When I sold my company, the buyers were both thrilled and surprised that I was willing to accept such a large portion of the proceeds as structure payments. For 5 years, I received a monthly check, including interest, for the sale of that company. I created the value a long time ago, added a little more value by allowing payment over time, and thereafter that value was paid on a schedule.

I just found your site & so far I like what I see. I am 50 years old & will be retiring at the end of Jan 2019. I turn 51 the following month. I will have a pension income of $60,000 per year & an additional $5,400 from a survivors benefit. I was able to save $200,000 in a deferred comp program through my employer & wish to know what to do to generate a passive income? I can leave it in the plan which will generate about 3.5% or invest it. My concern is the tax liability of taking out a large sum from that fund & leaving me less to invest. I do have an opportunity to invest in a bar/restaurant with family (my main concern) that currently generates $120,000 annually for an absentee owner. It would be a 3 way partnership if I did that. I do like your idea of creating my own product such a blog with a goal of $12,000 to $18,000 passive income I feel that may be my best option. Any thoughts or advice would be greatly appreciated.


Though it requires a huge up-front investment (well, at least 20%), real estate is awesome, because it’s (usually) pretty stable, and it’s a triple-whammy: you make money by leveraging a bank’s money, you can rent it out with almost no work at all day-to-day, and the value of the underlying asset INCREASES. This is why so many people flock to AirBNB to rent out their apartments when they’re going on vacation, too. It’s pretty passive, you don’t have to own the asset, and you just hand over keys and hire a cleaner before/after. The value of your apartment is untouched. By contrast, imagine buying a plane and renting it out to people for tours — you pay tons of money to maintain it, and after 20 years, it’s value is almost nothing. The exception is if you can manage depreciation and somewhat automate the value-delivery. If you have an expensive tool (like a 3D printer) and charge people to come over to your house and print things on your 3D printer, it’s pretty passive for you to answer emails and open the door, so I give it a “Semi to yes” for passivity.
I have two major dilemmas: (1) Should I wait to start investing (at least until the end of the year where I’ll hopefully have $5k+ in savings) in things like CDs? I ask because a little over $2k doesn’t seem significant enough yet to start putting my money to work (or maybe it is? that’s why I’m coming to you for your advice haha) and (2) I want to invest in things like P2P and stocks but I’m honestly a bit ignorant of how it trully works. I know the basics (high risk, returns can be volatile, returns are taxable). Do you have any advice on how I can best educate myself to start putting my savings to work?
I don’t really know much about those…I should take a look from a diversification standpoint. If you don’t mind me asking, what do you target for your net effective tax rate on your passive income? Also, I’m sure you’ve probably covered this somewhere, but how do you deal with healthcare? One more dumb question…have you found that you spend more or less money than you anticipated once you retired?
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.
Personally, my experience with Amazon thus far has been good - a few of my short eBooks generate steady passive income on weekly basis with zero additional effort from my side. One thing to note though - Amazon pays 70% royalty on each eBook sold only if your eBook is priced between $2.99 to $9.99. Less than or higher than that pricing structure, the royalty decreases to 35%.of your book’s listed price.
There are really two ways to invest in real estate, direct purchase of property and investment indirectly where you don’t have full control of the property. Direct purchase involves a larger up-front cost but generally higher potential returns. Indirect investment can be made through real estate investment trusts (REITs) or tax liens but does not involve the immediate or direct ownership of the property.
Since David may never be coming back to this site, If anyone other than David can point me in the right direction, Id greatly appreciate it. I live in Chicago, and I need to buy a quality rental to hold long term somewhere but I have no idea where, and I really don’t want to buy in Chicago. Chicago is insanely corrupt and in HUGE debt. I cant leave Chicago in the near term, I take care of an aging parent, and if I left, my salary would drop by 50%. Id still like to diversify into a rental property.. but I feel that if I just call up a stranger, they’d attempt to sell me their best pig with lipstick, and pressure me to jump on the deal before someone else ‘stole’ it. I have no problem hiring a property inspector from a different city, but don’t want to waste hundreds of dollars if the agent is steering us towards crap property after crap property. I’m looking for broad advice. Any constructive reply appreciated. Thanks guys.

