Dave Pell has been writing online for almost as long as the internet has existed. His popular newsletter NextDraft has over 140,000 subscribers. NextDraft covers the day’s ten most fascinating news stories, delivered with a fast and pithy wit.
Dave has been a syndicated writer on NPR, Gizmodo, Forbes, and Huffington Post. He earned his bachelor’s degree in English from U.C. Berkeley, and his master’s in education from Harvard.
Besides being a prolific writer, Dave is also the Managing Partner at Arba, LLC. For more than a decade Arba has been angel investing in companies like Open Table, GrubHub, Marin Software, Hotel Tonight, Joyus, and Liftopia.
In this episode, you’ll learn:
- How Dave merged his two writing passions into a successful product
- The key to building a strong relationship with your audience
- How Dave dramatically increased signups to NextDraft
Links & Resources
Dave Pell’s Links
- Dave Pell on Twitter
- NextDraft newsletter
- Dave’s new book: Please Scream Inside Your Heart
- NextDraft app
If you have something to say in one way or another, the internet is a great place for people to figure out a way to receive it. So, that’s pretty powerful and still excites me. I still press publish with the same enthusiasm now than I did when the internet first launched.
In this episode I talk to Dave Pell, who has been writing for basically as long as the internet has been around. He’s been an investor since the early days. He’s been writing since the.com bust, and even before then. He writes his popular newsletter with 140,000 subscribers called Next Draft.
We have this really fun conversation about writing. His writing process. How he grew the newsletter. Bunch of other things that he cares about. Even a few things that I was interested in, like he doesn’t have his face in photos on the internet very much. He has his avatar instead. So, just getting into why that is.
He also has a book coming out soon. It’s called Scream Inside Your Heart, which is a fun reference to some memes from 2020. So, enjoy the episode. There’s a lot in there.
Dave. Welcome to the show.
Thanks a lot for having me on.
Okay. So you’ve been doing this for a long time. You’ve been writing on the internet since the .com era. So, I’m curious maybe just to kick things off, what have you seen—I realize this is a giant question.
What have you seen change? What are some of those trends that you’ve seen, that you either really miss from the early days, or some of those things that you’ve held onto from the early days of the internet, that you’re really still enjoying?
Yeah, that is a pretty huge question, but I’ll give it a shot. The thing I miss from the early days of the internet is that our democracy was not being destroyed by the internet in the early days of the internet. So, everything we thought we were building, basically it turned out to be the opposite of what actually happened.
The part about the internet that I still feel is there, although a little bit less so because of the big companies have sort of taken over all the platforms and stuff, is just the idea that someone can have a passion or a creative output that they want to share with the world, and they can mold internet tools to fit their skills, and then use the internet to broadcast that out, and still become sort of pretty popular withour the “OK” of some gatekeeper at a publication, or at a television studio, or whatever.
The indie spirit of the internet still lives on. It ebbs and flows, and has a lot of different iterations. But that was the thing that excited me the most when I first played with the internet. And that’s the thing that continues to excite me the most now.
I always think of the newsletter, and your newsletter in particular, is that indie spirit. Is that what you see most commonly in newsletters? Or are you seeing it in other places as well?
I see it in podcasts. I see it in newsletters. I see it in people sharing their art, sharing their photography on Flicker, and up through the more modern tools. I go to a site called Unsplash all the time to look at images, and it’s just basically regular people sharing their images.
Some of them are professional photographers, some aren’t, and they’re getting their work out there, and then some of them probably get jobs out of it and stuff like that. So, just the idea that you can have some kind of creative output and have a place to share it. And try to get an audience for that is really inspiring.
It’s a lot harder than it used to be because there’s a few billion more people trying to get attention also, and because there are more gatekeepers now. So, you have to, hope that your app meets Apple’s guidelines, or that different products you might want to share on the internet have to meet certain classifications now, whereas they might not have in the very early days of the internet. But in general, if you have something to say in one way or another, the internet is a great place for people to figure out a way to receive it.
So, that’s pretty powerful, and, still excites me. I still press published with the same enthusiasm now that I did when the internet first launched.
Yeah. So let’s talk about the main project that you have right now, which is Next Draft. Give listeners the 30-second pitch on Next Draft, of what it is.
Sure. Basically I call myself the managing editor of the internet. What I basically do is a personality-driven news newsletter where I cover the day’s most fascinating news. I cover 10 stories. A lot of times in each section there’s more than one link. I give my take on the day’s news, each individual story, and then I link off to the source for the full story.
When I first launched it, I called it Dinner Party Prep. I provided enough information for you to sort of get the gist of the story. And if there’s topics you want to dig deeper, you just click and, you know, go get the story yourself. So that’s sort of the overview of it.
Nice. And you said that you’re obsessed with the news maybe in a somewhat, even unhealthy way. why, where did that come from?
Yeah. Well, nothing, nothing about my relationship with the internet is only somewhat unhealthy. it’s all extremely unhealthy, but, both my parents are Holocaust survivors and, when I was growing up, news was just a very big part of our daily lives, especially when my three older sisters moved out and it was just the three of us, that was sort of our mode of communication.
We talked about the news. We watched the news together. Fareed Zakaria is basically the sun my parents always wanted. but so I got really into the news and being able to connect the news to, our everyday lives, which of course my parents had experienced as children and teens and Europe during world war II.
And also reading between the lines about why certain politicians might be saying something, why stories are getting published a certain way. So I just got really into that and I’ve always been into a and college, you know, I, I majored in English, but if we had minors at Berkeley, I would have minored in journalism.
I took a bunch of journalism courses. I’ve always been really into the media, but not so much as quite an insider where I go to work for a newspaper, but more observing, the news and providing sort of a lit review of what’s happening and what has momentum in the news. So I sorta got addicted to it and, Also as a writer.
My favorite thing to do is counter punch. I like to have somebody give me a topic and then I like to be able to quickly share my take, or make a joke or create a funny headline about that content. So I sorta took those two passions of the way I like to write. I like to write on deadline. I like to write fast and I like to counter punch and the content that I like, which is news, and I sort of merged those two things and created a product, and a pretty cool suite of internet tools to support that.
