a16z Podcast: So You Want to Launch a Newsletter—Tips From Writers

Illustration: Edith Zimmerman

This episode, part one in a two-part series on the Creator Economy, explores the process and economics behind creating an independent newsletter. In this candid conversation, host Lauren Murrow talks with four Substack writers—an artist, a technologist, a journalist, and a clinical researcher-turned-psychedelics scholar—about how to find and foster an audience, the calculus behind going paid versus unpaid, the pressure to produce, and financial benchmarks for making a living from newsletter writing.

The pandemic has prompted a reckoning within traditional media  and, along with it, a surge in the newsletter ecosystem. On Substack, readership and active writers both doubled from January through April. The newsletter hosting platform now has more than 100,000 paying subscribers.

This episode reveals the behind-the-scenes experiences of four newsletter creators, all of whom launched roughly within the past year:

Software engineer Lenny Rachitsky, most recently a growth product manager at Airbnb, whose tech-focused dispatch is called Lenny’s Newsletter.

Artist and writer Edith Zimmerman, creator of the Drawing Links newsletter, which chronicles her life and musings through comic-style illustrations.

Zach Haigney, an acupuncturist and researcher whose newsletter, The Trip Report, explores the science, policy, and business behind medicinal psychedelics.

And Patrice Peck, a freelance journalist—previously a staff writer at BuzzFeed—whose newsletter, Coronavirus News for Black Folks, highlights the pandemic’s disproportionate impact on the black community.

Listen to the end of the episode to hear more about Patrice, Zach, Edith, and Lenny’s top newsletter recommendations:

Patrice’s newsletter recs:

The Intersection by Adriana Lacy

Beauty IRL by Darian Symone Harvin

Carefree Black Girl by Zeba Blay

Maybe Baby by Haley Nahman

Zach’s newsletter recs:

Stratechery by Ben Thompson

Sinocism by Bill Bishop

A Media Operator by Jacob Cohen Donnelly

Off the Chain by Anthony Pompliano

The Weekly Dish by Andrew Sullivan

Edith’s newsletter recs:

The Browser by Robert Cottrell

The Ruffian by Ian Leslie

Ridgeline by Craig Mod

Dearest by Monica McLaughlin

Why Is This Interesting? by Noah Brier and Colin Nagy

Lenny’s newsletter recs:

2PM by Webb Smith

Li’s Newsletter by Li Jin 

Alex Danco’s Newsletter by Alex Danco

Turner’s Blog by Turner Novak

Next Big Thing by Nikhil Basu Trivedi 

Big Technology by Alex Kantrowitz

The Profile by Polina Marinova

Everything by Nathan Baschez, Dan Shipper, Tiago Forte, and Adam Keesling

Not Boring by Packy McCormick 

For more on newsletters and the expanding Creator Economy, visit a16z.com/creator-economy.

Transcript:

Lauren Murrow: Why did you launch a newsletter?

Patrice Peck: I launched Coronavirus News for Black Folks April 5th, I think. I became a journalist who covers stories about and for disenfranchised communities, but specifically black communities. And when I saw that the coronavirus was going to be disproportionately impacting people who have pre-existing medical conditions, I realized, “This is going to be overlooked. And so I was like, let me just aggregate this news, specifically as it relates to the black community.

Zach Haigney: I was aware of Substack and enamored with the process and the model. And then saw this emerging trend of psychedelic inspired medicine kind of coming through the clinical trials for things like PTSD, depression, anxiety. I thought it’d be a really great way to monitor the news, but also think about the evergreen issues that we’ll be facing in this new domain.

Edith Zimmerman: Yeah, part of the reason I started my newsletter was because I was doing these morning cartoons that I was turning into little stories that I was sharing on Instagram. I quit my job and started a newsletter and started sharing them on the newsletter instead. And there’s something about the newsletter and the reemergence of certain kinds of blogdom…personal voices in a more safe space, which sounds kind of lame, but something about that feels much better than Twitter. There’s something about the framing of a newsletter when it comes to presenting work on the internet that was really appealing to me.

