Rich Habits Podcast

Q&A: Investing While Unemployed, Attending College in an AI-First World, & Selling $250K of Microsoft

Jan 22, 2026
This discussion dives into navigating unemployment by prioritizing short-term gigs to maintain cash flow. It highlights using AI tools to enhance job searches and craft standout applications. The hosts evaluate a robust ETF portfolio while emphasizing correct fund weightings. They also tackle the question of whether college is worthwhile in today's AI-driven landscape, suggesting alternative paths like trades or entrepreneurship. Lastly, tax-saving strategies through LLCs and expense tracking are explored for aspiring entrepreneurs.
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ADVICE

Pause Investing To Preserve Cash

  • Pause retirement and taxable investment contributions and prioritize your emergency fund while unemployed.
  • Cut discretionary spending and conserve cash until you secure steady income.
ADVICE

Get Paid Fast, Not Fancy

  • Get any available paid work now; prioritize immediate income over prestige.
  • Use AI tools to refine resumes and target more suitable job roles quickly.
INSIGHT

Time-To-Pay Matters In An Emergency

  • Quick side-hustles often take weeks to monetize compared with immediate hourly work.
  • Choose options that deliver cash in days during financial emergencies.
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