[quote=“Damien, post:1, topic:4823”]
How the heck do you know what direction to go? I don’t want to hang around in this prolonged brainstorming session for too long
[/quote]Pick a product you want to build, create MVP (minimum viable product). Ship it, even if it doesn’t have all the features you like it to have and if it has known bugs, that’s OK. Advertise it, and see how users respond - let it run for some 2-3 months.
Don’t spend much time reading/watching various articles, books, podcasts, videos about “how to build business” - most of the advices there will not work for your product anyway 
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Always exceptions to any ‘rule’. If everyone keeps saying it maybe you’re the odd one out? Not a bad thing of course - just saying that I think its more common for programmers leaving the 9-5 (and it seems mostly to be programmers in this tribe) to find the programming bit easy and the rest much harder & time consuming than they ever imagined.
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I just want to pipe up here and validate that you’re right to feel this way. I also want to thank you: I’ve been bothered by the often caustic tone of this forum for a while, but I think witnessing this thread has finally pushed me over the edge to close my account. As a bootstrapper I’ve probably enjoyed more success than most of the other participants here, but all I can think when I read some of the comments that come in early on threads is that if I had gotten the same type of feedback several years ago, I would have been more demoralized than encouraged.
To your topic: I’ve been through the exact same transition that you’re eyeing yourself, including the Ruby and rails background. I can’t claim to have many answers other than what worked for me, but feel free to hit me up privately. I’m pretty easy to find online.
Cheers!
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Valid point, although I’m surprised that a niche has STAYED a niche for 20 years.
Also, I suspect that many businesses would sell more if they added some marketing.
For example if you are making $150K/ year and spending 1600h on programming and 400h on marketing and you doubled marketing to 800h and doubled revenue then that’s time well spent. (and you are at 33% spent on marketing).
Your situation may be very different.
However, most programmers I know don’t enjoy the marketing, so they don’t do it. That may not be financially lucrative, but that’s their choice and it’s fine.