was a real boom period I think that I would call the sort of the 2010 to 2014, 2015. At the risk of sounding like a pessimist, I think we’re a little bit more pass the boom time. I don’t think we’re in a depression or anything like that. I think it’s a nice healthy stable economy. But I don’t think it’s boom economy in WordPress anymore. I think its really stabilized in large part as a market at least for where companies that would be of the size and shape with things like an acquisition or things like merging made sense. And so, I think when that happens in marketplaces what you see is a number of companies that were sort of able to all succeed and have a lot of growth and have a lot of success on the backs of the boom market, start to go into a period where it feels like for the market to be sustainable for the kind of busy that they’ve built, for the kind of teams that they’ve built, where things, like joining forces and combining resources, start to make a lot more sense.
So I think you combine the fact to sort of like I think the state of growth in WordPress, the maturity of some of the businesses in WordPress. I think frankly just the life the cycle of people like myself and other business owners in the space that have been in the space for a long time and are sort of thinking about what the next stage in evolution in their business is and their careers are just sort of at that place where many businesses, 5 to 10 year in, start to look at that next stage of life cycle in their companies. Long rambling story short, I think you put those ingredients together and my guess is yes, that there’ll be a lot of natural gravity pulling people toward looking more closely at those options.
Jonathan: Yeah. I was just thinking because I was listening to a great audio Podcast this week in StartUps. Jason was interviewing Tim O’Reilly, a very bright guy. And he’s got a book coming out in October. And he was talking about some of the key elements of the book. And he was talking about how technology sectors start off with a lot of players, a lot of different things happening, a lot of excitement and then they mature and they come together. A lot of the best, some of the, looking for the right word here, some of the excitement in that area dies down. The brightest people move on to other things. I’m not sure if we’ve really got to that stage with WordPress really. Because I think one of, being open source in a way, one of the amazing things about Matt was that he kind of diverts WordPress with open source and he’s managed to keep a lot of excitement in the area really. I think that’s one of the things that make him really an outstanding Entrepreneur and brilliant of WordPress. Would you agree with that?
Jake: Yeah. I think I would agree. There’s a few points in there I would agree with.
Jonathan: Only a few.
Jake: I think, so yes. I think it’s absolutely true to say that there are life cycles in technology where it’s more interesting, it’s exciting, things are changing, things are different. By some force of like the people that like excitement move on to things that are now the new exciting, right? And by virtue of the fact that I think there is just a natural, I think a clumsy word choice is burnout.
Jake: But I think maybe quite what I mean, it’s less burnout than it is just interest in new opportunities, is a natural thing that comes to Entrepreneurs. So I think if you look across the WordPress ecosystem, and I mean, I’m a boring guy that’s worked in the same space for a long time, but I think if you look out across the space, a lot of the Entrepreneurs that have exciting companies in our space and you have to ask yourself like, “They started these companies when they were, in many cases, younger than me, right?”. In some instances, right? Like in their early to mid-20s, in many cases, started their companies. They’ve now been doing this for, probably getting close to 10 years in many cases for these companies. And you have to sort of scratch your head and wonder like, “Do they want to do it for 40?”. If they don’t want to do it for 40, what does that look like? Do these companies go through transformations? It’s one thing for a company, I think, even of like 10up’s size, to talk about the transformation where leadership changes over time and is organic. It’s another thing when you look at some of these companies, I think, that are 30, 40, 50, 20 and you have to wonder what next stage looks like for these Entrepreneurs. And I think feeds into our discussion. As for as Matt goes, yeah. I agree. Hopefully, we’re going to get around to talking about things like Gutenberg. I do think as much as there is a, people may want to be resistant to changes that feel disruptive. I do think ensuring that WordPress has exciting opportunities around, things like being a headless CMS, as a new frontier and how to build on those kind of technologies. I do think shaking things up and saying, “Here’s a new way we’re going to look at handling how we create content in WordPress”. I do think those are very important ingredients for both the CMS itself to stay relevant and exciting. But also to make sure that people that are building with it don’t lose interest and get bored and feel like they’re just always building with the same technology, solving the same problems over and over for years.
