The Power Of Email Newsletters: How To Start, Grow & Monetize Your Own 6-7 Figure Newsletter – Ethan Brooks

EP 18 – Ethan Brooks – Email Newsletter Expert & Writer/Senior Analyst at The Hustle

If you’ve ever considered starting an email newsletter or already have an email list and don’t know what to do with it… this interview is a must listen.

I was fortunate to have a great conversation with Ethan Brooks, Email Newsletter Expert and Writer & Senior Analyst at The Hustle.

We covered A LOT of ground in this interview. While Ethan has spent an insane amount of time studying (and working on) 7 figure newsletters, we spoke a lot about how the average joe can start a 6 figure newsletter.

I even went into detail of how I generated 6 figures off an email list I had and we brainstorm the ways I can pivot it into a newsletter. Those are the types of conversations that typically happen off the mic but I thought it would be incredibly valuable to listen to.

You can listen to this episode on Apple Podcasts and/or Spotify. Also you can watch the video version of this interview on YouTube!

Show notes:

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[expand title=”Click here for the raw, unedited transcript:”]

This transcript was automatically generated using Descript.

Ismail: Welcome to The Bound to Be Rich podcast, where I attempt to reverse engineer people who seem to be successful, no matter the circumstances, so that you can apply those lessons to your own life. I’m your host, is Mel Hummed. One quick thing before we get started. I am starting my own email newsletter and I would love for you to join it.

It’s going to be like a personal note for me to my friends, of all the best things that have come across that month from hacks and tips, interesting stories, products, books, ways to make money, and who knows what else. It’s totally freight and if you don’t like it, you can always opt out at any time, so there’s no downside.

The link to join is in the show notes, and I hope to see you on the list. In this episode, we are joined by Ethan Brooks, a writer and senior analyst at The Hustle. The Hustle is a startup media company with a daily newsletter sent out to one and a half million subscribers. They were recently acquired by HubSpot.

Ethan has spent months researching and studying the newsletter business. He’s considered an expert on seven figured newsletters. We talk about how to grow and monetize newsletters, why you may consider starting one and why this may be the best time to do so. Seven figured newsletters sound awesome, but I believe we live in a day and age where it’s possible for the average Joe to create a six figure newsletter or a small business to potentially create a newsletter for their target clients.

I even shared in detail how I was personally able to generate six figures from an email list of only a thousand people. Then we get into the nitty gritty of an idea I had for my own newsletter product that I’m launching, and how I could pivot my email list into its own newsletter. I think you’ll find that exchange very.

Let’s dive in.

Ethan, thanks so much for coming on, man. I really appreciate you making the 

Ethan: time. Yeah, absolutely. Thanks for having me, man. I’m 

Ismail: stoked to speak with you. I’ve wanted to speak with you for a long time. Uh, but listeners know I had, I had a baby. It’s a whole, it was a whole thing. So I’m glad to finally get that chance to talk to you.

And I, I have some notes. Uh, 

[00:02:10] Twitter Background image.

Ismail: first of all, I came across you, uh, I imagine a lot of people did with a Twitter, one of your Twitter threats. You’ve got a few of them now that are really, uh, amazing and valuable. And I heard on another, I was preparing for this episode and I heard another podcast where you referenced someone ask you about your Twitter background photo.

And you don’t have one and you had a great answer, so now you can’t have one. I’d love to, I’d love to hear that answer. Cause I don’t have one either. So . 

Ethan: Oh, , yeah. It was, uh, it was Tim Stoddard stad over at, uh, copy blogger and, oh God, I don’t remember if I had a great answer or not, but you know what it was, was, so he opens his podcast every episode asking, you know, what is the background story behind your background photo on Twitter?

And I don’t have one. I’m not really a Twitter. I, for the longest time, I wasn’t a Twitter guy. And, uh, I think we were, we were joking on that show about like, now I, now I almost can’t have one. Right? I’m on the record saying like, I don’t have one. And he was making up, I think some, you know, crazy story about why that is.

But, um, now I don’t, I don’t have one. And that’s unfortunately now I’m on the record twice as saying it, so my apologies. Yeah, yeah. But I, uh, no, I don’t have one. And, uh, thank you for the kind words about the, the Twitter threads. I, for the longest time was not really a Twitter person, but, um, got into it recently just to publish some research related to newsletters that we didn’t really have an, an outlet for anywhere else.

And it seems like it’s, um, gotten a little bit of, of traction there. So I’m increasingly a Twitter guy, but not still not a Twitter guy with a background. Unfortunately. I, I also have, 

Ismail: have no background. It’s funny. Um, I have a weird problem where I have audio listeners. And I have a very hard time translating them to like YouTube subscribers or social media followers.

So my, my social media is like bare bones. I’ve got no followers, but I’m able to interview all these incredible people like yourself. It’s usually the other way around where people have social media followers and they can’t transfer them to the podcast. So it’s 

Ethan: backwards. Isn’t it funny, I, you know, I noticed the same thing.

Uh, well, I, I don’t know. I’ve never met him, but, but Tim Ferris seems to have sort of an interesting hang up with, uh, video. I mean, versus his work, which was text in the beginning. And he’s got just this incredible community of people on Twitter and on the blog and all these people. And, but I think he’s launched video two or three different times and for whatever, I mean, I love this, the shows that he’s put out, but it seems like he’s kind of stuck with the, the initial domain.

And I don’t know if that’s, I think it’s a user type, you know, like there’s a certain. Audience, they just don’t consume other things. Right. 

Ismail: I’m, I’m a huge Tim Ferris fan, by the way, and I, he’s also from Long Island. Um, 

[00:04:56] Audio listeners vs social media followers.

Ismail: I think the people that listen to audio are like more of the, I don’t wanna offend anybody, but they’re more busy people that are like multitasking or driving or, or doing or working out and listening while they’re doing other stuff.

They don’t necessarily have as much time or they don’t devote as much time to social media or not. And I would argue that, um, the audio listener, like someone that’s gonna listen to this hour podcast every week is way more valuable than X number of social media followers, just in my opinion. Um, so I’m grateful to have them.

I just, it’s just a funny, backwards problem that I have. Um, but I think I prefer it this way the other way. 

Ethan: They, they’re probably far smarter and way better looking as well. , 

Ismail: Well, I was actually pushed to, to pivot to video and I’m sure Tim Ferris had the same thing where, um, some of my guests were like social media pros and they said, You have to get it on video and repurpose the content, make social social clips out of them and put ’em on social media.

And I did test it. I don’t know if you’re interested in this stuff, but, um, I did TikTok clips in just last week. I went viral on TikTok and I got, I’m in the Creator fund, so now I get paid to make TikTok. So really it does work. I, I think a lot of people don’t, they’re sleeping on TikTok for, um, acquisition like business people or podcasters or creators.

I think everyone’s kind of stuck on the old platforms, but I found it. I was nobody. I put up a clip, 30, 40,000 people viewed it. I put up another clip. I got a quarter million views and 10,000 people subscribe. Like, it’s just crazy. The power there, if you make a content. . 

Ethan: That’s fascinating. Uh, I’m curious, when you said 10,000 people subscribe, is that, are you able to get them off the platform over to the podcast?

You’re saying they subscribe to the podcast? Yes, so 

Ismail: I, yeah, I’ve had some success. I mean, it’s, it’s not a huge percentage of them, but I definitely noticed a bump in my listens. Um, so if I, if I put up a clip from an audio, uh, from an interview and they like that clip, I refer ’em to the link of my bio and then they can see the full interview on video or on audio, whatever they prefer.

So I do notice a pickup in, in downloads when I see a clip doing well. Um, there’s no way to measure subscribers on, on podcasts yet, though. It’s like, it’s still a very early that the data statistics in the podcast were almost still really not there. 

Ethan: That’s so interesting. Yeah. The people, I’ve heard the same thing from people, uh, basically everybody who’s talked to me about TikTok has said that they’ve had some kind of like just mind blowing experience there.

And also that it seems to be sort of a. Like a, I almost wanna say like insular audience in that like, if you build an audience on TikTok, you’ve got your audience on TikTok. I think people are still kind of figuring out how to move that audience off onto things like newsletters and podcasts and stuff like that.

It is such, it’s such an interesting environment. Um, but I agree with you that people are just coming around to Figur. Out the power of that platform. I’m, 

Ismail: I’m convinced anybody can get big on TikTok, like, I don’t know what the term is, but it gives equal opportunity to every creator, which I’ve never seen before.

Um, so in this world where, I don’t know if you’re into crypto or other, we’re, we’re like trending towards more decentralization. And I think that’s kind of along the same realm. Um, and I actually had, I noticed like people subscribed to my Instagram from TikTok, uh, my YouTube from TikTok, not huge percentage, but they do.

So if you get a hundred thousand TikTok followers, I’m sure maybe 10,000 of them would move over to the other platforms. Uh, just been my experience. Uh, so okay. My next question,

[00:08:22] Why did you want to be a writer?

Ismail: These are just like, like set up questions. I I, uh, I heard you were working at Top Towel in recruiting, if I remember correctly, and it seemed like a dream job.

Like you were doing happy hours and meeting people and recruiting developers. Uh, but you wanted to be a writer. Why? 

Ethan: Oh, wow. Great question. Um, and also great research. So yeah, I, I was, before I, before I worked over at the Hustle, I was at Top Talent. It was, it was Dream job. I was, uh, I was on the community team, so I led their community growth efforts for North America.

Um, and I didn’t, That was a job that I stumbled into. So I was at, I, my first love ever since I was a kid was writing, and I actually went to college for journalism initially, and it was there that I stumbled on the four hour work week, which I think everybody RH is like a similar story, right? So like right back when it came out, 2008, in fact, my dad told me, he’s like, You’re gonna love this book, Four Hour Work Week.

And I read the title and I’m like, This is the biggest scam I’ve ever heard of. And, uh, , I think it was like two pages in, Man. I was hooked. I didn’t put that book down. It was the first time. Uh, I ever felt like somebody was saying what I felt in terms of like how you can kind of organize your life to, to, to better align with your goals.

