This is my private email correspondence with one of the closest people in my life suffering with debilitating failure and depression. One email on the topic of finance:
“Dear xx,
I think I can give you a piece of advice that might be very beneficial. I don’t think most people can sort through what I’m going to tell you and have it stick or make any sense. But I think you and I have similar levels of motivation and ambition in life. I think I know THE money shortcut in life. I think I know the THE hack. I know the secret ingredient for guys like you and me. And here it is; free of charge, from me to you: Money is very important. It’s one of the most important things in this life. But it’s not really HOW MUCH you have, but rather it’s HOW YOU GET IT and how you manage it. As quickly as possible in this life, find a method for making $3k-$10k a month from a semi passive biz that can be done from a computer sitting anywhere on earth. If you can get this done, you will have 90% of the freedom, time, and benefit that multi millionaires have.
I am a very happy guy. I got it done! Money has made so much of this possible. But it’s WAAAAY overkill. There’s no need for $10mm or even $1mm. My happiness has come from not worrying about paying for charges on my credit card, not reporting to a boss, being able to stay up late, buy healthy food, or travel the world for several month stretches. Those are my moments of undisputed happiness. But all of that can be had on $5k a month if you manage it properly. The greatest feeling in the world is standing at the airport with a tattered passport, a little foreign cash, good music playing in your earbuds, feeling healthy and looking good, heading out on a trip that you have no idea when you’ll be back or where you’ll even end up going.
After the first $1mm not much changes. Taxes go up, stress goes up, expenses go up, overhead goes up with higher levels of insurance, estate planning, and expectations. With whatever little is left would the second Ferrari really add much to your life experience? The freedom of millions can be fantastic but the same “millionaire lifestyle” (or much better) can be had pulling in $5k from your blog or online consulting gig. And yeah, $5k is approx what the guy with a million bucks decently invested will pull per month after taxes and inflation.

Guys like Tim Ferriss talk about this concept dubbed “The New Rich”, also called Digital Nomads. The idea is to keep expenses low, live in a rental house or Airbnb, use Uber or public transit, develop marketable skills online, build a brand, market yourself, and buy yourself freedom in very short order. Buying cashflow producing assets like rental houses or apartments plays just fine too! (Remember I’m a RE guy at heart… <3 )
This idea makes some people crazy because you will technically have to work “forever”, but the reality in my mind is this: Motivated folks will want to work forever anyway, you should choose something you love to do, and if you manage your time and keep mobile, none of this will bother you. There’s a treacherous lie pushed around by many in the entrepreneurial community: That you’re supposed to retire. You’re supposed to quit and suddenly be complete, having arrived. There’s no such thing as this. Stay engaged. Love what you do, but just do it on your own terms! Your time, your place, your speed.
Bottom line: when you’re ready to bounce, buy your freedom as quickly as you can with an online gig that will get you $3k-$10k a month, then figure yourself out, and figure out what to do with the rest of your life and build an organization around it. (biz or religions, or nonprofit, government, or whatever)
I’ll stop now. I’ll go try to get those books sorted.
Later,
Will”