Jan 29, 2026
Chris, 37, quit his day job as an engineer because while it made him money — enough to purchase “the biggest house I could buy” — it also made him miserable.
But as the Denver resident shared on The Ramsey Show, he soon realized that buying a $650,000 home with 3% down and private mortgage insurance and then quitting his job were two big “financial mistakes” (1).
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Then there was his next decision: sinking $100,000 in renos into the home to turn it into an Airbnb.
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He thought “house hacking” would make the math work. It didn’t, leaving him $10,000 in the hole in the second year — even though he was living with friends, babysitting their kids in return for housing.
“You've made a mess, and so you've got to get the shovel out,” Dave Ramsey agreed. “The barn is full of poop.”
Both Ramsey and his co-host Jade Warshaw said Chris should sell the house and get a day job. Neither option appeals to him. Here’s why he may have to bite the bullet anyway.
Ramsey reality check
To date, Chris has invested $750,000 in his home ($650,000 plus $100,000 in renovations).
Unfortunately, Zillow and Redfin estimates suggest his home is worth far less — somewhere between $580,000 to $615,000. So he’s reluctant to sell.
“I think I might be falling into a sunk-cost fallacy,” he admitted, referring to the reluctance to abandon something you’ve invested heavily in, even if it’s a lost cause.
Still, with just $10,000 in total savings to his name and no paycheck, Chris doesn’t have the flexibility to wait out the market or absorb losses. So the Ramsey Show hosts encouraged him to cut his losses and sell, despite his reluctance.
As to getting a day job, Chris is equally reluctant.
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“I’m not suited for a nine-to-five job,” Chris told Warshaw and Ramsey, saying that he thought being an entrepreneur was a better fit for him.
Ramsey wasn’t having it, suggesting that “not suited” meant “not preferred,” a distinction he doesn’t have time for when people are in debt and need a paycheck.
“First thing you’re suited to is to pay for food, lights and water,” he said. “Second is to pay your stinking bills. And the third thing is to find something that is a style of work you enjoy.”
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Reactive fixes vs. financial stability
Research shows that when people are experiencing financial scarcity, it can impact their decision-making abilities (2).
A lack of liquidity is a major reason why reactive decisions, like Chris’s move to launch an Airbnb venture, can backfire.
Airbnbs are marketed as an easy income stream (3), but the reality is you need a steady stream of guests and must invest in ongoing maintenance.
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Chris’s story is a reminder that having a solid financial foundation matters before becoming an entrepreneur.
That’s why the CFP Board, which sets standards for certified financial planners, stresses that sustainable wealth-building starts with financial stability, including having an emergency fund (4).
For anyone navigating a similar situation, the lesson is simple: Fix the foundation before chasing profits.
You don’t want to be in a circumstance like Chris where, as Ramsey said, “The mathematics around it don't math.”
Article sources
We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.
The Ramsey Show (1); Leiden Univesity (2) Business Insider (3); CFP (4)
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Freelance writer with an economic development and consulting background.
