This week, Sim sits down with bestselling author and ex–financial advisor Glen James to unpack advanced investing strategies, including core and satellite portfolios, real diversification, and why long-term investors should ride out market cycles instead of timing them. They share practical tactics like rebalancing, dollar cost averaging, holding some cash for opportunities while keeping an emergency fund, and checking ETF overlap to avoid concentration risk. Sim and Glen also debate FIRE versus building a life on your terms, agreeing that consistent market returns that beat inflation plus strong career income and disciplined behavior usually outperform chasing hot stocks or using margin.

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