Yeah. So that makes sense that you’ve identified the constraints that match your style and made something exactly that fits it. the deadline, like having, he, you know, coming out with something on a daily basis, is more than a lot of creators want to do. so what’s your process there?
Yeah. I mean, I should emphasize that I do it every day. Not because I think it’s some incredible draw for readers to get Daily Content. I do it every day because I’m addicted to it. If my newsletter had five stories in it, instead of 10, it would do better. If my newsletter came out three days a week instead of five days a week, I’m sure it would do better.
If it came out once a week, it would do even better then you know, also if I had a more marketable or not marketable, but a more, business-oriented topic that was more narrow, it would do better. I used to write a newsletter that was just on tech and it was. Really popular in the internet professional community back in the first boom, I had about 50,000 subscribers and there were probably about 52,000 internet professionals.
So I just like writing about what I want to write about and I’m addicted to pressing the publish button and I’m just addicted to the process. So I do it because of that. I’m not sure that would be my general advice to somebody trying to market or promote a newsletter.
Yep. Are there other iterations, either ever before or things that you tried that you realized like, oh, that’s not a fit for your personality, your writing style?
Yeah. When I first started it, I actually, I’m an angel investor also and have been since, probably right after Google and Yahoo launched. so a while, and I used to, my passion has always been writing, so I wanted to mix writing into that, process. So I would send out 10. Daily stories, but they were all tech news related to the CEOs of the companies I worked with and a few of their employees, so that they wouldn’t have to spend their time reading the news or worrying about competitors or worry about what the latest trends in tech, where I would give it to them.
And they could focus on doing their jobs and that sorta got shared and got out. so I did that for a few years. really, that was my iteration. I should’ve kept the brand. It was called David Netflix. not that it was a great name, but I’ve shifted brands about 40 times in my life. Cause I love branding and naming.
I that’s another, maybe this is more of a cautionary tale than a lesson and newsletter marketing. I would stick with a brand if anybody has the possibility of doing that, that was a big mistake I’ve made over the years is having multiple brands. But when the bus came, the first internet bust, I basically was writing an obituary column every day and about companies that had failed.
So I just decided, I wanted to expand it and I knew I was interested in much broader topics than just tech news. So I expanded it to all news, a critical point that, really changed Next Draft and got it to catch on and become more popular was when I decided to focus on making it more personality driven and less, less overwhelmingly, providing an overwhelming level of coverage.
I used to think that I had to provide all the news in the day because people would sort of, depend on me to provide their news. I was sort of selling myself as your trusted news source. So I would include a lot of stories that I didn’t have anything to say about because they were huge news, you know, an embassy closed in Iran or whatever.
That was huge international news, but I didn’t necessarily have anything to say about that that day. So after a while I decided, no, I’m not going to do that. I’m just going to limit it to 10 items. And I’m going to focus that on what I think is the most fascinating and think of it less like a curation tool and more like, a, modern day column.
I think if the column newspaper column were invented today, it would look a lot like Next Draft people would sort of share their takes and then provide links off for more information. once I did that, it was a big change. People started signing up much more readily and, once I stopped trying to be exhaustive.
That makes a lot of sense to me. I think that that’s something you see from a lot of creators is that they’re, they’re trying to find some model. That’s like, this is my idea of what people should want, you know, rather than what they end up doing, eventually it’s coming to, it’s like, okay, forget all of that.
This is what I want. And I’m going to make that. And then people like me can find and follow it. And people who don’t can, you know, do their thing. Can you go find one of the other million sources on the internet?
Yeah. When I think of the people that I like to follow or have followed forever on the internet, all of them are that ladder. They just do it their way. They have a design, they want, they stick to their guns. They say what they feel like saying. they decide. what the personality of the product is.
And, they move within that. I always find that to be the most interesting thing, especially when it comes to something like newsletters. I really think newsletters are more like a radio talk shows than they are like other internet content, podcasts to a certain degree as well. But I always feel like I listened to are used to listen a lot to this radio, sports caster named Jim Rome.
And whenever he would have a new city that he was launching and he would always give the same speech on the Monday that they launched saying, just give me a week. You might not.
Get the vibe of what we’re doing today. You might think it’s okay, but not great, but just give it a week and listen, and then decide if you like it or not.
And I sort of feel like that’s how newsletters are your relationship with your readers sort of creates this, sort of insider-y voice and communication that, you, it takes a little while to get into the rhythm of getting it. But once you do, then it’s like this familiar voice or this familiar friend that you feel like, even if you didn’t read it for a few weeks, you can start a conversation with that person right away easily.
That’s how I think the voice of a newsletter is most effective. So that’s why I’ve always thought of it. More of what I do is sort of a textual talk radio, more so than a blog or some other format
What do you think, or what would you say to someone who maybe had 10 or 20,000 subscribers and felt like their newsletter had gone a bit stale and maybe their relationship to it had gotten a bit stale or they’re in this, this position of writing things that no longer have their voice, how would you coach them through like bringing their voice and personality back into it?
I mean, it’s definitely hard. it’s hard doing something that you do alone and, something that is often hard to really get off the ground or get to grow, especially when you’re on a platform like the internet, where every day, somebody does something and 10 seconds later, they’re like internet famous and you’re trying day after day.
So, I mean, the first thing. Is that you really have to be interested in what you you’re passionate about. and focus in on that, because that will alleviate a lot of that stress. Like, do I feel like sending it today? I’m a too burnt out. What’s the point? I mean, not that those feelings don’t happen. I had those feelings as recently as an hour ago, when I press publish, I have those feelings and disappointments constantly, you know, that’s part of being a creator of any kind.
Maybe that word is sort of, sort of goofy, but anybody who’s putting themselves out there and putting content out, you know, you have that feeling all the time. If you’re an indie, and you’re doing it all day in front of the computer by yourself, then that’s even more powerful because, you know, if you work at a big company or everybody’s working on the same goal, or even in a small group, you can sort of support each other and, maybe even bullshit each other at some cases where, oh, no, this really matters.
