The Dan Mason Hypothesis: Great Product Leaders Focus on Moving the Ball Forward

Dan Mason is a veteran Head of Product, coach and consultant based in NY who works with teams of all stages to develop great product managers and drive great outcomes, drawing on years of experience at organizations big and small, including ESPN, People Magazine, and Shutterstock. In this episode of the Product Science Podcast, we talk about how to take a pragmatic approach to product development in order to make sure you’re bridging the gap between an ideal product process and the realities of the organization you’re working in.

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Questions We Explore in This Episode

The Dan Mason Hypothesis: Great Product Leaders Focus on Moving the Ball ForwardWhat was Dan’s experience like developing for mobile before the iPhone? Why was working in early mobile development a “half-product” role? How did that lead him to a crossroads in his career? How did he separate his technical knowledge from the skill of knowing the customer? What were the challenges Dan faced in early mobile internet development at ESPN? How did ESPN’s MVNO (Mobile Virtual Network Operator) development assets factor into Dan’s work? What was it like working for an organization that had made a big bet that failed?

What are the dangers of an “if I like it everybody else going to like it” mentality for building new products? How was ESPN’s attitude of “fan first” development helpful for learning to build product well? How did Dan’s transition to an ad network give him new insights about customers? How is a product-guided process different from getting hired to build the thing someone else thought of?

How did an acquisition lead Dan into a corporate development role? How do you have to change your thinking when you’re looking at combining your assets with a new acquisition? How did this experience lead Dan back into product management? How many different types of roles and companies has Dan worked for? What is it like to build something brand new in a startup or as an outsider brought into an organization? How do you build a product culture?

What was Dan’s experience like being a product person at People? What do celebrity news and sports have in common? What is high volume publishing and how did that create challenges for Dan and his team? How did the transition to a digital newsroom change the landscape for publishers?

How does Dan’s diverse experience help him communicate with business leaders about market strategy? Why does he have a more sympathetic view towards organizations that work more traditionally? How do you work smartly in product when you need to adapt to a more traditional framework? How is the experience of being in product different in New York versus Silicon Valley? What does Dan focus on when he can’t have a “perfect” product process? How do you assess an organization’s tolerance for change? What happens when a business hasn’t backported Agile into their design process and what do you do about it?

Quotes From This Episode

“With my breadth of background, I’m able to see the patterns and be empathetic and generous about it. Companies develop the way that they do for a reason. They’re fundamentally being true to themselves in a lot of ways in terms of how they operate.” – Dan Mason

“You do have to accept sometimes that conditions may not be right here to build the perfect product or even do things the right way, but I can help these guys who understand their customers at some level, move the ball, right?” – Dan Mason

Be nice to yourself as you’re going through these things. You will feel exposed, you will feel like there’s something you did wrong. This is a particularly precarious point in people’s careers when they’re trying to go from being a junior product person to being a manager of managers or more. – Dan Mason


Holly Hester-Reilly: Hi, and welcome to the Product Science Podcast, where we’re helping startup founders and product leaders build high-growth products, teams, and companies through real conversations with people who have tried it and aren’t afraid to share lessons learnt from their failures along the way. I’m your host, Holly Hester-Reilly, founder and CEO of H2R Product Science.
Holly Hester-Reilly: This week on the Product Science Podcast, I’m excited to host Dan Mason. Dan and I met when we were both working at Shutterstock and have kept in touch since, and I’m excited to share with you a bit more about his perspective on product management and all the things he’s seen. So Dan, welcome.
Dan Mason: Hey, thanks so much for having me.
Holly Hester-Reilly: So why don’t you start by giving us a sort of 10,000 foot view of your product management journey and what you think about when you think about product.
Dan Mason: Okay, sure. Well, so I started as an engineer, so I was an engineer for seven years or so out of school. Towards the end of that, I kind of found myself at a crossroads as everybody does, and I actually had a really clear choice. I was, at that time, working in San Francisco and I was at a small company that had grown sort of from 30 to maybe 150 people. So things were going well, I was enjoying it. Honestly, I was looking to move back to New York, so that was part of the reason for the inflection point, but it also kind of brought up some bigger questions. Basically, was I going to double down on being a developer? In this case, I was a mobile guy, right?
Dan Mason: So back in the early days of mobile, it was all wild West, close to the metal. The tools were terrible, but the devices were really neat and you could do some cool stuff, but honestly, you learned to be an expert on the platforms. You didn’t really learn to be an expert in software development. That was kind of ancillary. And so if you ended up being a good software developer, it was kind of an accident. You were a mobile guy first, and so your job to come in to these companies was they wanted to build a smart phone app or a flip phone app for whatever the website they had. They really didn’t understand why. They just knew they needed to, right?
Dan Mason: So you kind of took on as being like this hired gun for a platform. You took on a half product role, because you had to be an expert in the customer. To some degree, you had to understand what people were trying to do with these things, you had to understand what’s possible because there were things that you just couldn’t do on a phone that you could do on a website, and you had to understand, to some degree, why you wouldn’t want to. You had to understand that there was a difference between what people were trying to do on their phones and what they were doing on the web.
