Lenny Rachitsky: The Man Who Built His Email List to Over 377k

Lenny Rachitksy makes millions of dollars a year with his paid newsletter.

He left Airbnb in 2019, thinking he was going to build a startup. But after writing an article on Medium that went semi-viral, a friend convinced him he needed to keep writing instead.

Here’s how he went from having no email list, to building one of the top newsletters on Substack.

how lenny grew his newsletter

How Lenny Rachitsky Makes Money

Lenny has an incredible business and makes money in a few different ways. And the final amount is a mind-boggling sum of money he’s able to bring in from this business.

Paid Subscriptions

The bulk of Lenny’s revenue comes from paid subscribers. He runs a newsletter, aptly named Lenny’s Newsletter, that has a free version and a paid version.

Subscribers can either pay monthly, at $15/mo, or pay for the year upfront at $150.

Lenny also has the “I Can Expense It” tier, where you can pay $300 and support his work in a more meaningful way since you’re not personally buying it.

There are also group options for companies that have larger teams that want access to this information.

Lenny has 377,000 free subscribers to his newsletter at this point.

From past numbers he’s shared, he converts anywhere from 4-8% of these people into paid subscribers.

Let’s go with 4% to be conservative.

377,000 x 4% = 15,080

At an average of $150 per paying subscriber, that leaves us with:

15,080 x $150 = $2,262,000

But Substack does take a 10% cut, and he has to pay 3% in Stripe fees on top of that.

So after fees but before taxes, Lenny’s revenue from the newsletter is probably around:

$1,967,940 per year

Mind you, this is from his newsletter alone.

Podcast Sponsors

Lenny launched a podcast, aptly named “Lenny’s Podcast” in June of 2022.

His podcast is free for everyone to listen to, and instead is supported by sponsors. And they aren’t cheap sponsors either.

Lenny’s podcast is sitting at #25 in the Technology category on the Apple podcast charts.

Lenny has said that his podcast will outearn the newsletter in its first year.

Let’s go ahead and guesstimate that he’s earning another $2 million from the podcast.

$2 million per year

Job Board

Similar to other VC and technology newsletter writers, Lenny also has a job board. And a quite expensive one at that.

There are only around 17 jobs on the site at this point, but it is a time when a lot of tech companies are laying people off, so I’m sure this looks a lot more robust around other times.

He does donate a portion of these proceeds to non-profits in the tech space, which is nice to see.

Lenny is also building a talent collective, where he brings together the top people in his community (you have to apply) and companies come to him saying they need a designer. He then links that company with the list of designers that would be a good fit.

Angel Investing

Lenny is an angel investor, and his audience has given him access to quite a few deals as well.

Here is a list of some of the companies he advises and invests in:

I know very little about angel investing and the returns he is expected to get from these, so I’m going to see myself out when it comes to guessing at the revenue he’s getting from these.

I think it’s safe to assume Lenny is pulling in a bare minimum of $4 million per year from his newsletter, podcast, and job board alone.

The Growth Timeline of Lenny’s Newsletter

Lenny’s growth timeline is pretty consistent with his Twitter growth, until April 12, 2022.

That is the day that Substack launched their recommendations feature.

Essentially, other Substack writers can recommend Lenny’s newsletter when someone signs up to their email list.

I’ll talk more about this later in the post, but because that feature isn’t easy to replicate, I’m going to focus the rest of this deep dive on his first 100k or so subscribers — up until the point of that wild growth curve.

Everything almost looks like slow growth when you’re looking at the full timeline, so I wanted to zoom in to what it looked like before that.

The Growth Levers of Lenny’s Newsletter

There are a few main growth levers that Lenny has benefited from and use to grow his audience to the massive size it is now.

1. Getting in front of other audiences. Lenny came out of the gate running because of a few key places he posted his writing.

2. Deep research on the industry. The quality of Lenny’s content is incredible compared to what else is out there for his readers. He figured out what people wanted, and spent a ton of time creating it.

3. Substack Recommendations. This wouldn’t be complete with out at least a mention of the way Lenny has been able to grow his audience since Substack launched their recommendations platform.

4. Twitter Flywheel. Lenny isn’t a “thread boi,” but he’s been able to sustainably grow his audience and convert those people into subscribers.

Let’s dive into each one and break down his growth.

1. Getting in Front of Other Audiences

The first post Lenny wrote online in 2019 was on Medium. He had recently left Airbnb and wanted to remember the top things he learned while working there.

He said he didn’t think anything of it – but apparently, a lot of other people did.