Jonathan: That’s great. One more question and then we go for our break. ElasticPress. How’s that going? That sounded really really interesting what you and your team were doing around there.
Jake: Yeah. I’m really excited about what we’re doing with ElasticPress. It continues to be, I think, a leading solution for integrating, talk about new and exciting technologies integrating with Elastic search where I think NoSQL and Elastic search and other options like are one of the more exciting things going on in technology. Right now at I think to be able to pair that a hosted solution for people that it was a little bit inaccessible to an enterprise because of the technical barrier or that kind of blockade that’s from creating a really great user experience for some complex features. In many ways similar to like what Matt’s trying to do. It’s something like a jetpack. You kind of have to say, “Okay. Well, here’s the plugin. But here’s the 15 steps you have to understand and walk through to make it do X and Y”, which are the really compelling use cases. And just being able to say, “For a certain segment of the audience that doesn’t want to do that kind of configuration or just sign up and we’ll take care of it on the back end for you”, is compelling. If the product is doing well, we have a good set of customers including some people that have been introduced to the first time through the product, are only engaging with us through using that product. I’m cautious to say that everybody that are, where Elastic search technology is right now, what our ambitions in terms of customer experience are at 10 up, we’re not striving at a starting point of $300 a month. We’re striving for this to be a mass market where we want tens of thousands of WordPress users buying this plugin. This is very much a plugin for us. It’s targeted with a sustainable model for us. A relatively modest set of small to medium in enterprise businesses for whom this provides high value, which is to say, even with the few dozen customers we have now, it’s a very sustainable business because of the price point that we set it at and that’s very deliberate on our part.
I guess I say that to say like, when you think of some of the other people that are selling $100 a year plugins or something, it’s a very different model in terms of how we think about and judge success. But the key thing for me is it’s sustainable. The kind of customers we want to work with are being well served by it, having a good experience.
Jonathan: That’s great. Have there been any surprises? Anything to come up that you didn’t anticipate?
Jake: I don’t think anything shocking in the process. It’s fair to say, using the product internally for customers for over a year before we opened up to the audience, so I think most of the like, “Oh my gosh. We didn’t realize we have this kind of issue or that kind of issue”, we were prepared for in advance. I don’t know if it’s surprising to us. Something that may be interesting is that a lot of the interest we get from ElasticPress and that landing page often times doesn’t end up converting to somebody that wants a hosted solution from 10up. But ends up converting to people that are really interested in us helping solve challenges with Elastic search and they end up being Agency customers. So as interesting about how it’s positioned and how it’s marketed.
Jonathan: Oh, great.
Jake: I have no complaints about that.
Jonathan: That’s great news. I think we’ll go for our break folks. We’ll be back in a minute and we’ll continue the discussion with Jake. Really great stuff. Be back in a minute folks.
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Jonathan: We’re coming back. I’ve really enjoyed it. Hopefully, Jakes enjoying it. We’ve covered a few topics. I’ve gone on a wander, but I sometimes do that, don’t I? You’re used to it listeners.
Jake: Not doing any favors with my rambling.
Jonathan: You don’t ramble. I’m the one that rambles. You’re not a rambler. I can assure you. I’m notorious. But how my mind works. But if you can put up with it, it does go somewhere. Let’s go on to Gutenberg. A fascinating topic that’s been taking up a lot of bandwidth. A lot of interesting things said about it. A lot of not so interesting. What’s your take on how’s it going and how it was handled? How it’s been handled so far?
Jake: So I can share my sense of sort of Gutenberg in terms of its overall direction, in terms of how the UI is shaping up, in terms of what I think the project pertains for WordPress. I will confess before I state my case. I’m not personally very with like the politics of like how it’s been rolled out or sort of the inside of how it’s been . . .
