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Uncommon Conversations: An Interview with Lenny Rachitsky, author of Lenny's Newsletter

Lenny Rachitsky, creator and author of Lenny's Newsletter and the "Friends of Lenny's Newsletter" community, chatted with Uncommon about the inspiration behind Lenny's Newsletter, how the community got started, the added value community can bring to its members as whole, and what responsibility hosts and companies have to their communities.

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Our interview has been edited and condensed for clarity. Get the full conversation on YouTube.

Rebecca: Lenny, you were a leader in community at Airbnb, and now you host one of your own…How do you think about community as a space? Do you see that role function intersecting with the role of PM?

Lenny: Actually, at Airbnb I was the head of the community product team and our job was to build the host community and strengthen the host community itself, so I've been thinking about this stuff for a while. If you think about it, community as an area to invest is not new in any way. Flickr, I don't know, 20 years ago was a big community-driven business, and then I think eBay comes to mind as very community-driven for better or worse. So I don't think it's a new thing.

I think what's new recently is it's becoming a lever within B2B businesses, especially where people find that if you can build this kind of evangelized group around your product, there's a lot of opportunity there. So I think that's an ongoing thing. I think the other issue with community, and challenge in general, is it's always unclear what you get out of it. It's always like you have to battle within a company to convince them that it's worth investing in community.

And the thing I find that that works is, it only really works long term if the founders really believe in the need and the value of building community around your product. What I think is important - if you have a community - is to use it as a place to understand what problems your customers are having and what needs they have.

I find rarely does a product end up being the best driven by just a consensus amongst community. So I think it's important to think of community as a source of information, not a source of solutions and answers to your problems.

Your newsletter, Lenny’s Newsletter, has
more than 115,000 subscribers. What inspired you to start writing it?

[The] newsletter gives me an excuse to learn things that I don't already know and synthesize them and share them. Plus there's just so much fulfillment in sharing with other people and helping people get better at their work, helping them build their business, their communities, and things like that. So it's this win-win of getting to learn about stuff and then sharing that learning with other people and the fulfillment that comes from that. So it's pretty extraordinary. I’m very lucky.

[It] was a very unexpected path, and the way it happened is I left Airbnb about two and a half years ago now and I was planning to start a company. I had a big spreadsheet of ideas that I was working through and exploring them one by one - sorting them by which one's most likely to succeed and which one I'm most excited about and things like that.

In parallel to that, I started writing down things that I learned over my time at Airbnb and at other places so that when I started this new company, I [didn't] just start from scratch and I [could] build on the learnings of this last experience. That turned into a medium post which I just [thought], like, "Hey, this is useful to me, maybe it'll be useful to other people." That just did incredibly well, much better than I ever imagined. It was featured by Medium and it went on their homepage.

The founder of Airbnb sent it to the entire company because he was so proud of what I wrote about my experience there. And so it just showed me that, hey, maybe there's something here. Maybe I have wisdom to share about my experience. So I just kept doing that, and it kept going well. Then there's this point where I kept struggling, [thinking]…Maybe I should stop the writing and focus on [starting a company] because it's sucking up all my time.

And there was this point where I had a chat with a friend who pointed out to me, "Okay, you like this writing thing, people seem to really value it. It's rare to find something people value that you enjoy, so maybe you should just stick with that...and maybe put the startup stuff on pause." So that's what I did and I decided to commit to a newsletter that went out every week, and nine months later I decided to start charging for it because it kept growing and now we're here and it continues to grow.

I guess my lesson there is, if you find something that you enjoy and other people find valuable, just see how long you can continue down that road to see if it turns into something that you may not expect.

Tell us about the community around Lenny's Newsletter.

I'd say there's three core groups; product managers, growth leaders, PMs and engineers usually or marketing people, and then founders. Then there's also designers, and researchers, and people that work with these functions. I think I mentioned this earlier, there's this filter - who are the people that pay for content? And so that's the general vibe, people who are trying to get better at their job and build better stuff and grow their business, that kind of thing. So it's a really interesting collection of humans.

