I write Lenny's Newsletter, the #1 paid business newsletter on Substack, generating over $500k ARR. AMA.

I currently spend most of my time writing a newsletter, angel investing, and generally trying to be helpful. Previously, I spent seven years at Airbnb leading initiatives in growth, quality, and community, and before Airbnb I had my own startup (which we sold to Airbnb). Prior to that I was an engineer for about ten years at a startup in San Diego. I was born in the USSR, grew up in LA, then went to San Diego for school, then Montreal for a bit, and now I'm live in the bay area.

Ask me anything about product, growth, angel investing, or writing online. I'll do my best to answer as succinctly, concretely, and candidly as possible.

  1. 5

    I love what you're doing Lenny and have known you from before this AmA. I run /r/SaaS, with 20k subscribers

    Wanna do something there? An AmA, a podcast episode?

    I recorded episodes with Justin Jackson, Hiten Shah, etc. Would love to have you come over and share your knowledge with the community

  2. 4

    I saw that you recently started a Pallet job board - how have you found that experience?

    1. 4

      It’s been most excellent. Once you aggregate an interesting audience, you can do all kinds of things to serve their other needs.

  3. 3

    Why stay on substack when you've reached such a huge size?

    1. 4

      It's obscene what I pay Substack at this point but what I find is that any time I spend NOT on writing great stuff (e.g. running ads, administering the site, fixing bugs) is not time well spent. Growth slows and quality suffers. And Substack lets me focus JUST on writing. They solve a ton of problems for me with zero work. My bet is that this will help me more long-term than saving money short-term. And I can always leave down the road and instantly make that %. My hope is in the future they tier their fees and so I pay less + they are now offering a ton of services, like health insurance, paying for a designer and copyeditor, premium Getty images, etc.

      1. 1

        Great answer to something I see asked a lot on twitter

      2. 1

        I'm no newsletter writer but I've heard really good things about ghost for publishing articles and newsletters(it's pricing model is really attractive!).
        I've been meaning to check it out myself but have yet to find the time to do it.


      3. 1

        I totally get that. I was curious because I just made a post about running a subscription newsletter using no-code tools for a tenth of the cost of substack.

        Probably a long shot but if you want me to set it up for you free of charge I'd be happy to. Cut that 50k+ you're paying yearly down to 5k :)

        Here's the post if you're interested: https://diynewsletter.com/

        1. 1

          Super appreciate that, but I'd probably switch to Ghost or if I'd switch off Substack.

  4. 2

    What top 1-2 resources would you point to for younger entrepreneurs that are wanting to get into angel investing in their 20-30s?

      1. 1

        This is super helpful. Thanks for sharing!

  5. 2

    How did you think/find/research topics?

    My personal issue is running out of ideas. Maybe I'm overthinking it idk?

    I'm curious about your process on the above question.

    1. 1

      I set my newsletter up as an advice column, and so people send me questions. I have endless topics this way.

  6. 2

    One of your slides says "Get Twitter "influencers" excited" -- did that happen just by Tweeting, or did you develop a relationship first and then they noticed? And if so, how did you do so?

    1. 3

      99% they found the content valuable and had tweeted it organically in the past, and 1% I poked them when I was launching something to encourage them to share my launch

  7. 2

    These answers are great. I tweeted out to you an hour ago re: this AMA.

    I looked at your slides (thanks, it's awesome): and it includes screenshots of your Medium work. Was that foundational to kickstarting your growth, or could you have gone straight to Substack + Twitter to get to where you are without going to Medium, first?

    I do see one slide saying Lesson: Write guests post where your target audience is -- and so want to get a sense of how much start there before you newsletter.

    1. 2

      I could definitely have gone straight to Substack. I only started on Medium because I had no intention of doing this ongoing.

      Substack is better than Medium in basically every way (it just doesn’t look as nice)

  8. 2

    1.Did you settle on this simple name in one go? or was it a trial and error to which finally you settled on this?

    2.Also if your newsletter was pseudonymous and you hadn't revealed your experiences at Airbnb or leveraged that network. Would be possible to grow purely based on content?

    Thank you for your time! (sorry if the #2 sounds rude, I'm trying to understand what weighs more content or credibility)

    1. 3

      For the name, I went with the default name Substack suggested (lol) because I didn’t think I’d be doing this long-term.

