Cuban first met Tiffany the gym in 1997. He was 39 and had already launched Broadcast.com, which Yahoo would acquire in 1999 for $5.7 billion. Tiffany was a 27-year-old advertising executive.
Early on in their relationship, Cuban said he considered any speculation about marriage "a no-win question for me," according to Forbes.
Source: Bustle
And, while they were still dating, Tiffany told The New York Times that adjusting to life with the billionaire required "great patience."
Source: The New York Times
During their courtship, she continued to drive her Honda to her advertising job, and wasn't a fan of their "impractical" chateau.
Source: The New York Times
The couple also suffered from "scheduling problems," according to The New York Times, owing to the billionaire's penchant for dividing his day into "blocks of seconds" and staying up on his computer late into the night. At the time, Tiffany said, "I always know I'm not going to be No. 1. He can't turn it off. He just can't."
Source: The New York Times
Still, the couple found a way to make it work, and wed on a beach in Barbados in 2002. The event was low key and intimate, with only 20 close friends and family in attendance.
Source: ESPN, The Dallas Morning News
Initially, Cuban and Tiffany had their sights set on Jamaica, but Hurricane Isadore forced them to switch islands. However, in an email to The Associated Press, Cuban said the couple was "having a blast on our honeymoon."
Source: ESPN, The Dallas Morning News
Cuban and Tiffany now have three children. At South by Southwest, the billionaire said he and his wife stress the importance of hard work: "They can't be Mark Cuban's or Tiffany Cuban's son or daughter. They have to be adults and they have to carry their own weight."
Source: Business Insider
Tiffany told DFW Child that she tries to keep her kids "out of the public eye as much as possible." Despite her husband's busy schedule, she said the family finds time for low-key rituals, like Saturday morning breakfasts at a diner and plenty of downtime.
But Cuban has joked that his political ambitions might prove to be a snag in the marriage. The entrepreneur told New York Times columnist Andrew Sorkin that when he brings up running in 2020, Tiffany always has the same response: "She asked me if I want to stay married."
Source: Fortune, Business Insider