OK, so you're like, "I have something to learn and share and people have these questions and it's valuable, so I'm going to keep doing it." At that time, did you plan on co-building a community of readers?

I'd say the last thing I ever wanted was to build and run a community. I'm a big introvert and I don't want to be in front of large crowds. I like this intimate fireside chat feel, and so I had no desire to become the center of anything like that. And so the way it happened was, I was launching the paid newsletter and I was going to charge $15 a month for this newsletter, which is $15 bucks a month for four emails. Which is more than Netflix and more than most things people pay for every month and it just felt crazy.

So I thought about what else I could offer to hit this price point that I think is the right price point. So I said, "I'm going to launch a community and you're going to get access to a private community of only subscribers and it's going to be great." I pitched that as part of it. Then three months after I launched the paid plan, I realized I had to do this, and so I decided to sign up for Slack and create a little community and then invited ~30 people in there.

I wanted to make sure it was going to be great if I was going to do it, and so I spent a lot of thought and time about how to do it right, and to incubate it with the right kind of people, and to create the right rituals and things. But I really did not want to do this. I'd rather not have more work to do. That's a life goal right now, is do less work than more work, but I will say it's probably been the most fulfilling part of this whole journey - the community that has formed around this newsletter.

Let’s talk about establishing rituals that make the place feel different than other places.

The main thing I found to be really important is not even rituals, but more detail-orientedness around really small things that create a feeling like it's high signal to noise. So I made sure from the beginning that everyone had a profile photo. Everyone has a profile photo as soon as they sign up. If they don't, I just bug them really quickly like, "Hey, make sure that you upload a profile photo." It feels a lot more human if [they have a photo] and everyone ends up doing that.

I created one channel for self-promotion [to] just funnel it into one place and keep everything else really clean of self-promotion. That's helped a lot. I make sure people use threads and it's not just a bunch of messy, random conversations. If someone's asking questions in a really awkward way, I ping them and ask them to rephrase it.

So I just stay on top of it and I stayed on top of it for the first six months, checking it constantly to make sure everything looked really high quality. Now I actually have a community lead who helps me out because I don't have time to spend all that time in the community. So those little things, they really made a big difference. I’ll also add, there's a really powerful filter—you only get access [to the community] if you're a paid subscriber.

And I think that filter of people that pay for content is really interesting and leads to people that want to engage and have interesting things to contribute. So I think it's important to have some kind of culture that leads to the kind of place people really want to participate in.

It sounds like even though it's not something that you were drawn to do, you saw a reason to build community. What was the thing that you were like, "Okay, this could be useful and helpful and there is a value on it in terms of asking people to be paid subscribers”?

It actually came from [the idea that] there are so many smart people around this newsletter. I felt like if I connect them with each other, they'd find value helping each other. And, it’ll take me out of having to have all the answers to all of people's questions because again, I don't like being the center of attention. And so I'd rather be like, "Hey, go over here and other people can help you solve these problems because I'm not going to have all the answers."

Those are the reasons that I felt like this was going to be a good idea. I think that's a lesson also: If your product has collected a bunch of really smart, interesting people, there's probably an opportunity to bring them together and often good things happen. The other thing I found is I had a very clear group of people, which are product managers, growth leaders, and founders mostly. And so there's a clear idea of what they're going to talk about and what they've come to the community for.

I'll [also] add, I really like the idea of promoting other voices that have really great advice. I have this bonus newsletter that comes out of the best content in the community that now gets sent out to all the community members. And so I just like the idea of giving people a platform to surface their wisdom and maybe launch their own newsletters in the future.

Tell us about this bonus newsletter.

A lot of these things emerged from things people highlight within the community, things they wish they had. Somebody said, "I can't keep up with all this stuff, there's too much going on." Can you just have a summary of the week of the best stuff that happened in the community?” So I found a lady, Kiyani, to go through the Slack every week and she picks the best five threads and summarizes them into a new newsletter of its own. And then I send that out as a bonus newsletter to all the paid subscribers.