      For (2), I definitely think the content would speak for itself. But I may be wrong.

  9. 2

    Given word of mouth / direct is highest, has sharing articles in communities like PMHQ been included in direct or didn’t result in much traffic?

    Related: after you hit “publish” what are the top three things you do afterwards that drives the growth loops for your newsletter?

    1. 2

      All of that to me counts as word of mouth since I don’t ask them to include the links, they just do because I imagine they’ll be useful to their audience.

      After publishing, I tweet a quick summary and post the link to LinkedIn.

  10. 2

    If you had to start all over again, what would you do differently?

    1. 2

      I'd maybe launch the paid plan earlier. I did the free newsletter for 9 months.

      1. 1

        Sweet thanks! Imma subscribe!

  11. 2

    What is your writing/editing schedule look like, do you have a set time or do you wait for the inspiration to hit ? Also, do you worry about updating your old published posts ?

    1. 3

      I don't schedule any meetings until 3pm or later, and use that time to write, research, edit. Since I know I have to deliver something great each Tuesday (that people are paying for), there's always motivation to hit those deadlines.

  12. 2

    What is your general research process for the newsletter and how many ideas are you working on at a time to keep up with all the content needs?

    1. 3

      I have a list of about 30 topics I want to write about in the future that I add to as new questions from readers come in, and I sort them based on what I'm most excited to write about next. For a post where I need to get quotes from founders (like this one: https://www.lennysnewsletter.com/p/how-the-biggest-consumer-apps-got), I first start with a wishlist of companies/people I'd love to hear from. Them I find a way to get to the founder or an early employee, through LinkedIn connections, or just cold email/DM. As I collect stories I dump them into a big Coda doc. Once I have enough, I go through them all and look for patterns and buckets that they'd fit into. Then I start to craft this into a story and/or framework.

      1. 1

        Was always curious about to hear about what this looked like behind the scenes. Will be interesting to draft an outline of how you grew this and continue to grow (maybe I'll do this aha).

        Free Newsletter -> Paid Newsletter + Enhance value via:

        • Slack Group
        • Email Summaries of Slack Group discussions and learnings
        • Aggregating Audience insights into Digestable Content via Surveys/Twitters
        • Perks and Discounts
        • Job Board
        • Featured Speakers
  13. 2

    That's amazing Lenny. Do you have any advice on where/how to find sponsors for newsletters?

    1. 3

      Build an audience that sponsors want, and then they'll come to you.

  14. 2

    How did you realize there was an audience for this and how did you grow it so quickly? What have been your best channels?

    1. 4

      It honestly blows my mind how large this has gotten (that ARR number in the post is the last public number I've shared, it's actually much larger now). I never had a master plan to make this how I make a living, it slowly emerged from my first Medium post doing really well, then more posts doing well, and I just kept pulling on the thread to see where it would take me.

      Growth is purely from word-of-mouth and Twitter. Initially, it was from guest posts, Twitter, and Medium. Check out this deck: https://www.canva.com/design/DAEctjxzvYQ/OUVN-gLFNOrxVV_Gc13E3A/view?utm_content=DAEctjxzvYQ&utm_campaign=designshare&utm_medium=link&utm_source=sharebutton

      1. 2

        Yeah I was just going to say - your newsletter has quite the flywheel going. In the PM community we're a pretty content enthusiastic bunch and people are constantly sharing findings, favorite blogs, news, etc.

        Your newsletter always comes up very early in those conversations haha

        1. 2

          I bet this applies to a lot more roles/functions than you'd think.

          1. 1

            I have been wondering about this. PM is changing so much and there are so many leading edges....I think we have to follow your writing to keep up. I am not in business operations, for example, but am in the community....I don’t see as many bleeding edges there.

            But curious how you would approach it.

      2. 1

        Did you feel it was a crowded space with other people writing about product, including VC and found a unique voice that would stand out? Or did you just write what you wanted to read (I think you said something like that in an interview) and that met a need? Or was there some other way you realized you hit a nerve?

        1. 6

          I felt like it was very crowded and I was too late to the game, but it turns out most content out in the world is not that good. Mostly because people don't have time to write, research, think. If you can carve that time out, you can create valuable content.

