Real Estate Investing Basics

Ending Your Real Estate Career

155 Articles Written
real estate retirement

There seems to be no shortage of articles on how to start investing in real estate or taking your business to the next level. What you don’t often see is a post on how to wind down your career. To someone just starting out this may be something they aren’t worried about. But they should be. Just as you want to have an exit strategy for a particular investment property, you should have one for your investing career as well.

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Last week I was having lunch with several seasoned real estate investors. One of them broached the subject of packing it in. Though he had made a lot of money, the fire in the belly had gone out. It was time to move on to something else in life. Sounds simple, but is it?

A Myriad of Complications

This investor had a few problems to deal with. He had successfully laddered a number of properties as buy and hold investor. When the value of a property had increased sufficiently, he would refinance and use the proceeds to buy more property. It was always done with an eye on cash flow, if the rental income couldn’t service the debt and expenses he wouldn’t refinance. Cash flow wasn’t the concern, equity was. He wasn’t upside down on the mortgages but he was on the income taxes. Huh?

The double-edged sword of depreciation had reared its ugly head. Investors often tout the tax benefit of being able to take a depreciation write off to reduce income taxes. That’s all well and good – until it’s time to sell. This investor has owned a number of properties for a long time. That means the cost basis for capital gains has been greatly reduced and there is the seldom-talked about issue of recapture. You know all of those lovely depreciation deductions? Well the IRS wants them back. That is why they call it “recapture,” the IRS is going to recapture those deductions when you sell. The problem for this investor is that when liquidating many of his properties he would have to put money in to cover taxes. That’s a downside of pulling out equity along the way.

One Solution

Many of you are saying, “just do a 1031 exchange to defer the taxes.” While that is a solution, this investor wants to move on from real estate. After several decades of investing he wants to do other things with his life. His biggest complaint is that he didn’t plan for this sooner. He is working with his accountant and attorney on a liquidation plan. It won’t happen overnight. He figures it will take three to five years to accomplish, if not longer.

So what’s the plan? The easy part is to simply liquidate the properties that don’t have a tax problem. For the ones that do this investor is exploring the use of a Charitable Remainder Trust. Wealthy people that have stock portfolios that have appreciated significantly frequently use this. It can also be used for real estate to minimize taxes. In simple terms, a charitable trust is set up and highly appreciated and/or depreciated assets are “gifted” to the charity via the trust. The property can then be sold tax-free and the proceeds reinvested in income producing instruments. The grantor (person who set up the trust) receives the income but the assets of the trust given to the charity upon death of the grantor.

There are certainly drawbacks to this plan. Not the least of which being loss of access to the principal. To this investor that isn’t an issue. When that is an issue other avenues need to be pursued. The main point here is that your business plan needs to include an exit strategy. You do have a business plan, right?

Begin with the end in mind.Stephen R. Covey (The 7 Habits of Highly Effective People)


    Chris Somers
    Replied over 9 years ago
    Great point in that folks need to have an exit plan for real estate as well and is not discussed too much. It can be complicated but in some cases it can be quite simple. Sometimes it makes sense to just get liquid and deal with the tax man accordingly. Too often (especially in the stock market) when investors make decisions based solely on tax consequences, it can end up being a bad decision down the road.
    Rachel Aka Mobile Home Gurl
    Replied over 9 years ago
    Great post, Richard. You’ve made a lot of good points. I’ve known of investors in the same exact situation as the one you describe. Sometimes things sound simple but when it comes down to it, there’s more involved. I think you nailed it with Steven Covey’s quote to “Begin with the end in mind.” If folks can see the end, then they’ll know where they need to go. Thanks for sharing!
    Jeff Brown
    Replied over 9 years ago
    Richard — So easily avoided. Been preachin’ about having a Plan and doing things on Purpose for decades. This is an excellent example of the potential consequences of success without a professionally structured plan. Great stuff.
    Replied over 9 years ago
    I think the “retiring” form real estate investing is what scares me the most. I am nowhere near the “end” yet, but with everything to consider and the real esate market flucuations I must admit the end is not as far off as I would like it to be. To stressful and not enough gurantee for me anymore. Great post I will deifnitly keep these things in mind and bookmark in hopes I can build a great exit stratagy.
    Replied over 9 years ago
    My exit plan is to die and let me children inherit my real estate through a family partnership. If the property is generating income why sell it?
    Replied about 9 years ago
    Very nice article Richard, and very nicely put. We definitely need to think about an exit strategy first and there are many investors out there who rush into something without thinking it through and end up stuck or loose profit.