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#96 – Jake Goldman on Agency Mergers and AI in WordPress

[00:00:00] Nathan Wrigley: Welcome to the Jukebox podcast from WP Tavern. My name is Nathan Wrigley.

Jukebox is a podcast which is dedicated to all things WordPress. The people, the events, the plugins, the blocks, the themes, and in this case, the recent merger of 10up and Fueled, as well as some thoughts on how WordPress will adapt with AI.

If you’d like to subscribe to the podcast you can do that by searching for WP Tavern in your podcast player of choice. Or by going to forward slash feed forward slash podcast. And you can copy that URL into most podcasts players.

If you have a topic that you’d like us to feature on the podcast, I’m keen to hear from you and hopefully get you, or your idea, featured on the show. Head to forward slash contact forward slash jukebox, and use the form there.

So on the podcast today we have Jake Goldman. Jake is the president and founder of 10up, a digital agency that builds websites and tools for content creators, leveraging open platforms like WordPress.

We start the conversation with an exploration of the recent merger with 10up, Fueled and Insignia. For many years 10up has been one of the leading enterprise WordPress agencies. With a roster of well-known clients, Jake has grown the company from himself to hundreds of employees.

Whilst the journey has been exciting and challenging, Jake talks about some of the areas in which 10up has not been able to compete, and how the merger with Fueled will enable them to position themselves for projects which used to be out of reach. Fueled brings their experience of crafting mobile experiences, and Insignia brings their financial expertise, as well as the industry connections they have built up.

Jake shares how this new venture will continue to leverage WordPress as their CMS of choice. These new partners understand and support 10up’s commitments to contributing to WordPress. There are no plans to immediately alter the structure of either 10up or Fueled. It’s more about building an understanding of the capabilities of each partner, working towards a future in which the company grows into one entity over time.

We talk about the intentional pursuit of potential partners, and Jake reflects on the importance of cultural alignment and connections. He shares how his prior experience has shaped both his personal journey as a leader, and the success of 10up. And we explore the milestones, challenges, and key moments that have brought them to where they are today.

Towards the end of the podcast, we pivot to talk about the role of AI in the future of WordPress. It’s clear that AI is coming, and it’s coming rapidly. Any agency working with WordPress would find this topic hard to ignore. But what impact will it really have? Are we expecting entire websites to be built in seconds by just clicking a button?

Jake expresses his view that these tools are to be seen as accelerants, complementing human website development, rather than replacing it, particularly at the enterprise level. We delve into 10up’s ongoing exploration and experimentation with AI, discussing some of the tools they have freely released.

If you’re interested in how enterprise agencies grow or the future of AI with WordPress, this episode is for you.

If you’re interested in finding out more, you can find all of the links in the show notes by heading to forward slash podcast, where you’ll find all the other episodes as well.

And so, without further delay, I bring you Jake Goldman.

I am joined on the podcast today by Jake Goldman. Hello Jake.

[00:04:31] Jake Goldman: Hey!

[00:04:32] Nathan Wrigley: Very nice to have you on the podcast today. Really appreciate you joining us. Jake is joining us from 10up.

10up very recently had some really quite seismic news. In the WordPress community 10up is one of those companies that you have probably heard of. They’re an enterprise level agency, they deal with some of the largest projects in the WordPress space, and they had some news around a merger. So we’ll get into that in a little bit and we’ll also get into some AI topics probably towards the end.

Prior to that though Jake, I’ve just given a little bit of an introduction about where you work, but I’m curious about your backstory, particularly as regards WordPress, this is after all a WordPress podcast. So would you mind just giving us a little bit of your backstory. Where you fit into the WordPress ecosystem? What is the company that you work for and how did you set that up?

[00:05:22] Jake Goldman: Sure. I’ll see if I can do this concisely. I feel like there’s so much to the backstory. 10up today is a shop that I have run for twelve and a half years now, as we’ll talk about. Part of a larger organisation. We are a web agency and we have been very proudly advocates of open source, open technologies, WordPress is our tool of choice. We also very much believe apropos of open source and giving back to the web, and helping continue to make the web an open platform where people, you know don’t have to pay huge licensing fees to be involved, be able to make websites, be able to learn new technologies and new skills.

And we very much believe that as we have climbed up that ladder of an open web that we need to keep that ladder extended to the next generation. So we are also very large contributors to the project, we donate thousands of hours every year to open source. A large part of that goes to WordPress Core. Goes to a rich ecosystem of extensions that we contribute, that we think solve some hard problems, particularly in the enterprise, the kind of customers that we serve.

Before this new event, just as 10up we’ve been about 300 people. That is a company that has grown organically from 2011 when we were founded, with just me writing code and doing a little bit of UX, and doing all the business side of things and built it sort of brick by brick.

I got into WordPress circa 2007, 2008. I was working at a shop as many were at the time focused on commercial CMSs and closed platforms. We kind of wanted to diversify, saw the writing on the wall. Started exploring with different popular open platforms at the time that was WordPress. One of the partners in that company was focused on Drupal.

I saw a lot of potential in that platform that came, I thought, to pass over the next few years, and when it was time for me to go out on my own and start my own business, I was pretty determined that if I believed in an open web and wanted to see open technology thrive, that WordPress was a good horse to bet on. And so started 10up. Determined to become one of those agencies of record in the space. I guess the rest is history.

