LeBron James and Stephen Curry have a lot in common.

Both multiyear MVPs have annually raked in millions through endorsement deals. Curry's signature line of basketball shoes has impacted Under Armour's sales by an estimated $14 billion, according to an analyst from Morgan Stanley. And last December, James signed a lifetime deal with Nike for $30 million annually. It's the largest single-athlete guarantee for the sportswear giant, and may be worth over $1 billion.

The two differ considerably, however, when it comes to their approaches in personal finance.

Back in 2012, Curry signed a four-year, $44 million contract with the Golden State Warriors for an annual income of roughly $11 million. The deal makes him just the fifth-highest paid player on the team, and it's a reality that Curry is bitterly aware of. "I had to make a conscious decision and remind myself over and over [to let it go]," he told Yahoo Sports. At the time, Curry suffered from ankle injuries that put into question his physical potential on the courts. Rather than waiting to "test out a free agency" in 2013--and possibly reap a maximum offer on the market--Curry played it safe, knowing that the $44 million was more than enough to provide for his family.

"What he did was take what he deemed and perceived to be a very fair and generous deal at the time," says Jeremy Paul, managing director of RLP Wealth Advisors. He argues that Curry's logic can be applied to just about any profession. Paul's wealth management firm frequently works with athletes, entertainers, and entrepreneurs. "While Curry is underpaid now, in retrospect, it allows the Warriors to give other players competitive salaries and build the team in a more competitive way," he said.

By contrast, James has been making big bets on changes in the basketball industry through a series of short-term, opt-out contracts. Currently, his annual salary with the Cavaliers is worth over $23 million. In 2014, the NBA announced a nine-year, $24 billion television deal with Turner Sports and ESPN (which takes effect this summer). By opting out of his two-year contract with the Cavaliers in 2015, and signing another two-year deal at a higher rate (which similarly lets him opt-out after the first year), James can now take advantage of the higher salary caps that will likely come from Turner Sports and ESPN.

"The pool of available money [in the NBA] is going to absolutely balloon over the next few years," said Paul. What James is doing, he explains, shows he wants "the shortest deal possible to capitalize on money that will come the following summers." As a result, it could maximize his salary in the long run.

James and a number of other free agents (like Kevin Durant) stand to make millions more by waiting to hammer out long-term deals. Salary caps are expected to reach $67 million this summer, jumping to $89 million next summer, and $108 million by 2018, sources told ESPN.com.

Compared with Curry's, the four-time MVP's strategy is still a dangerous gamble. If James gets injured, for instance, he risks losing guaranteed income down the line. Of course, with career earnings that reach $600 million to date, and over $48 million from endorsement deals and startup investments, by Forbes' s estimate, he's on solid financial footing.

Nevertheless, analysts suggest that for entrepreneurs, the better strategy is a long-term one. When it comes to NBA contracts, "a school of thought believes the shortest deal is the most attractive because it allows you to remain flexible and competitive," says Paul. "When you have the control and the net worth that LeBron does, it makes sense--but it does come with accompanying risk. In any profession outside of sports, the thought always needs to be 'what is enough,' not 'what is the maximum.' "

For example, when small-business owners (20 percent of RLP's clients), are negotiating a sale with buyers or investors, the firm advises that it's much better to be realistic with a company's current finances, rather than projecting value into the future.

"A large part of the success of entrepreneurs is the passion and the energy they have, but sometimes that interferes with their true understanding and opinion of the business," Paul said. "An entrepreneur has to understand the likelihood of success or failure, and that a value someone is willing to pay for the business might be the right value today."