You know, where, if you’re by yourself, that has to be pretty self-sustaining or self-sustaining. I do have a friend or two that I always share blurbs with who, one of my friends Rob’s, he proves almost all of my blurbs, so it’s nice to have that virtual office mate. He’s not really officially part of Next Draft, but you know, I don’t think I would do it as easily or as, for as long if it weren’t for him because he’s like my virtual friend on the internet that says, oh, come on, let’s get it out today or whatever.
So I think that’s helpful to have a support team or a couple people you can count on to sort of give you a boost when you need it. But the key really is, is that it’s gotta be something that you are passionate about, both in terms of the product and in terms of what you’re focusing on, because if you feel strongly about it, then it really.
I don’t want to say it doesn’t matter if people enjoy it, you should take cues from your readers. What are they clicking on? What are they reading? What are they responding to? But at the core, it’s gotta be you because that’s what gets you through those down points? you know, I had a weird thing because I write about news.
The general news, world basically benefited dramatically from the Trump era because everybody was habitually turning on their news, 24, 7, and refreshing and Whitey and Washington post and checking Twitter every two seconds to see what crazy thing happened next. And we’re all poor sorta,
Wreck to watch.
So everybody was really into it and it created.
Unbelievable platform for people to become media stars. You know, Trump was bad for democracy, but he was great for media. Great for creating new voices out there. whether we like it or not. for me, it was different because I wrote about all news. I wouldn’t say I was apolitical, but I wasn’t heavily political.
The Next Draft had plenty of readers from both sides of the aisle. when Trump came around, it was like one story every day, basically. So it really limited. I would get emails from longtime readers all the time that said, Hey, can’t you cover something other than Trump every day?
And I say, Hey, if you can find the story for me, I’ll cover it. This is what every journalist is on. Now, the people who used to cover the secret service around Trump, the people who used to cover sports are not talking about Trump because of a pandemic relation ship to it. The people who aren’t entertainment are talking about Trump because they can’t believe that anybody voted for him, whatever the issue was, every dinner party was about Trump.
So it was really a bummer for my brand and my product. Actually, it became boring in some ways to me to have the same story every day. And it became, I think frustrating to my readers.
But during that era, when it was happening, I had to make a decision. Do I become more political and go full on with this?
Or do I sort of try to. Do what I would call a falsely unbiased view or a, you know, false equivalence view that we saw in the media where there’s both sides to every story. And you have to pretend they’re both accurate, including one guy saying to put disinfectant into your veins. And the other person’s saying to wear a mask and take a vaccine, but those things get treated as equal somehow because the president said it.
And I really decided, you know, more important than keeping readers is that I’m true to my own sort of ethical standards. In a moment that called for it, at least for me. So I became more political. went into it and I said, what I believe and still believe is the truth, you know, about what was happening with Trump and Trumpism and our slide towards authoritarianism.
And I know that this is a podcast more about newsletterish than it is about politics or news, but I’m just sharing that because that’s the kind of thing that kept me going. and the people who really cared about what I was writing, appreciated it and would email me and say they got something out of that.
And most importantly, my mom would say, yeah, you made the right call. Or my dad would say, yeah, you got that. Right. And ultimately, When it became a sort of a bummer period for me, which I would say 2020 was because of all the horrible news. And, I was writing a book about the year. So I was like living, July of 20, 20, well writing about March of 2020, which I don’t recommend for anybody’s emotional health.
And I just had to think like, what’s really important to me. Yes. I want to be funny, which I try to be in my newsletter every day. I want to be read my narcissism is as strong as ever, but ultimately I want to be able to look myself in the reflection of the, darken screen on the rare times that it is dark and say like, yeah, you told the truth and that kept me going there.
So I think whatever your brand is, you know, it can be a newsletter about guitars, but if you have that sort of passion, And you have something you want to say, and you think is important to say it sort of gets you through those levels and your motivation. And if it’s not getting you through the lows and the motivation, there’s nothing wrong with saying, Hey man, this is not worth it.
I’m going to go try to make something else. You know, it doesn’t have to be, you don’t have to beat a dead horse.
On the political side. Are there specific things that you felt like it costs you opportunities that it lost you? Because I think a lot of creators, whether they talk about, you know, finance or photography or whatever, I’ll see these things. And they’re like this either directly relates to me and my audience and I feel like I should take a stand on it.
Or it’s like a broader macro issue that I feel like we should talk about. And when you do, then there’s immediately, you know, somewhere between three and 300 responses of like, we didn’t follow you for the politics, you know, or like something like that. And your Instagram, DMS, or newsletter replies or whatever.
Yeah. it costs me a lot. Definitely it costs me readers or subscribers. It costs me, psychic pain because I was locked into a story that was just overwhelmingly, emotionally painful, really, and shocking and difficult to understand all the things that cause you sort of emotional exhaustion. We’re in the Trump story, especially in 2020, when it became a story about our own health and our kids’ health.
And the frustration level just went through the roof. for me, professionalizing that content actually helps create a bit of a barrier to the feelings about it. Some of my good friends were probably more bummed during 2020 than I was because when the latest crazy story or depressing story would happen, I felt I had to. Ingest that content and then come up with, something cogent to say about it. And maybe hopefully funny to make it a little bit of sugar to take the medicine and then get it out to people. So I’ve always felt that being able to do that, sorta created a barrier between myself and actually feeling something.
So that’s another thing I like about the newsletter probably at least unconsciously. but yeah, there was a lot of costs in terms of readers, for sure. Hate mail. but there always is, you know, Today. I would say I get much more hate mail from the far left. If that’s what you want to call them. People who feel like every joke is like an incredible triggering a front to their existence or any hint that you mentioned somebody as attractive.
I’ve gotten hate mail because I implied that Beyonce is appearance was part of her brand. I mean, it’s totally crazy, but, It’s those extremes. You have to be able to turn off. You know, a friend of mine used to work at a major, be the editor of a major American newspaper. And he said every Friday they would get together and they would play the craziest, calls to the editor.
