When Colin from Arizona called into The Ramsey Show, he was facing a dilemma that many Canadian entrepreneurs eventually encounter: Whether to stay in a profitable business he helped build or walk away entirely.
Colin earns about C$700,000 annually from a company generating roughly C$4 million in revenue. Despite the healthy income, his mental and emotional well-being has deteriorated. As he explained, his relationship with his co-owners has unravelled.
“There are no regular meetings, no formal policies and very little collaboration between owners,” Colin said. “Most decisions are made on a gentleman’s agreement. When I raise concerns, I’m told, ‘Don’t rock the boat.’”
The lack of structure, combined with what Colin describes as persistent disrespect from his partners, has made him question whether the financial benefits are worth the toll. While his only major debt is a US$480,000 mortgage — which he could pay off if the other owners buy out his shares — Colin is wrestling with whether leaving would be the right move.
Dave Ramsey seems to agree that getting out is the best move.
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Ramsey’s Two Reasons to Get Out Now
For Ramsey, Colin’s dilemma comes down to two factors: personal well-being and business viability. And on both counts, the verdict is clear — it’s time to walk away.
1. He’s miserable — and that’s reason enough
Colin’s declining mental and emotional health alone is sufficient justification for leaving.
“You’re miserable and you’re done,” Ramsey said.
Toxic work environments can lead to burnout, stress and a poor quality of life. Even a half-million-dollar paycheque can’t offset the personal costs of staying in a situation that’s draining and unsustainable.
2. The business model is destined to fail
Beyond Colin’s personal well-being, Ramsey warns of deeper structural issues.
“The misbehavior of the business operations are going to cause the failure of the business,” he cautioned. “You’re going to ride the horse till it dies — and it’s going to die.”
The absence of structured policies, regular meetings and collaborative decision-making points to serious operational dysfunction. Colin’s experience of being disrespected by his partners is likely a symptom of a broader cultural problem that will eventually affect employees, vendors and customers.
“You cannot be under the illusion that this is a perpetual $500,000-a-year income,” Ramsey said. “It is not.”
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How Canadians can protect themselves in a buyout
Walking away from a profitable venture isn’t easy — especially when personal assets, like your home, are on the line. Before signing a buyout agreement, Canadian experts recommend three key steps:
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Hire a business lawyer: A buyout agreement is complex and high risk. According to RBC, an experienced Canadian business lawyer can protect your financial interests, ensure your ownership stake is properly valued and flag unfavourable terms. Without proper legal guidance, you risk walking away with far less than you deserve.
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Get an independent valuation: Never rely on your partners’ assessment of the company’s worth. A neutral, third-party valuation expert can determine a fair market value for your shares and protect you against undervaluation — a critical step if your personal finances depend on the payout.
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Plan your next move: A buyout isn’t just an exit — it’s a chance to reset. Use this transition to pay off personal debts, like your mortgage, and free up resources to explore new ventures or investments.
The takeaway for Canadians
Colin’s situation underscores a broader truth: financial success without sound leadership rarely lasts. A high paycheque loses its value when the business model is shaky — or when staying comes at the cost of your health, physically or mentally.
Ramsey’s advice is blunt but pragmatic: Exit now, secure your buyout while the company is still healthy and protect your future before deeper cracks emerge.
“As we say in Tennessee,” Ramsey concluded, “get out while the getting’s good.”
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Sources
1. The Ramsey Show Highlights: How Do You Know When It’s Time To Leave A $500,000 A Year Job? (Aug 16, 2025)
2. RBC Wealth Management: The Unsung Hero of Business Succession: A Deeper Look at Buy-Sell Agreements, by Riley Otto (May 5, 2025)
3. BDC: What’s your business worth? (Oct 4, 2022)
3. Bakertilly: Post-sale: What comes next?, by Tom Hamilton-Piercy (Dec 18, 2023)
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.