On this week’s episode, Kent is joined by Bob Fraser. Bob explains why many passive investors underperform not because they choose bad deals, but because they misunderstand portfolio construction and risk. He breaks down how volatility quietly erodes compounding, why true diversification requires uncorrelated assets, and how family offices think differently about capital preservation. The conversation also explores private credit, real estate’s role in reducing portfolio swings, and why operator alignment matters most when markets turn.

Where to find Bob:

• Website: https://investlikeabillionaire.org
• Company: https://aspenfunds.us
• LinkedIn: https://www.linkedin.com/in/bobfraser10/

Key Takeaways

• Volatility can destroy long-term returns even when average performance looks strong
• True diversification means owning assets that do not move together during downturns
• Family offices prioritize downside protection over headline returns
• Private credit and preferred equity can reduce portfolio risk while generating income
• Operator co-investment is one of the strongest indicators of alignment

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https://hudsoninvesting.com/

Production by Outlier Audio