As I’ve thought more deeply about how to answer this question over the years, I’ve come to a realization that the problem is not the answer, but the question itself. For those who’ve asked it, I don’t think it’s always coming from a place of “quick money.” If we reframe the question, I think there’s room to empower and actually help those who’ve asked it—to give them a foundational understanding of what it really means to generate an income online.

Immediately after I graduated from business school, a lot of people began asking me what I would do, or if I’d found a job. The answer was almost always “working a few hours a week on some side projects until re-launching my startup.” Whereas this may sound like an unfortunate or undesirable outcome, really was not so bad… My gross income then — without really “working” on anything — was higher than it was when I was working 80 hour weeks running a $3M/year eCommerce company. Sure, it wasn’t glamorous, but it was all part of a strategy that would eventually lead me towards “accidentally” building a 7-figure media business that runs whether or not I show up to work this month. Let me explain…


So many great tips in this big post, thanks! I think it’s so true that people should focus on the things they do well at and are interested in. And yes save, save, save in the beginning and throughout. I have several interest and dividend earning investments and am looking to expand further. Diversification is a great goal for all of us so we can avoid having all our eggs in one basket.
I have to agree. Our Duplex cost us 200k initially in 1998. Over time and completely refurbishing the property with historically appropriate sensitivity, we invested another 200k or so. We just had a realtor advise us we could ask 700k for it today. It nets us 30k annually after taxes, insurance and maintenance. We still have a loan on it which I have not taken into account, that will be paid off within 5 years if we keep it. My mental drama now is, while I am quite giddy over the prospect of earning a tidy sum of profit if I sell, what then would I do to equal the ROI and monthly income this thing generates? Rents are low, they should be 4k a month and will only go up. Tempted to keep it and not sell. And while I do have some stocks, I basically suck at them. I am much better at doing properties.

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 you balance sheet obliterated.
2. You clearly have plenty of money already. Just more padding in your already cushy nest. This is not the story for a lot of people. Your title should be “How to become richer than you already are without working.” But, actually the investment one is the only one that would make money without actual WORK. Running rental properties is a lot of work, and so is running a business, or even a blog. Sooooo…..while there might be some truth to this, I think it’s mostly grass that looks greener because it’s on the other side of the fence.

That $200,000 a year might sound like a lot to you, but the median home price in San Francisco is roughly $1.6 million or almost eight times our annual passive income. For a family of three in 2018, the Department of Housing and Urban Development declared that income of $105,700 or below was "low income." Therefore, I consider us firmly in the middle class. http://wolfe-investments.com/wp-content/uploads/2017/10/Blog-Passive-Income-Through-Real-Estate-848x450.jpg


* I use Personal Capital to track all my finances in one place. It’s much easier to use their free software to follow 28 accounts on one platform than to log into various accounts to check my balances. They’ve also got great tools for x-raying your portfolio for excessive fees, recommending a more optimized asset allocation, and planning for retirement with their Retirement Planner.
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