From what he describes, creating passive income definitely does not sound easy. It requires a serious ramp-up -- often requires 80- to 100-hour workweeks in the beginning, says Flynn. But once up and running, and depending on the content, some sites take fairly minimal maintenance. Green Exam Academy, the LEED exam study site he launched in 2008, takes just him four to five hours a month to maintain but brings in $250,000 annually.
For someone my age, I have an extremely low risk portfolio of mutual funds, foreign currency, and bonds. It’s made a bit more risky by my recent exposure to cryptocurrency, but that’s the only “high risk” activity going on here. Nothing exciting, but it pays some nice dividends and beats the hell out of keeping money in a savings account. This is a way for me to hedge against the risk I incur by angel investing in startups.
Stock dividends: Some stocks, especially stocks from big corporate standouts, pay dividends to shareholders based on the number of shares they own, and the percentage of the stock price on the dividend date. For example, if a company pays out 3% on a stock that's trading at $100 per share, you'll earn $3 for every share of that stock you own. Add it up and that can be good take-home pay as a passive investment.
A Risk Score of 10 means no risk. A Return Score of 1 means the returns are horrible compared to the risk-free rate. A Feasibility score of 10 means everybody can do it. A Liquidity Score of 1 means it’s very difficult to withdraw your money without a massive penalty. An Activity Score of 10 means you can kick back and do nothing to earn income. To make the ranking as realistic as possible, every score is relative to each other. Furthermore, the return criteria is based off trying to generate $10,000 a year in passive income.
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.
When I started building my architecture-related business in 2008, I made my first dollar through advertising. I’d spent a lot of time and money building the site and getting traffic. Then one day I threw an ad on the site one day, and I made $1.18. Sure, I could find that much under my couch cushions—but that’s not the point! The point is that I was able to build something online, put an ad up, and make money without having to do anything. I learned it was possible, and it motivated me to move forward.

For those of you who don’t want to come up with a $220,000 downpayment and a $900,000 mortgage to buy the median home in SF or NYC, who don’t want to deal with tenants or remodeling, and who wants to not do any work after the investment is made, check out Fundrise. They are my favorite real estate crowdsourcing company founded in 2012 and based in Washington DC. They are pioneers in the eREIT product offering and they’re raising an Opportunity Fund to take advantage of new tax favorable laws.
It is probably the biggest digital products marketplace online. Clickbank uses a very helpful measure called ‘gravity’ to represent how well a product sells, based on how many sales have been made and how recent these sales were. There’s one thing you want to be aware of though! ClickBank will withhold payment of any balance until an account shows a minimum of 5 sales using at least two types of payment methods. Not only that, if you made a sale but had no earnings for an extended period of time, your account will be subject to an ongoing penalty. This means that your affiliate earnings can potentially drop to zero. Nowadays, I rarely promote Clickbank products.
Dividend Income: Dividend income is wonderful because it is completely passive and is taxed at only 15% if you are in the 25%, 28%, 33%, and 35% income tax bracket. If you are in the 39.6% income tax bracket you will pay a 20% tax on your dividends. My dividend income portfolio mainly consist of dividend equity and bond ETFs such as DVY, VYM, MUB, TLT, and IEF. Total stock and bond income is a little over $100,000 a year due to a heavy accumulation of stocks and municipal bonds after selling my house.
Focus on your primary passive income stream first. It's difficult to grow your passive income into multiple streams if you don't already have one, solid stream. Focus all of your efforts on that one project first and help it grow as productive as possible. Then, you can take the money you've made and lessons you've learned from this passive income stream and put them into others.
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. 

So many people are seeking lucrative ways to earn income passively, and default to investment properties to do so. Unfortunately, there is a lot of effort that goes into starting a rental property business, especially if you choose to manage your property on your own rather than employ a property management company. That is, however, not to take away from the positive cash flow that is possible from real estate investment if done properly. Thanks again for sharing the realities behind earning “passive” income through your rental properties.
What I’m doing: My realistic goal is to have a blended annual return of 2x the risk free rate. With a current 5% hurdle, I am not paying down mortgages that cost less than 4%. Debt at 5% is a wash. My realistic blue sky scenario is a 3-4X rate of return over the risk free rate which can be achieved with property, stocks so far for the past five years, and certain private equity investments. Where I am dragging is my blended average CD interest rate of roughly 3% from an old CD coming due. I’ve rolled some money into a 12-month CD with CIT Bank at 2.5%. It’s the best rate I can find. 

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.
If retirement is a goal of yours (and who doesn’t want to retire someday?!?), it’s important to learn how to start investing. In fact, funding your retirement accounts should be at the top of your list. While these accounts won’t help your immediate situation, by stashing cash now, the residual income they create should help propel you through your golden years.
Anthony, nice setup! To your question about the rental mortgages, you haven’t said what interest rate you are paying. As a start, if you are paying more than the risk free rate (Treasury bills) which you probably are, then a true apples to apples comparison would be yes, pay off the mortgage. But, if you are comfortable taking more risk, you have other options to invest in which you *hope* will yield you more over the coming years. You also didn’t say whether the rentals generate net income and if so, how much? What is the implied rate of return on the equity you have invested in them? If you pay the mortgages off, you’ll have even more equity tied up, will the extra net income make that worthwhile? Maybe you should use the money to buy more rentals instead, if purchase opportunities still exist in your town. … this is less of an answer than a framework to analyze the decision, hope it is helpful.
Creating a membership site is a powerful way to generate online income and scale a service-based business. By having members pay a monthly (or other periodic) fee to get access to a password-protected area where exclusive content is made available, you can transform a site into a RECURRING income-generating business and bring a regular flow of income from the same customer base.
Creating passive income is the key to retiring, especially retiring early. If you want to retire early with the stock market you will have to save a huge amount of money, because that money has to last so long and retirement calculators depend on you using your investment to fund your life. With passive income you will have income coming in as long as you own the investment, without every eating away at the principle invested. Creating passive income may take more work than investing in the stock market, but I think it is well worth the extra effort!
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