Brian Donohue on Operating Instapaper Through an Acquisition

TL;DR

Instapaper started as a side project by Marco Arment in 2008, solving early mobile reading problems (slow networks, no mobile web, poor reading apps). The market became niche as mobile networks improved and competitors like Pocket emerged.

Key insights

• Instapaper’s core use case shifted from a broad appeal (solving slow networks and poor mobile reading) to a niche: voracious media consumers who need a staging area for articles from multiple sources,
• The paid app download was a major cap on growth; removing it and switching to a freemium subscription model increased downloads dramatically (over 1M in one week vs. previous two years) and led to a 1
• A failed LOI with a media company taught the importance of adding breakup fees to disincentivize pullouts, and the psychological impact of counting on a deal before it closes.