Newsletter & Email Growth: Growth In Reverse

Growth In Reverse Podcast - Interview with Nathan May of The Feed Media
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Dylan Redekop: [00:00:00] Did you say you're running $1 million ARR with a thousand person list?

Nathan May: Yeah. If you're gonna buy a newsletter, like you wanna be really careful about it.

Chenell Basilio: It's definitely easy to build, just like a list that doesn't have any quality behind it, and then sell it and

Nathan May: hope for the best. The leverage in the newsletter is like, it comes from you and it's.

Your words and 74 replies, they replied to you.

Chenell Basilio: If you're not in this for the right reasons or you're not gonna stick with it more than six months, then just don't even start. It's not worth it.

Nathan May: First question you ask is not how I get the subscribers. It's like, how am I gonna monetize when I do have them?

And for most people it should be.

Chenell Basilio: Nathan, I'm excited to have you on the show. We, you and I just get together randomly and jump on calls or have coffee and talk through newsletter stuff. So thought it'd be fun to have you on and just kind of talk newsletter stuff.

Nathan May: Guys. I'm uh, I'm pumped to be here. Yeah, this is awesome.

Chenell Basilio: Yeah. Do you wanna tell people a little bit about yourself so they have some context of who you are and why you're [00:01:00] interesting?

Nathan May: TLDR on us? So I run an agency, um, we're called the feed Media and we do pay growth. Uh, for a lot of the biggest newsletter brands, people are spending 50, a hundred, 300, $500,000 a month on newsletters. Profitably. And we do that for like, we'd all Facebook ads. We do that for two groups of peoples, like personal brands, people like, uh, Arnold Schwartzenegger, Jesse Fuji, Tyler Dank, and then what I call like media or newsletter native media companies.

The neuron, the rundown, the point sky, stuff like that. That's my, uh, that's my world.

Chenell Basilio: How did you get into the newsletter space? I don't think I know this answer, so I'm curious.

Nathan May: I'll tell you something crazy. Uh, so, so it's weird, right? 'cause all my, like, uh, everybody in this space is friends, but tech, technically my competitors or whatever, they, they, they came from like newsletters, right?

And one of 'em worked at the Hustle and the other one worked at, uh, at Morning Brew. Um, I didn't do any of that stuff. Uh, so I, the way I found about newsletters was I used to run a big. Mobile app portfolio, like 15, $20 million mobile app portfolio. We, we raised a bunch of money. We were buying mobile apps from, from indie entrepreneurs, and I [00:02:00] thought mobile apps were like, I don't know, like little widgets.

It was like, oh, this is like cute. And it turns out they're, they're super badass businesses. So for instance, they're these two guys. They have a newsletter. So I'll, uh, this will be full circle, but Dave and Joel, these two Singaporean guys, and they had a, a $12 million a year, uh, mobile app portfolio, uh, with like 50% EBITDA margins, which is, is wild.

Um, and it crazy stuff you'd never think about like l logo makers or like screen recorders, like ran random little iOS apps on, on your phone. Uh, they don't know how to code. Uh, uh, they had like a Indian development team do the whole thing. And that whole team in aggregate was maybe $400,000 on, on $12 million in revenue.

So, so nothing, it's like 3% revenue. Um, anyway, uh, so. They also had a newsletter. They did a million dollars a year. They didn't write the newsletter. Uh, and they did a supplement brand that did like seven figures. They're just like crazy direct response marketers. And I thought like, oh, to have a big company, you gotta, you gotta go to a 16 C, you gotta go to Sequoia, you gotta, that's like, you gotta raise, that's what it means to have a company.

[00:03:00] And then these guys were just getting after it. And in the same way that like, mobile apps were badass businesses, I thought they had that newsletter. I was like, oh, I bet newsletters could be that too. They knew about Sean Purry and the Milk Road and Beehive. Um, and that's how I went down the, the newsletter Rabbit hole.

Chenell Basilio: That's fun. So

Nathan May: you, you started working with them. Was that essentially what happened? My first client was, uh, the neuron or, or these two, two folks, the neuron. And then, um, oh my gosh. Uh, this guy Julius. Uh, Julius who writes a newsletter called Bold Push, he, he, like, he's a big LinkedIn influence and always talks about as like, events and event marketing.

So those are my two, my two first clients. That's pretty wild. And here we are now. Yeah, it's cool. Yeah. Yeah. I, I had some small newsletters too. I, I had a, I never talked about this 'cause it wasn't like a, a big deal or anything, but I had like a, like a tiny crypto newsletter, uh, that I sold to the, the Milk Road and then, uh, the Feed, which is my agency.

So the feed was like, you, you scroll the, the feed, like social media. That was the idea. But, um, it, it, it was a, a newsletter. So I used to do, uh, I always was obsessed with founders who [00:04:00] had built audiences and how much of a flywheel that was, you know, for like Sam Par, you know, Sam Parker start any company he wanted.

And he has this religious group of people who love him, who, who would support him in everything he does. And I just thought that was incredible. There's so many people that are, are like that. Justin Wesh, Alex Becker, a bunch of different folks. Um, so I used to do case studies, um, on these types of entrepreneurs and a lot of 'em had newsletters.

So actually technically, like originally the Feed would've been a newsletter that. I think technically would've competed with growth in reverse. Nice. Like back in the day, 'cause I was doing like case studies on like very similar, uh, people and I, I would look at like, like I did the, uh, I did a case study on like Justin Walsh and so I, I read your, uh, write up on Justin and like, I watched like a bunch of podcasts and Justin, so I I was reading your content like all the time religiously.

I love it.

Chenell Basilio: That's awesome. I didn't know that.

Nathan May: I don't think we've talked about that. No. Yeah, yeah, yeah, yeah. Yeah.

Chenell Basilio: That's super cool. That's cool. Yeah. That is cool. Yeah. Awesome. Yeah. Um, and so now you are working with some of those folks and then you've gotten connected to other people that you're working with through those.

Um, I know [00:05:00] that neuron is one that you talked about all the time. You actually almost bought it when they were going to sell. Um, so that's a fun story that I'm sure will never be un painful for you.

Nathan May: Yeah. Uh, that sucked. I still think they should have sold it to me. I think I. I think I would've been, I, I like the, the guy who runs it now, he, it's this awesome dude, this guy Rob, uh, Ballant.

He is, he's a crazy bootstrap company. So they, they've gone, he started in college and I think they do, uh, this is like what's public. I think they do like 40 or $50 million a year. Something, something really big like that, uh, with a bunch of like lead gen and newsletters. And they're all kind of like B2B media properties.

They're, they're kind of like an industry dive or stuff like that. So we lost the deal to, to them. But, uh, it was cool. It was cool to see like the, the deal process. And there were a lot of like, I don't know, things I would've done. It would've, uh, the deal would've closed in January, and so it would've dramatically changed how I treated this year.

But the whole idea was, uh. I mean, I knew everything about the neuron 'cause we'd done their growth and my buddy Walter did their [00:06:00] ad sales. And so like, uh, we just knew everything. And I, and, and we worked with their largest competitor, uh, the, the rundown as as well. And so, like, it would've been cool, basically I would've bought it and we would've continued to grow it.

And there's some tweaks we would've made to the, to the growth, but it would've been 90% the same. And then I was gonna do like the industry dive playbook so people don't know industry dive. It's a super badass. A portfolio of B2B newsletters. They went from zero to $110 million a year in like 10 years, something like that.

Seven, seven or eight years. And then they sold for $525 million in like 20 21, 20 22. But they would have super B2B stuff like, you know, waste management dive and you know, education dive and they had retail dive, marketing dive, all the different stuff. But their whole thing was they would get, like, it wasn't about how many people were on the list, it was about who was on the list.

And so they'd have all these CEOs and stuff. And then they do really high priced like webinars and white papers, like all this deep B2B stuff. So you've got your, your newsletter sponsorships, and it's like, well, how do you fully monetize the list even [00:07:00] more. So we would've done that. And then the other big thing.

We were gonna do. So I'm a huge fan of, uh, the idea. I think it's awesome when enemies become friends. So, so for instance, like, uh, so Sam Par from the Hustle and Austin Reef, they, they hate each other, right? 'cause they, they used to run like, competing newsletters and now they're literally best friends. Yeah.

