I first discovered the power of passive income when I was a senior in high school. I started a mobile billboard business where I would rent a small piece of land from someone who had land along a busy highway. Then I would place one of my billboard trailers on the land and rent out the ad space on the billboard. I would usually charge about $300 per month for the ad space, meanwhile I was only paying $50 per month to the landowner for the ground rent. I got to the point to where I had 9 billboard faces and was making quite a substantial income for someone in high school. I really learned how passive income could free up my life… this business is what lead me into investing in real estate.
Passive income is an incredible tool that everyone should include in their retirement plans. With traditional investing you have to rely on the stock market to increase your investments over time. The longer you have your money invested, the more your money will grow. The stock market does not produce passive income, except in the form of dividends. Most dividends are extremely small and produce small returns on investment. The bulk of stock market returns come from an increase in stock market prices. The only way to realize those increase in value is to sell stock. Retirement calculators that use the stock market as an investment plan on you running out of money when you die because you have to sell all your investments to keep bringing money in.
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.

The biggest surprise is real estate being second to last on my Passive Income Ranking List because I’ve written that real estate is my favorite investment class to build wealth. Physical real estate doesn’t stack up well against the other passive income sources due to the lack of liquidity and constant maintenance of tenants and property. The returns can be huge due to rising rental income AND principal over time, much like dividend investing. If you are a “proactive passive income earner” like myself, then real estate is great.
Real Estate Crowdsourcing – After selling my SF rental house in mid-2017 for 30X annual gross rent, I  reinvested $550,000 of the proceeds ($810,000 total) in real estate crowdfunding, based in San Francisco. My goal is to take advantage of cheaper heartland real estate with much higher net rental yields (8% – 12% vs. 2% – 3.5% in SF) and diversify away from expensive coastal city real estate which is now under pressure due to new tax policy which limits SALT deduction to $10,000 and new mortgage interest deduction on mortgages of $750,000 from $1,000,000 for 2018 and beyond.
If you love design and you are an artistic person, selling digital products on Etsy could be a great way to earn passive income. Digital products require little maintenance, your customers will simply receive a link to download them (which means you don’t have to worry about shipping and returns handling). All you need to do is spend time upfront to create beautiful artwork! (Easy right?)
Now that you’ve chosen your market, find a way to start sharing your message, whether it’s a blog or podcast or Youtube channel, or whatever platform makes the most sense for your target market. Flynn says this is where you’ll start to build a fan base — and collect subscriber emails. You don’t need to get the whole world to follow you to make this work out financially. Wired cofounder Kevin Kelly wrote an article about 1,000 True Fans, which basically says that if you have 1,000 people paying you $100 a year, that’s a $100,000 a year. “You don’t need to serve everybody,”  says Flynn. 

The craziest part of this was I’d wake up in the morning and there would be more money in my bank account, from people who had bought my book overnight. When you think about it, an online store that sells something that’s digital is something that’s open 24 hours a day, 7 days a week, 365 days a year. Using tools, software and systems, you can automate the delivery process so you literally don’t have to do anything to serve that audience. That’s super powerful.
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.
Here’s the truth: a successful business is something that successfully solves a problem. And that business can make more money in two ways: solving more people’s problems, or solving bigger problems. The cool thing about the EP Model is that sometimes these products don’t even have to be yours. You can generate income by recommending other people’s or companies’ services or products. This is called affiliate marketing. It’s actually how I’ve made most of my money since I started in 2008.
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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