Not an Expert, Just Dangerous: 20 Years of James Ullman on the Struggle Bus

This content was created by Vinny O Brien. This content was uploaded by Vinny O Brien. This is a YouTube podcast episode titled "Not an Expert, Just Dangerous: 20 Years of James Ullman on the Struggle Bus" (Struggle Bus of VeeSpot Show), created on 2025-09-10. It is an English interview-style conversation hosted by Vinny O Brien with guest James Ullman. The discussion covers James’s ~20-year career in digital marketing and sales (Yahoo, Periscopics, NP Digital), agency vs. brand roles, imposter syndrome, team culture and remote work, e‑commerce trends, AI/LLMs and “search everywhere” optimization, the ongoing importance of human relationships in sales, plus personal anecdotes about music, tennis, and family.
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Welcome to the Struggle Bus of VeeSpot Show, the home of the e-commerce and early news. I'm your host, Vinny O Brien, or as my friends call me, hey you in the bushes. As an aged journeyman in e-commerce, I wanted to create the Struggle Bus to create a space for us long-suffering career veterans who've seen it all and quietly go back to the office to get our work done. With me today is longtime friend and the Benjamin Button of our industry, James Ullman. James has been working in digital marketing for the best part of two decades. I was going to say 20 years, but two decades sounds far longer. He's worked with Yahoo, Periscope, Omnicom, Smartly, and more recently he's joined NP Digital as the VP of Sales in the UK. Prior to this, he had an illustrious career in TV production for the BBC, ITV, not so much, and Sky on such shows as Eurovision Song Contest, maybe we get a song later with Jules, the BAFTAs, Outtake TV, etc. The main thread of all this though is James's career in sales and relationships, and by his own admission, he's not an expert in the chosen subject matter, but knows enough to be dangerous. I want to explore what that is. What he does love is interacting with people, understanding where products and services he's involved with can help with their own needs and challenges. Armed with a sports science degree, a love of music and performance, a singer with a checkered musical past, also runs a charity event, Media Rots, which we'll talk about. He has 3 kids and lives in the overly expensive Surrey. What he failed to mention in his own written intro to himself was that he is also a professional tennis coach. James, say hello. I've talked for too long already.
Thanks, Vinny. Thanks for the intro. I appreciate that. The tennis coach was a long time ago. So yeah, it was. I don't think recent performances would help me with that honor.
I'm going to take you backwards. Beyond your tennis career as well, because the first time we met as, as client and within the work environment was nice at Arnotts all those years ago. Would you believe that's nearly 13 years ago now? You were working with Periscopics at the time and you became our performance agency. Can you remember, and this is to all you people who are in modern agency world, can you remember how many keyword combinations your team came up with for duvets and pillows in our key sales category?
I can't remember the exact number, but I know it'll be in the thousands, I'm sure, because they had that sort of concatenator or that Excel machine that Vinny O Brien was using and the team were using at the time. It was absolutely phenomenal. They would— the agency at the time would recreate broad match inside an account. And, you know, in terms of the volume of keywords, it was something else. But whoever made that sort of rules-based machine in Excel was an absolute genius. And You know, I don't know where that's even gone now, but it's just pretty— everything's moved ahead. But it was a real thing at the time.
I think 22,000 combinations for duvets and pillows.
That's impressive. I suppose that would include all the colors, the brands, the types, the generic terms, all that kind of thing.
Luxury down pillows, luxury goose down pillows, luxury Hungarian goose down pillows. The list goes on and on and on. It's a really good indicator though, if you look backwards in the industry and where we are today. It's almost looking at like a Walkman versus Spotify where we find ourselves today. Can you throw yourself back and tell us what it was like to work on agency side at that point?
Do you know what, it was a lot of fun. So I'd come from a media owner in Yahoo, um, and I wasn't even sure I wanted to work in search anymore. And Periscopics was an agency that they had never been an agency before, and no one there had ever worked inside an agency, so it was really fresh for them. And they had a couple of great leaders, Mark and Simon, and then my boss Tom at the time running the sales function.
Great Tom Byrne.
Everybody, the great Tom Byrne. Everybody, everybody wore, you know, different hats. Everybody was pulling together. Now everyone always talks about things being a family and it, you know, you're supposed to say it's a sports team, not a family, but it just felt really contained and it felt like everybody was pulling in the same direction. We were pushing, we were pushing, we were pushing, and I felt part of that business, and I think that's why I enjoyed it so much. They created an environment that really helped people to sort of push on, and, you know, since that point, people have pushed on and become, you know, leaders in the industry, CEOs running their own agencies, different agency exits, creating and founding their own companies. Uh, it's been, it's been a phenomenal starting base, so I'll always really appreciate the time I had there with those guys.