Jonathan: Very wise.
Jake: I’ve got other things to focus on than politics. I do think starting it as a feature plugin is a smart way to go and giving people that exposure. But I don’t know if there are other nuances that are more about it. I am very excited for Gutenberg. I may be a little bit nervous about making sure that as a company we’re preparing customers for it the right way. I’m a little bit nervous about how we make sure it’s not disruptive, but actually useful and rolled out the right way to our customers so they have a great experience with it. But overall, I like seeing this kind of assertive, forceful change in the platform. We talked about it earlier. I think we need those kind of changes to stay relevant, to stay, for a lack of a better word, to stay sexy as a platform, to stay interesting as a platform. I think the most scary thing about WordPress to me, which I think I’ve said and even written about in the past, is staying stagnant, sort of falling into it works well don’t change it. There was a lot of those discussions happening around the time that things like auto-updates the platform where a lot of people, particularly on my side of the business from the enterprise space sort of pearl-clutching about, “You’re changing the nature of the software and this is scary and you can’t make this kind of a change”. I think I was even at that time a champion for it’s not going to be that bad. And by the way enterprises, it’s not hard for you as sophisticated people to turn off that feature. And we need this kind of thing to keep it interesting and relevant and tell a good story. And I don’t know of anybody that’s had an issue with it. In fact, if anything, I think people would miss it now if it was gone.
I know Gutenberg’s a much more significant leap than a turn on, turn off kind of like auto-updating, but I really look at what they’re doing and say, “This is what I want to demo to the next generation of customers. This is the kind of interfacing experience that people that are new to WordPress that are discovering it for the first time, up and be evaluating a platform, this is what I want them to see”. And by the way, I also want customers who might be thinking about the next generation of their platform, the next generation of their CMS, to see that the CMS they have is not getting stale, that it’s doing interesting things. Frankly, it presents a business opportunity for us to go and pitch or ways we can extend this for them and ways we can upgrade their platform. And on top of all of that, I think the basic framework of an interface that’s more built around modular blocks is absolutely where content creation in the CMS should be going as part of its direction. I do think, and I gave this talk about like content distribution and I’ll be giving a talk about content distribution at WordCamp Sacremento.
Jonathan: Oh, great.
Jake: Yeah. And one of the, spoiler alert, one of the premises of that talk is like I think what content editing and creation is, is going to increase in our industry fragment based on the part of your use case for the CMS. Which is to say, one of the premises of that talk is if you’re a journalist and you’re doing news publishing, I actually think writing your content will move entirely out of the CMS as an experience and the CMS will just be a management point for that content, not a creation point for the content. But I think when you think about people that are doing marketing kind of use cases, people that want to do more sophisticated content that’s not just a block of text with images and videos that’s going to be distributed to 15 different platforms. When you think about that very specific website marketing sophisticated content creation process, I think about things like different kind of blocks and modules. Like here are four other posts you might want to look at. Imagination’s the limit, right? Here an interactive element that I want to insert specific to my use case. Here’s a form element to sign up for a white paper that I want to insert in this place in my content. So I think that sort of step toward creation of pages and layouts is where the CMS has to move and the modularity of it to say, here are the kind of blocks that are relevant to this kind of customer. For a marketing customer, it could be a call to action, it could be a form you insert as a block element on a page, could be an email capture for a campaign. For a blogger, it might be different kinds of photo gallery presentations, might be if they do a lot of Podcast things, it’s a sound cloud. I do think that kind of step in that direction is where we should be going, is where we should be leading into.
Jake: I’m doing to rambling. But again, that module component part in particular where you can say, you can hypothetically say, these are the kind of blocks and modules that are relevant to this kind of customer in their writing use case and here are ones that are not relevant.
