I could look people in the eye and be like, "I promise I will make you a very successful business person." Yes. It's just incredibly difficult to create quality in-depth content while running a business.
I think you can't claim being a creator unless you are committed to a cadence. Consistency does win.
You can have an off month or two, a hard season of life, but you just keep showing up and no one else does, you still win. That's a really good answer. Quality will always win. I, like, deeply believe that.
Learn how to say no. No to advertisers, no to clients. No, no, no, no, no, no, no. All the mistakes you'll end up making are the moments that you should have said no. Well, welcome back to the Creator Spotlight podcast.
Today, we are speaking with Adam Ryan, who is probably one of the best business minds in newsletter world.
Uh, he made his name in the space really at The Hustle, which he joined as the first salesperson, driving the monetization strategy, and then he left four years later as president.
Uh, he's also been an advisor to a number of other successful newsletter-first businesses, like 6am City and Every.
But chiefly right now, and this is why we're talking to him, he is the CEO and co-founder of Workweek, a newsletter-led platform for professional networks.
Uh, which we've also, longtime listeners will know, we've had a couple former Workweekers on the pod before, Tommy Clark and Jared Dashefsky. Adam, thank you for coming on. Thanks for having me.
Uh, longtime fan, so, uh, thanks for... And many, many, many mutuals in the space- Yes... so appreciate, appreciate inviting me and coming on.
I guess for the listeners quick we should say, so, like, basically there's, Workweek is kind of a studio. We'll get into more, like, the other businesses later. Um, but in that, like, you guys do create these businesses.
It's, it's a distribution-first product studio or, like, brand studio, I would say, to an extent. Uh, yeah, yeah. So the way that we kind of... And I think this is, like, an evolution of the business. Yeah.
We're only three years... We turned three last week, so, uh, we've had lots of descriptions of us. Um- Happy birthday. Thank you.
Um, uh, you know, there was a time period where we were thinking about, hey, um, similar to, like, what Night was doing with MrBeast, like- Yeah... how can we build products? Um,
I think that's just, like, not a sustainable business. Um, um, I think there, we've had a lot of lessons and learnings but, um, you know, for us, going content to SaaS is possible. Yeah.
We still have a really great vertical franchise SaaS business. It's kind of crazy. Um, but the, the thing that gets forgotten in a lot of those models and that we realized is, like, there's competition everywhere. Yeah.
And so if we're dividing our attention up, someone else isn't. Wi-Fi on 10 fronts. Yeah. And so- Mm-hmm...
um, you know, what we've really focused on and, and started to hone in on is how do we, what we call, kind of build these, like, professional networks which, you know- Mm.... memberships. Um- Mm-hmm...
and a pa- piece of those memberships is this community front. And it's way more natural for all of our content creators that have a huge relationship in their industries and their professions- Yeah...
to have these professional memberships and, um, that's really where, uh, a lot of our, our effort's been headed.
And, um, you know, for the talent, the, the big piece of that Workweek is solving, um, is the ability to focus on what they know how to do. Yeah. Um, and so I,
you know, really try not to ask people to basically do anything that they don't, that I don't believe that they're best at. Yeah. Because they're best at, at something else.
Um, and I think, you know, putting people in positions they're born to do is what we wrote down originally and- Mm-hmm...
um, and then making sure that they're compensated fairly for that is the other, other, other end- Yeah... other side.
Well, I mean, I feel like the, this is true of any creative industry, but, like, I think with the, with the creator economy, with, with creators, it's like you're either really good at the creative aspect and, like, you know, the, the production, the writing, the filming, whatever, being, being on camera, uh, or you're really good at, like, the business, the structure, the ad sales, whatever.
Most people arely- are generally, I think, only good at, like, kind of one side or the other. Some people are really good at both or know to hire for both. Yeah. I, I don't even think about it as good, 'cause I think...
You know, we work in the B2B space. Yeah. All of our creators are so good at business as well, right? But, like- Um-... doing, like, they don't have the time maybe, right, to do both.
I kind of talk about it as energy giving or energy taking. Mm. Um, and so what, what takes their energy is like, hey, I don't want to send 10 cold emails. [laughs] I could. I know how to. Yeah. I've done that before.
I don't want to do that. Um, and, you know, part of, like, putting people in positions they're born to do is not just from a skill set but from a desire. Yeah. Mm-hmm. Um, and that's really, like, why, you know, um,
uh, we really hone in on that early is like, hey, if someone, like, wants to go sell ads and they believe that's where, like, what they love to do, we're probably not a good fit for them- Yeah...
'cause, like, it's a, um, you know, we have 20 people focusing on that. Um, so, uh, that's the... There's, there's a lot of this energy giving and energy taking conversation.
Uh, how big, like, how big, you don't have to say exact numbers, but, like, the average creator, is there, like, a subscriber count that, or like... I don't know.
I, I know, like, it's, it's, right, it's not about how many subscribers, it's about who they are, et cetera, which is really the focus for you guys because it is B2B.
But, um, is there kind of, like, a sweet spot range or something like that? So I think about it, um, in, in two, two terms. Is, is one, what's the total addressable market of our, like, core audience we're going after?
Um, so, you know, on our healthcare side, uh, Blake is, I think, like, the best analyst in the country for the niche that he covers. Yeah. It's basically for healthcare system strategists.
Um, and maybe there's 25,000 of those people in the United States. Yeah. Highly specific. [laughs] Um, very highly specific group of people. Um, you know, HR with kind of directors and up of who we're going after.
Mm-hmm. Startups, scale-ups, maybe company size 25 to 1,000. Maybe there's 110,000 of those people. Mm-hmm.