And you don’t always have to be working. You can kind of mix work with these mini retirements, the whole thing. I mean, everybody’s heard this before. I loved it. So I switched to entrepreneurship and I’ve spent the ne the, the next, you know, 12 years or however old I am now, uh, helping first as a developer and then helping build startups, rank community at top, tell, So I specifically helping recruit developers.

And then, uh, the reason I left was, uh, my grandfather passed away and it was, you know, it’s, it was just one of these moments where um, sort of like everything you’re working on comes into sharp contrast. And I remember I was there with him and I d know, it just kind of hit me like, Time is limited. Am I really gonna be happy if this is what my entire career is?

And it was a great job. I did, I flew all over the world hosting happy hours with like some of the most interesting people I’ve ever met. Ex fang developers and designers, and just fascinating people. It was great. Um, but it, it wasn’t really what I wanted to do, so I didn’t have any plan. Um, and I was really nervous about it.

I was really nervous about leaving. I was making the best money I had ever made in my career. Um, but I knew that I had to go try and do this thing. And so I left with, I don’t know, it was like 10 grand saved or something like that. And spent a little bit of time just kind of bumming around Europe and uh, and then got, got into contract work and it was basically the story of my career has been a lucky.

Stumble into writing. Uh, Steph Smith and I worked together over at Top Towel and she moved to the hustle before I did, and she ended up pulling me over. So that’s a long story, a long answer to your question, but the reason that I tell it is, um, I know a lot of people who are sort of considering making a leap, and obviously that’s a decision you have to make with your own support group, like your own, your family or your spouse or whatever.

But the thing that I learned there in that particular move was that the path from where you are to where you wanna be isn’t always clear. And sometimes, uh, you do just have to take a leap and, and things just kind of fall into place afterwards. So, 

Ismail: I mean, I appreciate you getting into that story. There’s so many things to go into with that and I can’t help my curiosity.

Um, so 

[00:12:16] Moving on from a bad experience.

Ismail: I’m just, I’m just gonna follow it. I think, um, a lot of people listening feel the same way, and I’ve seen through this show. That there’s, it’s never been easier to make a living doing what you love, right? Um, talking to interesting people, creating social media clips, like whatever you love. Like if you’re obsessed with the S Smurfs, you can make a living selling Smurf toys on eBay.

Like, it’s never been easier. But I think there’s one thing that you mention, and then this has come up a few times at everyone had had a death in the family or had some moment where they kind of reflect on their life in themselves. Uh, but oftentimes, and I’ve seen this too, uh, real life pulls you back.

You know, you, after you, you think about it, you know, maybe a couple days, a week, whatever, but then you gotta go back to work. You got your bills, you got your whatever, and you kind of forget that and get pulled back into the old routine. How did you get out? 

Ethan: That’s, uh, that’s a great question. And I, by the way, I completely agree.

In fact, I don’t think we’re designed to live with a persistent knowledge that time is running out. Like you’re designed to forget that life is short. You’re designed to forget bad things that happen. Like there’s a really good reason that you do all these things cuz you’d go insane if you actually remembered how limited your time was.

All. Like, if you’re just constantly thinking about how the end is not, Um, so I, when I, when I think about this or when I talk about this with people, I always say like, it was one of those moments and you’re gonna have a bunch of them throughout life, right? But you’re not designed to stay there. If, if you’re living in a spot right now where you’re like comfortable or you’re just kind of in the grind, like that’s what you’re supposed to be doing, that’s most of life.

So, um, when those opportunities come around, I think it’s important to sort of honor them for what they are. And if. Like, if it means making a, a change, that’s fine, but it doesn’t mean that you wasted your time before that. Like this is, this is, this is what most of life is. So, uh, how did I get out? Let’s see.

Um, for me, why 

Ismail: did you, why didn’t you let yourself fall back into the old routine? 

Ethan: That’s a good question. So I’m trying to kind of walk myself through it. It was very visceral feeling. I was super nervous cuz I, I loved my, we were very close knit team, um, inside of an incredibly demanding workplace, like top style for anybody who knows that company was in hyper growth.

So, I mean, like, it’s just an incredibly, incredibly competitive, uh, domain with a lot of the smartest people I had ever worked with. And, and, I guess the term I’m gonna use is, luckily that experience was, um, jarring enough that it was able to kind of cut through that noise. And I think maybe that’s why it took me, You know, the interesting thing is after I left, I was going through some old journals and I realized I really probably should have left earlier.

Um, you know, I just, I had like made notes to myself about things that I wanted to do that had indicated that really this was on my mind for a while, but it was that experience that was sort of resonated loudly or strongly enough that it made it, if not easy possible to sit down with my boss and say, Look, I gotta go do this other thing.

And, uh, you know, it wasn’t that simple. They, we were a tight knit team. We had a lot of really big projects in the works. They tried to keep me there and I mean, which I was, uh, really touched by, you know, they tried to help me design a new role that was closer to what I wanted and stuff like that. Um, but in order, it ultimately came down to they, they, uh, and I think I can say this publicly, So they offered me a new role and I, uh, was trying, and I had worked back and forth with them.

I’d interviewed for this new role and I had basically convinced myself that I wasn’t going to leave if I wasn’t gonna get this new role. It was actually working on steps team, so the publications team. Um, and I, I thought, yeah, I think this is it. And I sat, but it came with some strings attached and I sat down to write the, uh, the acceptance letter.

And I must have drafted that damn letter like 14 times. I’ll never forget it. I was sitting in a, an apartment in Santiago, Decom Costello, which is in the northwest corner of Spain, and I couldn’t write it. And so just as a thought experiment, I wrote the, the, the, what would you call it? Declination letter.

The no letter, the, sorry, I’ve got a go letter. Uh, the thank you for the offer, but I really, I, I can’t, I have to go. And that, I mean, it just, it just flowed. It was done in 10 minutes and as soon as that happened, I knew I had to go and I, so I, I called my boss, my boss’s boss, and I said, again, you know, just thanks for everything, but I have to go do this other thing.

And so, um, I think a lot of it comes down to developing that sort of like an attunement to what you’re really feeling. And, um, I don’t, I don’t know that you can carry that with you all the time, but at some points in life, it comes through louder than others. And, and when that happens, uh, the great things can happen if you can learn to tap into it.

I mean, 

Ismail: I don’t think I’ve ever gotten into this story yet in the show, but I feel like I, 

[00:17:43] Ismail sharing his work experience story.

Ismail: I relate to that in the, in respect to like, I was the guy that was always doing side hustles and, and trying to break free of the corporate world. I worked on Wall Street and telling all my friends, I’m gonna quit one day.

I’m gonna go on my own. I’m gonna do it, I’m gonna do it, I’m gonna do it. Um, but I never did. And I remember the first time I tried to do it, one, one firm, uh, they just threw more money at me. And I was like, Wow, . I, I guess I’ll stay . And then, and then I went to another place and, and then the same thing happened.

Uh, but the one thing that pulled me out is that, uh, I had a first part of the story that I had a friend that had a baby, and I remember working together. I’d walked by him by his desk and he’s looking at, at the phone, uh, a live FaceTime of his daughter. He’s like, Look, she just had her first steps. Why am I here?

Why am I here? Oh, wow. And I was like, Man, when I have kids, I’m not gonna be here. I’m not gonna let that happen to me. I don’t know why that stuck with me. Um, so. Had my, my daughter, my first child. I was at home for a while. The first day I went back to work, like I sat down and I’m like, I have to quit immediately.

Um, I have to quit immediately. Like I didn’t even, I’m like, I’m sorry, my boss. I, I don’t wanna wait. I can’t, I have to get this out. Uh, but that whole weekend before I went in there, even though I was so decided in my whole last few years, I was preparing for this moment, uh, it was extremely difficult. I remember the visceral feelings of like, Is this the right move?

I’m scared. The fear, I don’t know why it was so difficult, but it was really extremely extreme. One of the most difficult decisions, even though, I dunno if it’s a decision part cause I made that decision, but to go through with it, it was so hard. So I can totally see why people have the dream but they can’t go through with it.

Cuz your whole life, you’re raised with that fear. Oh, you have a good, good job. Get a good degree. Follow the corporate ladder, put the time, like all these things that are drilled into you, it’s hard to. Forget all that, you know? 

Ethan: Totally, Totally. And I, you know, it’s funny that you, 

[00:19:42] How Life is not always a clear path?

Ethan: that you mentioned this, uh, because hearing that story, it, it, well, it reminds me of two things.

One, I think very often, I mean, this is a data point of two so far, mine and yours. But it seems like it, it’s never, it’s never the, the huge thing. It’s always these small things like you keyed in on this phone conversation, you’re walking by somebody’s desk, and it’s like a, I mean, it’s a quick moment of your day that just changed everything for me.

Uh, I’ll, I mean, I, I didn’t say this specifically, but I will never forget the image was sitting with my grandfather. He, you know, he had been basically, um, like he was on the respirator, he was unconscious, and he was one of the strongest men I ever knew. The man fought in Korea. He, uh, w he spent 20 years.

Laying granite curb during the day. And then he would work at the firehouse at night as a fireman for Buffalo Fire Department. So this guy who had been basically unbreakable, I mean he had like multiple heart attacks without even realizing it literally, and was all of a sudden, um, kind laid low in front of me.

And I just remember watching his chest rise and thinking to myself, It’s gonna end, it’s gonna end someday. It, you just, you can’t, you can’t run from it forever. So it was one second in time, I think, but, but I will never forget that image. And it was ultimately what made everything else easy. And then the other thing that I think is helpful for people, this was certainly helpful for me.

In fact, this is kind of a funny story. I had gone through this experience and I was just coming back to work after, you know, the, like the funeral and everything. And I was, I had it in my head. I’m going to like, put in my resignation. And I was still really nervous. As I said, you know, I was like, coming from a freelance background, it’s hard to give up steady paycheck, right?

