Episode 6: Workweek CEO Adam Ryan on Telling the Truth in Entrepreneurship and B2B Marketing
Host: Joe Zappa
Guest: Adam Ryan, CEO of Workweek
Length: 48 minutes
Published: August 17, 2026
Workweek CEO Adam Ryan joins the podcast to discuss the roots of entrepreneurship including struggling in school and competing in sports, learning to confront failure and tell the truth, using AI to iterate faster and get closer to the customer, overcoming the fear of writing unpopular posts, and evaluating B2B marketing based on who, not how many people, you reach.
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Full Transcript
Joe: Welcome to the AdTech Marketing Podcast, the only podcast devoted to the very niche topic of adtech marketing. I am joined today by someone who also inhabits that niche, or at least an adjacent one, Adam Ryan, the CEO and co-founder of Workweek. How's it going, Adam?
Adam: Hey, Joe. Thanks for having me on, and, uh, glad our Twitter, uh, of co-follows and, uh, co-likes is, is now bringing us to this podcast.
Joe: Adam, you are one of the other five people on the internet who talks about B2B social and marketing and what not in. I often just read your posts on Twitter, and I'm like, "Yes, that is exactly it. That is the thing I was going to post today" So this was inevitable.
Adam: I'm glad we can talk circles around each other, and hopefully, uh, this one, uh, amplifies the message a little bit further.
Joe: So one of the conceits of this pod which, of course, as a millennial entrepreneur and a man who formerly lived in Brooklyn, I have multiple podcasts, and, uh, one of the conceits of this one in particular was that, like, human content is going to be more valuable than ever. And actually, over the weekend, I was listening to the Howard Schultz episode of Acquired, or re-listening to it. You know Acquired, they usually don't have the entrepreneur on, but in this case he came on they spoke for over three hours about Starbucks. And I'm listening to this thing and I'm like, "You know, I listened to this once before, and it made such a big impression on me. Why am I so into it?" I was listening for, like, the business lessons that make it so valuable, and then I realized like in hour three, I was like, "Oh, no, it's obviously not the business lessons." Like, anyone can share these lessons. It's that, like, I feel Howard Schultz's, like, soul, you know, when I listen to this. Like, I hear his journey and how he grew up and, like, where he is. And so I've been thinking a lot more about that in the pod, and that brings me to my first question, which is I wanted to know for you, when you think back to, like, how you grew up and the long path leading to ultimately becoming an entrepreneur, what do you see sort of in your, like, early life that you could draw a connected line from there to now?
Adam: Howard Schultz is also my favorite CEO ever, so, uh, what an opening for me. Everyone in our office will be like, "You intertwined Starbucks. Uh, this, this, this podcast was meant for you." There are so many things that I think with reflection. In the moment, you don't know, right? You're going through so many things.
I was a terrible student, and I have terrible ADHD, couldn't sit still in class. Always wanted to be in competitive sports and did that, and there was so much of this kind of interesting aspect where, like, during the day, I always felt like I was failing, and then at 3:00 to 6:00, I was always, like, winning. And I feel like that's entrepreneurship to the T.
Like, I never felt like I was doing well in school, but then, like, I'd get accolades, and our teams were winning and doing all these things, and it was this, like, way I had to almost, like, learn how to justify and also, like, recognize, like, man, I can't win at all these things, but I'm kinda good at this thing, so let's, like, keep doubling down on what you're good at. And I think that's, that's a part of it. Like most people, also the chip on the shoulder, learning how to go through bullying or divorced parent. Like, anything kind of adversarial, that I, I had both of those things, uh, happen, and, like, that teaches you how to just- kind of like go with the punches.
And then when I got to college, I was walking past the business school for the summer welcome, and my mom was a nurse and, but she didn't go to a four-year traditional college, and she just went to a nursing school. And we were walking past the business school, and she's like, "Adam, what do they do with business degrees?" And I was like, "Mom, I have no idea." And she's like, "Well, what do you wanna do?" And my uncle was a football coach and teacher, and I was like, "I guess I'm gonna become a teacher." And that whole kind of, like, journey, I think is, like, you only can deal with the cards that you're dealt, but also, you just have to be curious.
And I went from teaching to getting a marketing internship with, uh, Procter & Gamble, and I was like, "Wow, this is way more fun than teaching ninth graders about the judicial system." And that, that kind of kept it going until finally my, my senior year, I, I started finding different things that I really found passionate about and then started to pursue those more.
Joe: So you mentioned that when you were a kid, you actually weren't natural academically in school. A lot of entrepreneurs have that experience. Mine was actually very different, which I'll, I'll get into eventually. But did you have the thing that, like, some kids who aren't academically inclined have, where you're like, "Oh, no, like am I, am I dumb?" And then you're like, you know, or were you kinda like, "Oh, this isn't my thing, but I feel like I'm smart. I just don't like this setting"? Like, how'd that evolve for you?
Adam: You know, I have to give my parents, like, tons of credit. I definitely felt my, uh, my middle school separated us out into three tracks. There was basically, like, what would be in layer, like AP honors, and then everyone else, and then, like, remedial, like, with, like, there was, like, 10 of us. And I was in remedial.
And I remember, like, looking around, being like, "I don't think I belong in this group of people." But, like, after a while, you're kinda, like, told that at school, you believe it, but my parents never let me believe that I was dumb. They didn't believe that I was dumb.