[00:07:02] Nathan Wrigley: Did you have any intuition back then that WordPress was, you spoke about it in terms of it being you know a good horse to back. Did you have any intuition that it was the horse to back? Or would you have been prepared at any moment to swap horses mid race you know had Drupal pushed ahead? Because I had all sorts of intuitions, many of them which turned out to be completely wrong in terms of Drupal and other open source platforms.

And eventually after WordPress became successful, I joined that ecosystem. But it sounds like you made a bit of a serendipitous choice. It was a bit of good luck possibly. And I wonder what your thoughts are around that.

[00:07:38] Jake Goldman: Yeah I mean there’s always an element of luck. I could have chosen never to look at WordPress, right? Or taken it seriously as a platform. I certainly thought I saw potential. I mean, you work in web from 1996 to 2007, you’ve tried and dabbled in lots of different technologies. I think it was, maybe this is the older man in me speaking now, but I think it was easier at the time to move between different technologies. There wasn’t so much friction trying new things, trying new platforms.

As somebody that’s very, that likes engineering, and likes tech, and likes the geeky side but also has a strong appreciation for user interface and making things easy and putting myself in the shoes of people that are actually just trying to publish something on a website. Actually trying to manage content, always wanting throughout my entire time in web to be able to like hand off a website, maintain it, but be able to hand off and have a delightful experience for those website owners to keep updating their website and managing the content on their website.

It was very clear to me even 2008, 2009, I think it was around the time of the first big UI change in WordPress, you know the menu on the left and still elements of that echos of that design today in WordPress. It was very clear to me that in terms of platforms that we’re creating really focused on, what is that website owner, what is that content publisher experience that WordPress was, I thought, just running circles around the other platforms?

So I saw a lot of potential. I was experimenting with even doing things that were custom post type like before there was really custom post types in core, and saw where the core project was heading in terms of adding more taxonomy support, adding more different content types and some of those fundamentals of a bigger CMS.

So I guess a bit lucky that I happened to be stumbling and playing and looking closer at the platform at the time, but I guess the short answer is yeah, I mean it was very palpable to my instincts that this thing was going to go places.

[00:09:11] Nathan Wrigley: If you were to look back over the time since 2011, that number of years, the ground will be littered with people who tried to do what you did, but didn’t quite make it. You know they endeavored to have an enterprise level agency, they wished to grow their agency. But for some people clearly that worked, you being one of them. For other people, perhaps it didn’t work out.

And I’m just wondering if you’ve got any intuitions as to what the key moments were in those years. If you look back and think, okay that was the moment, that was another moment, that was a third moment. What were the pivotal bits, the decisions that you made, the projects that you took up, which allowed you to become the sort of force that you are now?

[00:09:48] Jake Goldman: It’s a great question and, you know, I’ll be earnest, I never really look at the sort of long journey and arc as, it’s nice to think of it as like there was this moment and everything changed. But it wasn’t really like that. It was a brick by brick, year over year kind of effort. I mean when I look back at moments that I could call out, you know certainly when starting the company, I’m not sure if this is a moment so much as a story you know sort of a narrative about, I think why we were able to be successful.

But I’ve always emphasised that the trick to, I think, 10up’s success is that I did not descend out of the sky one day out of college and say I’m a business owner. Before I started 10up I spent over a decade working for other people, doing side consulting. There was a whole story before 10up started which was time in the industry, building connections, building a network, investing in relationships, learning from mentors about how to think about a budget, and a P and L, and what’s really involved in hiring people. Having the joy of hiring someone great and the torture of having to let people go before I ever started the company. Knowing how to put numbers together, had fantastic mentors.

If you want the honest answer, the real story of our success is, it was everything that happened before starting 10up. It was the relationships I was able to bring into that company, clients like side consulting projects I had been doing on the side for over a decade that I was able to bring in to the company.

I think there’s a lot of people today that sort of drop out of the sky and say you know my role in life is to be an entrepreneur and day one I’m starting a company and I just, I can’t imagine I would have been nearly as successful, 10up would have been nearly as successful as it was if I didn’t have that whole backstory.

I can point to some other moments, you know winning in the first year. Getting introductions vis-à-vis those connections to customers like TechCrunch that we still work with to this day, on their site that have obviously become very powerful items in your portfolio. I can point to bringing on strong leaders including our CEO who joined us in 2014, still with us today, John Eckman.

I think one other thing that has made 10up different than some companies in the space is I like to believe it is not a company that revolves around its founder’s ego. That I’ve always tried to build it with a mindset of, I want this thing to be much more than Jake Goldman. I want the brand to be 10up not Jake’s company. I could ramble on but I think, that’s probably what I would leave you with.

[00:11:51] Nathan Wrigley: Well thank you. The thing that we’re going to talk about from now is the joining of forces between 10up and a company which in the WordPress space maybe people haven’t heard about, and that is Fueled. We’ll talk about a piece which went on the 10up blog, I will link to it in the show notes. It’s called Fueled Up, 10up joins forces with Fueled Digital Media. And so that’s the direction of travel for the majority of the rest of the podcast.

But I’m just wondering, in that journey, was the endeavor always growth? Grow, grow, grow, make the agency bigger. And if that was the case, what kind of changed your, direction? Because it seems like you had a bit of an epiphany earlier in the year of 2023. The article paints a picture that you were working with Fueled and then just have this sudden realisation, actually do you know what they are like us. They do something different but their alignment, the sort of direction of travel, their ethics, and all of that seems to match very well.