Especially if it’s a good one. And all of a sudden I, I read an interview, uh, on like Financial Times or something with my boss, like he had just ran, I have Google alerts set for everybody in my company just cause like my communi my community function and his name popped up. He had been interviewed by some financial, uh, publication and like one of the first things he was talking about this and he said, A lot of people are afraid to lose to leave their jobs because you sort of have a natural, uh, assumption that if you leave, you’ll make less money any, wherever else you go because that’s one of the potential outcomes you could actually make more.

And as soon as I read that, I was like, Oh, wait a second. That like, I, I may not be walking away from the best career I’ve ever had. I might be walking towards it for whatever reason. That’s not a normal assumption for us to make. Uh, but for anybody who’s listening, I mean, that actually ended up being what happened.

I make more money now, which I can never believe as a writer than I did, uh, working in, in startup. So for any, again, for anybody who’s considering this, um, to whatever degree this story is helpful, just know that it can work out better. The path is not always clear. And it was hard. I mean, I scrapped for like a year between when I left that company and when I was ultimately pulled into the hustle.

Uh, but it ended, it ended the way that I wanted to. And if I can belabor this point just one more time. Um, somebody asked in our community recently, they said, If you could go back in time one year, uh, to, and tell yourself anything, what would it be? And I mean, this was a little while ago, but basically it was right about the start of the pandemic.

You could go back a time one year and like prepare yourself, What would, what would you tell them? And um, for me, the only thing on my mind was this job switch. And I said, if I could go back, I would, I would tell myself it works out. It works out. So that’s it. Yeah, 

Ismail: I, I’m, I’m glad we got into that because I think sometimes these are the stories that stick with people the most.

Like someone that’s going through this and here’s, you know, our two data points, that’s what resonates with them. We could talk about newsletters for the next hour, but that little tidbit is what makes them think about their situation even more. Um, but somehow, let me pivot to the, to the topic at hand. Um, first of all, you’re like a newsletter guru, tactician, craft master, whatever you wanna call it.

An interesting side note, um, I’ve got a good friend that lives in Austin and he was at an event, and I think you were speaking or you, he sent me a picture of you on the whiteboard teaching something and he is like, Dude, you gotta talk to this guy. And I’m like, What a coincidence. Like, I’m actually trying to get him on the podcast right now,

So I thought that was like a, like a small world kind of moment. Um, and why he thought of me when he was listening to you. I don’t know. Um, that was just an interesting tidbit because it’s not like, uh, you know, we have millions of followers on social media. So the fact that that person there knew us both, it’s kind of interesting.

Um, That’s wild. Yeah. So, okay. 

[00:24:48] Email list vs. Newsletter.

Ismail: I’m curious to get into this newsletter topic because I’ll share my story. Uh, but first, if you don’t mind setting it up, a lot of people listening have an email list. Like they know it’s valuable to have an email list. You’re starting something, collect email addresses, right?

So they have some kind of email list. What’s the difference between having an email list and having a newsletter? 

Ethan: That’s a great question. Uh, if I was to characterize it briefly, I would say like, an email list can help you sell products. A newsletter. The way I would think about it is that, uh, that is the product itself.

And so, uh, Specifically what I research is how media companies, uh, monetize and grow newsletters where the, like the information itself, what you’re sending to people’s inbox is the product. Is is that, is that a good way of clarifying the 

Ismail: two? I love it. To the point and it makes sense. That makes perfect sense.

How about like, uh, comparing it to people have audience on social media platforms or podcasts or they have a blog. How do you differentiate the newsletter email list kind of thing versus those other platforms? 

Ethan: That’s a great question and I think, you know, as we get into it, uh, one thing that sort of unfolds is that there isn’t as much of a distinction as you might think in the beginning and the reason.

Media is really, media is the business model, the medium changes. So whether you’re making money by selling a newsletter or you know, like paid tweets or, uh, you know, a paid subscription on a podcast, those are all different mediums. But the, the way that you structure the business is actually the same. And we can get into what that structure is in, in a moment.

Um, but yeah, typically speaking, I would say all of these mediums have the potential, they have the potential to be either, um, traditionally they are just marketing mediums, right? Like for a long time we used podcasts to sell, um, a course or to sell, you know, knickknacks or widgets or whatever. So we use them exclusively as a marketing medium.

Um, what’s coming out now and the reason why newsletters are. One popular version of this is we’re finding that people are actually willing to pay for the information itself. And so you can take, uh, something like a podcast, well, a newsletter, and you can charge for it. Um, you can, so the email that you were sending for free, you can actually charge for that.

And we’re, we’re sort of a figuring out how that business model works. You can do the same thing with tweets, right? Like, so you can actually have premium tweets and, um, it turns out the way that you would monetize that is the same as the way you would monetize a newsletter. Uh, so they all work into this overall media business, which again, I’m happy to get into in a second.

But, um, the big difference is, and this isn’t as new as it’s, and a lot of people think that it is, but it’s, we are figuring out that these mediums we used for marketing can be the product themselves. And I think that’s kind of an exciting prospect for anybody who is interested in these different niche areas.

Because it can now help burn you a living. 

Ismail: It, it’s fascinating because I remember when Twitch first came out like, this is the gaming, or people play games on it and people watch you. And I was like, Man, why would you watch someone else play games? Uh, but, and like there’s a huge, huge community of people that do this.

And like my family members pay monthly to their favorite Twitch people. And I’m like, Oh, what do you get? And they don’t get anything like . I don’t remember exactly what they get. It’s probably something really minor, but they really don’t get anything. They’re just supporting those people. And for me, for the show, I, I saw this thing called Buy Me at Coffee.

Have you heard this site? Buy me Yeah. So I was like, You know what? Let me throw this up there. And lo and behold, people listening, and I love the people listening started sending me money to buy coffee. So obviously it’s not a, it’s not enough for an income, but to me it’s like mind blowing that the things that you thought should be free, uh, and are free.

Forget about charging for it. They are free. There’s people out there that are just wanna support you. That’s something totally different than like, I don’t know what your age exactly is, but me growing up or like our parent generation, like people didn’t just give you money for free. Like we’re in a totally different era now.

Like people are throwing their cash app up on social media of their Venmo. People give money away for free. So I think if you can do anything to step into that universe and create content and earn a piece of that, uh, it’s never been easier than before. Uh,

[00:29:31] Is the newsletter area too saturated?

Ismail: do you think that, uh, this newsletter area is too saturated?

Cuz it seems like everybody’s got StuffSack and everybody’s starting their own newsletter? Or is this a new paradigm shift where people are wanna pay for content? 

Ethan: Uh, great question. So, I’ll answer in two parts. First, the paradigm shift. It’s true. People are paying for content more now than they probably ever would have 10 years ago.

And if I had to guess, I would say maybe that’s because we just came through this age of just the mass proliferation of free content. If you look at what people pay for now, they’re not paying, uh, for the types of generalized news they get by scrolling Twitter, right? They’re paying for the things that matter the most to them.

And the reason is cuz there’s so much information out there, it’s hard to find the good, the good stuff. Um, so in some way, I think maybe the, the current levels of opportunity are a byproduct of the fact that we just came through this massive internet age of just free, free information. That’s 

Ismail: such a great point.

And I hate to interrupt, but like, I think people are more, they’re following you as a curator now. Like people follow me to curate the content for them. And it’s funny cuz like years ago I remember talking to, I think it was my brother, there’s so many new TV shows, Netflix pumping money into this. There’s YouTube things, there’s Twitch things, there’s so much content you just cannot keep up.

Mm-hmm. . And who would’ve thought, I would never thought that there would be even more content five years ago and people would start paying for it. So it, it went, I’ll admit I was totally, it went in a totally different direction than I saw it going. . Totally. 

Ethan: Yeah. And, um, I mean, there’s another component to it, which is that the technology is there in a way that it was never there before.

And it’s, that’s kind of an interesting aspect because it’s easy to lose sight of that, right? Like we, we live in an age where Venmo is just an easy thing to do. You remember how, what a pain in the asset was to go to a restaurant with friends before, right? Like, we gotta split the bill up and who doesn’t have cash?

And it, it used to be a major pain, but these technologies, they ca they come into the world and they change things that much and we just forget, you know, how hard it would’ve been to build a paid newsletter 10 years ago, Or even in Amazon. I mean, Amazon marketplace only started, I think it was about 10 years ago.

Uh, and back it was still hard to do. And now it’s not. I mean, I I heard your most recent interview, uh, I forget his name, but he, he created the, the e automated e-commerce company. Yes. And, um, the, the reality is there’s just, there’s a lot of tools that are supporting this in a way that has never been supported before.

But I would caveat it with one thing and I would say, While it’s true that there’s probably some cultural and techno technological elements that are making this easier and more accessible than ever before, the business model is as, as time, and so and so. No, I actually don’t think it’s saturated. Uh, and the the reason is if you know how the business model works, I think you’ll always be able to make money.

Uh, because it’s, it’s universal. It, it can be applied to this domain, or if you find other mediums that are more popular, like, let’s say it becomes pop, it becomes possible to monetize TikTok in a way that you can’t currently, this exact same business model transfers. Um, so, so, no, there’s, I, I don’t think there’s any such thing as full saturation.

In fact, Steph Smith has this. Quote, which I will, I’ll attempt to paraphrase, but she said, basically, when people talk about saturation, what they’re really talking about is what’s the likelihood that you can innovate on what’s currently offered? Like, what is the, what’s the likelihood that you’re able to create something that is better or, uh, or different?

It. And, uh, the reality is most people who are gonna try and do that, you know, try and compete in this space, they’re, they’re, they’re not thinking about it in these terms. And so they’re not actually able to out innovate the incumbents people like the hostile or like morning brew, who are these massive email giants.

But anybody who understands how the business model actually works, uh, you dramatically increase your odds of being able to make this function as a. And now 

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All right, let’s get back to the show. All right, so let, let’s, um, get into my example. And I usually don’t do this much talking, uh, in my interviews. I’m usually just lobbing questions, but I think part of the reason I was really excited to talk to you is to see you dig into this with me, and I think it’d be very, People listening, it’ll be a little weird for me because, uh, a lot of people on my email list are listening.

