The 4-hour mindset becomes more useful when it's time to scale. The problem is an unwillingness to do "unscalable things" at early stages, which just comes down to being too lazy to be an entrepreneur.
Surprised there aren't more comments since I found this article very interesting.
So in light of this article, much of the behavior that the author describes sounds a lot like "sales" the very thing I have found missing. And, because it sounds and feels like sales on some superficial level it is easy to imagine for the practitioner that they are just around the corner from the big win.
I thought this article was interesting and touches on your experiences:
It's not a feature problem—Avoiding Startup Tarpits
Parts sounded very similar to the start-up that I was referencing most directly in my comment. The big difference was that in selling to large enterprises, marketing is very inefficient at reaching decision makers.
We thought we had this in hand because our founder and a couple of key early employees were deeply integrated into the CIO community. And, we did succeed in getting CIOs on board. The real challenge though for us was that revenue depended on adoption and ongoing use within large enterprises. While CIO's were telling us this platform is really great and we will have 20 procurement projects hosted on your exchange in the next 6 months, they weren't willing to force adoption within their organization. We would get delays and then maybe 1 or 2 projects and then nothing. There was still something missing or a unidentified barrier when it came to the needs of a VP or director 2 levels down from the CIO.
Eventually we ran out of money. The technical foundation was really good and allowed the founder to run it solo until he found a larger service company that wanted to retrofit the technology to support their business model. He got a smallish buyout which in theory made him and the investors whole plus a little. The last I heard they were having legal wranglings to actually get the money paid out from the acquiring firm.
Hiring managers, are you paying attention?