Karoline Leavitt's Husband Was Reportedly 'Homeless' Before They Got Hitched

Karoline Leavitt and husband Nicholas Riccio's lavish lives show they aren't exactly hurting for money. For starters, Leavitt gets a hefty payday as President Donald Trump's press secretary. Riccio also makes a pretty penny thanks to his successful career as a real estate developer in New Hampshire. However, the road to financial stability was bumpy, with Riccio being homeless in his younger years. Through a series of bold — and risky — moves, Riccio managed to break into the real estate industry and make bank.

Now, Riccio is estimated to be worth $6 million. In fact, sneaky signs suggest Leavitt's husband might be richer than we thought, considering he once sat down with George W. Bush to ask for tips about buying a sports team. Leavitt, who is worth an estimated $7 million, believes their matching fortunes contribute to their marital happiness. "He's built a very successful business himself, so now he's fully supportive of me building my success in my career," he said on "The Megyn Kelly Show" in February.

Even though Leavitt and Riccio may have a massive 32-year age gap, their goals are clearly in sync. However, they couldn't have had more different upbringings. Leavitt grew up a tight-knit family that ran an ice cream shop in Atkinson, New Hampshire, and older brothers who loved her fiercely. Riccio, on the other hand, had none of her idyllic childhood. On the contrary, Leavitt's husband comes from a tragic background. His younger years were tough, but they prepared Riccio to face life's adversities head-on. 

Nicholas Riccio's parents divorced when he was little, paving the way for an unstable and often turbulent childhood. He grew up poor and bouncing from place to place, never living somewhere long enough to have a sense of home. But that figurative feeling became literal after he graduated high school in 1983 and found himself with no roof over his head. "When I was 19 or 20, I would call my buddies to go over their houses to watch a game just so I could take a shower," he told Seacoastonline in 2005.

Despite his difficult situation, Riccio was determined to go to college and fulfill his mother's hopes that he would get further in life than she ever could. He found a job to cover his tuition at Plymouth State University, but his wages weren't enough to cover rent too. So he lived out of his car. Unfortunately, a college degree didn't guarantee him a high-paying job. Instead, he found a job stacking shelves at a grocery store. While he did that, he decided to take a real estate course. He fell in love with property development, but he needed money to do that.

He started borrowing money at crazy interest rates, a decision that could have put him in an even more dire financial situation. But it paid off. He now owns 10 properties, nine in New Hampshire and one in West Virginia, ranging in cost from $5,500 to $400,000, according to Realtor.