Paid Newsletter Deep Dive: How Lenny Rachitsky Gets 18k People to Pay for His Content

This is Part 2 of my deep dive into Lenny Rachitsky and how he’s built his newsletter. In the first part, I covered how he’s been able to grow his newsletter to over 377k people. If you missed that issue, you can go back and read about Lenny’s Newsletter growth here.

Lenny Rachitsky makes over $2 million from premium subscribers every year.

Today, I’m covering how Lenny has been able to turn a meaningful amount of those people into paying customers.

He has over 377k free subscribers, and over 18,000 paid subscribers – which means he is able to get between 4-5% of all subscribers to pay for a subscription.

But how does he do it?

How Lenny Converts Free Subscribers Into Paying Customers

If you’re even mildly interested in running a paid newsletter, or even just how people grow paid newsletters, buckle up. You’re in for a treat.

1. The launch plan for the paid newsletter. I found the full launch plan for you guys. And there were some things missing that you can add to it.

2. Starting small. While he has a ton of things included in the paid subscription now, at the beginning that wasn’t the case. And for good reason.

3. Making the community a “no-brainer”, and how he naturally promotes each piece. The components of Lenny’s paid newsletter and community at this point are just silly. He could easily charge $500-$1,000 per person and have no problem selling a similar number of seats.

At the same time, Lenny is the opposite of someone who will write a tweet trying to sell people into buying a subscription. But he does promote them in really subtle, genuine ways.

4. Retention of paid subscribers. Arguably the most important piece is keeping people around once they sign up. And Lenny does a lot of smart things to do that.

1. The Paid Newsletter Launch

Lenny launched the paid side of the newsletter on April 7, 2020 after he had written the free one for 9 months.

But he didn’t just turn on the paid subscription and call it a day. There was a good amount of thought that went into this launch.

Lucky for you I found the layout of his actual launch plan.

It’s actually quite simple really, and he could have made this a lot more complicated leading up to it, but I like how well this worked out for him.

Seeding The Launch With Influencers

Lenny knew he needed to get some initial traction from some big names to help turn this into a successful launch. He enlisted the help of some friends and others he’d interacted with in hopes they could give it a little push.

Li Jin and Nathan Baschez were two of his friends from the Type House community that I covered in part one. They’re very well respected in the newsletter and online community space.

Andrew Chen was the one who convinced Lenny to continue writing in the first place, and helped him by publishing a guest post on his own blog. It doesn’t hurt that he’s a big name at a16z either.

James Beshara had Lenny on his podcast in 2019 to talk about one of his super in-depth research articles. He has a very engaged audience and runs his own startups.

The night before the launch, he emailed some of these folks and let them know it was coming and that he’d appreciate any support they could offer:

I’m sure there were more, but these were the main ones I could tell were explicitly sharing and supporting him on day one.

I can’t tell if these were planned, but people like Julian Shapiro and Hunter Walk also tweeted about it.

The Launch Email

Lenny seemingly spent a lot of time coming up with his launch email.

There are components he explicitly calls out and I tried to add some additional ones here:

There are a lot of pieces to this announcement email, but all in all, he answered the who, what, when, where, why, and how of the transition.

He also gave everyone a 2-week heads-up, which I think was more than fair.

This created a little runway for him to put out content reminding people about the upcoming change.

However, once Lenny sent out that launch email, this was the first reply he got back:

Make sure you have your thick skin when you’re going to launch anything, especially something that people have been enjoying for free for months.

I’m sure that didn’t feel good, but overall, it only went uphill from there.

The Launch Tweet/Thread

After he turned on paid subscriptions and send the email out, he posted this thread:

He got a ton of great comments, and replies of people supporting the decision.

He also replied back to every single person who tweeted that they had signed up for the paid subscription.

The Next Day: Follow Up On Twitter

The next day, he was back at it.

He retweeted the original post, said thank you, and reminded people that the 48-hour discount was ending.

Early Growth Numbers

After 6 weeks, Lenny had 450 paying subscribers to the newsletter, and 13,000 free subscribers.

He saw a lot of subscribers come in in the first week of implementing the paid newsletter.

He also saw a really meaningful increase in free subscribers when he implemented the paid option.

2. Don’t Add Everything At the Beginning

You don’t have to start a paid newsletter with all of the bells and whistles.

And it honestly seems like that could be more painful for you to stay consistent with it.

Starting Small

When Lenny launched the paid newsletter in April 2020, he did it by adding some content behind a paywall. He wasn’t promising a community, or podcasts, or extra stuff in the beginning.

He talked about a future community and AMAs but didn’t start that right away. This helped him get his bearings and learn how to run a paid newsletter before adding all the bells and whistles.