So what I track, what I, what I care about and kind of, like, have conversations about is like how are we tracking towards capturing that audience specifically, and that's, you know, our data team isIt's almost as big as our creator team, um- Yeah...
and w- to make sure we can answer those questions. And then the second one is, we map that out, how much money do we think we can make, um, and on each brand, and where are we at towards that progress? Mm-hmm.
Um, how are you growing the audiences for each of them? If some of them have come in not really having made content before, is it, is it, like, paid advertising? What are the main levers you're pulling? Yeah.
Um, paid advertising, uh, we're pretty active on social. We support them on social. Mm-hmm. Um, um, and paid advertising. You know, first six to nine months it's very heavy paid advertising.
Once we feel like we have, like, a content market fit and that ICP nailed down, like, you know, uh, we would do things differently. Of course, you learn for, you learn at a, a, something new for each launch.
But- Mm-hmm...
in an ideal process, we, we kind of i- identify the area that we wanna go after, then we identify the talent we go after, how many, how many, and then how many of those people exist, and then, you know, start to put it in.
And I think there's a lot of negative connotation around paid advertising to grow newsletters, and I think it's because people skip the content market fit piece- Yeah...
and they skip of the who they're going after piece. Mm. And so we, we try to make sure to check both of those boxes. And I think, you know, Morning Brew and The Hustle, they can put out...
Morning Brew can say whatever they want, but I'm pretty sure if I had to guess, 90-plus percent of their subs were from paid ads. Um, so- Yeah... um, I think- Well, it's such a classic ad format now.
Like, "Five minutes a day, learn everything you need to know about business"- Yeah... or whatever, right? Yeah. So I think that's the, um... But just doing it, it's gotten harder, there's more competition- Yeah...
but doing it smart is actually still a really good opportunity to scale those. What do you think is a really, like, what are some of the least effective growth levers you think?
I, I mean, I know, like, it's different for every person, et cetera. But, like, is there anything you guys have tried where you're like, "Ah, we just stay away from that now"?
So I think if you're only an ads-based business, like, forever, like, if you're an individual creator and you're like, "I'm just gonna use programmatic ads"- Yeah... like, through the Beehive network,
I think a referral system's, like, not great. Um, um- Yeah. Well, it's a little saturated too now. It, it's saturated. It doesn't actually do much,
um, uh, from a quantity perspective, and you're not really getting rewarded for those. You're not rewarding and taking advantage of those fans. Like, if- Yeah...
you had a product downstream, an event or something, like, big ticket that you were using to take advantage of these people that have referred three or four or five people, even if it's only 20 of those people, you know, that's, that's a...
If you're, you have, like, some, a big ticket item to sell that group, then that's pretty, actually a pretty interesting group to, like, go after and go target and identify. Yeah.
If you're just doing programmatic ads or something like that, then I think that, that, that channel's, uh, not just saturated, but just doesn't produce the ROI that people think it does. Yeah.
What about the content itself? I know it's, like, different people doing different types of content for different niches.
But, like, is there any, any, like, trends you notice that, like, oh, these types of issues are really performant when, when they're formatted like this, it's really performant. People love them.
The engagement's really high. Do you have anything about that? Um, so every audience is different. Um- Yeah. [laughs]... uh, so, and I think that's, like, actually the, the line there is, like, uh, I think,
I think form- formulaic content advice gets pretty shitty results. It, yeah. [laughs] Um, um- Yeah... so I think that's number one.
Um, I think that's what also, you know, what we try to lean into at Workweek is, like, that's also why having the creator be their ideal customer is- Yeah... the winning ticket.
'Cause if that HR person's like, "Hey, this is how I would want it. I would want, like, exclamation points, and I want, like, kind of-" They're gonna know better than anybody. Yeah. They're gonna know. All right?
Uh, if it's like, "Hey, I'm in healthcare and I want, like, graphs, and every data point needs, like, a graph," it's like they know already.
Um, so I think just, you know, being close to your customer, ideally as the creator- Yeah... but, like, either way, that's actually the way to find that answer. Yeah.
So, um, I wanna move on to some other things, but last thing, I do wanna talk about all the different businesses.
So, like, going back, I went through, I went through years of your Twitter, I went through years of Workweek's Twitter, um, et cetera, other things.
I, I, I know, I don't know if these are all still going, but at different points there, there was a, there's been a ghostwriting agency you guys acquired. Uh, there's a recruiting business.
You throw events, notably Marketing Land. Yep. Um, there's Crockett, which is a franchise business management tool.
Um, and then there's the professional networks themselves, and attached to, of course, the newsletters themselves, which, you know, you sell ads.
Is that the full extent of everything you're doing, and are you still doing all those things?
Uh, so our ghostwriting, uh, agency, we built actually a tool, uh, um, that we still have some clients, uh, for sure, which is interesting. Like, a lot of our advertising clients use that ghostwriting tool.
Um, but we actually use that internally. That's, like, how our team helps- Mm-hmm... manage our creators. And so, um, it's a, it's, we have a Chrome extension. There's, like, just a tool that we built off of that.
Um, uh, the hiring we don't do anymore. Um, and I can talk about, like, what the learnings there. Mm-hmm. Uh, Crockett we don't put any additional resources into. It is still live.
Um, and surprisingly, you know, I think I just looked, like, we did, like, added, like, 4K MRR this month or something. Oh, nice. [laughs] Um, uh, uh, but we did that. Um, and then Marketing Land we still do.
And then almost all of our efforts is around, um, scaling our ads business- That's the core... uh, through technology, as well as building out these, uh, professional network memberships.
Um, and we built our own platform for that completely, um, uh, for each one and, you know, integrating all those into, into one piece. Yeah.
