Buying and selling stocks, for the wise investor, can be an easy way to make money multiply. But the wise investor knows that it's not as simple as day-to-day or week-to-week gambling. You might hit a homerun on a stock that soars twenty percent in a month and, knowing the volatility of the market, want to sell it before its price starts dropping.


Congratulations, you've just made a twenty percent return on your investment. Why are the wise investors laughing, then?

You hear a murmur among the laughter: "capital gains tax." The word "tax" drops like a weight in your stomach. Yes, a tax on your winnings. They are, after all, a form of income.

What is capital gains tax and how can you reduce it?

What is capital gains tax and how does a wise investor factor into into their investing strategy?

The simple answer is that they make long-term investments. We all want to materialize our gains quickly but doing so can hurt them more than you might expect.

Short-term capital gains tax affects short-term investments—buying a stock and selling it within one year. The important word here is "selling": you only realize a gain or a loss when you sell the stock. Therefore, capital gains tax only comes into play when you sell a winning stock (capital gains tax affects all kinds of "capital assets").

The short-term capital gains tax rates (investments held for at least one year and one day) are significantly higher than the long-term. Short-term rates equal the normal income tax rate. The rates depend on your tax bracket, but at every level, the long-term rate is lower than the short-term rate.

Those in the 10% and 15% income tax brackets will face 10% and 15% short-term capital gains taxes, but 0% long-term rates. In the higher brackets, though both rates increase, investors will still save 10% or more by holding stocks for more than a year.

The simple solution, therefore, is to invest with long-term goals in mind.

An investor who needs to sell a stock before a year is up can try to offset some of the gains by also selling a stock or stocks suffering losses. Capital gains tax only affects the net capital gain for the year: this is the total gains after all sales.

If you sell one stock at a $2,000 gain and another at a $1,000 loss, you'll cut your net gains in half and reduce the amount on which you can be taxed. It sounds like simply losing money in a different way, and it is. But it eliminates part of a loss on stock while reducing the tax at the same time, minimizing the overall loss.

The bottom line is that you'll have to pay up somehow. Maximizing returns involves more than simply finding the golden stock. The wise investor understands the differences between short-term and long-term investing, factors capital gains tax into their plan and, when circumstances call for a short-term sale, uses a strategy that realizes other losses to offset the gains and reduce the taxable amount.

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I thought I had a pretty good handle on my finances out of school. I worked several jobs while attending university and had little to no problem managing my income. However, once I graduated, I realized how much more complicated personal accounting could really be.

There were so many variables I needed to keep track of. Biweekly bills, monthly charges, and general necessities amounted to a heap of confusing numbers that were often impossible to decipher. The funniest part was that I was actually trying to do this by hand (I don't know what I was trying to prove to myself, either).

After messing up for the 17th time, I decided to give Microsoft Excel a shot. I used Excel a bit in school and I knew all the big-wig finance people used it, so what could I possibly have to lose? The answer is about six hours of my precious time. Excel isn't much of an improvement over handwriting and it's still dependent on the user to manually input all of the information. It's like doing everything by hand with the slightest help, meaning that it still required a tremendous amount of time and concentration. Well that was all for nothing, I guess.

It's sort of funny. I was certain that I could manage my personal finances with ease, when it's practically a full-time job. I was already stressed out enough with my first job and I knew I didn't have enough time to give my finances the attention it deserved.

That's why I decided to try out a budgeting app. My best friend told me that he uses an app called Truebill to manage his finances. "What does it even mean to manage your finances?" I asked him. He told me that Truebill was the personal financial assistant I wished I could have. It could aggregate all of my account information into one place and give me specific insights and actions.

I loved the idea of having full control over my finances, especially during a time of financial uncertainty, and I realized that Truebill would be the easiest way to accomplish this. The user interface is incredibly simple and intuitive, so it doesn't even feel like a finance app! Truebill offers a multitude of features, with their most popular being the ability to cancel subscriptions with the press of a button.

Okay, I had no idea how many subscriptions I was still subscribed to. In fact, I wasn't even using a quarter of the subscription services I was signed up for. Subscription boxes, streaming services, my old gym, and even an old subscription to my favorite magazine--it was all there and I was livid. How could I let myself waste all of this money and how did I never catch this? Thank goodness for Truebill.

Truebill also offers bill negotiations. There is a 40% fee based on how much you save and Truebill even claims that there is an 85% chance that they'll be able to lower your bill once a negotiation is requested. Why wouldn't I take them up on this? There was zero risk and I would only have to pay once my bill was lowered (which means that I would be saving money regardless).

More standard features of Truebill include the ability to generate a credit report on-demand and even request a pay advance. I only used the pay advance feature once when I wanted to buy a gift for my mom, but didn't have enough cash in hand and Truebill automatically reimbursed itself when I got my next paycheck.

The credit report is another fantastic feature and practically taught me what good credit meant. Truebill's credit report basically shows you which financial decisions have the most significant impact on your credit score and ways that you can improve your credit month-over-month. I've never had such control over my credit and it feels good.

I'll be the first to admit that I was extremely naive coming out of school. I figured that as long as I was attentive, I could manage my finances with ease. We manage money to some extent throughout our entire lives, but once you're thrown out on your own, it's a completely different story. With Truebill, I've finally been able to take control over my finances and stay on top of all of my responsibilities.

Update: Our friends at Truebill are extending a special offer to our readers! Follow this link to sign-up for Truebill.