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MicroStrategy's volatility, especially in comparison to Bitcoin itself, poses challenges for potential investors looking to enter the market. The speaker emphasizes the difficulty of timing the market with MicroStrategy, noting that it can be more challenging to enter MicroStrategy than Bitcoin due to its intense volatility and rapid price movements. Acknowledging the complexities associated with MicroStrategy's price action, the speaker highlights the importance of understanding one's position, the pricing dynamics, and the financial analysis required to navigate the market effectively.