There are three main categories of income: active income, passive income and portfolio income. Passive income has been a relatively loosely used term in recent years. Colloquially, it’s been used to define money being earned regularly with little or no effort on the part of the person receiving it. Popular types of passive income include real estate, peer-to-peer (P2P) lending and dividend stocks. Proponents of earning passive income tend to be boosters of a work-from-home and be-your-own-boss professional lifestyle. The type of earnings people usually associate with this are gains on stocks, interest, retirement pay, lottery winnings, online work and capital gains. 
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 actually spent a year and a half working as an affiliate marketer (mostly selling drumming related products – lessons, kits ect). 5 years on and one of my one page sites (which I’ve not touched) still nets me about $150 a month. I won’t be retiring off that but only really now appreciate the reverse pyramid approach to entrepreneurship (working for nothing initially but later being paid without effort!)
Skillshare is more of a social learning platform where you can teach real-world skills. The range of skills that you can teach is only limited by your imagination - from board game strategies, garment construction, cooking tutorials, travel hacking, and relationship tips. I even saw a course on how to build a grown man's wardrobe. Creating a class on Skillshare is free. For each student who enrolls, Skillshare takes a 30% fee (Similar to Udemy). You are also provided a unique teacher referral link that lowers the fee to 15% for students who enroll via your referral. Note that all online courses on Skillshare go through an approval process based on specific criteria.
That means you visit properties, review their tax histories, ensure the local market is robust and has sound long-term potential and the local rental market is one that is favorable to landlords and property owners. If you have to compete to fill your units and pay high taxes in areas where potential rental income in limited, you made a bad business decision and will have trouble generating passive income from your real estate investment. But so long as the property and market are good, you can make money.

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.


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But first, let’s about talk passive income! What is passive income? There are many different definitions out there, but mine goes something like this: Passive income is all about building online businesses that can work for you, that allow you to generate income, and grow and scale, without a real-time presence. In other words, you don’t trade time for money. You build something up front that can continue to work for you over time.
After these tenants move out, I'm thinking of just keeping the rental empty with furniture. It sounds stupid to give up $4,200 a month, but I really hate dealing with the homeowner association, move-in/move-out rules, and maintenance issues. Given that the condo doesn't have a mortgage and I have to pay taxes on some of the rental income, I'm not giving up that much. The condo can be a place for my sister, parents, or in-laws to crash when they want to stay in SF for longer than a week or two.
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.
When a taxpayer records a loss on a passive activity, only passive activity profits can have their deductions offset instead of the income as a whole. It would be considered prudent for a person to ensure all the passive activities were classified that way so they can make the most of the tax deduction. These deductions are allocated for the next tax year and are applied in a reasonable manner that takes into account the next year's earnings or losses.
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