You never know where someone’s career will take them, and Jay Schwedelson is totally fascinated by Adam Ryan’s unconventional path—from ninth-grade American government teacher to building the B2B creator community platform Workweek. Adam breaks down why the future of content and community isn’t about brands, but about real, trusted personalities—and why “community” might be the most overused word in marketing right now.
Check out everything Adam and his team are building at Workweek, and explore their creator-led communities and content: https://workweek.com/
Best Moments:
(01:45) Lesson plans at 6:30 AM and why Adam left teaching for good
(02:33) Your career isn’t linear—scroll Adam’s LinkedIn if you need proof
(04:45) People crave learning from individuals, not faceless brands
(07:45) When you need trust, a real human should lead your newsletter—even if it’s ghostwritten
(11:13) Why most brand “communities” flop and how Workweek thinks differently
(14:06) Engagement loops are the secret sauce to keeping communities alive
(17:01) The TikTok lesson: relevance is everything for ongoing community value
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Transcript
Jay Schwedelson: What up? Welcome to do this, not that, the podcast for marketers. I'm Jay Schwedelson. Let's dig into some tips and some randomness. We are back for Do This, Not That podcast presented by Marigold, and I got one of the smartest dudes that we've ever had on the show. Alright? So if you asked me, alright, you could pick the brain of one person about where it's all headed. You know, content marketing, creator marketing, events, all this stuff. Who would I say? I would say Adam Ryan. That's who I would pick. So Adam Ryan is the co founder and CEO of Workweek, which is this amazing, B2B creator events community platform that has just been exploding the last few years. But before that, the guy was the president of the hustle, which is very cool. It gets acquired by HubSpot. Before that, Heaty wasn't just working at Procter and Gamble and Red Bull and Under Armour and every other amazing company. The dude was a ninth grade American history teacher. That's when I peaked in my intelligence. It all went downhill from there. This guy has done it all, and I cannot wait to dig into all sorts of stuff. So, Adam, welcome to the show, man.
Adam Ryan: Oh, Jay, I live for your intros, man. They're always the best, and, I'm so happy to be here.
Jay Schwedelson: I wanna ask something. Before we get into everything and we're getting into all, ninth grade American history teacher, do I have that right?
Adam Ryan: American government. Yeah.
Jay Schwedelson: American government. Yeah. So, like, did you your first days when you were first teaching that class, did you have massive, like, impostor syndrome? Or were you like George Washington? You knew everything about American government. You just crushed it out of the gate.
Adam Ryan: No. I didn't know it at all. I mean, like, no one does. There's too much. And also, graders ask every question you can't prepare for. So, it was, it was quite the the learning experience, the learning how to think on your feet. And, I notoriously made most of my lesson plans at about 06 But yeah, it was a I taught ninth grade and got my master's in education and I I still consider myself a teacher, but, just not so much in the textbooks anymore.
Jay Schwedelson: Listen. Everybody out there is listening to this. Your career is not linear. Go to Adam's LinkedIn page here. Okay? And just scroll down to the beginning. It's not like he knew exactly where he was going to wind up. He was going be the president of the hustle and founding these companies. You will do different things. So don't feel if you're not on course right now that you're not going to get to exactly where you want to be ultimately because Adam is proof of all of that. So before we get into all this stuff I want to ask you about, Workweek. I I hyped it up. I love Workweek. What does Workweek actually do?
Adam Ryan: Sure. So we are platform for professional networks. So think about LinkedIn, but if it was only for people in HR or only for people who were in ecommerce marketing. And then what we've done is we've partnered with creators or really their practitioners in these spaces. Because if I went to go start an HR professional network or community, I'd have zero credibility to do so, and I probably would fail within a couple days. And so what we realized to be able to go kind of this multi vertical approach of of the building these communities out, we need to build up an audience. We need to build trust. We need to build credibility, and there's no better way to do that than partnering with experts in those industries and giving them a platform for newsletters and podcasts and then growing those audience from there and then then launching the network. So we have our own kind of in house built platform. It feels very much like a social network for your own industry. You have to apply and be verified, and then we monetize primarily with advertising and with a little bit of subscription.
Jay Schwedelson: So I follow all the stuff. I consume all the content you all put out there. And what it feels like to me is that you all are bullish on personality led brands basically. Right? So email newsletters are a core component of what Workweek does. And what I'm curious about, why are you bullish on email newsletters when it feels like there's a zillion newsletters out there? And should brands have a personality driven newsletter? Is that where things are headed in this world of AI garbage?
Adam Ryan: So in in:Jay Schwedelson: Yeah. In a lot of ways, I think personality driven newsletters by experts is really the origin of kind of influencer marketing in a lot of ways. You know, we send out the stuff and in the newsletter, check out this article, you know, I'll read Daniel Murray's newsletter or whoever said, check out this article. There's a great SaaS product. There'll be an ad in there. And that's what I want to consume. But flipping the script a little bit, let's say that you're just a brand out there, you're a brand marketer and your brand has a newsletter that is not doing particularly great. It's like wallpaper. Are you advocating for brands to find a personality within their organization and start to have their newsletters come from a human? Is that is that a strong go to market in your opinion?
