Nowadays we hear about “the consumerization of IT” and removing friction from user funnels everywhere. This episode covers how sometimes that can be the wrong move for the business even if users and the market think a freemium go to market is the best approach.

Bobby Pinero is Co-Founder & CEO of Equals, a next-gen spreadsheet. He was previously the first finance hire at Intercom and employee 20. In this episode, we cover why Freemium didn’t work for Equals and how Free Trial is actually a better fit. Bobby describes tips for building a horizontal product, how he approaches founder driven marketing, lessons from Intercom and how even seemingly small internal communication emails can have a massive impact on the business. This episode debunks a lot of popular blog posts out there now and instead focuses on first principles thinking to arrive at what makes sense for each business and product.