My saving/investing strategy is governed by a few guidelines and realities: 1. I have a family (meaning I have more costs and more immediate investments I nee

My saving/investing strategy is governed by a few guidelines and realities: 1. I have a family (meaning I have more costs and more immediate investments I need to make, for example in the education of my children) 2. I believe that investing in my own company where I control the money and the effort involved has a vastly superior return than investing in a company that already had an IPO. There's no way those companies do the return on my funds, like my company does, if for no other reason than that they are already through their major growth phase (they already IPO'd). Add to that the level of control I have in my own thing, and it's clearly advantageous to invest there. 3. I believe stock purchases are akin to gambling. This expands my universe of possibly investments to other forms of gambling. It turns out that with some knowledge and practice it's possible to tilt the odds in your favor. Given these rules and considerations I have a threefold investment strategy: Cash is king. I keep large cash deposits available at all times, both in actual cash and in the bank. I invest a regular amount of my earnings from my job into my side business and my side business provides excellent returns and I've developed a way to scale those returns that I'll be testing this month (the ability to use in a leveraged way the money I invest into my side business, but with a higher maximum cap than I could reasonably put into the business). For my high risk, high reward "investment" I cut out the stock market altogether and literally go to a casino. I suppose the final part of my portfolio might be the most surprising to HN. I can report that I've had excellent results in the casino. Sustainable advantage playing is possible. In 2009, I bought a vehicle outright with the proceeds from this portion of my portfolio. If I didn't have a family, I'd be doing a more aggressive version of this where I'd have larger cash holdings (no family = way more money left over every month), I'd invest more in my side business, and I'd risk more at the casino. Your goal should be to produce a machine that makes you money without your involvement, normally this is called a business, but if you have enough money, then the money itself can be this machine (through interest). To have that amount of money where it is sustainable requires roughly $4 million in cash (I've seen this number other places, the fabled "FU" money). It my belief that it's much easier to build a business that produces say $100k a year with minimal involvement on your part than it is to produce $4 million in cash (though it should be noted that if you produce a business that produces that much profit you're on your way to being able to trade it for $4 million in cash).