3. How Lenny Makes Joining a “No-Brainer”

I know I said that he started small when he launched — this is no longer a “small” operation.

Here are some of the important pieces of the community and paid newsletter now, and how he promotes each piece to get people over the edge and joining the group.

Slack Community

When you join Lenny’s newsletter, you get access to a Slack community where people can engage with one another and ask questions.

It takes a few days to get access to, but there is a lot of cool stuff in there. And the caliber of people in that group is pretty phenomenal.

Some of the fun channels I saw in there were:

  • Newsletter focused one
  • A space for short-term gigs
  • A book club
  • A space for newsletter creators
  • Tools and pro tips

There are all kinds of stuff in there that would be interesting and relevant to someone in product management or early-stage startups.

In-Person Meetups

Within that Slack community, are location-based groups and a lot of these micro-communities get together in person every so often.

I see 75 of these, including 2 that are for virtual meetups. So 73 places around the world are able to come together and talk about their local spots, and get together to have friends who understand their work.

That is super powerful.

Lenny will post pictures of those in-person meetups on Twitter, and once he does there are always lots of people asking how they can join the Slack group.

Of course, the Slack group is a benefit only for paid members.

So by posting these photos, he’s building FOMO for his readers and getting people interested in joining the paid side of things.

Here is another example of him posting pictures from these meetups.

The other way he promotes the community, which is super subtle but really smart, is by adding it to the menu on his newsletter.

Whenever you’re scrolling around, reading a post, or just on his site, you see this tab staring at you:

Once you click it, you’re taken to a page that explains what the community is, and talks about these in-person meetups. He then includes pictures of recent ones as well.

Super smart on his part.

Not pictured, but also important, is that he includes some testimonials of how it’s improved people’s lives.

It again, makes this one part a no-brainer, let alone everything else you get with the paid subscription.

Fireside Chats/AMAs Within the Community

Lenny also has big names in the product industry who do AMAs within the paid side of the newsletter.

He promotes them on Twitter, as well as in the podcasts themselves.

Lenny interviewed Casey Winters (@onecaseman on Twitter) and the podcast episode went live on July 21, 2022.

At the beginning of the episode, he shares that Casey is going to be doing an AMA inside the paid community on August 5th.

Someone then asked him on Twitter where they could get access to it, and he retweeted that with the details.

Casey Winters is a massive name within the product space, so having access to be able to ask him a question is a no-brainer for people in that industry.

This is just one example of an AMA. But he’s had dozens of industry leaders on to chat about specific topics.

Open Threads in the Community

Lenny also does what he calls “open threads.” Essentially he’ll ask a question to his community and everyone can answer.

These seem to do two things:

  1. Let people feel more connected to him. He’s in there answering comments and providing feedback
  2. Give Lenny some cool data and insights into how companies are running. As well as what his community might be struggling with.

Either way, people seem to love them and they all have a lot of engagement on there.

Directory of Product Coaches

There is also a curated list of product coaches that you get access to when you join. Essentially, these are people who have been doing this stuff for a long time and have the experience to teach others.

They are vetted, so you’re not just picking a random job coach to help you out here.

Considering coaches often cost thousands of dollars, choosing the wrong one would be way more expensive than spending $150 to join Lenny’s newsletter.

Community Resources

There are quite a few other community perks you get access to when you join. Some of these include:

  • A directory of recruiters. If you’re looking for a job, or need help filling a position these people can help.
  • Hand-curated content on a lot of subjects. Some of the members of the community even curate these resources as they’ve been helpful for them.
  • 20% discount on all job postings – this one pays for itself (another no-brainer) if you were looking to post a job.

There’s a lot going on in there: everything from resources that help if you’re just getting into product, to advice on very specific questions and situations.

Software & Tech Tool Discounts

As a member, you also get access to over 100 deals and discounts on tools and software. Here is the list of categories you can filter through.

I didn’t want to call any specific ones out, because I wasn’t sure how proprietary that information was. But there are some good ones in there!

As someone who’s not even in this space, I found some discounts in there that I plan to use here shortly.

Community Wisdom Posts

The Slack community has a ton of valuable information in there. But as busy people with demanding jobs, you can’t always stay on top of the conversations that go on.

Each week, Kiyani, who works with Lenny, goes through the Slack group and pulls out the most interesting threads in there.

These get sent out every week to the paid subscribers, so they don’t even have to worry about missing something in the group.

I freaking love this idea.

Communication platforms like Slack and Discord can be so hard to keep up with. Having a summary sent to you each would be such a time-saver and helps people feel like they’re not missing out on a valuable piece of the community.

Keeping the Free Content Excellent

Lenny talks a lot about how you want to keep the free content you’re giving away at a really high caliber. Now, of course, all his content is pretty awesome, but the free stuff is what is going to do the marketing for you every month.

