Gurbir Grewal's meteoric ascent to the Director of the SEC's Division of Enforcement may seem charmed, but here Gurbir shares the tradeoffs and costs of the steps he took. Gurbir is uniquely down-to-earth for someone so public and prominent, and this interview went deep into the decisions and experiences that shaped his path.

It's inspiring to hear the origin of The Sikh Coalition in the aftermath of 9/11 and the disproportional impact on the Sikh community. But it's all the more remarkable to hear how Winston & Strawn partner Amandeep Sidhu and his cofounders built an organization around consensus-building causes that benefit multiple communities. And how Amandeep did it by getting stakeholders at his law firm to support him along the way. This episode is for anyone looking to make a social impact and learn how to develop thoughtful responses to the inevitable crises and opportunities.

As the CEO of Litera, Avaneesh Marwaha is responsible for setting the pace of innovation at a leading legaltech company. So when Avaneesh shared some of the goals he set for himself at 25 that he's still carrying out at 40, I had to dig in to learn more.

A company like Litera has a powerful lens on the legal industry and where it's headed. So we spent a lot of time talking about core insights like what makes clients stick with law firms. We also discuss the three areas Avaneesh sees opportunities for lawyers to move into legaltech, and the #1 skill lawyers need to develop now to advance their practice.

This conversation is for anyone interested in learning what it feels like to bet on yourself and to move into a growing frontier.

When I was introduced to Kenneth Anand, I was equal parts excited and anxious. I'm no more than a casual fan of Kanye's work and I've never been into streetwear. But how could I say no to meeting the ex-GC of Yeezy?

Kenneth and I ended up having a sprawling conversation about his new book Sneaker Law and how it departs from traditional legal casebooks. We talked about his journey from producing hip hop to law and how after 15 years of practicing law he oriented himself back to his roots in streetwear.

We talked about how the methods and culture around sneakers and streetwear is moving into other industries. And we talked about lessons learned from Kanye himself.

It's hard to picture a better time to grow a cold chain technology company like Therma, and it's even harder to picture the legal clinic origins of the business. Manik Suri has made a career out of synthesizing surprising insights and finding talent to partner with. In this episode we discuss what Manik learned from a friend that ended up as a presidential candidate on how to channel your inner confidence. You'll learn a new question to ask yourself "what kind of energy am I burning?" And we talk about how to manage downside risk by getting over the fear of failure.

Federal judges are fascinating because they resolve high stakes matters addressing a wide swath of issues touching on every aspect of society. And because of their limited resources and the 30-some new cases they get a month in a busy court like the Northern District of Illinois, they have to become experts at building systems for making decisions.

So I'm happy that I got to spend two hours with Judge Matthew Kennelly to learn about what he does. We explored the tools he's developed for helping bring disputes to resolution in the 22 years he's been on the bench.

We talked about some of the interesting implications of lifetime tenure, how he's changed how he manages his docket, new ideas and how they spread among judges, what's difficult about sentencing, and the tradeoffs between standardization and individual attention on cases.

Judges are used to people laughing at their jokes, but Judge Kennelly is actually funny (although I won't repeat that he's a "pillar of our community" because apparently he's heard that enough times). I hope you'll enjoy this rare in-depth conversation.

I'm thrilled to share this interview Chief Judge James Holderman (ret.) formerly of the Northern District and now a mediator at JAMS ADR. Externing for Judge Holderman in law school was an inflection point in my legal development, and I feel like I've been riding that wave ever since. It's rare to get a chance to sit with a federal judge and explore lessons from 30 years on the bench. We talked about his upbringing on a farm in Southern Illinois and some of the surprising legacy that's had on his judicial career. We discussed how he wielded authority from the bench, and the hardest task he faced on the bench. Judge Holderman shared some of his prescriptions for improving how federal litigation is conducted.

When Archit and I planned to do this episode in the new year, we didn't quite expect this much attention on Robinhood. We explore Archit's arc from the first lawyer at Robinhood to general counsel. We talked about the lessons learned from building a team of dozens of lawyers, and how he approached the novel legal and regulatory issues along the way. We covered the regulatory landscape for fintech companies, reasons to be bullish on crypto, and yes, we talked about Gamestop.

I didn't expect to interview someone at another Florida sports franchise so soon, but I'm glad I had a chance to talk to Megha Parekh, Chief Legal Officer of the Jacksonville Jaguars. One of the most interesting themes from the conversation was around work-life integration and the systems she's used to foster it in herself and others. There were insights into the relation of remote work and inclusivity, and lessons on the perils of perfectionism. This interview is for anyone interested in being unapologetically yourself and refusing to cut out the fun in your life.