And when I think about you in that role and the sort of values that you hold dear to you both personally and professionally, I always wonder why you never went brand side. Have you ever thought about that?
Yeah, I thought about going brand side a lot, actually. I suppose it's finding the right brand and something you'd be interested in. We touched on a couple of my interests at the start there in terms of music and sports. So there's probably lots that I could, I could, you know, move into in that sense, but would love to. I guess the imposter just the imposter syndrome that rages inside me thinks, oh, I wouldn't know enough to really help a brand about this whole subject matter because my main skill set, I suppose, is sales. Brands still need to sell, I suppose, but if I'm going into digital marketing a brand, I've always thought, would they want an expert more so, someone that knows the nuts and bolts of the workings of e-commerce or so on and so forth versus someone who can just go and sell stuff. But, you know, it remains to be seen, I suppose.
It must have been really frustrating then having an idiot like me as a client on the other side. The imposter syndrome comment, that was interesting because you are a musician as well and you love being on stage and it seems like it's a complete polar opposite mindset to be in. One, you're comfortable being up there, being the center of attention, and then you say you have imposter syndrome in that role. Why do you think that manifests?
It's a really, it's a really good point. And you're right, Vinny, and it's a good question. I do love being center of attention. I do love being on stage. I'm very strange like that. I don't know what it is about me. I love doing presentations at work. I love the element of performance. I love that. I think the imposter syndrome comes from knowing my subject matter. So I'm not an expert in digital marketing. You referenced earlier, I know enough to be dangerous. So I'm what they call a generalist, right? So I've got a little bit of, I've picked up little bits along the way. You know, with paid search, social media, programmatic, now SEO, uh, you know, CTV, retail media. You, you pick it all up and you can have a good conversation with people about it. But I've never been one who's been in the weeds working on these campaigns, really in the sort of the, the minutia, that detail thing, as forensic as possible. I've just been the person who's been selling this stuff. So I know enough about it to talk about it, talk about the services and channels. So when it comes to the thought of going to work in e-commerce or digital marketing for a brand where you have to be that person, that's when the imposter starts to rage a bit because I'm like, I don't know enough, how would I get on? But sales I'm very happy and comfortable with because that's people-based and it's about conversations and connection and partnership and relationships. And so that's where I feel I've gravitated towards, which lends itself well to the whole performance element, I suppose, in terms of being on stage. And putting myself out there.
You're a damn good musician as well, just so you know. I think the type of, the type of person they call that from a skill set perspective is like a T-shaped person, but I was reading this week, your T is now becoming an M. So you have to know enough about lots of different things to become dangerous. As you think about your team and the way that you have got to grow people now and train them and coach them and help them deal with all the modern challenges, is it markedly different from where you were back in the Periscopic season? When you just transitioned from Yahoo?
I think a lot of things remain the same. There's a lot more that we can do now with less, given the advent of technology. I still think people need people in this industry, regardless of technology and AI and all of these things. I think you still need a human interaction, a human touch. That age-old saying, people buy from people, is never more true. I truly believe in that. But it's really understanding people at the same time and that empathy that you can show to someone or, you know, understand where they're coming from and what they need and how they operate, what their motivations are. And look, I'm not saying I'm the greatest salesman in the world either. It's more a case of, you know, how can you make that connection? How can you show vulnerability? How can you— and that was true back then as it is now. You know, the goalposts might have shifted slightly, the technology's moved on, the products and services we sell have moved, but it's still about finding that connection. And it's often why I also leave this background up if I have calls rather than having a sort of corporate fuzzy background, because it can start a conversation with someone that's a guitarist or a musician, or they want to know what's the story behind me. And I find that useful, the sort of first 5 minutes at the start of a call, or even the last 5 minutes at the end of the call. Sometimes you get those sort of golden eggs or those nuggets of information or help you with that connection. So I a long answer there to your question, but yeah, lots of things have changed, but lots of things still stay the same.
It's interesting, even though your career choices, because you have navigated yourself very carefully, it feels like, into organizations that fit your own personality. You could have easily gone to more snake oil-based advertising agencies where, you know, it's all about growth and the customer doesn't really matter. How have you made those evaluated decisions for yourself, or how do you put yourself in the firing line over and over again, knowing that it all comes back to you?
