​Self Publishing is mainstream today. When you purchase an eBook off of Amazon there’s a pretty good chance you’re buying a self-published book. Self-publishing is also ridiculously easy. I tried this a few years ago and couldn’t believe how simple the process was. To self-publish a book you’ll first need to write and edit it, create a cover, and then upload to a program such as Amazon’s Kindle Direct Publishing. Don’t expect instant success though. There will need to be a lot of upfront marketing before you can turn this into a passive income stream.
This is certainly not in my wheelhouse, but time and again people have been able to make a lot of money from creating and selling an app.  You can offer the app for free to users, and if enough people use it you can then charge for businesses to advertise (just like #5) with you.  You can also offer a version of the app that has no advertisements, but the user must pay a nominal fee to have this version.  Either way once you have created the app and it is in the marketplace, it has a ton of potential to generate passive income.  Depending on the app, you could also be bought out by a larger company and given a lump sum to walk away.  This happened to Garret & Jessica Gee.  Garret developed an app that was eventually sold to Snapchat for $54 Million!
That said, from time to time I enjoy writing about some of the “other roads to Dublin.” Fancy investments are interesting and sometimes have different risks and rewards when compared with a basic index fund portfolio. Entrepreneurship has changed my life and that of many other physicians. Early financial independence opens all kinds of other doorways in your life. So in a blog about all things financial for high earners, from time to time I write about these other subjects. Today is one of those days.
What are your thoughts on an Immediate Annuity as a passive income vehicle? I suppose it’s not a great investment since you never get your principal back, but the risk is zero and the cash flow is fairly good, approaching 6% currently. And, since you are guaranteed payments for life, you may not care that you never see your principal again anyway since you’ll be dead!
Because passive investors’ rentals are viewed as secondary income, they can only deduct the normal costs associated with their rental properties. They cannot deduct any home office expenses and are limited on how much they can deduct from any losses they might incur. As of 2010, you can only deduct up to $3,000 from your other active income like your job or employment.
What about getting hit with AMT (Alternative Minimum Tax) in cases your passive income / capital gains are too high? I’m not that familiar with the details of AMT, but I got hit with AMT one time due to an “exercise and hold” of ISOs (stock options). My CPA explained it’s another method of calculating my tax liability, and in cases I gain too much capital gains, the IRS may treat and tax them as ordinary income.
In order for you to make the kind of passive income you would like you need to make sure the market segment you want to help has critical mass.  If you have the best widget in the world, but only 14 people need or want it, then you don’t have a viable business.  The great article 1,000 True Fans, by Kevin Kelly, cofounder of Wired Research, talks about if you have 1,000 people who are your customer, each paying you $100 a year, you now have $100,000 a year of passive income.  The point is that you don’t need to serve the entire human population, just enough to have critical mass. 
​Affiliate marketing is the practice of partnering with a company (becoming their affiliate) to receive a commission on a product. This method of generating income works the best for those with blogs and websites. Even then, it takes a long time to build up before it becomes passive. If you want to get started with affiliate marketing check out this great list of affiliate marketing programs.

If you need cash flow, and the dividend doesn’t meet your needs, sell a little appreciated stock. (or keep a CD ladder rolling and leave your stock alone). At the risk of repeating myself, whether you take cash out of your portfolio in the form of “rent”, dividend, interest, cap gain, laddered CD…., etc. The arithmetic doesn’t change. You are still taking cash out of your portfolio. I’m just pointing out that we shouldn’t let the tail wag the dog. IOW, the primary goal is to grow the long term value of your portfolio, after tax. Period. All other goals are secondary.


Role of “real estate professional” can be well played by a non-working or stay-at-home spouse. If you’ve got one who’s willing of course. 🙂 Under current tax law, with a spouse/real estate professional materially participating in the rental property activities, the 3.8% Medicare tax (discussed in Section 1) can be entirely avoided. So, while there is a bit of burden in meeting the requirements, this could be a great play for a Doc and a real estate professional spouse who want to take unlimited real estate losses against regular earned income AND shelter any gains from the additional 3.8% tax.
In most cases, any loss from an activity subject to the at-risk rules is allowed only to the extent of the total amount you have at risk in the activity at the end of the tax year. You are considered at risk in an activity to the extent of cash and the adjusted basis of other property you contributed to the activity and certain amounts borrowed for use in the activity. Any loss that is disallowed because of the at-risk limits is treated as a deduction from the same activity in the next tax year. See Pub. 925 for a discussion of the at-risk rules.
I prefer assets that make me a high return for the lowest amount of work possible (semi-passive involvement). And assets that pay me in several unique ways. Cash flow is only one way RE makes money for me. I also get principal reductions, appreciation, tax advantages (depreciation), and I control the rental increases on a yearly basis. Plus a majority of the capital is provided by the secondary market on 30 year fixed low interest rate debt.
Finance was concerned that notwithstanding protective provisions in the law to safe guard against this tax deferral, professionals and other groups were using corporations exclusively for the purposes of gaining this benefit. This platform of concern for politically correct fairness and equity however did not address the fact that the after-tax profits of a corporation distributed to the individual are subject to a second layer of tax when the individual is paid a dividend from the company. As such, when Ms. Shareholder ultimately receives a dividend from the CCPC of its retained earnings, she will have paid a combined corporate and personal tax of approximately 56%, which is about 3 points higher than the top marginal rate applicable to individuals. The objective of the second layer of tax is to achieve what historically was called the principle of integration.
When I purchase an existing online business, I look for cash flow over the past year and where the money comes from. I want the sources to be more passive so that it does not take a lot of my time. Also, typically I will make an offer that is 18 – 24 months of profit so that I know that I will get my money back within the next two years. I hope that helps!
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