The age old argument of total return versus income has been, incorrectly imo, categorized as an either or proposition. We are going to do both. Right now I have a lot cash in an on line money market. I also have investments in 2 passive Index funds in a taxable account. We then have substantial 401ks/IRA’s which we won’t touch for at least 10 years. My wife will continue to max out her sep and we will continue to invest in the index funds although with a smaller amount. We have already factored that in. I looked at how to cut into the monthly deficit. Here is what I observed.
The term “selling” probably doesn’t need much explanation, but it’s where value is transfered one time in exchange for money. Heart surgery, baguettes, and designer jeans are all ways to sell value. This one would probably the least optimal of all, at least for passive income, if it weren’t for an exception. This is because once you sell a normal commodity or service, you can’t re-sell it. Here’s the exception to this: software or digital goods can be duplicated with a very low marginal cost(now that we don’t use CDs, you can duplicate it with a cost of $0.00), and therefore, technically can be “sold” advantageously over and over and over again. This is why Microsoft grew to such a profitable company, and why I love selling digital goods.

Whether you take a “distribution” (aka free-cash-flow) in the form of a dividend, interest payment, capital gain, maturing ladder of a CD, etc, you are still taking the same amount of cash out of your portfolio. Don’t fall for the trap of sub optimizing your overall portfolio’s performance because your chasing some unimportant trait called “income”.
The challenge I’m facing and, I know it’s a good problem, is that the SF real estate has shot up about 35% in the last couple years. I’m sure you’re experiencing the same thing! So as the net worth is rising, the yield on the total portfolio is going down. Right now, it seems the only way to increase the passive income will be to raise the rent in December and to invest some of that cash in stocks, which I’m nervous to do in this market. Current allocation:
Self-publishing has the potential to be a very lucrative source of income. However, it does involve both an investment of your time and finances. It’s very important that you get the right help from the beginning. There are many considerations that may be outside of your expertise. Rory Carruthers, a sought-after book development, book launch, and book marketing consultant, says that six-figure launches require careful orchestration and planning. “Bestsellers aren’t just born out of great talent. They are also a product of thought-out marketing and well-orchestrated book launch campaign. It’s no longer enough to just write a good text. You need to think one step ahead and warm up your audience to the book even before you finish the first draft,” he said.
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. 

Sam…just read this article and I want to say that this is the best posting on passive income I have ever read…in a blog, article, or book. Thanks for making a difference and being an inspiration as to how it can all be accomplished. One of the great benefits of the internet is that people are willing to share their stories and experiences with each other online. If we had this when I was working professionally (20-40 years ago), it would have saved me from making some rather poor financial decisions that affected my retirement income. In a way, the internet is making up for the loss of financial security in the loss of The Defined Benefit Plan for retirement. Bravo!
I enjoy how you lay out real numbers. A lot of people wouldn’t do that. While you admit that you are somewhat conservative, I think the $1M in CD’s is just too conservative. Assuming you don’t need the cash flow now (which you say you just save anyways) then all that could be invested for potentially higher returns. For example, what if you bought San Francisco real estate along the way instead of CD’s. Or, an SP500 Index fund. I bet your average return would have been higher than 3.75%. Sure you could lose it, but the point is if you don’t need the cash flow now, you should try to increase that nut as high as possible until the day you actually need it. Your nut could be $5M right now if you had invested in asset classes other than CD’s for the last 14 years. Don’t get me wrong, you have done far better than me, but I guess I would take a little more risk if you don’t rely on that cash flow.
What I’m doing: I view passive income as funny money to keep myself sane during this long journey. I estimate 2-10 years to get to my goal depending on how active I am. The dollars created are just points one can accumulate. I’ve made passive income goals for each passive income type and check in at least once a year like I am now to make sure I’m on track. Passive income is also carefully managed to minimize tax liability. When you can build a buffer for a buffer, you are then free to take more risks.
Use your base to build your audience, and when you’re starting out, take advantage of the fact that you don’t have a big following to give more personalized help to your first fans. “The people who are starting out — that’s their advantage,” says Flynn. “They have the opportunity to speak directly with those people few coming their way to find out what their problems are and give them the special treatment that bigger brands might not be able to do.”

