Tim Ferris is a fascinating person. The most interesting thing about Tim Ferris is how thoroughly he understands the concept of leverage. Every successful tech entrepreneur understands the concept of leverage too. Tim Ferris is extraordinary in how he has applied leverage to every aspect of his life.
Tim Ferris thinks in terms of lifestyle optimization. He decides what he wants and then he maximizes it. Most people do not do this. Default human behavior is to look at the options presented to you and then select one of them. Selecting from an option someone else created positions you on the low-payoff end of the Gale-Shapley matching algorithm. You'll get the worst result among all stable matchings.
You cannot maximize leverage unless you get into the habit of proposing things. You should propose deals, arrangements and transactions with all kinds of people in all kinds of circumstances all the time. Corollary: If you don't like an offer then it is usually a good idea to try to negotiate. After all, you have nothing to lose.
I rarely reject offers outright because there is usually a price at which I'll do something. A recruiter recently tried to get me to work for <major tech company>. I demanded half a million dollars per year in exchange for a maximum of 20 hours per week. The recruiter turned me down but sometimes bold offers like this actually work. A few months ago I offered to provide a few sentences of high-level recommendations for someone's blog at $50 per post. I thought it was an absurdly high price point until he/she sent me the first payment.
Most of my offers aren't transactional. They're more along the lines of "Want to go on a 60-mile bicycle ride with 3,100 feet of elevation gain (and loss) roundtrip next Saturday at 10 am?" Of course, I only ask this if someone has already shown an interest in cycling. My go-getter attitude is one of the things my friends like being around me. They'll come over to hang out for a few hours. By the time they leave they're committed to three months of powerlifting.
People generally like being propositioned provided: