041: Rakesh Kilaru on decision-making tools honed at the White House, trial strategy through subtraction, and what it takes to build a high-stakes trial boutique

Rakesh Kilaru is a partner at Wilkinson Stekloff. In a few years, Rakesh has resolved headline-making disputes, including defeating a $21 billion challenge to the NFL’s media model, defeating the FTC’s challenge to Microsoft’s $68.7 billion acquisition of Activision Blizzard, and negotiating an innovative settlement over the NCAA’s compensation rules. And he's barely over 40. I reached out to Rakesh to learn more about his practice, and the conversation flowed. For someone of his accomplishments, Rakesh is remarkably humble. He's driven by excellence and impact. We could easily have recorded a much longer episode. In this episode we discuss these frame-shifting principles: - Practice making decisions under uncertainty. From his time at the White House, Rakesh learned to map the real stakeholders, build trust as an honest broker, and make sure everyone who needs a say is actually in the loop before deciding - Choose environments that improve decisions. A fixed-fee model removes distortions, encourages collaboration, and lets teams right-size effort to outcomes. - Focus. Work out from first-principles what is helpful to a jury or judge, and continually ask what are the 1-3 issues that matter. - Challenge assumptions. Don't rely on conventions from the practice area, but identify your own solutions. - Develop a generalist mindset. You can settle cases, you can try them. You can take principles learned in products liability to antitrust cases and beyond.

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041: Rakesh Kilaru on decision-making tools honed at the White House, trial strategy through subtraction, and what it takes to build a high-stakes trial boutique is an episode from Khurram's Quorum by Khurram Naik.

This episode is 97:02 long.

This episode was published on Aug 18, 2025.

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