Uh, are there any others you're current- any other, like, initiatives or projects you're currently working on? Or is it kinda like, like you said, it's all, we're, we're all ads.
The rest we're kind of not putting as much resources to at the moment. Uh, well, so, like, our memberships is, has, is ads and subscriptions- Yeah... is just kind of how it, it runs.
Um, and you know, it, we're, the, the north star of that is really, like, we think, you know, we have a, we have a feed in that platform.
Um, you know, we wanna create, uh-Social network for each profession that we're in. Um- Yes, which I really like... and- This was kind of something you launched this summer alongside a series, a Series A funding, right?
Yeah, correct. Um, and it is damn difficult to launch a social network- [laughs]... uh, more or less five of them. So- [laughs]... um, all of our energy is there, um- Yeah...
uh, right now compared to a lot of those other things. Yeah. Um, Adam as creator. So you- Oh, boy... are listed on the, on the website as one- Yeah... of Workweek's creators.
Uh, you have this newsletter, uh, called Perpetual. I... Looking at the archive, I don't know if it's been, like, a year since you've published, or if you've kept publishing and I just haven't seen them.
Um, and then you also have a podcast by the same name. Um, and then again, I think it was again on, uh, Jacob Donnelly's podcast, you said you didn't identify as a writer, and you never had.
And I'm sure that that disconnect kind of expands to podcaster and creator more broadly. Um, but I'm interested to hear how you, how you think of Adam as a creator. Uh, I wish I was better at it. Um, I, um...
So the, the kind of background and context, and I've, I've, I've kind of explained this, uh, I explained this to Jacob, but when we were going to market, um, you know, I could look people in the eye and be like, "I promise I will make you a very successful business- Yeah...
person through what we know how to do."
Um, but to, like, really have a true relationship and to give that, like, harsh feedback, right, uh, sometimes, you, like, have to have this, like, empathy that I didn't have yet of- Yeah...
and perspective of, like, what is it like to have a deadline? What is it like to have an advertiser, like, ask you to do shit that you don't want to? You have to walk the path yourself. You have to walk it.
And so, uh, on launch day, I, uh, you know, we launched myself as a creator talking about the media industry. Um, and it was really s- well, I could go through our own motions and see- Yeah...
what it was like, and kind of treat myself in our own system, and eat my own dog food, and it was, um, it was, it was... I mean, I published a weekly newsletter that was- Yeah...
like, o- on average, a few thousand words. It was a pretty in-depth essay every week. Um, I did my podcast and got all my dream guests on at one point.
So, like, I did the, um, you know, the r- the, the reality is it's just incredibly difficult to create quality in-depth content while running a business.
Um- Well, this, this goes back to the desire thing, when we were talking about- Yeah... the creators earlier. It's like your desire- Yeah... is to run the business, not to [laughs] create the content. Yeah, yeah.
And I, and I, you know, I... Jacob Donnelly and I are good friends. Uh, Brian Morrissey and I, you know, talk quite a bit, and, like, those guys are great. I think there was like a- Yeah...
I think there was a, there was a gap, and there's still, like, a gap, I give Jacob a hard time about this, in like the media industry of talking about tactics, but- Mm-hmm... um, like in-depth tactics.
But I think that I, that I touched on a lot. But yeah, my, my energy wasn't from that. Now, I will say I do an internal newsletter weekly that I- Yeah... send to the company.
Um, uh- But that's, again, that's the, the desire of running a business. Yeah. That's to run the business. [laughs] Correct. And so, you know, it's called Top of Mind, and I send it- Yeah...
every Sunday, and I, I love writing that. But- Mm-hmm... um, uh, so it's that. But that was the main reason is I wanted to put myself through my, our own process and, you know, we ran paid ads.
We did the whole thing, um, just to see how it would work and, um, I had, you know, um... And then once I, once I felt good about that system and process, I, I kind of started to pull back and back. Yeah.
Now, I, the podcast I went really heavy on this year again. I still think, you know, podcasting is the best way to network and meet people- Yeah... even if you hate it. Truly. [laughs] And so I, I love...
In Q1 I went hard, uh, and, you know, talked to the founder of South by Southwest 'cause I wanted to get an in there and, like, a bunch of other things.
Um, but the, the newsletter's been, been at least a year since I've published. Yeah, it was last September- Yeah... um, to be exact. How do you define the term creator? This is something I always ask people.
I'm always interested to see the slight nuances in people's answers. That's a great question. Um, I think on, like, a 30,000 foot overview, um, it's, it's anyone producing content at, at a consistent sort of cadence. Mm.
I think you can't claim being a creator unless you are committed to a cadence. Um- Yeah, I, I really like that. I, the, uh-... uh- One, one of, one of the ways I think about it too is, like, it's, it's about audience.
It's about you're producing it for an audience of people other than your friends and family, other than people you know in real life. Yeah. But I hadn't thought of the consistency. I always say, like, the only...
Was talking earlier about like, uh, you know, hard to give generalized advice for this kind of thing or say like, "Oh, here's how content should look like."
Like, I think the only advice that really matters is, like, post, analyze, tweak, repeat, and that's all it is, right? Yeah.
And, and I think, like, you know, I like operating these, like, niche spaces because sometimes just, like, consistency does win. You can- Mm-hmm...
have an off month or two, a hard season of life, but you just keep showing up and no one else does, you still win, um- Yeah... there. And, uh, so I think cadence matters a lot.
Um, and I think, like, the, the commitment to that is, like, what gives the title of creator to me. Um, and also phonies like myself that stop is, like, what makes you lose that, I think, right? Yeah.
