People Trust People: The Future of Brand Trust w/WORKWEEK: Co-Founder & CEO Adam Ryan | Ep. 355

13 Jun 2025 · 19 min

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Podcast Summary: Do This, NOT That: Marketing Tips with Jay Schwedelson

Episode Title: People Trust People: The Future of Brand Trust w/WORKWEEK Co-Founder & CEO Adam Ryan | Ep. 355

Podcast Overview "Do This, NOT That!" is a podcast hosted by Jay Schwedelson that provides marketing insights, actionable strategies, and innovative tactics for marketers. This episode features Adam Ryan, co-founder and CEO of Workweek, discussing the evolution of brand trust and the significance of personality-driven marketing.

Key Highlights

Introduction

  • Jay introduces Adam Ryan and his unconventional career path from a teacher to a successful entrepreneur.
  • Ryan’s background includes roles at Procter & Gamble, Red Bull, The Hustle, and now at Workweek.

Career Insights

  • Non-linear Careers:
  • Adam emphasizes that career paths are rarely straight; adaptability is crucial.
  • Reflects on his teaching experience as foundational but not his ultimate calling.

Community and Brand Trust

  • Shift from Brands to People:
  • Ryan argues that trust in marketing is moving toward individual personalities rather than faceless brands.
  • People prefer to learn from real individuals who they can relate to.

The Role of Newsletters

  • Personality-Driven Newsletters:
  • In the age of AI and automation, personal touch in newsletters is essential.
  • Newsletters should be led by people who can create authentic connections with readers, even if ghostwritten.

Challenges with Brand Communities

  • Flawed Community Models:
  • Many brand communities fail because they lack genuine engagement and purpose.
  • People often confuse mere membership (like Slack channels) with real community-building.

Creating Effective Communities

  • Engagement Loops:
  • Successful communities need to implement engagement loops that encourage regular interaction.
  • Communities should facilitate connection and growth among members, not just serve as a platform for announcements.

Relevance and User Experience

  • Importance of Relevance:
  • Just like TikTok’s algorithm, successful communities need to tailor content to users' interests to keep them engaged.
  • The experience should feel personal and relevant to individual members.

Key Takeaways

  • Trust Building: The future of marketing relies on individual trust rather than brand authority.
  • Community Definition: True communities should foster connection, learning, and growth, rather than merely serve as passive platforms.
  • Engagement Strategies: Companies should focus on consistent engagement strategies to keep community members active and involved.
  • Personality in Marketing: Brands should consider leveraging real individuals within their organization to communicate and educate, enhancing credibility and connection.

Conclusion In this episode, Adam Ryan provides valuable insights into the future of brand trust and the importance of building genuine communities around individual personalities rather than brands. Through actionable strategies like engagement loops and relevance, marketers can enhance their approach to community building and content distribution.

Additional Resources

  • Workweek: [Workweek Website](https://workweek.com)
  • Jay Schwedelson's Socials:
  • [YouTube Channel](https://www.youtube.com/@schwedelson)
  • [TikTok Profile](https://www.tiktok.com/@schwedelson)
  • [Instagram Profile](https://www.instagram.com/jayschwedelson/)

Subscribe for More

  • To stay updated with actionable tips from top marketers, subscribe to "Do This, NOT That!" and leave a five-star review if you enjoyed the episode.

Note This summary encapsulates key discussions and insights from the episode while maintaining a logical structure for easy navigation and understanding.

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Transcript

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0:01What up? Welcome to Do This Not That, the podcast for marketers. I'm Jay Schwetelson. 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. All right, so if you asked me, all right, 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.

0:46But before that, the guy was the president of The Hustle, which is very cool, gets acquired by HubSpot. Before that, he wasn't just working at Procter & 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. Oh, Jay, I live for your intros, man. They're always the best, and I'm so happy to be here. I want to ask, before we get into everything, and we're getting into all, ninth grade American history teacher, do I have that right?

1:23American government, yeah. American government. So, like, your first days, when you were first teaching that class, Did you have massive like imposter syndrome or were you like George Washington? You knew everything about American government. You just crushed it out of the gate. No, I didn't know it at all. I mean, like no one does. There's too much. And also ninth graders ask every question you can't prepare for. So it was it was quite the learning experience, the learning how to think on your feet. And I notoriously made most of my lesson plans at about 630 the morning of. So, which is why I very much quickly chose not to follow that career full time to not disadvantage my students.

2:06But, yeah, it was I taught ninth grade and got my master's in education. And I still consider myself a teacher, but just not so much in the textbooks anymore. Listen, everybody out there is listening to this. Your career is not linear. Go to Adam's LinkedIn page here, OK, and just scroll down to the beginning. It's not like he knew exactly where he was going to wind up. He was going to 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 that.

2:39So before we get into all the stuff I want to ask you about, Workweek. I hyped it up. I love Workweek. What does Workweek actually do? Sure. So we are a platform for professional networks. So think about LinkedIn, but if it was only for people in HR or only for people who were in e-commerce 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 of days. And so what we realized to be able to go kind of this multi vertical approach of building these communities out, we need to build up an audience, we need to build trust, we need to build credibility.

3:30And 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. 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.

4:08Right. So email newsletters are 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? So in 2021, when my co-founder and I were starting the business, we wrote an 18-page memo of what we wanted Workweek to become. And a lot is wrong on that. A lot is right on that. But the thing that we said we had to get right for 10 plus years as a trend was that people are learning from other individuals more than faceless institutions.