They had a call line. In addition to, you could send a letter or you could call, leave a voicemail about something you were upset about in the coverage. And they would just gather around and have drinks on Friday. Listen to this because of course the people who are calling this line are almost self-selecting themselves as a little bit wacko and their takes were usually pretty extreme.
The internet, Twitter, social media, Provides, greases the wheels for those people to be more prevalent in our lives. But I think it’s really important to know that that’s a real minority of people, somebody who sent you a hate mail, that your joke was so offensive, or they can’t believe you mentioned that people ever watch pornography on the internet or any of these other things, it’s this tiny minority of people.
And then it’s one step crazier that they felt like they had to contact you. So that’s a really hard thing. I think about being split, particularly the newsletter game, because anybody can hit reply and you’re going to get many more replies from people with crazy complaints, than you are from people with really thoughtful responses.
Not that those don’t come and those are valuable and I love getting those, but you get many more from people that just have really bizarre. I mean I could list probably for hours to crazy things that people send me that they’re mad about, you know,
Is there something specific that you do? Like one thing when I get those replies, if they’re just like completely off the wall or abusive or something like that, I just scroll down and then click their unsubscribe link because, you know, they’re never going to know, and then I just have to show up in their inbox
There’s something that you do.
That’s not a bad strategy. I like that. I do do that occasionally for sure. occasionally I’ll just go to Gmail and just, create a filter for that email to automatically go to my trash. if it’s like a hardcore right-winger, that’s telling me how stupid I am about ivermectin and that, you know, people should be taking horse dewormer and I’m just not getting the truth.
And that Trump is awesome and that, Whatever. I usually just delete, honestly, because I don’t see a big benefit to replying to somebody, especially if it’s like a rabbit email, you know, they’re looking for a reply, they want the conflict. A lot of people sleep easy with conflict. That’s one of the lessons of the internet that I learned when I was first starting on the internet, you know, David edix sort sorta became popular because somebody that had a blog with a similar name, that I hadn’t heard of, complained that I sort of stole his name because his name was also Dave.
And I had got like, probably about three or 400 emails saying, you know, with expletive saying what a horrible person I was. And I also got about 3000 subscribers and at the time I had about 30, so. I didn’t know how to respond. I felt like, wow. Number one, I didn’t know that guys had the product with the same name.
Number two. My name was different enough. Number two or three were both named Dave. I mean, who cares? You know, and plus I don’t want to be attacked by anybody. So your first reaction is to respond and a slightly older, although not noticeably these days with my gray beard, slightly older friend of mine who had been in tech a little longer, said, don’t respond.
This guy lives for conflict. You guys are going to fight. There’s going to be this public thing. You’re going to be up all night and he’s going to never sleep so easy. So, I took that to heart and didn’t respond. And I, I think about that a lot when I get rabid emails from people, Mike exception, actually probably my weak point really is from, more my side of the political spectrum, where people who are generally liberal, but are just so extreme for me.
In terms of being triggered or having a joke, be every joke, be inappropriate. That those people, I actually do feel like I want to respond to because, I, I don’t think I can really motivate or move, somebody who was on the opposite end of the spectrum and is sending me hate aggressive, hate mail, but maybe I can move somebody who’s just a little bit different than me, or a little bit more extreme.
I will respond to those, although I’m usually sorry. The one other thing I always respond to is if people have been reading, they say, oh, I’ve been reading you for years. And, I wanted to ask you a couple of questions about this book that you wrote before ordering it. And I’m like, just order the damn book. that’s probably my most common email to people these days. It’s actually remarkable how many people says, wow, I I’ve been reading you for years. I share you with all my friends. something, when my sons come home from college where it’s always talking about, Dave said this, Dave said that, before I buy your book, I just wanted to ask you a couple of questions to make sure it’s going to be for me.
I’m like I worked on something for an hour and it’s like, your family is talking about it. What, just by the thing I worked on for a year, you know? So those kind of things, personal frustration, I respond.
Yeah, that makes sense. okay. I’d love to talk about the book some more, but before we get into that, there’s two things I want to talk about. The first one is like, how do you measure success for the newsletter? What’s the thing that you’d like to, cause I don’t think it’s, you’re pursuing the monetary side for this.
It sounds like the monetary side comes from investing and, and then what’s success for the newsletter.
I mean, I have had right now, I I’m just marketing my, my own stuff. And during the pandemic I marketed non-profits, but, that had to do with either the pandemic or, the democracy issues that we were facing. but I have made decent money from selling straight sponsorships. Year-long sponsorships to people, which I highly recommend.
I think some of the ads that people put into his letters that go by clicks or whatever, unless you have a massive audience, it’s hard to make much money, but if you pitch to some company that is a like-minded brand, Hey, you’re going to be my only brand for a year. And anytime you have special events, I’m going to mention it.
Then you can say, okay, you have like, you know, 20,000 readers or a hundred thousand readers that can make a difference to a brand to say, yeah, it’s like a rounding air show. We’ll give you 20 grand or a hundred grand or wherever it comes in there that you can actually make a decent. Living in terms of writing.
So that always worked better for me, but no, my, my internet life is really all about narcissism and, clicks, you know, the dopamine, I just want reads. I’d rather you subscribe to my newsletter than pitch me your startup company. I just, that’s what I want the most. So more numbers, more opens, more reads, more subscribers.
And unfortunately that’s probably the hardest thing to get also, especially in a product that is sort of viral. I think newsletters are sort of viral, but it’s better if you have a team and some tools to really get it going. That’s, you know, sites like the Skimm morning brew and the hustle. They have teams that are really growth hacking and focusing on that and having rewards programs and ambassador programs.
The reason you see that is because.
Newsletters themselves are not really inherently that viral. Yes. Somebody can forward it to one person or whatever, but it’s not as viral as a lot of other forms of content where you can click a button and share it with all of your followers, like a Facebook post or a tweet.
So yeah, the thing that matters to me most is probably the hardest to get in the newsletter game, but that’s the truth
Yeah. Well, I think the, the point on like newsletters don’t have a distribution engine. There’s no Facebook newsfeed, YouTube algorithm equivalent for newsletters. And so it really relies on either you posting your content somewhere else, whether it’s Twitter or YouTube or medium or something that has an algorithm or your readers saying like, oh, I read Next Draft.