So I think that's the, that's the key. I think you could talk about, like, intention a little bit too. I don't think marketers are creators. Mm. Um, I don't, I think when you're, like,
creating content for the sole purpose of selling something- Yeah...
uh, you're not a creator, you're a marketer, and there's- Well, I, so I also think with this, um, that a marketer, like myself, you know, the full, my full disclosure is that, like, Beehive pays for my salary and Beehive supports this, and, like, so I think I am...
I can't be a creator, because I think to be a creator, you have to be solo, you have to be, like... Well, not, not solo, but you have to be independent.
You have to be essentially working for a mix of yourself, uh, the audience, and then if you're, you know, on a platform like YouTube or another of these revenue share platforms, you're essentially working for YouTube too.
But you, if you're, like, if you're doing all those exact things and y- you're like, uh, you know, a content person at a company and you're making YouTube videos, Instagram, TikTok, a newsletter, whatever, you're doing all that, but a company pays your salary-I don't think you're a creator.
You have the same skills as them, but you lack the risk and precarity and particular motivations. See, see, I don't, I don't, I don't make creator around entrepreneurship. Um- Yeah.
I don't think it's a signal of entrepreneurship. Interesting. Um, like, I, I, I go back to, like, what's, like, think about what's been existing. Like, I absolutely believe, um,
you know, um, uh, to go to, like, the Friends example, like, the- they're creators. Yeah. They, like, create amazing, amazing art. Um, and they do it consistently. They get paid by NBC. That- Yeah...
that doesn't make them not that. And I think HubSpot's another good example. Like, there's... It's not that ultimately that content's not meant to drive sales for HubSpot.
But I actually think, like, the spirit of what people are creating there, um, on that, like, media arm of HubSpot is, like- Yeah...
they just are trying to actually, like, do good solid work, and they're doing it for this, like, audience, to your point- Yeah... not to necess- They're not saying...
They're not producing something and being like, "If we didn't sell this, we fucking messed up." I think of it as, like, you're just contributing to the corpus of the internet broadly- Yeah... is also in that way.
And, like, I don't think you hang up, you know, a, a pod and, and, you know, and say, "Oh, we got no Beehive leads off of this ad." No. "It was a failure of a podcast." No, no. Of course not. That's not really the point.
Yeah. And so I, I think actually you are a creator then in that sense. It's about, I think, the intention. Yeah. And I think the difference is if you ask a marketer, you're like, "What's the intention of this?"
They're like, "Well, I better sell something." Yeah. Or, like- Leads, leads, leads... leads, leads, leads. [laughs] Or, you know, I, "I wanna, like, change the mind and influence for my product," whatever.
If you ask a creator, it's like, "I'm trying to create valuable content." Yeah. "And I'm, like, doing it on, on a, on, I'm doing it really for them, not for me." That's a really good answer.
This, I feel like I've been... Uh, recently when I've asked people, we've kind of gotten stuck on the same things. This is...
I- nobody's ever really pushed back so much on the, uh, like, you know, if you're employed by a company thing. Um, so I like that.
I wanna go back to much earlier in your life when you were a campus rep for, um, uh- [laughs]... HP, Procter & Gamble- You, you went back [laughs] and Red Bull. Yeah, well, that's my job. [laughs] That was 15 years ago.
Uh, you know, that's what you gotta do to create that good content. But I'm interested in this because, like, you know, I just, I just, I just read... Uh, to, you know, full disclosure, I just read your LinkedIn.
It's on your LinkedIn there. You, you have a really nice thorough LinkedIn. Um, but to me, there's, like, a clear through line to what you do now. Um, I, I don't know. I...
You don't have to tell me [laughs] every detail about, you know, slinging Red Bulls out of a, out of a, out of a Mini Cooper or whatever.
But I'm curious, like, the through line of what you've done in your work that you, like, take from, you know, 15 years ago to now. Yeah.
Uh, I mean, my college experience had a huge influence of, like, what I'm doing today. Um, first off, I, I, you know, my, my story is, uh, my mom, uh, was a nurse for 35 years.
My, my, my dad worked at a grocery store and then- Mm-hmm... um, uh, uh, w- got into real estate, but, uh, both didn't have a undergrad degree. And when I was- Yeah...
doing my summer welcome, we were walking past the business school and my mom was like, "What do people do with a business degree?" [laughs] And I was like, "I have no clue." Yeah. Hell if I know.
And, and that's, that's how I became, I became a teacher. I got my undergrad in education, I got my master's in education, and I, I love teaching. Um, I love that aspect. Mm-hmm. I...
My master's in workforce education focusing on adults. Um, and it's so much of what I do today is- Yeah... is coaching. Um, and that's really where that comes from. But- Makes so much sense...
um, but in college I needed money. Um, and I, uh, always kind of, like, was coming up with little side hustles and rackets that were mostly, like, marketing based.
Um, and I would sell, like, T-shirts and design them and stuff like that, like, classic kind of freshman year stuff. And, uh, yeah, I got a...
I sought an internship, uh, for Procter & Gamble to be the Old Spice kind of campus representative- Yeah... of how could you come up, come up with, you know, funny, clever marketing campaigns.
It was kind of peak Old Spice advertising at the time. And, um, you know, I, I did all sorts of stuff. I did, like, bathroom makeovers at gross fraternity houses where, like- [laughs]...
I hired a cleaner to come in and actually make it, like, really nice and then, like, put, like, soap everywhere and then I, like, put- And these were your ideas, not, like, passed down- Yeah... marketing ideas.
They were, they were my ideas, and I kind of led that off there. And then I got promoted there to oversee multiple brands.
So I had Cheer and Old Spice, uh, uh, one of the shaving companies, like, uh, the razors for women.
