How to Save Taxes and Avoid the Five Deadliest Retirement Killers

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One of my favorite topics is financial and retirement planning.

Regardless of where you’ve heard it, it seems that most experts agree that the majority of us have about 40 productive years in life before we start to approach retirement. As Ed Slott, PBS presenter and author of “How to Parlay your IRA into a Family Fortune,” says, it’s hard for the average person to figure out the Retirement Puzzle. Many of us have enough trouble making money, let alone saving money, investing money, keeping and protecting money, and a few even have problems giving money away, like the Warren Buffets’ and the Bill Gates’ of the world.

But as Ed points out, you need to have a plan, and you need to begin with the end in mind. He goes on to talk about the Silent Retirement Killers:

  1. Taxes
  2. Risk
  3. Saving Money
  4. Uncertainty
  5. Inactivity

Although this may be hard for some of you to believe, the good news is that these are all under our control.

The Largest Expense: Taxes

First, let’s take a look at our number one expense: Taxes. We should all try to move our money from forever taxed accounts to never taxed accounts.  Two of the best ways to do this is with IRA accounts and life insurance.

Take the Roth IRA—it may make more sense to convert your IRA to a Roth right now.  Pay the tax now.  It may be better to pay tax on the seed instead of on the crop.  If you’re like me, you believe taxes today are probably lower than they will be in the future.  Plus, I would rather pay the tax on a lower balance today, than a larger one in the future.  Besides, once you’re in a Roth, you can’t be forced to withdraw your money from the account—normally you’re required to withdraw starting at age 70 ½ in traditional IRA and 401(k) types of accounts.

Life insurance, on the other hand, is much safer than a bank, as there’s no interest income tax, and money can pass favorably to heirs.  Insurance policies are also protected from creditors and lawsuits, even bankruptcy, similar to retirement accounts.  If you have a good advisor, who represents a reputable company, it can also make a lot of sense to convert taxed accounts into policies that can grow tax-free.

One of the best wealth building strategies for me was saving taxes over the years, thus creating money to invest, and I saved the tax money by utilizing depreciation from all my real estate holdings to offset my earned income. Also, being a real estate professional at the same time was huge.  Most folks are capped at $25,000 in losses, but mine were unlimited. There were years that I had negative income, yet had millions of dollars in assets.

Another strategy that friends of mine, who were wholesalers and flippers, utilized was they used their Roth IRAs to purchase a real estate brokerage.  How cool is that?  I did something similar on a business level, where we employed three strategies into one plan.  We utilized a retirement plan, in this case an ESOT–Employee Stock Ownership Trust, that owns our servicing company, and we use this in conjunction with key man life insurance to almost completely eliminate taxes, utilize asset protection, encourage employee retention, create a business bank, and set up succession and Legacy planning.

See Diagram:


There are some rules, for example: you need at least 11 full-time, non-family member employees, and you also need an ERISA attorney, as well as a business planner. But, this Tax Efficiency Strategy can be a huge win for everyone including government, employees, and donors.

Dealing with Risk

Now, let’s look at Risk. The two biggest risks are future taxes and stock market fluctuations. Remember before, I said these are in your control?  Here’s an example of how you can completely eliminate risk and taxes: have an annuity inside your Roth IRA.  Annuities are one of the safest, insured investment vehicles on earth, and they can also be guaranteed for life.  When inside your Roth IRA, you will never be forced to take out payments or even pay taxes on earnings or payments.  How cool (and simple) is that?  Now, I’m not saying you should do this with all of your money or that it produces the highest yield, I’m just trying to show what a good company and advisor can do for you with the right strategy.

Another retirement risk is Saving Money, or should I say, saving money in the wrong places.  Sometimes the best moves require you to spend money, for example with the Roth IRA or insurance policy.  Maybe it’s better to pay the taxes now, rather than later.  We also need to be careful of free advice, as it may end up being the most expensive.  I’ve always preferred advisors, who are fee-based, and some are becoming much more affordable today, especially online (Check out “Financially Fearless,” by Alexa Von Tobel, owner of LearnVest).

