Ask The Compound

What’s the Best Time to Invest?

19 snips
Jul 23, 2025
Discover the best times to invest, especially during market downturns, and learn about dollar-cost averaging for better long-term returns. Explore the complexities of employee stock options and the risks associated with investing in private companies. Delve into the balance between auto loans and market trends while evaluating financial flexibility. Uncover how retail investing strategies and technology shape market behaviors, and consider Bitcoin's role in portfolios alongside health and wellness automation for ongoing success.
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ANECDOTE

Investing Through a Lost Decade

  • Ben Carlson started investing during the lost decade of the 2000s, beginning in 2005-2006.
  • He considers those investments among the best he’s ever made due to dollar-cost averaging during downturns.
INSIGHT

Volatility Benefits Long-term Investors

  • Investing during market downturns sets up for better future returns.
  • Volatility should be welcomed by net savers for improved entry points over time.
INSIGHT

Complexity of Incentive Stock Options

  • Incentive Stock Options (ISOs) come with complex tax and timing rules.
  • Exercising requires careful planning and often expert consultation to avoid costly mistakes.
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