They spend a ton of time together. Sam, uh, just moved, uh, back to New York City and he was going to buy a place. He, he didn't win the bid, but he, he was bidding on a place, an apartment in Austin Reef's building so that they could live together and raise their kids together. Like, that's how close they are, which I think is like amazing.

That's awesome. So my version of that is, um, Rowan and like the neuron and the rundown. I, I, it's not, I don't think they like, dislike each other. Right. But they're not like, they're not like going skiing together, you know what I mean? They're not like besties. Um, and so Rowan has this incredible AI community that sit behind his newsletter.

Um, the neuron did not have that. And so we had a, like a affiliate deal worked out. So I, I would've just like done all the work that we do, which is like driving traffic and like [00:08:00] converting that traffic into people who, who buy, but for Rowan's community. Um, and I think that would've been whatever, maybe 300 to $500,000 in the first year, which is like, you know, basically straight down to ebitda, right?

Because there's no costs, right? Just the team we already have, like doing what we do for other people. So yeah, it sucked. I want, I want to get that deal.

Chenell Basilio: That would've been fun to have like that audience to just build the monetization around, which is something that I feel like you love doing.

Nathan May: Yeah. It would've been cool.

And I think like, uh, part of it's too is, is like an agency owner. This happens a lot in e-commerce, like agency owners will become brand owners and I kind of wanna do that. Like, I, I like running the agency. I enjoy it a lot, but, um. I wanna be like one, one of them. You know, I, I wanna be like, you know, actual, actual peers, you know, the people that we, we work with.

And, and a lot of people come to us and I, I think we could get advice. We do awesome work, but it, it's different when you also run a publication. I really wanted that. Um, so

Chenell Basilio: that's exactly why I stopped doing service work and went and built my own thing. 'cause I was like, well, that was fun, but also like, you see how well you can grow somebody else's thing and it's like, can I just [00:09:00] do that for myself?

Like, see what happens. Yeah.

Nathan May: Yeah. So I'm always, I'm always on the lookout. I mean, I, that, that was definitely opportunistic. Like, I wasn't like seeking, you know, actively. Um, but I, I think like, yeah, I, I think in the next, like, whatever, two to five years, like I would, um, I would try to buy something. Yeah. So you have not yet bought

Dylan Redekop: a newsletter or you just tried to acquire?

Nathan May: Uh, yeah, I haven't bought a newsletter. I think the, uh, I think for a while. So I think people, if you're gonna buy a newsletter like. You wanna be really careful about it. It's very easy to buy like a list. So, so like the neuron did that, the neuron bought like lists, like ba basically lots of AI founders started newsletters.

And we can get into this, like I, a lot of people do this wrong. They start newsletters and they didn't have the monetization figured out and they get stuck to this, or addicted to this like drug, oh, my subscriber account is going up, or my cost per lead is super low. And they're not thinking about the actual like, outcome.

They're getting distracted by the pretty pink chart, you know, and beehive or whatever the, the ESP is. Um, and, and I think it's important to like, just be honest with yourself, like you don't have a business until [00:10:00] you actually are monetizing. So a lot of these folks never monetized and then newsletters like the neuron buy them up for less than a dollar per subscriber.

Chenell Basilio: Hmm.

Nathan May: Um, and you know, frankly, a lot of those lists, you know, are not super high quality. Is something that we, we found. And so I think it's very important to buy a list that is making, like ebitda, like actually makes profit or, or if you already have a big newsletter, there's arbitrage, right? So, so like, they actually made out quite well on those lists.

'cause they, the important thing actually, if you're gonna buy a newsletter, if you haven't started one, it's like the most valuable thing is actually the sales relationship. If you're selling ads, it's very hard to like, build a relationship with HubSpot or some of the companies that are buying ads in the neuron.

That, that's actually the real value of, of the deal. I wouldn't buy a newsletter that did not have that.

Chenell Basilio: Yeah, that's super interesting. Um, it's definitely easy to build, just like a list that doesn't have any quality behind it and then sell it and hope for the best. But I think you're right. Like if people can look past just the number, it's like, that's the whole game, right?

People

Nathan May: get distracted. Mm-hmm. I think by, you know, like there's a, uh, I, I [00:11:00] think we had a million dollars in ar. When I had maybe, uh, maybe, maybe a thousand, maybe 1500 people on the list. I had no following on LinkedIn. And, and, and there's other examples, like I'm not the only one. Like there's Alex Schey always cites this.

Um, there's this woman on Instagram who she does over a million dollars a year. She has 9,000 followers on, on her Instagram, and I think she's got some email, a late email list and a lot of other stuff. The reason her thing works is she, she'll get like a hundred views, 200 views on her Instagram reels, but her niche is like, she like works at a hospital system and she is extremely dialed in, um, on the billing between the hospital and the insurance companies, which I, I don't know a lot about healthcare, but like, it's barely, it's this huge battle and sos like the hospital that does work.

And then they have, they collect from the insurance company and the insurance company is like, oh, you didn't do this code, or, oh, we're gonna pay, you know, there's all, there's all this mess. 'cause they want, you know, they, they want the money for, for themselves. Uh, and so her thing is like, yeah. I have lived in how to navigate that and like [00:12:00] actually get the money that you should have.

And so that's worth a lot, a tremendous amount to the right type of person. And so I'm a big fan of like, that's Consum, maybe that's B two, B 10 use list. But I'm a big fan of like small but mighty lists. There are lots of lists that are five 10. You know, when we did the Jess Ji launch, I mean that that did a quarter of million dollars on 15,000 people.

Like small, but my lists are our real thing.

Dylan Redekop: Did

Nathan May: you

Dylan Redekop: say you're running a 1 million a RR with a thousand person list?

Nathan May: Yeah. So we went from zero to go. Yeah, yeah, yeah. It was cool. So, so we went from zero to a million ar in about, uh, 10 and a half months. Little close to 11 months, uh, last year. So we hit it in, uh, I don't know, November or December of 2024.

Um, and basically I had a bunch of stuff I had to figure out, wanna enter this market. 'cause like, uh, everybody else who does newsletter ads, like they either came from the industry or they had like a huge following. Um, and so I was like, like, what do, what do I do? Like, how do I, like, that's a lot [00:13:00] to, to go up against.

Um, and so I think two or three things worked really well. One 'em, one was this newsletter. I didn't know it was gonna be a good idea, but no, I think it's a very good idea. So I, I think like any founder, if you run a B2B company, so you sell, you sell a service, right? That could be an agency, that could be, you could be a lawyer, you could be, you know, whatever you, mortgage guy, any, any kind of like service.

Or B2B SaaS. Um, I think you are being financially irresponsible if you do not have a newsletter. And so what I did, which I didn't know before, is I thought, alright, um, I wanna do a newsletter and well, who, who do I really need to work with? Like, uh, at, at each of these newsletter companies, there are maybe like two people.

You know what I need? I need like the CEO or the founder and I need the, the head of growth or, or the VP of marketing. That's it. And so like, if maybe there's like 300 newsletter companies that I wanna work. Oh, so, so 300 times two, 600. Okay. Can I get 600 people that, that's like an Excel list. Like I can go one by one by one.

I can meet those people at conferences, I can email them, I can LinkedIn message them. Like it, it takes this [00:14:00] giant like nebulous world. It's like, oh my God. Like how do I, do I run ads? Do I call the email? Like, there's all these people I could reach. I was like, no, no, no, no, no, no, no, no. You just need the 600.

Can you just get 200? Of the 600 I, I can do that. Um, and so that's what I, I started doing and I basically, I would go and I think this also is important. I, I made it, uh, a private newsletter, so, so you had to be, uh, it's kind of cute. You, you had to be like, like invited, you know, like invite you to the newsletter and, um.

I would LinkedIn message people, uh, and I have a bunch of screenshots at this and stuff. Like for instance, I, I'm I LinkedIn messaged Sean Griffey, uh, who, who was the, one of the three co-founders of Industry Dive, you know, big, big deal, big guy. And, um, I just go, Hey, you know, I, you know, evening Sean, like, I run a private newsletter for newsletter operators who are doing 79 figures.

