AMAs August 4, 2020

I started a paid newsletter and made $4860 in my first month. AMA!

Rosie Sherry @rosiesherry

I left my previous business behind knowing that I wanted to dive deep(er) into community building.

Somehow I ended up here at Indie Hackers managing the community. (Thank you @csallen)

I also started a newsletter, first on Mailchimp then I moved to Substack.

One month ago I decided to go for the paid newsletter thing.

I made $4860 in the last 30 days. 😱

Ask Me Anything!

  1. 9

    Hey Rosie 👋,

    First of all, thanks so much for your amazing contribution to this community. It’s one of the best ones I’ve found online and I’m (and everyone else too) is sure that you play a huge part in that.

    My question though, and sorry if it’s a bit rude, is how the heck do you leave a $1m+ arr company and go back to working for someone else. I may not have understood what your previous business was but as far as I read:

    1. You owned it
    2. It was doing $1m+ arr
    3. You’re now working for IH and don’t have some type of partnership

    If any of that is wrong than I guess that’s my question but if not I’d love to hear your motivation!

    1. 13

      Grass is always greener on the other side.

      I lost all interest in running a company that had outgrown who I wanted to be and had grown into something that I didn’t really want to manage.

      When you start indie hacking, generally people want to be free from the tyranny of an employee.

      Often as businesses grow people realise that it is not what they want (anymore) and just want to be free from the tyranny of an employer.

      I spent more than 2 years handing the business over. My husband and I remain majority owners. Still make money from it and now the destiny Of it is out of my hands. I promised myself that I could not go in to help or save it should it run into trouble.

      I thought I could never work for anyone else again, but love being here at Indie Hackers 😍

      I also missed indie hacking, so having a little side gig helps me scratch that itch.

      1. 4

        I personally loved being an employee more than being an owner. Focus on doing one job well, benefits, deal with zero drama unless you want to, the list goes on. Of course the type of person you're working for makes all the difference but as an owner I feel like you never really get a good nights rest since the job never ends. Plus managing people sucks.

        1. 8

          My life goal now is to avoid managing people.

          1. 1

            Amen to managing people...

        2. 1

          I'm very curious how one can get to zero drama at work. In ~20 years of working, I haven't seen zero drama.

          1. 1

            Seeing drama is one thing, getting involved is another. Personality type makes a difference.

  2. 3

    Congrats Rosie. Really awesome.

    My question is how will you keep growing it?

    1. 4

      Magic. 🤩

      Also, keep consistent with writing. Invite others to write. Expand the knowledge base. Do online meet-ups. And then hopefully an actually community, how meta.

      1. 1

        i gotya. How much of this will be for the paid subs?

        My thinking was you might need some free stuff to attract more paid ones.

        Also. I do think you could do great making a community from the paid ones. you've got OG skills!

        1. 1

          Where my thoughts are currently at: free stuff is overrated...and are a trap.

          1. 2

            I both agree and disagree!

            Would love to have a properly chat about this at some point.

            Three reasons @antdke why I think paid is underrated:

            • People value paid stuff much more
            • There's the “free trap”. People get so used to free. They take it for granted
            • Once someone loves your work / thoughts they will buy it. You don't need to send them 20 free articles to persuade them.

            Having said that there's more than one way to skin a cat. And free also is unquestionably the right modal for some. Look at Joe Rogan's podcast ...

            1. 1

              i agree with your 3 points

              & yeah, this deserves a proper conversation

          2. 1

            @rosiesherry i 100% agree with this

            but I'd love to hear why you think so

            1. 2

              Obviously there are cases (like here at IH) that staying free makes sense. I don't want to be quoted saying not to never do stuff for free. :)

              I also have started to feel somewhat icky with how there is such strong emphasis on developing a huge following. I don't think that is the future. Chasing the a perfect image, likes and retweets, over being human, giving value and developing real relationships.

              People are chasing the following, rather than the connections. For me, it is the connections that provide real value and insight.

              When it comes to indie hackers, I think it's entirely possible to build an income by giving very little away for free and also by having a relatively small audience. And partly I want to show people that it is possible. Most people deserve to make money from their business and most people don't have a huge following.

              Rosieland is an example of that. No one in the IH world really knew who I was 18 months ago. I've focused on being and doing good, in 'Rosieland' and just as being 'Rosie'. I participate in places for free, offer my advice do good work via IH (and all my previous experience).

              I do a free curated newsletter. But my writing is paid for. I doubted it, to begin with, almost falling into the trap of maybe I should 'just' write a few free articles. I felt a bit arrogant not doing any free articles.

              And of course, I could put a larger effort in free content and marketing, it would be lovely to get 100, 200, 500 paid subscribers within a short space of time. (Or would it? It could actually become quite painful and be a bad experience for me or my customers). But it's not the only way. It could take a year for me to get to that point and I feel I'd probably miss out on an opportunity with the fact that I believe people need what I will be sharing 'now'. Not next year.