Lenny Rachitsky: I also quit my job and I was just like, “What did I learn over these years at this company if I wanted to start my own company?” So I started writing notes to myself. And then that turned into kind of the cliché medium posts, but the medium posts did really well. So I switched to Substack. And initially, I never had any intention to go paid. It was not even a thought in my mind that I would charge people for anything I was writing. And then actually COVID hit and I was out of a job for a year, the market collapsed, and so I was like, “Shit I gotta try to make some money again.” And so, I tried this paid approach and it worked out.

Lauren: How do you decide whether to go the paid versus the unpaid route?

Lenny: I think there’s basically two routes. Either you want to make a full-time income from the newsletter, and if that’s how you want to approach it, then I think you charge. I think if you have another gig going, the newsletter is a really good way to give you new opportunities, get better jobs, learn about things. So the way I think about it is if you want it to be your main source of income, you should charge. Otherwise, you should not, because you lose in a lot of optionality and opportunity.

Lauren: Do you all agree?

Zach: Yes and no. I feel like they’re both still open because I have a freemium model, where one post is free to the whole list every week and then two others go out to just the paying subscribers. So there’s continual growth of the free list and then there’s more in-depth analysis that goes to paying subscribers.

Lauren: How has the pandemic shaped your writing? Clearly, Patrice, it was a real impetus for yours. But for the rest of you, has it shaped your process? Has it changed your content?

Edith: So I started it in December of 2019, and then the pandemic started. And I was trying to, hopefully, turn on the paid option right when everything was happening. And I was like, “Either this is gonna be terrible for me or possibly good because people will be at home more interested in consuming the kind of stuff that I’m creating.” But it did seem like a real terrible mistake, like I was gambling with my whole future and security—“What am I doing?”

But the stories I’ve been telling haven’t necessarily been about COVID; for the most part they aren’t. And I think it’s been an escapist place for people to read the stuff I’m writing about. But it’s definitely harder, because most of the most of my newsletter installments are little stories about my life and things I’ve done. And for a while it was pretty limiting because I wasn’t doing that much stuff.

Patrice: I had been toying around with the idea of doing a newsletter for probably a year or so. I had actually started a newsletter focused on myself as a writer and a black woman. At the end of March I sent it to my partner and one of my sisters and they were like, “It looks great.” But something was holding me back from sending it. I was like, “I don’t know if this is the time to publish it.” I had just resigned from BuzzFeed the past October and I really wanted to have a place where I could cultivate my own journalism audience and not depend on other publications to accept my pitches about black stories, and cultures, and communities.

Lauren: It seems like many of you did quit jobs to pursue this. Do you consider newsletters to be a side gig or a way to expand your audience? Or did many of you pursue this as a way to make a living?

Lenny: For me, I call it my “project: avoid getting a real job.” And it started off as a side gig, as “let me just see what happens with this thing while I explore startup ideas or maybe look for other gigs.” But then it just kind of kept growing. And so at this point, it’s completely my full-time income. And it takes maybe half my time. I don’t have any plans beyond this.

Edith: I am definitely doing this in an attempt to make a full-time living. And I am not there yet. But I’ve been trying to think in terms of two-year goals. So where I’m at right now, I’m not sustaining myself. But the trajectory would indicate that I could be there in about two years.

Lauren: Would anyone share what their income typically is from a month on Substack?

Zach: Right now it’s more than groceries less than rent.

Lauren: That’s a good barometer, I think.

Lenny: Mine’s at about a six-figure yearly income at this point.

Patrice: I haven’t charged readers yet—clearly, I need to talk to Lenny. What’s your subscription model?

Lenny: It’s a weekly email. If you pay, you get it every week. And then if you don’t pay, you get it once a month. And it’s about 15 bucks a month, $150 a year. And I find most of my audiences is tech professionals. So a lot of them expense it to their company.

