I run a company called SendOwl, which is probably the biggest competitor to Gumroad, and I must admit I'm sad to see this. We've been watching them over the years and have been impressed with some of the work they've delivered. I've also met a few of their employees and have liked their thinking around selling digital goods and where it's going. You could see they wanted to make a success of the company.
Their problems, in my opinion, have come from being VC backed. VCs ultimately want thier money back and with this comes massive, often unrealistic growth expectations. I've had a lot of offers of VC money for SendOwl over the years but I've never once considered taking it. I've bootstrapped SendOwl because I wanted complete control of the company, to direct where I thought it should go, to create the company where I wanted to work at (we work a sensible 9-5, I spend lunchtimes hitting the gym...), but most importantly to serve our customers and build something for the long term. This last part is something I've always seen as uncompatabile with the VC model.
The VC model is alluring though - VC money makes growing quickly easier, it makes getting PR easier and it makes bringing in lots of staff early on an easy decision. I'm not saying it's right or wrong per say, it's just not the path I wanted to go down. Bootstrapping isn't as sexy as VC money, but as long as we're growing, getting great customer feedback, and innovating with new features I know we're on the right path. Focus on those three things with Boostrapping and it's hard to go far wrong to be honest.
Interestingly we're getting more and more people asking about us as a company and whether we'll be around long term, so maybe the tide is starting to turn. Anyway I wish everyone leaving Gumroad all the best for the future. And any sellers out there who are interested in alternatives please check us out at: https://www.sendowl.com Happy to also answers questions in the thread below!
I am the founder of SendOwl and this is not a project by us. It's clearly ripped off our brand though. Will be getting in touch with them to discuss the matter immediately.