Dan Mason: And so I was still a pure developer, but I did enough of that stuff and I had someone who was a product manager that sat next to me, but honestly, she was more online focused, so I was still sort of more focused on my particular platform and it gave me a really nice perspective maybe on what the product job could be without having to make that choice upfront. So I’d kind of seen both sides, but then I really felt like I did have to make a choice, right? This kind of mobile role was starting to disappear, the iPhone was about to come out. There was a notion that everything was going to be everywhere, and so the specialist role was dying in a good way.
Dan Mason: So for me, I had to make this choice, was I going to go even further down the development path and really just sort of learn the ins and outs of being a great developer, which was interesting, but that would’ve been a shift, it would’ve taken me some time and some effort just to even reeducate myself in that direction from having been such a specialist, or go in the direction of products and sort of acknowledge that it’s a good thing that I had the tech background? But it wasn’t the sole reason for being, right? It wasn’t that by being a techie, I sort of understood the customer. That was an extra effort that I had to put in.
Dan Mason: So I had two very concrete choices. I was either going to go to ESPN as a product guy but in their mobile group, sort of as a bridge. I was going to go and be a mobile product guy, but having had a lot of mobile tech background and having already sort of been in that world, or actually go to Google as a mobile engineer, which was a super interesting choice that in retrospect, my wallet would probably be happier if I’d chosen Google, but here we are.
Holly Hester-Reilly: Yeah.
Dan Mason: And ESPN turned out to be a fantastic place to work. So having had that particular choice really focused it for me. I knew that I had to go one direction or another. One of the reasons I think I sort of went for ESPN too was that I didn’t like the idea of not having had this specialist view of it, not having this exposure to the customer and to the problem and to having to think about why we’re doing stuff and not just what’s the appropriate way to build this app so that it works the best, which is still cool but just wasn’t where I think I wanted to focus all of my energy. So [crosstalk 00:04:52]-
Holly Hester-Reilly: Interesting.
Dan Mason: … product. But from there, it turned more into [inaudible] specialized. So during that time when I was at ESPN, it was still a mobile group, but I started to think more about the general things that run websites. In fact, the first product I worked on there really was the mobile website and not an app, which is where I lived for a number of years.
Dan Mason: And so stuff like analytics and ad servers, all of that was brand new to me, and I kind of looked at it and I said, “Well, look, in mobile, these things are all sort of young and crappy.” There was no good ad server on mobile web in 2007, right? There’s no good analytics package that actually measures people the right way. You’ve got carrier gateways that kill your cookies. There’s like almost no way to get a good read on what’s happening. And so I’ve put a lot of my juice while I was at ESPN just into trying to solve those problems because, for me, there were some holes in my knowledge. I couldn’t figure out what was going on, so I figured nobody else could either. That turned out to be a reasonable bet.
Holly Hester-Reilly: Tell me a little more about that. So you were building mobile websites or working on ESPN’s mobile website. Did it have to work on the iPhone or was it feature phones too, or what’s the sort of stage there?
Dan Mason: Yeah. So while I was there, this totally changed. So I got there in 2007 and the iPhone launched that year, right? So this was mostly a Blackberry world, but with a lot of flip phones. This was also coming in right after ESPN had done its MVNO, right? So ESPN had built its own flip phone and invested really heavily in the platform for that. So we still had that investment as well.
Dan Mason: So the cool thing about this group was that it had been spun up to sort of be this juggernaut. There was a tremendous amount of talent, there was new content being created for it, there was really smart guys on both the business and the tech side, but then when they shut down the MVNO, they were kind of left with all these assets and they said, Well, let’s just go repurpose these on all the other platforms that we weren’t previously as focused on.” And the mobile web was a really good sort of first space spot to put that.
Holly Hester-Reilly: I think there might’ve been an acronym in there, I’m not familiar with it, MBNO?
Dan Mason: Oh, right. Sorry. MVNO, so mobile virtual network operator.
Holly Hester-Reilly: Oh.
Dan Mason: I mean, today it’s like Boost Mobile and guys like that who were borrowing somebody else’s network. So ESPN and Disney Mobile at the time were both borrowing primarily Sprint’s network. And then, eventually, there was a big partnership with Verizon that came out of it. So this was the world where the network operators really had a lot of the cloud, and ESPN was coming in as a content provider and trying to sort of muscle in sideways.
Holly Hester-Reilly: Interesting. At this point, are there any content providers that try to run an MVNO, or they’re always separated now?
Dan Mason: No, not today. I mean, that’s one reason ESPN’s bet was so big and interesting, was the idea that you could get somebody to switch their phone plan just based on the fact that they wanted great sports, right? Great sports content on their phone. And back then, because the phones generally hadn’t really thought much about the content experience, it wasn’t crazy to think that if this is so much better, you’ve got these guys who are real sports junkies. I came in having been a sports fan for my whole life but not quite at the level of many of the ESPN guys. I understood that impulse.
