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Reflections on freemium

June 5, 2022newsletter

Hi there!

I’m trying something new. I’d like to be in touch with people (that’s you!) on a more regular basis.

So, welcome to my newsletter. My goal is to do this weekly, though I’m not going to hold myself perfectly to that standard.

To start with, my plan is to share the most interesting links I saved this week, a few powerful highlights from books I’m currently reading, and write a few reflections on one topic that’s been on my mind.

I hope you enjoy it! Hit reply to share any thoughts. And if this isn’t for you, unsubscribe anytime with the link at the bottom of the email.


🌍 Links I saved this week

Square Defangs Difficult Decisions with this System — Here’s How → This article is full of insights on improving decision making within organizations, particularly for difficult decisions. I’ve recently been calibrating which decisions I delegate and which I take on in the company, and this guidance really resonated.

Leave Me Alone Open Startup Page → Check out Leave Me Alone’s open page where they share their revenue, customer numbers, expenses, profitability, and much more. I love seeing this kind of transparency from companies, especially early on.

Subvert shitty norms → This article got me thinking about the supposed best practices that we sometimes don’t take a moment to reflect on, and feel comfortable about before implementing. It’s a great call for higher standards.

20 years of Atlassian, 20 lessons learned → It’s hard to believe Atlassian started over 20 years ago. This is a fun post with some great nuggets of wisdom they’ve learned over the years. Great advice on making freemium work, sustaining innovation, and investing in culture.

Structural transparency vs content-level transparency → As a proponent of transparency, I enjoyed the differentiation between structural and content-level transparency. The latter being the act of sharing raw insight into work as it’s happening. I agree that this can garner far more trust.

📚 What I highlighted this week

You are not your idea, and if you identify too closely with your ideas, you will take offense when they are challenged. To set up a healthy feedback system, you must remove power dynamics from the equation—you must enable yourself, in other words, to focus on the problem, not the person.

*From *Creativity, Inc. by Ed Catmull

I learned to go slowly when faced with the choice between two things that you need that are seemingly at odds. That way you can figure out how to have as much of both as possible. There is almost always a good path that you just haven’t discovered yet, so look for it until you find it rather than settle for the choice that is then apparent to you.

From Principles by Ray Dalio

🧠 Something that’s been on my mind

I’ve recently been thinking a lot about freemium. It’s always been core to our strategy at Buffer, and we’ve recently been doubling down on it and challenging ourselves to think how we can embrace freemium even more.

Two thoughts in particular on freemium:

  • If you don’t get your free limits right in freemium, it just doesn’t work. However, most think about this purely in terms of being too generous, and harming the free to paid conversion rate. I think the opposite is also a big risk: limiting the free plan too much, that you don’t provide enough value to drive genuine consistent free plan usage.
  • Any company that has success with freemium will always be at risk of the temptation to restrict the free plan more, or even drop freemium completely. The short-term A/B test will always favor dropping freemium, as if you test free plan vs free trial, the free trial variant will always likely win within any timeframe you could do an A/B test. The short-term revenue bump is hard to resist. The longer-term consequences are often not thought about enough.

🙋🏻‍♂️ A general update from me

Tomorrow I’m heading to LA for a Buffer exec team on-site. It’ll be our first one in over 2 years, and it’s been a long time coming. We’re at an exciting yet also challenging time as a company, and being able to align and go deeper on outlook for the rest of the year and strategic focuses, not to mention just having quality time together, is going to be awesome.

On the personal side, this week I completed my third week of my strength exercise routine. I’m working out three days a week (back, chest, legs), and it’s felt really good to get back into my flow after a couple of slower months.

Until next time,


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From time to time, I send out a newsletter with:

  • 🌍 Links I've recently saved
  • 📚 What I highlighted in books
  • 👨🏻‍💻 New and noteworthy at Buffer
  • 🧠 Something that's been on my mind
  • 🙋🏻‍♂️ A general update from me

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