You know, it's generally for CEOs and their heads of growth. A couple people like X and Y and Z Read X and Y and Z were mutual connections that we had. Or a lot of times I'll do, um, competitors of the person that I'm messaging. So it's like, oh, they see their peers are reading this newsletter. Okay, [00:15:00] now I've now elevated the status of the newsletter.

Would you mind if I add you. I, I manually add them. They give me their email and then I, I don't put them, give them some landing page where it's like, oh, here you go, do it. Right? Mm-hmm. White glove. I do it for them and I add them. Yeah. That's been a great tactic.

Chenell Basilio: Well, and then when you send out the newsletter, you actually at the top say, welcome to blah, blah, blah.

And like there's four or five really big names that have joined in the last week, and it just like solidifies the reason I'm reading this newsletter. I'm like, oh yeah, so is Tyler Dank and you know, Nathan Barry or whoever reading this newsletter. And I think that's such a smart move too.

Nathan May: I, uh, I, I feel, I think I stole that from something I can't remember.

Uh, but I, I like that part as well. And a lot of people email, uh, about that. And, and like for somebody who's like listening to this, like, I don't have like, uh, my newsletter is like super ugly. Like there's no, there's no design. It's like, it's literally just like an email from me. Like, but, but I think that's by, I think that's an I that's a good thing.

Like, [00:16:00] like, like if you like, sell like a high ticket or like healthy product or service, like people wanna hear from you. And I, I think the mistake, so if you were gonna go do this, I think everybody who has an existing company should go do this. Because, because No, nobody does it, by the way. So I actually, so this is important to know, okay.

Why is this better than like, cold mailing people? Well, well, number one, Sean Grey's not gonna get on a sales call with me. Like, so that's not, Sean doesn't know me. It's like, who's Nathan? I don't, I don't care about this. Right. So the barrier to entry for a newsletter. Significantly for people who do get on sales calls with me.

Typically, if you're a B2B business owner, you have like, alright, you get on a call with somebody, let's say they don't close, you know, you, you're not gonna have a chance to get on another call with that person for maybe another quarter. So, so, so maybe there's like four times per year you could potentially close somebody Right?

For, for your product or your service. Um, so newsletter, right? And then, so you have this huge list now and, and then if I wanna reach out to people, I have to individually reach out to all them. Well, so a newsletter kind of solves all that, right? Like the, the friction is extremely low. Anybody would join and now I'm building trust and I, every time I hit publish, [00:17:00] I have a chance to potentially get on a sales call with somebody and I write one thing and it reaches every single person that I would potentially want to work with.

That's like, I think why it's so valuable.

Chenell Basilio: Well, and the content is like case studies of what you've done or like these badass stories from people you're working with, and so you're like, you're showcasing your clients, which is amazing. I'm sure they love that. You're also showcasing the value you provide and like what you can do, and then you're just kind of putting it all together in a newsletter and delivering it nicely to them.

Nathan May: Yeah, I wouldn't, um. I wouldn't delegate it. Like, like I got on a call with, uh, do you know Eric Sue at all? Yeah. He, he, he runs like a big SEO agency called it Single Grain. And he, he's, um, he's really good friends with, uh, he's been around forever.

Chenell Basilio: Yeah,

Nathan May: they they've been around. Yeah. They're they've been around for a long time.

They're, they're, they're cool. Like, they're like, buddy buddy. They, they live near each other in, in la They're, they're like an cool, uh, like agency owner, uh, pair e Eric's doing this for his company. And I think the mistake that Eric is making, um, is like he's delegating it to like his content team. I think that's the worst thing that you can, you can do.

[00:18:00] And there's no disrespect to anybody's content team. Like the, the, the leverage in the newsletter is that like it comes from you, like the founder and it's your words and somebody who replies the reply to you, not like a member of your. Content team? Um, I think so. I think that's the other important thing.

Like that is not a part of the business that I would ever delegate. I don't recommend anybody that. And so

Chenell Basilio: with the, because you have more than 600 subscribers now, so you've opened it up a little bit in terms of that initial list.

Nathan May: Yeah. So then, so the stuff that I'm have to figure out now is like, um, so we opened up a little bit.

So like for instance, like, uh, Brad, uh, Wilton, who, who used to lead content at the Hustle, like did like a writeup on us. And so we like opened up, you know, for that. And so a couple a hundred people came from that or, uh, we, we do other small things like that. Like we, uh, you and I, you and I did that summit with, with Beehive.

Mm-hmm. And we opened up, I opened it to the newsletter up to people who attended that summit. Uh, it is becoming more. Um, so this was a double edged sword, uh, in, in my business, which is like, uh, we, so we did a very good [00:19:00] job of like, I, I hope, I don't know, of building rapport and like, let me just give a bunch of information.

Like, like, like, uh, stuff that I think other people would charge for. We just gave away free. Uh, and I think that's very important to do and we did that in all the content we write is for people who are already doing 6, 7, 8, 9 figures. I do not write, um, beginner level, level content, and that's good for agency issue is, uh.

Well, we've not really built any like distribution audience with like somebody who is just starting their newsletter trying to get their first a hundred subscribers or trying to get their first a hundred thousand dollars with their newsletter. We've done a very bad job of that. And I had this buddy, this buddy Rowan, who runs the Rundown tell me that we went, uh, we uh, all went out with this guy Walter together to SF like last October.

And Rowan was like, dude, what are you doing? Like, you need to be like writing content on, on LinkedIn. Like this is the whole thing. Like you gotta do this, this, and this. I was like, I'm I'm, I'm gonna do it. I'm gonna do it. Um, and so that's what I've been trying to do more of. Um, you know, the what not like acquiring the neuron meant is like now I have to like figure out.

New ways to grow the, the [00:20:00] business. Certainly the agency will continue to grow, but like, uh, I want to start to stack other things on. So like, uh, part of doing that I think like requires that we, I hope like really cool stuff that like, if you're just starting your newsletter will be really useful.

Chenell Basilio: Doesn't that dilute the cool, like the coolness and like exclusivity of like being on your private newsletter?

Nathan May: Yeah. So, um, it's still like decently hard to get on it. Like, uh, like we did a, we got a feature with, uh, creator Spotlight, like BIS newsletter. Open up for that and I'm, uh, I'm gonna probably later today, like clo close it up again. I think what I gotta figure out is, so right now everybody gets at the same content.

Um, I actually think that's not gonna be the case in like a month or two. I think like advanced people will get my private newsletters and then everybody else will get like more kind of like regular business as usual content. But I, I, I do have to solve for that. And this is kind of like me like. Uh, like, I'll figure this shit out.

I don't know. Yeah. I'm, I'm looking at what other people do and like, um, and stuff and try to figure that out. Uh, but yeah,

Chenell Basilio: I still think it's such like a, a valuable way [00:21:00] for anyone getting started who wants to like, build a service business or even just like a small niche business to like start that way.

I think it's such a smart move.

Nathan May: I think it's the easiest thing to do. Like, and, and I, you know, if you are like a creator or you wanna start a newsletter and get to, let's say just, you know, 10 KA month even, I think ads can help. But I, I think there's this whole like, I think it's wrong. Uh, it's very hard to build a big business just selling ads.

'cause you, you really to like be interesting to, so, so there's two ways to do it, right? Like you can, you could go, um, over some the flight a little bit right now. Like you could go and you could have ads sold for you for, for like the bi ad network. And I, I think Kit does some of that stuff too, right?

There's basically networks now where like, you can have HubSpot or Nike, whoever as a sponsor and you don't have to worry about, you don't have to hop on sales call. It's just like done for you. The problem with that. Is that if you sell your own inventory, you might get, you know, a 20 to $40 CPM depending on your, on your niche, on on average.

And there's plenty of newsletters that break that rule. But, um, well that's good. 'cause that [00:22:00] means like, so $30 CPM is basically every single time somebody opens, you make one, 1000th of that. Or, or, uh, 3 cents. Right? So, you know, you can see a path where like, oh, I get 10,000 people, you know, 5,000 open, you know, whatever.