You should too. There’s not really something else in there. Have you looked at, or I guess if you have thoughts on that, you comments on it, but then also have you looked at launching an ambassador program or, or an actual referral program?
Yeah, I’ve thought about him. And now over the last year, there’s been a few tools that have come out a few. I think X people from sites like morning view Ru, and some other sites that have sort of perfected some of these marketing programs have, sort of come out with these tools. I’ve messed around with them a little bit.
Some of them still require I find, some technical ones. so I, I have like an engineer who works with me on Next Draft, like as a freelance basis every now and then, but it’s not always easy for me to launch stuff that requires a lot of a moment to moment technical support, and management, because it’s just me using a lot of, they’re customized, but they’re over the counter tools.
So I’ve thought about a lot of them, but I really haven’t tried it that much.
I want to though I do want to do that. I would like to do one of those programs, especially where you get credit for referrals. I think that’s the best kind of model. So there’s one called spark loop.
Yeah, we actually, I invested in spark loops, so we
Decent portion of that business, so good.
Oh, nice. Yeah. That one, if it was just slightly easier, I know that it’s probably difficult to make it easier because, there’s so many pieces. They have to have your subscribers. I have to have my subscribers, but that is, does seem like a good product. And especially if they can, I think expand into like letting a person sell a product or whatever, get credited for sharing products that can be even bigger.
But yeah, that kind of stuff is really powerful for sure. And I, I do want to get into that. it’s more just inertia that I it’s just a matter of sitting there for the, an amount of hours that it requires to get it going.
But I do think that’s a great thing for newsletter writers to do, and I’m pretty surprised that more newsletter platforms don’t build it right in.
I think that’ll probably change over time too. Maybe you guys will get acquired by.
Yep. No, that makes sense. I know for convert kit, we wanted to build it in, it looks at the amount of time that it would take and then said like let’s invest in a , you know, and then roll it into our offering.
Yeah, it’s hard. It’s hard not to take that stuff personally, too, you know, for people that do newsletters, you think you’re going to put a thing on there and say, Hey, you know, it’s just me here and you always read my newsletter and click. I know you love me so much. Can you just do this to get a free whatever?
And it’s, you know, sometimes not that many people click, you know, or other times like they click just as long as there’s the free item. So there’s a lot of ways to get depressed. Like I had things where I say, Hey, the first a hundred people who do this, get a free t-shirt or whatever next strap t-shirt.
And those hundred people will literally do what I asked them to do in like 34 seconds, you know? And then it like stops after that. The next time you ask them, if there’s not a t-shirt. But it’s not you, you know, if you go to a baseball game or a lawyer game or whatever, you know, people sit there, they don’t even cheer as much for the team as they cheer when the guy comes out with the t-shirt gun.
So it’s like, people love t-shirts more than they’re ever going to love you. And you have to go into these things with that in mind. there’s no way, even if it’s, even if you’re XX large and the t-shirt is, you know, petite, it’s still worth more than you are. And the average mind of the average person.
So you have to go into all of these things thinking, I hope this works like crazy, but if it doesn’t tomorrow, I open up the browser and start writing.
Yeah. That’s very true. I want to talk about the growth of the newsletter. I was reading something, which I realized later was back in 2014, that you were at around 160,000 subscribers. I imagine it’s quite a bit larger than that now. And then I’d love to hear some of the inflection points of growth.
Yeah, I’m not, I’m not sure. I might’ve, I don’t know if I lied in 2014, but now I have about,
Quoted it wrong.
No, you might’ve got it right. I might’ve exaggerated. Maybe that was a including app downloads and a few other things. Yeah. I have about 140,000 or so now, so that would be making that a pretty horrible seven years now.
You’re depressing me.
Your listeners should just stop, stop writing newsletters. It’s not worth the depression
Just give up now
Yeah. And by all means if Nathan goals do not pick up. no, yeah, I probably have it 140,000 on newsletter. Made my newsletter. It’s hard to believe in this era of newsletters actually, but when I first launched Next Draft, I noticed that even people who would send in testimonials or that I would ask for testimonials would say, basically something to the extent that even though email is horrible, this is the one newsletter I I’d sign up for whatever.
And I kept thinking, man, that’s a bummer that I’m starting out at this deficit, that people have a negative feeling about the medium. So I, since then I’ve always made it my goal to. Have the content available wherever people are. So the newsletter is certainly the main way that people get next job, but there’s an app for the iPhone and the iPad there.
That’s the first thing I launched because I wanted to have an alternative for people who just hate email too much. So now you go to the landing page, it’s like, Hey, if you don’t like email, here’s another version. I have a blog version. I have an apple news version. I have an RSS version. I’m lucky enough to have a really good, WordPress custom WordPress install that I just push one button and it pushes it out to all of those things.
But I am, I’m a big proponent of just meeting people where they are. even, as an example, I recently launched a sort of a substance. Version of my newsletter under the radar. but when I redo my site, I’m going to make that more clear because if people already subscribed to like 10 sub stacks and they’re using their aggregator and they already have their email saved and they can just click a button, it’s like, I don’t care.
You know, it takes me five extra minutes to paste my content into sub stack. So I just want the reads. I don’t really care about how they read it or whether they read it.
Yeah. That’s fascinating. So then let’s shift gears a little bit. I want to hear about the book. first I wanna hear about the title. Would you have it on your shirt?
Yeah. That’s pretty embarrassing. I swear. I didn’t know it was video today, but I do have a shirt
Otherwise I wouldn’t have worn. This would have worn my Nathan Barry’s shirt.
That’s right. It’s in the mail actually. It’s
Oh, good, good.
Big photo of my face.
Yeah. Convert kit. My wife converted to Judaism before we got married. So I have my own convert kit.
There you go. Exactly. so I want to hear like what the book is about and then particularly where the title came from,
It made me laugh a lot when I heard it.
Oh, cool. That’s good. That’s a good start then. yeah, the title comes from, in July of the, of 2020 when the pandemic was really setting in and becoming a reality for everybody. this amusement park outside of Tokyo in the shadow of Mount Fuji called the Fuji queue. amusement park reopened.