They always believed I had a hard time following through on things and all the other conditions that happen with, when you have terrible ADHD, but I never believed in my, like, soul that I was dumb, and I, I saw it, like, in spurts. Like, I always had a, I was always really good at math. I had this, like, passion for history and, like, learning things and, and tinkering and building stuff.
And so I, started writing a newsletter when I was, like, in seventh grade, uh, that was physical. Like an actual news thing. And I just, like, always had stuff that didn't make me feel stupid, and I think that was, like, my protection of, of my parents really helped me do that.
But yeah, I mean, I remember I was in student government in high school, and we were the only ones that were allowed to know the rankings of our class 'cause we gave out the student of the year awards, and I was, like, 252 out of 270, and everyone else in the whole student government was, like, top, like, 15. And I was like Am I, am I like that dumb? Like, what, what, what? And, uh, you know, and, and I also... But it was this, this thing where I, I also, like, lear- learned is, like, the room that you're in, both, like, in how you see yourself, but also, like, how you can build confidence in. I think that was... It was definitely something I battled for a long time, and then I later kind of learned that, like, you just had to check the box and go through life sometimes like, "Hey, in order for people not to think you're dumb, like, go get a master's degree." So that's what I did.
I was like, "I was terrible in school, but I'm gonna get a master's degree so no one ever thinks I'm dumb." And, like, that's just sometimes the things that you have to do in life, and I think I learned that through, through my struggles in, in school.
Joe: And then what was it like when you got into sports? And you mentioned you were, you had more of a natural aptitude there, and you sort of fit into the structure. Were you super competitive? Like, did you love winning?
Adam: Absolutely competitive. I have a story where my sophomore year of high school, I started showing up to work out in the morning at school. Our varsity football coach would get there at, like, 6:30 in the morning. So I started getting there at 6:30 in the morning, and he didn't like to be beat. So then he got there at, like, 6:25, and then I got there at, like, 6:20. And by the time I was a senior in high school, I was at my school at 5:00 a.m., and he was there by, like, 4:40. Like, impossibly early. And it was just like this, like, innate thing of like, "Yeah, I can do that. I'll play that game. Let's go." Uh, and also, like, I wanna win, and I think it also... With school, I learned, like, no matter how hard I tried, I was gonna suck on a test. I just believed it. I just, like, thought that. I had, I couldn't sit down for two hours and take a test.
But I, I learned in sports, like, the harder you work, actually the more success you can have, and I, I think that helped a lot. One of the values at Workweek is, like, create competition everywhere. I just, like, I think, I think life's more fun when you're competing about things, and, uh, and there's a reason why the four-minute mile just kept getting broken and broken. Like, I think human nature is to look at people to your left and right and try to beat them.
Joe: I totally agree. I, I love competitiveness as a value. So it's funny, um, like, there are a lot of similarities in our childhoods, but then the venue we found to exercise our competitive drive was different because I actually loved school. I was just, like, a huge nerd. It came really naturally to me. I was like, I... When I started to really love it was when we started competing at things because I was like, "Oh, we're gonna see who can do the times tables the fastest," and I'm like, "I'm gonna do these times tables the fastest of everyone in this school, and you all are gonna know that." And, like, I'm taking the crown. We're gonna, we're gonna fight over that. And that was basically my whole childhood was, like, exercising the same competitive drive, but in the, in the classroom.
But it's a very common story, right? It's very common that entrepreneurs didn't, like, find school natural, or they didn't sort of fit into the academic box. And I think what's, what's common to any entrepreneur's story is that you have a certain talent, and you have a certain competitiveness that might manifest in school sports, wherever. But you have to sort of go, like, outside the box. So I would say, for example, even you showing up at, like, 5:00 a.m., that's going outside the box, right?
That's like, you could have just done, like, the normal, like, varsity athlete thing or whatever, but you were like, "I'm gonna find sort of this other thing I can do that is not expected of me, where I'll, like, I'm gonna excel and sort of exercise my drive." And same thing with starting, you know, the newsletter when you were, I think you said seventh grade. So I have a lot of those things. For me, it was more in the academic arena. But it was like, "You're telling me I can take three APs," and, like, I'm gonna take four, right? Or like, I'm doing this class, but, like, I'm gonna, like, go find this other thing I can do that you didn't know, like, anyone in the school could do.
So it's like, we have that sort of experience of, like, we're not very good with authority generally.
Adam: Yeah.
Joe: And we're like, "I'm gonna find this new place to, to pursue my passions."
Adam: Well, that was, uh, probably the best lesson I heard, I learned, uh, my sophomore year. I was taking a Spanish class, and I was not gonna pass. And I went to a college preparatory high school. It was, like, unusual for how bad I was doing in school, and everyone was all concerned. And, and my parents were told basically, like, "You have to get him a tutor. Like, you have to find him a tutor to help him learn Spanish." On the second lesson with this tutor, I will never forget this conversation. It changed basically my whole view of life. She looked at me, and she, like, she was probably, like, 20-something years, like, very young. She looked at me, and she, like, looked around to make sure my parents couldn't hear, and she's like, "I just need to tell you the truth. You are absolutely not gonna pass this class. And, like, there's no way that you're gonna pass this class. And what you need to do is walk up to your teacher tomorrow and very politely be like, 'I recognize I'm not going to pass this class. What do I need to do to get a C? And then do exactly what they tell you to do." And I did that exact thing the next day. They were basically like, "Quit falling asleep in class. Do these things. Do this thing, and we'll see what happens at the end of the semester." And I did that, and I got a C that I did not deserve. And I think the other aspect of, like, failure is you learn this way out of it and on the flip side of competitiveness and, you know, I, I kind of, that was my, I like to tell people that was, like, my first sales close of my life of like, "Huh, I guess I'll walk up to my teacher and basically say, like, 'I need this thing. What can I do to get it done?'" You don't go through that when life comes easy at you or if you're not competitive or going for the next thing. I think that's, it's, it's, it doesn't feel like a blessing at the time, but it definitely is.