Patrice: That’s a good market. [laughs]

Lauren: How do you all think about your audience? Do you have a particular demographic or a person you’re writing for? Do you have someone in mind when you’re writing your newsletter?

Edith: I don’t, which is hard. My newsletters are between 10- and 20-frame stories about something that happened to me recently. And it’s a little awkward for me because like I still treat it like a journal. But sometimes I’m like, “Oh, this is coming out kind of good. I think I’m going to publish this.” And then the tone shifts because I feel like I’m talking to someone instead of talking to myself. And that’s hard to preserve, and it’s hard to think directly about. So I’ll publish one story to every three that I feel came out the wrong tone or something.

Zach: So what’s interesting in this landscape that I’m covering is that it’s the convergence of a lot of different standalone fields in their own right: neuroscience, psychiatry, mental health, the healthcare system, clinical trials, FDA approval, and, obviously, psychedelics. I feel like the audience is people who are smarter than I am about all of these different things depending the topic for the day. And what that does is it forces me to reconcile with my imposter syndrome. There are a lot of readers who are literally experts on a particular domain, whether it’s medicinal chemistry or drug development. So it needs to pass the sniff test for them, but also be informative for readers who are not necessarily experts in that particular domain.

Lauren: Some of you are creating original content, some of you are aggregating from various sources. I know “creative process” sounds a little precious, but are there particular tools you find helpful in writing your newsletter, whether that’s online or off? What’s that process like?

Patrice: It’s evolving. So I’ve done aggregations. I did an original article about the history and culture of conspiracy theories in the black community. At the same time, I did an interview series called “Essential and Black,” because essential workers are disproportionately women and disproportionately black and brown people. I was like, “If nobody else is going to do it, I’m going to do it.” So I took money out of my own pocket, I paid some women illustrators to illustrate the essential workers who I profiled. It’s been a mix and I’ve been experimenting. I’m trying to work to my own perfectionism as I do my newsletter.

Lauren: Many of you are charging for your newsletters. Does that create a pressure to produce? Do you feel like you have to keep up a particular cadence? Do you feel like you should be doing more? What feels like the right amount to have some kind of payoff for your reader?

Lenny: I always feel like there’s this boulder chasing me for every week, for the next week. As soon as I put something out, I’m like, “Okay, what’s coming next week?” There’s no better way to motivate myself to keep going and writing. What’s funny with Substack is that people are buying these yearly plans. And so, in theory, I don’t think you can ever stop, unless you’re planning a year ahead.

Lauren: [laughs] The boulder’s getting bigger, Lenny.

Lenny: Yeah, but I think it’s a good thing, because it’s motivation. Otherwise, I don’t know if I’d keep going.

Zach: Every time somebody signs up for an annual subscription, you’re on the hook for a year from that day. One of the things I think a lot about is how the psychedelic emerging ecosystem could go downhill, because we’ve seen it in the past historically. And so I think about “How could the paid newsletter ecosystem go downhill?” And it could be that eople get subscribers and then they make ambitious plans and we don’t fulfill them. But it is a real motivator.

Lauren: How about you, Edith?

Edith: Yeah, when I switched to paid, I wasn’t really anticipating that it would make much of a difference. But it’s definitely a big deal because even if you’re just asking people to pay a penny for it, the whole experience changes. It becomes like, “Okay, this is something that if I fail to produce, I’m actually failing people rather than just like following my own impulses.”

I do it three times a week and I’ve been really struggling with what to send to people who pay for it and what to send out for free. Other people have lots of different kinds of advice about what I should do. Some people are like: “Give it all away for free.” “Don’t give any of it away for free, put it all behind the paywall.” “You should sell prints rather than offering a subscription.” “You should go to Patreon.” I just thought that it would be much more intuitive, but it’s just lurching constantly all the time. I’m trying to follow the NPR setup, basically, which is: if you’re enjoying this, please consider supporting it. I really struggle with the language. I didn’t think it would trip me up as much as it would, but I’ve never had to directly ask people for money before.

