Thanks for the input! I'll read through those articles shortly.
I've come to realise this stuff isn't easy, so I'm not expecting opportunities to fall into my lap. I'll try to identify some smaller markets. I just don't want to feed my natural inclination to analyse everything until I'm in a state of paralysis and never actually get anything done. Of course, I'd prefer that over wasting time attempting to take on something I simply don't have the resources to achieve right now. It seems like a difficult balance.
From the articles I shared, there was a suggestion of taking a large market and breaking it down into smaller markets by building niche products. One of the examples was MindBody, which is an appointment management (and general purpose management) service specifically for Yoga studios. The whole product and marketing is geared towards that customer, instead of attempting to tackle appointment management as a whole.
It's demoralising to see someone as smart and experienced as Mckenzie struggling with Appointment Reminder. I checked a couple of blog posts and he says he was surprised the amount of effort it took to get off the ground, but also that he was distracted/burned out through other commitments and was taking on consulting work and other side-projects, etc. That is definitely something I'm going to be very careful to avoid as most of the successes I've seen are from people who became laser focused on their product.
At the same time, Appointment Reminder attempts to be a general purpose solution for all your booking needs across any market that might need it. I'm not surprised he is finding it difficult to cut out a slice.
Jason's software, Snip Salon Software, is appointment booking software for salons. I remember hearing Amy Hoy (from UnicornFree) say how difficult it is to sell to brick-and-mortar businesses that don't really see the true benefit of software. She said how that creates an instant roadblock to sales and traction.
I don't have a product out there so I can only go off feedback I've heard from other successful bootstrappers, but I'd be interested to hear if anybody has an opinion on why it might have been difficult for those products to get off the ground.