Dan Mason: The thing that I think really didn’t work about it was just that there was such a huge effort involved in switching providers, people had family plans. So let’s say that the guy who wants the ESPN phone, his entire family wants to keep their phones. You had a bunch of barriers to entry pop up that people weren’t necessarily expecting. But the core of the idea of like sports is visceral for people and important to people in a way that means they always do want to be connected to it, this wasn’t a particularly connected world in a lot of ways at the time, so do the best job on sports and there’s going to be a loyalty factor there. People are going to be loyal to the brand, and they might even be loyal to a provider.
Holly Hester-Reilly: Yeah. I’m curious because one of the things I always love exploring is how big initiatives that have more risk, yet approved and then get built and then ultimately sometimes get killed. And so I’m curious, it sounds like… Were you there during the period where they stopped offering an MVNO?
Dan Mason: I was literally the first hire back into this group after, right?
Holly Hester-Reilly: Okay.
Dan Mason: So it was really interesting to come in and see all this stuff, see the group basically still intact, see the core of the app that they built, which was really awesome, especially for the time, and to even see that the mobile website at that time was one of the largest mobile websites in the world, still is, right? But back then, I think when I was there, it went from 15 to 30 million monthly uniques, which would be a big website today. Back then, it was gargantuan, right? And that wasn’t even the headline. The app was the headline for them. And so it was a chance to really work on a big brands that had taken a big swing and hadn’t 100% connected, but which still had built something of value, right?
Dan Mason: So the question really was, so what do we do with this? What do we do with this thing that we know has value? What do we do with this business that’s already going? And fundamentally, we paid a lot more attention to the mobile web, especially in those first couple of years there, just to sort of capitalize on the fact that when the iPhone came along… Remember, the iPhone didn’t have apps at first, right? That was Steve Jobs’ big thing, was no apps. And so we were one of the first app partners they had when they eventually did sort of go in the app development route, but we were building the mobile website that fundamentally was the top destination for sports on the iPhone and everything else. It was a really cool thing to kind of parachute into. I can’t say that I had this vision when I took the job, but it was a nice surprise.
Holly Hester-Reilly: Yeah. That sounds like an amazing experience to have, like a really transformational time in the world of technology and media and a great vantage point for it.
Dan Mason: Yeah. No, it really was. I also really appreciated how ESPN fundamentally was also a very, they called it fan centric, but it was customer centric. So everything was about, how do we serve the fan? Are we going to jeopardize a revenue stream that we have by delivering video on a phone that ordinarily you’d have to pay for it through cable provider? Yes, maybe, but there was a lot of pushing the envelope that happened there. I mean, ESPN was very smart about securing rights, which basically just said, “Look, we don’t know exactly where someone is going to want to watch this, but when I sign a rights deal, I’m going to ask for 20 platforms that I know about, as well as the rights for anything that hasn’t been invented yet under the theory that you were going to surround people with the idea that wherever you are, we are too.”
Dan Mason: That notion of like, at the very least, we weren’t held back from coming up, I think with new ideas if we thought people would like them and use them, sometimes you put the brakes on and be like, “Well, that really is a billion dollar revenue stream. You might want to slow down.” That did happen, but in a lot of cases, it was very much more, is this something people would like? And is this something people would use? And is this thinking from a customer perspective? It was a really cool thing.
Holly Hester-Reilly: Tell me how that… Was that sort of just in all the conversations, or are there any specific practices that you can talk about that they had to make sure that was part of it?
Dan Mason: Well, the interesting thing, and this is one place where I don’t think ESPN was perfect at this, because in a lot of ways, sports is one of those things where if you’re a sports fan, you think you know sports, right? And so by virtue of so many people at ESPN being sports fans, there was kind of a, “I’m building this for myself, and therefore, if I like it, everybody else is going to like it.” That wasn’t entirely wrong. There was something true to that, and fundamentally, I think ESPN had built a strong enough culture and DNA that more often than not, that worked. But then there were, back when I was there, we were doing focus groups. It wasn’t really these sort of one-on-one customer interviews. It was, get a room full of these guys together and show them something and watch them react. That was more the speed. But we also had, of the guys that we worked with, we had an external design firm that we worked with really closely, and part of the partnership was that they were all sports fans too, right? They got it.
Dan Mason: And so there was a very strong… You do need to be in the club. If you don’t understand how sports works and how it feels, that would be a liability, but then there was a little bit blinkers on when it came to maybe some other sports fan might see this differently. We did our best to respond to customer feedback and to keep on top of it, but that was always a risk.
Holly Hester-Reilly: Yeah, interesting. So how long did you stay there for?
Dan Mason: I was there for about three years. It really was just I think the perfect introduction to product in terms of, think about the customer first. I didn’t have to worry about building the brand. I think one of the hardest things is, you can have a great product idea, you can execute it well, you can talk to your customers and sort of create this thing that’s valuable, but if you don’t have a big brand to plug it into, the marketing piece can be really elusive, especially for people who start as tech people. You just don’t know what to do and you don’t always have a partner who does.
Dan Mason: So it was really cool that that was just not the problem at all. We had the brand, it was more like, what do we do so that somebody else doesn’t come along and eat our lunch, especially on these new platforms where it’s possible? If somebody had been the first out there with a great iPhone scores app, that might’ve been a real risk. ESPN is now behind for this core data that we had always owned before. It was testament to them that really didn’t happen.
Dan Mason: After that, I actually moved over to an ad network for a while. That was an interesting tie in because it was both a chance to work with a friend who I’d worked with before, and I’d worked really heavily while I was at ESPN on the ad side, sitting with the sales folks and understanding how they sold mobile at the time. It was largely a throw in for other deals, but there was an independent business growing there too. So going to an ad network was an interesting chance to kind of double down on something that I knew beyond mobile, beyond sports, that I knew was pretty portable. I was back in New York at this point and thinking about, “Hey, what am I going to do that’s going to give me longevity here?” And one of the things that popped out was advertising, and the other one, which I did a lot of on ESPN, was kind of analytics and big data.
Dan Mason: So the ad network was actually a really interesting sort of a… It was a really interesting chance to run the gamut of a couple of different types of jobs. So I came in there and I was basically the new product guy, right? And I started as, “Hey, we’ve got a core product that’s doing well. We need to figure out what’s next. We have this sales apparatus, we have this revenue, like we can afford to invest. What should we do?” It was a really awesome open-ended portfolio, right?
Holly Hester-Reilly: Yeah. I just want to say for a minute there, that is a really great position to be in.
Dan Mason: It is, it is.
Holly Hester-Reilly: I don’t think it’s very often that I come across product people who encounter that situation where they really are being expected to help guide it. I think it’s a big conflict for us, right? A lot of times we’re hired to build the thing someone else thought of, and then we have to convince them that maybe there’s other things to do. So.
Dan Mason: Yeah, yeah. No, it really was something. And yeah, there were seeds of some ideas there, but one of the things that we did was some work on mobile, which really the company hadn’t thought of at all, but sort of made sense for my background. So I brought a little bit of what I had to the table, and then used some of what they had.
Dan Mason: During that first year there, we did three totally different types of products, and when I was managing each of them, there was one that was fundamentally an in-house built with a small team that sat in New York with us and was a display ad unit, sort of an overlay toolbar thing that was pretty popular back then. Another was this sort of mobile skunkworks prototyping work, which resulted in a couple of patents and a little bit of sales activity, but in the end, we diddn’t build anything, and so just interesting discovery effort. And then the third one was basically a white label partnership. It was basically somebody else had this cool thing that we could traffic through our ad pixels and they didn’t have a commercial presence at all. They wanted to see if we could sell it.
Dan Mason: And so it was a really fascinating mix of pure R&D, a sort of a straight up normal bill, but with a fairly heavy, this was a global company, so there was a global rollout to do and just a lot of customer work, and then this partnership, which turned out to be the most fruitful of the three. It was something that we could sell with, I think, really, really strong results. We actually sold a lot of it to the auto industry. And then, at the end of it, we ended up basically faced with the choice of, should we double down on this partnership, either by buying the company that we’re partnered with or by building it ourselves? Is it interesting you have to do that, or is there another way for us to get this capability because we showed them that it had legs?
Dan Mason: As part of that, we actually met a company who was a slightly smaller competitor to the partner that we were working with, but fundamentally did the same thing, right? Same basic technical solution, no commercial footprint, at least knew not much of one, and a really great team who happen to be based in New York. And so that turned into an acquisition and I ended up being sort of the… I kind of rode in the second chair behind my boss who was kind of making the main case and then our general counsel who was doing the deal. But it was a really cool thing to have done this product work and then have it sort of turn into this broader strategic like, “Hey, how do we accelerate this? We really like what we’re seeing here” conversation.
Holly Hester-Reilly: Yeah. So you’re now officially the first person on the podcast to be on that side of an acquisition.
Dan Mason: I know.
Holly Hester-Reilly: Yeah, and that’s interesting. I will say I’ve been on that side of the exploration of an acquisition. Oh, no, I guess maybe Michel Feaster was on that side as well. Okay, first person this season.
Dan Mason: All right. Good.
Holly Hester-Reilly: Yeah. But in my case, we didn’t actually find a good one to acquire, so it didn’t get to go all the way through with it.
Dan Mason: Right.
Holly Hester-Reilly: That sounds exciting. It sounds really interesting. I bet there’s a lot of factors and variables, but it’s really cool that you were able to find something and make that work. How did it play out after that?
Dan Mason: Yeah. So it played out interestingly in that I ended up being sort of the onsite… And these guys were in New York, so bringing them over to our office and having to be part of the team happened relatively quickly, but I ended up basically being the top or sort of main connection between the two teams for the period of the integration, which lasted a few months. And then I actually had an opportunity after that to basically step into a Corp Dev role, which was really interesting in that it was the sort of logical next step for what I’d been doing with this acquisition and sort of this new product work, but was totally unfamiliar to me. I’d never been in the investment side, I hadn’t gone and been an associate for three years at some private equity fund. Usually, that’s what people do before they step into these Corp Dev roles.
