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Interview with Lenny Rachitsky, Writer of Lenny’s Newsletter

11min read

This interview is with Lenny Rachitsky. Lenny currently writes Lenny’s Newsletter, the #1 business newsletter on Substack, with over 270,000 subscribers. He also hosts the #1 product/growth podcast, runs a community of 10k+ founders and product leaders, manages a job board for product roles, and is an active angel investor. Previously, Lenny was a Product Lead at Airbnb, an engineer, and a founder.

Key Highlights

  • On deciding to write a newsletter – “This unusual path emerged organically. After leaving Airbnb, I gave myself 6 months to tinker and explore. My philosophy was to do more of what gave me energy, and do less of what sapped me of energy. After every call, every project, every meeting, I paid attention to whether I was more energized or less energized.”
  • On choosing essay topics – “I keep a long list of topics I want to write about (have about 50 currently), and have a rough idea of what the next 2-3 posts will be. As each Tuesday approaches, I pick the topic I’m most excited to write about this week. I optimize for my own curiosity vs. what people want, because that always leads to the best stuff.”
  • How Lenny started angel investing – “About five years ago, I started investing in friends who were leaving Airbnb to start companies.  Then I extended that to other friends starting companies. Then, with the newsletter growing, I’ve been able to become helpful to more and more founders, and get access to better opportunities, so I’ve followed that pull.”

How would you describe what you do today? 

It’s funny you ask that because I’m still trying to figure out how to describe what I do. I technically write for a living (so weird!), but I still can’t bring myself to call myself a “writer.” I’m not like a real writer. So I generally tell people I write a newsletter, host a podcast, run a job board, and do a bunch of angel investing. I focus on what I’m doing, vs. what I am, if that makes any sense. It feels more natural to me that way for some reason. But it’s probably some kind of impostor syndrome.

After a career as a founder / PM, why did you decide to start a newsletter business? How did you know it was the right time to do this?

Never ever did I have imagined that I’d be doing what I do now. When I left Airbnb in 2019, Plan A was to start another company, Plan B was to try to do advising full-time, Plan C was to join a startup, Plan D was to join a big company as a PM again. Not even Plan Z was to write full-time. 

This path emerged organically while I was taking time off to explore and tinker. I gave myself 6 months, and in that time my philosophy was to do more of what gave me energy, and do less of what sapped me of energy. After every call, every project, every meeting, I paid attention to whether I was more energized or less energized. I eventually realized that I was not excited about building a company, or advising, or PM’ing at a company. But I kept finding myself pulled to writing things that people found useful.

To help with this exploration phase, I created a two-week sprint with myself where every two weeks I wrote out three work goals and three personal goals for the coming weeks, and emailed this to three friends. At the end of those two weeks I circled back to share how it went. 

Lenny’s template for his two-week sprints

It’s super simple but created much-needed structure during this time, and it also helped me recognize that in my goal setting I kept being pulled to writing. After a couple of conversations with two wise friends, who pointed this out to me, I decided to lean into the writing and pause the other stuff. And I’ve never looked back.

What’s ironic (if that’s the right word) is that with this path, which I called “Project: Avoid getting a real job,” I aimed for a chill work-life-balance kind of life, with good-enough-income-life, low stress, and not focusing on making the most money. And I ended up making the most I’ve ever made in my life.

Have you always been a writer? Where (if anywhere) did you learn to write?

Absolutely not. I learned as I went, I didn’t focus so much on the “writing,” as that would freak me out. Instead, I focused on having a density of high-quality, easy to understand, advice. I find people get in their own way and fill their writing with long intros, useless context, and uninteresting pontification. I try to avoid that. Get to the point, synthesize it clearly, and get out of your own way. The book that most helped me increase that density is “On Writing Well.” Basically, it just teaches you cut cut cut, and cut some more. Also, more recently, the excellently titled: Nobody Wants to Read Your Sh*t by Steven Pressfield.

What has been the most surprising thing about starting a paid newsletter? 

The most surprising things have been (1) that no one was doing this well already and how much open space there is (and still is), (2) how long I’ve been able to keep at it with no end in sight, (3) how deeply fulfilling it has been—I get at least one message a day from someone whose career has meaningfully benefited from something I’ve put out (4) and how lucrative it has been—you don’t expect writing on the internet to make money—I make more doing this than I made at Airbnb as a product lead, stock included. Can you ask for anything more? I don’t think so. I feel incredibly lucky.

Also, writing a paid newsletter is the ultimate meritocracy. If people find it useful, they subscribe and pay and tell their friends about it. As soon as it stops being useful, they unsubscribe. It’s pretty obvious if you’re providing value to people or not. 

If you could start again, what would you do differently? 

If I were to start again, I don’t actually think I’d do much differently. Maybe start charging sooner? Maybe call it something other than the default name Substack suggested when I signed up 😅

When you are looking to write a new essay, what is your process like? 

I keep a list of topics I want to write about (have about 50 currently), and have a rough idea of what the next 2-3 posts will be. I pick the topic I’m most excited to write about this week (as I optimize for my own curiosity vs. what people want because it ends up being better that way, and I stay sane). 

