Going live with real money brings realities that paper trading simply cannot replicate. In this episode, Kirk walks through the five essential things every trader should understand and consider before transitioning from paper trading to live trading.

From the limitations of paper trading to the execution challenges of real markets, we explain why strict expectations, conservative assumptions, and a solid understanding of liquidity are crucial.

Kirk also breaks down how to prepare for in-the-money positions, why orders don’t always become fills, and why keeping your Option Alpha and brokerage accounts aligned is so important. Plus, an important reminder that the hardest part of live trading is sticking to your strategy when emotions flare.

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In this interview, Kirk sits down with Kevin, a long-time Option Alpha member who began trading in the aftermath of the 2008 financial crisis. Kevin shares how he turned his small beginnings into a consistent, structured approach that scales with his portfolio.

Kevin details how he spent years learning before placing his first options trade and how those early experiences shaped his disciplined, rules-based philosophy. He explains how he uses position sizing, trend, and DTE selection to create repeatable setups in the corresponding position type.

Kevin also walks through how automation, weekly reviews, and a focus on process over prediction helped him build consistency through market downturns, quiet periods, and personal setbacks.

Kevin enters each week with a plan and relies on automation to execute that plan to reduce noise and stay aligned with his long-term goals.

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Markets rarely behave as predicted by mathematical models, and extreme events occur far more frequently than traditional models anticipate. This episode explains why understanding probabilities, fat tails, and risk is essential for long-term success.

We also explore how traders can build more resilient systems by focusing on recovery time, appropriate position sizing, and avoiding strategies vulnerable to black swan events. Discover why win rate alone can be misleading, and how expected value offers a more realistic framework for navigating uncertainty.

Plus, Kirk shares how his own philosophy has evolved over the years and why automation can help enforce discipline and reduce emotional decision-making.

See full show notes here