We’ve discussed how to get started building passive income for financial freedom in a previous post. Now I’d like to rank the various passive income streams based on risk, return, and feasibility. The rankings are somewhat subjective, but they are born from my own real life experiences attempting to generate multiple types of passive income sources over the past 16 years.

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.
I have six rental units which are a good source of passive income. I don’t use a property manager because you are right…they take about 10% of your rent. There are really only 2 things that tenants call about: 1. A plumbing issue 2. Heat/Air problems. Just find a plumber and heat/air guy you can trust. I travel a lot for my primary job. When a call comes in from a tenant, I can call the repair guy in just as easy as a property manager.
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Another benefit, which many online entrepreneurs do not even consider, is that you don’t need to create the whole product before launching it. You only need to create a small portion of your actual content, and complete it only after you get your first member during his membership - that means you get paid IN ADVANCE of actually creating your site content. It also means that you can modify your content based on LIVE feedback from paying customers. More importantly, this is a great way to VALIDATE your site and ensure you create a product based on what customers want, not just what you think they want.
Depending on how many rental income properties you have and your experience with home improvement, you may be able to do a lot of the maintenance yourself. You likely won’t be able to fix everything but it will be worth it to learn a few common repairs to do yourself. Typically, plumbing and electrical maintenance will cost the most since work is generally restricted to licensed members of the trade unions.
Book sales ($36,000 a year): Sales of How to Engineer Your Layoff" continue to be steady. I expect book sales to rise once the economy starts to soften and people get more nervous about their jobs. It's always best to be ahead of the curve when it comes to a layoff by negotiating first. Further, if you are planning to quit your job, then there is no downside in trying to engineer your layoff so you can get WARN Act pay for several months, a severance check, deferred compensation, and healthcare.
Book sales ($36,000 a year): Sales of How to Engineer Your Layoff" continue to be steady. I expect book sales to rise once the economy starts to soften and people get more nervous about their jobs. It's always best to be ahead of the curve when it comes to a layoff by negotiating first. Further, if you are planning to quit your job, then there is no downside in trying to engineer your layoff so you can get WARN Act pay for several months, a severance check, deferred compensation, and healthcare.
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My favorite type of semi-passive income was rental property because it was a tangible asset that provided reliable income. As I grew older, my interest in rental property waned because I no longer had the patience and time to deal with maintenance issues and tenants. Online real estate became more attractive, along with tax-free municipal-bond income once rates started to rise.
Amazon affiliate program is a great way to promote physical products through a reliable, trustworthy, and well-known online store. The fact that everyone knows Amazon is probably their biggest advantage. On the downside, commissions are fairly small - they start at 4% for most products and can go as high as 8% depending upon how many sales you make. However, when you send someone to Amazon, you earn a commission on whatever they buy within 24 hours of clicking your link, whether they end up buying the product you promoted or not. So, for example, if you promoted a book but the person you sent to Amazon ended up buying an expensive camera as well, you’ll get the commission for both the book and the camera. This can add up.
Venture Debt – I invested $120,000 in my business school friend’s venture debt fund. He started his own after spending 8 years at one of the largest venture debt funds as a Managing Partner. I’m very focused on income generating assets in this low interest rate environment. The true returns are yet to be seen, as the fund has a 5-7 year life before it returns all its capital.
4) Treat Passive Income Like A Game. The only real way to begin your multiple passive income journey is when you are making active income. The initial funding has to come from somewhere. Hence, treat passive income as a game that has various levels. If you fail to achieve one level, it’s not the end of the world since you still have active income and can restart. Furthermore, a game is meant to be played with integrity. Using shortcuts (non passive income streams), someone else’s income as a supplement (spouse), or one-offs (capital gains) does not count. The primary purpose of any game is to bring enjoyment to the player and beat the boss.
Investing in rental properties is an effective way to earn passive income. But it often requires more work than people expect. If you don’t take the time to learn how to make it a profitable venture, you could lose your investment and then some, says John H. Graves, an Accredited Investment Fiduciary (AIF) in the Los Angeles area and author of “The 7% Solution: You Can Afford a Comfortable Retirement.”
When you buy a turn-key rental property you are saving a lot of time and work, by letting the turn-key company complete the repairs, find the property and manage the property. You are giving up equity in the property over buying one yourself, because you aren’t doing any of the work. You have to decide if the time you save is worth the equity you give up. Typical returns I have seen on turn-key properties have been in the 10 percent range.
Earn rental income. One of the more common ways that people earn passive income is by buying and then renting out property. These can be homes, apartments, land, or even individual rooms within your home. To do so, you'll have to find a property to rent out, determine a fair rental price by looking at comparable properties in your area, and then act as a landlord for your renters. You can convert this income source into truly passive income by hiring a manager to act as a landlord for you. However, this may not be economically feasible until you have several rental properties.[1]
Teachable and Udemy are two of many, but these are the most prevalent, and they’re both intuitive and user-friendly. With Teachable, you have more control over your pricing and the look and feel of your course, but you don’t get a built-in audience. Instead you have to do all the marketing yourself. Udemy has a built-in base of students, but you don’t have as much control and they take more of your revenue.
Have you always wanted to own your own business? You could start a side business while you work a full-time or part-time job. For example, if you're a graphic or web designer, you could start your own graphic or web design business on the side. If you like to make jewelry, you could sell at craft fairs and online. Starting a business may be daunting, but if you believe in you and your work, you could earn a decent living, maybe even quit your day job. Search out those who are doing what you want to do and interview them. Find out the mistakes they made and ask for guidance.
Let’s continue the vintage BMW idea. Old cars obviously require quite a lot of maintenance. Many people will buy a “fixer upper” with the intention of spending their spare time repairing and restoring it. There’s a very obvious market here: a guide to restoring different BMW models. Depending on your knowledge, you could produce detailed guides for the three or four most popular models and sell them. Not everyone restoring a car will buy them, but some probably will.
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