Drip

Rob Walling and Derrick Reimer co-founded Drip in 2013 as a lightweight email marketing automation tool focused on behavioral triggers. Rob was already well known in the bootstrapped SaaS community from his book "Start Small, Stay Small" and his blog. Drip's differentiation was simplicity: visual automation workflows where you could say "if someone visits the pricing page 3 times but doesn't convert, send this email." It launched without VC and grew through the bootstrapped founder community that Rob had spent years cultivating. By 2015 Drip was generating $1.5M+ annually. In 2016, Leadpages acquired Drip for a reported $7M — at the time one of the most celebrated bootstrapped exits in the SaaS community. Post-acquisition, under Leadpages then Insight Partners, Drip pivoted to focus on e-commerce stores. The bootstrapped origin story and the clean $7M exit made Drip one of the most-studied cases of building to acquisition rather than building to scale. Rob went on to co-found TinySeed, the first accelerator for bootstrapped founders.