Ian Landsman of UserScape

Today, I’m talking with , the founder of UserScape. UserScape are the creators of HelpSpot, web based and most recently Thermostat, to help you retain your best customers and win back critics. Ian was also the co-host of the which is how I first came across his work years ago as I was getting into the software world.  He recently published an article titled, , that details his approach to getting Thermostat off the ground and that’s what he came on the show to talk about today. The bootstrapped world has already pushed back against the idea of “VC” levels of speed, but Ian talks about pushing it back even further. He first started working on Thermostat in early 2017 but didn’t want to pull team members off HelpSpot for too long or put in crazy hours himself, so he knew it would be a long process and he was OK with that. In our chat today, we dig into Ian’s “Windup” strategy, why it was the right fit for him and his team, who it wouldn’t be right for, and how he’s approaching the path going forward. We also get a little off track at the end when I find out about Ian’s passion for poker. With the stage I’m at now, still building my first company, I’m much closer to the “growth at all costs” stage than to Ian’s strategy and came into the conversation skeptical, to be honest. But talking with Ian really made me think about balance and that at the end of the day, it all comes down to what’s right for you. Ian has a ton of experience as an entrepreneur and hearing his sustainable approach to the journey is something all founders can learn from.