Joe: Mm. Something in that story really touches me, and I think it's about, like, honesty, right?
Like- Yeah ... there's something very cool about... I guess what I loved about school as a kid and what I now love about entrepreneurship is, like, I've been thinking over this phrase, which is like, it tells you the truth in a way. Like, it's like there's a scorecard, right? There's a report card. And so it's like, it's the hardest thing, but also the best thing about business is that, like, I also did grad school. You mentioned doing your master's. Like, I did a, I did a PhD in literature. And, like, dude, that is so full of bullshit It's just like there's no objectivity. It's like everyone kinda knows like who's better at writing or whatever, but it's like, eh, ultimately they just kinda pass you through, and like some professors give you a hard time and some lavish praise on you, and it just like, it all feels like convoluted like bullshit. And there's something about that story where it's just like someone having the honesty to like, and the accountability level with you and be like, "I'm your tutor. My job is to help you pass this, but I just gotta be honest, bro, it's not gonna happen."
Adam: So and we kept meeting, we kept meeting, by the way. We, she, she, she kept, she kept collecting the check, and I was like, "All right. Yeah, sure." I actually think though like on the flip side of that too, I later became a teacher. So I got my undergrad in, in education as my, after we walked past the business school, and I was like, "I, I don't know what to do," I was like, "Well, I know what you do with an education degree." And so I, I, I got my undergrad and then my master's in, in education. And I always thought there was this like faux relationship between student and teacher. Like, you know, you see Miss Robinson in the grocery store, you're like amazed who she is, right? But like that exists in the classroom, and there's just like not this honesty of like, "Hey, I'm doing my best as a teacher. I need you to do your best. And like together we're probably not gonna actually show up the best every day. Like, but let's- let's like try to make progress." And that like kind of value around you get way more out of what you want when you tell the truth. It's way harder sometimes, and it's carried with me.
I mean, and I think that's why, I mean, I did fall in love with advertising is I was like, "Wow, everyone lies in this industry. If you like tell the truth, you probably can get pretty far."
And like it, it was kinda the same pattern recognition I have with teaching where I was like, "All of you teachers are just like subconsciously lying to your students about what you expect out of them. Like, be honest. They're 14." And there's a value of, of honesty that I think not only helps you sleep good at night and, and feels like you're, you're a good person, um, and doing the right thing in the world, but also that vulnerability like creates buy-in across the board and, and helps, helps you kind of get further, I think.
Joe: Leveling with people, I agree, is something that is very rare in education. Like, there's this sense that like students, it's like, okay, well, we're all aiming for A's. But it's like, again, I guess like especially in public school or whatever, right, like or probably in any school, like teachers, they can't go to a kid and just be like, "Look, man, you're not gonna get an A+ in this class."
"But like, like now you're at first test, you're at a C. What we're gonna see is can we get you to a B or a B+, right?" And it's like that is, I know the mentality I try to bring to business is like with my team, it's like if we're talking about a failure, and some people really struggle to understand this because they're used to this mentality of like sorta punishing failure and sort of the lack of honesty and whatever, I'm like, look, if we're talking about what went wrong in H1, right? We're talking it's August. So like let's say we're analyzing H1. We're looking at the data. We're getting the cold, hard evidence as to what we did well and what we did wrong. If we're looking at what we did wrong, I'm really never coming from a place of like self-flagellation or like flagellating others, right? I'm really coming from a place of like we did this, this was the result, right? Maybe we got a C on the test. All right, how do we get a B? And then how do, over time, how do we turn the B into an A?
I mean, essentially what we're talking about is every workplace, if you look at the values, they all say they care about like accountability, right? Accountability's really effing hard. That's why like everyone says they care about it because it's so important but so elusive. But I think it's, it's this ability to level with yourself that makes it possible, and I think that to level with yourself, you have to have this acceptance of like we're on a long journey here, and we're like in, you know, stage two, and we're trying to get to the end, stage 10. And like we're just trying to improve from one stage to the next, 'cause then you give yourself the permission to be honest about where you're at, which for most of us probably isn't anywhere near as good as we ultimately wanna be.
Adam: And I think there's the other kind of aspect of entrepreneur and business that I think school does like an awful job- um, the education system does an awful job of is it's like a natural apples to apples rubric, which then creates failures of like or, you know-worse than better. And like that is how the business world works, but the, the difference is like failure to the person who has dyslexia and all of a sudden gets a B in spelling is not failure. They're like, they did it. Or the person that never could finish a six-hour test and like passes. And I think like it requires to kind of be an entrepreneur is this ability to like find competitiveness to the person to your left and right, but not to compare yourself and recognize that failure is literally only what's in your own head. Rarely do you make a decision in your business that you're like, "We're out of money." Like that's like a, that-that is failure. Failure is like I didn't meet my own expectations. I didn't do the thing that I wanted to do. And I think school does a really bad job of that where it doesn't, you actually like are reliant on extrinsic motivation versus intrinsic. And then when you get into business, you're like, if you're someone that like is only looking externally of like benchmarking, you're screwed because like you don't know what path you're on and you're not listening then to yourself and your customers.