Dan Mason: So for me, my entire background was engineering, engineering management, product management, and then sort of this relatively brief period as kind of a partnership manager, but it was a really fantastic opportunity. It put me basically in a seat next to the CEO, sitting with her and watching her, both talk to the board about our strategic opportunities, so I spent time with the board for the first time. It was a chance to build a framework for. Essentially, in ad tech, I think a lot of people have seen the Lumascape, the crazy array of companies that both used to exist and now exist in that world. Frankly, it was hard enough to understand what they did, let alone whether they would be valuable to you as a company, that we kind of had to build some of our own framework for this.
Dan Mason: So for me, it was just a really cool opportunity to think about these things in a totally different way. It was basically like, I’ve thought about this as a product manager looking at the market, I’ve thought about it as somebody looking at one particular opportunity to acquire something that I thought would turbocharge one of my own efforts, but now it was kind of like, think about what we have as a company, think about our portfolio and think about what we could do to it if we were to add certain assets, or sort of where are the opportunities? Where’s the blank space in the market?
Dan Mason: So I’ll be honest that I don’t think I was very good at it. I think that it was something that I was really interested in doing and it was something that I am thrilled that my CEO gave me opportunity to do, and just working with her was a treasure, but it was something where I was able to highlight a handful of things that I thought were interesting ideas. We kicked the tires on some partnerships that might’ve led somewhere eventually, but, especially in ad tech, a lot of this is about timing. Do you have the money you’d need to spend on one of these things? Is your stock worth anything? Is the company positioned in such a way where you can afford to sort of let these things play out? For the first acquisition we did, there was that time, but for future ones, I think the window had at least narrowed.
Dan Mason: Again, as a first time Corp Dev guy, I was just kind of watching all this go by and saying, “Oh, that’s interesting.” I didn’t really know what to do with it, but it was still just a fascinating experience, and I was really glad to have had it. But by the end of it, I’d kind of convinced myself and for that matter, I think my boss at the time too, the CEO, I’d sort of convinced myself that product was where I wanted to be. And after that, I ended up going back into product and really playing, I say, a handful of different types of roles over the years since.
Holly Hester-Reilly: Yeah. I think that’s really interesting. Sometimes we learn where we should be by trying something that we shouldn’t be, you know?
Dan Mason: Yeah. No, for sure.
Holly Hester-Reilly: Then we realize, “Okay, maybe I will go back over there. That’s actually more my style.”
Dan Mason: Yeah. And like when I, because I’ve done a couple of career path kind of presentations for various reasons and I’ve kind of visualized [inaudible] lanes, and for that matter, there’s a right side and a wrong side of the road. So for me, product is kind of the left lane going the right direction, and Corp Dev was like the right lane on the other side. I was like, “I can only be here for so long, and at some point, I’m going to die. So I should probably make my way back over across the median.”
Holly Hester-Reilly: Yeah. Oh, that’s interesting. Well, I know that you’ve actually done many things since then. So over the course of… I mean, let’s say we speed forward to where we are today, how many different types of roles and companies have you worked for?
Dan Mason: Yeah. So I mean, I think I’ve rotated, and let’s say in the last like 10 years, I’ve rotated through probably three main types of roles. One is come in and build something brand new, and this is either at tiny startups. I mean, I’ve been at a couple of 10-person startups. This is create a team or beg, borrow and steal, like turn the designer into UX or turn the intern into a research manager and do as much as you can. And so I’ve done that a couple of times, and it’s a lot of fun and it really is this chance to both, because the product culture doesn’t really generally exist, you’re creating something there. You’re trying to show people just by doing kind of what the example should be, what things should you think about, what kind of trade offs are good, bad or indifferent?
Dan Mason: So that’s a really thrilling role, but obviously it either is, you’re the first product guy at a tiny startup, or you’re maybe coming into a bigger company [inaudible] Shutterstock as someone with a different background, right? I came in to Shutterstock from the editorial world. And so I was one of the only people there who really understood it from a product side. We obviously had sellers who did, but there, that opportunity was to build something brand new but still, most of the times I’ve done it, it’s been kind of still on a shoe string. You don’t have sort of this brand new team, you don’t have yours to play with. You’re trying to stand something up and prove your worth.
Dan Mason: So that’s definitely one type of role. I’ve also come in and just taken over teams that are already in place, but fundamentally just need a leg up. It’s either air cover, or they need new skills, or they need just some time, space and encouragement. There’s a few different times I’ve done that and at various sized companies. So I came in and did that at People when I was there, at Time Inc when it was going through some stuff. I came in and did that at Crowdtap, which was a mid-sized MarTech company, and that’s what I’m doing now at Pond5 really as well, come in and just really help those teams that are in place.
Holly Hester-Reilly: Yeah. So I feel like I’ve never gotten to talk to you about your time at People. What was it like being a product person at People? What was that?
Dan Mason: Yeah. It was really interesting because one of the reasons that they were interested in me in the first place was, celebrity and sports have a lot in common. They looked at my ESPN background and said, “Okay, at least you understand how to cover events, you understand the fanaticism of some of these things, you understand how to both run a newsroom or sort of work with a newsroom who’s out there chasing things, and for that matter, then how to work with big [inaudible] sponsors, right? So all of that was, I think, really relevant to them, and it was a fantastic brand who knew exactly who it was, but who was going through just a tremendous amount of changing of people. Time Inc in the macro sense was. They just went off from Time Warner. The magazine industry in general was too.
