I'm sure he's a bright and likable guy, and from his resume I figure he must be an inspiring leader. But for me, being a great technologist is all about things actually working, about users actually getting served. Sure, one should fail a lot in the lab, and sure, startups should be trying enough things that some just don't have product/market fit. But that's very different to me than promising the moon and delivering stuff that doesn't actually work.
There were always those legacy customers from years before who had there stuff running on some boxes in an old datacenter that only a few of the original staff knew about, and required continuous care and attention. Ihere's a business lesson to learn there - if you sell a "lifetime" subscription for a product that will become obsolete, you'll pay a lifetime PR cost in the future when you can't continue with that product.
Coming from a pretty long Linux background, Solaris took some getting used to, but once I figured it out, it really was a better, more solid, better engineered solution. But Linux has a huge community - the people that loved Solaris are the old Unix graybeards, and that community wasn't growing.
Before my time, there were some debacles, such as a storage platform product that ended up losing data, but by the time I was there, they had learned the lessons, and I'll still say their core stack is still superior to any Linux based stack used in the datacenter today. It's been 4 years since I worked there.
In their shoes I think the lesson I would learn is "don't go back on a deal". They could have returned the money, transitioned people to another product, shifted people to a different vendor, or offered people the option of any of the three. I don't think it was initially a PR problem; it was bad behavior, unilaterally breaking a promise, that got them in hot water.
The company has quite the history.
I have to disagree with your characterizations. The products changed much over the years, many things were tried, many failed. Most startups change their product significantly over time and it's hardly surprising that the business they are in now isn't one of the early iterations they tried and failed at.
I strongly believe that Jason is one of the best technologists on the planet. So there.