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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.
About the host:
Khurram Naik is a partner at Freshwater Counsel, a boutique recruiting agency focused on patent litigators. Before founding the agency, he practiced patent litigation at Goodwin. Khurram hosts Khurram’s Quorum, a podcast with in-depth conversations with federal judges, first-chair trial lawyers, and chief legal officers on their career challenges and successes. Khurram also shares insights on LinkedIn.
Dai Wei Chin Feman is Managing Director and Corporate Counsel at Parabellum Capital, a litigation funder. This conversation gets practical in breaking down the system Dai Wai has built for career success: a diversified portfolio of relationships, skills, and value-creation mechanisms.
Business development creates differentiation when technical skills are commoditized.
Optionality multiplies this by developing multiple career paths simultaneously.
Affinity networks become firm-wide value platforms, not just personal networking.
Deliberate generosity treats relationships like portfolio diversification - invest broadly since you can't predict which connections matter.
Policy expertise becomes a defensive moat in niche industries.
Progress from "say yes" to strategic "no" to protect your systems while preserving ability to seize high-value opportunities.
Daily habits (20-minute social support + real-time alerts) create information arbitrage at scale.
Raw talent isn't sufficient. These strategies build transferable assets that maintain value across market conditions.
About the host:
Khurram Naik is a partner at Freshwater Counsel, a boutique recruiting agency focused on patent litigators. Before founding the agency, he practiced patent litigation at Goodwin. Khurram hosts Khurram’s Quorum, a podcast with in-depth conversations with federal judges, first-chair trial lawyers, and chief legal officers on their career challenges and successes. Khurram also shares insights on LinkedIn.
When tech platforms face “bet-the-company” speech fights, they call Ambika Kumar. We dig into how Ambika built a First Amendment practice from Seattle, argued a 7:30 a.m. TRO that blocked the first TikTok ban, and balances high-stakes litigation with raising two kids.
Ambika explains why eagerness is an asymmetric bet, how concise emails and phone calls keep clients calm, and what Section 230’s future means for AI. She also opens up about career inflection points, from early mentor hacks to leading headline-grabbing cases.
About the host:
Khurram Naik is a partner at Freshwater Counsel, a boutique recruiting agency focused on patent litigators. Before founding the agency, he practiced patent litigation at Goodwin. Khurram hosts Khurram’s Quorum, a podcast with in-depth conversations with federal judges, first-chair trial lawyers, and chief legal officers on their career challenges and successes. Khurram also shares insights on LinkedIn.
Quinn Emanuel partner Manisha Sheth has moved twice between elite private practice and high-stakes public enforcement. In this wide-ranging conversation we discuss:
Listen for practical insights on career strategy, process and delegation as competitive advantages, and a couple mountaineering stories that will make your palms sweat.
About the host:
Khurram Naik is a partner at Freshwater Counsel, a boutique recruiting agency focused on patent litigators. Before founding the agency, he practiced patent litigation at Goodwin. Khurram hosts Khurram’s Quorum, a podcast with in-depth conversations with federal judges, first-chair trial lawyers, and chief legal officers on their career challenges and successes. Khurram also shares insights on LinkedIn.
Want a 20-minute bootcamp for your LinkedIn presence? Episode 037 for Khurram's Quorum is a little different. My guest is Sunny Kim, who went from biglaw to make a big reset for her career helping lawyers find their voice in social media.
We cover how Sunny tinkered her way into discovering some of the best ways for lawyers to share their stories to build trust and authority with peers and clients, and get into brass tacks about how to position yourself on LinkedIn through your profile and posts.
At the end of this 50 minute episode, you'll understand why you should bother sharing your ideas on LinkedIn, and have an easy playbook for getting started.
Randy Gaw is the co-founder of Gaw Poe LLP. Randy left biglaw for a more direct path to first-chair trial work and strategic autonomy. At his boutique, Randy focuses on complex business litigation and high-value contingency work. We discuss:
As a partner at HWG, Hilary Gerzhoy advises law firms, partners, and GCs on the messiest, most human decisions lawyers make. In this episode, Hilary and I talk about why most ethics violations are rooted in fear, not greed, what really motivates risky behavior during lateral moves, and why great lawyers lead with empathy - and still set boundaries.
Jamie Nawaday is Head of Seward & Kissel's Government Enforcement and Internal Investigations Practice and the founder of Disrupting Drinking, where she speaks on personal change and cultural change to disrupt the corporate cocktail culture. Jamie has the unique insight that drinking isn't just about wellness - it reflects how the legal profession handles stress, bonding, and belonging. We explore how storytelling and authenticity are not side skill, they’re core to both legal persuasion and personal transformation. That change doesn't have to come from quitting your job and going all in - you can start a courageous conversation from within.
Vishal Shah is the founder of Shah Litigation, a high-stake employment litigation firm. This is a unique opportunity to examine the strategy and values a biglaw associate used to launch and grow a successful law firm. We talk about the decision to switch to the other side of the v., how he researched the opportunity to identify his niche, his approach to a national trial practice, the unique dynamics of the plaintiffs' bar, and business development strategy.
Pratik Shah is the Practice Head of Akin’s Supreme Court and appellate practice. Pratik breaks down his achievements and shares the values and principles he used to challenge himself and create opportunities. This conversation explores three underdiscussed topics, the market for appellate litigation, the business of appellate litigation, and the seismic shift in appellate practice in the past couple decades. We also explore how to make decisions about the kind of practice to join and build.
About the host:
Khurram Naik is a partner at Freshwater Counsel, a boutique recruiting agency focused on patent litigators. Before founding the agency, he practiced patent litigation at Goodwin. Khurram hosts Khurram’s Quorum, a podcast with in-depth conversations with federal judges, first-chair trial lawyers, and chief legal officers on their career challenges and successes. Khurram also shares insights on LinkedIn.
From the publisher's feed
How elite lawyers make decisions.
Traditional legal media focuses on outcomes. But this podcast focuses on operating principles: how lawyers assess risk, build judgment, and choose…
The podcast is a library ambitious lawyers can consult to learn how exceptional lawyers think, and our guests return to document their progress.