And so at Cheer, I, uh, I, uh, went around and asked all the fraternities if they could ask their pledges to dress one day in, like, neon colors, and I would, like, basically pay them for, like, a night of beer.
And so one day, like, the whole campus was running around in, like, neon colors- Yeah... and I gave away, like, Cheer. Just, like, fun stuff like that.
And then I left there to go to Red Bull, and that was really where my mind was opened up about brand. At that time, with P&G it was mostly, like, just, like, come up with crazy shit.
You have this, like, budget that's really low. Just, like, be fun and be creative. Red Bull was, like, got taken into the Red Bull, like, school. The dos and don'ts of the brand.
How can you present the c- like, all the stuff. And then, um, you know, uh, uh, the Mini Coopers was a separate thing. It's actually, like, a totally different team. But, um, you know, and- Well, this is also...
They're such a, a... Speaking of, like, the Disney model and, like, that drawing of all the businesses connecting, like, Red Bull's another modern master at that, right? Perfect example. Yeah. They're the best. Yeah.
I mean, they're...
And, um, and I, you know, I, I was exposed to just, like, one, like, don't ever say no, was, like, that's where that was made as, like, "Hey, we wanna shut down the busiest street in the city and have people make, like, chariots and race them down there.
How can we make it happen?" And- Yeah. Find the person- You know... to talk to.
I went to town, I went to the town hall meeting, like, 12 times till the mayor would sign off on it, had to get, like, exclusivity agreement with a bar to, like, sign... It was, like, crazy. 100%.
You just, like, did, did crazy stuff, and you learned a lot about being, like, an entrepreneur through that. But, but also the brand values never went away. Mm-hmm.
Um, and I think that was, like, so much of what I carry with Workweek today and what I, like, look for is, like, how, what do you stand for, and, like, it should exist in everything you do in- Yeah...
subtle ways to, like, very obvious ways.
And, um-Uh, and you know, with Red Bull it was like, hey, I had like a gaming group, I had like the, the nightclub group, I had the convenience store, which is more blue collar workers. Mm-hmm.
Like, we thought about different audiences and different ways and activations, and like it just... But the values never changed, and I think that was, um, there was so much there that I, I thoroughly enjoyed.
And I, I made a lot of money relatively in college for that. Yeah. And, uh, my friends never had to buy a drink ever, and so it was, uh, it was a good place to be. That's sick.
No, I mean, there's a few, a few things there, but one thing I'm really picking up on is what you were just saying at the end, is like it really taught you a lot about values driven businesses, and like adhering to values, and like how that is what allows you to grow.
And like that's like the tree trunk that, you know, makes everything solid around it. And I don't know, I think it, it makes decision-making easy.
Like, you know, whether or not for you now it's like, are we gonna hire this creator or not? Like, they're, well that's not, they're not really about business. Our values are all about like serving business niches.
We wouldn't hire them. Um, I don't know. It's hard. I think it's values. A values driven business is easy and hard. It's hard to like... I- i- if you're faking it, it's hard, but it's really easy- Yeah...
when the values [laughs] are real. Yeah. I mean, I just met with a creator, uh, today, a group of three guys. Mm-hmm.
And they have a TikTok channel I think with like 8 million people, and I've been meeting with them since they were like 500,000 or something. They're incredible.
Every part of me and every part of my body like wished I could work with them, and it's not what Workweek does. Yeah.
And so, you know, those are the things where your values are tested, and you're like, every part of me wants to say yes, 'cause this group of people, like I've known from the beginning they were gonna be fucking stars.
Yeah. And now they are, and I'm like, "Ah!" But you just have to like- I could have been in a... You also have to just totally believe in what you're doing.
Um, and, and I think the, the mature thing there that you learn, I think when building businesses, and even with creators I think, you know, as they develop and grow, is like you, you learn opportunity cost.
And like, you know, uh, we've, we parted ways with a lot of creators last November. Yeah. Uh, and it wasn't, you know... There was some data reasons that drove that decision for sure across the board, but, um,
also it was the opportunity cost of like on the flip side we had like a group that was crushing- Yeah... and I wanted to go all in on them. Consolidate resources.
And every, every single resource I didn't have that was actually costing us on that opportunity. And so I think that's, as a creator, you also kind of tend to realize that too. Yeah. No, that makes sense.
Um, okay, how about, so the newsletter industry, I know you were working, you were doing some media stuff, um, before The Hustle too. Yeah. But that's really where you start doing newsletter first media.
So you've been working now in, you know, newsletter like... Oh, I see you kind of shaking your head. Were you doing newsletter stuff before? Yeah. I mean, like, I mean, like newsletters have existed.
I think it's like, uh, kind of a bubble that we all live in today. Like, and I mean- Yeah... newsletters were on like media plans, like, you know, uh, PopSugar sold for 100 million in like- Yeah... 2000.
So like I think they've been around for a long time. No, no, but, but you, you specifically working in them. Yeah. Did, were you- So I, I- Yeah... SpiceWorks had newsletters.
Uh, we had like a couple million people on those lists and the things. Yeah. But it wasn't, it was, it was a community, so it was different. But, um, uh, MyFitnessPal had a massive, massive newsletter list- Yeah...
of, uh, people. But to your point, they weren't newsletter forward, which- Yeah... that, that was the big turning point, um- That comes with Hustle, Skimm, et cetera... was, was The Hustle, uh- Yeah...
of being like, what is the new homepage was actually the question I was asking. Yeah.
Well, so okay, so then in the eight, eight plus-ish years that you've been really working with newsletters, uh, what do you, what are some of the most pronounced differences in the industry from your personal pers- perspective?