And they found that even though everybody w everybody was wearing masks, people were screaming so much on some of the rides, especially the Fujiyama roller coaster, which was their scariest ride, that they were worried about germs spread. So they sort of put signs around the amusement park saying, no screaming, you can come, you can ride and have fun, but keep your mask on adults scream.
And it sort of became a little minor social media thing in Japan, where people were sort of making fun of them like, oh, they’re telling us not to scream. How can anybody not scream on the Fujiyama roller coaster? So in response, the, park management had to have their executives with perfectly quaffed hair and tie and colored shirts and masks on ride the roller coaster with a webcam facing them the whole time without moving a muscle.
Cracking a smile or grimacing or screaming. And then at the end of the ride, when the rollercoaster stops, it says, please Scream Inside Your Heart.
And that was always my favorite meme of, 2020. It went really viral. There was like t-shirts. aside from mine, there were posters memes. It sort of went crazy for about a week or two, which by 2020 standards is a pretty long time for a meme to last.
And I just thought that made sense as a title for the book, because that’s sort of how we felt, all year that I dunno if we were screaming in our heart, but we were certainly screaming into a void. Like no matter what we sat or yelled on social media or complained to our family members or friends, it just kept getting worse.
The year just kept getting worse. And, so the idea is that this book sort of, now you’re free to sort of let out the scream. And the book is it’s about 2020, certainly, but it’s really about the issues that led us to 2020. There’s a ton about our relationship to media and including my own relationship to media and how that got us into trouble.
Some of the stuff we’re talking about today, how, technology has impacted our lives stuff. I’ve been sort of thinking about it, writing about for the last few decades, and a lot of the political hate that emerged. and, but it’s all within this time capsule of the craziest year.
Yeah. Yeah. And so that’s coming out early in November, November 2nd. so you’re, it looks like you’re just starting the, you know, mentioning the promotion tour and all of that. is there a big, big push that comes with it or are you kind of, I, I’m always curious with people’s book launches, what strategy they take.
Yeah. I mean, I’m a newbie, so it’s, the whole process has been interesting to me working with a publisher, working with others, is not my forte. so I got used to that or I’m getting used to that and they’re probably getting used to it also because working with grouchy 50 something in these is probably not ideal, but, yeah, I’ve just been promoting it so far in Next Draft, but I’ve been doing, I have a PR company that’s helping me and I’ve been doing a ton of podcasts and I’m marketing it to my own readers.
And then as it gets a little bit closer to the November 2nd date, I have a lot more stuff planned rut, a lot of influencers have early copies of the book, and hopefully they’ll promote it. And, I’ll call out a few favors from bloggers and hopefully newsletter writers. I feel like that should be my in theory.
That should be my secret weapon because, in addition to being fun and creative, nothing moves traffic, except maybe Facebook, nothing moves traffic more than newsletters. I know a lot of people who run e-commerce companies and newsletters are always second, if not first, in terms of traffic drivers.
So, I really think that, if some of my friends out there at morning brew in the hustle and the scam and all these other sites that sort of, have surpassed my size by quite a bit, put the word out that, one of their fellow warriors is, has a book out. That’ll probably move the needle even more. The media, I’m hoping to get stuff like that, but I really don’t know. I’m trying not to get my hopes up too much because, unlike a newsletter, it’s not just one day’s work, you know, you like worry about one word or one sentence in a book for like three weeks and then you put it out there and people are like, oh yeah, I’ll check it out sometime.
Thanks. So, you know, that’s, you know, whatever that’s life as a, you put yourself out there, that’s how it goes. So I’m hoping it sells well. And, the more people that get it, I think some people, their first reaction is, oh my God, 2020. I don’t want to relive that again. But, hopefully people who know my brand and those that they share it with, know that it’s, you know, there’s a lot of humor and there’s, it’s probably 30 pages before we even get into the first event of 2020.
So it’s, there’s a lot more to it and it’s sort of fun and crazy and tries to have the pace of a roller coaster. that was the other thing I took from the Fujiyama roller coaster.
Yeah. So one thing that I’m always curious about with people who have like a prolific newsletter, you know, in your case of writing every day, and then like, for a lot of people, that would be a lot to handle of staying on top of a daily newsletter. And then you’re writing a book on top of that. How did you schedule your time?
Were you blocking off like, oh, these afternoons are specifically for book, book writing. Cause you turned it around relatively fast.
Yeah. the newsletter is sort of like a full-time job. People always ask me, you know, when do you work on, or how many hours do you spend on it? I mean, I’m, I’m always looking for news, whether it’s on Twitter or friends, emailing me stuff or texting me stories, or just in conversations with people to see what they’re into or what stories are interesting them or what I’m missing.
In terms of actual time spent like where I’m dedicating time. I probably do like about an hour every night, because the story has changed so quick. So I’ll do an hour of looking for stories every night. And then the next day I sort of lock in from about nine to one, usually, or nine to 12, where I’m finding stories, saving those stories, choosing what stories I want to go with and then actually writing the newsletter.
All of that takes about anywhere from like two and a half to four hours, depending on the day I go pretty fast. When it came to the book, that was tricky. It was actually more emotionally tricky because like I said before, I was like, had to go back and write about, you know, Briana Taylor while I’m living another horrible act, you know, or even more so the Trump, you know, one crazy Trump thing and another crazy Trump thing and seeing the pandemic getting worse and worse.
So that was stressful. But I found at the beginning I would try to write a lot at night and that was okay. But I found actually if I just kept going, in the day when I was already rolling and had written the newsletter and I was already in the group just to add on an hour or two to that was actually easier and more effective for me than trying to get going.
But that’s just me. I mean, I just go by my it’s almost like my circadian rhythm or something like that, I almost never eat or consume anything before I’m done with next job except for coffee. I would keep that going, you know, once I would like, sort of have a sandwich or whatever, then it’s like, oh, let me just take a quick nap and then whatever.
