Financial guru Dave Ramsey is no stranger to getting asked for advice. In fact, people call into his popular show all the time to ask him what they should do to make the most of their money. However, a caller got some seemingly counterintuitive advice during a recent call when Ramsey suggested he leave his career behind to pursue something else entirely.
And while Ramsey’s advice does make sense, it was a shock to hear him tell his caller to turn against a sure thing.
The Family Business Dilemma That Stumped Dave Ramsey
If you’re not familiar with the format of The Dave Ramsey Show, the 65-year-old tends to spend part of the segment doling out financial advice to callers with money questions. In a recent episode, Ramsey was called by a man who wanted career advice after he had started a lucrative side hustle that seemed ready to outearn his full-time job. The only wrinkle was that his full-time gig was with the family business, which added a layer of complication, since he was eager to leave his job to pursue his passion.
“So I’m wondering if I should quit working for my family business and work on my side business that I had started to get out of debt,” the caller asked, noting that he was making between $10,000 and $12,000 in profit each month.
However, the caller noted that he was only making about $90,000 a year through the family business. And while the math was clearly working out in favor of the side hustle for both the caller and Ramsey, one question really seemed to muddy the waters for the financial guru.
“What are the relational repercussions when you quit the family [business],” he asked, prompting the caller to say that he was afraid he’d be cut out of the family entirely, after the same thing happened to his brother when he struck out on his own.
In the end, Ramsey suggested that the caller start a conversation with his family, giving them plenty of advance notice and looping them into the planning so they could collaborate on an exit strategy.
His Followers Had a Lot of Thoughts — and Some Had a Better Idea
While the decision to collaborate on an exit strategy seemed like a reasonable solution, many of Ramsey’s followers were surprised to see how the financial expert handled the situation, especially since he told the caller to leave behind an established company in favor of something new.
“I can’t believe they aren’t telling him to stay at the family company, that’s a stable business, and keep doing the side business, hire employees to run it, keep both,” one person wrote.
Related: Dave Ramsey Tells Caller To Stop Using His Program And Do This Instead
Another suggested that the caller could have the best of both worlds by hiring someone to run the side hustle, allowing him to profit from that business while enjoying the relative safety and stability of his existing career.
In the end, it seems the caller will have a conversation with his family about leaving the business, giving them enough advance notice so they don’t feel left hanging out to dry. Hopefully, this ends up working in the caller’s favor, since it sounds like this side hustle is poised to become a very profitable career for him—as long as he feels like he has his family’s support to make the leap.
Disclaimer: This article is for informational purposes only and does not constitute financial advice.
This story was originally published by Parade on Jun 8, 2026, where it first appeared in the Life section. Add Parade as a Preferred Source by clicking here.
