Ten years ago, in the summer of 2013, my startup failed. We had run out of money, everyone was laid off, and I ran down my personal savings trying to make it work. I needed a job as soon as possible, and there was only one place I wanted to work: betaworks.

At the time, betaworks was a startup studio in NYC known for building (bitly/Chartbeat), investing in (Tumblr/Kickstarter), and acquiring companies (Digg/Instapaper). There were a few open opportunities for my skill set (full stack iOS development), and I quickly chose Instapaper because…

  • I love reading.
  • It was primarily an iOS app, and I was interviewing as an iOS engineer.
  • It was an opportunity to work at a much larger scale than my previous startup efforts.

After passing the interview, I received the job offer. That was 10 years ago. I couldn’t have imagined the journey working on Instapaper, building an amazing product with incredible people. This work has been the source of my most fulfilling and greatest career achievements, and wanted to do a brief look back at the phases of my involvement in Instapaper over the past 10 years.

2013–2016: betaworks era

Instapaper was acquired by betaworks in spring 2013, and I joined the betaworks-Instapaper founding team in June 2013. I was hired as an iOS engineer, but I had developed a broader, founder skill set at my failed startup. As gaps in responsibilities emerged, I instinctively went to pick them up. Blog post? I’ll write it. Financial model? I’ll create it. Competitive landscape? I’ll do it.

Within 18 months I moved from iOS engineer to CEO. The big bet where I earned the CEO role was moving Instapaper to a freemium subscription business. Instapaper was previously a $3.99 app download with an optional $1/month subscription. I advocated for it to be free to download with a $3/month subscription.

That was an obvious decision in hindsight. The world’s biggest software companies have since moved to subscription business models (Microsoft, Adobe, Apple, etc). In 2013, that was not a foregone conclusion and the decision meant forgoing ~50% of the company’s revenue. You’d be prudent to be skeptical of some 24 year old kid telling you to dump half your company’s revenue and bet it all on some untested business model, and the betaworks team was prudent.

That said, I had the benefit of 5 years of Instapaper data and it clearly pointed to freemium as the logical evolution of the business.

After executing the freemium shift, the company’s revenue followed a J-curve and began to grow, we were on a path toward profitability, and I was put into the CEO role.

In 2015 we started exploring potential buyers for Instapaper. While the business was growing, it was slower than expected, and it became clear to us that the read-it-later market had become saturated and stopped growing.

It’s not a coincidence that Pocket/Instapaper acquisitions and Readability shutdown all occurred in 2016.

2016–2018: Pinterest acquisition

Pinterest was not in the initial set of conversations in 2015, and had come somewhere out of left field during the process. They had acquired some companies betaworks invested in, and expressed an interest in news. 9 months later they bought Instapaper (August 2016).

In late 2016, I put together a 2017 plan for Instapaper which included a few options:

  • Resource a full team around the product.
  • Staff some data engineers to explore news for Pinterest.
  • Put the product in maintenance mode.

After presenting to Pinterest’s founders, they asked for my recommendation. I knew that Pinterest was growing quickly and, from a business perspective, it did not make sense to divert resources from Pinterest to invest in Instapaper (which was not growing quickly). I recommended we put the product in maintenance mode.

Shortly afterwards, the deal sponsor for the Instapaper acquisition left Pinterest. I continued to work on Instapaper for 2 hours every Friday, nights, and weekends. Other than that I was full-time on Pinterest projects starting with Instapaper integrations, then ultimately moving on to other projects.

Through 2017 and 2018 I saw the writing on the wall. Instapaper was heading for a shutdown. No one explicitly said that to me, but I could connect the dots on the trajectory of its future. It’s something that weighed on me, and eventually I reached out to the CEO to discuss changing Instapaper’s trajectory.

Many conversations later, I exhausted the miniscule political capital I did have, and Pinterest agreed to spin Instapaper into an independent company.

I really have to give the credit for this decision to Ben Silbermann, Pinterest’s founder and then-CEO. Many CEOs pay lip service toward putting users first, but Ben actually makes decisions that put users first. That was the only reason to spin Instapaper out. He earned my deep admiration and respect for caring about Instapaper users as deeply as Pinterest users.

2018–Present: Independent Company

After completing the spin out in 2018, we published The Next 10 Years of Instapaper which was both a nod to the company being 10 years old, and a manifesto for how the new company would operate (long-term, sustainable, no venture capital).

We inherited Instapaper with no revenue (Pinterest had eliminated Instapaper revenue in 2016) and fairly large server costs ($35k/month). We raised a small friends & family round to cover operating expenses, relaunched Premium, streamlined the server costs, and were profitable within 4 months.

As part of the spinout, there was a handshake agreement that I would not be leaving Pinterest. I continued to lead larger teams there, ultimately leading all of the Product Engineering teams on the Core side of the company. I left Pinterest in ‘21 to join DoorDash as a Director of Engineering where I continue to work full-time.

And I continue to work on Instapaper nights and weekends (but not 2 hours every Friday anymore).

I took a look back at Instapaper’s blog, and I’m proud of everything we accomplished over the past 5 years especially given the level of investment we’ve been able to make in that time period.

That said, people’s expectations are always rising. I’ve heard a lot of feedback that people want Instapaper to do a lot more for them, and they want to see larger investment into Instapaper. We’ve brought on some contractors this year and started to address that feedback, and we’ve delivered three meaningful updates so far this year.

Over the past 5 years, Instapaper’s revenue has continued to grow. 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.