Ian Landsman of UserScape


Today, I’m talking with Ian Landsman, the founder of UserScape. UserScape are the creators of HelpSpot, web based help desk software and most recently Thermostat, NPS survey software to help you retain your best customers and win back critics. 

Ian was also the co-host of the Bootstrapped podcast 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, The “Windup” Strategy, 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.

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Topics covered:

  1. Background leading up to today
    1. What exactly is HelpSpot and how did it come about?
    2. What does your business look like now?
    3. When did Thermostat come into the picture?
  2. Thermostat and the “Windup” Strategy
    1. What is the windup strategy?
    2. What are the benefits to it?
    3. When does it transition out of the “Windup” phase? 
  3. “Rapid Fire” questions
  4. Where can listeners go to learn more?

Resources mentioned:

Where to learn more:

To hear more from Ian, you can follow him on Twitter or check out IanLandsman.com which has an incredible depth of content.