Jonathan: No. Thanks so much for that view. It’s opened my eyes to something new really. I could understand why this was happening because, not in the great outline you’ve just given us, it was more to do that Automatic is in competition. WordPress.com is in direct competition with Squarespace and Wix and half dozen other hosting solutions. And now obviously with WooCommerce, it’s directly going to get in competition with companies like Shopify. So I just thought that they would have to do something. But there’s a bigger picture as well, isn’t there? I think there were two factors on negative. I think negative’s even too strong. There were two slight worries that I had with the process was that one of the things that I thought was fundamental was that it was going break, possible break backward compatibility which has been a bedrock of the WordPress. The second thing is I thought there were problems with communication basically about this whole process which has got a lot better recently. Would you like to remark on both?
Jake: Maybe lightly again. I really have no clue about the communication side it. To me, there’s a phase where you’re experimenting where you want to be nimble or to be honest, I empathize as an Entrepreneur leader with being less interested in the politics of everybody feeling good about the communication as opposed to let’s focus on the product itself and building it. For many companies, that could have happened in a completely closed way. That could have been door closed, automatic projects plus maybe a few contributors. We’re going to build this thing out and we’re ready for a 1.0 to showcase where we think WordPress is going. And we’ll expose that and then do a lot of marketing and communication. The nature of WordPress is we build these things in the open, but they’re still not built in the open in terms of there’s a marketing campaign about what it is while we’re in that early building open source process. We’re still, to my understanding, probably at least 6 months, if not a year out, from the thing rolling out into WordPress as a platform. I think the time of getting to 1.0, 1.1, getting to the theory of the plugin and the concept and the prototype being at a place where is the time to start thinking more intentionally about what the marketing and the communications plan is. Now, if we have this conversation again, 4 months, 5 months before Gutenberg rolls out and I still feel like there’s a general lack of awareness and understanding that exists now, I will be the first to vocally say, “We have a problem here because we have a major change coming and nobody seems to have a clue what this is about”. But I think it’s a little too early to clutch our pearls about that. I think now is the time to really be starting that conversation and starting to broadcast what this is, not necessarily, again, preoccupying ourselves with it during the early and development process.
So that was the communication piece. The backwards compatibility piece. So my understanding is that for most modern best practice use cases, it’s going to be pretty backwards compatible. They’re not going to be major breaking issues. It’s certainly not going to be to my understanding in terms of how it’s actually stored in the CMS. It’s not going to be a case of you upgrade your site and your pages are broken. Again, I’m going to be a little bit cautious about, I have gone and upgraded 10 sites and seen what happens, so I’m going to be a little bit cautious about overstating my knowledge. That’s my understanding at least of the goal. There may be more messiness around when you actually go in to start editing your site, especially if people are still relying on things like shortcodes which the community has talked about for a while as not really being the right way. kind of hacky shortcut for a lot of solutions, but not a great way to solve the UI problem. I may be a bit on my mountaintop. I’m a little less fearful of the like we’re going to in one particular part of the CMS, we’re going to break backwards compatibility. I think if we want to be relevant years from now, there are going to be moments where we have to shed and say, “We need to break things”. Now, if WordPress said, “We’re going break, obviously, you auto-upgrade, it’s going to break your site”. That’s a big problem. If they said, “I think we’re going to break 10 different modules in the site. You’re going to have to refactor those all at once”, we might have a large problem to talk about. But we’ve either got to accept slow breaking of backward compatibility on basis, slowly peeling back with enough warning and enough caution and things that we think are technical that are holding us back. Well, frankly, we might have to go the extreme opposite direction at some point, which I think is unlikely, given our philosophy of WordPress 2 or maybe WordPress X or WordPress 10 is the joke of the day or something.
But there’s a new generation of WordPress that is almost completely not backwards compatibility that just breaks with a lot of the old. You can keep using the old one, but at some point, you probably want to move on which is what Drupal did at a certain point, interestingly probably around the same point in the life cycle that WordPress is right now. So, again, rambling way of saying I’m not afraid of breaking some backwards compatibility and shedding some technical debt. And I think it’s being down, at least what I can see so far. Again, ask me again when 5.0s around the corner. So far, it’s being done in a way I think is responsible, considered and measured.