Um, but whatever, I think it’s gonna be very helpful. So my, my, 

[00:35:23] Ismail sharing his email list building.

Ismail: my whole story, and I think I, I gave you a brief snippet if I remember correctly, but I basically built an email list over the years, um, in a very small niche market. It’s like the photo booth business market. So there’s these people that have these companies and they rent photo booths to parties, weddings, corporate events, et cetera.

Um, I started one with my brother and I ended up building a software to help us run our business, and then I started selling that software to other photo booth business owners. So I built the first part of that email is that way. Um, and then I met someone in the, initially and we started a podcast and it ended up being the number one podcast in the world for this niche.

So the email is crew, uh, and then I was like, you know, Let me do a conference. So I, I did my own event. We did a few meetups, uh, smaller meetups around the world for podcast listeners. Um, I started creating courses, not me, but I was pulling in like the top leaders in the industry and creating courses with them and selling it to the email list.

So I was, I was kind of stumbling my way through this accidentally. And I think I, I, I have like 1300 people on the list, which is not a lot, and probably a thousand active subscribers. And that includes like, um, industry leaders, uh, smaller booths, um, companies that are in the industry, so that, that includes everybody.

And it’s only a thousand people. But I, I’ve generated well over six figures in income from that list. Like accidentally just from stumbling. I don’t even know, Like I just kind of went from one thing to the next thing, kind of like what you were saying, uh, with your career. So, Now I’m at this point where I’m like, You know what?

I wanna focus more on higher scalable and higher leverage things like the podcast. This is fun for me. I learn, I meet cool people, but people get value out of listening. So how do I use my standing in industry to do less of the event work, which I don’t really do anymore anyway, and do more of like, uh, the influencer work or, uh, being an industry leader and tying people together and organizing the information for them because it’s an email list, not a newsletter.

So I was spitballing this with my wife last night and I’m like, Hey, and I’m gonna buy this domain before I publish this episode. So nobody tried anything, but I was like, I should start something called the Booth Report where everybody opts into this list. It’s a free email newsletter. And I’ll curate and organize all the content, uh, that I think’s valuable for people, whether it’s an interview or something that happened in industry and send that out to people.

And I’m sure there’s a ton of ways to grow and monetize that down the line that maybe will help me with. But I think, let me stop there so far and get your. On what I did so far and what I just plan on doing. Does it make sense? 

[00:38:03] Ethan’s take on newsletter business.

Ismail: What do you, what’s your take on it? Cause you’ve, you’ve dug into this for like, I think you studied this for months or years, right?

Ethan: Yeah. So I love everything about this and I’ll get into why in a second. But, uh, just to answer your first question, uh, yes. So about a year ago we at the hustle, we realized that this whole newsletter business had really taken off publicly. We’ve been running a newsletter for almost five years, I think at that point or six years.

And so, you know, there’s a couple companies in the landscape now that have really made that work. The Hustle was one of them. Morning Brew, another, it is a bunch. Um, but our readers had always been asking, like, give us the playbook for how to build a newsletter business. And we had done some small versions of that, but what we really wanted to do was break the whole industry wide open and, and really figure out like, how does this work?

How do you build specifically a multimillion dollar. Media machine. Um, and so I was the, I was the lead researcher on that for six months. And we talked to people across the industry, whether it was us, uh, Morning Brew, New York Times, buzzfeed, WaPo, all these people who run these massive media companies also interviewed across our entire team.

So digging in with like the growth team or, um, even our like ad sellers and just every single position that we, that we could in order to really understand how does, like what, what are the nuts and bolts of making this business work? Not just the general idea, but right down to the nitty gritty. Then the acquisition came and, uh, all of a sudden we didn’t need the revenue from this product anymore.

So the project was basically put on hold and we’ve been publishing it for free. That, and that’s why I’m now on Twitter. So thank you, by the way, . . Thank you. Um, So I did have a chance to look into this and, and I’ll tell you, I love, I love your story, uh, for a few reasons. One, because it’s so niche and you did, you, you texted me, you said, Hey, look, I’ve got a list of about a thousand people that we’ve made, You know, we’ve monetized up to the six figure mark, and I’m curious about some next steps that to think about.

And that is, that’s just, that’s awesome. Uh, it’s rare. It’s, it’s, it, it’s, it’s, it’s not rare because it’s impossible. It’s rare because most people are too scared to go niche to ever pull it off. Like they, they wanna start the next morning brew, or they wanna start the next, 

Ismail: See, I, I would say, when you tell me about the morning brew and the hustle, or I think people listening, they find that intimidating.

Like, how am I gonna get a million person email list? Or like some of your tweets talked about when you have 75,000 people, then you can do this. But it’s hard to get 75,000 people. It’s hard to get 50,000 people. I only have a thousand. That’s why I hope people take from this thing. You could be in the corner of the universe, in the photo booth market that I think other people wouldn’t even know existed and have a thousand people that it’s like a thousand true fans.

I’m sure you know Kevin Kelly’s, uh, blog post. You find those thousand people and you can earn a comfortable living from them. It’s, um, I don’t know if it’s easy, but it’s not as difficult as people think, or it’s way easier than getting a million person email list. 

Ethan: Totally, yes. It’s, uh, I think I like, I love Warren Buffet’s phrasing.

Uh, it’s simple but not easy. and, um, so here’s how it works. Let me, let me break down what we found at least. This is, this is what the research showed, and I, I would say this has been verified just from what I’ve seen working inside of the hustle as well. Um, 

[00:41:39] 3 ways to make money from newsletters.

Ethan: this is what the, the, there are basically three ways to make money from a newsletter you have.

Or, or I would say there’s three types of newsletters. So there’s free newsletters, there are low price subscriptions and high price subscriptions. Your free newsletters are monetized via ads, so usually your biggest audience, uh, obviously low price subscriptions are paid. And then high price subscriptions are paid low price subscriptions, by the way we call them front end products and high priced are called back end products.

And so the idea is that you cast the, the, the way like Morning Brew or the Hustle, the way that they’re kind of making this work is you cast a really wide net with the free newsletter, and, uh, you work up to that 75,000, a hundred thousand a million plus readers, and you’re, you’re monetizing that via ads, uh, whether through CPMs or like affiliate placements.

And it’s, you know, different reasons for choosing each one, but. , uh, that’s, that’s where they’re starting. And then you use that list as distribution to pull people deeper into your ecosystem, sell them and sell them a front end product, which is sort of, uh, the distinction between front and back end products.

I’m gonna, I’m gonna tie this back to your project in just a second. The distinction between front and back end is usually there’s two things. Uh, their level of specificity and their price. So a front end product is usually like a little more specific than your free newsletter. Uh, so in the example of the Hustle, we have the Hustle, which is like a business newsletter.

And then we have trends, which is a paid product specifically about emerging business opportunities. Still pretty general and like a lot of the readers from the Hustle have been pulled into trends, but, uh, it’s not, it’s, it’s not, it’s like one step more specific than the da the free daily email. So the.

Front end product is typically a little more specific. And then, uh, the prices are usually around a hundred bucks a year. That’s kind of where they range. So like five to 10 bucks a month, something like that. Backend products are usually much more specific. These are the products that cater to a very specific niche and uh, like the photo booth operator industry potentially.

Uh, and they are more expensive and they solve, and this is really important, they solve a valuable problem, right? So when I say they’re more expensive, backend products typically start around four to $500 a year, and they can go all the way up into the thousands. And I mean, it’s like if you look at, uh, James Cher, Yep.

He’s got backend newsletters that are like three to $5,000 a year a piece. He’s able to charge that money because they are super specific, often like investing letters that focus on a very specific, uh, strategy. And the logic for anybody who’s apply or who’s applying is, um, you know, if I make one great deal over the entire year, I’m gonna, I’m gonna, I’ll make 10 grand.

Right? So why not pay the 5,000? Cause that seems like a, an easy bet. This ties into what you were saying earlier about like, what do people get when they support a Twitch streamer? It turns out there’s sort of a different psychology between these two paid products, uh, on the front end. The purpose of the front end product, the reason that it’s priced, where it’s priced is you want it to be inexpensive enough that people almost don’t think about buying it, right?

Like it’s, they’re buying it cuz they want, It’s just like it’s an inconvenience not to buy it. Right? So they want access to the information and or they just wanna support you. Right? Backend is different. Backend products are driven primarily by self-interest. So you have to be solving a problem that. Is valuable to somebody and, and, and you charge for it.

So what you’ve built so far, if I had to, um, sort of fit it into that model, you’ve got a really interesting niche list. And the idea, I mean, so far it’s free, right? So you, like you said, you just have an email list. Um, but because it’s so niche and because you have the potential to actually be solving problems for business owners, if you were to start an email product, I would actually categorize this, or I think you’ve got the potential to start at either that front or backend range, which is actually, uh, it’s rare to be honest.

Usually the reason for that is usually your free newsletter is distribution for your front or backend newsletter. So, um, if people don’t have a large list out of the gate, it’s really hard. To sell any kind of paid newsletter. This is why so many subs, stackers have a hard time. It’s like, if you don’t have a preexisting audience, how are you gonna get people to buy your product?

Um, in your case, you’ve got, you’ve got the email list and it’s really just a matter of going to these people and saying like, Hey, I’m thinking about doubling down on this and providing, and we’re gonna talk specifics about this industry. Do you want in, I think, I’m guessing, but I, I would, I would hypothesize that you would see a fairly strong opt-in rate on something like that, whereas the typical front end product you’re looking at like one to 3%.

I think you could potentially see even higher than that just given how niche you feel this. And so that might be where I would start thinking about this. So I’ll pause 

Ismail: there for a second. Yeah, I, I think when you were talking through the front end, the backend products, I, I felt like when I was thinking of my situation, I.

Just an email list to sell my products. And they were all the higher value backend stuff, the specific courses, the conference event, um, the software product. And I didn’t, I didn’t think I had that, uh, low cost, affordable thing. Maybe it was coming to a meetup, maybe that was the only one that fell in that category, but it was more of backend stuff.