Adam Ryan: Taking a step back, I'd I'd ask that person, what are you trying to achieve with that newsletter? Are you just checking a box? Are you trying to educate your customers? Are you trying to use it to create leads? And each of those has different meanings and purposes. And so if it's, hey. We just wanna give everyone our updates of our feature launches, that probably can come from a brand. When you need to educate someone, something that re or or try to sell someone, something that at the core, you actually need trust, you have to find a person to lead that. And that's really what we're saying is if you're just informing somebody on something, I think the brand relationship is okay. If you're trying to influence someone, that requires trust. And I if I was a brand, I'd be looking at, like, hey. Who's our technical product manager that we can talk to about this? Or who's can we use one of our executives? And I think the the key secret sauce here of the tactic is, like, that person doesn't need to write that. It can be ghostwritten. We did this at the hustle for literally all everything we ever did, and it's okay. Obviously, that person should should feel confident about it. The team should represent their values and who they are as as humans. But as a brand, it's okay to scale a personality in the same way that you scale a brand. And that's something that I would lean into more.
Jay Schwedelson: You know, it's actually a great tip to have let's say you have a a SaaS product or whatever, to have a newsletter that's coming from an engineer or whatever. It doesn't need to be your CEO or whatever. Again, can be ghostwritten the latest whatever in your product or how it influences, impacts, whatever's going on. I think it's a great idea that so many companies out there can do. And again, you'll be able to influence future, you know, buying habits of your prospects, existing customers, of it.
Adam Ryan: Well, and what's interesting is like, if you look at if you talk to a B2B marketer at an enterprise SaaS solution and you say, hey, what's your go to market strategy? And they're like, well, you know, we fill the pipeline up with s d MQLs, SQLs, then our sales team sends them cold emails and sets meetings up. So your sales team is acting as the trusted expert to educate that marketer or that buyer to get them on the phone. You can do that, and that's what they already are doing this strategy. They just are used to it with salespeople, and it's more tactics and, kind of volume. But if you flip the script and say, hey. This isn't actually anything new, but instead of our salesperson doing it, we're gonna have our engineer or our product manager do it. Now you're coming from a whole different value prop, in the in the sales cycle.
Jay Schwedelson: Oh my god. I totally agree with that. It's like putting too much on sales to be responsible for knowing everything. Alright. So let me take a I want to turn into a different direction. I want to talk about communities. Literally when I say the word community, every time I say it, it's like sort of nails on the chalkboard for me because I'm all about community, but by the same token, I think everyone does it. Oh, we have a Slack channel. That's our community, which is horse crap, turns into a ghost town. And yet you all are doing communities where people are actually showing up, they're engaging, they're doing stuff. So talk to me about what is like the right way to do community?
Adam Ryan: Man, that it's a big question. I I think the reason why community has that same it's a natural resentment hesitation, I think, when people hear that word is because community means a lot of different things in the same way content does. And I think if you said, hey, how do you do content? We could sit here and talk about top of funnel, bottom of the funnel, newsletters, podcasts. There's that that that word is very big. And I think community should be thought about in the same way. And you can have your community for retention. You can have community for prospects. You know, there's a you can have community in person, digital, but all those things mean that that they're set up differently. And I think at the core, what community should be is about helping people connect, learn, grow. And that is what I believe at the core of what every person wants in their profession is, can you help me meet people that are interesting? Can you help me learn things that I don't know? And can you help me grow in my career? And that is if you're doing any business aligned community, whether it's in person events or digital or whatever, that's what it should be focused around. And to the point around Slack and these other tools is I think people forget about that moment. They're like, hey. What did you you just set it up. Cool. You're there. You got a hundred people there. Great. What moment are you trying to create? And I find it so interesting. We do so many events and have been part of events businesses for a long time. And in events businesses, you really great events, think about, like, literally how you walk through the door. Like, hey. Where do you want your eyes to look? What do you want what do you want the sound to be? What music are we playing? Because that's how you experience this moment. And it's really interesting when it goes to digital communities. Like, it should be treated the exact same way, and no one really thinks about it that way. And so that's where we saw the opportunity very much as I believe people today are craving the opportunity to connect, learn, grow with other people in their field, but they want it to be done in this way that's experiential and efficient and ultimately help them help them do what they wanna do. And so we built our own platform for that because we didn't couldn't find one that helped us do that in the way that we wanted. But I think that's really why there's this, like, push pull of community and kind of the mistake that I think a lot of people have had of in the same way newsletters were maybe eight years ago where people just sent one to check the box. I think community is in a little bit of a moment where people are just checking a box.
