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The Guys’ Guy’s Guide to Things Worth Investing In


They call it disposable income for a reason. We dispose of it every day—at lunch on $12 salads in plastic containers, ironic t-shirts, another pair of sneakers or shoes we don’t need to choke our closet space, or on numerous $9 glasses of so-called craft beers. But even though we live in a consumer society where over two-thirds of the money spent is on items we don’t really need, there are a few items worth paying those extra dollars for. Large or small, these are classic items worth the money, so your Guy’s Guy is going to lay them out for you to chew on and digest. Here in no particular order, is my GUYS’ GUY’S GUIDE TO THINGS WORTH INVESTING IN.

1. Real estate – The rent really is too damn high. And besides getting a roof over your head for the next thirty days, there is not much to get excited about when renting your home. From my personal experience, I’ve done relatively well when investing in real estate and it began as soon as I found a way to scrape together the down payment to afford a mortgage for a modest, man-cave studio and the responsibilities that came with it. And I have never looked back. When you own that roof over your head, you get a tax break on the mortgage interest, you live in your investment, and in the vast majority of cases your home appreciates while you’re there. Wherever you may be, but particularly when you live in a ridiculously expensive city like New York, if you can find a way to buy your home, do it. If you can make those monthly payments, in the long run it will serve you well, amigo. Very well. Ask anyone who has done so and they will have a story to tell you about how much profit they made after buying that once-cheap co-op back in the eighties.

2. A great watch – Every Guy’s Guy needs at least one piece of top-notch jewelry. If he’s married he’s going to want a quality wedding band, but regardless of his marital status, this Guy’s Guy believes that owning a classic watch is a worthwhile investment. Let’s face it. There are clocks everywhere and you carry a phone so you don’t need a watch to know the time. A watch is a statement piece for a Guy’s Guy.  It’s something you can wear every day or if you choose, just to events that you hold in importance. I sat in the office next to the director of the Mont Blanc account at a big ad firm. I gave him a few bottles of rum since I ran the Bacardi account and he let me to pick from the Mont Blanc catalogue at half price. I was making good money so I bought very high-end “sport” watch, a silver dress watch, a pen, and a wicked cool pair of shades. I still have them all and I wear the two watches frequently to this day. On my fortieth, my folks bought me an engraved Rolex, so of course I also wear that too. But besides also owning a handful of very affordable watches, I’m done buying watches. The watches I own are statement pieces so I don’t need a special box or case filled a dozen good watches. I have three great watches, and that’s all I need. I still like admiring the classic timepieces I see, but I’m done.

3. A well-tailored suit and a tuxedo – A Guy’s Guy knows how to clean up, so every Guy’s Guy needs to own at least one finely tailored suit, regardless of his job or the type of work he does. There will always be an occasion where he needs to get decked out and show his stuff, so it’s a good idea to invest in a tropical wool designer suit in navy, charcoal or black. If you shop at an outlet you can pick a very nice suit for less than five hundred bucks. I recently purchased a classic, yet modern Theory suit that fits me like a glove for less than less four hundred that was originally priced at $1200. And, I will wear it when I need to for the next decade because it’s quality, a classic yet modern cut, and I work hard staying in fighting shape, like Guys’ Guys tend to do.

Another consideration is investing in a classic black tuxedo. I recent attended a wedding where the young guys in the wedding party wore maroon tuxedo jackets with black shirts and pants.  Not my style, but it was is their business. The point is; no one buys a maroon tuxedo jacket. I bought a well-made black tuxedo when I was in my twenties, and it still fits me and looks good. I also bought a formal white dress short shirt, cuff links, and a pair of shoes I only wear with the tux. Buying a tux is not as mission critical as owning a well-tailored suit, but it can be a good investment, especially if you compare it to the cost of renting.

4. A quality automobile – I’m still working on a personal issue that I have about letting go of things and people. This time it got me in trouble. I bought a silver Toyota Four-Runner in 2000 and due to my moving back into NYC, I rarely drove it. I kept it parked it on the street near the beach in New Jersey, and over the years the engine and the parts underneath the vehicle began rusting, and rusting, and rusting. I need car when I’m in Jersey and this vehicle was fully paid for, so I kept it but was making repairs and replacing rusting parts repeatedly. The decay continued and eventually, my prized vehicle became an albatross. I eventually dumped it, but not before I wasted a shitload of money on repairs.