And then all of a sudden, well I say sudden, probably months and months in the making, you announced that you’ve joined forces. So I just wonder, what changed about the company that suddenly made you think let’s do something different, let’s join with some other company?

[00:12:55] Jake Goldman: It’s a fantastic question and the reality is, I’ve written about this a little bit online, like my prior story. It was not a wake up one morning, my you know light bulb went off and the next day we closed the transaction kind of a thing. The reality is, I think we have to go all the way back to saying like, per my last remarks, I have always seen 10up as something that is, I want it to be much more than Jake Goldman Inc. That was always my vision.

If you think of me as an engineer at heart, I always sort of believe like the best thing you engineer is a thing that continues to live on and be used well beyond the time you spend on it, well beyond your focus on that project. And I’ve always felt the same way about a company, like the perfect business, the ideal company, the ideal team that you build.

There’s a world where you can someday step back and not be worried if I’m not in the room that this thing doesn’t keep succeeding, this team doesn’t keep thriving. That’s always been on my mind. It was on my mind when I think I surprised a lot of people, again, going all the way back to 2014, and hired a CEO that was not me into the company to help us build it. It’s always been on my mind as I built out different divisions and empowered strong leaders within the business.

I think there was a moment for me in the, you know the first few years of the 2020s, to me sort of peaking in 2022. Not sure intentionally but probably not accidentally after probably two or three of the most difficult and challenging years to be a business leader probably weighing on my mind as well. Any business leader who does not tell you there was a certain fatigue in 2020, 2021, 2022 is probably not being honest with you.

At the same time, more consciously I just felt like look, we’re about to break through $40 million in revenue, we think by the end of this year. We think we’re on a trajectory for 300 people at this company. I have been the overwhelming owner of the business, decision maker for you know, at that point for I guess 11 and a half years. And really felt like as we move forward this company needs to have more governance, a different kind of structure, a different kind of ownership that can A, help keep propelling it forward.

I’ve never run a company of that scale in size before. I think some of what you have to do to manage and invest in a company of that scale is a little bit different when you start to reach that kind of size. And I frankly want to make sure this company is taken care of in the event that I ever, you know I could get sick, I could get hit by a bus.

I don’t think the company even as it existed previously, would suddenly just disappear overnight by any means. But there was a certain amount of like legal structure, a certain amount of like ownership management, and share structure. A certain amount of where are the other highly experienced, growing companies of this size kind of leaders and investors that were missing.

And when I thought about I can go through the effort to do that on my own, think about like employee owned companies or think about how to completely restructure stock and legal formations. To be honest with you, when I started thinking about that, I was struggling to imagine being excited to get out of bed for the next two years focused on like legal apparatus, and being that different kind of owner of that larger company which just. You know so I guess I’m rambling a little bit to say like that mindset that I was in of I think we need something more in terms of governance, ownership, to a degree, diluting the degree to which it sort of sits on my lap as an owner.

Combine that with my sense that the next phase of growth is, I think, going to come from moving even further up market to being even more of a serious competitor to like the Deloitte Digitals and the Code and Theory’s of the world, the people that are not coming in saying you know we’re great WordPress integrators, or just great website makers but were true full digital experience shops.

I think those things kind of collided for me in a way that said maybe it’s time to look at M&A. Maybe it’s time to look at who we can join forces with. And I’ll be transparent, we went on a very intentional journey, we had advisors in that process. It was you know help guide me through an exploration of you know who might be the kind of company that you can join forces with. And let’s not just wait for it to fall in my lap, or just go on this blind exercise and all the you know, all my copious spare time of hunting.

But be intentional about seeking who those partners would be. Spoke to a lot of different companies, had different sort of, I would say suitors, or even offers of which we walked away from. But as we got to know Fueled in particular and then started to do some projects together, and started to understand each other, it felt very clear to me that this was a unique and special fit.

[00:16:45] Nathan Wrigley: Okay so let’s talk a little bit about Fueled. So I’m curious to know, what is it about them that make that fit special? So presumably you went out and I’m obviously going to paraphrase the whole process, but there must’ve been a series of check boxes that needed to be checked. The company needs to behave in this way, it needs to have this, it needs to have this, we need to be going in this direction, whatever it may be.

I’m just wondering, why was it Fueled as opposed to all the other companies? And you can take that in whichever direction you like. It may have just been personnel, it may have been turnover, it may have been, I don’t know attitude, roster, anything you like.

[00:17:16] Jake Goldman: Yeah it’s definitely not just a one thing, but I have to say a lot of it sounds very non business like in a sense. But a lot of it was ineffable. A lot of it was just when you go and you meet with these different suitors, or these different potential partners, or companies that you could merge with. And you sit down in the room with them or you have, you know you start with the Zoom chat. I find myself sort of imagining okay, I’m in a boardroom in a hard time or a good time with them, a year from now, two years from now, how does that feel to me?

It’s a sort of cultural, does this feel natural? Does this feel like somebody that if I had to have hard conversations it wouldn’t be stilted, and more painful than it needs to be? Do I feel like I would be energised and sort of like an extroverted kind of way, like walk out of meetings and planning sessions more excited about what we’re doing, or would I feel a bit tired from that exercise?