From eight years ago till today? Yeah. So, uh, my, so the, uh, the, before The Hustle, I sold advertising. I had one client that did about six and a half million dollars with me, um, in one year. Wow. It was HP.
And I like had a deep relationship with, you know, their management team and knew them really, really well. Enough where I was like, "Okay, this is who I'm gonna bring in-" Yeah...
"uh, to The Hustle, uh, pretty quickly." I will never forget it. My contact who, I mean, I've known this person, I knew her kids' names, right?
Like I knew this person really well, and I sit down and I'm like, "Hey, I have a pitch for you." We took her out, I took her out to breakfast and I was like, "I have a pitch for you. I'm moving companies.
This is, this is what it is. It's, you know, think about The Daily Show, but for, for tech and business news. And then the, we're gonna be in your inbox. Your inbox is your new homepage." Yeah. And,
uh, I was like, "I have a two quarter proposal, so six month proposal for 100 grand." Um, and I mean- That's chump change compared to six million over the previous year.
I mean, I used to get calls like, I used to get calls from her the last day of the quarter and be like, "Hey, I have 200 grand I have to spend today or it gets taken from me next, the next quarter." Like, I was like...
So the, so I'm like, "Is it..." You know, I expect it to go down a little bit, but I was like, "Hey, let's just like start- Yeah... somewhere like that." And she's like, "A newsletter? Really?"
And she's like, "Why a newsletter?" And she's like, "Why don't you guys do like banner ads and like g- do, you know, I kind of buy banner ads on the site. Like what's your home, what's your page views?"
And I was like, "Holy shit. Um, this is gonna be harder than I thought." Yeah. [laughs] Um, and today that doesn't exist. Um, those conversations, no one asks- Yeah... like why a newsletter anymore.
Um, that, they get it. And so that shift, and, you know, we watched it in real time happening.
It's like these agencies started inbounding and like being, putting it in their annual plans of like, "Oh, we need to sponsor these newsletters." Yeah.
And I think like that, that shift is obviously, is in my opinion, is why the Beehives could exist today and not eight years ago. Yeah, totally.
Um, um, because the do- the pool of dollars has just gotten so much larger that it's allowed more people to enter the space. Yeah. Yeah.
Um, is there anything like in the industry broadly, not necessarily like about Workweek, but like anything more in the space that worries you or like you kind of keep an eye, like a, a watchful eye on, you know?Uh, I mean, I definitely think there's, like, huge risks to the email providers rolling up newsletters- Mm
... um, which would be pretty detrimental. Um, and I would expect a change like that. It's gonna happen. Um, not all mediums last. They never do. Um- Yeah...
and so, you know, something's gonna happen that fundamentally shifts that behavior, user behavior, whether it's a force function of the big players or just, just the world changes consumer habits.
Something's gonna happen that's, that I think it'll- Some other shoe is gonna drop. It's going to happen. Yeah.
It might be in 20 years from now, and none of us really care that much anymore, um, but it might be in three years. Like, we don't know. And so something that I think about, like, a lot of, like, what is- Yeah...
you know, what... And, and I went through that. Like, basically 2016 was me being like, "I think the page view business is done." Yeah. "I'm out." Um, and so I, you know, just I'll, uh, I think about that.
You're looking... You're, you're, you're waiting for the next version of that. Yeah, I do, uh, for sure. Yeah. And I think- Yeah... uh, you know, I think, um, these... And I, I,
I, I say this about everybody, um, but, uh, that does these, like, you know, sign up for five emails at once, buy a checkbox. Yeah. I think they're terrible for the industry. Um- Yeah...
um, because it's, it gets into the page view business. Um- Completely... it's the same, same thing. So that's the, um, that's one thing I think about. Uh, I think the other one is just, um, you know, it's not...
Quality will always win. Yeah. Uh, brand always wins. Um, so, like, I'm not worried about that, but it will get more expensive to s- have quality stick out. Um- Yeah... and because marketers are simple people.
Um, and it used to be, hey, if this list was big, it meant it was the best. It's not the case anymore. Used to be open rate was great, but now- Yeah...
some people do it in a- Well, wait, actually, something, something, uh, that from this weekend, when Daisy and I did the Tasteland live event, and we had, um, people from, you know, these few worker-owned journalism outlets.
We had 404, uh, Hellgate, and Defector, people from each of those.
And at the end, we let the audience ask a couple questions, and, um, Adam Boumas, Boumas, who write, who's the researcher for Garbage Day, Ryan Broderick's newsletter, asked about, like, "Well, do you guys, like, are you competing with creators?
How do you think about that?" And Sam Cole from 404 was like, and they, they all kind of said a version of this, like, "I don't really think of that.
Like, I think we're doing different things," which, you know, I think there's room for debate there. But then Max, uh, from, from Hellgate was like, "Well, I think, um,
the, the difference is, like, you know, these newsletters really, they don't have an editor." You can really tell. Like, the quality isn't necessarily there.
There's not, like, the polishing of having an editor, of having other people in the newsroom pushing these ideas.
I don't know if that gets at, like, what you're saying about, like, quality will always win, and, like, when, when the, when the zone is a little flooded, quality is lower.
But I, uh, that's something I've been thinking about since he said that. Yeah. I mean, I think-
Which is a problem you guys solve at Workweek because there is this team, and I imagine there is editorial collaboration, and, like, even between the creators and w- you know, between the team and the creators, I imagine there's that kind of polish being put on the content.
Um, so actually not really. Um, and- Pretty, everyone's pretty solo... so let me, let, and I'll tell you why. Phil- Yeah... it's a philosophical approach, not, like, an operational one.