And I think for people that, I think some of the reasons why people that struggled in school tend to do better is you have to learn to like be motivated by your own being and create your own goals versus being like, "No, I'm not gonna get an A in that class. It's never gonna happen. But my teacher told me I can't fall asleep anymore, and she'll give me a C. Like not falling asleep every day is a win." And I think that is a little bit of how I, I see entrepreneurship is like you have to wake up and just like wanna be the best version of what you can possibly do and then like occasionally be like, "Okay, this person to my left and right are doing that. I can do it too." But there's a, there's a difference of like creating these goals that just are, they're made up. They're not possible. And then you kind of like ruin the momentum and morale, I think, of your, of your team.
I think as anybody that's failed in school knows, like, it's just such a demoralizing thing when you, like, see things posted and you're like, "That's not actually, like, something that applies to me." And that's, that's, uh, I think something that we, we try to carry now, uh, as, as we operate the business.
Joe: I am competitive, and as I said, like, when I was really young, some of my first meaningful memories are about competition. But fundamentally, I am competitive with myself, right? And sometimes you, you no doubt go through this in business, right? Like, people will be like, "Oh, such and such entrepreneur is like, you know, whatever. They sold a company for two hundred million dollars, or they did whatever impressive thing." They're like, "Doesn't that drive you crazy?" And I'm like, "Eh, not really, honestly." Like, they're on their journey, and I'm on mine.
Adam: Yeah
Joe: I'm just here. Like, I'm trying to get better. What drives me insane is if I'm not getting better. If H2 is worse than H1, then I'm really pissed, right? Because I'm trying to constantly interrogate what I could do better and improve those things so that I'm on an upward trajectory for myself. But it doesn't bother me if, like, someone else out there has some, like, crazily impressive story. I'm like, "That's awesome," and, you know, maybe one day I'll play on that level, and it's just about, like, improving my own levels over time.
Adam: There's actually this weird complacency when you compare yourself to others. Like, I mean, I got the dog in me. I wanna win everything and, like, be the absolute best. But, like, if you actually, like, look around, you realize, one, like, I actually think I'm playing on a different game.
There's, like, this, like, ways that it, it's a law of averages of, of this, like, competitiveness. And the desire to win is not the same as the desire to compare, I think. And, like, my motivation to, to beat my coach in every day did not come because someone did that before me.
And if that's, like, how you kind of approach business of, like, "Well, I'm gonna do what this person did before me," I think you're probably gonna end up pretty average and have average results because you're just, like, following another blueprint that exists.
Joe: So we're talking about this desire to constantly get better, winning but not comparing. What now, as a, as an entrepreneur, what are the things that sort of keep you up at night? Like, what is your sort of central preoccupation these days?
Adam: I mean, the number one thing that keeps me up in this time of twenty twenty-six is just, like, pure excitement around what I can do. And we rechanged our entire org structure in April and built a lot of new workflows around AI. And as an idea person, to be able to just... You know, last night it was like, "Man, I really wanna get this one feature done." And I worked till five in the morning, and it wasn't out of, like, this, like, holy shit, I'm screwed mentality. It was like, I can't wait to do it, and I feel like I'm, I'm a kid. And I think that's, like, it's so fun, and I think that's, for twenty twenty-six, I think that's, that's, like, generally the most of the stuff keeping me up is, like...
Also, uh, I mean, the flip side of that is, like, how do you keep up? And I'm, I'm an avid person on X, and I read everything I possibly can, and, like, I use all the tool. I mean, and I still feel like I barely keep up.
And so I think that right now is like, how do you make sure that you're giving yourself every edge possible and every tool possible, but also just, like, get to go do and build the things that you, like, have been needing and wanting for a long time that can help make the business better.
That's by far kind of the, the main things that I'd say I'm staying up for.
Joe: How are you using AI to run the organization differently now from how you might have done it three or four years ago?
Adam: So we were traditional product design engineering. We use an Agile system, everything, check, check, check, check, all the things. In April, we flattened it internally. We built everybody into two teams. We have our machine team and our builders. There's about three to one people on the machine to builders ratio, a little higher, like three point two to one.
The machine team has been building guardrails and workflows, design system, everything that builders... And their, their customer is the builder, so they're not even really... I mean, we have, of course, some folks focused on the architecture of the actual software, but generally what they're doing is building for builders, and our builders are the ones now fully going from design to implementation all the way through QA, and they'll just take a project all the way, all the way done.
And so we have set projects for the quarter, but we have our objectives. And, you know, as a builder, you have to get done our set projects that are kind of strategic initiatives, but also you have the freedom to just go, if you think, "Hey, I wanna move that down mile from here to here, and I think this thing's gonna help us get a little bit higher," we have a system that basically allows you to map that out, design it out, build it out, and then push it to production.
And we've implemented that in April, and it's been compounding every month with the work of the machine team of, like, allowing those things to have less bugs, less risk, following best practices I mean, all the things. And so, but it's really kind of collapsed our team. No, those roles are kind of gone, but it's allowed us to, to move significantly faster and pursue what our instincts are more often than just like, "Oh, here's the, like, six things we're gonna do this quarter."
Joe: And then how are you seeing that structure in the way you're using AI on the team filter down to the community building, content creation, and marketing work that your customers are sort of doing along with, alongside you?
