I became involved in open source full time in 2001 when I joined the company behind OpenNMS, an open source network monitoring platform. In 2002 I became the primary maintainer when that company decided to stop supporting the project. Becoming the maintainer was easier than explaining to my wife that I was quitting my job to sell free software. I was able to grow the company up until 2019 when we sold it, and I stayed with the acquiring company until 2021. Our customers were some of the biggest companies in the world, and we explored every possible way to make money while keeping the product 100% free and open source software. In this session I will talk about how we got started, what worked and what didn't, and what I would do differently if I had to do it all again.