Um, so one, we have Lindsey Quinn, who was the managing editor for, from November of 2016 until basically 2020 at The Hustle. She- Mm-hmm... she's, she ran the whole thing every day. Yeah. Saw it over six days a week.
She's incredible. So she's our content coach, and she's helping everyone get better at writing. The craft is real. Yeah.
But there's, you know, and this is my opinion, and I think there's a lot of counterpoints to this that I totally buy into.
It's just kind of where I'm at on the B2B side is, you know, um, when we wrote our first memo, I talked about this, essentially the evolution of attire and how 30 years ago you had to wear a suit and tie, and that's how you found credibility with someone.
Yeah. And if you showed up to a meeting in, you know, a, a, a T-shirt and sneakers, they'd be like, "Who the fuck is this person?" [laughs] Today, that doesn't exist. Uh- Yeah...
you can be actually really, uh, almost more credible in some ways- You go Zuck mode. Yeah... if you go Zuck mode versus, like, showing up to a suit and tie.
And I think in B2B content, we're on that same horizon, where actually if you can be, like, succinct and do it in a meme- Yeah... and do it, it, like, fucking hits, you actually are more credible with people.
Like, oh, they get it. Um, versus, like, this, like, very long, uh, you know, multi- Well, the, the attire is the sender. The attire is the name of the creator. It's the Twitter handle. It's whatever, you know?
It's the identifier. And the s- the style as well, right? Yeah. Mm-hmm. And so, you know, I personally, I tell this to the creators all the time, one of our values is press publish, don't be perfect. Yeah.
Um, and a typo means you're human. Um- Yeah... and, like, today that's actually more important than, like, ever before, and I don't care about a typo. Yeah.
Like, it needs to be clear and concise and understanding, but, like, it's okay if you, like, make a mistake on the format. It's okay if it's not polished, actually- Yeah...
because, like, polished is what's now being audited. It's about the idea, not the vessel. I mean- Right... it's still about the vessel, but the vessel can look different as long as the idea is the core.
The, the insight is what actually matters- Yeah... in delivery, right? And, like, um, and so that's, so that's how we think about this polished, just to go on that, like, rant. Yeah.
That's how I think about polished is actually, like, unpolished is polished in a way. Mm-hmm. Um, and, um, but the...
What I mean by quality standing out is it just, like, ultimately what people forget, there's only two ways to make money with content. Yeah. It's ads or consumer subscriptions- Yeah... essentially, you know?
And most of it is ads. So how does a marketer make a decision? They normally look at, like, it's like looking at a resume. Someone looks at the brand for, like, one second.
Like, and you look for the key thing that you care about. And it used to just be, like, in 2018, once we started, like, growing well, you used to be like, "Oh, wow, they have a million subs." Yeah.
Only, like, three other companies do. They are, they gotta be the best. Clearly they're the winner, yeah. Yeah. And then you look at open rate maybe as, like, a second glimpse, quick thing.
Mm-hmm.Today, both those metrics basically are meaningless. Um, so like no marketer trusts those anymore.
And what I mean by the, the thing that I think about and am worried about is then how do the best newsletters that deserve a four X premium CPM and deserve like the actual high, high brand get in front of those marketers in a way that stands out?
Um- Is it first party data? Um, I mean for us, we like, we invited all of our top advertisers to an event in person. Uh, we called it our upfront event- Oh, yeah...
in September, and we flew them all to Austin and got to sit down with them and explain, you know, our content process, the product pro- like meet the creators, like- I mean, it's, it's hard to get more real than that.
Yeah, right. Uh, but I, I actually think that's the era we're in. Yeah. Um, and so, you know, but like that's more expensive than it used to be. Um, and so that's, that to me, you know, I think quality will always win.
I like deeply believe that, but like the time to get in front of advertising, I think we're gonna see this huge disparity and, you know, I talked to Daisy about this a lot at Dirt. Yeah.
Like I think their quality is the fucking best, and they struggle at times with advertising, uh, because it's just not correlated as much as it used to be. Yeah. And so you have to like...
That, that I think is a concern for the industry kind of at, at large. Yeah. No, that makes a lot of sense.
Um, some, okay, so some other newsletters that you have advised, I don't think you're currently advising all of them. I mentioned some of these at the beginning. 6:00 AM City, Every, Matthew Berry's Fantasy Life.
I think these are all other newsletters or newsletter businesses that, you know, speak to that kind of quality we're just talking about.
Tell me about, and I imagine that these are just the ones that were on your, your [chuckles] LinkedIn page. Again, I think there's probably some others that aren't.
Um, tell me about what these relationship, relationships are like and how you're helping them, and are you reaching out to them or are they reaching out to you? Local newsletters, I love them so much.
Um, you know, Daisy, um, Payload's Space I did before launch. Yeah. Um, uh, Every, Dan and Nathan, I, I talked with, you know, early, early days as well.
And, um, you know, I, I hoped to give them any insights I could about, you know, building monetization strategies, newsletter growth strategies, et cetera, um, and correlating that.
But the reason why I really worked with all of them is 'cause they all had a very content forward approach. Yeah.
And I think the thing that I left after The Hustle that I, I, I could see happening, and, and Beehiiv has amplified this problem because it's democratized access- Yeah...
which is amazing, but the problem's been amplified where there's more shortcuts. And if, if, and this is why Workweek exists, the way that we set it up is like- Yeah... I think ultimately
you have to have the best content. And what all those people had in common is they just deeply cared about the content. They didn't even care about the business in some way, in some cases. [chuckles] Mm-hmm.
Um, and I try to help them in those capacities and, you know, Matthew Berry just, I mean, the man lives and dies fantasy football content. Yeah. [chuckles] I read it. I love it.