Adam: So I mean, our, uh, I just did our all hands today. Our, like, usage metrics are, like, all-time highs. And if we look at this week a year ago, it was like top ten worst weeks of the year. So we're having big success. I think more importantly, we're like everybody has to have, and I think generally both on the kind of content and community side as well as on the, the ad side, is cycles just used to be so slow that customers and users would just, you know- Not share feedback, and then, uh, if they did share feedback, they never saw it get changed really.
And you see some exceptions of this, like Tobi on CEO of Shopify, who's created a culture around, like, responding to users. But what we really started with was, like, instead of focusing on net new features, like, let's just focus on having users and customers feel like we're, like, not listening to them, but like they wake up the next day and it's done.
And can we, like, create a speeder on that? And what we found is that it was an absolute flywheel of feedback, where the more that you did, the faster you did it, the more they gave, and then the more bought in they were, then the more usage they had. And they felt like they were part of the product and then rewarding them with merch and things like that for just, like, helping and just created this, like, huge cycle. Of course, you always care about your metrics with a feature that you build, but when something takes eight weeks to build it, you're like, "It better fucking work, all right?" But now if, like, someone's just like, "Hey," tonight-- like, last night I was like, "Hey, I just really wanna do this thing. I saw someone submit this for feedback. I wanna build it." It takes a day. By next week, I can see how it's working.
You're actually more metric-forward with the speed than you were when you were more methodical, and I think that also helps, really help you focus on prioritization of, like, what really is gonna move the needle or not.
Joe: Yeah. So the, uh, faster speed of creation and iteration is actually bringing you closer to the customers, which is then creating this sort of like positive feedback loop where you can, like, keep iterating, get feedback quickly, improve on it, or try something else.
Adam: That's not a new theory. I think what's new is that the size of team, the skill sets of team and who can do that has changed. And so I am not technical by any trade and-- but I am really close to our customers. And so now I can, like, leave a meeting and be like, "Man, I'm gonna go, like, do this 'cause I heard it," and, and that- I think that just goes, goes a really far way.
Joe: So for me, this has been the biggest breakthrough of the last few months with AI is that, you know, I run a service business. We have sort of fifteen to twenty clients at any one time.
We've passed the point where I can be on every client call, right? But we have, you know, client call transcripts and, like, you can now use AI as a service, as a CEO to synthesize that, that information and sort of get closer to your clients, right? And really be up on, like, what's going on. And you can sort of take the temperature of every account now in a way that was previously impossible. Like a service business owner even five years ago, they really, they need to have account managers, which of course they still do, but they need to rely on the anecdotal account from that person of, like, what's going on. As we know, as CEOs, right? That's real wishy-washy. Uh, and it's good, it's good when times are good. And when you have a down quarter, you're like, "Oh, what the hell is going on?" And you don't have insight. And now I have evidence as to what's going on on every account.
And it's brought me so much closer to my clients because not only do I know sort of what they're actively concerned about, I can get their own words on and whatever, but it's allowing me to stay in touch with them and sort of send like a customized email or a text and be like, "I know what's going on in your business. I know what's going on in the industry 'cause I'm seeing it across all my clients' businesses, and, like, here's my take." And that, that small sort of thing would have been impossible to do even at the scale of twenty clients, you know, three years ago.
Adam: And the other thing that I have found a good example of that is I really kept asking our sales team, I kept saying like, "Hey, you know, what are the attributes that customers are asking for?" Basically, they're like ICP filtering. So if they wanna reach a health system, are they asking about bed counts, facilities, geography? Like what, what attributes are they asking about? And I, you know, I was-- I'm ready to go build that into the, the product around the dataset and, uh, in general, the sales team is like, "They're not really asking about that. They're not really asking about that." I'm like, "Okay." And so I, I had a hypothesis that they were just in maybe not an obvious way.
Joe: Right.
Adam: So I had to listen to two hundred sales calls, and it identified like fifteen attributes that kept getting brought up. And I think that's the other, like, opportunity here is, like, building for the things that people don't know they need. Our sales team wants to meet the customer's needs. I have no doubt that their intention is that they want to do that. Sometimes it's hard to understand what people want.And I think getting pattern recognition, hearing, seeing something across twelve conversations like one time, it's not that different than if you tell a doctor like, "Hey, I'm tired." And the first time you tell them, they're like, "Oh, you're fine." Second time, "Eh, you're fine." Now, AI catches it. You said that twelve times in a row. Like, they're gonna realize like, "Hey, maybe something's wrong." And I think that's, that's this opportunity also to, like, meet your customers where they're at that, like, never really existed. I mean, you, you only got that from your, like, top, top, top people before, and now you can kinda get that across the company all the time.
Joe: Right. It can, of course, have to do this difficulty for the CEO to understand what the customer really wants. That could be a consequence of sort of deliberate obfuscation on the result of employees, but that's rarely the case. It's generally just that you're not hearing, you're not hearing the client, right? Because you're-- it's going through your filter of like you're looking through whatever you already understand that they want.
And like, I know this, you know, because I realized I do it as a salesperson. And I, I, like, saw it in myself and in my sales calls before I saw it in my account managers and in client calls because I would look at, you know, a sales call transcript through AI, and I would be like, "I put together this presentation based on this sales call." Like, "What do you think?" It would be like, "Uh, dummy, you missed these, like, three things they said that seem really important." I'd be like, "Whoa, so true. I did miss those things." And it's because I had a preconceived notion of what the client's problem was and what they wanted.
