Dustin and Adam explore the psychological shift and risk tolerance adjustments required when transitioning from investing with outside income (such as from a job or business) to living solely off investment returns.
They contrast the security of adding to investment principal from W-2 or other active income against relying entirely on investment returns, and share insights on why real estate provides stability during stock market volatility through consistent rents and lower liquidity, using the April 2025 stock market drop as a timely example..
This episode includes practical approaches to portfolio construction, position sizing, and deployment strategies for windfalls that maintain both cash flow and future opportunities. Whether you’re looking to leave your job or trying to balance both worlds, the discussion offers a valuable perspective on building resilience into your investment strategy, particularly through real, cash-flowing assets.