They needed support on, hey, how do we think about larger advertising sales and six-figure, seven-figure deals? Um, you know, uh, Every was, they were doing like a house of brands model at the time. Mm-hmm.
And how do we like think about that? So I just always would help that.
I, I think like ultimately those are, those are, those are relationships that my kind of goal is I try to help them avoid a landmine or two that I've stepped in. Yeah.
And, um, and that can be helpful and, but also just to, to be an advocate for them at anywhere I can be.
Uh, those landmines, are there one or two of those kind of landmines that you would, you know, for more of the indie, more, I don't know if entry level, but like still lower scale newsletter operator who might be listening to this, what are some of the main landmines you would suggest [chuckles] avoiding?
Um, learn how to say no. Um, I mean, and no to advertisers, no to clients, no to... No, no, no, no, no, no, no. Um, one, nothing sells sexier than no. Yeah. So like it doesn't mean you don't get a yes.
It means you just have the leverage. Yes. Um, and so say no, um, more. But also that comes with focus and time.
Like try to choose the thing that gives you the most energy that you love and do it, and like that sounds like not advice, it just sounds obvious, but actually all the mistakes you will make when- Well, it's so hard to know when to say no, and this comes back to the values driven business stuff we're talking about.
Right. And like, but all the mistakes you'll end up making are the moments that you should have said no. Um, and so that's, that's like the, the top stuff, um, to do and, you know, uh,
you'll, you'll find points where you're like, "Hey, I'm gonna say yes here," but like then if you do, and, you know, we all...
I, I talked to our sales team about this early days, like there's deals you just have to say yes to to keep the lights on, right? Yeah. Like, you're like, "I don't, I don't love this."
Like we have a block list where we don't work with advertisers that we don't like, but like early days that list was, uh, pretty limited because- Yeah... like we just needed money.
Um- You can't say no 'cause you have to say no to the lights turning off. [chuckles] Right. Right. And so, you know, but then draw that line. Like, you know- Yeah...
that's still like in your values, but be like, "Hey, once we get to this goal, no more of that."
And like that, that ability and that focus and that mission and keeping to those, those, those, those values, but just being able to also, you know, say no, all of a sudden all your work compounds. Yeah.
And I think that's the mistake, the landmines I've stepped in, is you don't create a system and process that compounds, then you actually become pretty disparate and nothing three years in feels like it's huge. Yeah.
No, that's good advice. Um, one more, another pedantic question. Just like I asked, what is a creator? What is a newsletter? It's a format of content, um, that, uh,
can be consumed within a single sitting, delivered on a, some sort of consistent cadence. That's really good. That's a tight definition.
I've, I've, uh, my latest definition that I'd used was an email sent one to many that's not a transactional emailSee, I, I, I'm, I'm old. Newsletters can still be in the mail, my friend, physical mail. That's true.
That's true. [laughs] Uh, uh, uh, I'm actually, I might, uh, you know, you start having friends send their, uh, holiday newsletters. Yeah. So it's a real thing. Um- Come on, you're not that old.
[laughs] Uh, but, uh, I got, I got a f- I got friends that send me their, uh, annual holiday newsletter of their family- Yeah... uh, in the mail. Mm-hmm. But, uh, yeah, I think, I think the key...
I don't talk about intent there, 'cause, like, I do think that's, like, too hard. Yeah, yeah. I think the key thing with definition of a newsletter is, uh, like, what it solved originally- Mm...
is what the homepage solved, which is, like, I can quickly get this, I can consume it fairly fast, like, in one sitting, and it's consistently kind of there. Um- Yeah...
um, I think that difference of these transactional emails, um, is, um, you know, I, I think you...
And this is where I, like, go back and forth of, like, I used to say all the content, like, and I think actually maybe I would say that, like, uh, you can, you can consume, um...
Like, I have a hard time calling emails- Yeah... that just have 30 fucking links in them newsletters. Okay. Um- Well, there has to be some commentary or something.
Well, like, I used to say, you know, at The Hustle early days, it was, like, we used to just, like, tell us that everybody's, like, 100% of the attention in the email unless it's the ad. Yeah.
Like, we were so minimal with link outage, and that was on purpose. Um, and, like, w- until we realized- Don't give anybody an off-ramp to somewhere you don't want them to go. Yeah, exactly.
So, like, attention in that format is one of the things that I think is, like, an updated potential way to think about newsletters is, like, where is their attention going?
But, like, realistically, it's just a format, and how you choose that attention is, like, up to you. But, um, people that, like, l- just use it as a link out is I think a different, it- Yeah...
it's a different type of a newsletter for sure than probably most of your listeners have. Yeah. Okay, well, we could talk about that bit for probably another hour, but one actual final question.
So you are just over now three weeks, or three years into Workweek. Um, where do you want it to be at the five-year mark?
Um, you know, I, I h- I hope that we become this, like, third home, um, for the professions that we have. Um, I think we've built a lot of habit.
Um, we-- I talk about, I talk about, I talk about hits and habits a lot in content. Mm. Are you in the hits business or habits business? I'm in a hit- I'm in a habits business.
Um, newsletters are great for habit building. Um, but the next thing I wanna do is build a home, um, where if you're in HR, you have your work Slack, you have your, like, friend text, and then you have safe space.
Um- Yeah...
uh, our membership for HR, you know, healthcare market, kind of go down the line, and really, I think in, by the five-year point, I think for, for the ones that we're building today, we can, we can achieve that in the next two years.
Nice. Cool. Well, that's it. Thank you for coming on. Yeah, thanks for having me. I appreciate it, and, uh, I'll maybe look forward to doing it again. Absolutely. Uh, this has been the Creator Spotlight Podcast.
I'll see you next week.
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