              Some thoughts flying through my head:

              • validates my path almost immediately
              • I enter a contract with my readers/customers
              • this contract has forced me to deliver with writing like I've never done before (I've had it on my list for years to write consistently)
              • this contract gives me permission to create better relationships with my customers, I've had some great insights and connections already
              • I've written better and deeper than I normally would have, I want to keep my customers!
              • starting small allows me to think about how I really want this thing to grow

              I know that @harrydry does a great job at spreading his stuff. Putting effort into promoting it is a big part of that. I did that before for Ministry of Testing. I'm not excited about doing it again. Plus, I just don't have the time. Unless I quit IH, which I don't want to do.

              Rosieland is as much about making a sustainable income as it is about me becoming a better community builder, I feel I still have lots to learn.

              That turned into a bit of a long and messy response :)

              1. 1

                this was a well thought-out answer, i appreciate it

                from what I've seen, as soon as you have information that's valuable for a niche crowd, then going paid is a favorable route

                unless you're creating something that large swaths of people from different interest categories all find entertaining, then your "max audience" shrinks

                @harrydry that's where i think the Joe Rogan types fit in -- Their content is "widely palatable". I'd say that's where Marketing Examples fits in as well

                For me, I'll make The Product Person fit into that widely palatable category. Then make PM News much more narrow and niche.

                Also, my personal end goal is generational wealth. So I gotta get there somehow.

      2. 1

        A community of community builders =]

        Out of interest, do you plan on paying contributors? Or, rather, the value for them is the exposure to your audience?

        1. 3

          I would pay them, it would be wrong not to.

          1. 1

            thanks :) Look forward to seeing what lies ahead.

  3. 2

    Good on you! Wow :)

    I'm getting your free newsletter, so I've been seeing the subtle yet powerful pitch for the paid version. Genius.

    How long did it take to get to 550 free subs? Where did most of them come from?

    Also :D have you published about your process for putting together your curated links each week? I think remember you saying that you'd gotten it down to a manageable system...

    Thank you for this post!

    1. 2

      Getting to 550 subscribers took about 40 weeks, I count it by the number on my free weekly newsletter.

      I published my process for my curated links for my paid readers. The 'Study your people' post. 😉

  4. 2

    29 paid subscribers? How much does each of them pay?

      1. 1

        How that works? Even if all 29 paid $150, it would add up to $4,350 which is lower than your earnings?

        1. 1

          I'm guessing some paid for an annual subscription and she's counting those as well :P

          1. 4

            Just going with what Substack shows, lol. Maybe they calculate it assuming the monthly ones stay subscribers, not 100% sure how it works yet.

          2. 1

            That's what I said. Even if all paid for annual plans, it adds up to less what estimate is.

            1. 1

              Oh that's right my bad.

  5. 2

    Amazing! Initially the newsletter was free, right? How did you communicate to your subscribers that you were going paid?

    1. 1

      I started it by sending out a free weekly newsletter of curated community content. That remains free. I got to around 550 free subscribers with that.

      The paid part is extra posts (1 or 2 a week), access to a knowledge base that I’ve been building up for about a year and three the option to attend meet-ups (which I’m yet to organise).

      I told subscribers just by mentioning it in one of my free weekly newsletters. Then every week I say at the top of each newsletter what new posts there are.

      I don’t like to be pushy, I’m just going with the flow and ensuring I can sustain the habit of writing.

  6. 2

    Quite remarkable, congrats.

    How many susbcribers did you have when you started charging? Not sure I understand if you had 29.

    How many followers did you have on social platforms?

    1. 3

      I had about 550 free subscribers. Now it is 637 free subscribers then 29 paid ones (about half of them paid a year up front).

      The $4860 is not MRR

      I only use my personal Twitter, I tweet stuff about community, indie hacking and life, but not too much about my actual newsletter. I’m at about 9k followers.

      1. 1

        Thanks, now it's clear.

  7. 1

    phenomenal

    congrats Rosie! I started my own paid newsletter this Monday (https://pm.news)

    looking forward to getting to your level :)

    1. 2

      Ah, makes sense to see you on Lenny's Slack then :D

      I'm not sure how open you want to be, but I may start a monthly accountability thread in the Newsletter Crew group.

  8. 1

    of course... congrats! keep going!!

  9. 1

    Congrats Rosie! This is amazing and speaks volumes about how much your work is valued :)

  10. 1

    Um, this is amazing and you are my role model. That is all. :)

  11. 1

    Rosie! That’s amazing. Congratulations!!
    Keep the momentum going ☺️

    I’m starting a newsletter for my startup this month and I wanted to see if you have any tips for someone just starting off. Did you make any mistakes or run into any issues prior to getting to where you are now?

    I’m also using GetResponse right now for the newsletters but it’s a bit tedious having to constantly import new contacts from our website / app. Do you have any suggestions on what platforms to use and / or how to make this process easier?