And I’m trying to think how else to express it. It was just like when I sat down with them, when I met with them, when we actually worked on projects together and collaborated. It felt like if I had brought these people to, you know, if I just brought them to my team and said I just hired this person as a new key executive, or a new key director, or leader, everybody would have just said like you know great hire Jake, what an amazing fit for our culture.

And I think that was extraordinarily important to me. Yes, there were other boxes to check. The financial side of everything had to make sense. The legal apparatus had to make sense. They had to be in a, obviously, you know reasonably healthy condition as a business. There were things I did not want in terms of like kind of companies that I thought could like destroy what’s precious about 10up and its culture.

I could talk about all of those things, but at the end of the day when sort of settling down on that gut feeling of, is this a company that I want to be with, that I want to work with, that I want to join forces with? It was the checking of the boxes, different kind of skills, different kind of capabilities, all of those things.

But at the end of the day, a lot of it came down to these are good people that I would enjoy working with. I would look forward to going to a board meeting. I would look forward to going to an exec planning session. They will make me a better leader. They will make my team better. My team will enjoy collaborating with these people in ways that you know going through this journey and talking to so many companies, even before 2020 like we’ve been approached before, and we’ve had conversations with different companies.

You start to realise how precious that match is. We can all sort of like be in our bubbles. But really when you start to talk to a lot of these different companies and agencies, you really realise pretty quickly that there are a lot of companies, a lot of people who are doing fantastic work, impressive businesses, but just very different kind of mindsets, cultures, communication styles, ways of thinking about the world. So when you find someone that you actually go and sit down in the meeting and it’s like I could hire you, I wish we could do more projects together, that’s something you latch on to.

[00:19:39] Nathan Wrigley: Yeah what a great answer. I really enjoyed listening to that. The next thing I want to talk about is, how Fueled overlaps with you? So I’m imagining in my head a Venn diagram of two circles. And in the past, in the WordPress space, we’ve often seen one agency, for want of a better word, consume another agency. And it almost feels like the two circles are now completely overlapping. One is inside the other. So you can no longer see two circles. You just see one slightly bigger circle.

But it does seem as if with Fueled we’ve got a nicely fitting Venn diagram. There’s Fueled over here, there’s 10up over here, and there’s some elements of overlap but it’s not entire. The two circles are not colliding. And I’m just wondering, what it is that they do? What it is that you do? What’s the differentiators, and what is that lovely sweet spot in the middle where you both overlap?

[00:20:23] Jake Goldman: So I’ll start with the sweet spot in the middle. The sweet spot in the middle, to be a little highfalutin about it for a second, is like the desire to use technology, to use cutting edge innovative tech to create fantastic experiences for clients in an agency setting. It really is in some sense that crisp and that simple. We are a professional services business. We use online technologies to make great experiences for our customers.

Now to be a little less flippant and a little bit more specific about it, like where we have skill set overlap. Fundamentals of doing design systems, whether it’s on mobile for a product, whether it’s on a website. Those are not fundamentally different like technical skill sets that you use every single day. There is an overlap and some like you know Next.js, React kind of front end technologies. They do some web applications in addition to mobile. In fact probably a growing part of their business relatively speaking.

But when you get beyond the sort of like core common technologies and practices you use when you’re a creative agency, and expand out to okay, what do we actually work on day to day? There is a healthy, non overlapping parts of the circles, outside parts of the Venn circles. Which is to say like I would say that they are predominantly focused on what they are good at, what they are known for, what they have repute in, is doing product development in the sense of mobile applications. Some web applications, but not marketing websites and publishing websites. Not CMS driven experiences really. Like applications, you know e commerce kind of functionality. Think of some of the projects they work on where it’s really you know shopping and user intention driven.

10up is more on the website marketing, web publishing, web content creation. Again, we overlap a little bit, we’ve even done mobile apps in the past, but we are really strong in how to make a great website that can be put in the hands of those site owners, those site publishers with a strong content management system implementation behind it. And a major focus on content together. That’s media and publishing, or corporate newsrooms, or you know content marketing, or just flat out marketing websites and informational websites. When that was not something conversely that Fueled had really focused on or was good at.

And we both sort of you know looked at those two sides of the Venn diagram and sort of said, I bet we have a bunch of customers who could use the others services. And there’s a bunch of customers out there who don’t want a shop that sort of neatly fits in one bucket and is kind of stretching and reaching to have a compelling story about the other side.

[00:22:35] Nathan Wrigley: I don’t know exactly what the audience demographic is, but I’m sure there’ll be a lot of people who don’t work in enterprise agency land. And so this conversation is really interesting, and I am wondering if you’ve had to, probably this is the wrong word, but turn down work, or move away from work, or pivot away from work that, you simply as 10up, didn’t feel you would be doing the best job with. But now you feel, okay we can push forward with projects such as this in the future, because now it’s this bigger enterprise, it’s Fueled, it’s 10up, it’s whatever that’s going to be called in the future.

[00:23:06] Jake Goldman: Oh yeah for certain. I mean literally can think of projects over the last few years where we had great enterprise, large scale, huge spending customers who needed, just to say it plainly, in some cases needed a mobile application built, put out RFPs for that and probably would have, hoping I’m not being hubristic here, probably would have loved to work with us, at least would have taken very seriously a submission from 10up. Where we just felt like we would not meet qualifications, we’re not confident that we could do a good job, in a way that would not diminish our entire relationship with them.

