In episode 157, we welcome back our guest from episode 83, Randy Swan. Randy and Meb kick off the conversation by getting into Randy’s new book, and what motivated him to write. Randy talks about having an opportunity to go back and write about how and why Swan operates the Defined Risk Strategy. In getting into the investing framework outlined in the book, Randy explains why he thinks investors face a “Dual dilemma,” forced to stick with conservative investments, or step out into riskier assets and sacrifice protection from their conservative investments. He goes on to state his thoughts on the evolution of democracy and the role debt has played in decision making in government and central banking. He then goes deeper into this dilemma by explaining the rationale behind his thinking about this problem, and his expectations for low returns in both equity and fixed income markets going forward. Meb asks Randy to discuss why it’s so important to focus on avoiding large losses and investor psychology. Randy follows up with thoughts on portfolio construction concepts he feels are important to add to the current thinking to seek return streams that are more in line with investor expectations. The conversation then shifts into the genesis behind Swan’s flagship, Defined Risk Strategy, the idea that correlation of returns is unreliable, especially in times of crisis, and the difficulty in defining risk in an investment portfolio. He then walks through the portfolio management process and covers some examples of the mechanics during bear markets. As the conversation begins to wind down, Meb asks in what periods this strategy is expected to shine vs. struggle. Randy walks through the desirable market conditions for Swan’s strategies. All this and more in episode 157.