Most Investors Are Asking the Wrong Question | Bob Fraser

Most Investors Are Asking the Wrong Question | Bob Fraser

June 16, 2026 · 1h 2m · Season 4 · Episode 11

About this episode

Bob Fraser discusses the importance of focusing on risk over returns in investment strategies.

Most investors start by asking: "How much money can I make?" Bob Fraser thinks that's the wrong question. In this episode, the co-founder and CFO of Aspen Funds explains why the best investors in the world focus on risk before returns, how billionaire investors build portfolios differently, and why protecting capital matters more than chasing upside. We dive into: ✅ Why good technology doesn't automatically create good investments ✅ The hidden problem with most capital raising strategies ✅ How billionaire investors think about risk ✅ Why Evergreen funds may outperform traditional syndications ✅ The biggest mistakes operators make when raising capital ✅ What Bob looks for before investing in any deal ✅ The future of multifamily, industrial, and retail real estate ✅ Why natural gas may be one of the most important investments of the next decade Plus, Bob shares lessons from being wiped out during both the Dot-Com crash and the Great Financial Crisis and how those experiences shaped the way he invests today. If you're an investor, operator, broker, or entrepreneur trying to build wealth that survives market cycles, this episode is packed with practical insights. Thanks To…

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