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Come on, admit it, you place at least one bet each Derby on the name that means something to you. I do. For fun, below is the list of this year’s Derby horses with the investing or financial planning lesson that can be gleaned from their names. (In the order of their Road to the Derby points)

Clients ask us all the time about either keeping a house they used to live in and renting it out or buying a house to rent out. I guess us Americans have some kind of burning desire to control our section of the Monopoly board. Usually I begin my response with a flip answer such as, “A mutual fund won’t ever call you at 3:00 in the morning with a stopped-up toilet.” And, while the hassle of managing rental property can’t be overlooked, let’s concentrate on the numbers of residential real estate as an investment.

Yes, I know, you just filed your taxes and the last thing you want to think about is taxes. I get it. But, what if there were some simple ways of reducing your tax liability and decreasing your chances of owing next April? Interested? Take 90 seconds to skim the following tips:

If you’ve ever read this blog before you know I’m a huge fan of the book, The Millionaire Next Door. Written in the mid ‘90s the authors sought out the rich in the U.S. to learn how they became wealthy. To their surprise, they learned that most were ordinary working professionals who lived beneath their means, saved with a purpose and became wealthy the old-fashioned way: steadily, over many years. Since most of us accumulate our wealth through our 401(k)s or 403(b)s, here are 5 tips to maximize the value of those accounts:

The term “sandwich generation” commonly refers to those people who are caring for aging parents and their children at the same time. Today, I introduce a new term – The Financial Sandwich Generation.

My parents were children of the Great Depression and, like many people of that era, they were and are careful with money. While extraordinarily generous to their children, grandchildren and to their beloved charitable causes, spending money on a luxury just for themselves still requires breaking decades of money muscle memory. Surveys during the 1960s showed that people who were young during the Great Depression were not only, like my parents, extremely careful with money but also quite risk averse. Not surprisingly, this aversion to risk made this generation much less likely to invest in the stock market.

During my regular morning Starbucks visit recently I overheard a conversation between two mothers doing what us parents do – brag about the advanced intellect of their children. In this case, 3-year old “Billy” was off all the charts at pre-school and obviously on the fast track to a Harvard full-ride. I, of course, was intrigued and just had to see what toddler budding brilliance looked like so I inconspicuously glanced over….just in time to see “Billy” lick the display glass in front of the pastries. Maybe Billy’s parents would be wise to invest for his future just in case his genius doesn’t reveal itself to those outside his immediate family.

I have a fond memory of my maternal Grandfather sitting me down before I graduated from college and telling me, “Steve, whatever you do, don’t borrow money.” While Grandpa John lived far from an easy life as a dairy farmer in Nebraska, there was no mortgage on the farm when he inherited it after his father died. Circumstances now, however, are just different and heading into retirement with a mortgage might be perfectly reasonable. Quick rule of thumb: Compare the interest rate on your mortgage with your projected investment returns and allocate your dollars to the higher number.

Last week I wrote about how insurance companies often represent themselves as “financial advisors” while they attempt to sell you complicated insurance contracts called annuities. But they aren’t the only ones hawking these fee-laden products. If your employer’s workplace retirement plan uses TIAA, (like UK, Transy, EKU, etc.) chances are you’re invested in an annuity – even if you didn’t realize you chose it. Why do the firms that sell annuities like them? The money they reap in fees.  

First, what is an annuity? While there are many complicated varieties, the simplest is when you pay a lump sum amount and purchase an insurance contract – called an annuity – that promises to pay you a certain amount for the rest of your life. It sounds great because those of us without a pension have to save, invest and then figure out how to take income from those investments all through our retirement – and that can be tricky. Voila! A perfect solution, right? Well, remember the expression, “If it seems too good to be true, it probably is.”

About once every two weeks or so, on average, my wife will receive a mailer inviting her to a free steak dinner – apparently vegetarians aren’t good prospects – that promises to reveal the secret of not running out of money in her golden years. I used to receive the same ones when I worked at UK, so I assume that’s the list she’s on. As I scan the invitations I often skim to the bottom of the page where the fine print explains these firms don’t really offer investment, estate or tax advice. What do they sell? Insurance contracts called annuities. They imply they’re offering educational retirement planning workshops, but their real intent is to sell expensive annuities and life insurance policies.