4:48And so if you think about that, it's the easy example is like, hey, do I trust Business Insider or I trust the writer actually writing it? And we thought that trend was going towards more of this individual approach. And then in business, though, I did hundreds of conversations like, hey, who do you learn from? How do you like how do you feel like you can get better at the job you have today? And every person I was like, what's the most valuable conversation or insights that you got? Almost every person said a coffee meeting. Oh, I had like coffee with this person and they told me this insight and it was such a good nugget.

5:23And what we realized was there was this gap. We called it this knowledge expert paradox where the people that were actual experts in these fields that everyone wanted to learn from didn't actually have the time, motivation financially or otherwise, because they're, you know, a little bit mature in their life, they might have a family, they have other commitments, they probably make pretty good money already, you know, wasting your Sundays for a little bit of cash isn't the best way. But also what you can do with that is start to help so many people access these experts. And so that's been really what we've leaned into from day one is how do we allow individuals who are who really know these fields so well, be at the forefront to democratize a little bit of that knowledge and insights that they've gained through their career.

6:11And when thinking about then, how do you distribute that knowledge and insights? There's no better way to do that than to be able to show off your personality, to be able to do it directly to your listener. And newsletters are just a huge part of that. And it allows them to kind of build this consistency, these habits, but hopefully make you feel like you have a friend in your inbox. Yeah. In a lot of ways, I think personality driven newsletters by experts is really the origin of kind of influence for marketing. In a lot of ways, you know, the, we send out this up, this and in the newsletter, check out this article, you know, I'll read Daniel Murray's newsletter or whoever said, check out this article.

6:51There's a great SAS 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 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 taking a step back i i asked that person what are you trying to achieve with that newsletter are you just checking a box are you trying to educate your customers?

7:28Are 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 want to give everyone our updates of our feature launches, that probably can come from a brand. When you need to educate someone, something that, 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 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?

8:07Or can we use one of our executives? And I think 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 everything we ever did. and it's okay. Obviously, that person should feel confident about it. The team should represent their values and who they are 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. You know, it's actually a great tip to have, let's say you have a SaaS product or whatever, to have a newsletter that's coming from an engineer or whatever.

8:47It doesn't need to be your CEO or whatever. And again, it goes written about 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, you know, companies out there can do. And again, you'll be able to influence future, you know, buying habits of your prospects, existing customers, all of it. Well, and what's interesting is like, if you look at if you talk to a B2B marketer at a 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 MQLs, SQLs, And then our sales team sends them cold emails and sets meetings up.

9:20So 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 going to have our engineer, our product manager do it. now you're coming from a whole different value prop in the sales cycle. Oh my God. I totally agree with that. It's like putting too much on sales to be responsible for knowing everything.

9:57All right. 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? Man, it's a big question.

10:31I 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.

11:10But all those things mean that they're set up differently. And I think at the core, what community should be is about helping people connect, learn and 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 aha moment.

11:43They'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 I've 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 aha moment. And it's really interesting when it goes to digital communities, like it should be traded the exact same way.

12:16And 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 do what they want to do. And so we built our own platform for that because we 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 push-pull of community and kind of the mistake that I think a lot of people have had in the same way newsletters were maybe eight years ago where people just sent one to check the box.

12:52I think community is in a little bit of a moment where people are just checking a box. 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 with the community, whatever.

13:24And I'm like, oh, God. So we stood up a WhatsApp community. okay and we said everybody here's the whatsapp whatever you join this community and we said it was going to be a pop-up community and we're only going to have it last for 30 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 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 kind of have to like juice it?

14:06Do 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? Yeah, 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 step back, but there's one publicly traded business that does a business community. It's called Doximity. It's a community for physicians. They're worth 10 billion today. No one knows them unless you know a doctor or physician, which then they definitely know it. But their niche, it's special, but their team is built to treat their community like a social network.

14:50And 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, um, and it's, I used to say this all the time in the newsletter world, like if you build it, they will not come. Um, 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.

15:21You 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. Um, 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, uh, 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 reignite you.

15:58And a lot of these out of the box solutions just don't have that in the way that's required to scale and retain your user base. Dude, I love that idea of engagement loops. Everyone just talks about feedback loops, almost like negative feedback loops, but engagement loops. 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. And she's in there all the time. I'm like, I can never believe when you're on a Facebook group, like really? Right. I mean, it can work. My wife is the moderator of a nonprofit Facebook group with like a 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.

16:37And so that's, you know, and that's the advantage of using a tool like that. Um, and, but I think that's the piece. Um, and, and the other one is relevance, I would say like, and 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 trying to get a lot better at this with our own communities. But, you know, there's something 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.

17:12And I think 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's a big lift. But I think that's actually the bar that we want to set with communities. Dude, I love all of that. Listen, all right, everybody, go to workweek.com. You're going to find everything that Adam's up to, all the different creators, everybody that's on there. It is pretty wild. I'm going to force Abner to come back on and we're going to do a trivia contest on American government facts and we're going to see what the hell this guy actually knows because I have a feeling we could stump him I don't know I feel like hasn't brushed up on this in a while it's been a little while I am certified in the state of Missouri still uh 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 trivia oh we're gonna do it this is gonna be amazing and we're gonna put everything in the show notes.

18:11I'm telling everybody, go check out everything going on at Workweek and Adam, thanks for being here, man. Thanks so much for having me, Jay. Look forward to the next time. All right. 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 marketers. 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 can hear from the world's top marketers like Damon John, Martha Stewart, and me.

18:50Guruevents.com. Check it out.

From the publisher

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

Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

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