Photo by Anna Webber/Getty Images for SiriusXM
The one thing money can’t buy for this couple.
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A successful entrepreneur from St. Louis recently called into Dave Ramsey’s EntreLeadership podcast with an unusual problem. Scott has been working from home for 20 years, running a treadmill operator web business that brings in between $150,000 and $200,000 annually in nearly pure profit. Despite this impressive income, his wife of 26 years wants him to get what she calls a “real job.”
The couple, who have three children together, also co-own a retail store that generates $1 million in revenue but only yields about $50,000 in profit. Scott’s wife also works as a full-time teacher, which provides the family with health insurance and a valuable $20,000 annual discount on private school tuition for their children.
When Scott explained his situation during the podcast call, Dave Ramsey’s response was immediate and direct. “You getting a real job is a ridiculous, insulting statement,” Ramsey said. “You have a real job. You just happen to be self-employed, and you make a lot more money than she makes with her two things combined.”
Dave Ramsey offers clear direction for the stressed couple
The core issue, according to Scott, is that his wife feels overwhelmed by their various business ventures and believes “something needs to change.” She expressed that they are “too busy” and “stressed out” by having multiple income streams and business decisions to manage. The couple finds themselves constantly discussing business matters, even during dinner.
Ramsey provided the couple with two clear options to resolve their dilemma. The first option involves Scott’s wife continuing her teaching career to maintain the health insurance benefits and tuition discount, while they sell the retail store. The second option would require her to quit teaching, purchase private health insurance, and fully commit to growing the retail store into a more profitable venture.
Understanding what it takes to build substantial wealth often requires making difficult choices between different business opportunities. Ramsey stressed that if they choose to keep the retail store, earning only $50,000 profit on $1 million in revenue is unacceptable.
The retail store employs about 20 part-time workers and has a loyal customer base, making it essentially run on autopilot. However, Scott’s wife, who is listed as the company president, bears the mental burden of final decision-making and ownership responsibilities.
Ramsey’s advice focused on the importance of making a definitive choice rather than trying to maintain multiple ventures that create ongoing stress. He suggested the couple envision their lives 10 years from now and decide whether Scott’s wife wants to retire as a teacher or as the owner of a thriving retail business.
The situation highlights a common challenge in entrepreneurial families where traditional employment is often viewed as more secure than self-employment. Many content creators have built substantial fortunes working from home, yet these non-traditional careers still face skepticism from those who equate “real jobs” with traditional office environments.
Research shows that self-employment can actually provide more job security than traditional employment in many cases. Entrepreneurs with diversified income streams, like Scott’s combination of online and retail businesses, often have more financial stability than employees who depend on a single employer. Building multiple revenue streams has become a popular strategy for achieving financial independence.
The story resonates with many modern families where one spouse pursues entrepreneurship while the other maintains traditional employment for benefits and stability. Even wealthy celebrities face criticism when their approach to money doesn’t align with public expectations. Understanding these dynamics can help couples make informed decisions about their financial future and work arrangements.
Published: Aug 16, 2025 10:31 pm