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.

2. Focus on income-producing assets. Internet growth stocks may be sexy, but they provide no income. To build a large enough passive-income stream to survive, you must invest in dividend-generating stocks, certificates of deposit, municipal bonds, government Treasury bonds, corporate bonds, and real estate. You're free to invest in non-income-producing assets for capital appreciation too. You just want to earn reliable income when the day comes to leave your job.
I have been a open minded driven dreamer since i was 18. Mix that all in with a complete screw up and you got my identity pretty much grasped…. There have been many different jobs that I have held since graduating High School. A side from my dads asphalt company and one landscaping gig I’ve been in sales my whole professional life. I am 33 years old and I know about the Insurance, Banking, Industrial/Electrical Manufacturing distribution, Telecommunications and Finally “online distribution” AKA: EBAY.
In order to build an audience, you need to have a platform. You need to have something worth following and sharing; something that’s valuable to others. And that, of course, takes time. That’s not to say you can’t build a huge audience in a short amount of time. But as much as we hear about the people who’ve succeeding at doing this, we don’t hear about the millions of others who are struggling every day to get just a few more fans and followers.
Everyone’s an expert in something. Whether you know how to knit infinity scarves or code software like a pro, earn money for your expertise by writing and self-publishing an ebook. Use a service like Amazon Kindle Direct Publish to help you reach a bigger audience, or market the product to your own audience and sell the book on your personal website.
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.
I will share what we did, because it’s an incredible success story. We used an existing tax loophole where if you sell your primary residence (after having lived there at least two years) you get to keep your profit tax-free. So, we stair-stepped. We bought house after house, at least two years apart, used the profit money to pay down on the next house (so on and so forth, yadda yadda) building up equity as we went along… and now, we own a $600,000 house debt-free. And now we are using our paid-off home as leverage to borrow money to buy commercial buildings to rent out. I like commercial because it’s a BUSINESS transaction… kids, pets, other wear and tear that you see with residential rentals is nonexistent. People take care of their business space much better than residential. You have to be in a good area for renting out commercial – a thriving business community – to make this work. But that’s how we “made it”, and though it took 15 years, we will have residual income to take care of us when we’re old enough to retire. People made fun of us for moving so much, but who’s laughing now? 😉 Oh, and our child only had to change schools once (and we wanted to anyway) because we stayed in the same general area as we moved around. We were careful not to disrupt his life too much.
This is such a fabulous piece. Thank you for your amazing efforts here. I was wondering -any initial thoughts on what one would charge an employer to post a job (for the idea about creating a site to help people with their resumes, etc)? I need to research for sure but was curious if anyone has any ideas on this. I have a background in the corporate world in management and recruiting and have been tossing this idea around for a while but am stuck. Thank you!
Hey Alison! thanks for taking the time to check out the post! I specifically outlined the post so it would follow a specific structure. This is so readers know what to expect and it helps with the flow of the piece. I’ve actually just finished up a (shortened) PDF version of the post that includes a bonus idea not mentioned here. I’ll be adding this to the post shortly! You’re right on the ebook suggestion — could easily have been made into one. I noticed that you linked to it from the millionaire blog post, thank you so much. Kimberly and I really appreciate the mention.
I had the same experience when my name’s frequency on the call schedule dropped for reasons that no one would discuss and were not easily discerned except by those in the know (who were staying mum). I went and found another job…. and I wish that I had found something with passive income – it’s been several years now that I’ve been working 2-3 part time jobs and I’m trying to figure out what my other thing is going to be… still working on that, but I am thankful that there are others out there discussing side gigs and alternatives to medicine.
However, when you lack the money, you need time. You'll need to invest the upfront time now in order to reap the benefits of automatic income later. It just doesn't happen overnight. So don't expect it to. However, you can do this without quitting your day job. All it takes is some sincere effort over a consistent period, and voila! But, to get there, you'll need to consistently burn the midnight oil or get up at the crack of dawn. Your choice.
But then, I started receiving more and more opportunities to spread the word and my mission. I was invited to speak at several national medical conferences, but I turned them down to maintain my anonymity. I was invited to meet up with readers whenever I traveled to different towns, but I turned those down for the same reason. What’s flattered me the most is that I’ve even been asked to mentor some people, but again, I’ve declined to stay hidden.
We usually think of Craigslist as a place to buy and trade random stuff, but Craigslist can actually be a great opportunity to sell your services online to an active and engaged audience. Simply check the “jobs” section and “gigs” section for specific cities and see if anything matches your skills. The great thing about Craigslist is that it is one of the highest converting traffic sources on the internet (think active buyers) which can mean more opportunities at higher pay.
Perhaps a coworker purposefully tries to make your life miserable because they resent your success. Maybe you get passed over for a promotion and a raise because you weren’t vocal enough about your abilities, and mistakenly thought you worked in a meritocracy. Or maybe you have a new boss who decides to clean house and hire her own people. Whatever the case may be, you will eventually tire.
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.