Dan Mason: Although if you look at it, People was such a big brand. I mean, it was making a billion dollars a year when I was there. People is such a big magazine that if all you did was sell magazines to 80 year olds, or 50 year olds now and 80 year olds then, you can run this business for 30 years. It never dies. It slowly diminishes. It’s kind of like the AOL dial-up model, right? It never really dies, it’s always a good business for someone, but it doesn’t look like the growth businesses that everybody wants to own these days. It doesn’t look like a Facebook. The human costs are too high. Our sort of boogeyman, while we were there, were the three words, high volume publishing. High volume publishing was not our friend. It was this idea that it was never going to work to really craft a great story, it was just going to work to spray and pray. And that’s unfair because there were some people doing really amazing work and I think there still was a really great DNA there, but the pressure was high and it was hard to execute.
Holly Hester-Reilly: So for those of us who have not spent a lot of time in the editorial world, what exactly is high volume publishing?
Dan Mason: It’s really just the notion of, if you are the only game in town, and this goes for the big four networks back when there were only four, and it goes for magazines when that was the primary way people got their news and likewise newspapers, you have a certain number of column inches to fill, right? And you can plan that, and you can resource around it, and you can look months and years out, and fundamentally, you kind of know what you’re dealing with and you know what you have to do, right?
Dan Mason: High volume publishing was really just a reaction to, well, now we’re competing against both Facebook and… We weren’t calling it this back then, but fake news or sort of thinly sourced news. It was just a reaction to the fact that a digital newsroom in particular, didn’t have those same constraints. You really did have to out shout people. You had to be the loudest in the room as well as the best, and there were very few who could manage both. And this was true at ESPN too, although ESPN I think, fundamentally, it’s ramped up a lot of its good journalism, right? I think ESPN has invested in creating just a larger volume of good stuff at least on the digital side.
Dan Mason: But you can’t say the same thing more than a couple of ways in like the People context of what we put online, right? We had to create new vehicles that were fundamentally just brand new content. We had to create new sponsorship opportunities. We had to look at how to integrate commerce. The things that we were doing were in some ways easier to do from being a big brand, and in some ways, a lot harder. If the news is cheap and really where you’re spending your money is sort of iterating on how you sell the ads or how you sort of sponsor products and get merch sold, we did some of that too, but we also have this overhead of producing for the magazine and sort of making sure that everything was true to the brand. That was one case where I think there was some baggage with the brand. There were some big benefits, but there was some baggage as well.
Holly Hester-Reilly: Interesting. I’m struck as you tell me this by how much high level strategy, like strategy for large, lucrative operations you’ve seen in different venues. I’m curious sort of how you think about that now, and can you tell me about… Are there any times where you’ve come into a new company and realized that you had a lot more context for all the strategy decisions they’re making than their leaders did?
Dan Mason: Yeah. I mean, I don’t know if I’d go that far just because the thing that I think I do have is just a very probably unusually broad perspective, right? I’ve been in all types of companies and roles. And if I think about it, I was a developer, I was product, I was Corp Dev, I was a head of product, I have done B2B, B2C, B2B2C, enterprise, consumer, and I’ve done consulting versus full-time also, which is a pretty big distinction, especially for product people. What you can do as a consultant is very different than what you can do as a full-time. And I’ve also kind of split, not evenly, but pretty close between startups under 100, mid-sized between like 100 and maybe 300 or 400, and multinational, right? I’ve spent almost an equal amount of time in each.
Dan Mason: So I think it’s more that if I were to parachute into somewhere tomorrow, I would have a much better chance than anybody else of hitting the ground running, being able to see some of the patterns that are already there and being able to be empathetic and generous about it. These companies develop the way that they do for a reason, and they’re not doing anything wrong. They’re fundamentally being, I think, true to themselves in a lot of ways in terms of how they operate. And that’s one of the things that I think is really tough about product in general, right? It’s kind of a reflection of the company. The way product operates is generally how the company itself kind of likes to operate. You plan things on a yearly cycle, product has to work with that. It’s one of the reasons there’s so much tension. If the newsroom drives what you cover, product is usually there to help the newsroom. That’s certainly the way it is in media.
Dan Mason: I remember this great conversations with the head of ESPN’s newsroom. He was a great guy, and he was basically like, “Look, you guys do whatever you want. Just don’t tell me how to cover the news. That was all he really cared about, was that he covered the news the way that he thought was appropriate, and he was totally right to want that. And for us, it was about providing frameworks that they could use. And so I think with all of these companies, you come in and you see patterns, and very few companies have a completely special snowflake kind of problem. They do exist, but it’s unusual. Most companies are acting the way they act for very good reasons, and they’re reasons that if you sort of peel the onion, you can figure out.
Dan Mason: I think also that’s the reason why for me, at least, I think there are cases where product can run off a certain playbook. I love Marty Cagan and his insights. I worked with him at Vibrant, and it was just fantastic. It was one of the nicest weeks I had. I’ve taken those with me, but I think, and even I think Marty would say, it’s not that these things work the same way everywhere. There are principles that are important, but product is really adaptable smart people who kind of know where true North is and understand that you’re trying to solve a problem for somebody on the other end, a customer, and have a nice bag of tricks that they can deploy at will. That’s really what I think good product people who are horizontally applicable have to do.