It’s the more common scenario that I think about is where we are given opportunities to pitch business, we’re given opportunity, we have an introduction, we have a connection, and we just don’t quite compete in the right way in terms of coming across as having a real platform that you would describe as a full digital experience solution.

While it’s true that we have customers, we have business that I would say has been left on the table because we didn’t have these capabilities. What I’m more focused on is where do we not compete well for opportunities? Where do we not get invited into the room or just not last long in the conversation? Because to overstate melodramatically for a fact, we come across as a WordPress integrator implementation shop, not a full digital experience business.

[00:24:12] Nathan Wrigley: There’s a third circle in this Venn diagram which we haven’t mentioned so far and it’s a venture capital company called Insignia Capital. I confess I don’t know anything about Insignia Capital. So I’m just wondering, probably fairly quickly, I don’t know if you want to dwell on this, but I’m just wondering if you could explain how that fits in.

[00:24:29] Jake Goldman: Sure. So at the risk of splitting hairs for your audience they’re a private equity company which is a little bit different from venture capital. Probably not a very material difference for most of the people listening to this but it’s a little bit different. Sort of like, what are the returns they expect? How do they operate? Where do they get their funding? And so forth.

Still the same principle in terms of, I guess the short version would be that they are the money people. So the way that they fit, to try to make it concise, they joined forces with, made a massive investment in Fueled about one year ago. Which is to say they’re not the full ownership of Fueled. Fueled’s owners still hold a large share of that company, but they have controlling ownership, vis a vis putting a huge investment into Fueled.

And what Fueled, other than of course some opportunities for some liquidity for their owners wanted out of that, is a real partner who knows how to, from the investor side, has both connections, has both capital, has sort of financial and industry sophistication to help them build a bigger business together.

So to put it in plain terms, what Insignia wants to do is work with a platform, which for them that was Fueled as the initial partnership, the initial investment. To build a bigger, more valuable company that increases the value of the equity that they have in that business. The way that they do that oftentimes, like the strategy in professional and digital services is you do what’s called add ons.

So you bring in other companies into the fold, you attach them to that company and you end up with something that is much more valuable for a number of reasons. It’s higher revenue, but it’s also everything I just described about you have a you know, a shop that looks like a full digital services provider with CRM capability and sales force and CMS and mobile apps, is just a more valuable business than one that’s kind of pigeonholed in one of those spots.

So you can kind of make smart investments with investors that really raise the overall value of the business. Like 10up, I would say Fueled’s ownership really did not have the sort of the sophistication, appetite, capital to do that on their own. Which is why they partnered up with Insignia. Insignia has sort of the financial vehicle, all those things I described earlier in the conversation, where it’s what does it mean to restructure legally 10up to have multiple ownership, and to have shares and to have stock and to have investors with a lot of influence and connections in the space.

So long story short, they help us restructure to be able to join with Fueled, to be able to make one business out of these two companies. And that happens, in large part, by helping purchase a significant amount of 10up equity, so I am no longer the dominant controlling owner of 10up.

It’s a little muddy, and I guess like the short version of it is like they are the financial backers for this combined entity. They make it possible to restructure the business and combine into one through capital, and they also bring quite a bit of sophistication around how to build these platforms. They have connections with other companies that can be acquired, they have a lot of connections with very senior, influential people in the decision making space, in the agency space and in the B2B space. So it’s not that they just bring money, they also bring a lot of wisdom about how to build these larger companies as investors, advisors, board members with strong connections.

[00:27:12] Nathan Wrigley: Now that the ink is dry on the contracts and you’ve had a little bit of water flowing under the bridge, I’m just wondering if you can tell us how 10up particularly has changed? I know that your company is broadly distributed, and I just wondered, what is it that it’s going to look like if we can cast our eyes forward a year into the future? What are you endeavoring to create there? Is the idea that this one entity, everybody will be mixed? It will be a homogenous entity or will we have, broadly speaking, will we still have the WordPress side? What are you planning?

[00:27:42] Jake Goldman: So the first thing to say is when we get like sort of in the weeds of how it’s going to operate, and a question of like what has changed today. So far that is still a journey of discovery that we are on. That’s not BS, that is authentic. I can speak to what we all sort of I think share as like a heading and vision and ultimate destination, when you talk about the one, two, three years out.

But we don’t think that means like jumping in and month one, this is not like shifting around 17 different divisions and immediately restructuring in three months. No, we are learning from each other, we are still deep in the process of teams and project management, and design, and growth, and sales, and engineering. Sort of comparing notes, getting to understand each other better, getting more insight into each other’s businesses. Sharing leads, sharing opportunities that we think might be better fit to one team or the other. Sometimes sharing personnel where they’re skillsets overlap and one team or the other could use help.

But really operating essentially as two, continuing to operate as we did before the merger, as two strong partners with a bunch of research, discovery, integration, exploration going on in the background of the company.

In terms of where we are headed. Yes, our goal is ultimately not to be like there’s a 10up and there’s a Fueled out there competing in the agency space, and sometimes sharing opportunities. Our ultimate goal is to be a unified business, to have a clear, centralised governance. To be able to go to market as one entity, one brand and sell a story of not two different partners working together, but one fully integrated set of capabilities.