So now you’re saying it would be easy, hypothetically for me to do something that’s like 5, 10, 15 bucks a month. Um, that, that I have resistance to that. So you, you, you can challenge me and, and dig into that if you’d like. But I have resistance to that because I just, generally speaking, the event industry has struggled, um, with the pandemic and all this stuff going on.

So I thought maybe it was not the right time to do that now and maybe start the free newsletter. To collect that whole audience and maybe grow it. Cuz I would, there’s no official data on this, but I think for my information, I would say there’s about 30,000 photo booth companies in the world. Uh, so I’m, I’m only a small portion of that so far.

So maybe I can get my list to 5,000, 6,000, 7,000 and then do something that’s at lower cost front end product. And then I already have a lot of the back end stuff in place. So hopefully that would go well. 

[00:48:36] a. Is it ok to initially start a free newsletter & collect the audience? b. Type of Content that people love.

Ismail: The question I would have is, does that make sense or am I wasting my time? And secondly, what kind of content do you put in these things?

Um, whether it’s the front end, the low cost product or the free product to get people to want to be part of it. 

Ethan: Great questions. Yeah, so I think a lot of this is subjective and uh, obviously like, I think your audience will tell you, and this goes for anybody listening, your audience will tell you better than, uh, anybody else, you know, whether or not they’re ready to buy something like this.

What I will say is that, A lot of times you can test these ideas for, for, for relatively low stakes. And so, uh, you know, we always did this all the time at the Hustle. Um, back before the acquisition, we had several, you know, being like a scrappy startup, you’ve always got a few different potential revenue streams that you’re thinking of.

And, you know, we had everything from paid like mastermind communities that we thought might, might be a good fit or in this case, like a deep report on specific industries. And we wanted to test all these things. And so we, you know, we would just spin up a landing page and then, then you announce it through the newsletter.

You see how many people buy in and, uh, basically just don’t spend their money until you’re sure you can deliver. And then if, if the product doesn’t feel like a fit or if you know, you decide maybe you wanna go in a different direction, obviously refund bad money. But, uh, the point is testing, testing demand for this is actually pretty low.

Uh, lift. Once you have that initial audience that trusts you, and if you’re open with them and you say, Hey, this is like a thing we’re thinking about, are you interested? You know, uh, they’ll go with you on that journey. Uh, that being said, my opinion is that you, uh, you can probably do this sooner than you think.

And the reason, some of the reasons that you’ve mentioned to me, I, I’ll push back. Just let’s do it, , in case this is helpful. If the industry really is going through a crisis, which it is, we all know that events is, is have been really hurt recently, um, then that the people in that industry may be looking.

For help more now than ever before. Right? And there’s value to bringing that group of people together so that they can learn from each other. Um, and so in that way, because you know, the price is on say, a front end product are, are fairly nominal a hundred dollars a year. And because you’re not, you know, nobody’s required to buy them.

Uh, I think the potential downside to testing something like this sooner is quite low. And one other thing I’ll say related to it is that this is, uh, I had a chance to talk with James Ture and he, he was actually crucial in helping us understand this model. A lot of times, like front and back end come with some kind of community.

And so this is where. The lines between a newsletter product and an email list start to blur, right? Because yes, you’re selling information that regularly hits the inbox, but if you have, say, a curated Slack community of these people that can ask questions to each other, and that group gets together once on a Zoom call once a month to discuss like the biggest problems they’re having and the biggest, uh, like most helpful thing that they’ve found for their business over the last month.

And that is incredibly valuable, right? And if there’s one person who can, like, I mean, I, I, I don’t know, but I would argue you’re probably one of the best positioned people to bring this group together. Cause I don’t, I don’t know how many other people really are aware of it in the same way that you are.

Uh, there’s a lot of value there. So I would encourage you to, uh, to, to think about the, the value you could bring to a struggling community by simply bringing them together. There’s, there’s, uh, a lot of utility in that. 

Ismail: I also wanna be very respectful of your time. So I see that we’re, we’re nearing at the end of what we, um, originally said.

Is it okay if we keep going? I just wanted you, like, I just, just give a signal and we’ll stop whenever you need to, but I think 

[00:52:50] Why not start a free newsletter?

Ismail: this is really valuable will caught me off guard is because I’m talking to the newsletter expert and I I didn’t expect for you to tell me don’t start a, it sounds like that’s what you’re saying, don’t start a free newsletter, like go straight for the paid newsletter.

It was not within the options that I was expecting. Um, why, why not do the free as well? 

Ethan: Good question. Yeah. So technically you would probably be wise to continue growing the free list, but that doesn’t, depending whether or not you regularly publish information for that list would have had a lot to do with your resources.

And here’s where I have to, I have to caveat some of this, which is, uh, by saying, I’ll, you know, my research was sort of specifically on these seven figure plus media companies. Um, so this may be different depending on who you’re talking to, but what I can talk about is like, I can talk about the levers that are at play here so that you can decide for yourself which ones to pull.

Um, you can and probably should continue growing the free newsletter or the free email list. And that can be as simple as having, you know, a lead magnet on a landing page that says, you know, download like the five best interviews that we did with people in this industry, or something like that. Uh, reason for that is that free list becomes distribution for your paid community, and not everyone is gonna opt into that immediately, but creating each of these things, what I’ve seen, at least being on the backside of it, they’re incredibly resource intense.

Like to publish a free a newsletter, and I think this is where actually a lot of sub stackers struggle is. It’s hard, it’s a lot of work, and you have to, if you’re going to do that and offer a paid product, the paid product has to be sufficiently different and more valuable than the free content in order to get people to sign up for it.

I think the value, this is just my personal opinion, the value that you’re talking about now in terms of, uh, speaking to a very specific industry that you like, this is these people’s livelihoods. Um, there’s enough value tied up in that on its own that if I ran this business, I would be willing to pay for this, no questions asked.

You know, and again, this is where the pricing on front versus backend comes into play. Uh, that’s a, that’s an opinion, that’s a hypothesis. You’d have to test it, but I think all things considered, you could start this sooner rather than later. You wouldn’t need a large distribution list in order to monetize this at a, at a pretty reasonable rate.

I mean, uh, That’s kinda my initial thought on that. The other thing related to this is, is just what I mentioned a minute ago too, which is I, I think there’s a lot of value tied up. Like, this community is struggling and they’re kind of waiting for somebody to come help ’em. So to whatever degree that you can or that you’re interested 

Ismail: in, and I say go for it.

It’s interesting you mentioned that because I noticed, um, there’s like a leadership vacuum now. Like there was all these people, um, industry leaders happily leading when times were good and now I guess they’re all struggling as well and there’s like a vacuum there. There’s not a lot of people still putting out helpful information.

Just a couple resistance things I’ll just throw out randomly. Um, I feel like

[00:56:13] Making more money from company vs. Subscribers.

Ismail: in the industry it’s a lot easier to get the companies that cater to the industry to pay me based on my experience with the, the event versus getting the actual boosters to pay me. I’m not saying that they’re cheap, but I just realized that it was a lot, it was surprisingly easy to get the companies to give me.

Substantial amount of money, um, in exchange to reaching the audience. So that makes me think, Hey, maybe I should just grow a free newsletter as big as possible, and I’ll make money, Maybe I’ll make more money or more easily from the companies versus, um, subscribers. And the other point I’m forgetting, so let me stop there and see if you have any reaction to that

Ethan: Sure. Well, uh, you could certainly be right. And this is, this is, this is where, uh, the business model becomes important. Like I said a couple of minutes ago saying, you know, when you understand how these things interact with each other, you’re free to decide for yourself. The reality is, I mentioned there’s these three different ways to monetize.

And if you look at media companies across the spectrum, uh, lots of them use different combinations of this. So, as an example, um,

the, the hustle. Before, if we had published this backend newsletter product, we would’ve had all three. So we had the front end, which is the free daily email. We have trends, which is, uh, or sorry, we have the free email, which is the daily email. We have trends, which is the front end, and then these high price reports would’ve been the back end.

You have James Altar, who has, again, his like altar report, which is the free email. He’s got front end and backend products that range, you know, a couple hundred to a, a few thousand dollars. You have the New York Times, who has only, uh, free newsletter and front end newsletters. They have no backend products or you have, uh, different examples like, um, oh, like, uh, what’s his name?

Van Trump. So Van Trump writes an agricultural newsletter for, for like people in commodities markets, and I’m pretty sure they’re only publishing backend. Uh, you, the way they get people in is on like a free trial. So, There’s actually no one way to skin this cat. If you understand how the different monetization strategies work, you can mix and match them how you like.

And to your point, um, it may be that growing the initial list is good enough for what you’re trying to build. Uh, you’re Tim Ferris fan. You remember when he experimented last year or maybe two years ago with switching from ads on the podcast to this like listener supported model. And what he found was that actually selling ads was more, uh, profitable and took less work.

So, uh, if, if that’s the direction that you want to go, it’s certainly an opportunity, uh, given how niche the industry is. I, I would actually leave the decision to you, cause I, I, um, at least the. The people that I’ve interviewed have required larger lists for that kind of advertising. But I, again, this is, yeah, very domain specific.

Ismail: No, you, you’ve mentioned

[00:59:16] Different monetization Models.

Ismail: so many interesting points. Like, uh, I didn’t consider that it would be a lot of work putting together the free one and a paid one if I went that route. Um, I do feel like getting a few hundred bucks a month for, for an ad would be very easy. Um, but getting a few hundred people to pay a hundred bucks a year would be difficult.

So I think what I have to think about or experiment with is, do I want to go the route that you mentioned straight to a paid offering and build a community? Cause I had the idea to do that with my, um, the course platform that I built to create like a monthly subscription, uh, where you’re connect, you’re, you’re in a community with these like-minded entrepreneurs in the same industry, and you have like these recurring calls or to go the route of build a free, um, monthly newsletter and monetize that.

Maybe I don’t care as much about the a hundred dollars a year because I have all these other ways to monetize it maybe. And it, the bar for quality for a free newsletter would be a lot easier for me to not have to be like, stress about, Oh my God, is this worth what they’re paying me? Will they cancel yada y?