Flynn, who blogs at Smart Passive Income and discusses his secrets at the Smart Passive Income podcast, defines passive income as “building online businesses that take advantage of systems of automations that allow transactions, cash flow and growth without requiring a real-time presence. We don’t have to trade our time for money one to one. Instead, we invest our time upfront, creating valuable products and experiences for people, and we reap the benefits of that time invested later,” he says, adding, “It’s not easy. I just want to make sure that’s clear.”
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.
There’s a saying that the biggest opportunity for improvement is at the margin. Boiled down, this means that you can reap big rewards for minor adjustments in behavior. Instead of using a check, debit card or cash to pay for daily activities and big expenses, using a cashback credit card can earn you a sizeable return each year. One of my favorite cards, the Discover it will even double all of the cash back you earn the first year!
If someone stole my hard work and passed it off as their own, I’d be livid and would pursue them to the ends of the Earth for full restitution. A man I hired to work with me registered my preferred domain name of my business and has re-registered it in subsequent years. That’s bad enough; I’m mad as hell. The worst aspect of his behaviour is that I don’t know WHY he has done that; I paid him the fee we had agreed on and thanked him for his input. We also got along perfectly well during the project so far as I know, so I don’t see what his problem is.

One of the easiest ways to get exposure to dividend stocks is to buy ETFs like DVY, VYM, and NOBL or index funds. You can also pay an algorithmic advisor like Wealthfront to automatically invest your money for you at a low fee. In the long run, it is very hard to outperform any index, therefore, the key is to pay the lowest fees possible while being invested in the market. Wealthfront charges $0 in fees for the first $15,000 and only 0.25% for any money over $10,000. Invest your idle money cheaply, instead of letting it lose purchasing power due to inflation. The key is to invest regularly.
3) Create A Plan. Mark Spitz once said, “If you fail to prepare, you’re prepared to fail.” You must create a system where you are saving X amount of money every month, investing Y amount every month, and working on Z project until completion. Things will be slow going at first, but once you save a little bit of money you will start to build momentum. Eventually you will find synergies between your work, your hobbies, and your skills which will translate into viable income streams.
Because you’re publishing an eBook rather than a physical book, the costs are minimal. And you don’t have to print 1,000 copies of your book hoping someone will buy it. Instead, you can write your book, create a fancy cover for $5 using Fiverr and publish through services like Amazon Kindle Direct Publishing. Amazon will handle everything for you, then take a percentage of the revenue you generate.
Of course, you can make honst money in Internet info-products, or affiliate marketing, or other such areas where people tend to get drawn to "passive income" fantasies. But, to make real money over the sustainable long-haul, you must treat these like any other business. In other words, you must provide real value to real customers with a real need.
Depending on how many rental income properties you have and your experience with home improvement, you may be able to do a lot of the maintenance yourself. You likely won’t be able to fix everything but it will be worth it to learn a few common repairs to do yourself. Typically, plumbing and electrical maintenance will cost the most since work is generally restricted to licensed members of the trade unions.

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.
The great part about creating truly passive income is the money comes in every month without you having to sell your investment or worry about running out of money when you retire. The returns are also better for me with rental properties, because my cash flow is producing about a 20 percent cash on cash return and that does not even include equity pay down on my loans or appreciation. The appreciation on my rental properties is a bonus for me, while stock market investors are depending on it.
×