The Wicked Smart Investor's blog

Back to school shoppers will soon be out in force looking for bargains as September approaches. With many options, including online sales, getting bargains on clothing, shoes and supplies is easy. When investing your hard earned money, things get a lot trickier.

The outgoing governor, international press, and local mucky-mucks all sat silently as the historical time capsule was opened at the Museum of Fine Arts. Originally placed in a cornerstone of the Massachusetts statehouse by our forefathers, the contents could provide more clues to our colonial past. The crowd was transfixed, what was in the box? The possibilities seemed endless that January, 2015 night

Bostonians are frequently razzed not only for our accents but our lingo as well. Words like packie, spuckie and tonic cause puzzled looks from visitors. In the summer, another local word takes prominence: Jimmies. For those of you that don’t know, “Jimmies” is Beantown’s name for chocolate sprinkles, the bits of candy topping on ice cream cones for added texture. I actually thought all locals use this word, but my research proved otherwise.

I wonder if former State Senator Jarrett Barrios ever admitted he overreacted to his son’s request for a fluffernutter sandwich? While most parents would have just said no, Barrios proposed some “anti-fluff” legislation in 2006. The resulting public outcry was equally overblown. Callers to talk radio shows complained of a totalitarian regime dictating our food choices. Bostonians love fluff and we will be damned if some Haavaad do-gooder is going to take it from us.

It’s normal to feel vulnerable when hiring an investment advisor. You may get a nagging feeling you’re not getting good advice. This pain is easy to avoid; hire someone who acts like a cover band and borrows heavily from the masters.

Retirement planning is so complex it’s tempting to use a product that implies simplification. Target date funds are one example. But there are things in life that should be highly suited to your personal preferences, like your financial plan or your wedding dress.

Jack Frost nipping at your nose should remind us Bostonians that we could get walloped with a snowstorm at any time. A financial storm may come with less notice, so this winter investors should prepare for both.

I get treated like Ebenezer Scrooge at holiday time. After all, there is no investment advisor in Boston’s Enchanted Village. But rather than admonish my readers to rein in spending, I’m recommending you treat yourself this season.

I’ve always wanted to dispel the common investment myth that wealthy people have an automatic advantage in the stock market. So, I thought joining a Boston Brahmin social club would be the best way to explore this topic. Things did not turn out the way I expected, but the process reinforced some very basic life lessons along with investing realities.

I’m not afraid of the creepy clowns running around this year. If you really want to scare the Wicked Smart Investor on Halloween just come to my door dressed as procrastination. This horror show makes me jump right out of my skin. Okay, maybe it’s not Old Granary Burial Ground at midnight with ground fog and howling coyotes kind of scared, but the procrastination ghoul will certainly elicit blood curdling screams out of me! To be on the safe side, I’ll hang some garlic cloves on the front door before trick or treating starts.

Here are the reasons I find procrastination so scary:

Boston’s South Shore is home to two varieties of money mysteries. There’s a big, almost unsolvable whodunit. Then there are thousands of smaller cliffhangers easily solved if the gumshoes kept the legwork simple.

Diners in Boston’s beloved North End are almost guaranteed a great meal. There are so many places to choose from and the competition among restaurants is fierce. If a chef doesn’t make mouth-watering entrees, customers can easily flock to the highly rated place next door. This sets the culinary bar astronomically high. While you can only choose one restaurant for a meal, the abundance of choice reduces the risk your palate will be disappointed.

I’ve always wondered how Sir Isaac Newton, one of the smartest men that ever lived, lost a fortune in the stock market. I went back to school early this year and found out.

Industries have a life cycle just like humans . Like a person’s childhood, teenage years, adulthood and golden years, industries have distinct life stages. A local example is the Nantucket whaling industry. Let’s review the lifecycle.

1659: Nantucket settled.

1752: Start up stage. Whaling voyages begin. The market for clean burning whale oil is small but growing. Industry profits are negative and large amounts of capital are required to build ships and train mariners.

Paragon Park had a gaudy fortune telling machine in its arcade. It was called Grandma’s Prophesies and it looked like a heavily made up corpse laid out in an upright casket. But deposit fifty cents though and good old grandma sprung to life. Light bulb eyeballs lit up, the creaky head spun, and her fiberglass hands moved over a glowing crystal ball. The mystical music added to the experience along with the scents of fresh cotton candy and the Nantasket sea breeze. When grandma finished with her plexi glass enclosed gyrations, a fortune card was dispensed.

The doorbell has an eerie echo tonight, as if it’s vocalizing your disdain for what is happening next. After years of procrastination you finally decided to meet with a financial planner. Retirement is on the horizon and you need to make the most of your savings.

Most people struggle to pick a career. It’s considered a stroke of good luck if someone finds their vocation, a job that they truly enjoy. I do consider myself a lucky man, but I wouldn’t exactly say the leprechauns were looking out for me the day I started on my career path. I’m also not sure that I found financial planning. Maybe it found me.