Yeah, I guess you have to look at the— you spend so long in an industry and you know what companies are like, and you talk to a lot of people as well. And, you know, this last role, I'm there because, you know, I spoke to the MD and we had a good connection and we had very similar views on what needed to happen and what, you know, and it was a conversation that happened over a period of time, you know, so we synced up at that point, and I thought, yeah, this is— this guy is, you know, this guy's my cup of tea, you know, and I think this company could be my— where I could feel quite comfortable as well. I think you do that in each scenario. So, and you know, it's always a bit of a risk, isn't it, to jump into something new when you don't know with some new variables. But I think as long as you can tick off some of those boxes and then, you know, make the best of things, you'll— there'll be struggles, there'll be challenges along the way when you meet people and colleagues. And, you know, even now, one of the challenges we face now is that it's a good thing, but we're very much a remote company. So I miss being with a lot of my colleagues in the office all the time. I'm with colleagues in the office, but not— but compare that to previous roles where I've been in an office prior to COVID and everyone's there and everyone comes in 5 days a week and there's a lot of chat and there's a lot of that. That's That's where I thrive and I excel. I'm in a very busy office right now, but it's not quite the same. So, you know, pros and cons of both, I guess.
It's hard to underestimate that. And I've almost forgotten what that feeling is like to be in an office with people. But I remember back to your Yahoo days, you had a kind of a famous group of people that worked there, at least in my world. We had people like Team Sausage and all that group of people. How different was your attachment to the work because you felt attached as a team? And can you take us back to trying to establish what that feeling was like being in such a successful team at such a formative time in the industry?
Yeah, that was a fun team. I'd also caveat, I was very young and probably quite naive in terms of working life at the time as well. At that point, to me, it was just, it was a 9-to-5 job where I worked with some great people and had a lot of fun. It was only really when I transferred across to Periscopics after that, that I sort of, it clicked a bit and you're like, oh, right, this is how I have to apply myself now and work for it. Because it was just going through the motions, I think, back, back at Yahoo. And again, that's all on me because it was that naivety where I wasn't, I wasn't probably still ready for that, that sort of corporate environment.
Can I just pause you for a sec? Because the naivety almost feels like it was necessary within the industry because to a degree you didn't know where it was going or how this was shaping up and what it was going to look like. And the naivety was probably a mini superpower in a way.
Yeah, potentially. And it was an odd time because Google were becoming this huge force at that time at Yahoo, even though Yahoo had bought that company Overture who founded the paid search marketing.
Methodology? Methodology now though, that's where it is. Mythodol!
Mythology. But Google quickly took over and became far superior so at that point it was a struggle to— I keep using that word giving me on the struggle bus. It was a challenge to get agencies to listen to you because it was Yahoo we don't really care about Yahoo and search. Yahoo were doing great things in DR at the time and I think a lot of the team sort of transferred across there. Acquisition of Bright Media and Programmatic was kicking on, but it was, yeah, perhaps you're right. And naivety was a good thing, but the team were, you know, a super team who you and I both still speak to today. You know, that's your network, isn't it? There's lots of good friends in that team that are still in the industry and I consider good friends when I see them. So yeah, it's, but just going back to, I think when I went to Periscopics, it was it was certainly a wake-up call in terms of, okay, now this is serious. You have to really— but it was my first foray into proper direct sales versus channel sales, which is account management as it was back then. And so that's perhaps where I felt more comfortable and where I hopefully thrived a little bit more. And then that's where I've sort of been gravitating towards for the rest of my career more so.
And now you're at NP Digital and there's a much more structured environment for all of us when it comes to commerce and if you're an e-com manager now, be it on agency side or brand side, the requirement and skill set is, is so varied. The, the T-shaped person to me feels like they're more valuable than ever at this moment in time. What kind of things are you seeing on the front line? Like, what are you seeing on brand side? What are you seeing as being those, those key areas that people are unlocking to, to find ways forward?
That's a good question. I think I'm very lucky at NP because I'm surrounded by a lot of subject matter experts and very, very good people. I have very good colleagues around me that support me in this whole sales journey. Sales, whilst I have a sales title, everyone is always selling. So it's a team effort and everybody pulls together. I just sort of project manage the process in a way. But there's loads of ins and outs and within that I think being a T-shaped person is important because you've got to take a little step back sometimes and sort of figure out how things are working rather than just focusing completely on the sales. So you have to think about what this might mean for this brand or when you're listening to these calls that we do and trying to understand what the issues are and the challenges are, you have to really try and get underneath and into the mind and the headset of that person. That comes from asking a lot of questions. And the, the part to your question, which was, you know, what are you seeing now from brands? I think brands are, with the advent of AI and the way that people are finding people online, that is becoming a massive thing. So a lot of brands are coming to us either with some knowledge of marketing or having done this for a while, but now, now really struggling because this whole new world is happening. And how do they, how do they navigate that whole new world? And NP is, is famous at the moment, you know, a little plug here for helping customers with that whole new world. There's a few guys on the team that are absolutely in the weeds and really at the forefront of understanding how these LLMs are surfacing brands online. And it's becoming very complicated because you've got different LLMs and you've got different overviews inside the Googles and so on and so forth. And Google is not going away despite what everyone thinks. But it's how we— they've turned this search everywhere optimization now rather than search engine optimization. So it's just those How are people finding information online? It's everywhere. So how are you present everywhere? And that's what brands are trying to come to terms with, you know, what, how do I, how do I navigate this new world? So that's, that's hopefully where we're helping.