More Retirement Killers

The last two retirement killers are Uncertainty and Inactivity.  Uncertainty will guarantee failure by doing nothing. I understand that a common concern becomes “Who do I believe?” At the end of the day, though, you have to trust yourself because it is your money. On the other hand, inactivity is probably the most deadly retirement killer. The average financial planner may tell you that having no plan means conceding to the government’s plan, and many people believe that if they wait long enough, something bad will happen to them. But, when it comes to retirement planning, I agree with what John L. Beckley (author, businessman, and founder of Economics Press, Inc.) wrote: “most people don’t plan to fail, they fail to plan.”  After my father retired from a very good job with a sizable retirement account, the market crashed, and he had to go back to work in his mid-70s.  Pop never knew much about retirement planning, and he didn’t read books like “Missed Fortune 101,” by Doug Andrew, either.

So, if you really want a stress-free retirement, like I do, consider cash flowing assets with collateral, such as real estate and/or notes. For me, at my age, there’s nothing like a performing note that I bought at a discount, which already has a steady stream of high yielding payments, requiring little or no work (thanks to my servicer), and is still backed by a nice piece of real estate. Happy Investing!

About Author

Dave Van Horn

Since 2007, Dave Van Horn has served as president and CEO of PPR The Note Co., a holding company that manages several funds that buy, sell, and hold residential mortgages nationwide. Dave’s expertise is derived from over 30 years of residential and commercial real estate experience as a licensed Realtor, a real estate investor, and a fundraiser. As the latter, Dave has raised over $100 million in both notes and commercial real estate. In addition to his investments and role as CEO, Dave’s biggest passion is to teach others how to share, build, and preserve wealth. He authored Real Estate Note Investing, an introduction to the note investing business, helping investors enter the “other side” of the real estate business.


  1. Brandon –

    I’ll have to disagree, or at least caution you against, Roth IRAs/401k’s as a blanket “better choice”. I’ve done an extensive write-up that I won’t repeat here, but the short of it is that if you aren’t taxed on the ‘seed’ money, you have more money growing concurrently than you would have if you took post-tax money and put it in the IRA.

    Furthermore, if you intend to scale down your expenses or your lifestyle during retirement, you’ll likely fall into a lower income bracket and therefor be subject to reduced taxes even if overall taxation goes up. Just keep in mind your desired lifestyle and the fact that you can use the government’s tax dollars to grow your nest egg before jumping into a Roth. The whole write-up, including math, can be found here:

    • Hi Ryan,
      I agree that it’s not a blanket better choice; I should have included a disclaimer to this regard. It is a case to case basis. Which one would be better mathematically may depend on the individual’s expectations for success in the future.

    • Every person has to evaluate their own situation and goals so I won’t in anyway dispute that there can be good reasons to go Traditional Vs. Roth.

      One thing that has never made sense to me is this stuff about scaling back in retirement. I guess if your goal is string out a crappy existence bring bored and unfulfilled as long as possible that makes sense. Personally I’d want to take life up a notch when I don’t have any commitments anymore.

      • Hi Shaun, I agree–not everyone has the same outlook on retirement. Personally, I wouldn’t want to scale back in retirement either. Thanks for sharing your perspective.

  2. Hey Dave! I’ve been reading your articles for a while, and subscribe to your newsletter as well over on PPR. I’m a little confused. You say,

    ” requiring little or no work (thanks to my servicer)”

    So is PPR a servicer, or do you only sell/broker the notes? It sounds like the latter. If that’s the case, do you mind sharing who your servicer is?

    I understand PPR can train folks to service their notes, but what if we just want someone else to do it? Thanks!

    • Hi Sharon,
      Thanks for reading the articles! In the section you mentioned, I was referring to my performing notes that are placed with a servicer. PPR owns all of its own notes—we don’t broker. There are multiple servicing companies out there that will work notes for you. PPR uses FCI Lender Services, Inc.
      I hope some of this helps!

  3. Great article. Lots of good point to consider when planning for your future.
    I like the ideas and strategies put out there.

    I love the the idea of buying a business like a brokerage in an IRA. That is a way to invest in real estate in an IRA that would never have occurred to me.

    • Hi Shaun, thanks for the positive feedback! Most people don’t think about buying a business in their IRA. I heard Mitt Romney made a killing by buying a start-up with his Roth. Another strategy is investing in your vendors. For example, when I renovated houses, I owned the drywall and painting company that did the rehabs. When I sold houses, I owned the title company as well.

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