Now what that looks like again, there’s a lot to color in there that I just don’t have the answer for. I don’t even know that I have an answer, a definitive answer today for where like the brand question would even land. We might find ourselves in 12 months in a model that is still fairly divisional. Which is to say maybe more centralised leadership, centralised operations, more marketing and business development consolidation, but could still sort of like operate with divisions within the business.

One more focused on applications. One more focused on web and CMS. Could end up with some teams that are totally cross functional. The honest to god answer is that is what we are exploring and trying to work on with our teams and find the best path today. Better right than quickly is our point of view.

[00:29:35] Nathan Wrigley: In terms of the roster that you’ve currently got. Now you mentioned TechCrunch, and we know that there’s a whole bunch of other enormous companies that you’ve worked with. Did you feel compelled to go out and communicate with them prior to heading down the direction of merging with Fueled? Was there any intuition that maybe your clients would be interested to know that information or potentially you know, nervous to hear that you were doing this, and how would it affect their incredibly important property?

[00:30:00] Jake Goldman: In a spiritual sense we did not have a lot of concern about it. We thought it would make sense. This is not a case of say it rather crassly like being gobbled up by some international conglomerate that might be controversial to some customers. This was not a case of like changing to foreign ownership of a business.

It was hard to see how any customers would be anything but sort of happy to hear that we have maybe more sophistication as an entity and a governance and ownership model than, one guy in California owning the business. And pleased to hear that we were expanding our capabilities and could offer more solution and more services to them in the future. So we didn’t really have any sense that like somebody was going to be very upset to hear about this.

There is a process, there is a certain amount of like notifying, interviewing a small number of customers beforehand that are seen as, maybe riskier because they have strong terms in their contracts around change of ownership. Or just large clients where you know nobody’s going to be happy if for some shocking reason it changed the game afterwards.

So were some that were informed and brought into the loop, not because we had deep existential concern about it, but because it was a part of a due diligence process. We did speak to a few customers but otherwise the process was largely once we knew this was closing, once we knew this deal was going to get done, it was a rapid notification process. A harried two or three weeks right after the deal closed to make sure that we had a very orderly structure. But a quick way, inform those clients, let them know what that meant for them, deal with any contract language implications or updates. And I have to say I think that went exceptionally smoothly.

[00:31:24] Nathan Wrigley: Just touching on WordPress, this is after all a WordPress podcast. You have mentioned that your team over the years has contributed really quite large amounts of time and effort and resources to the WordPress project itself. And so I’m just curious as to whether this has changed anything. Or whether you are still everything pointing towards WordPress going to be contributing in the same way. Still using that as the platform of choice for the web side of things, if nothing else.

[00:31:50] Jake Goldman: So in terms of contribution nothing has changed. My hope is that this will open up added opportunities to contribute, make impact in the space. I think all of our new partners, Fueled, Insignia, understand that you know endemic to our strategy, our culture, our core values is that level of contribution that we make to the space.

It is, you know even if you don’t believe in it from an ethical sense, from a business sense it has made sense for us and it has helped us grow and it’s helped us acquire business, and helped us have impact, and build culture. So you know there are no plans to change that level of investment that we make.

In terms of WordPress as a CMS platform, yeah, I mean at the end of the day Fueled and Insignia fully understood that that is our preferred CMS platform, that is the dominant platform that we use. Fully understood that, you know making a bet on 10up was also making a bet on WordPress continuing to be healthy and grow as a platform. The CEO, a lovely fellow named Rameet literally spoke to Matt Mullenweg, as I understand, before I even knew he did about WordPress and about 10up.

At the end of the day they are looking, you know they chose to merge with us and are looking for us to be the experts in CMS implementation and looking for us to be the experts in how to make these websites and experiences. They don’t have a hubris to think they’re going to come in and tell us, we wanted to merge with you but we think you’ve been doing it wrong the whole time, and you need to change platforms, right? That’s almost silly as a way of thinking about it.

The short answer is I mean yes, they very much understand what they were buying. They see us as the experts. They look up for us to continue guiding and we continue to see WordPress as our dominant platform that we work with.

[00:33:14] Nathan Wrigley: I hope you don’t mind me asking you some personal question. I’m just wondering how this is going to affect you? You may decline to answer this question if you wish, and we can just cut it out entirely. But I’m just curious. From a lot of what you said there did seem to be some little bits of, you were intimating that some of these things were going to be wonderful for you as well as the company.

And I’m just wondering if you’ve had any of those experiences? Has work become more pleasurable? Have you managed to get out of this what you want? Have you managed to make new friendships and new alliances? Is it everything you hoped it would be?

[00:33:46] Jake Goldman: That’s a big question. I mean there’s two ways to answer that. I think there’s, I’m not trying to dodge, I think there’s a couple of different, two different ways of looking at that question. So the biggest sort of like aspiration that I wanted out of this, which is new partners, having people that are more my equals or even my seniors in this combined business. New advisors, new people that take true, you know in addition to some people on our team, new people, new additions to the team that take real, literal ownership of the business.

Yes, that is the case and it is welcome for me to have that, those kind of additions. I adore many of my new peers, feel energised when I work with them, when we sit down and plot out the future and work together. All of that is true. Now I think in the moment, four weeks in would I say that my life is now flowers and roses and better and easier? Let’s be earnest here. There’s two things going on at the moment. One is I had the same full time job that I had the week before, with a little less heavy as the head that wears the crown going on. But the same job that I had the month before in terms of like, again, we didn’t snap our fingers and transform the business operations overnight.