I think back to the heady days of growth in 2004 and so on in Yahoo when you were there, you, you were having similar client challenges, but there was always growth now. People are becoming search everywhere optimized because they have to, they have to survive. That must weigh on you as an agency with a greater deal of responsibility than ever. Or do you feel confident enough now with 20 years behind you that you can navigate these kind of choppy waters?
Yeah, I feel confident in navigating these waters. I think the industry is forever changing. So, you know, that's the, that's the constant. And it's a well-known phrase, isn't it? The only constant is change. Everything changes all the time. And so it's just how you adapt and how you work with it. But again, it's how you're being really honest with your prospects, your customers, your partners about that fact. And again, showing that vulnerability and saying, look, this is new to a lot of us. We seem to be ahead of the curve a little bit, but we're still learning. We're still learning this and we'll work on this together as a partnership. You know, we'll move through this and help you and guide you through this. But there's a lot that we don't know that you know, and a lot that you, you know, and vice versa. And so we have to rely on each other a lot. I think that's the basis of a really good partnership where you have that open and honest conversation at the start to say, we are in this together. Let's work through these challenges together and let's see what we come up with. And I think people are receptive to that. Certainly, you know, they want that growth, they want that. But if you can demonstrate that you know what you're doing, but also have that vulnerability, like I said, to say that, then that forms quite a strong bond.
And do you find then that when you're dealing with brands and particularly in your client base now, because it ranges from such small businesses right all the way up to the scale, that we are on the brand side or retailer side, we are better informed than ever because there's so much information out there, but so poor at assimilating that information into what it actually means for a business. Do you find that more challenging for you, or is it more enabling for a conversation to be able to allow someone to tell you the bit that they think they know? Like, like I used to pretend I used to know back in the day. How do you find that brands are picking up that information and utilizing it for better or worse?
I think it's tricky. Such a good question. I don't know if I have the right answers, but it's the, the landscape is so complicated. There's so much that a brand has to do now. You have to think about, as we said, you know, there's multiple channels to consider. There's, there's organic community management, you know, how is your brand talking to its customers online, not just in shops, or, you know, if you're an online-only retailer. You have to navigate logistics, you have to navigate, you know, where your, your, your products are, I guess. And I'm saying this for someone that has never worked in the brand, the, the what I've read and what I've seen, what I think. It's not just, you know, the digital marketing slice is just that, it's a slice of what someone in the brand has to think about. And so you've got to be a Swiss Army knife as a marketer inside the brand. You really have to know so many different things. And that's where you rely on agencies and experts to come in and say, right, you guys take care of that, help me out. You know, I'll work with you on this, but I've got to go and talk to my PR agency over here. I've got to go and talk to the guys that are running my customer data platform or my analytics team or my SEO or, you know, the mail drops, whoever's still doing those. Lots of people are, I think, because it still probably works. Or manning the front lines, the call centers, or, you know, returns, you know, understanding what the attribution is. We haven't got any attribution. Why does our data not match up? This is ridiculous. Go and get that agency. And there are so many things to think about. I've probably covered about 5% of them. So in answer to your question, very tricky. I think brands are probably finding this very, very hard to navigate at the moment. And it's and it's probably only going to get worse, I'd say, at the moment in terms of how things evolve, but maybe it gets better with the advent of technology and so on.
I love that you said it might get worse, and that's not necessarily a bad thing. It just means that the human connectivity part of it becomes more and more important. A couple of things you've said that I really like. One, you're one of the few people in relationships that talk about sales repeatedly because that's how you see your role, and you don't see sales a dirty word. So I really admire that as a quality in you. I've always thought that if you hold a mirror up to the agency world with the advent of Agentic and all the challenges that it's going to pose morally in our work lives, in our personal lives, and you hold that mirror up and project a few years out, what do you say to your colleagues in the agency world? Like, what are the values that you guys should be holding true and how should brands be thinking about people on agency side as well, because you just keep turning up year in, year out.
