Markets are not stable systems. They evolve, adapt, and quietly erode the edges traders rely on. In this episode, Toby Crabel reflects on decades of experience navigating that reality, from the early days of Opening Range Breakout strategies to today’s fragmented and highly competitive landscape. He explains why momentum behaves differently now, how liquidity has shifted across sessions, and why execution has become a defining edge. The conversation also explores the limits of AI, the persistence of technical principles, and the importance of adapting without overfitting. At its core, this is a discussion about humility, uncertainty, and staying relevant as markets change.

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Episode Timestamps:

00:00 - Markets are probabilistic and inherently uncertain

01:40 - Introduction to Toby Crabel and his career

03:01 - From tennis to trading and early market exposure

06:10 - Opening range breakout and early momentum edge

08:04 - Why momentum strategies have deteriorated over time

14:21 - The disappearance of the “open” in modern markets

17:53 - Are markets changing or just the participants

20:34 - Liquidity events and large player behavior

24:14 - The role and limits of technical analysis

32:44 - Model decay and adapting systematic strategies

39:17 - Execution as a primary source of edge

40:40 - AI, automation, and the future of trading

51:18 - Effort vs result and the meaning of volume

56:56 - Are we entering a 1970s style macro regime?

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