A newsletter where I think the math is like, if you have a 20 or 30,000 person newsletter and you have a healthy open rate, you know, you can get to like five to 10 KA month. But like the, if you do the networks, your CPMs on a $30, your CPM is like $5. And so that's like interesting, like you can generate revenue, but if you wanna do something where the newsletter is now a business, right?

It replaces your full-time income, you need to go direct sold. Which means you need to like get to a certain size. And so I think it is far easier to do ads and something else. So you had, you had cj uh, on, uh, I, I, I was messaging a good one, CJ, about this. Good. And at the, at the very end of the podcast, he was like, uh, he mentioned the media mullet.

I was like, ah, yes. Uh, amazing. I'm, I'm, I'm getting it out there. Uh, so I think everybody should have a media mullet and, and a media mullet is basically, I think it's, I think [00:23:00] it's good to say things that people can visualize. It's kind of silly. Yeah. But you should have ad supported newsletter in the front back here, you know?

Right. Right here. And then what you want is you want party in the back. You want party of high LTV products that sit in the back. So if you look at every big newsletter business, the bi ones who really succeed are doing this. The Hustle had ad supported newsletter in the front. They had trends, $300 per person community in the back that had something like 15 to 20,000 paying users.

It was something like a five to $7 million a RR business. It's, I think Sam has said that like maybe three or four people. We're staffed on that business, right? So, so sure maybe that was comparable to the size of the hustle ad sales, but when you actually look at the profit trends versus the newsletter business to be, I think they had like five or six salespeople and like five growth people and it, so writers, they're paying a hundred, you know, $150,000 a year.

My guess is the newsletter business was probably like a 20% margin and that's 'cause they were in growth mode. So I don't wanna, like, you know, plenty of newsletter business have 30, 40% margins. I think the. SaaS or the, [00:24:00] the community business. I think that was like a, a 90% margin business if I, if I had to guess.

And so it's very important to have that Block works. Jason Janowitz, right? That's, uh, newsletters and podcasts in the front, but then they've got events, they've got an agency business, basically like a consulting business for crypto. They've got, um, uh, like an enterprise like data platform that sits behind there, right?

So all, all these kind of businesses, the Van Trump report, right? This is a guy who makes $20 million a year with like two employees. They do subscription content on agriculture. Like, so, so like you, you want something high TV in the back. And so, like even if you are a creator who has, you know, 5,000 followers, think about like what skills do you have that you could teach somebody?

Because 5,000 people on your list, you know if, if you're niched down enough, like can you get like one person, two people to pay you just $250 a month to start for your time? Like can you sell your time in some way? And I think that is probably the most valuable thing you can do. 'cause you don't necessarily need to go to the agency route after that.

Actually selling your time to five 10 people. Now you [00:25:00] intimately understand your newsletter subscriber. When you want to launch a digital product, like a course, an accelerator, whatever, whatever you wanna do afterward, you're getting paid to do your own customer research. And so I think that's one of the best places to To start.

Chenell Basilio: Yeah. And your word also like glossing over the fact that Yes, Sam Par and the Hustle, they had like that huge sponsorship business and then trends on the back end was even if it was just like the same income, like bringing in the same amount of revenue, the people that were in trends are now like dying for him to restart that because it was such a good product and they loved being part of it.

And like I see it all the time, like randomly logging into my Facebook account, I'm like, people are trying to get trends back going and like talking to people. I mean like how do we get this started again? And it's just like he built such a raving fan base around the back end of that. And you don't get that just by selling sponsorships.

So I think there's that too.

Nathan May: I was talking to, uh, Justin Gordon, the, uh, uh, that guy, we did a, a run together in New York like two months ago. Uh, he, he smoked me. I dunno if you, he's like, [00:26:00] he's crazy fast runner, by the way. He's so fast.

Chenell Basilio: I see him on STR all the time and I'm like, I am never running with you because I will die.

Nathan May: He's, he's crazy. I, I've run with a couple people. Uh, I, I try to do that. Like, oh, if I, if I'm gonna meet somebody, like, oh, let, let's like also go on on a run that's like kind of fun. Uh, he was the only one where like, and, and not, it wasn't even close like by, by a long shot. Like, I had to be like, Hey man, uh, could we like walk, uh, for a little bit?

Like, is that, is it chill? Is that all right? Uh, he really fast. Um, but he, he's got a big community of founders like, dude, you should, like we're talking about, maybe you should just like, restart trends. And it's, it's wild by the way. Like, uh, I don't think people, I, I was never in trends, so I never got to see the inside.

But I've seen like the outcomes of that like, um. Cody Sanchez mm-hmm. Who now like, you know, does over $10 million a year with her business. Like, she started in trends, basically. Like there's all these like juggernaut people who, when you look back, they, they were in trends and that, that's, that's pretty cool.

Chenell Basilio: Yeah. That is pretty cool. Um, I think [00:27:00] there's something about building that community on the back end. It's just like, it goes with you no matter if you sell your business or what. Like people are still wanting that back, so,

Nathan May: yeah. Yeah. You wanna be, uh, you wanna be known. Well, not, not well known. I think that's important.

Chenell Basilio: Well, cool. So I know you have this whole thing about like, the four types of people who should start newsletters. Do you wanna share that? Mm-hmm. You mentioned that in your little list that you sent over, so I'd love to hear what you think about that.

Dylan Redekop: Yeah, yeah. Your, how do I choose frameworks? Were, were interesting.

I'm, I'm curious to learn about those.

Nathan May: I wanna know what you guys think too. Like, I, so. We, so we just did this, uh, accelerator with, uh, beehive and, and the way, the way we did it. So we had, uh, we, we had, uh, 250, 300 people join. And basically a hundred of those were team members of like the biggest, uh, newsletter companies I invited from my newsletter.

So we had like the hustle, we had New York Times, we had Morning Brew, we had the gist, we had superhuman, we had like all the, all the, all the big folks. And then we had 200 spots that were, um, either people who went to the summit or who, uh, just like raffled. Um, and, and um, that was cool 'cause it was the first time I [00:28:00] spent a, uh, in a long time I've spent like a significant amount of time around people who were like trying to get their first 1000 or, or, or get to their first a hundred thousand dollars.

And yeah, I think, uh, a, a couple of my learnings from that, I, I think there are like, yeah, three or four types of people for whom a newsletter tends to work the best. There's so many cases where somebody can succeed, but I'm just saying like on, on average, like the most likely to succeed are are four. So one I think is, um.

Create, any creator should have a newsletter. Like if you're trying to build an audience on X or LinkedIn or YouTube or whatever, trying to figure out ways to pull down that audience to your newsletter is one of the most important things that you can, you can do the, the number one channel for Alex Hermo for like the revenue that he makes.

It's not like reels or YouTube or any of that. It's, it's, it's his, it's his email list. Um, 100%. And like, he's, he's a big steward of like building that out. Um, the second group, I think, I don't know this group as well. But our, our journalists, so, so, and we, we've all kind of seen this, right? Like there's a, like, there's a lot of distrust in [00:29:00] like, traditional media houses.

Mm-hmm. So a lot of journalists, um, we just started working with this guy, Oliver Darcy, who used to be like a big time journalist at CNN, uh, in, in Broke Away. And Loren a, an incredible news letter called Status. And like, it's just crazy to see like how people love his content, like how sticky that is with people.

And so, so yeah, I think if you're like a, a well-known like writer, like do your own thing as like a move right now. I think the third is, uh, business owners. Every founder in B2B should have a newsletter. And I think the fourth is like. If, if you're like newsletter, curious, I think there's a, a much more predictable path of how you avoid the like, oh, I got to five or 10,000 subscribers over three years, or, or, or got there with ads and spent a bunch of my money, but I never got that money back.

Like, so how do you avoid those situations? 'cause that's actually what happens to like seven or 80% of those people. And I think it's version of that, the bucket of those people who are thoughtful trying to monetize as quickly as possible. It's like, if I was gonna start, you know, a new newsletter, I would like a budget, uh, [00:30:00] 'cause I'm, I'm, I'm trying to pay with my dollars instead of my time.

