Part of his schtick depends on that arrogance- who would believe you if you weren’t sure of yourself – and that’s the hard thing for most people to mimic. You can’t manufacture charisma. He’s a reasonably attractive fellow in a “short clean-cut white boy” sort of way, but does that bit where he’s loud enough and sure enough of himself to make him seem bigger. I found it a bit off-putting, actually, since he seemed to be performing all the time; this may have been exacerbated by my gender, as he appears to do the conscious “look at me, I’m charming” thing to women. All women.

Anyway, back to the premise of the book.
Automating our earnings is a good thing. Whether this gets translated into owning a business that requires minimal/no input or investments in the stock market, you want your money to be working for you while you sleep. This is solid basic investment theory. Hourly wages are a good base, but can’t change your situation by orders of magnitude like a good investment can.
However, as you’ve noted, he’s gaming the system. There are limited slots available for this tactic; the whole world can’t do it. (Sort of like my caveman diet.) Not to say that those who can shouldn’t, but it’s not, and will never be a solution for more than a tiny number of people.

That said, the number of people who can figure out what they would do with that free time and actually do it is even lower than the number of people who can carry it off, so the numbers will always stay low. It’s primarily an abstract aspirational concept, used to drive more $$ for Tim’s extensive vacations.

First, I already didn’t like Tim Ferriss before I read his book, for pretty much the reasons you folks list.

However, after reading it, I decided that I’m not mad at him; I’m mad at the world for allowing his strategies to work. Not his fault that he’s taking advantage of a system I don’t like in ways that work for him.

Re: “middleman”: middlemen add value, period full stop. If you get me something I couldn’t or wouldn’t have gotten without you, then you earned your cut. That’s his game.

Re: expertise: for what it’s worth, I am the world expert on teaching vocal percussion (which is as fun to say as it is blatantly true). My instructional DVDs turn out to have been the best return on time investment I’ve ever made. Then again, the market was definitely there (something Ferriss recommends you research a lot more thoroughly than I did… lucky me).

Is Ferriss a jackass? Don’t know. Never met him.

But does following his advice make you a jackass? Ay, there’s the rub. I don’t have the answer. Not yet, anyway.

As far as retiring and going mobile, I haven’t found any specific resources about that, but I’m pretty sure you know the answer. Figure out what your expenses would be in that lifestyle so you have an investment income target, and reduce your expenses now so that you can save and increase your investments until they generate the income you need to retire. This can be helped on both ends by being willing to accept a less opulent lifestyle both now and later. I mean, if you go truly mobile, and don’t have to pay rent/mortgage, I bet you could live comfortably on, what, $12k a year? Save up $240k, stick it in a high-interest CD at 5%, and you’re done.

But the point I wanted to talk about was, “He recommends selling things like training CDs or DVDs in an area where you are perceived as an expert (see below for how to achieve that).” Some colleagues of mine in the Minneapolis area did just that–they sank a load of money into a set of DVDs aimed towards builders for improving energy efficiency. They completely lost their shirts–they could barely give them away. It might have been problems with the target audience (i.e., builders who would rather see a real person talk), the price point (I remember it being pretty darn high)–but there was no disputing that they had established themselves as experts in the field previously.

I think that my company is trying to do at least part of the ‘automate’ portion–they are putting together an informational website–there’s not enough content right now to justify charging, but I believe they are talking about context-based ads. No idea if that would ever turn a profit, though.

As for “Get rid of stuff that you own that ties you down and keeps you from being mobile.”–yeah, that sounds like a pretty neat idea… I think that is an intrinsic part of my ideal retirement plan.

As I’ve said, I fall into the Gen X stereotype of not wanting to Achieve Great Things–I just want to make enough to be comfortable and get out. I was thinking of putting together a blog post about it sometime. Have you found sources that talk specifically about that topic?

In some sense, he’s basically just a middleman who takes a cut. While I suppose that’s fine if all you’re trying to do is make enough to live and not work, I guess I want my life to actually have brought some value to the world. Yeah, making videogames isn’t curing cancer, but I still feel like I’m contributing something.

The way you’ve framed it, it sounds like the intention is basically to exploit the general public’s ignorance in a field to achieve a completely superficial “mastery” of it, in order to turn the perception of knowledge into cash. I do know someone like that – David Freeman, of the Freeman Group – he manages to turn supposed knowledge of game writing into a lucrative career, but the guy is the most ingenuous jackass I’ve ever met, and every time I even think of the guy, I wish he would be catapulted into the sun.

I don’t want to live my life that way, I suppose.