Lauren: Do you all hear from your subscribers? Are they like, “We love that one” or “We hated that one?” For those of you who have worked in media, how does it compare it to a traditional media following? Does it feel more intimate? Does it feel more niche?

Patrice: I don’t get comments, really. I get a lot of feedback on Twitter mostly, people who are supporting the newsletter by saying, “You guys need to read this and here’s why,” and sharing posts. But I don’t get as much interaction as I’ve gotten when I’ve worked at previous places. But, you know, the BuzzFeed audience is outspoken. [laughs]

Lauren: How about the rest of you? What kind of engagement are you seeing with your subscribers?

Edith: One of my favorite parts of doing this newsletter is that people write back to me over email, and it’s just such pure pleasure. I’ll share a story about my life and then someone will come back with a story about their life, and I just feel like I have all these ongoing conversations with people. And it’s so meaningful to me. I find that people mostly say supportive things. And if they have something critical to say, they mostly keep it to themselves.

Lauren: That’s a shift from traditional media, I would say.

Edith: Yeah, I guess there’s something about if you’ve opted into this, you can just opt-out if you don’t like it.

Lenny: With my newsletter, it’s positioned as an advice column for work, essentially. And so people are sending me questions all the time and then responding to questions I’m answering. And the thing that I realized recently is that there’s this really interesting community that’s created. The people that subscribe to the newsletter are really interesting, and smart, and doing really cool things. And so what I ended up doing is building a Slack group for paid subscribers. If you’re paid, you get into the Slack group.

And that’s turned into something really unexpectedly amazing, where people are asking questions, helping each other with things. There are jobs that have been found through it. I’m starting to think about taking content from that community and adding it to the newsletter to give other folks a chance to surface things they’ve experienced. And so that’s something I definitely recommend you guys do if you have a big enough subscriber base.

Lauren: How do you think about growing your subscribers? Do you think about branding? How do you promote your newsletter?

Lenny: For me, it’s essentially word of mouth, people sharing it with their co-workers and with their friends. I also use Twitter a lot. I find this really cool flywheel between Twitter and the newsletter, where I write a post and then I tweet the nuggets of the post in Twitter and give it away as much as I can. And people retweet that thing and then they follow the newsletter. So there’s just kind of a back-and-forth that happens.

Lauren: It’s a bit easier for you to say, Lenny, because you have a massive Twitter following.

Lenny: But it wasn’t that massive initially, it started small. And I built both platforms at the same time, where I started writing and then I tweeted the same idea. And it kept growing in both directions.

Lauren: How do you think about it, Zach? Because, as you say, you’re kind of coming into it new. How do you promote your newsletter?

Zach: The way I think about it is: it’s B2B, so it’s about the business and the policy of this emerging industry, but it’s also B to what I’m thinking of as, like, a fanatical C. This stuff has a lot of personal meaning for people.

It’s very much chaos at this point in this space. If we can combine a curational aspect with news and then linking them together and contextualizing it, then it gets shared. And so I started with posting it to LinkedIn— which, I’ve never used my LinkedIn profile at all.

Lauren: Did that work?

Zach: It did. Yeah, I was shocked. Because there’s a lot of early energy, people are looking for jobs, people are looking for investment, people are really hungry for information in this particular domain. And so even though it’s a small topic in the scheme of things, when people find it seems to have been readily shared. So then I just cut off all sharing on social whatsoever, just to see if it would continue to grow, and it continued to grow. I used that as a bellwether that I was onto something in the early days.

Lauren: How about you, Patrice?

Patrice: It’s interesting. Maybe the first or second week that I launched back in April, I saw that publications that target black audiences like Blavity, The Root, Black Enterprise, all covered the newsletter. I hadn’t even reached out to them.