Right. You, you'll pay for your subscribers one way or the other. You'll pay with them with your time. You'll pay with them, with, with your dollars. I would set a three to six month timeline where like, all right, I'm gonna, whatever, spend $15,000, that's my budget for this newsletter initiative. And I'm gonna try to, as quickly as possible, get a couple sponsors and sell some kind of like product or service.

Like that's the people who do that I think are the ones who do quite well. Uh, and that's like, Hey, I'm coming to this with like not a big audience. If, if you have an existing audience, even if it's five or 10,000 people and you are B2B, or able to monetize that at a B2B level. So for instance, like there are, you know, people who sell, for instance, like fitness coaching or, or like, uh, you know, other types of transformation around jobs, investments, life transformations like losing weight or like looking better, dating better, where you can sell things that are a thousand dollars or more.

That can completely work with a small audience or even no audience. Uh, sometimes, but, but if you're not in those [00:31:00] categories, right, like then you, you either need to, like, you, you need to have a big audience if you're trying to grow or organically, um, you know, like I, I, I think the, I I looked at a bunch of creators that Justin Welsh and Dick Bush and all these folks, and like, I think the average is like, people convert 10 to 20%, you know, their audience down to the newsletter.

And, you know, I, I love this. Um, you, you put together this graphic that was like all the people you studied, like what was the average time it took them to get to like 50,000 subscribers? And it was something like, was it like a year and a half, two years, something like that?

Chenell Basilio: Yeah, I mean it's, it's gotten so much faster over the last couple years.

I was just looking at this the other day. Um, if you started back in like 2014, it took like eight years on average and now it's like 24 months. Is like the average to 50 K, uh, which is just wild because now you have things like recommendations. People are getting more savvy with paid ads for newsletters.

Um, there's just all kinds of like boosts you can use and refine and all those things. Mm-hmm. So if you really wanna grow that number, it's totally possible these days. Uh, and it's just gotten so much faster. But my caveat with that [00:32:00] is like, if you're just starting and you don't know if your content resonates or like who your audience is or, or, or that kind of thing, like I am a huge proponent of waiting until you have like at least a thousand subscribers, if not a few more, uh, until you start running paid ads.

'cause otherwise, who are you sending it to? Who's, what, what content are they getting? Are they gonna enjoy it? Because if you, if you burn that trust like early on, it's kind of hard to get them back later. So, um, yeah. But it's, it's a whole, whole can of worms, I think.

Dylan Redekop: And how you're gonna monetize too will play a big part.

Like if you don't know how you're gonna monetize this audience, then there's no point in sinking a bunch of time and money into it. The,

Nathan May: yeah, it's, it's the first question you should ask. It is like, it's the, I think, first question you should ask is not how I get the subscribers. It's like, how am I gonna monetize when I do have them?

And for most people it should be. Choose ads. And then one other thing from like products or services, digital products or, or services. Uh, services can be coaching and consulting, right? Not just like, uh, I I'm an agency, or I, I do your taxes, I'm an accountant, or something like that. Because that [00:33:00] needs to be the like, okay, cool, if I'm gonna monetize with the consulting, like I need to, I, I wanna be able to get one client by the time I have 1500 subscribers.

So that, now, now you have like a, like a goal that like actually mm-hmm. A goal that translates into, uh, revenue getting to 1500 subscribers not automatically translate into revenue, right? Getting the first consulting client or getting the first ad sponsors what translates into revenue.

Chenell Basilio: Okay. So you have four types of people who should start a newsletter.

Who do you think should not start a newsletter?

Nathan May: Um, so if you are impatient, you need to be in one of those four buckets. And you need to, like, you need to create a sandbox that's like, how do I find out in three to six months if this will work? That the answer could be no, that this particular idea doesn't work.

My sale at Milk Road was like, it was an okay amount of money, but it wasn't giant amount of money. And, and like me doing the case studies for the, the feed and, you know, we got some subscription revenue, but it was like a couple thousand dollars a month. It was, it was not meaningful. And so like, oh, I, I was like, oh, why don't I just turn that in an agency and, and I'm writing all these people with personal brands and newsletters.

Why don't I just go work with those people [00:34:00] actually instead and charge 4,000 or $5,000 a month instead of, you know, charging a regular person, you know, $10 a month. You, you need to set that, that sandbox, even if the answer is no. 'cause if the answer's no, that's okay. It just means you now have. You could go choose another idea and you haven't not, you've not wasted too much of the most viable thing, which is your time.

The worst mistake you can do is spend two years on an idea that you should have spent six months on. So I think that's, that's the thing. If you're impatient, if you are very patient. You know, the game that you wanna play, for instance, um, you know, if you are, there's an awesome guy who was on our first cohort who is doing crazy well with a relatively small newsletter called The Secret CFO.

And he, he writes, he's like a CFO at a really big company and he's totally anonymous. He makes a killing on his newsletter. It's only like 40 or 50,000 people he's in. He's like CFOI my life. Is CFO I'm committed to this niche. I'm never changing anything. Then you get to be more patient, right? Because like you've, you know, your game.

Um, but mo [00:35:00] most people don't know the game they wanna play. Right? It you like you're just tasting from the, the tasting menu of the universe. Right? And, and that's okay. You don't wanna, like, you know, if, if you, uh, what's a good example? Like if, if you, if you go down to like the East Village in New York City and there's so many amazing restaurants like you, you don't wanna just go back to the same old ramen shop.

Like there's amazing sushi place nearby and something else, like you, you, you wanna get an answer and then you wanna move on. Maybe the better example is like a bar crawl, right? You, you wanna actually move and, and taste a bunch of the different cocktails or validate that this is my favorite bar of all time.

This is what I'm gonna stay at. Like, you mm-hmm. You, you wanna be careful with it. I dunno, did I answer your question? I'm not sure if I did.

Chenell Basilio: No, it makes sense. And I would've said the same thing. Yeah. Like if you don't Yeah. If you're not in this for the right reasons, or you're not gonna stick with it more than six months, then just don't even start.

It's not worth it.

Nathan May: And, but, well, the thing I'll say is like the, I don't necessarily mean it as the right reasons, I think it is, um, and people can have their opinions, but like, I think it's totally okay to be an opportunist. Um, you know, like I, I have a, a buddy of mine, Josh, who's in, he's a Washington Square Park, a couple blocks south of here.

Like [00:36:00] right now, he's 23 years old. He makes $200,000 a month, um, 23 selling Wow. Street interview ads to DDC companies like Avi and Jones Road Beauty and like all these different companies. He's been doing this business for a year. He though the Wall Street Journal, actually today he just did a, a, uh, a Twitter post, actually literally ran, oh shit.

Josh, this is so cool. I, I, this, uh, I got notification this literally right before I hopped on this call. Uh, this is him. I dunno if you can see it. There's Josh. He's in Washington Zero Park right now. Oh. And, uh, the Wall Street Journal is about to, to go interview him for, for his business. Josh is like, Josh didn't like exit the womb, passionate about, you know, like street interview ads.

Like he, he was an opportunist and he found a really good niche and he burned the boats and he, he quit. He had a job at, uh, an internship at Blade. He quit that. He dropped outta colleges last semester and he went all in, slept on couches, and he built this business over the, the last year. That's okay. Like you can be an opportunist, um, but if you're gonna be an [00:37:00] opportunist, like you need to.

Ration your time and be smart about quitting stuff, uh, that isn't going to work. Um, I think that's, that's more about what, what I'm,

Chenell Basilio: yeah. Well, and I wouldn't even necessarily call that an opportunist. I would almost say like, he's an extra experimenter. Like he's trying a bunch of things. He is gonna test, like see what works, see what sticks with him.

And I'm sure over time he's gonna find something that he wants to stick with for more than five months or six months or whatever. And so I think that's actually a smart move, especially when you're young.

Nathan May: Yeah, you, you need to commit to being a, uh, like a, a founder. I think maybe that's, maybe that's the better, like rule, like, like, uh, what's the, I think Naval said this, but it's like startups fail, founders don't, it's like if you committed to the identity of I'm somebody who starts stuff, it's okay to try crypto newsletters and then try one that's in penny stocks, then do one that's for creators, like jump around, you know?

