10 Times Quitting Was the Best Financial Move People Ever Made

Sometimes walking away from a steady paycheck leads to the biggest financial gains. These real stories prove that quitting isn’t always about giving up, but choosing growth over comfort.

1. The Murray Brothers Traded Suits for Swimsuits

Brothers Shep and Ian Murray were miserable sitting behind desks at their corporate jobs in Manhattan. So in 1998, Shep Murray, an advertising account executive, and Ian Murray, who worked at a small public relations firm, quit their jobs within 10 minutes of each other. They maxed out credit cards to start Vineyard Vines, selling ties out of backpacks on Martha’s Vineyard beaches. The company is projecting about $100 million in sales for 2011.

2. Sara Blakely Left Door-to-Door Sales Behind

After failing the LSAT twice, self-made billionaire Sara Blakely sold fax machines door-to-door for seven years. She quit to pursue her idea for better women’s undergarments with $5,000 in savings. In 2012, she became the world’s youngest self-made billionaire. Her company, Spanx, is now worth over $1 billion.

3. Rick Wetzel and Bill Phelps Walked Away from Nestlé

Rick Wetzel and Bill Phelps were working for Nestlé when the concept for Wetzel’s Pretzels was born. They developed their business plan on a bar napkin during a work trip. About a year later, Wetzel and Phelps got their lucky break when they were offered a severance package from Nestlé. Their pretzel franchise now has 250 locations with system-wide sales exceeding $100 million.

4. Terry Finley Left Insurance for Horses

Terry Finley was finishing his military service in 1990 when he and his wife, Debbie, bought a $5,000 horse. After their horse won its first race, Finley quit his insurance job to start West Point Thoroughbreds. Since 2007, its horses have won more than 20 percent of their races, with purses totaling more than $16 million and counting. Annual sales are near $7 million.

5. Restaurant Workers Created Terra Chips

Dana Sinkler and Alex Dzieduszycki were working for star chef Jean-Georges Vongerichten at his four-star restaurant, Lafayette, in New York, when they decided to strike out on their own and start a catering business. They experimented with frying vegetable roots in Sinkler’s tiny apartment kitchen. At the time, Dzieduszycki says, Terra Chips had $23 million in annual sales when they sold to Hain Celestial in an $80 million deal.

Read More: 15 Careers That Are Booming Right Now (And How to Get Into Them)

6. Adam Lowry and Eric Ryan Left Corporate to Clean Up

Adam Lowry was working as a climate scientist, and Eric Ryan was in advertising when they decided to leave their jobs to develop the environmentally friendly cleaning product company, Method. They maxed out credit cards and raised $200,000 from family to start their eco-friendly cleaning products. Method has become one of the fastest-growing private companies in America, with over 100 products and gross revenue of $100 million.

Read More: The 10 Worst Ways to Ask for a Raise (And What Actually Works)

7. Rod Johnstone Sailed Away from Sales

Rod Johnstone was 38 years old and working as an ad salesman for a boating publication when he decided to design his dream sailboat. He built his first boat in his garage with lumber donated by his parents. Since then, J/Boats has built more than 13,000 boats, from small crafts to yachts, bringing in millions of dollars in revenue.

8. Andy Schamisso Found Tea Gold

In 2002, Andy Schamisso was working in public relations but wasn’t satisfied. When his wife couldn’t find rare white tea for her iced tea recipe, he discovered a business opportunity. So after 13 years in public relations, Schamisso quit his job to start Inko’s White Tea. The company now generates $3 million in annual sales with 14 varieties on the market.

9. Fashion Workers Shot to Success

Kim and Beaver Raymond both said, “I quit” after a homemade toy they dreamed up for their son turned into a big hit. The Raymonds were working in the fashion industry in 2002 when they made marshmallow “shooters” out of PVC pipe for their son’s birthday party. Their Marshmallow Fun Company sold more than $7 million worth of shooters in 2010.

10. Rocky Patel Left Law for Cigars

Rocky Patel was a Hollywood entertainment lawyer when he developed a passion for cigars. Despite colleagues’ warnings against leaving his lucrative practice, he quit to manufacture cigars in 1996. Rocky Patel Cigars now produces 20,000,000 cigars annually and had sales in excess of $40 million in 2011.

The Pattern Behind Success

These stories share common threads that separate smart quitters from reckless ones. Most started their ventures as side projects while still employed, testing market demand before making the full leap.

The successful quitters also had financial cushions or clear monetization paths. They didn’t just abandon a steady income on hopes and dreams; they identified genuine market opportunities and had specific plans to capitalize on them.

Most importantly, they quit toward something better, not just away from something bad. Their dissatisfaction became fuel for building solutions others would pay for.

Read More: 10 Tiny Career Changes That Can Add Six Figures to Your Lifetime Earnings

About the Writer

Ellen Allen

Ellen Allen is an East Coast writer who brings a personal touch to finance and career topics, drawing from her own experiences to offer relatable, real-world advice. She believes the best insights come from lived moments, helping readers navigate money and work with confidence and clarity.

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