After almost 8 years in big tech engineering leadership1, I’m taking the leap to go full-time on Instapaper (again!)

I have a lot of mixed feelings about the change: nervousness, excitement, and a bit of the old FUD…


Since Instapaper spun out of Pinterest in 2018, it’s been a part-time endeavor. When we did the spinout Instapaper had server bills over $400k/year and no revenue.

Underlying the dubious economics was a hypothesis: we could reduce the server costs, and re-launch the Instapaper Premium subscription to make Instapaper profitable and sustainable.

We outlined that goal in a 2018 post titled The next ten years of Instapaper:

Our goal is to build a long-term sustainable product and business, without venture capital, and we need your help to achieve that goal.

4 months after relaunching Instapaper Premium, we achieved that goal by keeping operating overhead low and not paying ourselves salaries. We were ramen profitable. It was and has continued to be a labor of love.

Through ’18–’21 Instapaper subscription revenue grew slowly and compounded. In late ’22 and ’23 it became clear that it could actually support one person full-time at below market rates.

Last November I wrote about my 10 Years of Instapaper, and hinted about this:

It’s only been in the past year or two that Instapaper has generated enough revenue to support additional contractors and maybe now a full-time employee. I’ve been thinking a lot about this. Maybe after 10 years it’s time to pass the torch to another iOS engineer-would-be-CEO.

I haven’t made any decisions there, but increasing investment in Instapaper is top of mind and something we’re working toward for 2024. There is still so much untapped opportunity for Instapaper and, even after 10 years, there is still much work to do.

Price Change

In December we took the first step toward increasing investment in Instapaper without sacrificing sustainability, which was to launch Permanent Archive and increase the price of Instapaper Premium from $3/month to $6/month.

Despite this being our first price change since 2014 2, we still upset many customers, particularly around moving the price up 100%.

Honestly, I was between increasing the price from $3/month to either $5/month (+66% increase) or $6/month (+100% increase). At these low amounts per month, any price increase represents a fairly significant percent change.

With a lot of analysis, I determined that $6/month would help to ensure I could go full-time on Instapaper, significantly increase the investment, and not sacrifice our goals around sustainability.

At this point, I don’t anticipate further price increases for Instapaper Premium on a similar scale of time.3

Two months into the price change, retention has remained close to what we modeled (~80%) and, for the first time in many years, I can now work full-time on Instapaper and support my family.

Despite some of the negative reactions from customers, I also received positive ones that have stuck with me and boosted my motivation:

No questions or concerns, just wanted to say that I fully support this change and want you to remain in business until the end of linear time.

Remaining in business until the end of linear time. It’s ambitious, and it’s our new goal.

Looking Forward

More than ever, I’m excited to work full-time on Instapaper. A lot has changed over the past few years of my part-time stewardship, including our customers’ expectations.

I’m looking forward to meeting and exceeding our customers’ expectations, getting my hands back into software full-time, exploring how to improve Instapaper with machine learning4, and generally getting back to my roots.

In many ways it’s strange to have made this big journey from working on Instapaper, to leading engineering orgs at Pinterest and DoorDash, and back to working on Instapaper. The journey has taken me back to where I started, albeit with significantly more experience and perspective.

Psychologically I have battled with the question: is this taking a step backwards in my career? It’s almost felt like revisiting a relationship with an old significant other with whom you had lots of great memories, but also some challenges.

I’m fortunate to be surrounded by friends and family who have given me the confidence to put those concerns to the side and take another big leap with my dear, old friend Instapaper.

I’m also hoping to have a bit more time to write on this blog, and send out emails when new articles are published. If interested, you can subscribe by submitting your email below.

  1. Has it been that long already? 

  2. How many times has Netflix or Spotify increased their subscription price over the same time period?! 

  3. i.e. almost a decade 

  4. Machine learning, not “AI”.