But like, uh, commit to like five years of like, I'm going to start things until something works otherwise, like, you know. Yeah. Yeah.

Dylan Redekop: We haven't talked at all about like really about paid subscriptions or paid newsletters. Is that, [00:38:00] is that a path, um, any of your clients go down or that you go down or have considered going down?

Or what's your overall kind of feeling on, on that monetization revenue stream?

Nathan May: Yeah. Um, I think paid newsletters are really hard. Um, really, really hard. So as part of trying to figure how much I can say about this, we've talked to a lot of the big newsletters that are paid and um, I think a lot of them. A lot of them have made organic work.

So there are two scenarios in which I've seen a paid newsletter work really well. You, um, you have a giant hyper fan audience, so this would be like if Rowan wanted to, uh, Rowan, who runs the rundown, he has 600,000, 700,000 followers. He interviews Mark Zuckerberg once a year, like it gets invited, all this AI shit in SF all the time.

He could start a paid newsletter because of his scale and because he's so well known, the, the journalist version of that is like Oliver Darcy at, at, uh, at CN nine who nine One Status or like, um, or which is a newsletter, publication, uh, or like, um, oh [00:39:00] gosh, what's the one? Uh, the, the Anchor, which it covers like the business of Hollywood reporters who, the journalists who write for that, they've been writing for that, like they're known in those industries.

That's why executives and people are willing to pay for that content. The other scenario. Is you, you gotta break the news. You, you gotta be someone, or, or your analysis is so darn thoughtful that this is the only place people can get it. Um, and so like a great example of that, you know, might be like a, I would say like a, like a right with AI by, by Nicholas Cole.

Like it really thoughtful, like how do you actually use AI to like, you know, make more money in your business or, you know, prompts that will like, help you out. But it, I think it's hard to do it. And, and when I say breaking news, actually, so this is, uh, maybe I should tweak what I said. People who like break stories.

Um, so like, uh, Oliver actually maybe is an example of both. Like, he broke, I think a lot of the stuff, like I think RFK had some like affair, you know, [00:40:00] with some, some person, and that was a huge breaking headline. Oliver was the one to break that. And then like the New York Times and everybody else picked that up from Oliver, he gets the scoops.

So if you're first right, you, you have to be first or you have to be best. Mm-hmm. And ideally you have a large audience that is when subscription works. The cases where I've seen it work at a smaller scale, like a hundred to $200,000 a year would be like, there's this guy, I can't remember his name. Uh, he, he's, uh, we, we cover him in the, in the accelerator, but, uh, he, he gets into like Lego investing and teaches you all about like how to invest in Legos and he, he makes like $150,000 a year.

In, in, in that space. So it's like the things I said plus like, okay, how do you map all these things to a framework? There's generally four things people are doing. They were doing some type of life transformation, so like lose a bunch of weight or something like that. They're doing some type of investing thing.

So it's like Market Beat has like a big paid subscription. They do $40 million a year, probably five of that is, um, through their subscription. They're like investing in stocks, all that shit. There is, um, uh, oh my gosh. [00:41:00] What, what are some of the other ones? There's jobs. So like, become better at my job status is subscribed to a lot of people in the media industry.

'cause having that breaking news is actually really impactful for strategy and like what other people would go and write about. So people pay for that. And then the last one, oh, niche hobbies, which is like the Lego thing.

Dylan Redekop: What about entertainment? Is there a place for entertainment in a paid newsletter?

Have you seen that work anywhere? I

Nathan May: bet it's hard. Yeah, that's my, that's my assumption. I think it's hard. I think it's like, uh, entertainment like. Media, like business I think would work, but just like, unless you were breaking crazy stories and doing like investigative stuff, you know, like, you know, uh, Taylor Swift, you know, I don't, I don't know, is is it gonna break up with whoever that big chunky football Travis Travis Yeah.

That she dates Travis Kelly. Exactly, exactly. I was getting my second guess after big chunky football guy. Yeah. Uh uh um, I think that would work. But like, uh, I don't think like People Magazine could do like a paid subscription in a good way. I mean, maybe they get a hundred thousand people 'cause they've got whatever, a hundred million who like Visit People magazine, but it's not [00:42:00] gonna be like a, a needle.

Chenell Basilio: And so when you say it's not, it's not gonna work. You just mean it's not gonna get to a scale where it's like large enough to. Maybe you run paid ads on a regular basis or that kind of thing?

Nathan May: Yeah, yeah. It's really, it's really hard. Most of the people who scale, uh, paid subscriptions scale it organically.

Chenell Basilio: Mm-hmm.

Nathan May: Um, now I think paid is very tough. Some people are making paid work. Uh, but it's, you gotta play the long game. It's like you, you require a subscriber for about as much as you make on that subscriber in the first year. And so where you start to actually make money is like. Year two, year three.

That's a long game. Yeah, right. That's, that's a long game to play. What do you, what do you guys think, I mean, are have you seen like killer subscription newsletters work? I mean, I think the big audience thing, like Lenny Chesky has done this very well. St. Straty has done this very well. There, there's examples,

Chenell Basilio: but does Ben Thompson of Straty even run paid ads or does No,

Nathan May: not paid ads.

So that's, that's the organic thing. Yeah.

Chenell Basilio: Yeah,

Nathan May: yeah.

Chenell Basilio: Totally. Yeah. Yeah. Yeah. Especially with like, a lot of the paid subscriptions and paid newsletters are on Substack and you don't get many good analytics, so it's really hard to say [00:43:00] like, is this working? Is this not working? Did they actually come from a paid ad?

Did they not?

Nathan May: Yeah. Mm-hmm. We're trying it by the way, so, so, so like, um. You know, we have, uh, I think we've done a good job of like, we've, we've done it multiple times now where like there were multiple ad monetized newsletters that we have scaled to above a hundred thousand dollars a month in spend profitably.

Then we went to like affiliate and we worked with this, uh, big affiliate company called Rev Ventures. They own a newsletter called The Points Guide. They've never worked with an outside agency and they were very skeptical. We have skilled them, you know, they, they spend now in the top five of newsletters per month.

Um, and so, uh, you know, we'll see where, where I wanna go next is like, oh, can we go solve subscription? And also like niche B2B, like where you wanna get executives and like really qualified people on the list. Um, so that's kind of what we're doing. We're working with like five or six pretty heavy hitter subscription newsletters.

Right now, but, but we've just gotten started like in the last, like two or three weeks. So I'm kind of like, I'm giving a bunch of problems, but I try to solve it and, and see what we can do.

Chenell Basilio: If someone were starting a [00:44:00] B2B newsletter today, what do you think like the biggest opportunity that is, like not well known is

Nathan May: tools.

I, I, I'm sure there's more than that. And, uh. Exactly. Yeah, exactly. Nobody's writing about hammers. Yeah. Um, maybe, uh, I think it's like, um, so actually I'll say two important things. So industry dive, um, again, a hundred million dollar plus revenue company. A lot of the industries they entered, they were not first or the second or the third like newsletter to enter those industries.

What they cared more about was like, is this industry highly regulated so they care about news 'cause shit's like changing all the time or do people spend a lot of money? 'cause then, oh, advertisers spend a lot in order to get like a paying customer from our, our, uh, newsletters. Or do people meet at like trade shows and conferences?

'cause then we can go, oh no, we can go find our advertisers. We can go find our executive readers. Like all those are really critical ingredients in B2B. And B2B is, I think most newsletters are an execution game. You do not need to be first. Like the rundown is just, and, and this is no dispar to [00:45:00] row 'cause he's incredible operator and they write amazing content.

And Rowan is winning ai. I mean, no, nobody in my opinion, is close to Rowan, uh, in the AI space, but the rundown is like Morning Brew, but for ai. And so, so it's, it's like, it's an, it's an execution game. Uh, it's not like you don't have to be the only one doing something. Yeah. There's stuff that would be important in B2B.

Oh, shoot. There's something I wanted to say. I forgot it. Wait, what was it again, SHA I was just

Chenell Basilio: asking if there's like a good, uh,

Nathan May: like Oh, oh yeah. I've got it. I've got it. I got it. Okay. So, okay. Where I think people are not spending a ton of time are, are tools. So like, uh, like, uh, uh, so one of my buddies worked at Figma.

