Well, he makes money from his show and from conning rubes. What I'm saying is that his investing strategy is based around profiting from a crash and then when there was a big one, he didn't profit off it. Without exaggeration, a monkey could do better than him (assuming an untrained monkey rather than one that has learned or independently come up with Austrian "economics").
The issue is that he's stuck in the (early) 19th century, or he'd say that all knowledge attained since then is misleading or something. Early economists thought in terms of gluts and shortages. So if people shift from liking coffee to tea, coffee starts going unsold, shops are going out of business, etc., tea shops start seeing long lines and/or selling out of product. It looks like coffee is now too expensive and tea is too cheap, and the market corrects that, leading to more tea being produced/less coffee being produced and then to prices stabilizing. The thinking was that every trend toward a glut is balanced by one toward a shortage. But at times, it appeared that there was a "general glut" with no balancing shortage (think of the Great Depression). Everything seems too expensive suddenly. Some people thought that was a logical impossibility, but J.S. Mill figured out how to explain it within the glut/shortage framework. The shortage was in (think about it for a second if you want a challenge) ... money itself. To us, that was not the end but the beginning of the debate (rather than money, is it actually safe assets? high-quality assets? a mix?). That leads to a natural solution (if you think it's money as Friedman did, print more money; if you think it's safe assets, issue more bonds; etc.).
Well, Schiff never got the memo. He thinks that there was a period of "malinvestment" where the economy was built around false signals and thus we're effectively *unable* to supply the needs of consumers. So to go back to the coffee example, people still want it, but it just can't be made. In addition to this being obvious rot (just think about it), you can devise any number of tests to check it and see that it's rot. It also explains why he keeps predicting hyperinflation. If he's right, putting more money/safe assets/gov't spending into the system doesn't do anything to fix the problem and so you have the same constraints on production but more money to spend on the low number of goods. Should just drive prices way up without increasing growth. For the civilized among us, the Great Depression and WWII put an end to the debate. The aftermath of the GFC (both the impact of austerity in nations that went that route and the impact of fiscal and monetary stimulus in the U.S.) should have taught people who didn't learn from history.