Those who choose to focus on passive income will need either family money, funds from investors, or the nerve to borrow large sums by taking on debt to fund the purchase of assets. Consider someone who takes out substantial bank loans to build an apartment building or buy rental houses. Although this can turn a very small amount of equity into a large cash flow stream, it is not without risk. When using borrowed money, the margin of safety is much smaller because you can’t absorb the same degree of setback before defaulting and finding your balance sheet obliterated.
It’s obvious that stocks outperform real estate in terms of capital gains, but I would like to see S&P compare to Real Estate in SF, Manhattan, LA. Our house in NC was $80,000 20 years ago. It’s only $150,000 now. Same house in Santa Monica went from $200,000 to $1.8 million. People who happen to bought real estate in major metropolitan would have a natural positive association with real estate investment.
I personally don’t care about being seen as rich – I don’t need the fancy house or cars. I just want to know that I can give up some or all work whenever I’d like to, and spend that time with my family without any financial pressure. I remember reading somewhere that “wealth is measured in time, not dollars” – and I believe that to be totally true. If I ever got a tattoo, that phrase would be highly considered to end up somewhere on my body.
It shouldn’t come as a surprise, but people who regularly monitor their finances end up wealthier than those who don’t. When you were a kid, keeping track of all of your money in a porcelain piggy bank was pretty easy. As we get older, though, our money becomes spread out across things like car payments, mortgages, retirement funds, taxes, and other investments and debts. All of these things make keeping track of our money a lot more complicated.

EVA is the incremental difference in the rate of return over a company's cost of capital. Essentially, it is used to measure the value a company generates from funds invested into it. If a company's EVA is negative, it means the company is not generating value from the funds invested into the business. Conversely, a positive EVA shows a company is producing value from the funds invested in it.
One thing I’ve realized is this: It’s FAR easier to work for an employer than it is to develop durable passive income streams for the average person. Why? Because working for an employer in a place that “needs” you means that it’s possible to show up and give a 50% effort. You can show up, put in your time, go home, have a beer, watch TV, and rinse and repeat all without REALLY having to put in the effort.

For example, you can design digital products, like animal clipart or a downloadable wedding poem that could be printed by the customer. Your design could be resold thousands of times without needing to create each item or ship it. Once you create your digital product and list it on a site like Etsy or Ebay, the revenue flows in with little oversight.
Airbnb is a concept that has only been around for a few years, but it has exploded around the globe. Airbnb allows people to travel all around the world and to stay in accommodations that are a lot less expensive than traditional hotels. They do this by staying with participating Airbnb members who rent out part of their homes to travelers. By participating in Airbnb, you can use your residence to accommodate guests and earn extra money just for renting out space in your home.

Leveraging the internet to create, connect, and sell is something every creative person should attempt to do. The only risk is lost time and a wounded ego. You can start a site like mine for as little as $2.95 a month with Bluehost and go from there. They give you a free domain name for a year. Forget all the add-ons. Not a day goes by that I’m not grateful for my site.
I enjoy how you lay out real numbers. A lot of people wouldn’t do that. While you admit that you are somewhat conservative, I think the $1M in CD’s is just too conservative. Assuming you don’t need the cash flow now (which you say you just save anyways) then all that could be invested for potentially higher returns. For example, what if you bought San Francisco real estate along the way instead of CD’s. Or, an SP500 Index fund. I bet your average return would have been higher than 3.75%. Sure you could lose it, but the point is if you don’t need the cash flow now, you should try to increase that nut as high as possible until the day you actually need it. Your nut could be $5M right now if you had invested in asset classes other than CD’s for the last 14 years. Don’t get me wrong, you have done far better than me, but I guess I would take a little more risk if you don’t rely on that cash flow.
If you’d prefer to skip the startup phase, you might want to buy a blog that’s already built and earning revenue. This is actually pretty easy to do as a lot of people start blogs, and then get bored with them. Getting a blog going is a labor-intensive process, and it’s not uncommon for people to give up before they’ve reached their full potential.
Real estate is the obvious choice if you are going to make money on your money. I personally am not at the point where I can do any of this in a meaningful way BUT my parents are and they now own a couple homes outright and are collecting income from them to power their retirement income. It makes a lot more sense for anyone that has a chunk of cash sitting in the bank and are planning on slowly drawing from it because you technically still have all that money in a property (or multiple properties) and can sell them if you really need the lump sum of cash but you’ll earn great interest payments until you do that.
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