And when they told me something different, my brain was naturally like almost ignoring it and, like, slotting it into my preconceived notions of, of what would work. So people generally talk about AI in terms of creation, right? Creating products, creating content, whatever. But this process of sort of like discerning what people want and getting to the truth and getting evidence, it's so valuable Yeah.
Adam: Well, and I mean, this is like what I worked at a Fortune 500 company for a little while. Like that's-- We had product marketers and product researchers. I mean, this is what they would do for a living, and they were really good at it, and it would cost a fortune, and it was slow and, uh, all the things. And now you just... You know, and I think this is like the... And it relates, uh, adtech to sales. Like, I think today, the more integrated you can be within someone's workflow to get those insights than having them do something extra, the better that is gonna be. And that's the... It used to always be like, "Oh, well, can we do, like, a special call? Can we do this thing? Can you fill out this survey?" It's like, can I get all that from one call? Can I get that from the first discovery call?
And all of a sudden, you've not only made your client spend less time with you, which is generally something that they want to do, you're also making sure that that one call is, like, really, really great, and it's easier to train people to do great on one call than train them to be good on five things.
Joe: Yeah, a hundred percent. All right, let's get into some of the B2B marketing stuff. Let's get into our core shtick now, Adam. So – One of the things I see you saying all the time that's very relevant to my business, and I also repeat constantly, is that you don't need to be, like, a ham to be, like, sort of a public face and share your expertise on social and boost sort of your own reputation and that of your company. Like, I've read all your tweets on this, and I totally agree with them.
I'm curious for you to talk more as the, like, owner of this company that sort of depends on B2B creators and on getting, like, normal professionals who know a lot to share, uh, their ideas in public. I'm curious for your experience of why don't people do that, and how have you succeeded at getting them to overcome that aversion?
Adam: There's-- The name I have for it's called the experience paradox, and the more experience you have, the more people wanna know from you, but the less you're likely to share, and that's how we get LinkedIn.
The cause for that, though, I think is, like, quite simple. Uh, it's, it's three things.
It's-- The first one, which I think is, like, kind of the most BS, but it's, it-- if you talk to people, this is what comes up the most, which is time. Uh, which, it, you know, I have two kids under four, I run a company. It's hard. Uh, it's a lot of time. Time is hard to find, uh, the more experience you tend to have, and so is it a real problem?
Yes. Is it why you don't do it? No. But it, it comes up. The second one I think is more, way more valid and something that we talk a lot about, which is, like, the risk-reward. "Hey, I don't wanna tweet something and then hear about it the next day from HR or from my team of being like, 'Wait, you said that thing. Like, wha-what's that mean for us?'" And there's, like, this, like, I already have a hundred headaches. Why would I want to create a possible another one? And the answer to that is the reward.
And I think there's just generally not enough awareness and truthfully reward at times around what can happen when you put yourself out there enough. And it's financial, sure, but it's, it's way more than that. It's, I like to say it's like your career insurance. You are forever unknown now as, like, somebody that has this thing and, like, if that company, like, doesn't work out or if this thing happens or if that, you, like, always have that reputation there.
And I think what I found in these conversations so much, and my favorite type of people to, like, have conversations with, I'm like, "If I would call your, like, two closest coworkers, would they, would they just, like, rave about you?" They would. They think you're amazing. You, like, show up every day, you do a great job. Like, those two people would always recommend you for another job. Why not get, like, two thousand people like that? And the only difference is that you're just not sharing what you know. And that's like conquering this risk-reward basis I think really helps people honestly normally get over the timing too is like, "Hey, wife, spouse, husband, I can now-- This is why I'm doing this. It's gonna take up my Sundays.
I'm gonna do this thing, but it's, like, worth it." And then lastly, and I've-- and you were, like, the only person, no one ever responds to tweets about this, uh, except you, which I very much appreciate. No one wants to admit it, but it's insecurity. And, like, these folks lead businesses, they lead teams, they show up every day incredibly confident in them- their-- themselves.
But, like, I like to-- I used to be-- do some theater, and, like, it would always amaze me to watch people who would, like, be in plays and be in a great role and show up in this huge way, and you meet them, and they were just, like, kind of timid and quiet. And this is because, like, when they were on stage, they, they had this ability to get this confidence. And so many people in business and that are really great have that same thing. Like, when they show up for the presentation, they know how to turn it on and do this. And that confidence, all of a sudden, when you get on social, it just, like, all goes away. And, like, they get in their own head, and that's insecurity of, uh, people don't wanna hear this. They already know this. I'm not-- What I have to say is not important.
And, like, rarely do they wanna admit that, but that's most of the time the problem. And honestly, the solution to that is just telling them that to their face and being like, "I know this is why. It's okay. Let's just, like, do it." And then they normally get over it.
Joe: It's funny because I totally agree that that is the number one reason, is just that people are, they're insecure, and there's a certain vulnerability to sharing your thoughts publicly. You know, people are afraid that someone's gonna be-- they're either gonna disagree with them, and it's going to be a sort of unpleasant disagreement, or people are just gonna be like, "That's boring," or they're gonna get three likes. Like, dude, we publish content on the internet about B2B marketing. A lot of our posts get three likes, you know? And that's just the reality.
