We Study Billionaires - The Investor’s Podcast Network TIP773: How Systems and Simple Math Shape Better Investing w/ Kyle Grieve
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Nov 30, 2025 Discover the power of mental models like feedback loops and kill criteria in shaping investment strategies. Learn how to manage uncertainty using the cone of uncertainty for position sizing. Explore the impact of scale on business behavior, revealing hidden risks during rapid growth. Uncover both visible and hidden forms of compounding that drive returns. Kyle Grieve emphasizes the importance of understanding randomness and regression to the mean for successful investing. These insights aim to refine decision-making and enhance long-term portfolio positioning.
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Exiting Thermal Energy With Kill Criteria
- Kyle used kill criteria on Thermal Energy International and sold when momentum lacked.
- He exited in Feb–Mar 2025 before the year deadline after KPIs proved unreachable.
WeWork's Scale Fueled Fragile Growth
- Kyle recounts WeWork's revenue growth that cost more than it earned and destroyed value.
- Misleading KPIs and incentives led WeWork to spend $1.9B to generate $1.8B revenue.
Turn Processes Into Algorithms
- Encode investment rules as algorithms to turn inputs into consistent outputs and remove ad-hoc bias.
- Follow the algorithm's prescribed action or it becomes a useless model with no real-world effect.