This post got 29,000 “claps” which are similar to likes.

The CEO of Airbnb shared it with the entire company in an email.

Lenny was planning on starting a company, not building a newsletter. He wrote a few more articles on Medium, and those did pretty well also.

But his friend, Andrew Chen, told him that it’s rare to find something you love doing, that the market also loves.

He told Lenny to double down on it.

Lenny stopped writing on Medium and started his own newsletter to share his ideas.

He went back to all of those posts and added a line at the bottom letting people know about his newsletter.

That got him his first 100 or so subscribers.

He was able to use the audience that Medium was able to provide him to move people over and kickstart his email list.

Nowadays, I don’t think Medium sends you the same amount of traffic like they used to, but

Guest Posting

That same friend, Andrew Chen, had his own website and newsletter. Lenny was telling him about an idea he had for an article, and Andrew really enjoyed it.

Andrew loved the idea for the post, and told Lenny he should publish that on his site as a guest post instead.

Lenny agreed.

If you’re not in the tech space or VC world, you might not know who Andrew Chen is. But he is now a partner at Andreessen Horowitz, a major VC company.

Andrew had quite the following — so when Lenny wrote that guest post, it sent him subscribers.

Around the same time, Lenny wrote a post for The First Round Review. These two guest posts got him to 1,000 subscribers.

2. Publish Quality Research

Stick with me here. This isn’t just a long way of saying “write great stuff.”

I know a lot of people scoff when people just say to create quality content.

But there are a few examples where Lenny does exactly that, and it has a measurable impact.

Example 1: Deep Industry Research Report

The first example comes from November of 2019 when he published this post:

He said he did this research because he’s often asked what Airbnb did to grow it into what it is today. While he can give them advice on what Airbnb used, he finds that aggregating advice from multiple companies can lead to better advice.

He couldn’t find anything like that, so he decided to do the research himself.

Lenny spent months interviewing top names in the industry from leading product marketplaces like:

  • Uber
  • Angel List
  • Thumbtack
  • Eventbrite
  • DoorDash
  • Caviar
  • Zillow

He interviewed around 25 people from 17 marketplace companies to come up with this research.

This was a huge undertaking, and needed to be broken out into a 4 part series that he published on these dates:

  1. November 20, 2019
  2. November 22, 2019
  3. November 25, 2019
  4. December 3, 2019

This massive research project led to around 2,000 more subscribers.

And just remember, he only had around 2,800 subscribers when this went live, so he almost doubled his subscriber base from one article.

But, I think he’s not taking into account how much faster his newsletter started growing after that went live.

Look at the trajectory of growth before this went live, and then afterwards. His growth definitely sped up quite a bit after that was published.

Here are the reasons I think that happened:

  • Respect for Lenny went up because they saw he would put in the work to publish something like that.
  • This content was hyper-sharable because it was the ultimate guide to growing a marketplace.
  • It started a flywheel of people sharing and finding his content
  • Because he put them out in a series, people were subscribing to make sure they didn’t miss the next piece.

All in all, Lenny did the work that most people aren’t willing to do.

Example 2: First 1,000 Users

Clearly, he saw how big of an impact that first one did, because he did it again with this next article.

Lenny spent a month putting this research together by:

  • Interviewing founders
  • Scouring interviews he found online
  • Asking Twitter

That last piece is really interesting, because the amount of feedback he got was incredible. Here is the tweet:

The engagement on here is mind-boggling, considering he had 15k Twitter followers at the time.

He got comments from huge names in the startup and business space. Like the co-founder of NextDoor, and the founder of Loom.

And the best part about this Twitter thread, was that he was able to go back the day he published the full article, and drop a link there.

With 116 likes on that, I bet he got at least 300 people reading that article and was able to get initial interest on that post moving.

The only thing I think he could have done better than this, would be to take a page out of Jesse Anderson’s book and post a thread about what he found in that research and then link to that in these comments.

But it didn’t matter, this post again gave him a huge boost in subscribers.

He gained more than 5,000 subscribers from that second post over the following 2 weeks. That’s insane.

Lenny’s advice after all of this?

Keep writing great stuff every week, and then work on something epic in the background.

3. Substack Recommendations

As I mentioned above, Lenny himself has even said that Substack recommendations are now driving a majority of his new subscribers.

He had around 111,000 subscribers in April 2022.

In less than a year he’s been able to triple his subscriber count and is now at 377,000.

There are now 1,000+ other newsletters that recommend Lenny’s when someone signs up to their list.

