I just can’t seem to get my head around creating my own online product. When you talk about it, you make it sound like its mostly just about putting in the time and plugging away at it. Problem is I can never seem to come up with any ideas for a site or product that seem remotely unique or compelling or that I have any special knowledge about. The stuff I do know about is pretty commodity type knowledge that can mostly be found on thousands of sites on the internet already. Any tips on discovering what your “unique angle” is? I mean, you have a pretty compelling and somewhat unique personal story of working on wall street and then walking away at a young age.
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.
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.
Purchase the rights to royalties. Royalties are payments made for the use or sale of intellectual property, like a song, book, or trademarked product. These royalties are paid from the seller of the property to its creator. You can earn royalty payments either by creating the intellectual property yourself or by buying royalty rights from someone else. In the latter case, you can buy the rights for a lump sum and then receive regular royalty payments that will eventually return you your initial investment.[3]
The much loved model for bloggers and content creators everywhere and for a good reason…it’s pretty easy to write a 60-80 page ebook, not hard to sell say $500 worth a month through online networking, guest posting and your own SEO optimized blog, and well you get to keep a large whack of the pie after paying affiliates.  Hells yeah!  Continue reading >

If you know anything well, a place, how to fix something, how to make something, how to do something, you can write a guide for it. You can sell your guide as an e-book, offer it as a download for a fee on your site or reach out to bloggers with similar content and ask if they will offer it as a paid download on their website (for a price of course).

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.
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.

Freelancing is on the verge of going mainstream. Thirty-six percent of the international workforce now freelances, at least part-time. There are also 40.9 million adults in America who are self-employed. Clearly, freelancing is catching on. But with rapid growth come certain challenges, one being an increased competition for well-paying job and price reduction by those who think they can afford low-bidding at least for now. https://www.listenmoneymatters.com/wp-content/uploads/2017/08/LMM-Cover-Images-1.jpg
Remember, the skills you have are an asset, they are your “unfair advantage.” They are essential to your unique personal brand, and you can start making money online using those skills if you have the right strategy, tactics, and mindset in place. Another way to describe this is your “unfair advantage,” a term I was first introduced to by Lain Ehmann in SPI Podcast Session #37.
They've delegated, automated, streamlined, systematized, etc. Not with the intention of sitting on some beach somewhere for the rest of their lives and watching the checks roll in, but with the intention of freeing up their time to create even more value that they're inspired to create, either by leading that business to the next level of greatness and service to greater audiences, or by starting a new business.
Great job, note the home upsizing works only in appreciating housing markets (I’ve done a similar this in CA but it was 7 years same home to gain almost 500k profit which is around the govt cap for tax-free home profits. What a gift! Thanks booming economy and generous govt taxation on home profits). Those proceeds bought our next house cash and invested the remainder in domestic stock (which has been equally profitable).
For those of you who don’t want to come up with a $220,000 downpayment and a $900,000 mortgage to buy the median home in SF or NYC, who don’t want to deal with tenants or remodeling, and who wants to not do any work after the investment is made, check out Fundrise. They are my favorite real estate crowdsourcing company founded in 2012 and based in Washington DC. They are pioneers in the eREIT product offering and they’re raising an Opportunity Fund to take advantage of new tax favorable laws.
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!

Not really. I love my speed reading courses, I’m passionate about them. I loved working on apps to help small businesses kick more ass. Sure, it’s not as “sexy” as running a full time startup with dozens of employees, but that’s not the point. The point is to make enough money to be able to take risks and do what I want. Plus, if I’ve proven anything, it’s that you can turn these projects into full time if they become interesting enough to you.
Ask yourself how many hours a week do you spend sitting in silence, coming up with an idea and working on your idea? We’re so busy with our jobs that our childhood creativity sadly vanishes at some point in our lives. There are food bloggers who clear over $15,000 a month. There are lifestyle bloggers who make over $10,000 a month while living in Thailand. And there are even personal finance bloggers who’ve sold their sites for multi-millions.

Occupational therapist Sarah Stromsdorfer founded occupational therapy site MyOTSpot.com three years ago as an online educational resources for occupational therapy students and professionals. She worked on it every weekend, and her site now makes enough income for her to work as an occupational therapist part-time. She believes it will be another year before her site makes enough money for a full-time living of about $4,000 per month. In addition to the digital products she also makes money from ads and online book sales. 