And when they went public, like three or four, uh, whatever weeks ago, I can't remember when it was. Um, he was sending us all these text messages. He all the, all the sales guys at FEMA were like trading techs. And it's like, so that IPO was huge. There are salespeople who made $1 million, $10 million. Like some of the top salespeople made like $15 [00:46:00] million in that.

IPO just, just like employees, right? 'cause they got stock, you know, five years ago in, in Figma. It's like a, I can't even remember, a $10 billion plus company or something like that. Why isn't there a newsletter? Maybe there is a newsletter that's like, we teach you everything. Figma, you know, like that's the best for like Figma, like pick whatever your giant tool is, you know, like that.

Mm. Um, you know, rep, rep or whatever. You know, it could be any of those things. I think being the barnacle, like on a giant tool like that would be really valuable.

Chenell Basilio: Yeah. 'cause then you could eventually maybe even sell to that company and then there you go. They already have the content and the distribution.

Mm-hmm. And everything. Mm-hmm.

Nathan May: Exactly. Exactly. You could do hiring, you know, for instance, so there's like a, there's a newsletter. I don't know if I'm supposed to say, although they do talk about, well they talk about publicly. Yeah. Yeah. So there's a newsletter called Fit Insider. And it's these two guys who sold a fitness like gym company.

And so they're really well known amongst like operators, uh, in that space. So they have a bunch of like high profile people who read their newsletter. You know, they, if you go look on their LinkedIn, like they're [00:47:00] doing hiring services because they have a bunch of cool fitness wellness, um, you know, operators on their, on their newsletter.

And so like now they've turned that into like a B2B service. Well like, oh hey, what is ER gonna have? It's probably gonna have a bunch of like cracked designers and like full stack engineers. Oh, okay, cool. If you take the best people on that, you could do high. Like there's a bunch of different optionalities you could do just by focusing on a, on a tool.

Um, because that tool is basically implies, right, you've got a bunch of designers. So yeah, I think there's cool stuff.

Dylan Redekop: There's a lot of people who do courses for tools. Um. How to learn with obsidian or notion or you know, stuff like that. Even Canva to some degree. But yeah, you don't, you're right. You don't really see a ton of, I guess, tool specific newsletters for that, that kinda market.

And that could always branch into kind of courses or memberships or communities. Yeah. It's important to know

Nathan May: your options, right? So the, so what is tools technically sit inside? It sits inside The second thing I mentioned, which was jobs help me do better at my job. Mm-hmm. That's like a category of newsletters you want to be in.

And so like, okay, well what's a real example of that? Miss Excel [00:48:00] makes millions of dollars. Yeah. Every year selling information on how you become like cracked at like VBA and like pivot tables and you know, VLOOKUP and index match in Excel. And like people pay for that. Oh, well what if you were really good at Excel, but like.

You wanted a pair tool with a niche? Well, there's a company called Wall Street Pep Prep that is uh, sold a bunch of courses on how do you become like an investment banker, get really good at modeling in a private equity context. And they were doing that to consumers Well then they sent, oh, well actually let me take scale plus niche and actually go from B2C to B2B.

So now if you go work at Goldman Sachs, the people who train you are not Goldman Sachs people. Wall Street prep comes in. Geez. And Goldman pays them to train you. So this, so it's, this is why it's important to understand the, the menu 'cause Okay. Jobs. Okay, jobs, tools. Do I go B2B? Do I go B2C? Do I go high ticket high?

Like, you wanna have this like, mapped out in your head so that you know all the places on the board that you can go with your newsletter. Wow.

Chenell Basilio: Brilliant. I love it. Yeah.

Nathan May: That

Chenell Basilio: is smart. This is awesome. Um, I know we're at the top of the hour, [00:49:00] so we can jump off here shortly if you have to run, but, awesome. I just was, I need It's

Nathan May: extra time.

I mean, are, are you guys busy? You got stuff going on?

Chenell Basilio: I don't,

Nathan May: oh, I don't, I don't know. I, I don't want, I don't wanna, I don't, I don't wanna trick you and like keep you captive. No,

Chenell Basilio: no, no, no. It's good. Um, so, okay, so wait, dig into this Figma idea a little bit more. So you're saying like, if you were building out like, I don't know, send out one awesome tip for Figma a week or something.

Like how, well, what do you even envision that looking like?

Nathan May: Yeah, so I think what I would do is probably, um, tutorials, guides on like how to do something really, really well in Figma. So, so as an example, um, there's a guy, there's a, so, okay, let's say how do you get the audience Probably the best place to get audience for fma, 'cause it's a visual thing, is to do reels on Instagram.

'cause that's discovery, right? Re reels sends you to new audiences with videos. So not posts, but reels or do that on TikTok. Well, you can show like doing an amazing, like. I don't know. Uh, let's, let's say you're doing it around like mobile app design and there's some like really cool like, you know, swivel or, or, or some really amazing like paywall [00:50:00] design that works really, really well.

And it's like, that's like really pretty or onboarding sequence. Okay, cool. People are in, that's like going really viral 'cause it's like beautiful and designers interested in that content. It's like, hey, um, if you want like this Figma template, I just made it for you. So you don't have to think about the hex codes.

You don't have to think of the animation. You don't have to think about like, all this stuff to think about. I have the template sign up to my newsletter. It's in the description. Or, or, or if you're on Instagram. 'cause you can use MEChA comment, the world word, you know, animation or Figma and I'll send it to you.

Email gate, the template. Now the person's on your Figma newsletter and you've sent them the template and now maybe your content is like sending templates. Maybe it's that plus like tips on it becoming a better. You know, designer, maybe that can extend beyond just like tactical, you know, Figma stuff. So I'm not a designer, so I don't know a ton about this, but for instance, like if you are, I'll give an example for, um, you know, for Excel, like, like I, I used to be a consultant at this company called, uh, BCG, like one, these like fancy, fancy strategy consulting places.

And like a big thing on our training for Excel is like, [00:51:00] yes, that's important to be good at Excel, but when you're building a model. It's actually really important to like map out on a whiteboard. What are the inputs for your model and like the data you needed to get to get, and how does that tie to like how you bubble up or predict revenue or the size of a market before you get into the model?

So I don't know, like, like that's an example of like it's actual qualitative thing, like a skill thing contributes to like your ability to be good technically. I'm sure there's some version of that in the design world. So you could start to like map that out. What are all the things the designer needs in their tool belt to be good beyond just the choose these colors, do this animation, think about this widget.

Dylan Redekop: It's like theory before, actual practical

Nathan May: skill to some degree. Yeah. Yeah. And, and, and people want both, right? So like, like, uh, on LinkedIn, you know, I'll do posts where I'm like, an example of what we are talking about right now, like this is like kind of meta, but like there's like doing things right and then there's choosing the right things to do.

So doing things right's like. I've perfected my welcome email and all this stuff, and all this stuff, but, oh wait, I'm, I'm in the wrong niche. I'm in a niche that's actually really hard to [00:52:00] monetize. That, that choosing the right thing to do actually first would be really, really important. So you want that kind of like, what's the framework?

And they also want really, like, tactical stuff. So like when I write, you know, we, we wrote a big case study on like the, the $200,000 launch with Jesse. And so I, I literally just showed people like, here are the emails that we wrote, did the revenue. You wanna have both of those things, tell people how to think and then tell people what to do, show people what to do.

I think those are all very important.

Chenell Basilio: No, I like this idea. This is brilliant. 'cause I was not expecting you to go down this path when it, when I was said like, what's the B2B play you would do? And you said tools. I was like, that's interesting. Tell me more. But yeah, it makes sense. I mean, it's kind of like, uh, what Miss Excel did just in a different, it's, I put niche down,

Nathan May: right?

I mean, you, you, uh, you know, I saw, I was talking about this on a different pod thing, but like, I, I was scrolling, um, Instagram like three months ago now, and I saw this, um, this like ad for like a, a paid ads agency that worked, dog e-commerce brands. I clicked through because I like to look at people's funnels, but on my head I [00:53:00] was like.