I did buy a good vehicle, and that is part of the lesson because owning or leasing a good car can be a good investment, but only if you know when to cut bait and move on. Buying a car is so 1990 these days, so now I recommend leasing a top of the line vehicle and switching it out every few years. If you live in the burbs and show up for a date in an old rattlebox, it means negative points with the new lady.

5. Going to the dentist – A Guy’s Guy needs a first class ride for his teeth. A man’s oral health is a gateway to his overall health. And who doesn’t want a great smile? A Guy’s Guy looks for a dental practice with skilled hygienist and a dentist that can handle drillings and replacing old fillings to get that toxic metal out of your mouth, and doing what’s necessary to brighten your smile. Most healthcare plans these days scrimp on dental so having a great dentist might get expensive at times, but think about it as a sound investment in your overall health. Studies have found that built up plaque can find its way to your heart and other areas of your body and create havoc.

6. Wedding ring and band – EarlierI briefly mentioned thiskey, hopefully one-time purchase as anotherstatement piece for a Guy’s Guy. When you marry, you want to show pride and your commitment. There is no better way to make your wife feel good about it than investing in a classy wedding rings and bands for both of you, but in particular for her. Make sure you exceed her expectations, and if you can swing it, go for at least two carats. No matter who pays for your band, pick a ring that looks masculine and makes you feel good about yourself. Trust me on this, amigos. It’s worth the investment to the marriage. And do you best to wear your wedding band. I’m not a big ring guy, but I keep mine in a little box on my bureau and at a bare minimum wear my platinum gold band when I am out in public with my wife. It’s the right thing to do.

7. Wine and spirits – Many Guys’ Guys like a cocktail or a glass of wine or beer now and then. Over time, most guys have had their fill of keggers and shots of lousy booze. When you finally grow out of that stuff, drink the best that you can afford, especially if you are drinking infrequently or drinking your booze straight. So out with the speed rack brands and on to the top shelf brands. As you age, if you still drink alcohol, drink less and drink better. Fear not, it’s not going to break the bank. There are many good vodkas available for $20 bucks and rums for between  $20 and $30. You’ have to pay more for good tequila, bourbon or scotch. When drinking wine, you can usually find something for every day drinking between $20- 35.  And if money is an object, with a little research you can find a decent bottle for less than $20. Beer is all about personal preference regardless of price. The point is that the clock keeps ticking and you’re not going to live forever. Opt for the good stuff when you drink.

8. Organic food – It costs more, but you are protecting your health by eating organic food. The processed packaged crap down the aisles in the supermarket may taste good, but it isn’t good for you, and non-organic produce and fruit has been sprayed with pesticides. Over time, eating this stuff can cause chronic health issues. Think of yourself as a sleek Mercedes-Benz 450SEL. To keep it running smoothly you don’t fill it with the cheapest fuel. And despite all the cute memes you read about bacon, it’s basically processed pork, and that is not good fuel for a luxury vehicle like you.

9. Your wallet – This might seem like a minor thing, but think of how many times you pull out your wallet every day. A good wallet sends the right psychological signals to your brain about your financial self-worth and to others as to how you value yourself and your money. Spend a few extra bucks and buy a good wallet. It will help you feel your best about your financial standing even in tough times. Stay classy, amigo.

10. The right relationship – Investing the time in finding and securing the right life partner is probably the best investment you will ever make. I stayed single for so long that close friends and family stopped asking me when I was getting married. I knew I was not ready, so I waited until I had the epiphany of making room in my heart for someone else before taking the plunge. Maybe it took me longer than most. That’s my business, but I’m glad I waited, and I am glad I made the right investment in the right woman for me.

I hope these tips help you make sound decisions about the things in life that are worth investing in. I’m sure I missed a few along the way, but this is a good start for any Guy’s Guy who wants to send out signals that say, “Hey, I’m a Guy’s Guy and this is how I roll.”

This week’s GUY’S GUY OF THE WEEK is the actor and classic Guy’s Guy, Cary Grant. Although he may have swung ways, no worries and no judgments. He still was a Guy’s Guy. Despite his living in a different time, this guy was all class. Although I’m not sure how he invested in real estate, he died a rich man and oozed timeless style when he was alive. If you are ever in doubt about spending those extra dollars on any of the items I mentioned, ask yourself what would Cary Grant do and you can’t go wrong.