This is separated intentionally from “information products,” because here I’m referring specifically to secondary value creation. If you can write a popular blog and get people reading it, you can sell ads. Alternatively, if you write a niche blog about vegetarian, gluten-free cat food, you can use special affiliate links to different websites, and get paid when people buy through those links. There’s lots of great blogs making tons of money doing these two things (I know of people making millions referring credit card signups), but please note that unless someone is writing and distributing the content for you, this is not passive income. It takes a lot of work to drive traffic. Some of the smarter people I know doing this have hired content writers and set up a bunch of sites, but they invest a TON of time on SEO, finding the right topics, etc.
​Udemy is an online platform that lets its user take video courses on a wide array of subjects. Instead of being a consumer on Udemy you can instead be a producer, create your own video course, and allow users to purchase it. This is a fantastic option if you are highly knowledgeable in a specific subject matter. This can also be a great way to turn traditional tutoring into a passive income stream!
I read about early withdrawal penalties on IRAs/401Ks very often. Almost always with a statement of “locked up” or “can’t touch” until 59.5. I’m sure you and well informed readers as well know about SEPPs in regard to IRAs/401Ks. For those that don’t SEPPs aren’t perfect but they are a way to tap retirement funds penalty free and I will be using in the future as I have over half of my equity investments within retirement accounts. South of a mil, North of a half. Let me add that I think your blog is outstanding. 

Question: You mention receiving $200k of passive income a year, but your chart shows half of that coming from real estate holdings, and reading between the lines it appears that you hold mortgages against those holdings. Then you conclude that $200k/yr of passive income should be enough to live comfortably anywhere in the world. So are you subtracting your real estate expenses (taxes, insurance, mortgage payments, maintenance, remote property management company fees, etc.) when you report your passive income from those properties? Really I think it’s the net (after taxes and everything) that tells us what is left over to “spend” on living, right? When I set up my spreadsheet to retire early at age 47, I calculated the after-tax income I would need to live. Then I compared that to my income streams (estimating tax on the taxable income streams) to measure the surplus/shortfall. Also some good advice from GoCurryCracker: If you can minimize your taxes so you’re in the 15% tax bracket, you can possibly receive tax-free long term capital gains. I agree with your philosophy that time is more important than money as we age. I am not sure I agree with a philosophy that is fixated on needing such a large income, and would rather minimize taxes if it’s all the same on the happiness meter. Furthermore, having 20 plus income sources in the name of diversification adds stress and requires more management (TIME!). I think this is fine for those of us while young, as we have the energy to work hard. But as time becomes more important, the extra headache of managing, planning, and buying/selling our assets becomes a resented hindrance on par with the resentment we felt when working for an employer and fighting traffic each day to go to a job we hated. Every thing we own in actuality owns us, by virtue of its demands on our time and affections, and that includes investments. It also includes our home, and is a good reason for downsizing. As long as we have food on our table, a roof over our heads, and clothes on our bodies, what more do we need? I think we need to consider freeing ourselves from the weight of the chains of managing too many ventures. Personally, I plan on investing in no more than 5 simultaneous ventures ever, with the exception of some IRAs that I just plan to let sit for the next 20 years (and therefore no thought or anxiety required).
As a general rule, the passive activity loss rules are applied at the individual level. Although Internal Revenue Code Section 469 was enacted to discourage abusive tax shelters, its impact extends far beyond shelters to virtually every business or rental activity whether reported on Schedules C, F, or E, as well as to flow through income and losses from partnerships, S- Corporations, and trusts. Generally, the law does not apply to regular C-Corporations although it does have limited application to closely held corporations. 

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.
But then figure out your unique selling proposition, what advantage you can offer that the market currently lacks. “My advantage in the passive income marketing space is that I’m not afraid to share my failures or where my income comes from,” says Flynn, who details his impressive income every month. “Transparency is huge,” he says. Referring to the personal bio on his LEED exam site, he says, “You might think I’m not benefitting from putting my story on there, but it helps me establish a relationship with people there. I’m someone who went through the same experience people went through on the site.”
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.
Anthony, nice setup! To your question about the rental mortgages, you haven’t said what interest rate you are paying. As a start, if you are paying more than the risk free rate (Treasury bills) which you probably are, then a true apples to apples comparison would be yes, pay off the mortgage. But, if you are comfortable taking more risk, you have other options to invest in which you *hope* will yield you more over the coming years. You also didn’t say whether the rentals generate net income and if so, how much? What is the implied rate of return on the equity you have invested in them? If you pay the mortgages off, you’ll have even more equity tied up, will the extra net income make that worthwhile? Maybe you should use the money to buy more rentals instead, if purchase opportunities still exist in your town. … this is less of an answer than a framework to analyze the decision, hope it is helpful.
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.
Truebill is an app that helps you save money by identifying recurring subscriptions and other bills and helping you cut costs by negotiating better rates and fees. One of their partnerships is with Acradia Power, which has the potential to save you up to 30% on your electric bill. It searches for better power rates in areas where competition is allowed, and it locks in the better prices for you.
There are a couple of problems with direct investment in real estate though. It’s expensive to buy even a single property, a minimum of tens of thousands of dollars, and there’s no way most investors can build a portfolio of different property types and in different regions to protect from those risks when you have all your money in just one or two investments.

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.
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