Jay Schwedelson: So by the way, I'm a member of your marketing link community and it's awesome. And I'm not just saying that because I'm staring at you. It is genuinely awesome. But I want to ask you a self serving question that everyone's going to be like, why is he asking this? This is like meaningless to everybody else. But I want to know for myself. So we put on this big conference. We put on a bunch of conferences, but one of them is our email event called Guru Conference. So this past year we had 24,000 people. And then coming out of it, everyone's like, we need to stay connected. What's the community? Whatever. And I'm like, oh God. So we stood up a WhatsApp community. Okay. And we said, everybody, here's the WhatsApp, wherever you join this community. And we said it was going to be a pop up community. And we were going to have it last for thirty days because I was convinced it would die. And so we stood it up and for the first two weeks coming out of the event, everyone's in there. This is awesome. We're talking about careers, crap, whatever. And then by like the third or fourth week, it was just dying. Like nobody's posting. There was four people from like, I don't know where they live posting over and over again. Everyone else disappeared. So my question to you is, in order to have a community that stays active and alive since you have a bunch of these communities, do you kinda have to, like, juice it? Do you need to have, like, your people in there getting conversation going? How the hell do you not let it fall apart like mine did?
Adam Ryan: Yeah. I it's a it's a great question. I think it's actually why at the end, there's one publicly traded business. This is a little bit of a a step back, but there's there's one publicly traded business that does a business community. It's called Doximity. It's a it's a community for physicians. They're worth 10,000,000,000 today. No one knows them unless you know a doctor or a physician, which then they definitely know it. But, you know, their niche, it's special, but, like, their team is built to treat their community like a social network. And I think it's actually a really this is why I'm not as excited about the Slacks and the WhatsApps of the world because in order to actually drive engagement and retention of users, you have to think about engagement loops. You have to put your marketing hat on of, like, how do I drive this behavior back? How do I actually repeat this? And and it's I used to say this all the time in the newsletter world, like, you build it, they will not come. And there was this belief, like, if I have the very best content in my newsletter, one day they'll come. It's like, that's not true. You have to, like, get it out there. You have to, like, post on social. And even if you get two likes or two email subscribers, like, that is the start. Like, that's what you have to do. And but, like, just focusing only on content and not on audience won't get you there. And with communities, it's the same way. It's not just getting people in. It's you have to think about how do I keep them engaged through these loops. And that's you know, when you look at successful communities, and we don't like to think about LinkedIn or Facebook as communities, but they really are in the way that they should be thought about. They constantly have ways to bring you back to the platform and re reignite you, and a lot of these out of the box solutions just don't have that in the way that's required to scale and and retain your user base.
Jay Schwedelson: Dude, I love that idea of engagement loops. Everyone just talked about feedback loops, almost like negative feedback loops, but engagement loops, it's so, it's so true. You talk about doctors, my wife's a dermatologist and she loves the Facebook group for dermatologists. It's like the greatest thing of all time. She's in there all time. I'm like, I can never believe it. Like you're on a Facebook group? Like really? Right? I mean, it it can be hard.
Adam Ryan: My wife is a moderator of a nonprofit Facebook group with, hundred thousand people, and it is run like a business. But they also like, Facebook has built the natural tools to have the engagement loops there. And so that's, you know, and that's the advantage of using a tool like that. And but I think that's the piece. And and the other one is relevance, would say. Like and I've I've I've experienced this myself. I'm in a lot of Slack groups. And we all know it if we're being honest. Like, hey. Sometimes there's a killer question in there or insight. I'm like, man, I love that. And I think Workweek is is trying to get a lot better at this with our own communities. But, you know, there's something that to say, like, let's learn what TikTok did really well, which is, hey. Everything you see is based off of your current interest today. And I think there's there's a lesson there of how do you also not just bring people back through engagement loops, but then also ensure that what they're experiencing is relevant to them in the moment. And that, that's a big that's a big lift. But I think that's actually the the bar that we wanna set with communities.
Jay Schwedelson: Dude, I love all of that. Listen. Alright. Everybody, go to Workweek.com. You're gonna find everything that Adam's up to, all the different creators, everybody that's on there. It is pretty wild. I'm gonna force Adam to come back on, and we're gonna do a trivia contest on American government facts. And we're gonna see what the hell this guy actually knows because I have a feeling we could stump him. I don't know. I feel like he hasn't brushed up on this in a while.
Adam Ryan: So It's been a little while. I am certified in the state of Missouri still. I also learned the president's in order when I was in kindergarten. I've been an American government fan for a long time, so I take on the challenge of the Wow. Of the of the trivia.
Jay Schwedelson: Oh, we're gonna do it. This is gonna be amazing. And we're gonna put everything in the show notes. I'm telling everybody, go check out everything going on work weekend. Adam, thanks for being here, man.
Adam Ryan: Thanks so much for having me, Jay. Look forward to the next time.
Jay Schwedelson: Alright. You did it. You made it to the end. Nice. But the party's not over. Subscribe to make sure you get the latest episode each week for more actionable tips and a little chaos from today's top marketer. And hook us up with a five star review if this wasn't the worst podcast of all time. Lastly, if you want access to the best virtual marketing events that are also 100 free, visit guruevents.com so you could hear from the world's top marketers like Damon John, Martha Stewart, and me.Guruevents.com. Check it out.