Shashi Kewalramani has built a nonlinear career across elite private practice, the U.S. Attorney’s Office, criminal defense, the bench, and now mediation.

This episode is about how skills compound across those chapters.

Some of the most valuable legal skills are not built in the most obvious places. In this episode, we explore:

Nonlinearity

openness to roles that do not look “on path” from the outside

why the safe path is not always the path to the best skill development

how varied experiences can clarify what you are actually good at

CJA

trust is built through time, transparency, and action

indigent defense can be elite training in client counseling

the hardest thing is often getting the truth from your own client

Magistrate jurisprudence

magistrate roles are underrated schools for writing, discovery, and case management

repetition builds judicial pattern recognition

Compounding advantage

skills learned in one role transfer into the next

deep listening, credibility, and clear explanation become differentiators later

a nonlinear career can produce a more durable kind of expertise

If you liked this episode, here are 3 others you might like:

• Judge Vince Chhabria for more on why process is substance, and how judges think about managing real cases in real time.
• Judge Matthew Kennelly for a deeper look at judicial decision-making, docket management, and what credibility looks like from the bench.
• Louis Tompros for another conversation about nonlinear legal careers, adjacent opportunities, and building something distinctive over time.

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.

Judge Richard Linn first pointed me to Louis Tompros years ago, when he told me my entrepreneurial approach to breaking into patent litigation reminded him of one of his former clerks. The story he shared stayed with me: Louis created his own chance to argue at the Federal Circuit by stepping into a pro bono inventor appeal.

In this episode, we explore how Louis has built durable edge through high-agency adjacent bets:

Agency

• create your own reps instead of waiting for permission
• take manageable risks to accelerate learning
• use pro bono work, teaching, and relationship-building to create career-accelerating opportunities

Adjacency

• bounded adjacent bets strengthen the core rather than distract from it
• trial and appellate work sharpen each other
• patent, copyright, and trademark work inform each other
• plaintiff and defense work reveal the other side’s blind spots

Teaching

• teaching forces you back to first principles
• it makes you more creative as a practitioner
• in a mistrust-heavy courtroom, the best advocates help the audience feel capable of deciding

Client perspective

• the client is the fourth audience
• you can win the case and still miss what matters most to the client

Gift-giving

• long-term business development starts with doing useful things for people before there is any immediate return
• relationships compound on an uneven timeline
• doing good work and doing the right thing are not separate strategies

The throughline is simple: create your own reps, make bounded adjacent bets, and let the learning compound.

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.

Neel Chatterjee has been testing some assumptions. In Neel's return to the podcast, we discuss what's changed in how he works.

The recurring theme of this episode was testing assumptions. That includes:

• testing what jurors really think about "big tech companies"
• building consensus through a new model of a professional association of lawyers, Law Firm Partners United
• changing his belief of how to go to trial based on what he learned from fifth-graders.

We also talk about specific techniques to use to invest in your network, like looking for the "twofer".

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.

Timothy Yoo is a first-chair trial lawyer who treats litigation like sport. Tim models his preparation and execution based on principles elite performers use:

• Prepare your physiology. Cortisol and adrenaline are part of the job; rehearsal is how you meet the moment.
• Pre-commit decisions. Use decision trees in outlines so you avoid reactivity under pressure.
• Credibility isn't just what, it's also how. Factfinders and clients read conviction, nuance, and authenticity through delivery.
• Be a reliable narrator. Your job is to help factfinders see the other side and draw their own conclusions.
• Adversaries are opportunities. Opposing counsel is your foil/dance partner, then you shake hands at the net.
• You'll use everything. Variety across matters compounds into mastery for the next big stage.

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 Mani was an associate at Susman Godfrey, he took a new colleague out for lunch for a vulnerable conversation about the demands of elite practice.

A decade later, Mani's lunch friend was now a rainmaker - and Mani was who he called for funding.

In this episode, we explore how Mani has used principles of trust, focus, and alignment to go from trial lawyer to GC of a multi-strategy fund to launching a litigation fund:

• Trust
  • being trusted as a peer trial lawyer created the relationships that led to the fund
  • the intangibles become the tangibles
• Focus
  • focusing on Texas trial lawyers creates operational excellence
  • it also enables them to act faster on decaying assets using limited information
• Alignment
  • aligning upside and downside with firms creates a flywheel for trust and repeatability
  • it also allows them to take risks others shy from

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.

Joe Ahmad is a trial lawyer who’s tried 100+ cases and built his entire approach around a simple premise: trials are a risk sport. If you need certainty, don’t go to trial. 

In this conversation, Joe breaks down what separates persuasive advocates from “polished” advocates, and why the jury can sense the difference immediately. He shares specific stories (including a New Year’s Eve mistrial decision he’d never repeat) and practical techniques for dealing with bad facts, corporate narratives, and the emotional game of the courtroom.

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.

Patti Burris had two kids and an associate's degree when she started her path towards law school. Yet she made her way to the top of her class by building systems to succeed even when there wasn't a safety net. And she's reframing her biglaw path from a necessary drudge to an opportunity to build a rewarding life. 

Patti's law school story begins with walking into the wrong job interview, which led to a life-changing mentorship. She shares the principles she used to call her shot in law school and end up at the top of the class through relationships with peers and professors, systems for learning, and cycles of sprints and rest.  

Now, as a driven biglaw funds lawyers, Patti shares the formula she uses to ensure she's investing in herself every week. Patti also shares how she stacks goals (social, academic, professional) for exponential returns.

This episode is special because it's both incredibly inspirational and full of practical techniques to achieve more with limited time. Patti has challenged me to make the most out of my time to ensure I'm living in line with my values and ambitions. 

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.

Priyanka Timblo left the comfort of Paul Weiss to join a five-year-old litigation boutique, betting on a place where she could practice the skill she knew she was best at: being on her feet in court. That calculated risk paid off spectacularly, culminating in a $101 million jury verdict against Walmart in Arkansas, one of the largest verdicts in the state's history.

Her path wasn't conventional. A Canadian law school graduate who was told by recruiters to pursue business development instead of litigation, Priyanka has built her career on being underestimated and using it as fuel. Priyanka lays out how starting as an associate, she leveraged being underestimated to prevail in overlooked opportunities. We also explore the anti-optionality path in law — the competitive advantage in getting good at one thing and sticking with it. 

Priyanka talks about what it takes to continue down this path: the sacrifices in her personal life and the challenging and rewarding inner-game of skill mastery. 

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.

Judge Vince Chhabria is a district court judge in the Northern District of California. When I shared with previous podcast guests I was interviewing Judge Chhabria, the excitement was palpable - these experienced litigators think of Judge Chhabria as "insightful", "focused", and "sharp", and this is a rare opportunity to learn how an influential judge thinks.

Judge Chhabria and I talked about:
- his unexpected path from the office of the San Francisco City Attorney's Office to the bench, any why city attorney roles are so valuable. 
- the surprising impact of case management on justice, and how few motions are decided by precedent
- what keeps the job interesting 11 years into the role
- why moving cases forward is an underrated part of public service
- the "memdispo" technique that efficiently allocates judicial resources to opinions 
- what he misses most about not being a federal judge
- his most important career advice for his clerks

We also discuss how he researched and considered precedent for the recent Kadrey v. Meta decision on fair use in generative AI. 

Any lawyer looking for an original approach to career decisions and how they practice should listen to this episode. 

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.

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.