So as I’m talking it through, I feel like it would be less stressful and easier to do the free newsletter because I have the other backend stuff that I know, uh, would, would benefit from that no matter what does 

Ethan: that. Yep. And you’re bringing up another great point, which is important for people, uh, listening to understand, which is that these different monetization strategies offer it.

They, they offer benefits outside of how much money you can earn. So, um, if you have a free newsletter and you’re monetizing ’em via ads, that’s great. Some people will ask, Okay, well should I create a paid newsletter in order to make more money? And the reality is like, or actually what people will ask is, should I create free or paid, right.

Which one’s gonna be better for my business? And what we found is that actually, you know, in the long term the answer is you wanna create both. And the reason is, having these different monetization models actually protects your business from the ups and downs of the markets. It also, uh, helps to increase the lifetime value of the people that are reading that newsletter.

So in your case, if you have people, and again, part of my answer is I got a caveat cuz I never talked to anybody in such a niche industry. But if you have people who are willing to pay you good money to reach a thousand newsletter booth operators, that’s great. I mean, start there, like you said, it could be a great place to start.

The thing to think about at scale is if you sell. Say a hundred thousand dollars worth of ads this year, and you, uh, that’s great. Come next year, in order to make that same money, you gotta go out and sell those, that exact same number of ads again. And so this is where the paid subscriptions become really cool for anybody who’s looking at this because, uh, they, they drive recurring revenue.

And, uh, even so, like, let’s say you sell a hundred thousand dollars worth of subscriptions, if half of those people renew the following year, you kick off the next year with 50 grand in the bank. And even if you only sell the same amount, another a hundred thousand, your business is grown by 50%. So, um, and I’m sure you can link to it in the podcast notes for this.

I’ve weighed some of this out visually, but this was like, this was so important. The only reason the New York Times is still alive is because they switched to primarily paid subscription revenue, uh, as opposed to. They were primarily ad driven for a long time. So blending these business models can help you ride sort of the, the peaks and troughs of this industry.

Um, but if you understand how the monetization works, you can make this decision for yourself. The last thing I’ll say, given the size of your newsletter in particular, and I think this goes for a lot of people listening to this because you mentioned that, uh, a lot of people in here are pursuing these niches, which I love.

I mean, we may have to rewrite sort of the way these are approached because it’s so new. Um, but one newsletter to look at or I’d say one or two. One is the Ferrari market letter. So Ferrari market letter has something like 5,000 subscribers and they’re doing, we estimated about $2 million a year in business and they do this.

Through the subscription fees, but also through sort of these add-on products, which you’ve kind of mentioned versions of yourself. So it’s not all tied up in the newsletter, but the newsletter can be a primary, uh, revenue driver. Um, 

Ismail: go on. I was gonna say that that’s a great, I saw that in one of your, one of your, uh, tweets.

It’s a great niche because, uh, it’s an expensive product and even if people don’t buy that product, the people that are interested in learning about it have higher income. Right. So it would be easier to monetize and sell products to them, I think because of that reason. Um, and I’ll challenge myself, like my list is entrepreneurs, like business owners, they sh it should fall into the same kind of category.

If you can give them value, um, they should be able to, uh, afford it. Um, if it’s something worth of value. I, I, I guess I’m stuck and I think I decided this while speaking with you. Um, I may be wrong and you, you may disagree with me, but I think because of all the backend opportunities that I have, um, that I’m already doing, I think the free route would benefit me more and it would be peace of mind where I wouldn’t have to stress about the, That’s another thing too.

It’s like, Oh my God, I gotta really make this monthly newsletter Amazing. Not that you wouldn’t, but it, it’s a, it’s a little bit of a lower bar when it’s free. And I think, um, I’m leaning towards that route because it would help all the other ventures that I have, and that’s probably the priority to me if I had to pick one.

[01:05:07] Email newsletter frequency.

Ismail: Do you think a monthly is frequent enough? Like you mentioned daily, like I know a lot of guys like Anthony Pomp, they do like daily newsletters every morning. That’s a lot. And it’s a free newsletter. He’s doing it for me. Yeah. So Right. How often, how frequent should these things be? 

Ethan: That’s a great question and, and I’ll, I’ll pause just briefly to touch on what you said there before the question.

You, you, you could absolutely be right. And if that’s the direction that you wanna go, I, I completely, uh, encourage it. I hope for anybody listening to this understanding how these different levers can be pulled makes this decision easier for you too. I mean, there’s, there’s, we said it before. There’s no right or wrong way to do this, but when you understand it, you can make the decision better for yourself.

Um, the one other thing I’ll, I’ll just suggest, which strikes me is that the, uh, the nature of this podcast is fairly wide ranging. And so there may be some opportunity there to let the free newsletter go a little more broad, even just slightly to like other areas of event specialization, um, which leaves this opportunity for the hyper niche paid content in the future.

If you wanted it, it’s something to think about. But if, if the, uh, there you highlighted a lot of great reasons to start. Free and I’m, I’m glad to hear that there was like some clarity, uh, you got some extra clarity there. Uh, to your question about frequency, that’s a tough one. You know, I interviewed Sam Par about this and he said he noticed that, uh, the more often he sent an email, the higher the open rates went.

And this was back when the hustle was just starting out. So, you know, people have a different kind of relationship to email now, but I’ve seen a few things, uh, which are worth noting. So

there are a lot of people who will say that frequency and even consistency are secondary. If you’re writing stuff that your audience loves. Because what you’re really need to get them to do is open the email. And one of the biggest things that contributes to open rates, it’s actually not your subject line, it’s, it’s the, the front line.

And they see the name that comes into their inbox. Do they, do they care? Do they archive it or do they, do they, do they open it? Um, is there, actually, I’m curious to know, is there like an email that you op that you read every single one and uh, don’t say like, don’t say the hustle, but like, is there for me it’s huckberry.

I read every huckberry email that comes into my inbox cuz I love the photos. Is there anything like that for you? I, I, 

Ismail: I’ll answer that, but before I say that, I actually had like very people I really respect recommend trends to me. Like the first person I interviewed for the show is the CEO of Snap Bar, which is like the, one of the rare photo with companies in the, in 500.

And I dunno if you, if you, if you come across them, but he was like, I think you really like this trends thing. Check them out. Um, so it’s funny that it kind of came first full circle on what we’re talking here. Um, , I would say, And this guy follows you on Twitter, so that, that counts for a lot of points to me.

But Ramit safety, I really, I’m a big fan of Ramit safety, so I’ve, I’ve read all his stuff for a long, like years, and I’ve, I’ve sent him messages. He’s responded to them a few times. Um, so I, I would name him 

Ethan: and, Okay. And so whenever you see Ramit’s email in your inbox, like you’ll open it. That’s the one that comes to mind.

That’s what I’ll open. Yeah. Okay. And do you know, just, I mean, I, I don’t know the answer to this. How often does he email? A lot? 

Ismail: Every day. Sometimes multiple times a day. Yeah. 

Ethan: If you didn’t hear from him from a couple of weeks, would you still open his email? If I came in? I think so. 

Ismail: I think I would. Okay.

There’s, there’s already like years of, uh, relationship built there, so I’d opened it and I bought some of his stuff and bought his book and all the other things. So 

Ethan: I, I, I, I, I, That makes sense to me. And I think that mirrors what I’ve heard elsewhere, so I can’t unfortunately give you. A concrete answer on this.

Cause I see so many, uh, conflicting opinions, but from what I heard, if you have a really great relationship with your audience and you’re creating something that they care about and they know your name and it comes into their inbox, they want us, which you have to say, I think you can kind of set your own frequency.

And, um, there are a lot of newsletters specifically in the financial space that are on a monthly cadence, and they do quite well. 

Ismail: It’s, it’s really interesting that you mentioned the name. I’d never thought of that, but like, all these different backend things that I have are like separate businesses almost.

It’s the conference, it’s the software. But I always made sure that no matter where the email came from, the from was just my name, it was Ismail. That’s a unique name. And I think over years of like selling them stuff or being on the podcast or whatever, um, I, I think I have a pretty good, decent open radar.

Like the list is doing well, so people see the name. I did that accidentally. Look at it. I, I got lucky with a lot of stuff. , 

Ethan: you and me both, man. Just kind of bing my way through this, this thing we call life. Um, yeah, I think the only thing, there’s one thing to, uh, to consider as well, which is if you’re going to go the free route and you’re going to monetize it with ads, that is to some extent a volume game.

So it, it, it depends on how much you wanna make from this newsletter. I can, I might be able to get into some specifics here that could be useful for the listeners if you like. Let’s 

Ismail: do it. Okay. But I, I think one, one quick thing is I thought the same thing. If you only have a monthly newsletter, it’s only 12 opportunities to have ads.

It limits how much you can make. You can’t charge a crazy number per ad cuz they won’t get an roi. So Yeah, totally. Totally right. But go ahead. This 

Ethan: is exactly why. So there, there, there are three levers at play in selling advertising and uh, in order to. To monetize a free newsletter, you need at least two of the three.

Uh, so they are the, the size of your audience. So you need a big audience. You need an audience that’s willing to spend money, and you need, uh, an engaged audience. And the figures on those are like big audience. I would consider that everything from 75 K upwards, uh, willing to spend money, that kind of changes depending on the industry.

But engagement rates of like 20, 30, 40%, those are all like incredibly high. 20% or more on your open rates is going pretty good. Um, if you have two of those three, you’re ready to monetize a free newsletter and, uh, you can see how they sort of interact with each other. The re by the way, the reason your au you need an audience that’s willing to spend money is because the way for anybody listening, the way your advertisers, the way you price ads is based on what the value of your reader is.

To the advertiser. And so one of really common questions like what should my ad rates be, which my CPMs be? And unfortunately there’s just no good answer. It would be great if there was like an industry standard, but there’s not. It turns out, uh, the best answer is like, well, for the general type of advertiser that you bring into your newsletter, how much do they earn off of one of your readers?