Yeah, we talk about this a lot actually. I actually talk about it with my wife too, about the advent of AI and the effect on our kids. And how are they going to navigate the world of university without cutting corners? I think AI is, you know, number one, it's not going anywhere. It's going to keep getting better and better and better. And I think it's right to embrace it. I think you can't just stick your head in the sand. You have to get on board and embrace it and use it for the right things. In the back of my mind when I'm using it, I'm always thinking, right, could I, is this, is this dumbing me down or is this actually a task that is just being done to help save me time? You know, can I, can I apply myself creatively here to this task and then use the AI to do the legwork so it's still my work? I think holding that mirror up to, to agencies now, I think there's a lot of tasks that are going to be, going to be Taken care of by AI. Okay. And then there's a school of thought that says, how do you get into an industry and learn if you don't start at the bottom and, you know, work your way through the quagmire of some of these daily, perhaps more laborious tasks? Because when you do that, I think you have a really good foundation to understand how systems work and how an agency and how a business works and what works for brands as well. So there's got to be the right balance, I guess, for agencies and for this technology. And for people. I do still think people will play a massive part because people ultimately don't want to just talk to screens. That's my biggest worry, that everyone just ends up behind a screen and we never go out and see each other anymore. You know, I look at it with my kids now on phones and it's just, it's a sort of mini crisis I have in my life where they're just, they're just, I tell them all the time, I say, put that down and I'll tell you the secret of life. And they're like, roll their eyes. What's the secret of life? And I say, yeah, I said this. Talking to people, get out, you will rise above the crop if you can get out and talk. And they're like, eww, and they go back to their phones again. And, you know, silly old dad, what does he know? So I think, you know, people still want to make those connections. I think people are yearning for them perhaps more than ever now. And so my, again, long-winded answer to you there is embrace AI, but don't forget where you came from.
It's an amazing answer. I'm going to use that with my kids after school today, by the way. I'll probably get the same short shrift of an answer. We're getting close to the end of the pod. I try to keep this to about 25 minutes. Uh, you've been incredibly gracious with your time, but I love your honest approach as always, James. You are a really good figurehead, I think, for agency landscape in the UK, anywhere in the world as well. I just think you've set such a high standard for yourself, and you're someone I always come back to for information, for fun, just to have a chat. I know we, we chat on and off throughout the year, which as I say to you, always makes my day better whenever we do. So look, I thank you for that. But two questions I gotta ask you before we end. First off, if your career was a song, what would it be today? You being the music man.
Oh, okay, that's a great question. That's a really great question. About 15 songs have just flooded my mind and I'm terrified now about choosing the right one.
You can, you can pick more than one if there's a few that represent you right now. Go for a few, I don't mind.
So look, I wouldn't say my, my career's had its ups and downs. And so there are a few songs out there that I think that, uh, always resonate with me because they have ups and downs in them. There's two in particular. Uh, one is Easy Like Sunday Morning by the Commodores. Always been a favorite song of mine because it's got a little bit of everything in it. You know, Lionel sings that so well. He's got such a brilliant soulful voice. Yeah. And there's an amazing guitar solo in there and there's a breakdown and the other instruments come in. And the other one I'd say on the, um, A song, there's a couple of songs by Queen. I think Bohemian Rhapsody by Queen and Freddie Mercury is, that's got everything. I mean, I say that has a bit of everything in it. It changes around, it moves backwards and forwards. It takes you to another place. It stops you in your tracks and you're then into a completely different song. Uh, so maybe that one too. And I think maybe most people's careers could, you could say the same thing and there is never a linear path, but things move around, things change. You have ups and you have downs, disappointments, regrets. Uh, you know, times when you think you could have done better, times when you're on top of the world. And maybe some of those songs encapsulate some of that a little bit with the, with the undulations.
You've just mentioned 3 or 4 other songs along the way. You can't see it now, but I have a Wayne's World hat behind me, uh, up on my wall. I have many name tags and hairnets. And the final question, James, why should we let you on the struggle bus? Why do you deserve to be here with us?
Well, I don't know really. I think life is a struggle.
This is a favorite, right?
Yeah, I think life is a struggle. Like you said, I've always enjoyed our chats. I wouldn't say I'm the world's best marketer, the world's best salesperson. So for me, that in essence is a struggle, you know, just struggling through life, struggling through what it means to work in an industry, in different incarnations of the industry as it changes, as it moves, learning the whole time. Learning from your colleagues, learning from people, learning from your customers, learning from everybody around you, and not always getting it right.
I hope you keep doing it the way you've always done it, James. You're one of the true gents of our industry. I'm going to leave us there in the struggle bus. James Ulmer, thank you so much for joining me today. I hope we get to speak again soon.
Thanks, mate. Likewise. Same back to you. Appreciate it.
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