While today's top country singers can potentially make more money than ever before, that doesn't automatically mean they're going to be set for life. Taste of Country recently talked to two experts in investment strategy about the importance of musicians receiving proper financial advice and planning for their financial future.

We've all seen the hard luck stories about singers who were big stars just a few years ago who somehow wind up penniless after a series of setbacks. We've even seen a number of artists who still have recognizable names declare bankruptcy, sometimes even repeatedly, in order to try to manage debts that exceed their incomes.

Drew Hawkins is the managing director and head of Morgan Stanley Global Sports & Entertainment, and Sara Qazi is a sports and entertainment director and financial advisor there. Hawkins began the special division four years ago in response to what he perceived as a growing need for asset management for celebrities, and it has grown to manage more than $35 billion and employ more than 90 directors around the country.

Hawkins says one reason celebrities can find themselves in financial trouble is that many of them come from backgrounds where they did not have access to money and learn about how to manage finances.

"We all go to school, we all have different majors, but one of the things we very seldom have classes about is how to manage our finances," Hawkins observes. "How to understand our credit score, how to manage a checkbook. How to put together a legitimate budget based on where you are. In creating this division, one of the things we wanted to really focus on was financial education, being able to give folks in the entertainment and sports world a lot more information to empower themselves to make better decisions around what they're doing."

Artists are often times "all really smart, all really talented, but just have not had the opportunity or exposure to be around this particular subject area," he adds.

Sometimes the job consists of rescuing a client from a financial problem, but the goal is to work with them to avoid that in the first place.

"I like to work with a client very early in their financial life," Qazi tells Taste of Country. "Typically they're just beginning to earn money as a live artist or a songwriter, and at that point we get a chance to really deep dive into what their vision is for their life, and then how we can make all that happen for them."

Country Singers Who Went Broke

Lorrie Morgan is one example of an artist who has declared bankruptcy more than once over the years, and she says not taking a more active role in her financial life was "the biggest mistake of my life."

"Be careful and watch your money. Make it, put it away and save it," she advises, "because just as quick as you go up, you come back down."

Longevity is the greatest challenge for clients in the music business, Qazi tells us, as well as a shifting income picture as revenue streams continue to change.

"You've had drastic changes to the industry over the past few years," Hawkins points out. "CD sales are a non-factor now. We went from downloads to streaming, and the importance of people being out there on tour now because that's the bulk of their revenue." That forces financial planners to try to create strategies to smooth out some of the somewhat unpredictable highs and lows and try to create a more predictable steady income through investments.

As simple as it sounds, a lot of the early conversation needs to be about realistic budgeting, focusing on the part of the income cycle when acts are not on the road and earning active revenue and having to rely more on the passive income of royalty streams. A large part of the initial job is psychological and emotional, simply gaining the trust of a star who might be wary of trusting an outsider with their money.

"Money can create a lot of vulnerability," Qazi says. "There's a tremendous psychology around what money means to you, and most of that was formed in your very early years. So part of being an adviser is being a psychologist, helping them get into a safe space with you so that you are able to guide them appropriately. "

Summer is a time when musicians have an exceptional opportunity to maximize revenue with touring and especially lucrative festival appearances, but the money from festivals, for instance, often doesn't pay out until months later. Hawkins and Qazi emphasize the importance of working in lock step with an artist's entire team of managers and advisers to create a plan that best maximizes that revenue when it does come in, looking ahead to a day when any given artist might suffer a career downturn and need long-term strategies to survive.

Country artists have been changing the way they look at the playing field in more recent years, increasingly turning to non-musical ways to monetize their recognizable brands. Witness Taylor Swift, who used a career in country as the springboard for a vast empire of endorsements and opportunities. Toby Keith has amassed a half-billion-dollar fortune through a record label, a chain of restaurants, his own line of Mezcal and more, while name-brand artists including Kenny Chesney, Blake Shelton, Florida Georgia Line, Little Big Town and more have turned to entrepreneurial enterprises to help ensure a larger, steadier income. Forbes' annual list of the highest paid singers in country music reveals an array of income sources that include not only touring income, but also television, product endorsements and, in the case of Dolly Parton, a theme park, while direct music sales play a significantly diminished role in recent years.

While country music has expanded its marketplace recognition more and more to the mainstream over the last 15 years, there's still one area where it lags behind almost all other genres.

"Country music, by and large, doesn't benefit from synchronization licensing incomes," Qazi points out. "Pop, urban and rock do, but synch licensing from an income standpoint is virtually nonexistent in country. That's a huge multi-billion-dollar industry at this point, and country music is by and large left out."

That's all the more reason for artists to plan, invest and save for a rainy day that may be coming sooner than they would like to think.