It was just this one tweet that sort of got the ball rolling. Nicole Hannah Jones over at the New York Times, maybe mid-April, started tweeting about how the coronavirus pandemic was going to disproportionately impact black communities. And in the Twitter thread I was like, “Hey, actually, I started a newsletter about this in case anyone wants to check it out,” and put the link. The people who are following the thread and also responding are going to see that in the Twitter thread.

So, Adriana Lacy who works at the Los Angeles Times and who also has her own Substack newsletter called The Intersection—which is like musings about journalism at the intersection of tech and innovation—she saw my tweet and was like, “Hey, can I interview you for my newsletter?” She’s also a black woman, so let it be known that black women and journalists gave me the attention that really got the ball rolling with this newsletter. Nieman Lab reposted it, which got me whole bunch of other subscribers.

Lauren: That actually feeds in to another question I have for all of you. Does the newsletter community feel interconnected? In the way that there’s an influencer community on many other social platforms that kind of feed off one another, does the same thing exist in newsletters, or does it feel more siloed?

Edith: It does feel connected, to me. I think when I used to read blogs, the blogs would be visibly connected to me in my mind, as a reader. But now that I’m like a newsletter creator, I feel connected to other newsletter creators.

And similarly, that’s been my experience of growing the newsletter. I get my hugest bumps in subscriber rates after someone recommends it in their newsletter. It feels like a bunch of wheels that are layered on top of one another, Venn diagrams or something, and the spokes are often odd. The topics aren’t necessarily the same, but, like, I feel more connected to someone who writes about money in a newsletter than I feel connected to a cartoonist in another form, necessarily. And it’s been fun to talk about the business end of it and stuff like this podcast. We’re gnawing on the same bone, but from different angles. I find that to be a really nice point of connection with people.

Lauren: Having all had your newsletters for roughly a year or so now—some less, some slightly more—what do you wish you’d known in the beginning that you know now?

Lenny: I called mine “Lenny’s Newsletter” because I had no better name when I was signing up for Substack, and it’s like really hard to change later. The other is going paid is a bigger deal than you think. Now you’re committed to writing for a long time. And very few people see it, at least initially, only the people paying for it. I went from like thousands of people reading everything I wrote to a few hundred. And over time that builds again, but it feels really weird.

Lauren: How attuned are you all to how many subscribers you have?

Edith: Very attuned.

Lenny: Let’s not talk about how often we check our dashboards.

Patrice: I’m attuned also and sometimes it’s like, “Okay, how many followers do you have?” For me, I’m interested in how many people are receiving the things I’m writing and creating because my intention was to empower people with information and to make a difference.

At the end of the day, I think it’s cool to focus on a smaller following of more loyal people rather than a massive following of people who are tepid about what you’re doing. It’s more impactful and influential that way.

Lauren: In that your newsletter is more mission-driven, do you think you will monetize? You went the Patreon route. Can you talk about why you decided to go that route, rather than others?

Patrice: I wrote an op-ed for the New York Times about how myself and other black journalists are exhausted because we’re experiencing all these pandemics within pandemics, and they didn’t just emerge overnight. That, of course, got me a huge boost in subscribers and people just reaching out, “How can I support you?” This one woman was like, “I just wanna send you $300, how can I do that?” [laughs]

But I didn’t want to have that boulder, like Lenny was talking about, because I’ve had that boulder my whole career working in digital media. So with my Patreon, I was like, okay, well, this is a way people can support me individually and if I skip a week on the newsletter, it will still be okay. It won’t be these people paying and I’m not producing anything. I do want to pivot to a subscription model because I want to provide opportunities for other black journalists, to write the stories that they see are missing about black people within the pandemic.

Lauren: A lot of traditional journalists are being laid off now in the midst of a pandemic. Lenny, you mentioned tech. Academia is shrinking. I think a lot of newsletter writers are coming from a lot of different industries at the moment. Do you think this is part of the evolution of media? Do you think that this kind of niche community-targeted media is the direction we’re going? Or do you think that it’s tangential to traditional journalism?