Jonathan: Yeah. I totally agree with you actually. Actually, it depends on how it’s handled, isn’t it? But this kind of howling and howling about backward compatibility, I actually think it’s taking it a little bit too far really. There’s a balance point, isn’t there?
Jake: Yeah. I think that’s the key. If we want to be backwards compatible forever, great. Hard to see us being around in or two.
Jonathan: No. Because that’s all linked to the previous things we’ve discussed in this discussion, isn’t it? It’s all linked in a way, isn’t it? Like I say, I think there’s a down to earth point where it becomes actually damaging. It’s actually better, it holds the whole platform back, doesn’t it? But there’s been on occasions, you still want to honor backward compatibility and to a certain degree because it can be very damaging if it’s not, isn’t it? So I think we’ve covered that. Let’s go on to something non-political. Let’s go on to Sacremento WordCamp. That’s this weekend. You’re going to be there. I’m going to be there. And almost all, a fair crew of the WP-Tonic roundtable posse are going to be there either presenting or there like myself. Obviously, you’re not involved in the running. But you’ve been involved very strongly with the of the WordCamp and Meetups in Sacremento. So are you looking forward to it? And how do you think it’s going to go in a new venue?
Jake: I’m pumped for it, maybe a little bit selfishly because I’m not on any kind of organizing or volunteering duty. I’m.
Jonathan: Thank God. Thank God.
Jake: this year. Immense credit to Jennifer Bourn in particular and the whole organizing crew over there. They’re doing a fantastic job. I know this is going to be probably one of the best organized and best run Camp’s that I’ll go to in the next year. So I’m excited about it. I’m excited for my talk. I’m excited for the roster which I think is incredibly impressive out of Sacremento. I’m excited to see you and Tonic crew and everybody else. I haven’t gotten to go to the Meetup as often as I would like to since I’ve had my kid and I’m kind of on parent duty a lot of nights a business. So I’m also just looking forward to catching up with a lot of the community down there.
Jonathan: I think what we’ll do, if you’re okay with it, I think we’ll go for our formal end to the Podcast. And are you okay to spend another 10 minutes on the YouTube channel? People would be able to see you on the YouTube channel and on the website. Is that okay?
Jonathan: So Jake, how can people get to know more about 10up and about yourself and what you’re up to?
Jake: Best way to learn about 10 up is to either follow us on Twitter which is shockingly @10up, 1 – 0 – u – p, not spelled out or go to the website of the similar domain and stay tuned to our blog. For me, personally, it’s jakemgold, j – a – k – e – m – g – o – l – d on Twitter is sort of the public persona. You can also go to facebook.com/10up.agency on Facebook to get some updates about the company. I think those are your best bets.
Jonathan: Oh, that’s great. To get hold of me folks, it’s quite easy. Get me on Twitter @jonathandenwood. You can email me personally at email@example.com and I do answer my email, not straight away, but if it’s urgent, I will get back to you as soon as possible. And basically, if you want the show, we love people commenting, giving us feedback, people you want us to interview, topics that you want us to cover. And if you’ve got a spare moment, if you can give us a review on iTunes. I say it every week, but it does really help the show. I just want to say to Jake, you’ve been a great member of the WordPress community. You’ve helped me personally on a couple of issues. Really appreciate it, great guy and I’ve really enjoyed the interview. And you can hear more. We’re going to continue the discussion on YouTube which you’ll be able to see on the YouTube channel that’s getting more and more subscribers. Go to the website and there’ll be a full transcript of the interview on the website there as well. We’ll see you next week where we will be interviewing a member of the WordPress community, a business owner that uses WordPress or just a WordPress junkie in general. We’ll see you next week folks. Bye.