And now I also have this additional responsibility, which I take very seriously of that, playing a key role in facilitating change management and a longer term integration strategy. So if I was being very honest at the moment, my feeling is delight with the partners that we’ve chosen. A little bit of overwhelm and fatigue on like how much more there is to do at the moment. The seriousness with which I take this whole process is not a light burden. Doing big change management across a team of our scale is not a light duty for lack of a better word.

[00:35:13] Nathan Wrigley: This question would be best answered in a year’s time.

[00:35:15] Jake Goldman: A hundred percent it would.

[00:35:17] Nathan Wrigley: Let’s put that topic behind us and just get onto a subject which is completely nothing to do with what we’ve been talking about. Just for a few moments. I’m interested because AI is all the rage, if we were to rewind the clock two years, just two years, I don’t think anybody really in the WordPress space was really talking about AI. Maybe tangentially or some aspirational talk about what it could do.

And now fast forward to today. We’ve just had a year of utterly seismic change in the capabilities of what AI can do. Most of it disconnected completely with website building. So we’ve got OpenAI and Anthropic and a bunch of other companies launching really seismically amazing products. And I’m just wondering what your thoughts are? What your intuitions are about where this is going to land with website building, with WordPress?

Now I know that’s an incredibly broad question but I feel that’s all we’ve got at the moment because we don’t have concrete things to pin our discussion to. So I’m just wondering what your general thoughts are.

[00:36:16] Jake Goldman: Great question. Hang on one second while I type that question into ChatGPT. So we have lots of thoughts and lots of initiatives going on there. I think the first one to call out, and this is a bit of a plug, we have an extension we’ve been working on since before this was cool, since 2018. Back when we called this machine learning more often than artificial intelligence, called Classifai, that’s C L A S S I F A I, because we’re too clever with our puns. So, or just look up Classifai or 10up and AI, it’ll probably come up. I’m sure I’ll put it in show notes or something.

That plugin has been an experiment staging ground with us for, again, going back to 2018. It is not focused on like how to, I’m not sure I buy that this is the right use case for our kind of customers or you know the dominant part of the market. It does not try to be one of these like, we’re going to build your whole website for you. We’re going to write your story for you and your content. And those are cool demos, there are probably some very small business kind of use cases where you just need kind of like a boilerplate, you know you need to have the brochure. That just has to be a checkbox put next to we have a website.

But for the kind of market we work with I don’t think those are more than frankly sort of novelty demos at this point in time. That might change as the technology gets better in a year or two, but I don’t think a serious marketer is saying I’m going to write my pages and do my layouts just using AI on its own.

What we do think is that AI integrated with WordPress, which is what Classifai aims to do, can be extraordinarily powerful in simplifying repetitive tasks, and being an assistant and support to people that are creating and publishing content. So it does things like integrate natively with image generation services. If you want to generate a photo for your site, it will do things like create alt tags, and text descriptions for images, smart crop. It’ll take a pass at making paragraphs shorter or longer, individually in form on your site. It’ll tag images so you can navigate your media library better. It’ll suggest alternative titles you might want to consider.

So we are very focused in Classifai on what we would describe as extremely pragmatic, realistic, not novelty demo, kind of integration so that WordPress can compete. You know it’s completely open source, free plugin. You have to pay sometimes for the third party services, like the image generation services are mostly licensed. But we don’t make anything off of that, you just buy those services and plug your keys into Classifai settings.

So this very pragmatic setup where we think that customers, we hope other people using WordPress, can look to Classifai to be a very sort of modern, sort of high end, prosumer enterprise solution that gives an answer to, how do you use WordPress and AI?

On the technology, engineering side we have a working group. We have ongoing exploration of how do we in a safe way, in a private way, that respects our customers but in a way that keeps us competitive, continues to make sure that we don’t fall behind or suddenly become just wildly out of league and what it costs us to make something. Is experimenting with things like GitHub Copilot and more structured ways we can use that across projects. Experimenting with things like code generation with chat GPT. I don’t think the kind of websites we make are going to be like, build a whole website or 80 percent of the code with those tools.

I see it as an accelerant, no different than like when we had IDEs or even when we shifted from writing machine code to more natural languages like C and C++ and Swift and all the rest. And I think it’s still early in that exploration. There are certainly signals that there are some kinds of tasks, certain migration tasks, certain repetitive scripting tasks in the shell that you can automate, that you can accelerate.

And our job right now, and that job’s not done, is to figure out when you have a scale of you know 300 people and 100 or 200 some engineers. How do you create a standard? How do you create a process? What does it mean to create an expectation? Not across one or two people who are smart, curious and hungry to use these, but across an entire team to stay competitive and stay ahead of the curve.

I wish I could bring you all the answers other than to say like I think that technology will keep getting better. I do think it will help. I am not in the camp of at least for the next you know sort of five years. I am not in the camp of, this is going to replace the need for engineers. You know there are certain leaders in the WordPress space who I think would say like they imagine a few years from now their engineering teams go down from like a hundred to like five.