Dude, this is Ter who like this has gotta be the tiniest business. Like what a terrible idea. And then I go to LinkedIn and you can click the little insights thing on LinkedIn. It will tell you how many employees people have and like whether they're going up and whether they're going down. And it was like 25 employees like up into the right.

Uh, and I was like crazy. But that, that's so if you think you are not niched down enough, you're probably wrong. And it makes sense, right? 'cause like, okay, if you're a designer, like I'm sure there's a bunch of different design tools. Like you want the person who will give you Figma. If you're the e-commerce company and you have like a dog food brand, like do you want like somebody who just does all general like D two C or Facebook ads?

Or do you want the guy who like his whole life, all he thinks about, he wakes up every single day and all he thinks about is like, how do I get people to buy like wet dog food for like $30 a month? You know what I mean? Like, you want that guy, you know? Yeah. That's why people pay Josh $200,000 a month.

Like Josh doesn't do podcast ads and you know, static graphics, all this thing. Like he wakes up. He stands out in the 80 degree heat. And when it's the, [00:54:00] the, the, uh, the winter, he flies to Miami or LA and does it, or he goes underground to the subways and he does the ads. Like that's the guy for, uh, uh, street interview ads.

Like you, you wanna be that. That's, that's what you wanna be.

Chenell Basilio: Yeah. Wow.

Nathan May: Wow. That's epic.

Chenell Basilio: I like it. I like it. Yeah. Um, now you're making me wanna start a Figma newsletter. If anybody's good at Figma, reach out. You can write it. I'll help you grow it. Let's go.

Nathan May: It's good. You know, you should, you should take like, uh.

Percentages. I know, right? Have you guys thought about, like, how do you guys think about growing your businesses, um, and the podcast? How do you guys think about that?

Chenell Basilio: Great question. I don't know. Uh, the podcast, TBD right now is just fun. It's fun to have conversations and like it turns into other things.

And like getting to know people like you and CJ and, you know, Caitlyn Burgo more so it's just a, mm-hmm. A good time to, uh, create more content. I think people really enjoy the podcast just because they get to see you and hear how you think. And, um, [00:55:00] it's almost like your new, it's a newsletter dimension.

Totally. Yeah. It's like your newsletter where you like writing these case studies, but you're just like talking to people and it's just like more of a trust builder. I don't know. I don't see it getting huge, but I think it's just like a fun, like consistent. Ongoing play to have. So,

Nathan May: oh, and that's the right way to think about it, right?

It's like I, uh, like, so we, I, I launched a podcast with would be mm-hmm. Uh, personal, IPO and like, the smartest thing for me to do actually probably in the short term would've been to like, do like a newsletter, podcast, say, actually doesn't, like you're saying like small, like it's a bad thing, but, but actually like, you're small because like if somebody, you are so hyper specific to the right person.

Like if somebody, anyone who has a newsletter should like listen to this podcast. Right. You actually wanna be there. My thought process with like personal IPO was like, I want, like, I may wanna do newsletters and other stuff, like are there are other things I could build onto the business in the long term that I don't even know, I don't even know there are unknown unknowns.

Mm-hmm. I don't even know to think about them. Well, I should have one thing that I do that is broader. And it's Tam and so personal, IPO. It's still specific 'cause it's like we [00:56:00] talked to founders like Sam Par, Dick Bush, Justin Walsh, these people who, it's basically the, the feed, like the original newsletter, but like a podcast who have built like incredible businesses and have a personal brand, but it's much broader than just the newsletter stuff.

Uh, 'cause I, I don't, I don't know what I'll do in like 10, 10 years, but I, but I think it's good to like, have some type of asset that I've built that is like that and that should be working on that now. Um, that, that, that's what I think.

Chenell Basilio: No, I think it's a good one. I listened to the Sam Par episode. It was good.

I enjoyed it.

Nathan May: Yeah, he's fun. He's, uh, he's kind of like, uh, he's so many good stories. Like, I don't know, it was kinda just like winding up like a doll and you, you just like let him go. Totally. You just kind of like, I don't even need to be here. You know, like I'm, I just say some words like, every once in a while they just pop,

Chenell Basilio: pop.

It's most entertaining doll's. So good. Yeah.

Nathan May: Yeah. It's crazy. I mean, it, it was one like, he's so, he's so good. Like, like we've talked to other guests and all the guests have been awesome, but like when I was with him then it was kind of like. Man, like I, you could just, you [00:57:00] could talk for five hours. Like you just, there's, you're, so I think Sean Perry calls it generative, like somebody who can just take one thing and build on it like 10 different ways.

He's like, uh, he's the most generative person that I've ever spent time with. It's, it's, it's insane.

Dylan Redekop: That's, I mean, that's why his podcast is what it is in part, right? Like, he's just very rarely will like, laugh out loud to a podcast. But when him and Sean start laughing and they're going off on tangents and it's just, it's, yeah, you can't help but help but chuckle.

And then that just keeps me hooked as a listener. So he's so real. Mm-hmm. You know,

Nathan May: which I think is hard to fi. Like, I, I always remember, I think this has happened, multiple episodes, but he's like, you know, he'll, he'll be talking about a guest. He's like, let him, what is it? What did the kids say? Like, let let him bake, let him bake.

And I was like, no, no, no, dog, dog. Come on. Let let him cook. Let him cook. And he's all these fun like. You know, like, I don't know, SAMMS, uh, yeah. It, it's cool. Like it makes me feel better 'cause, um, really their whole podcast is this way, is like, they, they have these uber successful people on, right? And it turns out, and we're, we're kind of doing this with [00:58:00] personal IPO, it, it turns out like, oh man, like, they make mistakes or like, they fucked up and this thing, or this thing isn't going well.

And it's, it's not that you wish for those things, but it's kinda like, oh, I, I feel like I fuck up all the time. Mm-hmm. So it's just to hear, oh, this person I think is, you know, up here. Like, they're just like me. Like, that's such a important thing. I'm a big fan of this phrase, like, it doesn't matter what, it doesn't matter what ideas are true.

It matters what ideas serve you. And the idea that like, whether it's true or not, that like somebody who's like really, really made it deals with the same struggles and it's just been, the game is actually staying in the game for as long as possible is like the thing you should do. That is an extremely helpful thought to have.

And I, I get that thought. I get that feeling from that.

Chenell Basilio: Yeah. Yeah. And they leave in all like the things that other people would cut out, like the mistakes and like the weird things that they say. And I love that.

Dylan Redekop: Yeah.

Chenell Basilio: Yeah.

Dylan Redekop: Yeah. It's good.

Chenell Basilio: Cool. Well this has been fun. Um. I'm gonna go not talk with my bronchitis and, and hang out, but, oh geez.

But no, this is a blast. I really appreciate, don't,

Nathan May: don't forget to pee on it. Uh, so

Chenell Basilio: before we started, oh no.

Nathan May: It's a jellyfish thing. Yeah, yeah, yeah. [00:59:00]

Chenell Basilio: Before we started recording, I was saying that I went back to the doctor yesterday and they were like, we can't really do anything. And I was like, no, there's gotta be something that you can do to make this go away.

And Nathan was like, just pee on it like a jellyfish. I was like, oh my God.

Dylan Redekop: Of all the things,

Chenell Basilio: of all the things. It's always worked the time. Uh, yeah. Well, on that note, where, uh, where can people find you and, um. Learn more about what you're doing.

Nathan May: Yeah. Um, find me on, on LinkedIn, Nathan May I I write, uh, what I, what I hope is, is really tactical stuff on building a, a business with a newsletter and, um, personal, IPO.

Um, we talk about, we take big people like Sam Par, Dickie Bush, Justin Walsh, Jesse Fuji. We're gonna do, uh, you know, Alex and Austin, all these different people. And we, we talk about finances, funnels, and feelings. So like, we help you build your business and we, uh, we get into the, into the fields, which is, is is fun.

So how do you go, go, go check it out.

Chenell Basilio: Yeah. Awesome. Yeah, it's a great show. I'm excited to listen more. [01:00:00] Thanks for coming on Nathan. This was fun.

Dylan Redekop: Yeah, thanks. This was great. You guys having me.