  15. 1

    Do you pay for any newsletters?

    What topics or audiences do you think are ripe for a successful paid newsletter?

  16. 1

    Your newsletter might be good then!

  17. 1

    Was there a recording where you presented yourself slides? One or two of them for me needed a little bit of coloring.

  18. 1

    Seems like guest posting helped quite a bit based on your slide (since it was a bullet). If you had to pick the most import pubs or outlets that got you up and running, which would they have been? I saw you had a screenshot of one publication (maybe First Round?)

    1. 1

      Andrew Chen's blog, and then First Round

  19. 1

    Do you use affiliates to grow further or incentivize promotion?

  20. 1

    What are your hours devoted to all things related to the newsletter (research, writing, promotion) per week?

    1. 4

      I'd estimate about 10 hours per week per post, all-in.

      1. 1

        Did the average hours per week change from when you started? If so, roughly what were they at the subscriber count milestones you listed in your deck?

        1. 1

          Has stayed relatively constant tbh, mostly because I'm actively not letting it suck up all of my time

          1. 1

            Wow! I don’t think I could get the research done I alone in less than 10 hours.

            How do you divide up roughly those 10 hours? I need to figure out where to cut down on my own writing I am taking way too long.

            1. 1

              Each post is so different, so it varies between maybe 5 hours of research and 1 hour of research.

  21. 1

    Im a developer working on my own sideproject.

    Do you think I need a co founder to make my project grow or is their books I can just use in preperation for my launch and worry about getting people for growth after I get some investment?

    1. 1

      Those are two very different questions. You definitely don’t need a co-founder but it generally increases the chances of success if you have one.

      You should be thinking about growth (how you will grow) from day one.

      1. 1

        I see! I guess what I mean is I already have some plans for growth and marketing, I have the tech skills to build what I need so my plan was to learn marketing to get me as far as I can and then once have the money hire someone for marketing.

        Thanks for the reply!

  22. 1

    The work you do in this field and the articles are top-notch! Being in product and preparing individuals for PM interviews through www.jinaldalal.com has helped me see that the information out there is limited. Is there a book in your horizon :-) ?

    1. 1

      I think eventually, yes. But not anytime soon. It’s so much freggin work!

  23. 1

    What does your writing 'process' look like? :)

    And also, what does 'marketing' look like for you these days? (I know you mentioned you were initially doing twitter/guest posts in one of your other answers)

    1. 3

      Idea -> Bullet points -> Research -> Draft -> Edit, edit, edit

  24. 1

    Love the work that you do! What's your tip for marketing a niche product? Where do you start? In context, I have a Gmail plug in that filters out non-essential emails (using auto filters, domain blocking, specific user/email blocking).

    1. 3
      1. Figure out who very specifically needs this most
      2. Figure out how to succinctly pitch it such that they feel "OMG I NEED THIS"
      3. Figure out where they spend time online and offline
      4. Go there and pitch them your pitch
  25. 1

    what would you do if you were 17 now? what skills would you learn and what would you focus on?

    or what would you advice a 17 years old to do?

    1. 1

      Definitely get into tech, and ideally learn to code

  26. 1

    WoW! This is really a great achievement. Congrats Lenny.

    What is the exact process you follow to FIND and EVALUATE an idea for a profitable newsletter generating $100K+ ARR?

    A long & detailed reply would be more than welcome. Thanks in advance.

    PS - Any thoughts around creating a business around "Content Curation especially for Entrepreneurs/Sales/Marketing/Branding/Content Marketing & Social Media Marketing professionals?

    1. 2

      I wish I had a process to share, but what I did was think about:

      1. What do I WANT to write about for a while. What would keep me interested and curious to explore?
      2. What isn't already done SUPER well, where I have a chance to add something new to the conversation.

      That's it!

  27. 1

    If you were to describe an approach or framework to find untapped white space in the tech/product newsletter space, how would you go about doing so?

    1. 2

      My advice is to do the opposite—think about what you be excited to write about for months, that you don't think has been covered really well, and do that. I find that if you are curious about something and not finding answers to that which satisfy you, there are hundreds/thousands of other people with the same need.

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