How to Money Ask HTM - Combatting Healthcare Premium Hikes, Purchasing Long Term Disability, and WTD with Nine-Figure Wealth #1090
Jan 19, 2026
This episode dives into a range of fascinating listener questions. After a company sale of $300 million, they discuss how to structure your newly acquired wealth. Rising healthcare costs are tackled with insights on health sharing plans and comparing market options. The hosts also debate the merits of holding rental properties in LLCs to protect assets. Finally, they explore the importance of long-term disability insurance, outlining what to check in your policy and when it truly makes sense to invest.
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Protect Cash With FDIC Distribution
- Do protect large cash balances using programs that disperse funds across many banks to remain FDIC insured.
- Do research CDARS-style services (one statement, multiple banks) to avoid uninsured bank exposure.
Use Buckets For Liquidity And Growth
- Do split money into buckets: a few years of cash, long-term growth investments, and a separate bucket for big goals or philanthropy.
- Do keep a short-term cash reserve to avoid selling investments during market dips for planned purchases.
Plan Life Design, Not Just Finances
- Consider how your days and identity will change after exiting a business instead of just the finances.
- Replacing work with projects like real estate or part-time ventures can prevent post-exit emptiness.