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.
Within six months of selling, however, I had reinvested the proceeds from the home sale and brought total passive income for 2018 back up to an estimated $203,724. I'm not sure I would have sold the house without a clear plan for reinvesting the proceeds, since I'm bullish on the SF housing market long term. However, because I did have a plan, and the challenges of raising a newborn and dealing with rowdy tenants left me feeling a bit stretched, I decided to simplify and sell.
You must sacrifice the pleasures of today for the freedom you will earn tomorrow. In my 20s, I shared a studio with my best friend from high school and drove beater cars worth less than 10% of my annual gross income. I'd stay until after 7:30 p.m. at work in order to eat the free cafeteria food. International vacations were replaced with staycations since work already sent me overseas two to four times a year. Clothes were bought at thrift shops, of course.

Which all goes back to my point – since companies change in a lot of unpredictable ways, it makes more sense for passive income to just ride the market by investing in a Total Domestic Stock Market, Total Bond Market, and Total International index funds, with allocations that depend on your goals and time horizon. For income, withdraw 4% or less, depending on what research you believe, and you’ve got a pretty low risk strategy.
Developing passive income is different. With the exception of one of my passive income streams (cryptocurrency mining), all of the others require real, hard work. Truly, I understand the barriers for people getting into building alternative income streams. I would say that most people WANT passive income, but truly aren’t willing to put in the blood, sweat, and tears to make it happen.
To create residual income, you need to create something that people will continue to buy on a regular basis long after you’ve created it. A house is a prime example of this as people will continue to pay rent for the right to live in the house. A business needs to have products that are sold over and over again rather than trading the business owner’s time for money.
I’m a 45 year old business owner who also has focussed on diversifying my income streams. I have a short term vacation rental in Florida that I bought for $390k in 2012 and net rental income for the last three years has been growing steadily. 2015 I am at $70k gross right now but should end up at $80-85k with net around $45k plus we use the place about 35 nights a year.
It’s a (mostly) short term, higher risk, higher reward place to invest cash that has a low correlation with the stock market, but is far more passive than buying and managing properties, has more opportunity for diversification than private placements (minimums of 5-10K, rather than 100K), and most of the equity offerings (and all of the debt offerings) provide monthly or quarterly incomes. Unlike a REIT, you can choose exactly which projects you wish to invest in.

If you're looking to get started in real estate, look at a crowd funding solution like RealtyMogul. It works similar to LendingClub - you commit as little as $5,000 towards a property. When the property is fully funded, you become an owner, and will receive your share of the earnings and appreciation in the property.  Check out RealtyMogul to learn more. 
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