If you can max out your 401k or max out your IRA and then save an additional 20%+ of your after-tax, after-retirement contribution, good things really start to happen. If one is looking for earlier financial independence, such as retiring in their 40s or early 50s, it may be a good idea to skew towards more after-tax savings and investments given one has to wait until 59.5 to withdraw from their 401k or IRA penalty-free.
I am a Certified Financial Planner®¹ and am the founder of Intrepid Wealth Partners. I work with entrepreneurs from startup through exit on financial planning to realize their hopes, dreams & goals. I am an avid world traveler, certified as a Dive Master in SCUBA, have been skydiving, and love meeting new people. Follow us on Facebook, connect with me on LinkedIn.
If you do not meet any of the above criteria and you lose money on a real estate investment, you still may be able to reduce your taxes. First, use a loss on one real estate investment to offset a profit on another investment. If you make $20,000 on one apartment building but lose $3,000 on a duplex, you will end up with only $17,000 in taxable income from real estate activities. If you only own one property, the IRS usually allows you to carry that loss forward to offset profits in the future.
In the Tax Court Case of  Stephen P. Hardy, et ux. v. Commissioner, TC Memo 2017-16.  Dr. Stephen P. Hardy is a plastic surgeon who has specialized in pediatric reconstructive surgery since the early nineties. He conducted his medical practice through Northwest Plastic Surgery Associates, which is a single member PLLC. Mrs. Hardy is the chief operating officer. Previously, Dr. Hardy performed operations either at his office or at two local hospitals.
Low Income Taxpayer Clinics (LITCs) are independent from the IRS. LITCs represent individuals whose income is below a certain level and need to resolve tax problems with the IRS, such as audits, appeals, and tax collection disputes. In addition, clinics can provide information about taxpayer rights and responsibilities in different languages for individuals who speak English as a second language. Services are offered for free or a small fee. To find a clinic near you, visit TaxpayerAdvocate.IRS.gov/LITCmap or see IRS Publication 4134, Low Income Taxpayer Clinic List.
We’ve discussed how to get started building passive income for financial freedom in a previous post. Now I’d like to rank the various passive income streams based on risk, return, and feasibility. The rankings are somewhat subjective, but they are born from my own real life experiences attempting to generate multiple types of passive income sources over the past 16 years.
This shouldn’t be a surprise. I mean, when I speak to groups and ask how many docs in the room would cut their hours/shifts/call etc if their finances allow it and they all raise their hand. So taking a group of docs who not only have their financial ducks in a row, but also have a side income and pursuit already, why would they be working full-time?

It may also be possible to stagger dispositions of investments between calendar years. For example, if there will already be more than $150,000 of AAII in one year, consider triggering additional capital gains in that year, rather than the next, if that might reduce AAII below the threshold in the next year. Conversely, you may wish to trigger capital gains or losses in a specific year because capital losses cannot be carried forward to a future year for purposes of reducing AAII. As a result, you may wish to realize capital losses and gains in the same taxation year.
In fact, as I laid in bed one morning coming up with this post, I could really only think of one aspect of passive income that is worse than earned income. If you are a high earner, you can’t deduct real estate losses against your earned income unless you qualify as a “real estate professional,” which basically means you spend > 750 hours a year doing it. That’s it. The rest of the time, passive beats active.
An Individual Pension Plan (IPP) is a defined benefit pension plan created for one person, rather than a large group of employees. Since the corporation contributes to the IPP and the income earned in the IPP does not belong to the corporation, that income is not AAII. The tax benefits of an IPP need to be offset against the administrative costs, including actuarial costs, to set up and maintain the plan.
Blogging is still going to take work starting out. That path to $5,000 a month didn’t happen overnight but just like real estate development, it build up an asset that now creates constant cash flow whether I work or not. I get over 30,000 visitors a month from Google search rankings, rankings that will continue to send traffic even if I take a little time off.

Which all goes back to my point – since companies change in a lot of unpredictable ways, it makes more sense for passive income to just ride the market by investing in a Total Domestic Stock Market, Total Bond Market, and Total International index funds, with allocations that depend on your goals and time horizon. For income, withdraw 4% or less, depending on what research you believe, and you’ve got a pretty low risk strategy.
Haha, that is too funny. I wanted to make an app back in the day called “MyShares” (You can probably tell how I cam up with the name at the time). The idea was that I would loan out books and DVD’s and then would never get them back. Then I thought, how cool would it be if I could rent those items out and that would motivate people to bring them back. Obviously, books and DVD’s are cheap, so this isn’t the money maker. The idea that would probably make the most money would be things like tools, ATVs, etc.
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