    Thanks in advance for your reply! Really proud of your current pace! ☺️

    1. 2

      Honestly, my newsletter growth has been really slow. 650ish subscribers in a year is hardly massive. I've never really pushed it too much marketing wise, and I think that is key, to let it grow naturally and be ok with that. You end up only having people who are interested in what you are doing. I've hardly had anyone unsubscribe.

      The hardest part is showing up every week and to write something that is hopefully a bit better than the week before.

      I don't know about tools, I love Substack because it makes it so easy. I get to focus on writing and nothing else. EmailOctopus is worth a look. I think it is worth thinking about what you want to get out of it too.

      Isn't it all a matter of perspective. A newsletter is really just a blog that emails the content.

  12. 1

    What is the reason you decided to move from Mailchimp to Substack (never used it before)?

    1. 1

      The writing process. Substack focuses on making it so easy to write and publish. I didn't originally intend to do a paid newsletter, it just grew on me, and maybe I'm just a sucker to their marketing tactics!

      Mailchimp is a bit more old school and the process just didn't feel like fun.

  13. 1

    This is so cool, Rosie!

    Yourself/other Substack-ers have actually made me think about doing something similar (all-in-one newsletter, mentioning paid content) with my Ghost blog/newsletter.

    What a time we live in. I feel like newsletters have changed the blogging game.

  14. 1

    Made me audible say out "Wow!". Getting that kind of traction from 600 subs is amazing. Tells me that people can't get enough of your content ;)

    1. 1

      Quality over quantity. So many people say it, but don't really mean it.

  15. 1

    Congrats! Not sure if I have any questions right now as I've followed your journey since the day you launched ;) I guess one does come to mind - do you feel like you can sustain this indefinitely? (the writing).

    1. 1

      I think so, time will tell.

      But, longer term, I plan to work some people too, don't know who yet though!

  16. 1

    Hi Rosie! Thanks for doing this 😄

    I am using Substack for The BuildFaster Update.

    How did you take advantage of Substack’s unique features to improve conversion rates?

    Thanks 😊

    1. 2

      I think one of the biggest advantages of Substack is that it is essentially like a blog, it's much easier for people to share a link and to get an idea of what the content is about.

      Other newsletter providers aren't like this, mostly it's a mystery of what you are signing up to.

      As an example, with 650 subscribers, my last free newsletter got almost 1k views.

      TBH I never focus on conversions, I kind of shrug that stuff off and just try to focus on delivering value. The valuable content works, which is what converts people and what gets other people sharing it their networks.

      1. 1

        Thanks for the tips! I'll focus on the content too :)

        One more question if you don't mind. Have you used your Substack blog as a way to get backlinks for seo? Has it worked well?

        1. 1

          Honestly, I don't care about SEO. Sorry 😬

          Plus the main content is behind a paywall, so no chance of SEO value there. 🤷🏽‍♀️

          Of course it would be great to rank well. I've never checked.

          I went with Substack and a newsletter because I'm time poor. I can't manage much more than write. In time I'll likely be able to add more stuff in.

          1. 1

            Ok no worries. Thanks anyway for your answers :)

  17. 1

    Congrats Rosie, amazing!

    • How do you come up with ideas to write every week?

    I only use my personal Twitter, I tweet stuff about community, indie hacking and life, but not too much about my actual newsletter. I’m at about 9k followers.

    • Do you see Twitter as the main sales tool for creators and also for companies?
    1. 1

      I don't see anything I do as sales. I just exist within communities where we hopefully are curious and appreciate one another.

      I occasionally do a little bit of promo, but it's minimal.

      I tweet about community building stuff, that's my thing. Then people will naturally come across my newsletter as a result.

      Ideas are never ending, for me it's a case of taking down notes and then seeing which one I have the energy to write about.

  18. 1

    Great post!

    Point of clarification. The chart shows $4860 as total annualized revenue, which is multiplying the current base by the total number of months. So have you actually gotten $4860 so far or is this what the anticipated annual revenue would be if all your monthly subscribers stayed on? This would imply that the MRR is about $405/month (currently), which means you're getting about $13.90 per subscribe per month. Is that correct?

    Of the $4860 annualized expected revenue, how much have you collected yet so far?

    Great job getting things going!

    1. 1

      I've made the $4860 and it has been transferred to me.

      About half of them were annual subscribers, so yes, effectively it's approx $400 MRR.

      Subscriptions are currently $15 pm or $150pa, it has a discount until the end of this month.

  19. 1

    Which books would you recommend for those who want to build private, invite-only communities?

    1. 1

      I’d recommend my newsletter! Will be writing about paid communities in it soon.

      I’m not sure any books really go into to that.

  20. 1

    That's awesome! How did you seed the initial email list base? I'm at close to 100 for the email list in 1.5 months for https://thediscourse.substack.com

    The annual payment for Substack is great for creators. You get upfront revenue to give more time and effort to this exercise.

    1. 3

      I just hung out with my people.

      A little bit here on IH. A little bit on Twitter. I'm on a couple of 'community Slacks'. I've done a couple of talks. etc.

      1. 1

        That's cool. Thanks for sharing!

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