What's crazy is that my book income is more than my SF condo-rental income. Yet I didn't have to come up with $1.2 million of capital (the minimum cost to buy my condo today) to create my book. All I needed to create my book was energy, effort, and creativity. I truly believe that developing your own online product is one of the best ways to make money.
As I’ve thought more deeply about how to answer this question over the years, I’ve come to a realization that the problem is not the answer, but the question itself. For those who’ve asked it, I don’t think it’s always coming from a place of “quick money.” If we reframe the question, I think there’s room to empower and actually help those who’ve asked it—to give them a foundational understanding of what it really means to generate an income online.
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.
Residual income is money that is earned on a recurring basis, typically as the result of a single original action. Rather than earning an hourly wage, residual income is typically generated through an initial investment of time or money with the goal of earning continuous payments. Once the initial investment, product, or service is made, the ongoing income that is earned is generally passive in nature.

Thank for this extensive work. When you make extra money you need to think simple. First thing you should consider is whatever you do must be safe enough that you don’t lose your initial investment as well. Also, look at the ways you can reduce your costs. This could be car insurance savings or paying back expensive loans or card balances. Saving is making money as well.

I agree mostly with the real estate advice. I’m looking for ways to take advantage of the condo I own to get up the rent from ~$0.90/ft to the $1.2-1.5/ft that seems more like the range in the same area. I’d have to put in a bit of capital (probably 10k on the low end for just the basics up to 40k if I wanted to remodel the kitchen and 2 bathrooms up to par with the area), so the return is likely there if those upgrades warrant $1.30/ft (given the unit is larger than most 2br/2ba in the area).
We pitched to an angel investor group. They were very excited about the idea but wanted to know who amongst us (doctor, accountant, salesman) was doing the coding. When they heard we were outsourcing it, the wind went out of their sails immediately. They did want to meet with us again once we brought a coder on board but that person proved elusive to find. Coders in our area are looking for the steady paycheck, not willing to gamble on a startup.
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.
For example, a three-year $10,000 loan with a Prosper Rating of AA would have an interest rate of 5.31% and a 2.41% origination fee for an annual percentage rate (APR) of 6.95% APR. You would receive $9,759 and make 36 scheduled monthly payments of $301.10. A five-year $10,000 loan with a Prosper Rating of A would have an interest rate of 8.39% and a 5.00% origination fee with a 10.59% APR.
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.
Rental properties are defined as passive income with a couple of exceptions. If you’re a real estate professional, any rental income you’re making counts as active income. If you’re "self-renting," meaning that you own a space and are renting it out to a corporation or partnership where you conduct business, that does not constitute passive income unless that lease had been signed before 1988, in which case you’ve been grandfathered into having that income being defined as passive. According to the IRS, "it does not matter whether or not the use is under a lease, a service contract, or some other arrangement."

Wow! What an awesome list! My favorite is the stock photography because I love photography. I have had some success there, particularly with one photo I make some decent income from. I think the key with stock photography is finding a shot that is high demand. Then, find a new unique way to frame that shot. This is the reason my St. Louis Arch photo is a top 10 on both ShutterStock and iStockPhoto. Thanks for the awesome ideas above!


Network marketing or multi-level marketing is one of the most popular passive income streams. When you join a network marketing company, you become part of a team. The goal, for some, is to become a leader, such as a district manager of your area, because you can earn more money. The drawback to network marketing is poor leadership and the emphasis on building teams quickly. If you join a team with a weak leader, you won't like network marketing. But if your leader knows how to build and develop people and teams, you could be successful, earning $5,000 or more per month. A word of caution: read the fine print when you sign up. Make sure you have ample time to quit if you decide the opportunity is not for you.
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.
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.

I have already come up with 50 ways that a management company can screw you for profit without you ever knowing(or not finding out for awhile). Did you have an inspection before you made an offer on the property? Do you have a picture of the property you bought? How do you know if that picture shows the house you actually own? or if it even hows the ‘current’ state of the house you own?
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