Like, you need to-- The, again, it's like what you said about going back to, like, you know, your early experiences in life of, like, failing, um, and being comfortable with that and just being like, "Okay, here's my baseline. How do I get better?" Like, if you produce a lot of content and you get used to, like, exercising the muscle of sharing your, your thoughts publicly, you're gonna flop a lot. You're gonna have a lot of posts that no one cares about. And it's like, it's totally fine because guess what? If no one, like, interacted with it, then either A Actually 10 people did interact with it, and especially in B2B, they may be the right people, right? Which is another thing we both preach is quality over quantity. And B, if truly no one interacted with it, then it just goes into the ether, and it, it's fine.
Adam: So that point, we built an entire kind of slogan, company, the product, everything that we do integrates this philosophy around who, not how many. So, like, any of our ad reporting, any of our content, any of our metrics we show internally, externally to anybody, i- it is, like, absolutely real that, like, there are 200 health systems. If I had the CEOs of all those on my newsletters, you literally have trillions of dollars of budget at your disposal. Why the hell would I care about anyone else?
And, like, also this, like, gamification, clickbait, whatever. L- other ways to, like, get how many, and it actually means no influence at all, and actually, and sometimes negative. And I think the other aspect though, besides even if it gets three likes, and I, I see this more times than I can, I can tell you, is people go back and read that. It's a resume. And, like, when I was fundraising, people bring it up. Like, I wa- I'll never... I walked into a meeting with, like, a really big firm, and he said this line to me, and he was like, "Ah, how about that leaky bucket problem of newsletters?" And I was like, "I wrote that newsletter two years ago." Like, and he knew. He went back and read it, and he, he loved it. He was like, he was like, "Yeah, I, like, couldn't agree more. I hadn't named it yet. Like, I get it." It is, like, you actively building your thoughts and resumes, and guess what? Like, over time, it's okay if it changes. It's okay if it's wrong.
People do dumb stuff when they're 20. People do dumb stuff when they're 30. They say stupid things. It's okay. And, like, I think that's-- You just have to kind of accept that and move on.
Joe: I did this super, uh, you know, human sort of honest post recently about failure 'cause I'd been fired a couple of times in the past, uh, month, and I wanted to, you know, share what I was going through. It's sort of how I think about it as an entrepreneur. And it got, like, you know, 25 reactions on LinkedIn, but, like, 12, like, 15 of them were from, like, CEOs in my industry, right? And it's like, why is it resonating with those people? It's like because CEOs and founders are the people who, like, chew the glass, right? They are the people who, like, constantly fail, and they fail in front of other people and, like, it's painful and, you know, they, they keep going. And so it's like, I don't know. I've been thinking a lot more about this recently, especially with, like, the proliferating AI slop on, like, especially LinkedIn.
Like, I just think there is such a premium, and again, especially in B2B, on these human connections, and, like most of us in B2B, whether we're salespeople, marketers, CEOs, it's like we're trying to reach, like, under 100 people, right? Who are just, like-- And we're just trying to create a human connection with those, like, 20, 50, 100 people.
And if you can do a post that gets three of those hundred people on a given morning to, like, remember you exist and be like, "I F with that guy," then, like, that's really good, you know? And you need to-think in terms of the real impact.
Adam: And, like, the hard part is, like, when you're a, let's call it, like, when you're a finance person, you're not, like, thinking about like, "Wow, Twitter's incentives as a horizontal platform really, uh, don't align to me understanding the who I'm trying to reach," right?
Like, it's like not, it's not-- You're not like pr- You're looking at, like, "Oh, I get three likes, and this meme gets a million." I think in many ways, you know, and this is very much Workweek related, but I think, like, the horizontal platforms don't reward that behavior enough, and it does just naturally after you have to just be, like, ruthless in your own intrinsic motivation and not externally to be like, "I'm just gonna keep posting, I'm gonna keep posting, I'm gonna keep posting." But yeah, I can without a doubt say that every major introduction of any investor I've ever worked with came from Twitter. And I average, like, 12 likes per post, right? So, like-
it's a false signal in so many ways, and, and I think also, like, you have to recognize one of our values at Workweek when we create content is, like, avoid the lowest common denominator, and the, the reason for that is, like, it's so easy to think that smart people don't think you're smart because you have low likes, but that's like such a lowest common denominator thinking.
Like, smart people know-
Joe: I love that.
Adam: Smart people know, like, "Oh shit, that's a smart post." And it doesn't matter how many likes you have, and you just have to, like, avoid that. Right.
Joe: And the who can work in the wrong direction too, right? Like, on LinkedIn in particular, there are a lot of B2B marketers who just create content for other marketers, and there's nothing wrong with that necessarily, but it all depends on what you're trying to achieve, right? If you're like me, right, and you're running like a B2B marketing agency, you actually really wanna be talking to a combination of CEOs of those companies are honestly probably your primary target, and then secondarily, uh, marketing.
Like, if you're the marketer who's doing a lot of content just, like, complaining about, like, CEOs or your clients or, like, something like that, it'll do better quality, right? It'll drive more likes, but it's not actually gonna drive business outcomes. So sometimes the quality actually is in contrast or in tension with the quantity.
Adam: One of the things that we do to help people create content is that we, we make you build out personas of who you're writing for early, and that's natural to marketers to hear that. But, like, if you're, if you're in HR, that's not, like, something you're told, or if you're r- running a hospital, like, it's just not a thing that you know. But it's a big difference. Um, you know, for me, I, I try to do a portion of content for potential creators, a portion of content for B2B advertisers, and a portion of content for, like, entrepreneur investors.