Patrice: I think it’s the route that we’re going. Traditional media is changing. But also, look at the way that our society has become so fractured and so siloed in terms of perspectives. It’s like a snake eating its tail. I don’t think it’s going anywhere, especially because we have these tools where anyone can become a platform.

Lauren: My question for all of you then is: what is the draw of a newsletter compared to either traditional media or compared to social media?

Zach: The architype of a writer has been something that I’ve looked up to, but I never had the gumption, the courage, the orientation to go that route. So, for me, it was like, just start a Substack and then there’s no gatekeeper. I reached out to a handful of publications when I first got started and never heard back from anybody. So I just started myself. From the creator’s perspective, that to me feels significant. The internet allows a non-journalist to have a chance of creating something.

I haven’t figured out the art of Twitter. And so I want to reserve my energies for the writing and the newsletter, which I actually feel very comfortable with. I feel like that’s a medium that has this unique feature of being open because it’s over email. It’s not on a “platform” like Facebook or what have you.

Lauren: What’s your perspective, Edith?

Edith: A lot of this I did because it seemed to align with the kind of stuff I wanted to create, which didn’t totally exist. It’s like, I wanted to have it be comics, but also writing, with ways to link into other stuff. That wasn’t something I could pitch to a traditional media outlet.

One problem that I think about and would be curious other people’s thoughts on is: Is there a natural ceiling for this? I started following all these newsletters and I loved them, and then I became bored of them, and then now I get way too many. It really starts to add up very quickly. And I feel a sense of being one of those people. There’s like an audacity of, like, “Me, my voice alone is good. Please listen to it. Don’t listen to me on a team with other people, listen to me alone.” There’s a lot of talk about like a fostering community, and I think a lot of newsletters have done a good job with that.

That was like a big part of my favorite past job when I was running another website that was a community-driven site. And so I’ve moved on to this thing that’s not really community-driven. It’s just me creating and other people reading. I worry that the average person has an appetite for that, but will soon be exceeded by the amount of newsletters that are being created.

Lauren: Right. The question is, do you worry about newsletter oversaturation?

Edith: And specifically, the newsletters that are asking people to pay for them, like my own.

Lenny: Yeah, the way I think about it is: you can basically make a living off a newsletter if you have 1,000 to 3,000 paid subscribers. There’s a lot of people in the world that care about a lot of different things. The way I think about it is, what are the topics that people are interested in, especially if it’s professional, or something that they value enough to pay for in some way? And if you can be one of the better content producers in that vertical, I think you can make a living, and I think a lot of people can make a living doing that. I think there’s so much opportunity. I personally subscribe to 65 newsletters.

Lauren: How many of them do you read?

Lenny: I read most of them. I unsubscribe for the ones I don’t.

Lauren: As newsletter writers and readers, what are the main components behind a successful newsletter, in your opinion? The newsletters that you love, and read, and actively engage with, what makes those successful?

Lenny: I think there’s essentially five ways to provide value. What are the different types of newsletters? Entertain the reader, make them smarter about some topic, keep them informed on what’s happening, make them money, or make them feel like they’re part of something bigger. If you can do one of those things really well, consistently, I think you’ll have a really successful newsletter.

Zach: Do you optimize for one versus the other or do you feel like you’re kind of mixing and matching?

Lenny: I’ve been looking at newsletters to see if they generally fall in one of these buckets and I think generally, it’s just one.

Patrice: As someone who’s always interested in hearing from marginalized and underrepresented voices, I would advocate to put your unique vantage point on top of those different buckets, whichever one you fall into. Lean into what makes you different. A lot of times, that’s going to involve some transparency and being vulnerable with your subscribers, but I think that really resonates with people.

Lauren: One thing I’m interested in is it seems to me that media is shrinking somewhat, but also becoming increasingly personality-driven. How much of your newsletters do you feel is driven by your perspective, your personality, versus information-driven? And what’s the benefit of each?

