200. “Should we pay off our massive debt? Or invest more?”


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Mar 18 2025 100 mins   734

Wilson (46) and Shannon (35) have built a strong financial foundation—owning a vacation rental, maxing out Roth IRAs, and earning solid incomes. But when it comes to their next move, they’re at odds.

Wilson wants to tap into their home equity to invest in stocks, believing they’re too heavily weighted in real estate. Shannon, more risk-averse, worries about adding debt when they already owe $129K on their home, plus tax and student loans.

Can they align on a strategy that balances security with growth?

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