So, yeah, I tried to just keep it going. I always find the more consistently busy I am, the less I procrastinate. And if I take a day off or I take a few hours off, even then, between writing, it just, it takes me longer to get going.
Yep. That makes sense. The habit that I’m in right now is starting the day with 45 minutes to an hour of writing and that’s working much better for me than like slotting it in somewhere else. So I think like w what I hear you saying is like, experiment and find the thing that works well for you.
Yeah. I mean, if you’re going to start experimenting almost every writer, I know not like newsletter writers, but just general writers, all do what you just described. They sort of pick a time in the morning and they get their output done. then the rest of the day, if ideas come to them or whatever, they jot it down, but they’re sort of powering in that morning hours.
That’s probably a good one to try. Although, you know, some people just do it better at different hours. I’m sure.
Yeah. another thing I realized, I’ve always you for years, and until we got on this video call, I had no idea what you looked like. and which is kind of an interesting,
Well, I’m sorry.
It’s by design. I have a face for Panda.
Tell me more about, well, I guess two sides, one, has there ever been an interesting interaction? You know, because you’re like, Hey, I’m, I’m Dave and people are like, I wouldn’t have ever recognized you. Or has there been any other benefits and thought behind, you know, why it have an avatar?
If by interesting you mean horrible? Yes. There’s been many interesting interactions with people. I mean, before, before I had my current, avatar, which is, pretty awesome, actually, a guy named Brian Molko designed it. I had this incredible drawing of a character that looked like me that, had sort of ether net, Machinery and cord going into his head and it was like me, but my head was actually lifted.
The top of my head was lifted off and you could see all this machinery and it was an incredible graphic, by this guy named Sam Spratt. Who’s now done, album covers and book covers. He’s like a super talent. If you want to follow somebody fun on Instagram, he’s just incredible. And it was a drawing, even though it looked photo realistic.
And I used that for a while and then I would go places and people would be like, you are so much fatter and grayer than I imagined. And so instead of having Sam sort of ruin his artwork, I went back with the more, cartoonish or animated, avatar. So since then I don’t get too much of that, but, that was a good move.
Although that’s the best thing about avatars and the internet is that your avatar never ages. It always looks the same. It stays the same weight. My avatar never overeats he exercises right here. Angie really gets along well with others and doesn’t have any kind of social anxiety either. So he’s pretty cool.
Yeah, it goes a little downhill with me in person. So
Yeah. So is it, that’s something that like, it gives you some distance between you and readers, or it gives you some anonymity that, you know, you don’t want to be recognized in the streets?
No, no, it’s, it’s, basically just what I described. It’s like, I literally prefer the, the attractiveness of my avatar versus me, but also actually my avatar is really awesome. my logo, so it’s also iconic and scalable. so it looks awesome on t-shirts even people who don’t know what Next Draft is when they see, by son wearing his t-shirt, whatever, it just looks awesome.
So that that’s that’s as much of it as anything. I thought your response was going to be mad. You seem perfectly attractive to me. I don’t know what the issue is, but no, you went with, am I doing that for some other reason? Yeah. So, I get this all the time.
Cause my wife is a very attractive person also. So when people meet me, they’re always like, whoa, we were once a very famous celebrity came up to me and I said, oh, I’m Gina’s husband. And she was like, wow, you did well. Oh, you know? So I’m like, thanks a lot. That helps. So just gave her a picture of my, my icon and walked away.
Then that worked. I’m sure that she has it framed in her office, from now on. it’s just interesting to me. You’re you’re sort of at this intersection between personal brand and, like media brand. And I think the avatar helps push you over into the media brand side. and I don’t have any real commentary on it other than I find it interesting.
Yeah, no, I think there probably is some of that. I I’ve never really been a fan of using my actual face, or my actual person as a logo. I love the process of designing or working with people to design logos and taglines and all that. But yeah, probably at some point there was a, a goal with Next Draft to make it seem bigger than it is.
I know a lot of people that are solo operators. They regularly say we, when they’re talking about their brand to make it seem bigger, I actually think that’s sort of been flipped on its head though. in the last few years where so many people are coming into the space, it’s very clear that what they’re doing is leaving a big brand, leaving a we and going to an eye.
And I think it’s actually a selling point in a lot of ways. So, I mean, I, I still get a lot of emails that say, I don’t know if anybody at Next Draft is going to read this email, you know, or if you do, can you get this message to Dave? He’s an asshole or whatever. And it’s like, I’m the only one here, you know, or the other one I always get is when I email back to people that go, oh, I can’t believe you actually emailed back.
I didn’t think this would get to anybody. It’s like, you hit reply. And it had my email, like where else would it go? Exactly. You know? But I think actually having people thinking of you as a person, instead of a brand, Is a benefit today. Whereas if you would ask me when I was younger, I probably would have said, make it seem like you have a big company behind you.
Yeah. And I think that that indie shift overall, like people are looking for that.
Want to ask about the intersection between your investing and the newsletter. like, are you still actively investing today and doing author.
Yeah, yeah, no, I, I still invest a ton. I usually follow along with people who are a little more in tune with today’s companies than I am. I don’t really go out there and brand myself as an investor much, but I’ve been really lucky. I have very little intersection actually, if any, with my newsletter and my investing and I definitely want people to. To think of me as a writer first, for sure. Not as an investor who has this hobby, because that’s definitely not in terms of time or passion, the reality. but I’ve been really lucky over the years that, I’ve invested with people or co-invested with them that were cool with me. branding myself as a writer first, but still looking at deals that came through their brands because they were branded as BCS or investors or angels.
That’s probably a bigger deal now than when I first started. There were like five angel investors, basically. Nobody really did small, early stage seed deals. you know, I mean, we all knew each other that did it and now there’s like thousands of them. So you really have to be either a really pretty well-known entrepreneur or you have to. Sort of attach yourself to our organization or two who are really branding themselves well, getting out there and building a stable of companies,
It’s pretty different, more, much more has changed about that than the newsletter game, actually, which is pretty much the same as it was the day I started actually.
Are there a few of those I’m curious who are a few of those, people that you would tag along with, you know, when they’re investing where like, oh, this person puts money into something I’d like to be right there with them.
