Immediately after I graduated from business school, a lot of people began asking me what I would do, or if I’d found a job. The answer was almost always “working a few hours a week on some side projects until re-launching my startup.” Whereas this may sound like an unfortunate or undesirable outcome, really was not so bad… My gross income then — without really “working” on anything — was higher than it was when I was working 80 hour weeks running a $3M/year eCommerce company. Sure, it wasn’t glamorous, but it was all part of a strategy that would eventually lead me towards “accidentally” building a 7-figure media business that runs whether or not I show up to work this month. Let me explain…
In February 2007, Pat Flynn was working at an architecture firm making $38,000 a year. He mulled boosting his earning power by getting an architecture license, but the process would likely take six to eight years. When he heard about getting a credential in sustainable design and environmentally friendly building called Leadership in Energy and Environmental Design (LEED), he decided to go for that, as no one in his department had it. The one problem? The exam was so challenging, just one-third of test-takers passed.
This is the best post I’ve seen on passive income streams. I’m similar to you in that I worked in IBanking for a few years but wanted out. My approach is a little different, instead of starting with the CD’s, I’m trying to build up my net worth with riskier asset classes such as stocks and real estate to get the benefit of compounding. Then, as I approach my retirement year goal, I’ll start moving them into CD and bond ladders. In theory at least, it’s best to have the highest net worth just before retirement, then convert them to risk free passive income. You’re method is more patient and probably more practical than mine. I guess I’m willing to take more risks.
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.
We have 1 rental at the moment and we are renovating the second one. Last year we generated over $14,000 net passive income (after mortgage payments and taxes) from one apartment, and all I had to do was go in to inspect the property 3 times to make sure the tenants weren’t destroying it! It turned out they kept it in perfect condition and they were lovely people! Call me lucky.

Crowdfunding is a newer way to invest, having emerged onto the scene just within the last few years. Most people have heard of sites like Kickstarter and GoFundMe, and a very similar concept exists for real estate. Developers are always looking to raise capital to fund their projects. Through the various online platforms, investors have access to these projects and can choose to invest in both residential and commercial properties. See the List of My Favorite Crowdfunding Sites.
This can be a little easier said than done, but if you have a large social media following, you can definitely earn money promoting a product or advertising for a company. You can even combine this with different marketing campaigns if you are an influencer and have your own blog (advertisement + affiliate income). This is how many bloggers make money! Again, it is not 100% passive but once set up correctly and then scaled, can be surprisingly lucrative.

That strategy seems waaaayyyy less risky than actively picking stocks of supposedly “reliable” stocks that issue dividends, which could be cut at any time due to shifting industry trends and company performance. Dividend investing feels like an overly complex old-school way of investing that doesn’t have a very strong intellectual basis compared to index investing.
Those who choose to focus on passive income will need either family money, funds from investors, or the nerve to borrow large sums by taking on debt to fund the purchase of assets. Consider someone who takes out substantial bank loans to build an apartment building or buy rental houses. Although this can turn a very small amount of equity into a large cash flow stream, it is not without risk. When using borrowed money, the margin of safety is much smaller because you can’t absorb the same degree of setback before defaulting and finding you balance sheet obliterated.
Domain names cannot be replicated. If one is taken, the only recourse would be to approach the owner to discuss a sale. While there are other variations you could choose, sometimes owning a certain domain (especially if it is attached to your business) can be worth the premium. Often, people will scout out domain names that are still available, buy them, and then sit on them in order to sell them down the road. Depending on who may want the domain down the road, you could sell it for a large markup.
If an investor puts $500,000 into a candy store with the agreement that the owners would pay the investor a percentage of earnings, that would be considered passive income as long as the investor does not participate in the operation of the business in any meaningful way other than placing the investment. The IRS states, however, that if the investor did help manage the company with the owners, the investor's income could be seen as active since the investor provided "material participation." 
2. This article isn’t intended to be about making $50k per year from $0 to start with. This is intended to show different ways that it’s possible to generate $50k in passive income. As for your rental property comment, check out RealtyShares or other similar companies. You can be a rental property owner without having to run the business. You can be a limited partner and just invest in real estate, and leave the actual work to the general partner. Basically, there are options to make $50k without working, but like the first paragraph says – front load your life!
John has a daily (yes, daily) podcast where he features an interview with a successful entrepreneur. Now, John enjoys many hundreds of thousands of downloads per month, he’s written a book, has products and has opened up a ton of opportunities for sponsorships and partnerships that wouldn’t have come otherwise. He’s not the first person to have a show dedicated to interviewing rock star entrepreneurs—not even close—but he’s definitely the fastest to see these kinds of results.