Business & Productivity Lessons from a SaaS Serial Entrepreneur

Nathan Kontny is the CEO of Highrise, the SaaS CRM app that was originally developed by the 37Signals team, the makers of Basecamp.

Nathan is the co-founder of two YC companies – Inkling and Cityposh. One of them is still in business. The other one failed and had to be shut down. We talk about the lessons he learned from both those experiences and what he'd do differently now.

Nathan is also the creator of the online writing app Draft. He built that product and business as a solo founder. And he used blogging as a way to build an audience and get customers. That's a lot to do for any founder. And we have a great discussion on how he managed to keep so many plates spinning and get things done without going crazy.

A few years ago, Nathan became the CEO of Highrise. We talk about how he met Jason Fried, the co-founder, and CEO of Basecamp and how that led to a job offer. And we discuss the big challenges he's facing in turning things around at Highrise.

Nathan is an experienced serial entrepreneur. He's very transparent and shares a ton of valuable insights and advice with me. And is a great guy who I've really enjoyed getting to know better. I think you'll enjoy this interview and get a ton of value from it.