That's not how you do a backup plan. He could have added Pressmatic as a product under the Headway umbrella, much like iThemes did with Backup Buddy. Instead, he stopped paying employees, stopped providing support, continued selling Headway, and created a new, separate company.

I used Headway for a while back in 2012. I wasn't very impressed. I thought it was incredibly buggy. Their support system involved posting to the forums. There were no tickets or even a way of marking the forum thread as resolved. As a consumer, I wasn't thrilled with the support. Then again, if the product works the way it's supposed to and it includes well-written documentation, I shouldn't even need support.

The impression I got was that there were two types of users: people who paid for a licence in the early days when it was a lifetime licence, and people who got on board later on and paid for a yearly licence. The only revenue he had coming in was from new users or people renewing their yearly licence. It seemed to me that a lot of people in the forums had the lifetime licence.