Let’s use Jim from our personal finance example. Jim’s furniture manufacturer builds tables and has several large pieces of equipment in the sawmill used to re-saw logs and boards down to the finished dimensions. The sawmill has net operating revenues of $100,000 for year. The saws in the mill cost Jim a total of $500,000 and he is currently earning a return of 10% in his wholesale table business. Thus, he sets a minimum required return of 10 percent.

If you need cash flow, and the dividend doesn’t meet your needs, sell a little appreciated stock. (or keep a CD ladder rolling and leave your stock alone). At the risk of repeating myself, whether you take cash out of your portfolio in the form of “rent”, dividend, interest, cap gain, laddered CD…., etc. The arithmetic doesn’t change. You are still taking cash out of your portfolio. I’m just pointing out that we shouldn’t let the tail wag the dog. IOW, the primary goal is to grow the long term value of your portfolio, after tax. Period. All other goals are secondary.

Investing your money is one of the oldest passive income strategies on the books. Investing in stocks (or funds of stocks) means that you are becoming a (very) partial owner in the company whose stock you own. When you purchase a stock, your expectation is that the value of the stock will either increase or decrease, and your goal is to buy low and sell high. (This is what everyone is shouting about on the floor of the NYSE in movies about the world of high finance).
I wanted to specifically call out one particular strategy within equity investing that bears mentioning – dividend growth investing is when you focus on stocks that not only pay a dividend but have a history of strong dividend growth. When I was first building my portfolio of individual stocks, I focused on buying companies with a history of dividends, a history of strong growth, and financials that supported a continuation of both.
So, if the goal is to have residual income when we retire, which seems based on Social Security rules to only be possible in our 60’s, and the government has mandated penalties before taking our money before 59.5, wouldn’t it be prudent to start investing in sources of residual income now that maybe don’t have an age limit into our 60’s? What guarantee do we have that we will make it that long?
Many individuals may be seriously overestimating how much money they need to start investing in passive income properties. It is true that it may require millions for some to retire. However, as Harvard Business has recently reported; if investors focus more acutely on income versus nest egg size, they may achieve more with less. This is specifically true for those that intelligently use leverage. In real estate, for example, you can quickly scale to controlling millions of dollars in property, and their cash flows.
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In 2012, even I wrote a 150-page eBook about severance package negotiations that still regularly sells about ~35 copies a month at $85 each (2nd edition for 2017) without any effort. In order to generate $2,975 a month or $35,700 a year in passive income as I do now, I would need to invest $892,500 in something that generates a 4% yield! To earn $10,000 a year in passive income would therefore need roughly $250,000 in capital.
I prefer assets that make me a high return for the lowest amount of work possible (semi-passive involvement). And assets that pay me in several unique ways. Cash flow is only one way RE makes money for me. I also get principal reductions, appreciation, tax advantages (depreciation), and I control the rental increases on a yearly basis. Plus a majority of the capital is provided by the secondary market on 30 year fixed low interest rate debt.
And real estate does more than just track inflation – it throws off income (which is important to some people and useful to most). And while your underlying asset is appreciating, the income also grows as rents increase over time. And if you make smart and well-timed purchases, both rents and asset values can increase at well above the rate of inflation.
The reason I consider dividends artificial and believe they don’t matter is because you can just as easily reinvest your dividends. If a stock is worth $100/share, I don’t care if it issues a $1/share dividend or if the share price instead increases to $101/share – either way, I have the same amount of money, because there’s no difference to my net worth whether I take the dividend or sell part of a stock.
Venture debt ($12,240 a year): The first venture-debt fund has returned almost all my initial capital, so I decided to invest $200,000 in the second fund. I took a risk investing $150,000 in my friend's first fund, so I'm hoping there's less risk in the second fund, given he has four more years of experience on top of his 12-plus years of experience running a venture-debt portfolio for another company.

Peerstreet – This residual income option is slightly different, helping you earn money using real estate backed loans instead of the property itself. By helping fund the loan, you’ll earn a percentage of the interest rate charged to the borrower. Most loans are short-term, generally lasting between 6 and 24 months. You can build your own portfolio by choosing the exact loans you’d like to fund, or Peerstreet will choose the loans for you. Again, you need to be an accredited investor, although the minimum investment here is just $1,000.
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