But, like, that has to be very intentional then how you build that out a little bit and think about it, but I think too many people kind of walk in and don't have a strategy around that, and it doesn't need to be, like, wildly a ton of work, but, like, when you don't think about it, all of a sudden you're, you're chasing the wrong things and getting the wrong reward mechanisms.
Joe: So we're preaching to the choir here, talking about quality over quantity and all these other precepts. But when you're not preaching to the choir, when you're preaching to, like, the CFO or something like that, or you're helping your CMO clients, uh, speak to their CFO, what sort of work have you done or metrics have you come up with, or frameworks to help Workweek's advertisers understand the value of these, like, very targeted audiences?
You mentioned, for example, reporting on who, not how many. So tell us more about that.
Adam: So it's our goal to have the most transparent and highest performing B2B ad network, and the transparency part is the hard part there. Uh, performance comes from having great creators and having great audiences that trust you. And I've enabled that to happen, um, which we've spent the last three or four years building out.
But transparency means not falling into the trap of lying, exaggerating, whatever you wanna call it. And so, like, you know, something we've done, like, two things particularly for advertisers. One, we're mostly email and newsletter based, um, and, and really one of the, the only B2B ad networks on that is more native newsletter. And one of the issues that I've learned through the years of working at The Hustle and all these newsletter companies is that open rates have just continued to be a lie. That like- the non-human interactions basically have continued to go up as security scanners have gone up, particularly in B2B.
And the problem is, is none of the email platforms, you name them, they all do the same thing. None of them wanna admit that it's all fake because then their competitors blame them for bad deliverability. And so if they lower their open rates to be honest, their competitor says, "Look, see? Your open rates are worse. They're-- Come here." And so it's allowed all of a sudden, like ten years ago, a really, really good, unique open rate was like twenty-seven, twenty-eight percent and now like it's fifty.
And I'm like, this is-- Like, sorry, it's not happening. And so what we did, we made our own model. We open sourced it on GitHub, and we really filtered out all the, the next level of security scanners and interactions and, and obvious things like, hey, this person did not click ten links in four seconds. Like, that just didn't happen. And it lowered our open rates by half. Mm-hmm. And I could look at all my advertising and be like, "I'm telling the truth." So this is who actually opened it. And then clicks is even more. It's like ninety-eight percent of all clicks in emails now are not human interactions. And I was like, now we're doing with clicks. But what you can trust is that unit is correct. And what we've done is through building our identity graph, we're able to take that engagement and put it into their CRM. And the reason why no other email ad network can do that is because those metrics are a lie for them.
So then they'd be putting their very not correct metrics into a CRM that a salesperson would believe is true, and then that person's gonna call them and be like, "Did you just engage with this ad?" And the person will be like, "I have no effing clue what you're talking about." And it's a bad look for everybody. And so I think it's a first principle thinking of like telling the truth and- Yeah ... what it enables downstream, but you had to have the hard conversation and be like, "Guess what? No one's telling the truth here." And that who though carries if you can meet someone in their CRM of where it is and it's a match.
Now, do you really care what the CTR is if you had ten of your top hundred customers engage with that ad? I don't think so. And so that's-- It's kind of flipping- the whole model on its head is what we've done.
Joe: We've kinda come full circle because again, it's like about that failure and that honesty, right?
Like you're essentially-- You're saying to the Workweek advertisers what your tutor said to you about Spanish class, right? You're like, "Look, we don't have a fifty percent open rate. We're not driving ten clicks in four seconds. Here's where we're at," right? Like, "Here's whom you're actually able to reach." If you think about it for two seconds, actually that is immensely valuable. And so let's work with that honest baseline and do better.
I think what you've arrived at is sort of this really differentiated position within B2B advertising, which is like, uh, telling the truth, and that's a pretty cool business model.
Adam: It's what we try to do. Every salesperson I hire, we've, we've been able to kind of bring on some amazing sales leaders from all across the kind of B2B ad sales landscape. And I write a weekly newsletter, and last week, uh, we have Upfronts, which is an event in a couple of weeks, and we bring in all of our customers to Austin and, and have a good time and, and talk about our big launches coming up.
And I emailed out-- I do a weekly newsletter internally, and I emailed out and I said, "Hey, you know, the theme of this year is like transparency and honesty and like why it matters, and tell me something in your past career where everyone knew it was a lie, but no one said it out loud, but like, you knew it." And I mean, everyone who ever thought it was at the B2B ad sales team, they're like, "Everywhere I worked, it was a lead gen program that we just bought the leads and sold them from somewhere else." So like, it was just-
Joe: Yeah.
Adam: I've been in that game, and it doesn't last, and the, the clock will hit sooner or later. And more importantly, I think we have the creators and the content that actually perform. And if you can prove performance, you can pay-- get more money. If you can get more money, you can pay-- make people have a better reward to risk system and, and hopefully get more people to create content. So that's kinda what we're focused on.
Joe: Yeah, a hundred percent. And generally, the problem is when people hear prove performance, right, they rush to all the normal BS tactics, and you're taking a different path to that, and it's, uh, very cool to see. So Adam, thank you so much for doing this. Great to talk with you, and, uh, yeah, good luck with everything you're doing, and we can keep liking each other's posts so we can get past, uh, three likes one day.
Adam: You got a friend in me, my friend. It's, uh, it's all good. And, uh, it's okay. I'll take three if it continues to give me good podcasts with the right people. So thanks, Joe, for having me on, and, uh, and I can't wait to listen to the next one.
Joe: Thank you very much.
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