I think it's a generally frugal market even if some of us are flush with a bit of cash. There's a lot you can get done for free with various FOSS stacks, and outside of highly specialized tools that aren't easy to replicate in features/availability/guarantees, I think it's a hard market to get a foot in, because the power of NIH is so strong. Things like IDEs, or security services, that take either a very slow burn or a lot of programming/design power are possibly the exception, and even then you can spoil it. A lot of people on here got upset when JetBrains moved from permanent licenses to a subscription service -- but in hindsight, I think it was the right move and it probably paid off! Think about that: you have a tool that is used in-and-out, like bread and butter, every day, like 30 hours a week -- and
maybe,
if you're lucky, a developer who makes 6 figures will say "ok I'll pay $200 a year i guess" or whatever. It's kind of incredible! Of course corporate accounts do not bat an eye at this; in fact they like continuous support, renewals, and services. It keeps things regular.
It's very easy to look at JetBrains and say it can obviously work, just the same way people look at RedHat (or other outliers) and say it can work. They're a standout company in this space, and have high reputation, and it didn't come from nowhere. They almost make it look easy -- just sell a great product, boom! But it depends on a lot of factors like when they entered the market, how they grew over time, etc. It's possible they wouldn't be able to get off the ground today if they tried this whole thing again.
In fact I wouldn't be surprised if JetBrains existence, happening before the whole VC craze, has in fact influenced the market itself, today: even with millions of dollars of VC funny money, it would probably be very difficult to compete with them on their turf in 2019, when they have extremely high reputation and a big array of products, in a market that is a very "small world". They're the 900lb gorilla in the room, in a sense, but they did it on their own.
JetBrains products are amazing though, without a doubt, and they deserve their success. I wish them all the best.