Dan Mason: There are people just go in, and I think, again, in the valley, there is, I think more of a culture of product has sort of set in as this discipline you go from company to company, and there may be differences, but it’s not nearly the sea changes that you’ll find walking across the street in New York. New York is a totally different place when it comes to what product means at every company. And so for me, that’s where I spend most of my career and that’s kind of how I’ve adapted to it.
Holly Hester-Reilly: Yeah. And I know that there was a moment in my career where I found myself pulling aside other product people in my new company and asking them if I had any idea what product meant there, like, “What is product to you? Wait, what is product to you? What? All right. Whoa, mind blown.” I totally thought we all thought it was the same thing, you know?
Dan Mason: Yeah.
Holly Hester-Reilly: So I think… Yeah. One of the things that’s always struck me about you that hearing more of your history helps me understand, is you seem to be very… I mean, you appear to be very at peace with it all. Like you often, you’re like, “Okay. Well, this is a thing that happens. That’s a thing that happens. Yeah, they created that. It’s okay.” And it’s like, okay, well, you’ve been through a bunch of different storms and now you know how to get through the next one.
Dan Mason: No, I appreciate that, and I would say that very little surprises me at this point. So that’s a good thing. It’s really interesting. I think it sounds too pretentious to say that I’m a student of these cultures and these companies, but that’s kind of how I feel. I love watching these things happen and helping any way I can, and again, understanding that people don’t hire you unless it’s really a slash and burn kind of environment, people don’t hire you to come in and install something. They don’t hire you to come and install process. They don’t hire you to completely change the way they work, even if they say that’s what they want, right? They’re hiring you to help them get a better outcome. They’re hiring you to help keep stuff off their plate that they don’t otherwise either know how to deal with or want to deal with. They’re asking you to help improve their lives.
Dan Mason: I think that’s a tension with the notion of building a great product a lot of the time. I think that’s maybe the hard part, is you do have to accept sometimes that conditions may not be right here to build the perfect product and to, in fact, even sort of do things the right way, but I can help these guys, who are otherwise good people who understand their customers at some level, move the ball, right? That’s really what I’m trying to do, is help them move the ball, and you just have to balance that against, if all you focus on is moving the ball, you’ll start doing dumb stuff and you’ll forget maybe some of the higher principles. So that balance is really hard to do, but I think it’s something that you have to assess at every company, what their real tolerance is for change.
Dan Mason: For me as a consultant, I had a ton of fun consulting and I look forward to doing it again just because it really is such a freeing vibe. I think I might have told you this, but I went into my first big consulting client, and it was the funniest interview because it was basically like… I had already sort of talked to some people and gotten the high level green light on this kind of makes sense, but then I met one of the final stake holders and he basically just asked me three questions. It was along the lines of, “Have you done this before? Do you want to do it again? And are you prepared for the way that this place works?” And I was basically like, “Yes, sure, and yeah, I’ve worked places like this before, so I get it.” And I have empathy, right? That was really what he was getting at was, do I have empathy for the way that they work? And can I figure out a way to operate within those bounds? I think it’s important and it’s something that not everybody can do because it does require real compromise.
Holly Hester-Reilly: Yeah. Yeah, it does. But I think it’s… I love the speed of learning that we get when we do go into different projects regularly as a consultant and how we have the opportunity to bring those different insights and situations back to others.
Dan Mason: Yeah, absolutely.
Holly Hester-Reilly: I think one of the things that you said that stood out to me was about, sort of like, you don’t see a lot of problems you haven’t seen before. The companies aren’t usually really totally special snowflakes. I think that’s something that also was… When I talk to people who are in different stages of their career, I’d love to have more people like yourself be sharing the things that you understand when you get to the point where you’re now like, “Okay, wait, I’ve seen that before in that form, or I’ve seen that before in that form.” There really are these emergent properties that develop and I know there’s a lot of really interesting academic work around organizational design and development and psychology within organizations, but they don’t particularly bring it alive in terms of the product and tech side of things. I think it’s something that remains to be done. I think we could do more.
Holly Hester-Reilly: Are there any sort of… I don’t know. What is the problem you hate the most? What’s the thing when you get there you’re like, “Oh, it’s that one.”?
Dan Mason: Well, I think it’s the hardest thing to deal with, is when there’s a real mismatch between the way the team operates or wants to operate, and the way the company sort of conceives of itself as operating, right? If there’s a gulf between the executive leadership and the team on just fundamentally like, hey, how often should we prioritize? How do we want to talk about our roadmaps and our goals? How much freedom am I willing to give you versus do I need you to make sure that you take, right? Because I’ve seen two counterpoints and I won’t name names, but on the one hand, there was a CEO who really wanted to let go, right? Really, really wanted his teams to step up and fundamentally run their own roadmaps. That was the way he was used to. And when there was weakness in those teams, he had to step in and it felt weird to him, right? And he was eager to sort of have this fixed, right?