If you have 377k people getting a piece of content and it’s not good – not only are they not going to join the paid side of things, but they’ll probably unsubscribe altogether.

Since that’s the only post a majority of your subscribers see every month, it needs to be really good to get them to even consider paying you.

He chooses wisely what he’s going to put behind the paywall each month and what he’s going to give away for free.

I’ve heard this from a number of other people running paid newsletters as well.

Promoting the Paid Only Posts on Twitter

This is one of my favorite ways Lenny uses social to drive paid subscribers.

Here’s a great example of how Lenny takes a paid post, something only subscribers can read, and turns it into a thread on Twitter:

But, if you click the link in the thread and go to the article, and you’re not a paying subscriber, this is what you see:

So while you get a cool summary on Twitter, if you want more information or to read into the data a little more, you’re going to have to sign up.

He does these a lot, and if the topic resonates with you enough, you’re going to go pay for it. Especially if it’s going to make you better at your job.

He also was tweeting about subscriber-only posts on Twitter and they seemed to be working.

He turned this one into a thread about some of his favorite flywheels, and then I saw this comment below.

FOMO at its finest.

4. Retention for a Paid Newsletter

Getting people excited to join your newsletter is just one piece of the puzzle. If you’re not focused on keeping them around and excited to keep paying you, things can fall apart pretty quickly.

The best products and communities start focusing on this right away.

One of the ways you can make people feel like they made a good choice is within the first few minutes of signing up.

Welcome Email

The job of a welcome email is to assure someone that they made the right decision in buying from you.

Lenny does a great job with his welcome email, and he’s said that he’s seen so many people copy it exactly.

It’s straightforward but gives you links to all of the big pieces you need to get started with the paid side of things. And those community links make you realize just how much valuable content is behind the paywall.

It’s like an instant “ohhh, this was totally worth it” moment.

Building Community

Making people feel like they are part of a community seems to be a huge priority for Lenny.

Through the months and years of running this paid newsletter, Lenny tries to make his subscribers feel like they are part of something bigger.

Here are a few examples that I love:

Lenny’s NFTs

At the height of the NFT boom, Lenny made 40 NFTs of people in the community who have helped him along the way or were most active.

How cool would it be to wake up one day and Lenny has enshrined you into an NFT just because you were active in his community?

Even if you’re not into that kind of thing, it would be cool to be recognized out of thousands of members.

That would make me a lifetime member for sure. And it shows others that he appreciates and incentivizes being active there.

Free Stickers

Some of the biggest newsletters run referral programs where if you refer someone you get a free sticker.

But what if Lenny just sent you one in the mail just for being a part of the community?

Lenny did that when he started the stickers. But they also get handed out if you attend a local in-person meetup.

These might not seem like a big thing, but people love getting recognized and feeling like they are part of a community.

Answering Reader Questions

Lenny’s newsletter is that it’s like an advice column for product people. You can submit questions (anonymously if you want) and Lenny might answer them for you.

Having your question chosen out of tens of thousands of submissions has got to feel good. So the inherent nature of the newsletter is building community and trust.

Knowing that this “celebrity” in your industry took the time to read and research a meaningful answer is pretty cool. It’s also kind of like realizing he’s not lip-syncing and can find answers to your specific question.

Of course, you have a be a paid subscriber to read most of the answers.

Continuously Improving the Paid Subscription

I mentioned he started small so he knew he could keep up with the paid side of things. But slowly, he started adding in all of the components I listed out above.

While we see the finished product now, it didn’t start that way.

And honestly, it’s been a way for him to keep talking about the premium membership.

When he adds something new, he can tweet about it and get people excited.

The Downside to Paid Newsletters: A Boulder Chasing You Down a Hill

Lenny says that one of the main cons of running a paid newsletter is that it feels like he’s always being chased down a hill by a boulder.

People are buying annual subscriptions every day. If he ever wanted to stop writing, he either has to give a year’s notice or refund people who have recently purchased an annual membership.

This is a good thing and a bad thing in the sense that it keeps him writing all the time, but also feels like he can’t stop.

From what I can see, he really enjoys running this community, so I doubt this will be an issue for at least a few more years, but who knows?

Writing this piece got me really interested in paid newsletters. Do you run one? What are some of the other ways you think these can be improved upon?

I’m always up for a chat. Reach out on Twitter or LinkedIn and let me know!

chenell basilio

Chenell Basilio

Chenell is the head writer and reverse engineer at Growth In Reverse. She spends her days researching newsletters, audience growth, and generally figuring out how to help others create better content.

She has an almost useless Bachelor's Degree in Geography, enjoys running, listening to podcasts, and eating guacamole. 🥑

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