If, if a reader of yours becomes a client of theirs, what is that? Uh, lifetime value? You work backwards from there to figure out what your ad rates are. The cool story that I heard about this was from the Hustle when the first like major advertiser this company landed, uh, was Microsoft. And Microsoft came in with, you know, a preset ad rate and our guys were able to show them that they, like by advertising with us, they were talking specifically to the types of people that they wanted to reach.

And I think they ended up spending something like five or six times, whatever their initial. Ad rate was, then they came back six months later when the email had really kind of continued to snowball and they paid even more. So these are very fluid things and, and, uh, there’s not like a, a sheet somewhere where you can just see what the price is, But if you know these, uh, factors, you can help, uh, make a decision for yourself.

So, large audience, audience that’s willing to spend money, highly engaged audience, you have two of those three. You are probably going to be, uh, you have, you have what you need to make it a success at, uh, monetizing a free newsletter. So in the case of like a, a monthly email, where that becomes difficult obviously is you’d have to have either an enormous audience that’s incredibly engaged or like, or like willing to spend a ton of money.

That’s why Ferrari Market, uh, can do so well is because, you know, that’s a, that’s an audience that is going to spend like thousands of dollars if, if they buy a Ferrari that somebody’s advertising. So, uh, With those in mind, if you’re thinking about continuing to go the free route, uh, you may want to sort of use those, uh, criteria in deciding how often you send or, or what you charge.

Um, there’s also different types of ad inventory and uh, I won’t get into those yet unless you want to. But the, the last thing I’ll say for anybody listening to this, because we are talking specifically about niches, uh, affiliate marketing can be a great way to monetize a hyper niche newsletter. So I don’t know if that exists.

I mean, you mentioned that there are these different, like booth op, 

Ismail: Uh, Yeah, there, I mean there’s companies that sell booth and equipment that are, you know, ranging from a thousand to $10,000 plus. So I think a customer would be very valuable. I know that a customer would be very valuable to them and they’d be willing to pay for it.

Cuz I’ve, I’ve sold them ads for the podcast. I’ve sold them space at the conferences. So, uh, that part I’m more comfortable with because, like you said, it’s such a niche that no one else has the audience in one place. Right. Before I forget, I’m sorry, this is one question I had before. 

[01:14:49] Why would people pay for an exclusive community?

Ismail: When you’re talking about the community, um, what about the, the, um, the hiccup people have?

Oh, there’s already Facebook groups. Oh, there’s already these forums. Oh, there’s already these communities already there. Why would they pay to be in my community? It’s already on Facebook. 

Ethan: Oh, that’s a great question. I mean, I think the simple answer is a, anybody who feels that way, probably in a great, uh, customer for, for these particular products, and you know, we touched on this earlier too, like there’s, there’s a certain group out there, the group that will pay for this, that looks to these groups, not just for what they’re providing, but for the curation that they provide as well.

So in the case of trends, you know, it’s expensive. It’s three, it’s not incredibly expensive, but it’s like three or $400 a year. And what you end up getting inside that group, because there is that initial barrier to entry is you get a group of people who are much more committed to being there and to like acting on the information or to engaging with the community then you would if it was free.

And, and we know that for a fact. Um, so I, I do, there are definitely people who. Won’t pay. There are people who won’t pay for your ads because they can target people more easily on Facebook. But I think it’s about finding the people who do see the value and, and, and like really making sure the value is there.

And it certainly is if you’re curating a group this specific for any industry, whether it’s, uh, this or, or another. I, 

Ismail: I could grill you for hours on this. I think. Um, I, I found that someone that finds these things as interesting as I do. But I think one, one thing that I’d love, I as advised to you, I feel like you might get way more attention talking about, I guess I’ll just refer to it as like these micro newsletter opportunities.

I think people find a more relatable, It may not be as interesting for you cuz you’re, you’re more working. From the big media angle, uh, with the hustle and and whatnot. But there’s a lot of people out there that can make a good living with an email of a thousand, 5,000, 10,000 people, and it’s way more doable.

I haven’t seen anyone really, um, organizing content around that specifically. So if I know you went over time, I, if you have a couple minutes, I just appreciate 

[01:17:03] Strategy for creating value for customers.

Ismail: you talking a little bit about, like, let’s say the people listening, it’s a huge range. Let’s say it’s a photo booth operator and they have a client list of people that book them for events every year of event planners that use them, uh, or yoga, A person that sells yoga products.

So they’ve got a list of people that like yoga. Does it make sense for these companies and the people see this all the time where companies try to create their own newsletter for their lists? Does that make sense? Or do you, are you not really well informed about that area? Cause it seems like people try and get, like, even in my industry, a lot of these vendors have an email list, but it’s like, Hey, buy this product.

Hey, buy this product. Should these people create more value add. email list for their small client list or their lead list? 

Ethan: That’s a great question. Um, well I’m biased cuz I work for a newsletter company and so you ask a guy with a hammer what the solution is, he’s always gonna say or what is that hammer 

Ismail: Exactly say the hammer.

Ethan: Yeah. What I have seen, I can tell you this, if you, first of all, and I mentioned this in the beginning, I love what you’re building because it’s so niche and there are examples, like I said, of uh, people who generate enormous amounts of revenue on, on relatively small lists. So the Ferrari market is one, um, uh, Kevin Van Trump is another.

They do about, I think they do, it’s like 3 million bucks a year on a newsletter. Farming and there’s a whole bunch more. I mean, this is like the type of research we do over at trends. We’re always pulling out these niches that have all kinds of opportunities. I was just, I just wrote an article today about, uh, the truck accessory market and how, you know those to covers for trucks.

Yep. Okay. Well, that entire industry is dominated by one player. There’s 16 brands in the entire industry in North America. 11 of them are owned by one company, and so they have 90% of the market share, but they cater to this unbelievably active user base of people who wanna modify their trucks. And, you know, I don’t, there’s like, there’s like 20 million pickup trucks on the road in the US and we sell three to 5 million more every single year.

So it’s an enormous potential reach. Not a lot of people really pursuing it. Right? Cause it’s not this sexy like morning brew kind of, uh, Tech business space. So there’s, I think there’s enormous opportunity in niches. There’s an enormous opportunity in building a closer relationship with the clients you already have.

And it’s easy to screw it up if, if, if you are just being transactional about it. So, should you start a newsletter? That’s a great question. I think it’s like, you know, what, what do you want to, what do you wanna say? If it’s just about, uh, moving the most recent product, don’t, I don’t know, maybe don’t bother with a newsletter because email lists have been successful at that forever.

But what I will say is that if you have like an authentic voice and kind of you have a take on this particular space that you wanna share, there’s unprecedented opportunity to make a great living doing it right now. So, 

Ismail: Um, with my example, you

[01:20:22] The Newsletter Opportunity.

Ismail: , you touched on it and it made me smirk because I, I started the, I basically started this podcast, um, as a way to branch out of just the photo booth industry.

It just so happened a lot of people followed me over from there. Um, do you see any opportunity specifically, this is way broader, it’s more business oriented, uh, finance, et cetera, an opportunity here to start a newsletter, or is it just so saturated and so like, what would you do or would you begin, how do you get your first thousand people?

It seems like it’s a lot harder when you’re not in a specific niche. 

Ethan: Everybody, Ismail started a newsletter, so sign up for it. Like, what’s beautiful about what you’ve done here is like you have built in distribution, right? Um, and so yeah, there’s, there’s definitely opportunity here. The thing is, um,

I hate to sound like a broken record, but I, I keep coming back to that business model. We call it the newsletter engine, which is like, there are three different ways to monetize and if you sort of understand how they work, you can see where your idea fits into it. So in this case, we should talk about here is a little broader and I think it helps to fit that, uh, notion that I was talking about where companies cast kind of like a broad net with whatever their free product is.

And maybe, I mean, now that we’re talking about this in just kind of spitballing, maybe it’s not about creating a free newsletter for photo booth people. Maybe this is the free distribution, right? And the photo booth thing is one step more specific. I don’t know. You have to have to to make that decision, but um,

As with any business, The, the, the, the tricky thing is like, how do you really, how do you win space in somebody’s head? And I think what’s great about your photo booth niche and what, what a lot of your listeners are working on is that it’s so specific. It’s, it’s memorable and there’s not a lot of people that are operating in that space.

You know, Sam’s got this thing right now where he says he thinks newsletters are dead. And what I think what he is, I won’t put words in his mouth or I don’t wanna put words in his mouth, but I will, he, what he’s sort of saying is like the big general business media, that fight has largely been won for now.

It’ll be shaken up again in a few years. Right. But just the same way everybody used to pay attention to like Forbes and Business Insider and all these people, and now they’ve sort of slipped to the wayside behind pod a handful of podcasts, a handful of newsletters that fight. Around every once in a while as these new mediums emerge, but for now, it’s very hard to stand out and capture market share from these people.

Uh, so the question people have to ask themselves if they’re, if they’re gonna get into this, is like, what makes you different? And I, that’s probably a basic question for a lot of your listeners since they are familiar with this space. But, um, I, yeah, I think, uh, I think the, the, the niches are where the most opportunity is right now, and what’s unique about the time that we’re in is that you can monetize those niches in a way that wasn’t possible 10 years ago.

Ismail: One, one last thing I’ll ask you is, um, 

[01:23:39] Advice to Tim Ferriss to manage his bulk email lists.

Ismail: we we’re both Tim Ferris fans, um, I’m, I’m guessing you’re on this email list and you see the five bullet Friday email list that he sends out. I’m gonna take out the snippet of this podcast, post it on social media and tag Tim Ferris , No pressure, but what, what advice would you give him?

Uh, cuz I find it so interesting that it’s such a simple email, um, but you kind of look forward to it. Like I al that’s another one that I always open and most of the time I don’t really get anything new out of it. I kind of skim through the five things, but I feel like I have to ski through the five things like I have to.

So is there any advice that you’d give Tim Ferris on his, how to utilize his large list better? 