Dan Mason: And so my role when I came on was I was like, “Okay, I can help with that. I can help these guys become more autonomous. I can help develop rituals and rhythms that will really just help them start producing again and help them elevate the things that they want to do back to the level where you’re at, so that you don’t have to bring a spreadsheet of your top priorities and have them react.”
Dan Mason: Likewise, I’ve seen the exact opposite, teams which are fundamentally pretty autonomous in doing great work and an executive layer which really wants to pull the strings. It is not always wrong to want to pull the strings, but when you have that mismatch, that’s where the tension is. If everybody wants to be waterfall, be waterfall. It doesn’t kill you. It’s not necessarily the best way to run a lot of businesses, but you can get a long way by carefully considering which projects you do and doing them. You, on the other hand, you’re going to get a lot more out of certainly early stage things and nimble stitched situations by being more agile, and a lot of people kind of try to split the difference.
Dan Mason: So I actually wrote a kind of a long blog post and I think not even published yet, just about how the mismatch between agile upfront sort of development… Well, it’s not even that, the difference between what’s fundamentally a waterfall design process then paired with an agile dev, right? You spend all this time getting buy-in from design, and UX, and the business layer, and the stakeholders on what it is that you should build, and then you send it to devs who have to then break it down into 19 equally-sized sprints, right? You end up doing so much work upfront, decomposing it all, and then when you start actually building it, you realize a lot of your design choices weren’t perfect, and so you go back and you try to adapt them. But because people think about agile dev as being kind of the gold standard, but they haven’t really backported it all the way into their product and their design functions, it just causes so much pain and so much wasted effort. So that’s probably the main pain point. I think that’s what you’re asking, right?
Holly Hester-Reilly: Yeah, absolutely, and I hear you on that one too. When there’s a gulf between any kind of teams like that, it is painful no matter who’s on what side.
Dan Mason: Yeah.
Holly Hester-Reilly: So I think it’s about time for us to wrap up. I’d love to ask if you have sort of a final…If you were talking to yourself 10 years ago, what would you tell yourself?
Dan Mason: Yeah. Well, I think one thing that I’ve definitely tried to learn over time is to be… I mean, in general, I think this is true, just to be nice to myself. You tend to second guess your decisions a lot, especially when you’re kind of walking a high wire, like having a product job. It’s a very precarious position, and we ask just a tremendous amount of, especially junior product people. So actually, I’ve been reading all of Marty’s latest stuff about the role of the manager of product managers being like the single most important thing. It’s 100% true, right? Because you are the person who is going to help all of these people for whom the world is like on their shoulders, right? They have to have this perfect command of some huge problem space, they have to know exactly what the customer thinks, and they fundamentally have to, maybe with help but maybe not, predict timelines and do roadmaps, and they’re doing all of this with almost no work support. Almost no place is really set up to support product managers well.
Dan Mason: And so you’re putting more pressure on this random dude sitting at the bottom of your org chart that you are probably on your CFO. At least he knows what his job is, at least it doesn’t change day to day. Sure, there’s a lot to do, but he has help, and we just put so much on these people. And so the hard thing I think about the job that I’ve been doing in general is that you end up being this middleman between knowing how hard the job of the people that work for you is and knowing how much the executive layer and the company needs from you, and knowing that neither side is unreasonable. It’s really just that bridging that gap is really tough. And because most companies aren’t really set up to do this all that well, you end up burning people out. You give the job to somebody who’s basically a polymath who can do anything, but at the same time, you ask them to do too much, and they fumble. It’s really hard to do that job well, and very few places have the support that you need and also sort of allow people to develop in good time, right?
Dan Mason: If you have the spotlight on you, some people that brings out the best, most people it’s the magnifying glass on the ant, right? You end up on fire. There’s almost no way to do that job that is both a good outcome for the company and for you as an employee and as someone growing in your career.
Dan Mason: So that’s what I would say, is just that you always have to remember: a) to be nice to yourself as you’re going through these things. You will feel exposed, you will feel like there’s something you did wrong, and of course, we all should admit we do things wrong all the time. We need to learn from them. But this is just a particularly precarious sort of point in people’s career when they’re trying to go from being a junior product person to being a manager or managers, and then eventually to being more than that. It’s a very hard chasm to cross.
Holly Hester-Reilly: Yeah. Well, my younger self felt calmer after that.
Dan Mason: I’m glad to hear that.
Holly Hester-Reilly: How can people get in touch with you if they’d like to follow you?
Dan Mason: Well, probably the best place to contact me is on LinkedIn. I am starting to try to write a little bit, and I’ll put some of that stuff on Medium and I’ll try to publicize it when it pops up, but fundamentally, I’ve not been particularly out there. I’m one of those guys who’s on Twitter, but doesn’t tweet. So that is what it is, and I like it that way, but I’ll try to start putting more of this stuff out there over time.
Holly Hester-Reilly: All right. Well, that sounds great. I look forward to it. Thanks so much for your time today, Dan.
Dan Mason: Hey, this was great. Thanks so much for having me.
Holly Hester-Reilly: Of course.
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