Zach: I will say that my experience with that has been challenging. I think Naval Ravikant is credited with this quote of “Escape competition through authenticity.” Nobody can compete with you on being you. The early days of my newsletter were way funnier than they are now. And that that was a challenge. One, it’s really tough to keep it up. But also, as the audience grows, there’s a feeling of pressure. I’m sort of struggling with that. I think I’m coming back to that a little bit, offering more of my character, personality…cursing to readers. But that was really challenging. It’s like, “Oh, people are paying attention to this,” and now I’m shrinking in my authenticity.

Lauren: How do the rest do you think about how personality-driven your newsletter is?

Patrice: I don’t have a formula for mine. It really just depends on the tone. And like Edith said, subscribers don’t have to be there if they don’t want to. Which is great freedom for everyone involved. So, I don’t think there’s a right or wrong way to insert yourself.

Edith: Mine is definitely very personality-driven. it makes me feel close to other people in the ways that it plays out. But it’s hard, it’s intense and it feels very personal in a way where it’s hard to just do the work and do it well. It’s harder to step away from it because it feels like the camera’s very, very close to my face—which is exactly where I placed it. But I wouldn’t say it was necessarily the most sustainable business model.

Lauren: Lenny, what do you think about that?

Lenny: My newsletter is definitely information-driven. I try to balance “Oh, it’s Lenny’s newsletter,” with “Okay, it’s actually just a bunch of information that you can use.” But I find, similar to what Zach said, that it’s really important to be authentic and honest about what you’re saying and not just say things that sound good and things that other people have said. So whenever I write I try to, one, always include my perspective and my experience, but still focus it around information. And then, two, make sure I feel like this is real and honest and not just fluffy things that quickly come off as you’re writing. Often when something’s too easy to write, I’m like, “I don’t know if that’s actually true. Let me really think about this.”

Lauren: How do you think about competition? Your topics are all fairly niche. Is that by design? And how do you think about others in your space?

Lenny: I don’t spend a lot of time thinking about it. The thing I find though is most people just can’t keep it up. And so even if there is somebody that’s like, “Oh, wow, this guy is going to be even better than me,” oftentimes, they have other things to do. They have jobs they gotta work on. And so, a lot of it is just consistency.

Lauren: Outlasting the competition.

Lenny: That’s part of it, it’s outlasting. And then the other thing is, people just don’t have time to write newsletters well. And so if you actually have time and you don’t have a day job that’s sucking up all your brain energy and hours, you have a big advantage over a lot of other people that are thinking about it or trying to do it. Because in my experience, there’s a really direct correlation between the hours I put into a newsletter and how well it does.

Lauren: It’s tricky, you’re gonna recommend a lot of people quit their jobs and start newsletters. [laughs]

Lenny: There’s a lot of benefits to having a job. Health insurance, for example.

Lauren: Zach, are you a full-time newsletter writer or do you have a day job?

Zach: I’m an acupuncturist and we recently moved from Brooklyn to Portland, Maine about a year ago. So I was in the process of getting a new practice up and running in March of this past year, and then I had to shut it down. But I very much intend to be doing this full-time as soon as I can. And I think I could probably get to that point in the next year and a half to two years.

Lauren: Patrice, how do you strike that balance, in that this is not your full-time gig? How do you strike the balance between making a living and this newsletter, which started out as kind of a passion project?

Patrice: I freelance, but that’s more writing. And from someone who’s burnt out from writing, it’s a lot. So, yeah. I’m figuring it all out as I go.

Lauren: How would you define success when it comes to your newsletter? So, what’s the point you’re aiming for when you’ll be like, “I’ve made it. It’s a successful newsletter.” Or if you’ve reached that point, how long did it take?

Lenny: I’ll say, for me, there’s the financial goal and then there’s the emotional goal. I’d say financially, it’s when I can get past the salary that I had in my last job. Then I would feel like, “Holy shit, this is crazy, and real, and I could stick with this for a while.”

Lauren: Have you done that?