A thousand.

He was definitely at the right place, writing long enough to be trusted, and stuck it out for the right amount of time.

4. The Twitter Flywheel

We talked about some of the ways Lenny has been able to grow his newsletter with Twitter, but there’s more to the story.

He’s not someone who posts on Twitter daily, methodically posting threads that go viral about Google chrome extensions.

But he’s sustainably grown his audience there, and has a really high quality following.

Lenny’s Twitter Strategy

For the most part, Lenny does a few things consistently within this flywheel.

For every post, he creates a thread around the topic. He likes to give away all the best stuff from the newsletter in the thread.

While most people might tease the ideas that are in the article, he just explicitly calls them out. If someone’s interested after that, they’re going to click the link and read the post.

But if you beat around the bush, people aren’t going to be interested, and they won’t click to read it anyway.

Find Multiple Angles on the Same Topic

Instead of just tweeting about the post once, he’ll find a few different ways to promote it.

One might be a thread with the main topics, and the next might be a single tweet talking about the big idea, or going deeper on one of the main topics.

Here’s one example where he posted two threads in the same day promoting the same article.

Two Threads in the Same Day

On December 10, 2019, Lenny published an article about how to tell if your marketplace is supply or demand constrained. You don’t need to know what that means, but how he promoted it was interesting.

In the morning, he posted this thread:

It’s actually a thread below that first tweet, and he goes on to share the learnings he had, and a few quotes from people who helped.

It did alright, but I guess he wasn’t happy with it, or just wanted to test a different thread.

Later that day, he posted this thread:

It got double the engagement, and still linked to the main post at the end. I’d be so curious to see which one drove more subscribers or clicks over to his website.

Tagging the People Who Helped

A lot of Lenny’s articles feature quotes and input from people who helped build some of these startups and companies.

He posts a lot of threads and tags those people as well. Here’s an example where he used quotes from a few different people who helped with growth. In each piece of the thread he tags them.

In the very last post of the thread, he drops a link to the full post for people to go read more:

Crowdsourcing Data

The way Lenny asks Twitter for information my little nerdy brain so happy.

Lenny went on a tweet binge asking for feedback around tool stacks of different type of people in his audience.

He’d ask for the tools Founder use, and then curate the answers:

He did this again with product managers, designers, and then he even did it again with founders, but this time asking what they buy in the first 1-2 months.

You want to know why I think this is so brilliant?

He’s getting other people to comment, and most of the time they tag the company or brand who built the tool. Those companies come and comment on the post, which can lead to even more visibility.

But he’s also getting access to data he can use in future reports.

He can go back and tag those folks who gave him the specific data, and then cycle continues.

How You Can Replicate Lenny’s Success

Let’s be honest, there is only one Lenny Rachitsky.

You won’t be able to grow like he has, he’s a once in a lifetime type of Substack growth case study.

But, there are things he’s done that we can absolutely learn from.

Guest Posting

We’ve seen other people do this, and it can absolutely help you grow. I’m working on this at the moment, so I’ll keep you updated on the results 🙂

While any guest post can help you get your name out there, you want to focus on ones with a decent sized audience of people who are in your audience.

The goal here is to get in front of people who are interested in what you have to say and a percentage of those readers will join your email list. Just keep that in mind.

Publish High Quality Content

Two of Lenny’s posts in the first year drove 50% of his email subscribers.

Read that again.

The two he spent months creating at the ones that had an outsized impact compared to his normal weekly content. Think of some of the data you wish existed for your industry, and then go build them.

Lenny’s motto is create good content every week, but be working on something epic in the background.

Swapping Recommendations

While you can’t expect the same outcome from Lenny’s Substack recommendations luck, you can still implement something similar

Beehiiv has a built-in recommendations platform where you can recommend other newsletters on their platform.

Sparkloop is a great option for you if you’re on another platform like ConvertKit.

And of course, Substack has its own for people who write on Substack.

No matter which platform you choose, reach out to folks and see if you can swap with others.

I did this using a tweet and asked if anyone wanted to swap.

It worked out pretty well. So even if you don’t think you know people who are willing to swap, I bet you can find some that way.

How Lenny Grew His Paid Subscriptions

In April of 2020, after writing the newsletter for free for 9 months, Lenny launched a paid subscription.

He’s now making more than $2 million per year from this alone.

But how has he been able to get people to sign up, and keep them from canceling their subscriptions?

That’s a whole story in itself, and you can read it here.

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. 🥑

Where I hang out on social media: