Divorce can be a challenging turning point—but for some celebrities, it’s also a launchpad for reinvention. Rather than shrinking into the aftermath, these public figures used their divorce settlements or newfound independence to build businesses, brands, or ventures that resonate—and thrive. Exploring these entrepreneurial rebirths reveals how setbacks can fuel bold new chapters. From fragrance lines to wellness brands, these five icons turned personal transitions into professional triumphs.
1. Lauren Simon Launches a Fragrance Business
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Following her high-profile divorce from property mogul Paul Simon, reality star Lauren Simon chose to channel her independence into creativity. She launched Lauren Stone Collections, a fragrance line born partly from her desire to show her daughters they could make it on their own. The brand became a symbol of self-reliance amid emotional and financial upheaval. What started as personal reclamation evolved into a commercial venture with authentic stakes. It’s a powerful reminder: adversity can spark self-made branding.
2. Christine McGuinness Builds Content on Her Own Terms
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After a costly and emotionally draining divorce, Christina McGuinness reinvented her career via a modern platform. She joined the adult-subscription site Subs.com—an OnlyFans spin-off—to share mini-series exploring motherhood, neurodiversity, and body positivity. The move wasn’t just income: it was an act of autonomy. By producing original content, she reclaimed control over her story and finances. In a way, her new business emerged directly from personal and financial crossroads.
3. Kris Humphries Invests Settlement in Franchises
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Once known primarily for his brief marriage to Kim Kardashian, ex-NBA star Kris Humphries has turned the page with savvy business moves. Post-divorce, he turned his attention to entrepreneurship, opening franchise locations such as Crisp & Green, Five Guys, and Dave’s Hot Chicken in the Midwest. These ventures illustrate how a split didn’t sideline him—it gave him a push into lasting enterprises. His journey shows how leveraging newfound freedom can fuel franchise growth.
4. Trinny Woodall Channels Hardship into Beauty Empire
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British fashion guru Trinny Woodall endured a painful personal chapter amid divorce and her ex-husband’s suicide. But rather than collapse, she built an international beauty brand, Trinny London. Founded in 2017, her company brought in nearly £57 million in sales by March 2024 and is now valued in the hundreds of millions. Her brand became a beacon for empowerment, helping others look—and feel—their best even in the aftermath of trauma. From heartbreak to beauty empire: Trinny rewrote her story through entrepreneurship.
5. Sophia Amoruso’s “Girlboss” Rises After Personal Setbacks
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While not directly tied to divorce settlements, author and entrepreneur Sophia Amoruso demonstrates how personal disruption can ignite business evolution. After the collapse of Nasty Gal and a divorce, she founded Girlboss—a media platform empowering women in business, anchored by her bestselling book and hit Netflix adaptation. She turned recovery into reinvention. Her journey offers a powerful context for understanding how life’s endings can fuel new beginnings—even when not explicitly funded by settlements.
When Divorce Sets the Stage for a Comeback
These stories illuminate how a personal rupture—often painful—can become the fuel for unshakable reinvention. By investing their settlements, voices, and vision into new ventures, these celebrities exemplify resilience. Their paths remind us: when one chapter ends, entrepreneurship can offer a powerful new beginning.
Which celebrity reinvention story inspired you most—and would you launch a business if life gave you a fresh start? Share your thoughts in the comments!
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Amanda Blankenship is the Chief Editor for District Media. She frequently writes for a handful of blogs and loves to share her own personal finance story with others. When she isn’t typing away at her desk, she enjoys spending time with her daughter, son, husband, and dog. During her free time, you’re likely to find her with her nose in a book, hiking, or playing RPG video games.
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