Money from dividends, for example, are taxed at a lower rate than money from a job. A business owner who works in the company she or he founded would have to pay more self-employment payroll taxes compared to someone who merely had a passive interest in the same limited liability company who would pay only income taxes. In other words, the same income earned actively would be taxed at a higher rate than if it were earned passively.
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.
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.
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.
Consider refinancing your mortgage if you haven’t done so in a while before interest rates go up further. Or consider leveraging cheap money responsibly to acquire hard assets. LendingTree Mortgage has one of the largest lending networks online, and they will contact you immediately with their offers. You want lenders competing for your business, and get hard quotes so you can pit them against each other.

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”.
We are going to start with 1.5 years of all spending needs in cash. We will draw 1800 to 1900 per month. We will add to this from the index funds by taking a portion of the gains in good years to supplement. This is the total return portion of the equation. Obviously, if stocks decrease drastically over a 5 year period, then I would have to reload by selling some of the ETF holdings.

I invest about 5% of my pre tax income in 401k that my employer matches. Have close to 70k in cash in checking. Also,I liquidated around 40k in my 401k and not sure where to invest that in (bonds vs stocks) because of stocks trading at record high. Have a rental property that is paying itself now and I will pay off the mortgage completely in 5 years. My immediate concern is the cash in checking acct that’s not doing much. Thanks for your reply and appreciate your work. I am learning a lot
You don’t have to invest individually to take advantage of dividend paying stocks (i.e. investing in an ETF like DVY, which currently has a 3.16% dividend yield – almost 4%). And while your math is indeed correct, there is more to dividend paying stocks that just the math. The reason the companies pay dividends is typically because of their underlying strength, steady growth, etc. These companies can be good investments for the long run. As such, it might not make sense to sell.
One of the most important assets you have is your credit score. By taking care of it and pursuing the steps to improve your credit score, a world of opportunity can open up for you. If you need a loan to buy that rental property or some quick funding through a business credit card, a good credit score will help you get approved so you can build passive income.
It’s a (mostly) short term, higher risk, higher reward place to invest cash that has a low correlation with the stock market, but is far more passive than buying and managing properties, has more opportunity for diversification than private placements (minimums of 5-10K, rather than 100K), and most of the equity offerings (and all of the debt offerings) provide monthly or quarterly incomes. Unlike a REIT, you can choose exactly which projects you wish to invest in.
A perfect example of the Active Problem Solving + Automation concept is in my online courses I’ve created over the years, or my free webinars I’ve created more recently Each of my online courses and webinars are targeted to help people with specific problems, whether that’s in the area of affiliate marketing, podcasting, building a brand, and so forth. I am always improving upon the courses, but they are also evergreen for my audience.
Some people take it automated well before the year is up. When it converts, it converts. If you target the right people and you're able to create the right message that appeals to your audience, you might just hit a home run. An automated webinar often involves the creation of a webinar funnel. That includes, not only the webinar, but also the email sequences, and possibly a self-liquidating offer, and maybe some done-for-your services and up-sells.

