He mentions co-founding a company and never had a "real" job but his title is all about being a remote worker for a company.
There's a HUGE difference between being a remote worker FOR a company, and a remote worker for YOUR OWN company.
In the employee / company case, you have someone telling you what to do work on day to day and probably report to them on a regular basis for progress. You have no chance to spiral out of control because if you produce low quality or no work over a few days or a week you'll get reminded by your employer that they are paying you to do work.
In the entrepreneur case, you have no one for that and then it's very easy to get into trouble.
I've been working remotely for ~20 years (for my own freelance / teaching business) and I find it super simple to find motivation to work on client work because someone is requesting I do something for them, and they pay me in return (similar to a "real" job).
But for the teaching (creating and selling video courses) side of things, it's much harder to grind through everything because there's no real deadlines (other than being irrelevant if you take too long, which is a serious threat but you typically don't think of that during your day to day). I imagine someone working on a startup as a solopreneur could have the same issues, because it's the same thing.