Ethan: Oh my God, . Um, so no, and I’ll tell you why. , first of all, the reason is because, but is because I think actually Tim is leading the pack there. Uh, so what I will say is I, I won’t give Tim any advice. Would, I wouldn’t, I wouldn’t suppose to do that.

But I will say that I think people can learn a lot from what he did. When Tim Ferriss launched that newsletter, the idea of five short bullets in an email was. Everybody was publishing long form newsletters and what, you know, I, I’ve observed, and I’ve never actually deconstructed his newsletter, so it would be interesting to go and do it.

But what I’ve observed, just being a listener of his content was that he, he spoke to a lot of people. He talked to Ramit back when he first watched that, and, you know, he captured email addresses passively on his website for years before he ever decided to make a go at that. Uh, he was willing to try something that was new that a lot of people weren’t doing that had value in it, even though it wasn’t popular.

And I think more people could learn from that. Like, don’t, don’t be so worried about what everybody’s doing right now. Like everyone’s, everyone’s chasing these massive business markets, but you know what nobody’s talking about, like nobody’s talking about how do you actually take time off? As an entrepreneur, everyone’s talking about like hustle and grind and success and all this bullshit, but like how do you actually go, um, you know, strike that work life balance as a, as a brand new parent.

Like what are the real struggles there? I think there’s a lot of value tied up in the things that people are too afraid to try. And in case of, Tim, I’m just kind of guessing here, A lot of people would’ve been very hesitant to try five quick bullets once a week. Um, but we, we could all probably learn from that.

Ismail: You know, what’s fascinating about that is he’s been inspirational to me with, with this podcast where he’s a big believer in long form content. I think he’s put out content about this where, um, It’s easier, there’s less competition. A lot of people don’t bother doing the long form size. Podcasts are in depth.

His blog posts are in depth. But on the email, he went the total opposite route where he went really short form content. Uh, I don’t, You’re right. There’s something to take away from there. I think he, he’s always willing to experiment, but that stands out to me as like, it’s, it’s hard to be that kind of open minded person where you do everything long, everything long firm.

But this one, I think it makes sense to do this a little differently. Let’s see what happens. I think you’re right. There’s something to learn there for sure. 

Ethan: Yeah. The universal, the thing that ties in together is what are people not doing? Hm. Like when you launched a podcast, I think Joe Rogan was the only one who was doing anything close to a three hour podcast, and Tim’s are consistently two, three hours plus.

So go where the people aren’t going, instead of trying to do what everybody else is doing and just take with you this knowledge of like, how these business models working. You will kill it. I mean, it’s, it’s, this is proven now. The business model is verified. So if, if you execute well, uh, there’s a lot of opportunity.

That’s all I would say to people. 

Ismail: One, one last question that I ask everybody. Um, 

[01:27:36] Any hint of a future successful entrepreneur as a young kid.

Ismail: it’s The Bound to the Rich podcast. Um, without going to the full story behind the name, it’s basically identifying people that seem destined to be successful. So when I speak to someone like you who’s successful, you helped lead like a massive, um, newsletter, company, media company, whatever, it’s qualified as.

Now, if I talk to people that knew you, like back in high school, Friends, family, teachers, classmates, Would they be surprised to see where you are now? Or would they be like, Oh, that kid Ethan, man, he always, he was always a little different

Ethan: Wow. That’s a good question. I, I, uh, I would they be surprised? They would probably be surprised. I mean, I’m surprised , I, uh, I, I, they would probably say I was always a little different. But that’s the only, like, everyone’s different in their own way. Um, what, I’ll tell you what I’m surprised by. When I was young, I told you my first love was always writing and I never thought there was a way to make money at it.

And so I, I spent a long time building a career around other skills that I had kind of developed that, that were. Monetizable. And so to whatever extent people would be surprised, I think it’s that this industry exists now and that I was able to like, not just me, but like it’s possible to make a living as a writer.

That’s, that still surprises me. And, uh, I joke about this all the time. I’m like, I can’t believe my job is a real job. I, every day I’m afraid Sam is gonna show up at my door and ask for all his money back because this, like, he just figured out this is not a real job. Like this is, this isn’t a real, this is just fun

Um, so to me, I, I still pinch myself in that way. I can’t, I can’t speak to anybody else, but who knows what they would say. I, uh, I deny it all. . 

Ismail: Ha. Have you,

[01:29:33] Learning from Sam.

Ismail: have you picked up on any advice from Sam on, uh, growing podcasts? They, their first million podcast is amazing. So anything that you’ve picked up from him about advice that you give?


Ethan: not advice. I love Mike Rose as advice is the thing we ask for when we know the answer and wish we didn’t. I hate giving advice, but I will tell you I’ve learned a ton from Sam. He’s like an in, he’s such an interesting guy. Uh, there’s like two or three that always come to mind. The biggest one with him, I think is like the ability to cause mischief.

Like he’s a very, um, anybody who knows Sam knows that he cares about people a lot. Like he’s actually very, um, empathetic, which is rare among startup founders. And at least my take is that he, like, he genuinely cares about people, but he’s also a little bit of a troublemaker. And so he does these things online that stir people up in order to kind of get attention or to get a rise out of people and, and it’s helped to grow.

I mean, everything from day one. The way they grew the hustle was by writing these like super controversial pieces that he knew were going to piss off half the people who read them. And the thing he told me is he said, Those are the people I knew. Were gonna share it. The people who, you know, get riled up about, they knew all you’re sharing for you.

And so he very specifically, like I I say, it’s like a kind of coyote trickster creates a little bit of like well-intentioned mayhem. And, um, that’s something that I’ve started to take from him. I, I, I tend to be a little bit more kind of collected, but he’s good at it. Like, one of the things he did recently just in terms of like specifically growing the podcast is, uh, maybe you saw it, he tweeted it was a screenshot of the apple, like, subscribe.

And he just tweeted. He’s like, Oh my God, this is the craziest thing. You’ve gotta see what happens when you click this. I can’t even believe they let the engineers put this feature out. Whoever published this, like my hat goes off to you, like just this over the top post. And you’re looking at it and you’re like, I bet nothing happens, but I probably gotta see.

And like, you know, it’s shit like that. So that’s one. But to give you a more, um, concrete answer, I asked him what was the most surprising thing about running like a successful media company? What did you not expect? And he said two things. He said, One, it’s really hard to get the entire team moving in the same direction.

Like that is way harder than most people think it is. And it ends up being a big chunk of your job once the company becomes successful. The other thing is that it is really hard once you’re successful to get people to take risks. And that stuck with me because. Up until that point, I don’t think I ever considered that my job was to take risks here or anywhere else.

It’s just not how I take, I typically think about these things, but he’s, you know, he is wired a little different and he kind of, I think he understands well what is required in order to get a lot of attention in order to like, make things successful. You have to try things that other people aren’t doing.

And this ties in with what we were talking about earlier. So that’s something that I’ll probably always remember from him and I, and just the last thing, uh, is ties back to what I said about him being like an, an empath. I’ve worked in startups for more than a decade, and I’ll tell you like everybody, you know, especially you’ve been on Wall Street, you’ve probably seen the same thing.

There are a lot of assholes in this industry and it’ll burn you out. , but everybody listening, I would say, don’t ever let yourself believe that everybody is like crooked or everybody is, is a jerk because it’s not true. There are great leaders out there who are empathetic, who care about people who know how to build a successful company without like people.

And my experience with Sam has been that that’s, that’s, that’s who he is. It’s something that I admire a lot, something I’m, I’m hoping to take with me, uh, moving forward. But that’s, that’s kind of what I’ve found just working with him. That’s 

Ismail: awesome. That’s a lot more advice than I was hoping for, so I’m, I’m glad that I asked you that question.

Just one quick thing I touch on that you said the creating the mis shift and, and then a little bit of the, the like ruffling some feathers. That’s how I got viral on TikTok. I created a video that was like an extreme example of how to build wealth and people got, they loved it or they got very, like, people were either offering me money to do it for them or they were very upset at me.

And I have this strategy called, I don’t know if it’s something out there, I just do it myself. I engage the trolls. So every, everyone that wrote a mean comment, I was going back at it with them because , that, that boosts you in the algorithm. They come back, you get more comments, you get more watches. They tag.

I had one guy who tagged another account, uh, of someone that had millions of followers and it was like a personal finance guru, and he’s like, Oh, look at this video. You’ll get a good laugh out of it. And I went back and forth with him a few times and now I’m interviewing the guy next week with Joan to follow.

So I can’t wait to take that clip, put it back in there and thank the guy that was trolling me for the introduction. So , 

Ethan: um, that’s awesome. , 

Ismail: Nathan, man, I appreciate you so much. I,

[01:35:08] Thank You & Wrap up!

Ismail: I thank you for going above and beyond with the time and being generous with that. I really enjoyed speaking with you. I, I, I had high expectations, but I’m really glad we got a chance to connect and I hope it’s not the last time we do, uh, you’re someone.

That deserves way more followers on Twitter than what you have already, which is already way more than me. But you still deserve a lot more. So I’m gonna obviously tag everything in in the the show notes. I’ll put a select few threats that had an impact on me and maybe some ones that you touched on for everyone to check out.

And otherwise, I highly recommend they follow you. Is there anything that you else, that you 

Ethan: point them to? . Um, no, I think we covered it, man. I just want to say thanks for the invite. This was a lot of fun and I, I don’t say this to everybody. You’re fantastic at this. Thanks. It’s very easy to do the conversation, so, uh, thank you for having me on everybody.

Thank you for listening and, uh, I, I had a blast. Thank you. Appreciate it, man. 

Ismail: Thank you so much.

One quick reminder before I let go to join my email newsletter, it’s gonna be like a personal note for me to my friends. Of all the cool things that have come across that morning from hacks and tips, interesting stories, products, books, was to make money and who knows what else? It’s totally free and if you don’t like it, you can always opt out anytime.

The link to join is in the show notes and I hope to see you in the list. And there you have it. If you enjoy this episode, please remember to leave a review. I may even give you a shout out and read yours out on the show for any and all resources that we discussed. Check out the show notes or head on over to bound to be

Until next time.[/expand]