Nicholas Riccio is a name that has begun to attract more public attention, largely because of his marriage to Karoline Leavitt, the White House Press Secretary. But behind the headlines and the political spotlight lies a compelling life story—one that moves from hardship and adversity toward ambition, transformation, and quiet influence. In this article, we’ll trace how Riccio built a real estate empire, how he navigates his public role in the shadows, and what lessons his journey can offer.
Early Life and Struggles
Nicholas Riccio was born in Hudson, New Hampshire, to Marilyn and Anthony Riccio, and grew up as one of four children. His parents divorced when he was still young, and the family faced financial difficulties as they moved around and struggled with limited resources.
As he entered adulthood, life became even tougher. By his late teens, Riccio found himself homeless—living out of his car or relying on friends for a place to shower or rest. He later described times when, at age 19 or 20, he would call a buddy to hang out just so he could use their shower.
Despite those hardships, Riccio was determined. He worked modest jobs (such as stocking supermarket shelves) to earn money, all while attending Plymouth State University. Financial insecurity persisted—there were nights when he slept in his car to keep tuition paid.
What stands out in his early life is that Riccio’s ambition and resilience were tested early. Many would surrender under such burdens; he chose to use every obstacle as fuel. The struggle shaped not only his character but also his later approach to business and risk.
The Turning Point: Real Estate and Vision
Nicholas Riccio path changed direction in 1990, when he decided to take a real estate course that would become pivotal. That decision opened his eyes to how property, when viewed through a lens of renovation and community revival, could become both meaningful and profitable.
One memorable moment came during a drive with his mother along Hampton Beach’s M Street area. The neighborhood was dilapidated—many buildings were condemned, others in serious disrepair. To many, it was an eyesore. To Riccio, it was full of possibility.
He started small. The first building he bought on M Street was a stretch—he did not have much capital—and some of his early purchases were financed through loans or support from friends. But he kept going. Over a dozen years, he acquired 15 buildings in that area, housing around 70 housing units, and gradually transformed M Street into a revived neighborhood.
His approach was methodical: careful renovations, clean and modern interiors, and a focus on converting neglected real estate into desirable rentals or properties.Local officials took notice: Hampton’s police chief praised his work in improving the area and making it more welcoming for families.
This period of concentrated effort and investment laid the foundation for what would grow into Riccio Enterprises LLC and ancillary ventures.Over time, Riccio expanded beyond just M Street, owning properties across New Hampshire—from Boston suburbs to the White Mountains.
In many ways, that transition—from seeing decay to seeing opportunity—is the key turning point in his life. He transformed his eye for potential into a sustainable business model.
Building the Empire: Riccio Enterprises and Property Holdings
By the early 2000s, Riccio had become a prominent figure in the Hampton Beach real estate scene. He formalized his operations under Riccio Enterprises LLC, offering long-term rentals, vacation properties, and renovation projects. He also launched a related brand, Nautical Beach Properties, which markets vacation homes in coastal areas.
As his portfolio grew, so did the prices and prestige associated with his properties. For example, in 2025, nightly rates for a one-bedroom unit at 14 M Street were listed at around $259, while a four-bedroom house on 16 M Street could fetch $469–$619 per night. These rates reflect both the quality of his renovations and the desirability of his locations.
Estimates of Riccio’s net worth vary considerably. Some reports place him near $6 million, while others go as high as $45 million.The wide range is likely due to the private nature of many of his ventures and the volatility in real estate valuations.
Riccio’s portfolio is not solely about profit, though. He has sought to bring positive change to communities—revitalizing neighborhoods once ignored, and turning decaying buildings into livable, attractive spaces. In doing so, he has earned local recognition and what some call “local legend” status in parts of New Hampshire.
Yet, even as the business grew, Riccio seemed to avoid the limelight. He maintained a low public profile, avoided heavy social media presence, and preferred to let his work speak for itself. That reserved posture perhaps helps him balance the demands of business and family life, especially now in the public eye.
Personal Life, Marriage, and Public Exposure
For a long time, Riccio kept his personal life out of the spotlight. But public interest grew sharply when he married Karoline Leavitt, who in 2025 became the youngest-ever White House Press Secretary.