We call it Community Wisdom (see the very first issue from 2020!) and it basically has people’s questions and then all the answers cleaned up and summarized, and people’s favorite links that they've shared. That has solved so many problems. Also, it's just all this amazing knowledge people are sharing that I [don’t have] have that is getting shared with the community, and it just creates the self-perpetuating feedback loop of knowledge being shared.

Kiyani, shout out to you!

One of your newsletters really caught my eye because you talk about the most important bottom-up SaaS metrics to track. You break metrics into two main groups; pre-revenue and post revenue. And then you dive into different topics within them—things like retention and virality. Then you break that down into invite rate, invite conversion rate, and virality. I have this persistent belief that building and supporting a thriving community directly impacts virality. What do you think about the idea of community being able to influence virality and ROI within an organization?

It's a really interesting and nuanced question. I think about it a little differently. [So if the question is], “What is the value of having a community around your product?”

I think there's a lot of power in that group because they become evangelists of what you're doing and they want tell their friends about it and they get more and more excited and deeper into what you're building. And so it becomes just a group of people that want to tell everyone. Wherever they go work, they want to talk about it, they want to tweet about it, they want to write about it. I think that's virality between organizations even moreso than within an organization.

In general, I think community is an accelerant of virality [and] word-of-mouth. I think you're totally right.

When you're a part of a community, what do you look for?

I think it comes down to just, are you getting some kind of value out of it? Whether it's business value like answering questions I have…or, can I contribute something that feels fulfilling? Because that's a different kind of value. And then if it's a social community, it's probably a different kind of value. Does it make me feel good getting closer to these friends and these people? Is it helping me learn something new?

So I think it always comes down to, is there value that I'm getting out of this thing? Which then comes to, what value do I need? I'm in a bunch of Discords and Slacks [that I don’t go to] because I just don't have a need and/or they’re not delivering on that need. So I think it's really important to think about what value you are delivering to your members and how do you accelerate that and grow that even more?

Flash question. What's the book you're loving right now? Simply because I really admire this about you.

I'm trying to read and get through a book called The Anthropocene Reviewed, which I imagine you've heard of.

I haven't.

Oh, wow. You're going to love it. There's this guy, John Green. He’s got this awesome podcast and he basically ranks regular things in life on a five-star scale like ginkgo trees and plagues and things like that. And he writes beautifully and he has a podcast where he does the same thing and you will love it.

One final question before we get to talking about Uncommon Support. How do you think about responsibility to a community and accountability within a community?

I feel very responsible for this thing to continue to go well, partly because people keep telling me how valuable it is to them, and so I don't want to break it.

Then I'd say as a company, I think there's a barbell situation. You’re either better off not having a community or actually putting real resources into making sure it goes well. Because I think the worst thing you can do is bring a lot of your customers and users together and not stay on top of that because it can lead to a lot of bad things for your company.

So I think it's really important as a business to stay on top of your community. [At] Airbnb, actually, we initially thought it'd be better not to moderate the community and just let it be self-serve, and that was a bad idea. I find you have to be in there to make sure your conversations are healthy, people's issues and concerns are addressed, that kind of thing. Because there's a lot of power in collective action of your community that you've brought together.

The way I think about it, it's more [that you need to] make sure you're putting in the time to make sure it's going well.

We ask all of our experts to choose a nonprofit whose cause and mission you want to highlight and then we donate in your honor. Can you tell us about the organization you chose to dedicate your Uncommon Support to?

Something I do alongside the newsletter and communities is that I have a job board where people post roles in tech jobs, and I promote them in my letter and on Twitter and things like that. Something I realized I could do is funnel a piece of that revenue to nonprofits that train underrepresented young people on tech skills so that they can someday fill those roles. And it creates this really cool flywheel of companies paying to post roles, which funds people learning those skills and then taking those jobs over the long run.

Every month, I pick a different nonprofit to donate some of that revenue to, and this month I'm donating to an organization called /dev/color. They train young people in tech skills. I'm going to be donating to [them] this month, so let's donate [my Uncommon Support to that, too.]