How I Grew my Newsletter to 2.9K Subscribers

No-fluff realizations on launching, writing and distributing your ideas.

Writing this newsletter has become a huge source of joy.

It started in November with an urge to write more and now feels like a product I’m building. I’ve met great people, fleshed out ideas that were sitting in my head and learned a lot of tactical lessons.

Today, I want to share all of the lessons I’ve learned from growing this newsletter. This will be very relevant to people who want to start newsletters, podcasts or YouTube channels. But it will also help people launching a business or a consumer-facing product.

Below, I’ve outlined 25 lessons that I’ve realized along the way. To make this useful, I’m only sharing lessons I’ve personally learned, not clichés I’ve read. I’ll cover:

1. Launching 🎬

2. Imposter Syndrome 😰

3. Distribution 📩

4. Writing ✍️

5. Engaging with Readers 💬

6. The Future 🔮

🎬 Launching

Starting is intimidating — I totally get that. But with a few months of perspective, I have a few tips to get off the ground:

1) Start with Substack: There are a ton of tools out there (ex. Mailchimp, ConvertKit, Ghost) but Substack is the best. The goal of your early tools is to make writing and collecting emails painless. You can always change later if you want more features.

2) Brand it: 20 minutes before sharing my first post, I decided to name the newsletter Product Life. I went to Canva to make a simple logo and banner image. I’m happy I did this — it made the newsletter feel more like a publication than my own diary. In hindsight, I would make sure the domain matches the brand you choose. Try not to make my mistake!

3) Choose topics you care about: Don’t write what you think you should write. Write about a topic you actually care about. Why? Because you have to keep writing about it. 

For me, I felt like I had to write about interviewing/resumes because that’s what people asked about the most. But I REALLY didn’t want to write about that every week. I’ve avoided those topics and waded into unfamiliar territory with product management lessons because it was the most interesting to me. This helped me write consistently every week.

4) Don’t be shy: Launch! Get your first subscribers by sharing with your friends and on social media. Having readers will make you more accountable for your writing practice. You’ll also get feedback and data (like shares, likes and views). Trust me, writing with no feedback is demoralizing. 

My launch post on LinkedIn (where I had the biggest audience at the time) helped me get my first 200 followers.

5) Publicly commit to shipping: Tell your readers when they can expect your next newsletter. This is an excellent way to force accountability.

😰 Imposter Syndrome

I struggled with this a lot. How could I teach if I wasn’t an expert? Also, there were already so many great newsletters by product experts, like Lenny’s Newsletter, Ask Gib and Deb Liu’s Newsletter. What unique value could I add?

Below I’ll share some realizations that made me a lot more confident in sharing.

6) The best teachers are often respected peers: Think back to the people you learned the most from. Yes, some are teachers. But chances are you learned a lot from peers you respect. These could be great friends, all-star coworkers or students a few years ahead of you.

This is because those peers are closer to your current situation than teachers. Their advice may be more directly applicable and relatable. This is where you can add value at any stage of life or career!

7) Personal works better: On this note, I learned that people don’t care about generic advice. They want to know how you did it! I struggle with putting myself into the story too much (I don’t want to be egotistical or narrow) but I try because people get the most value from that. 📜 PMs Create the Truth is a good example of this.

8) Teach people 2-3 years behind you: I’m forgetting where I heard this advice but it is spot on. Imagine someone in your shoes 2-3 years ago. There’s probably a lot you could teach them! Sharing how you learned these things is very helpful.

9) Be a student of the game: All this said, don’t feel limited by your current experiences. For example, you don’t need to know everything about mindfulness to write about mindfulness. In fact, you can research, interview or curate useful content to help yourself and others learn more. I tried this approach with 🧠 How Elon Thinks and people seemed to really like it!

10) Don’t take yourself too seriously: I’m not a pro, so I try not to position myself as a humourless, expert. Make typos and experiment with tone, topics and style. People won’t care about your mistakes so long as you’re still driving value.

📩 Distribution

Your newsletter won’t grow if you don’t distribute it well. I’ve seen friends start newsletters, be shy about sharing them and give up because they couldn’t get it off the ground. Don’t be this guy/girl.

For growth, distribution > writing. You need to make sure your content is being shown to the right people. Here’s how I do it:

11) The highest ROI system: The best system I’ve learned for content distribution is 1) publish your newsletter, 2) tailor the content of the newsletter to a post on each distribution channel, 3) share. I learned this from Harry Dry’s must-read article and it works every time.

Here’s what I mean:

Feel free to use my Twitter thread, LinkedIn Post and Facebook Group post as templates.

This system takes about 1.5 hours a week. But it’s the main way I grow, outside of shares from readers like you. 🥰

12) Tap into underused markets: Don’t feel tied to the platforms that others use. LinkedIn and Facebook Groups, for example, have been the best for me. Occasionally, I’ll get a spike on Twitter but it isn’t consistent. Other channels to explore are Quora, Reddit, HackerNews, Medium publications, Pinterest, Youtube, Instagram and SEO. Here are some stats from my last 90 days to see the relative size of each channel:

13) Distribute where your style does well: I’m not great at witty quips (😅) so Twitter doesn’t match my strength. I’m better at long-form pieces and actionable templates — which happen to do better on LinkedIn/Facebook. Lean into your style.