Leavitt and Riccio first met in 2022, during Leavitt’s congressional campaign in New Hampshire. They were introduced at an event hosted by a mutual friend at a restaurant owned by Riccio. Over time, friendship turned into romance.
One of the more talked-about aspects of their relationship is the 32-year age gap—Riccio was about 59 years old, while Leavitt was 27 at the time of their marriage.When asked about it, Leavitt described their love story as “atypical,” but praised Riccio as “incredible,” supportive, and her “rock.”
The couple welcomed their first child, Nicholas Robert “Niko” Riccio, in July 2024. Three days after Niko’s birth, a serious event occurred: an assassination attempt on President Trump, which forced Leavitt to curtail her maternity leave and return to work.
Leavitt has publicly discussed her husband’s personality and preferences. She said Riccio is introverted (the “complete opposite” of her own more outgoing nature) and largely avoids social media, choosing to stay out of public self-promotion. She has also noted that Riccio’s business flexibility allows him to follow their family’s movements, which is especially helpful given her frequent travel and demanding role.
Despite the scrutiny their relationship has drawn, the two seem to present a united front. Critics have not been shy—comments have ranged from mocking the age gap to more cynical labels. But Leavitt has defended Riccio sharply: “He’s my number one fan, the best dad, and just the best man I’ve ever met.”
The dynamic of their relationship raises interesting questions about public perception, generational differences, and how two people with different worldviews can (or cannot) balance partnership, career, and identity.
Challenges, Criticisms, and Risk
Like any public figure who rises from modest means to success, Riccio’s journey has faced questions, setbacks, and controversies.
One challenge is the vagueness around his net worth. The huge discrepancy in reported figures (from $6 million to $45 million) invites skepticism and uncertainty. Also, much of his portfolio is private, making verification difficult.
Another incident of note: in 2023, one of his older rental cottages along M Street went up in flames, suffering both fire and water damage. While disasters happen, they can damage reputation, insurance costs, and community trust—especially in a region where his properties are highly visible.
Criticism also comes from public opinion, largely around his marriage. Some social media users have made harsh or mocking comments about the age gap, using derisive nicknames or insinuating motivations like financial gain. Balancing a public life with harsh scrutiny is no small feat.
Furthermore, as an introvert with minimal public exposure, Riccio faces the difficulty of maintaining privacy while being connected to a high-visibility spouse. Leavitt’s role in the Trump administration and national media attention place him in a spotlight he might prefer to avoid—and that mismatch can create stress.
Finally, real estate is inherently risky: market fluctuations, maintenance burdens, regulatory pressures, and economic cycles all threaten even well-managed portfolios. Riccio’s past success doesn’t guarantee immunity. How he navigates downturns will test his resilience and adaptability.
Lessons and Legacy
Even with remaining unknowns, Nicholas Riccio’s story offers valuable lessons for entrepreneurs, dreamers, and people striving to break out of difficult circumstances.
1. Vision matters more than capital (early on).
Riccio didn’t start wealthy. He saw potential where others saw decay. That vision allowed him to make early moves in undervalued properties—moves that later paid dividends.
2. Incremental progress compounds.
He didn’t leap into big deals overnight. His approach was gradual: one building at a time, renovations, gaining trust, reinvesting profits. Over time, that compounding effect created a meaningful empire.
3. Resilience under adversity is foundational.
His period of homelessness, financial struggle, and lack of support could have derailed him. Instead, those hardships seem to have forged mental toughness and a mindset framed around “making do” and pushing forward.
4. Low profile, high impact.
Riccio’s preference for privacy and limited social media presence shows that not every high-achiever seeks the spotlight. His impact is in buildings, neighborhoods, and infrastructure—not in personal branding. That humility may be an asset in enduring scrutiny.
5. Relationships and balance matter.
His marriage to Karoline Leavitt shows how personal life can intersect with public life. Their differences—age, personality, role—make balance a challenge. But they also highlight that successful partnerships often require mutual support, flexibility, and respect.
As for legacy, only time will tell whether Riccio becomes more of a public figure or remains a behind-the-scenes influencer. But already, he has reshaped parts of Hampton Beach, created a lasting brand in New Hampshire real estate, and shown that a compelling underdog story can morph into a meaningful modern career.
