Key insights

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1. Rationalizing Pain is a Professional Superpower.

Raj’s diagnosis forced him to develop a relationship with "bad pain". By taking up ultra-running to create "good pain" that he could control, he learned to rationalize discomfort. This ability is a 1-to-1 carryover to the legal and startup sectors, where managing high-stress, high-volatility environments requires the same mental endurance.

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2. Hire for the "Burning Building" Scenarios.

In a high-growth startup, everything can go "haywire" instantly. Raj emphasizes that GCs must hire people based on their willingness to "run into the burning building" with them. Finding team members whose mission-driven "why" is aligned with the company ensures they will have your back when the whole thing is falling apart.

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3. GCs Must Be Fundamentally "Why-Interested".

Technically amazing lawyers are plentiful, but an effective GC must be a commercial leader. This means constantly asking why a team is operating a certain way or why the board wants specific outcomes. If you aren't interested in getting under the skin of every department, you will struggle to move from advisor to operator.

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4. The "Mosaic" Approach to Career Diversity.

Raj advocates for filling life with a diverse range of experiences—from social impact projects in Africa to predictive climate modeling. He argues that a meaningful life is built by doing what is "right in the moment" rather than overthinking a long-term footprint, ultimately leaving a legacy through action rather than intent.

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5. Closing insight

Professional endurance is built on the ability to rationalize discomfort and act decisively with imperfect information. By embracing your personal "superpowers" and fostering deep relationships, you ensure that you don't just survive the burning building—you lead the way out.