I agree, the risk at the CTO/CIO level is it's four years later, the startup went under, and you have this software integrated into your environment. If you're lucky, someone else will have bought it. They'll on-ramp you to their stack. But then you run the risk of their seeing your as trapped. It's not about how much money you want to pay for the product. It's about extortion.

Or, if you're less lucky, you'll left with software you can't maintain. Even if there's a contract clause that says you get all the yummy, yummy source code. You may not even be able to open source it because you don't own the copyright to some or all of the code. You just have the source code. Good luck with that.

No one gets fired for buying IBM because you know (or at least we once knew) IBM would definitely be around for years to come to support the product. Is it expensive? Yes. Have I found a lot of enterprise products miserable to use? Yes. Does everything have the stink of "well we made it work well enough not to get fired?" Yes. But you won't be getting extorted Broadcom style, or sitting around with 5,000,000 lines of AI generated source that has all sorts of hacks and work around for the four other companies to whom the startup sold their software.