Money is a complicated thing, both practically and psychologically. It can be a ticket to freedom or a dark presence leading people on a path to destruction, and it’s always a fussy child that needs to be watched carefully and nurtured.

It is an especially thorny topic in the world of entertainment, where money can arrive suddenly and leave just as quickly if not handled properly. That’s why so many actors, musicians, directors and others employ business managers.

To their clients, business managers can be seen as magicians, trusted consiglieres or scolding parental figures. For their part, business managers have to deal with an array of personalities with varying career scenarios that can be tricky to navigate. Nonetheless, there are ways to foster financial health of clients across the board.

Athletes are an especially tricky group to advise. Ask almost any business manager who the most challenging clients are and they’ll tell you that it’s professional athletes. By the time they go pro, athletes are long accustomed to being treated like celebrities in their community, but typically have no experience in dealing with money. The problem is exacerbated by the fact that their careers tend to be short and can be ended at any moment by a catastrophic injury.

Athlete clients often “grew up poor and didn’t go through the normal stages like an actor or writer does, waiting tables,” says New York-based business manager Evan Bell, managing partner of Bell and Co. “They went from the training table in high school to training table in college to the NBA or an NFL career.”

Bell says they often suffer from what he calls “big shot-ism.” Once an athlete signs a big pro contract and the money starts pouring in, they not only buy themselves a big house, fancy car and jewelry, they fund luxurious lifestyles for friends and family and, worse yet, listen to their investment advice.

“The problem is when somebody gets in their ear who doesn’t have the experience and isn’t looking out for the client’s best interest but that emotional connection to them,” says Bell.

Another difficult category is the profligate spender. Clients can bleed out financially with multiple small to medium-sized streams of financial indulgences, or they can wipe out large chunks of their fortunes in one fell swoop by purchasing a big-ticket item like a yacht or a private jet, which have both high price tags and astronomical maintenance costs.

“If you’re someone like Johnny Depp or whatever, and you can have a $50 million Gulfstream and still have hundreds of millions of dollars, I guess it doesn’t matter, but for most people, it’s not worth it,” says business manager Layth Carlson, a partner and Callas & Carlson. “Just to keep the plane parked at Van Nuys airport can cost a million a year, whether you run it or not. You’ve got FAA checks, you’ve got insurance. It’s unbelievable.”

In some circles, private islands have overtaken private jets as the ultimate status symbol. The island that Phil Sarna’s client wanted to buy had no electricity or running water, which meant it would require generators to provide electricity, fuel to power the generators and a place to store the fuel, along with a salt-water desalination system, a boat to ferry people and supplies, and a full-time staff to service everything.

“It was a beautiful island, but it would have been a disaster because just to get infrastructure it would have made this $10 million island a $20 million purchase,” says Sarna, founder of PS Business Management. “And that’s assuming you would have been able to build a house on it that was sustainable and worth visiting more than a few times a year.”

And then there are the gamblers. The classic bad celebrity investment is a restaurant, which appeals to the ego as a physical manifestation of success, where the owner can commandeer the best table in the house and entertain friends and family while press and public are kept at bay by staff and security on the other side of the velvet ropes. But according to the National Restaurant Assn., 60% of all eateries fail in their first year of opening, 80% fail within five years.

“It’s not for the faint of heart,” says Matthew Burke, managing partner of Singer Burke. “It generally takes three times as long as one might think to build a business, it costs three times as much and you make a third of what you think you’re going to make, at least starting out. It’s hard to implement the checks and balances and internal controls in a business or where there’s a lot of cash or a lot of personnel turnover.”

And then there’s crypto. In fact, cryptocurrency had overtaken restaurants as the risky investment of choice in recent years, but a crash in the market last year, spurred by the collapse of terraUSD and the bankruptcy of FTX, which had been promoted with celebrity endorsements from everyone from quarterback Tom Brady to “Curb Your Enthusiasm” star Larry David, has given business managers more leverage to steer clients away.

“Some people got in and out at the right time, but it didn’t make a tremendous amount of sense to me and I’m glad it’s no longer really part of the discussion,” says Mark Cattalini of Level Four Business Management.

On the flip side of the coin stand those clients determined to steer clear of any and all financial pitfalls. Call them the risk-averse. “Those are called good clients,” says Sarna. “I’ve never had a client that’s too conservative.”

Fiscally conservative clients span the generations, from boomers to Gen Zers. “As you get older, you take on less risk because you need to be able to plan your monthly spending and what you are bringing in with each month with a high degree of probability, so that is understandable,” says David Garelick, president of Global Business Management. “But some of the younger clients were around in 2008 and 2009 when we had the Great Recession, and they can be skeptical of the markets.”

But fear of risk can become a negative for clients overly cautious during their peak earning years. “That scenario is when your career is ahead of you and you’re earning enough to maintain your lifestyle, but your asset base needs to be growing for you to support your retirement,” says Bell. “We have clients who grew up poor who sometimes don’t even want to invest in the stock market. It’s all bonds. They’re just afraid to lose it all.”

Another category can be called builders. These are the types who are likely to exhibit good fiscal habits, such as producers. “Producers that are running their own production companies tend to be very focused and savvy when it comes to return on investment in terms of every dollar they put into their company or their project slate,” says Burke. “And those are very interesting and exciting clients to work with because they understand the whole gamut.

They’ve got staff, they’ve got employees, they’ve got HR and other issues to deal with in terms of financial planning and budgeting, not just for their show or their project, but for their company.”

For all these categories, the business manager is an educator, often teaching fiscal literacy to clients who are new to wealth and, according to Elizabeth Campos, director of business management for Manhattan West, the process starts with establishing a trust with her clients built upon honesty and transparency.

“My job is to discipline them and to educate them and to show them the consequences or maybe the rewards,” says Campos. “It’s really worked in my favor because when everyone is going to my clients with these amazing investments, they know to come to me first so we can do our due diligence and make sure it checks all the boxes, instead of impulsively entering into the investment based just on positive buzz.”

The key lesson clients need to learn is what constitutes an acceptable risk proportional to their wealth. For instance, if a client is worth $100 million, buying a $5 million house is fine, but they should think twice if they’re only worth $10 million. Also, putting money in crypto or another bleeding edge investment might not be such a bad idea, provided it’s a small portion of their overall portfolio.

“Clients are always ahead of the game when it comes to new technology and seeing the future way more than the rest of us mortals,” says Sarna. “But there has to be a balance in terms of risk and timeline and liquidity.”