Bits and pieces of my story are spread across my HN comment history, which goes back pretty close to the beginning of HN. I should write a script one day to download them all and concatenate them into one big file and then explore turning it into a book - or at least one or more in-depth blog posts.

Anyway... pain points. If I had to single out three things, it would be:

1. Lack of resources (money, time, etc.)

2. Lack of focus (trying to do too much)

3. Health issues

I could expand on each of those very much if I had time, but for now I'll try to be concise.

1 - at the very beginning, I think I thought that "the path" was to build a demo, maybe get some paying customers up front, and then go pursue a round of VC money, and do that traditional route. I even spent a bit of time getting to know the local VC's, talking to some of them (short of a formal "pitch" meeting, but talking about our stuff in broad brush strokes), going to VC related conferences and events, etc. But also early on I became very skittish about the idea of taking outside money, and especially doing so too early. So eventually I backed completely off of that and decided to focus on bootstrapping at least up to a point. The idea being that if we had demonstrable traction then we could decide if we needed to raise outside money or not, and IF we did, then we'd get better terms.

Now I don't necessarily regret that decision, but I will say this... I was never in the position of having so much money that I could just quit my day job and work on the startup full-time. And trying to do everything as a side project, "nights and weekends" is frankly a heck of a challenge. Is it doable? I still maintain that the answer is absolutely yes. But it constrains you, and you have to get a lot of things right to make it work. In that regard, we're still in the "waiting to see what happens" mode.

Anyway, a big part of why I would say we have yet to "turn the corner" ultimately comes down to:

2 - not being hyper-focused enough. In fact, just the opposite, trying to "boil the ocean" at times. It's a personality flaw of mine, it really is. I care too much about "big vision" stuff, and complicated webs of interdependencies, and trying to see how many many disparate pieces form some kind of whole. And that leads me to want to build very large, complicated, systems with lots of inter-related pieces that federate, integrate, etc. And see above about "resource constraints". When you're a one or two person shop, working "nights and weekends" there are simply physical limits to how big and complex a "thing" you can build in a given period of time - and that's assuming the "thing" you want to build is a good idea anyway.

TBH, I read @sgblank's The Four Steps to the Epiphany and the other "Lean Startup" literature, and I get it. I get it, and I fully endorse it. 100%. On a mental / logical level. Did I live it though? No, not really. I mean, yeah, up to a point in time. Up through the end of 2014 or so, we were fairly focused on a product that was based on using a combination of social networking styled tools, and semantic web technologies + search to build a platform for enterprise search / knowledge management. And we were making progress. We did all the Customer Discovery stuff, met with prospective customers, and found that yes there was some demand for what we were doing. And we had a product that was demo-able and borderline sale-able. This was as close as we've been (yet) to "turning the corner".

But ultimately progress wasn't as fast as it could/should have been, because of my inability to (or refusal to) really really narrow the vision, get hyper-laser-focused, and truly live the "go super narrow, get a beach-head, grow out from there" approach. I knew it was the right thing to do, but couldn't make myself do it.

Anyway, all of that takes us up to 2014 and leads us to point (3).

3 - in November of 2014 I had a heart attack[1]. That derailed everything that was going on. Physically I recovered fairly quickly, and 5 months later I was back to doing 6 hour MTB endurance races. But it was a turning point mentally and emotionally. I wound up basically doing nothing for all of 2015 that related to the business. I just didn't care anymore. Any "momentum" we had dissipated. I think my partners decided it was over and while they never really said "we quit" they just kind of disappeared. Not that I blame them. I was fairly incommunicado for a year or so, and anyway I'd always been the "visionary" and the one doing probably 85% of the development anyway. It was always more "my baby" than theirs.

So entering 2016 I decided it was time to get focused again, but I felt like the industry had shifted and that it was time for a new direction. ML stuff was starting to get hot, and AI had always been the "thing" underlying most of my passions in CS and tech. Sooooo... the "thing to do" was obviously to build an AI as a Service offering.

So I started on that, built some cool stuff and had maybe just a little bit of momentum going again. And then the weirdest thing happened. A guy found our website and some of my old Quora posts, was smitten with our old product suite idea, and called up and said "I want this at my company."

A blessing right? Well... not so much. I mean it could have been, if I'd handled things differently. But I made the mistake of offering to made modifications / additions to the code to accommodate his requirements - without asking him to pay anything or otherwise commit anything. You can probably guess how this ends. I spent months ignoring the AI as a Service offering to work on the old product, and then his company had a re-org, got a new CTO, and all interest in our stuff died. So, no sale, and I more or less wasted, let's call it 6 months, not working on the AI stuff.

Then some churn in my personal life led me to a new day job, where I felt like I couldn't continue working on the AI thing as there would have been too much overlap with my day job, and too much risk of possible accusations of IP conflict or whatever. So that got back-burnered. And during the 2 or 3 years I was at that job, I nearly cried everytime I read an article in the press that was some variation of "XYZ ML / AI startup acquired by FOO for 72 Gazillion dollars."

:-(

Anyway... that's my story through about 2 years ago. If you're wondering "how does it turn out?" I can only say "keep watching." :-) I haven't stopped, and in fact I made a conscious decision to change day jobs and take a job with NO AI connections at all, just so I could feel confident getting back to work on my stuff. I don't feel like there's much need for a general purpose "AI/ML as a Service" offering these days (there are plenty of them), but I still think there's "meat on the bone" for various applications of AI in enterprise settings. So I'm adapting a lot of the work I did before in a slightly new direction and am still optimistic about getting back on track in the near future.

Sorry, guess that didn't turn out as concise as I'd hoped. Sometimes that happens when you start writing.

[1]: https://news.ycombinator.com/item?id=8550315