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.
I personally haven’t tried any of the below methods so I can't speak from experience to how they work. In my mind, the most lucrative way is through building a REAL business online and providing your visitors with great value. However, after some thought, I decided to include these here because, quite often, the biggest roadblock for many is a mental one: believing that making money online is possible. From my experience, once you have made your first dollar, or even your first cent online, the world is suddenly a different color.
One of the great parts about the online world is that a website and its domain name is like real estate - It can go up in value over time. In fact, sometimes just the domain name without the developed business can be worth quite a lot to some people. Of course, like almost anything mentioned here, the necessary know-how is required. If you’re willing to put some time into it, then you can earn a nice online income. So far I sold 4 domain names with an average price tag of a couple of thousand dollars. Nice income, considering I bought each domain for around $10….If this income stream interests you, check out flippa.com - It’s one of the best marketplaces I know for selling websites or domain names.
Another great way to get started is to identify an area of interest you have. For instance, Robert Duff has been successful in building passive income by selling books on Amazon. Then, go out and start talking to people. Ask them, “What are you struggling with right now? What are your biggest pains? What’s something you wish existed that doesn’t?” That’ll give you some ideas about where to get started.
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.
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.
This is a venture that is growing rapidly. You can create videos in just about any area that you like — music, tutorials, opinions, comedy, movie reviews — anything you want . . . then put them on YouTube. You can then attach Google AdSense to the videos, which will overlay your videos with automatic ads. When viewers click on those ads, you will earn money from AdSense.
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.
5) Determine What Income Level Will Make You Happy. Think back to when you made little to no income as a student. Now think back to the days when you just got started in your career. Were you happy then? Now go over every single year you got a raise or made more money doing something else. How did your happiness change at all, if any? Everybody has a different level of income that will bring maximum happiness due to different desires, needs, and living arrangements. It’s up to you to find out your optimum income level.

As a private lender, you can lend to anyone in your social circle. For example, many home rehabbers need access to a source of capital they can tap into very quickly in order to fund the initial purchase of their properties. You can partner with a rehabber who uses your capital for a short-term in exchange for an interest rate that is mutually agreed upon.
As an struggling young Engineer (back in the Carter era) I bought anything I could renovate then rent to justify paying the 18% interest. I never took vacations but worked on my properties all in the pursuit of passive income. I drove junk for many years & many months I just got by on credit cards. My friends & colleagues were amused by my ‘stupidity’ but most are still working to make enough for retirement.
I have a total of three CDs left. There is no way in hell I’m selling them after holding them for 4+ years so far to take the penalty. The CDs are for 7 years. That would be completely counterproductive. As a result, I feel very stuck with ever getting my CD money back if I wanted to. If the CDs were for just 1 or 2 years, I agree, it doesn’t matter as much. But combine a 7 year term with 4%+ interest is too painful to give up.
I have only dabbled in drop-shipping before when I had an eCommerce platform 6 years ago or so. I think it is something that you could do on the side, but you would want to do in depth research on the industry you want to get into before setting up shop. It may be a little less passive up front, but over time you could take your hands off the wheel.

Affiliate marketing means you sign up with a company and/or entrepreneur and sell their products. For example, if you start a tech website, you could become an affiliate of a web hosting or anti-virus software company. You can earn hundreds or even thousands of dollars each month if your website receives a decent amount of web traffic and you have thousands of email subscribers. Being an affiliate marketer takes dedication and time. You need to build traffic via your website, email marketing and social media. Is this for you? You be the judge.
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Another way to generate passive income is to invest and be a silent partner in a business. This is very risky, but with risk comes the potential for high returns. For example, several years ago both Lyft and Uber were looking for private investors to invest in their companies. Today, they are worth billions - but you as an investor would only reap that benefit if they go public via an IPO, or get acquired. So, it's risky.

One aspect you might want to add to your scoring is “inflation protection”. At one end, bonds and CDs generally pay a fixed nominal coupon that doesn’t rise with inflation. Stock dividends and Real estate rents (and underlying property value) tend to. Not reallly sure how P2P lending ranks- though I suppose the timeframes are fairly short (1 year or less?) and therefore the interest you receive takes into account the current risk free rate + a premium for your risk. Now that I think about it, P2P lending probably deserves a lower score in the activity column than bonds too (since you probably need to make new loans more often).
Inspired by you, I started a tax/personal finance a month ago. I figured if it works out, it will create a good side income for me. If not, at least I can use the blog to build my brand as a tax lawyer. Other than that, my current investment portfolio is heavily focused on index funds because of its historical performance and tax & cost efficiency. Right now my dividends income every year is about $14,000. I also have a good amount of unrealized capital gains every year from my investment, though I don’t count the capital gains as my passive income as they are paper gains, at least for now.
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!
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