Lenny: I haven’t done it yet. And then emotionally, I think it’s just consistently feeling people are getting value from it by emails I get, and replies, and tweets, and things like that. As long as it continues, I feel like I’m on the right track.

Edith: Yeah, I really like that answer. That that speaks to my experience too, which is that it was emotionally fulfilling pretty much right off the bat. And financially, my goal is to get 1,000 paying subscribers in one year and 2,000 by the end of the second year. I’m like halfway to the first, so just shy of 500 paying subscribers. But I kind of like the previous salary thing. That’s a nice benchmark.

Zach: 1,000 True Fans is like a mantra for me, trying to get to that point. I think that’s a real proof of concept.

Lauren: How close are you to reaching that benchmark?

Zach: Not close. But I think I can do it in 12 to 18 months. But then there’s also this idea of optionality. I set out with the intent to create an opportunity for myself in this emerging space. And the at-bats that I have on that front, that are creating something analogous, that would allow me to keep writing, but also provide some sort of steady income, that seems to be getting closer. And they’re getting more substantive. So those are the two frameworks that I’m using.

Lauren: Patrice, do you have a perspective on that?

Patrice: Ideally, you know, it’s so successful that there’s no longer a need for it because there’s no disproportionate impact. And hopefully my newsletter contributes to that in some way. Hopefully, it allows someone to avoid getting infected or to better care for people in their community once they’re diagnosed with it.

Lauren: In our last couple minutes, I’d like to do a lightning round. What are some of your favorite newsletters?

Patrice: I really like Darian Symoné Harvin’s Beauty IRL. It’s a deep dive into beauty, the same way people do deep dives into politics and other hard news. Carefree Black Girl by Zeba Blay. Maybe Baby, it’s this writer she was at Man Repeller and she left and she started her own newsletter. It’s just musings on what’s happening in her life. The common thread is millennial women being transparent about the way culture and society are impacting their life and perspective.

Lauren: Zach?

Zach: Stratechery by Ben Thompson is one. Bill Bishop, who’s like the OG Substack writer writes a China newsletter that’s been motivational for me. There’s another guy, Jacob Donnelly, who writes a newsletter called A Media Operator. It’s about operating a media company, but he’s a one-person operation himself. So it focuses a lot on the solo creator. Anthony Pompliano has got a good one. Andrew Sullivan just switched over to Substack, so that’s a full circle there.

Lauren: Edith?

Edith: I really like The Browser, which is a selection of stories from around the internet every day and they’re always from really weird corners. There’s a British writer, Ian Leslie, he has a personal newsletter. He recently switched to Substack. It’s called The Ruffian, it’s selections of his own work, but then also stories he finds online, and I really like his tone. I like Craig Mod‘s newsletter. He’s in Japan. He’s a photographer and it’s sort of like personal musings. There’s an antique jewelry newsletter that I love. My friend Monica McLaughlin runs it and it’s called Dearest. It’s also on Substack. And then a daily newsletter I really like that I’ve contributed to in the past is called Why Is This Interesting? And it’s just different stuff every morning.

Lauren: Lenny?

Lenny: 2PM by Webb Smith talks about DTC ecommerce, a really good newsletter. Li Jin has an awesome newsletter about the Passion Economy, and now she has like a video series every week where they interview someone in the Passion Economy. Alex Danko has an awesome newsletter about tech and trends and things like that. Turner Novak, who’s a VC, he has a great newsletter which goes deep on various companies like TikTok and Pinduoduo. Nikhil he has this great newsletter called Next Big Thing. Alex Kantrowitz left BuzzFeed and started a newsletter called Big Technology, where he writes about tech. Polina has an awesome newsletter called The Profile where she profiles successful people. There’s also The Everything, which has a lot of great content. And there’s also one called Not Boring that’s not boring and great that I recommend.

Lauren: Great title. Well, thank you all so much for joining us on a16z Podcast.

Patrice: Thanks

Zach: Thank you.

Edith: Thank you.

Lenny: Thanks for having us.

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