Maybe I’ll eat these words. I think it’s a bit silly when we think about the next two, three, four, even five years. I think it’s more like an extreme version of the leap again to like things that would have seemed very foreign 40 years ago, 50 years ago when the industry was frankly smaller, not larger. Where we started to have tools you know template patterns like you know the internet and access to Stack Overflow and good code completion tools.

These accelerant tools did not obliterate the industry, right? The industry is larger than it’s ever been. Which is to say like a rapid, rapid, huge changes that make engineering and technical tasks easier has never in the history of tech and computing and the web made for a smaller industry. It has always made a larger industry. It just gives people more time to think, to be creative, to make things that are more advanced. It’s raised the bar higher on what people expect in terms of quality and completeness of the experiences they get. I think that is more the world that we live in for the next three, four, five years now.

[00:40:59] Nathan Wrigley: I’m just wondering if there is some little part of AI which you’ve looked at, and again you know if this encroaches on business processes and things like that, you need not divulge what it is. I just wondered if at the level that you’re working at, if there are certain aspects of AI which you’re thinking, boy that really would save us a lot of time. That really does look like something which we should invest. It sounded like everything that you were developing, the Classifai is for the end user broadly.

It enables people like me to do my work quicker. But I’m just wondering if there was something that you were curious about on the AI side which would make your business processes quicker. And again, feel free to not divulge if you don’t wish to.

[00:41:36] Jake Goldman: I mean the short answer is yes, I think there is. I’m not not divulging anything to say like I’m not sure in a sustainable way what those things are yet. I know what we’re experimenting with. I know what we see some promise in. I kind of take the longer view and feel like it’s not clear yet which of these are sort of novelties in their appeal. Which of these are have enduring power as change forces in our process. It still feels like we’re in a little bit of a, I think, still in the getting to know it phase. I do think there are some things around like more baseline tasks in an estimate, or when we’re building certain kind of projects or certain kind of sites.

My suspicion is some migration work, some sort of like more fundamental lower level like set up, the v1 of just setting up a basic added functionality. That will go faster, that will be accelerated. But I have to just be honest. I’m still not even confident enough that we’ve done that enough times, tried that enough times, to know whether this is more like when GitHub comes along, becomes popular whether it totally changes the way we work, or it’s just another tool that helps people be more efficient.

[00:42:39] Nathan Wrigley: My intuitions are that anybody that puts their flag in the sand and says AI will enable this is probably setting themselves up for having to admit that they were wrong. Almost everything that I’ve predicted has not come to pass. Yeah we just have to be, roll with the punches, be flexible I suppose.

Jake it’s been lovely chatting to you today about all of this. I wonder if you make yourself available elsewhere online. Whether or not you want to divulge a social handle that you use, or a good place where people can contact you. Having listened to this there may be people who wish to do that, and if you wish to spread the word about that please do.

[00:43:14] Jake Goldman: Here’s a phrase I never thought I would say five years ago. So the place to most get my insight and hear what I’m thinking about business and 10up is LinkedIn. So if you just search for Jake Goldman on LinkedIn I should pop right up, or Jake Goldman in WordPress. That’s probably the best place to go. I mean go to and follow our blog. I mean again all of our business activity as a company is there. In terms of like personal posting, not terribly active on any social media at this point.

[00:43:36] Nathan Wrigley: Well thank you Jake for chatting to me on the podcast today. I really appreciate it.

[00:43:40] Jake Goldman: Thank you for having me. It was a pleasure.

On the podcast today we have Jake Goldman.

Jake is the President & Founder of 10up, a digital agency that builds websites and tools for content creators, leveraging open platforms like WordPress.

We start the conversation with an exploration of the recent merger with 10up, Fueled and Insignia. For many years, 10up has been one of the leading Enterprise WordPress agencies. With a roster of well-known clients, Jake has grown the company from himself to hundreds of employees.

Whilst this journey has been exciting and challenging, Jake talks about some areas in which 10up has not been able to compete and how the merger with Fueled will enable them to position themselves for projects which used to be out of reach.

Fueled brings their experience of crafting mobile experiences, and Insignia brings their financial expertise, as well as the industry connections they have built up.

Jake shares how this new venture will continue to leverage WordPress as their CMS of choice; these new partners understand and support 10up’s commitment to contributing to WordPress. There are no plans to immediately alter the structures of either 10up or Fueled, It’s more about building an understanding of the capabilities of each partner, working towards a future in which the company grows into one entity over time.

We talk about the intentional pursuit of potential partners, and Jake reflects on the importance of cultural alignment and connections. He shares how his prior experience has shaped both his personal journey as a leader and the success of 10up, and we explore the milestones, challenges, and key moments that have brought them to where they are today.

Towards the end of the podcast, we pivot to talk about the role of AI in the future of WordPress. It’s clear that AI is coming, and it’s coming rapidly. Any agency working with WordPress would find this topic hard to ignore. But what impact will it really have? Are we expecting entire websites to be built in seconds by just clicking a button? Jake expresses his view that these tools are to be seen as accelerants, complementing human website development rather than replacing it, particularly at the Enterprise level. We delve into 10up’s ongoing exploration and experimentation with AI, discussing some of the tools they have freely released.

If you’re interested in how Enterprise agencies grow, or the future of AI with WordPress, this episode is for you.

Useful links

10up website

TechCrunch website


Fueling Up: 10up joins forces with Fueled Digital Media



ClassifAI plugin

Jake Goldman on LinkedIn