I always frame my posts as a question, since it’s an advice column, the post always starts with a concrete, simple, direct question from a reader. For example, what is a good retention rate, how did the biggest consumer apps get their first 1,000 users, or how do you build a consumer business.

Each topic has a Coda page where I start throwing bullet points of ideas, quotes, stats, anything I have off the top of my head.

For posts where I want to include quotes/stories from experts, I make a list of my wishlist of people I’d love to loop in, and then email them all individually. This usually requires 2-3 weeks lead time, so I think ahead on these.

For posts where I’m doing my own research, I throw all of my findings into the doc, in a messy way, and keep adding to it as I learn more.

Once I have some raw nuggets, I start to mold it into something that’s interesting. I stare at it and look for patterns, frameworks, and simple ways to share the conclusions. Then, I write a first draft of the post, and take a pass at charts, tables, and visuals.

I then read through it dozens of times, refining and editing each time, until it starts to feel solid. I email myself a copy to look at it with fresh eyes, and continue refining and editing. I have my copyeditor review it and fix all the issues. I may have my designer create a fun graphic for it. 

Once I read through it and I don’t see many things I can improve (probably on the 50th reading), it’s ready to go.

Finally, I ship it. 

It takes me a median of 10 hours per post. Sometimes just 3 hours, sometimes 100+ hours.

What essay has done the best for you? Can you generally predict which pieces will do better than others?

Here are the most popular posts of all-time, sorted by views. 

Generally, there’s a very strong correlation between the time I put into a post and how well it does (e.g. all the posts that took 100+ hours are in the top 10), BUT two of the top five posts of all time (Favorite Templates and Mission → Vision → Strategy → Goals → Roadmap → Task) took me less than five hours. 

Also, a good number of the top twenty are guest posts, which take me a lot less time (mostly editing and refining with the guest author), but are also some of the most popular. Which ends up being a win-win.

Have you ever thought about using a different email platform? If not, what do you like most about Substack / keeps you on there?

I  have indeed, especially as the revenue has grown and the $$ I send Substack is absurd for an email/blogging platform, BUT three things have kept me from going anywhere else (and I don’t expect I ever will):

  1. Through their discovery features (especially their recommendation feature), they now drive 12% of new paid subscribers, and 78% of my free subscribers. Their fee is 10%, so they now pay for themselves. Easy decision.
  2. I’ve seen folks leave Substack to avoid these fees and their growth slows. I’d rather optimize for long-term growth vs. eeking out every last %.
  3. I find that time spent on anything that isn’t making great content is wasted time, and time spent -> quality, so not having to worry about anything administrative is a huge advantage.

What niche (besides product / growth) do you think has an opportunity for a big business newsletter that no one is currently capitalizing on?

I tweeted about this a while back and there’s now two killer engineering newsletters (Gergely and Alex), so that one is covered I think, but I still think there’s a killer opportunity to be the Lenny’s Newsletter for (1) B2B sales, (2) negotiation, and (3) angel investing. Also, I have a random feeling there’s a big opportunity in the gardening space.

Broadly, I think there are four jobs to be done in the newsletter space:

  1. Entertain people
  2. Help people make money
  3. Help people be better at work or life <-My newsletter is in this bucket
  4. Inform people (e.g. news)

Pick a niche and pick a JTBD and there’s an opportunity there. With 1,000 paid subscribers at $10/month you’re making over $100k/year. How many niches have 1,000 people willing to pay something for great content?

Is there anything you wish you started doing with your finances earlier in your career? 

I actually feel good about my financial choices early on. Like the nerd I was, I read The Bogleheads' Guide to Investing when I was in high school, and that really influenced how I thought about investing. So I put most of my money in index funds from the start, plus bought a bunch of tech stocks that worked out great (up to recently at least). I feel pretty lucky about all of that tbh. If anything, I should have probably put more into index funds looking back 😬 . 

Are there any areas of your finances that you still find confusing? 

So many! It’s why I finally went with a professional financial advisor, since I just don't have time to think about how to best optimize my investing anymore.

Have you made any purchases since getting liquidity that have been really worth it? Any that haven’t lived up to hype?

When I think back, the best money I spent has been on trips. Those are the memories that seem to last. Plus, finding ways to be generous with my family and friends. 

Other than that, it feels like the only things that have made a real dent in my happiness have been a great laptop and phone.

How do you think about your overall investment strategy? 

There are three buckets for me:

  • Index funds
  • Individual stocks
  • Angel investing

Up until recently, I’ve been really proud of the individual stocks I’ve picked, but now that the market has come back to earth, I’m increasingly convinced index funds are the way to go. Too soon to tell if the angel investing will have been a worthwhile endeavor. I’m feeling optimistic though. 

When did you start angel investing? How did you think about how much to allocate to angel investing versus other investments? 

About five years ago, I started investing in friends who were leaving Airbnb to start companies.  Then I extended that to other friends starting companies. Then, after leaving Airbnb and with the newsletter growing, I’ve been able to become helpful to more and more founders, and see more interesting deals, so I’ve followed that pull.

I’m trying to put about 10% of net worth into angel investing. But it’s a very expensive hobby 😬.

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