I mean, I have some people that are like entrepreneurs and former entrepreneurs that do it, and if they like it I’ll do it. but generally I co-invest with, at any given time, a different group of people, used to be a larger group. When I first started out, my whole investing career, I’ve co-invested with this guy named Bob zip who’s much smarter and much wiser than I am about all things business and.
Startup world. So that was really great. And he used to work at a company called venture law group in the first boom, and they represented Google, Hotmail. eGroups all the big, huge, early internet companies, and so he really knew the space well. And when he became, I used to get deals from him.
That’s how you used to get deals actually was by a couple of law firms that focused on startups. I’ve been co-investing with him all along and he’s been generous enough to, he left the law firm a long, long time ago and became an investor primarily. And he had a fund and was well-known guy and well-respected guy.
So I got to sit in when he would hear pitches. and we sort of, we weren’t investing together out of the same fund, but we would sort of make our decisions together. And we still do that a lot. these days, I almost always follow along with a guy named run-on barn Cohen and a really good friend of mine.
He was for many years at WordPress, basically, most of the things that make money at WordPress, he did. and now he’s a investor at a VC called resolute. If anybody’s looking for a good VC, he’s like incredible, like Bob zip much, much smarter than I am about this stuff. Unbelievably ethical, great business sense.
Great technical sense. so I mostly just follow him. So if he does something that’s usually good enough for me. And if I see something that I think it’s good, I’ll pass it along to him, but it’s mostly that, but I’ve been really fortunate. I can’t express that enough, that I’ve been able to invest in companies without having to spend all of my time, branding myself as an investor.
That’s just been unbelievably lucky. So, I’ve been able to focus a ton of my energy on my six.
That’s right. I’m writing a newsletter about the news. I guess, as you’re looking to grow and continue on, right? Like the next phase of readers and, and all of that, since we can just say directly that we’re all narcissists and we do this for the attention. what’s what’s sort of that next thing that you’re looking for, it’s going from 140,000 subscribers to say 200,000 and beyond.
Yeah, well, I’m, I’m hoping that, I’m not just trying to sell my book here. I’m hoping that the book and the newsletter will sort of have, a coexistence with them because the new the book is really an extension of the brand and the brand is that icon to Next Draft. So I’m hoping that the tricky part about writing about marketing a newsletter, like we discussed earlier, there’s not really a natural virality to them.
So. You Have this piecemeal growth from people telling each other or their friends or forwarding it to somebody or maybe occasionally tweeting or sharing a Facebook link. Oh, you should check this out. But it’s all sort of small little blips. If you get a news story or a big blog story about it, or another newsletter recommending you, that’s probably the fastest way people grow these days is by, co-sponsoring each other’s newsletters or co-promoting them.
Those big hits are more rare and they usually require like, I’ve had a ton of stories written about Next Draft, but most of them a long time ago, because it’s basically a similar product to what it was when they wrote about it the first time. So they’re like, Hey, I’d love to write about it, but what’s the hook.
What’s the new thing, you know? so I’m hoping that the book provides that emphasis. It’s like, we’re doing now a ton of people who may by either been on a podcast in the past, or they’ve wanted to do a podcast with me say, okay, now’s a great time. I’d probably want to move your book and, we can set something up.
So it’s sort of as an impetus. So I’m hoping that that will be the next big newsletter thing that most, most people who write about the book will also write about the newsletter and the two things can sort of grow together.
I think that’s spot on.
That’s in terms of, you know, marketing and promotion, otherwise, I do want to try, one of these referral programs because people definitely do like products.
And, I am lucky that my icon looks really good on shirts so that people actually really want them. And I have a great designer named Brian Bell who makes all of my shirts.
There’s something like when creators thinking about products, often if you spread yourself too thin, you’re like into the newsletter, the book, the podcast, and like the 14 other things that you could make all at once you sort of hinder the growth of each thing, but then if you really build one of them up to a significant level, then at that point it can start to stall out and by shifting to another medium or have it like launching another product in this case, the newsletter to a book, then that book can have a bunch more momentum that feeds back into it.
And so there’s just sort of this interesting balance of like, no, When to like, keep pushing on the thing that you have versus when to add the next thing that like, then they feed off of each other and go from there. So I think you’re doing it with good timing.
Hopefully it’ll work. All that kind of stuff is the tricky part of doing this stuff. Especially stuff like podcasts and newsletters that are—it’s really a ton of word of mouth, unless you get lucky and get some press, and word of mouth is just slow.
There’s some point where you’re going to hit a tipping point where you’re going to go from five or 10,000 to like 50,000 much quicker, more quickly because instead of three people going home and saying, “Hey, did you ever hear of this newsletter?” there’s like 30 people going home and saying that. But, even with that they hit a plateau, and then you figure out what’s the next thing. That’s why doing something you’re into is so important.
And I don’t think it’s bad to try those other mediums or stretch yourself out, because you never know you might’ve been writing a newsletter three years, and then you do a podcast and it catches on. For some reason, you’re like awesome. Less typing, more talking, let’s go. So, but it’s tricky. I wish I was better and had better advice for people on promotion and marketing.
I’m not awesome at it, and it’s not in my nature. So, begging for favors or telling people, even in my own newsletter, to buy my own book is very painful for me. I’m very sensitive to criticism about it. So, if people just all bought it and then made everybody else buy it, that would be a huge relief for me.
That would be great. Well, along those lines, where should people go to subscribe to the newsletter, and then follow you on your preferred channel, and then ultimately buy the book?
I don’t want like two or 300,000 people taking my site down. So let’s go with if your last name starts between A and M you can start by going to NextDraft.com and sign up for the newsletter there. Or, you can also just go to the App Store and search for Next Draft. If you’re N through Z, you can start with the book, and that’s at: PleaseScream.com.
It has links to all the various audio, and Kindle, and hardcover versions.
That’s good. I liked how you split the traffic, that way there’s no hug of death, and we’ll do well there.
I don’t want to get fireballed.
Dave. Thanks for coming on. This was really fun.
Yeah, thanks a lot for having me.