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.

One of his favorite tools is Personal Capital, which enables him to manage his finances in just 15-minutes each month. If you sign up and link up an investment account with $1,000+ within 40 days, you get a $20 Amazon gift card. They also offer financial planning, such as a Retirement Planning Tool that can tell you if you're on track to retire when you want. It's free.


Real Estate: I currently own one rental property in San Francisco which I bought in 2003 (2/2 condo), one vacation rental in Squaw Valley, Lake Tahoe (2/2 condo), and my primary residence. Real estate is my favorite asset class to build wealth because it is easy to understand, tangible, provides utility, and rides the way of inflation. I recommend individuals try and get neutral inflation by buying their primary residence as young as possible. The power of inflation is just too hard to counteract.
You are also free to choose a fund that is based on any index that you want. For example, there are index funds set up for just about every market sector there is — energy, precious metals, banking, emerging markets — you name it. All you have to do is decide that you want to participate, then contribute money and sit back and relax. Your stock portfolio will then be on automatic pilot.
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.
Returns on real estate investing vary and you don’t want to get into the business based on an estimated return but on your own calculation of what is possible for your local market and for specific properties. I have seen pretty common averages between 8% and 12% a year for single-family residential rentals with cash flow accounting for between 0% and 6% of the return.
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.

However, this comes back to the old discussion of pain versus pleasure. We will always do more to avoid pain than we will to gain pleasure. When our backs are against the wall, we act. When they're not, we relax. The truth is that the pain-versus-pleasure paradigm only operates in the short term. We'll only avoid pain in the here and now. Often not in the long term.
Also, if you pursue an income stream like affiliate marketing, your blog can be a source of content that allows you to link to affiliate sites in a way that is seamless and natural. For example, if you are an affiliate marketer for a company that sells productivity tools, you can blog about your own struggles to stay on top of your to do list. Then, you can mention how much those tools have helped you.
I've now only got an SF rental condo and a Lake Tahoe vacation rental in my real-estate-rental portfolio. Although I miss my old house, I certainly don't miss paying $23,000 a year in property taxes and another mortgage, and dealing with leaks and managing terrible tenants. I drove by the other day and couldn't believe how much noisier and busier the street was than where I currently live. I wouldn't be comfortable raising my son there.
Once your audience has grown and you have validation that you’re offering them value, there are many ways to create passive income. You could sell digital products like ebooks or courses, take up affiliate marketing in which you promote other company’s products and earn a commission when you sell that item to your audience, build a community and charge people to be a part of it, create software and sell that, among other avenues. Ask your audience directly what would serve them best, or look at what they’re saying on Twitter, Facebook or other websites, to find out what problems they have and how you could help solve them.
Of course, there’s nothing to say you can’t do both. You can manage your own commercial real estate rentals and flip houses while you have someone else help manage residential rentals. You can invest in REITs and real estate crowdfunding. You’ll get the higher returns of active management while benefiting from the diversification and ease of passive income through other sources.
Tenants usually move out before the court date but you may have to pay for a removal by the sheriff. All these fees and time delays add up and you can see why it is important to check tenant applicants in the first place. Having a formal eviction procedure will help avoid procrastinating the process and missing out on several months’ worth of rent trying to get tenants evicted.
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At age 55, I own high-end rental properties (near the beach) and commercial buildings servicing the medical industry. I was widely criticized during my career for not living up to my income; that is, buying big homes with many fancy cars. I married a great woman who understood that saving and investing today meant a better lifestyle and more freedom tomorrow. Our passive income is half of my active income from sales, but my net worth has increased substantially. We are both happier and healthier than we were in the high-stress pressure cooker of franchise sales. The naysayers have become converts to the concept of passive income, but they have locked themselves into a “big hat, no cattle” lifestyle. It has been a great ride!

Leverage: With the stock market, you invest your retirement savings or cash on hand. The same is true for private lending. You can leverage rental properties four-to-one, sometimes five-to-one, meaning your $50,000 investment can buy you $200,000-250,000 in real estate. In a rising market, this is a good thing and will maximize your cash on cash return.
Private money investing involves one investor with money, lending that money to another investor who needs the money. With real estate most private money is used to buy rental properties, fix and flips or even used by turn-key companies to fund their properties until they are sold to an investor. Private money usually is secured with a Deed of Trust against real estate, which provides more security than investing in the stock market. Returns on private money can be four percent or fifteen percent depending on the relationship between the investors and the risk involved.
I truly believe generating $10,000 a year online can be done by anybody who is willing to dedicate at least two years to their online endeavors. Here is a snapshot of what a real blogger makes through his website and because of his website. Roughly $150,000 a year is semi-passive income followed by another $186,000 a year in active income found through his site. Check out my guide on how to start your own blog here.
Another option: Consider starting your own real estate investment group. This is a great way to team together with other small investors, either via pooling your money together or simply by learning from eachother. According to Joseph Hogue, CFA from PeerFinance101.com, “The common bond in all real estate investing groups is that you help each other compete against the big money players to get the best returns.”
It was easier recouping the lost $60,000 in rental-property income than I expected. For so long, my primary mindset for passive income was rental income. Having $815,000 less mortgage debt but still generating roughly the same amount of passive income with a much larger cash balance feels great. Further, my passive-income portfolio got even more passive, which is good as a stay-at-home dad to a newborn.
“I don’t believe the overnight success exists. There’s a lot of hard work and time involved beforehand,” say Flynn. Angry Birds may have seemed like an overnight success but it was the 52nd game that Rovio created. Flynn says it took him a year or year and a half to build audiences for his most successful sites. (Read these time management expert's tips on the work habits of successful people.)
Venture debt ($12,240 a year): The first venture-debt fund has returned almost all my initial capital, so I decided to invest $200,000 in the second fund. I took a risk investing $150,000 in my friend's first fund, so I'm hoping there's less risk in the second fund, given he has four more years of experience on top of his 12-plus years of experience running a venture-debt portfolio for another company.

I am still working on my passive income, however I like multiple income streams even more. My favorite is capital gains because it is one of the lowest rates. One of the best passive income streams is a pension/Social Security. As I near retirement, I like the concept of it supporting my needs and my 401k supporting my wants. In addition, my brokerage accounts are all at capital gains rates. Don’t misunderstand, I am still working on adding more because I like multiple income streams!

You are valuable. Your time, your work, knowledge, experience, and output are all valuable. In fact, your employer (or your customers, if you’re an entrepreneur), probably pay a lot of money to rent these things from you. The problem is, whether you’re a doctor, a lawyer, an artist, an engineer, or even a baker, the value you create is consumed once — then it’s gone. You can only sell a loaf of bread once. You can only sell each open heart surgery to one client. The value trades hands, and now it belongs to the customer — you get paid once.
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.
Tenants usually move out before the court date but you may have to pay for a removal by the sheriff. All these fees and time delays add up and you can see why it is important to check tenant applicants in the first place. Having a formal eviction procedure will help avoid procrastinating the process and missing out on several months’ worth of rent trying to get tenants evicted.
Peer-to-peer lending ($1,440 a year): I've lost interest in P2P lending since returns started coming down. You would think that returns would start going up with a rise in interest rates, but I'm not really seeing this yet. Prosper missed its window for an initial public offering in 2015-16, and LendingClub is just chugging along. I hate it when people default on their debt obligations, which is why I haven't invested large sums of money in P2P. That said, I'm still earning a respectable 7% a year in P2P, which is much better than the stock market is doing so far in 2018!
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