14) Hook readers: There’s two way that I’ve seen content perform well on social media. They either create intrigue with a teaser (example here) or give value upfront (example here). I’m a big fan of the latter, which usually requires you to share a template, a framework or something else that is immediately actionable.

✍️ Writing

Great writing is the backbone of a newsletter. Here’s some advice I wish I had on Day One:

15) It gets easier: my first pieces were taking me 8-10 hours to finish. Last week’s article took 3-4. You’ll get better and faster at publishing.

16) Timeboxing: You’ll spend as much time as you give yourself to write. If you commit to shipping after 3 hours, you’ll create a finished product in 3 hours. 

17) Systems: Find a rhythm that works for you. I write well in 1 hour, sessions before work on weekday mornings. I’m a big fan of my “creative hour” and it makes me more productive throughout the day.

The view changes but my creative hour is a consistent part of my schedule.

18) Good enough: I write weekly. Some people write bi-weekly, monthly or quarterly. Adjust the length and fidelity to your writing cadence. I don’t think I can write in-depth, researched masterpieces like Li Jin or Wait But Why so I don’t hold myself to that quality standard. But I am good at condensing medium-sized ideas into short posts — so I stick with that!

19) Editor in Chief: If possible, find someone to edit/critique your initial posts. My girlfriend is my Editor in Chief. In the early days, she would read every article, give comments and fix grammar. With time, you’ll start to internalize the same feedback you keep receiving. For me, this was to flesh out ideas more, not lean as much on images and condense wordy sentences. Make sure to give them lots of love.

20) Find peers: It’s awesome to learn from others who are publishing regularly. Share ideas, learn from their experiences and try to help each other out where possible! Specifically, I’ve learned a lot from Linda of Product Lessons, Janel of BrainPint and Arinze of Arinze’s Weekly.

21) Find role models: When I started, James Clear’s Atomic Habits was my writing North Star. I loved the clarity, the use of models and the emphasis on actionable takeaways. You can see my focus on all of these in my early pieces like

But as time evolved, I wanted to have more fun and be punchier. This is when I found Rework by Jason Fried and David Heinemeier Hansson. I fell in love with the writing style. I remember starting one article, 🔥 PMs Let Fires Burn, copying the structure of their post (i.e. start with a counterintuitive title, give the best part at the start, build on it subsequent paragraphs and then use a specific example to anchor the point). This was a great way to learn how to write better.

💬 Engaging with Readers 

One of the best parts of writing is engaging with readers. Folks will ask questions, challenge your argument or connect you with other great ideas. Here are things I’ve learned about reader interaction:

22) Respond: I’ve made it a principle to respond to every comment, reply or message that I get. This has helped me meet readers and build relationships. It’s also a great source of feedback.

23) Use your newsletter as an FAQ: My first few articles were largely questions I had been asked during coffee chats or cold emails. I wrote about them and can now share them when asked the same question. This gives people more fleshed-out responses and scales my ability to help.

24) Ask people what they like: Send a quick email/survey to some of your subscribers. Ask them what they like, what they don’t and for a testimonial of your newsletter. This survey gave me a really clear direction of what was working (real stories on how I build products) and what wasn’t (generic frameworks, shallow industry analysis).

An example of really helpful feedback I got from one of my surveys.

25) Welcome emails set the tone: When people subscribe, they get a welcome email. This is a great way to introduce yourself, encourage interactions and introduce them to your content. I modelled mine off a few others I really enjoy (mostly Packy from Not Boring).

🔮 The Future

I’m still a newsletter noob. But I’m excited to try new things that come up. I think the next creative frontiers are collaborations, products, courses and research. I would love to hear your feedback on these.

Collaborations: One piece of feedback I’ve received is that folks would love to hear from some other PMs I know/work with. I’m excited to start looping in some great product people I know! If you’re interested, let me know.

Products: I want to build more products. This is more of a passion project than a natural extension of my newsletter. If you’re curious about what I’m building, shoot me a response and I’ll share what I’m up to.

Courses: I made my first course a few years ago on Skillshare. It was a great experience and I got some positive reviews. I’m starting to see if there are any spaces that I can uniquely value to with a course. Stay tuned.

Research: I want to stay a student of the game rather than fool myself into thinking I’m a master. This involves humbly researching how others tackle tough challenges. My first foray was in 🧠 How Elon Thinks. I’d like to do more in this vein.

Summary

• Start now and commit to shipping regularly. Build the muscle and a system to create consistently.

• Remember that growth is driven more by distribution than content. Try the system I use to tailor content to your different distribution channels.

• Find peers, role models and possibly an Editor in Chief. These will make your process more social and enjoyable.

• You don’t need to be a master to share your learnings. Remember to maintain a student mindset to humbly tackle interesting topics.

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🖼 Internet Things I’m Enjoying

Black Skinhead by Kanye West by Dissect: Love him or hate him, Kanye makes fascinating songs. Loved this deep dive into a personal favourite.

Using NPS Surveys in Product Development by Gibson Biddle: A breakdown of how Net-Promoter-Scores (NPS) work and how Gib used it at Netflix and Chegg.

Down the crypto rabbit hole I go by Jay Singh: My good friend goes from 0-1 about all the interesting trends in crypto. A really accessible and great read.

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Thanks for reading! If you like what you read, subscribe for weekly insights on product management, careers and personal growth:

See you next week,

Will

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