All the Hacks: Money, Points & Life 10 Lessons That Challenged My Thinking on Money and Life
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Nov 5, 2025 
Tad Fallows, co-founder of Long Angle and former iLab Solutions co-founder, shares insights from a retreat for high-net-worth investors. He emphasizes that health is the most vital asset, advocating for personal health advocacy and smart fitness investments like trainers. The conversation also explores building meaningful relationships through intentional interactions and travel. Tad discusses the importance of 'lighthouse parenting,' allowing kids to face challenges, and highlights the need to align financial strategies with true life goals rather than tax optimization.
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Start With Purpose Before Complexity
- Complexity often precedes optimization without clarifying purpose; ask 'what is the objective?' before building structures.
- Many fancy estate or travel maneuvers fail because they don't match the original goal or scale to your needs.
Insure Only Catastrophic Risk
- Use insurance only for catastrophic risks you cannot self-fund; raise deductibles to reduce premiums.
- Avoid frequent small claims that can make you uninsurable and increase long-term cost.
Set Deductibles You Would Actually Use
- Review your policy deductible and ask: would I actually file this claim? Then raise the deductible to the level you'd self-fund.
- Check insurance costs before buying property because some homes are effectively uninsurable or extremely costly.