Khurram’s Quorum – Ep 034: Jaimie Nawaday on Disrupting Drinking and culture change through storytelling

Khurram’s Quorum – Ep 034: Jaimie Nawaday on Disrupting Drinking and culture change through storytelling

Jaimie Nawaday is the head of Seward & Kissel's Government Enforcement and Internal Investigations practice—and the founder of Disrupting Drinking, a speaking venture challenging the corporate cocktail culture that's woven into BigLaw, finance, and consulting. After quitting drinking in late 2020, Jaimie realized the story she wished she'd heard during her years of nightly bourbon and Scotch Fridays at the US Attorney's Office didn't exist. So she built it herself.

In this conversation, Jaimie breaks down why drinking culture binds lawyers to work (caffeine to power through the day, alcohol to shut down at night, repeat), how Gen Z's shift away from alcohol is finally forcing the legal profession to catch up, and why her white-collar defense practice—built on deeply personal storytelling and credibility—made launching Disrupting Drinking feel inevitable. She also shares the trial that transformed her from a terrified junior AUSA reading trial technique books on the subway into a confident partner, why her daughters' wrestling careers inspire her to take risks ("I'm not getting pinned in front of people—much less at stake"), and how she's challenging the story that lawyers have to play it safe with their reputations.

We discuss why listening is Jaimie's differentiator in white-collar defense, how the best advocates frame seemingly preposterous theories ("You've got target and victim in the wrong buckets"), and why she chose speaking over writing a book—because discrete talks let you iterate, get feedback, and build an audience before committing to a manuscript.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Drinking Culture as a Control Mechanism: Jaimie argues drinking in law isn't just about stress relief—it's a tacit way to bind you to work. The cycle of caffeine to get through the day, alcohol to shut down at night, then collapsing exhausted means you barely survive, let alone thrive. You don't have energy to work out, show up extra for family, or pursue anything outside work—so work becomes your only priority by default.
• From Terror to Transformation: The Trial That Made Her: Jaimie's first major trial as an AUSA—representing the government against Bank of America with 3-4 AUSAs facing 100+ defense lawyers, a Brendan Sullivan-led team, and Judge Rakoff's breakneck schedule—was so high-stakes she was reading trial technique books on the subway. But winning that case gave her the confidence to think "I can learn anything, I can do anything" and set the foundation for her partner-level practice.
• Credibility Is the Differentiator in White-Collar Defense: In a field full of excellent ex-prosecutors with similar backgrounds, Jaimie's edge is being earnest, listening patiently, and building trust with both clients and the government. When she advanced a "preposterous" theory—that the government had target and victim in the wrong buckets—her credibility got her a hearing that others wouldn't receive, and she flipped the case.
• Why Speaking Beats Writing (for Now): Instead of committing to a book, Jaimie chose discrete keynotes and workshops—faster to execute, easier to iterate, and you get immediate audience feedback. You can do a dozen talks, learn what resonates, and then write the book once you know there's an audience and you've refined the message.

Listen Now

Catch the full episode on your favorite podcast platform.

Spotify

Or click here to listen on Spotify

Apple Podcasts

https://embed.podcasts.apple.com/us/podcast/034-jaimie-nawaday-disrupting-drinking-and-culture/id1536579571?i=1000704908143

Or click here to listen on Apple Podcasts

Full Transcript

Khurram Naik: This is Khurram with Khurram's Quorum. My guest today is Jaimie Nawaday. Jaimie is the head of Seward & Kissel’s Government Enforcement and Internal Investigations practice. I learned about Jaimie from a post she made on LinkedIn about cutting out drinking and her new venture to disrupt the role of alcohol in the practice of law. I myself cut out alcohol more than five years ago as an associate, so her venture seems to really capture the moment. I think you'll enjoy learning about how a seasoned white-collar lawyer is finding space for entrepreneurship. This is a great episode for exploring the nexus between personal and professional growth. Jaimie, thanks for coming on. I was really struck by your LinkedIn presence. You did something that I've never seen before, which is, it seems to me, took the effort to share your story in a skillfully produced way about your experience with drinking and then choosing to no longer drink, and then sharing that story about your work as a lawyer in this new format. So you have this new business venture called Disrupting Drinking. I was so struck with that, and I'd love to hear a little bit about what Disrupting Drinking is and so we can talk some more about the impact it has on you and what you see for the legal profession.

Jaimie Nawaday: Sure. Disrupting Drinking is my new speaking venture. And it's also just an initiative to get the word out in corporate America about the high-pressure drinking culture, which to some extent has eased in the last few years. But there is the expectation, certainly in law, in finance, in consulting, in law enforcement, in all of these adjacent fields, that the professional world requires drinking, and often drinking hard liquor, in the case of say prosecutors in certain areas of law in particular. I would say especially trial law work and criminal law work, we see especially high levels of drinking and drinking hard liquor. And I sort of was the first lawyer in my family and had a certain amount of imposter syndrome, as we all do. And when you have imposter syndrome, you look around and see what everybody's doing. And in the legal world, that was drinking. And so I really wasn't a drinker before I was a lawyer. But I, you know, started out with wine. And then when I switched to the US Attorney's Office, I noticed that everybody was drinking Scotch and bourbon, and I started drinking bourbon whiskey as well. And over the course of a few years, I just noticed that I was drinking too much too often. It was basically a nightly habit. It wasn't that I was drinking so much at any given time—I wasn't a huge binge drinker or anything like that—but I knew it was too much and I knew I was too attached to it and it was holding me back. And it was hard for me to quit on my own, and I didn't feel like I could tell anyone about it. Certainly, with background checks and things like that that you have at the US Attorney's Office, it just felt like something I had to keep secret. I had to quit sort of through willpower alone. And that was really tough. And so I looked around just in media, on YouTube, in bookstores for stories of people who drank like me and had quit on their own. And I really couldn't find that story. And after I quit in late 2020, I started thinking about how much better my life had gotten once I quit. And I started thinking back on that period of time when I was trying and failing to quit and how a story like mine would have really helped me back then. And I used to just write in my journal New Year's resolutions and things like that, you know, resolve to drink less or only drink twice a week or something like that. And I just kept failing. And I think I would have quit years earlier had I heard someone share a story like mine earlier. So that's what led to Disrupting Drinking.

Khurram Naik: Yeah, so much of that resonates for me. I quit drinking roughly at the same timeline, about a year earlier. And so for me, it was definitely connected to practice. I mean, so I was too broke before law school and in law school to drink much, and then finally could afford alcohol and I noticed my first year was definitely a stressful year. And I was going through like a bottle of bourbon a week and I had the weight gain to show for it and I was just like blown away by that. But so then I kind of pulled back from that and it was fine for a while, but then yeah, in 2019 I noticed I was really in the cycle of caffeine to get me through the day and then alcohol at the end of the night and just the cycle wouldn't end. So then I cut out both at the same time. And yeah, I very much agree with you that there's just not a variety of stories about not drinking. I think first it's very abstract, like when you're in law school or in practice like there's some CLE you go to or whatever they say, "Hey, by the way, you know, too much drinking in the profession." Like, okay, one in three lawyers has an issue with drinking. Like, okay, I get all these numbers but it's just not tangible. And so yeah, I think hearing stories from successful lawyers like yourself to say like, "Hey, like you thrived in government practice, you're thriving in private practice." Hearing stories from lawyers like yourself would definitely change a lot. I'm curious if you think that—how much has changed since the pandemic? You know, of course, there was a lull, I think any number of people were drinking a lot at home. I think there's lots of figures that showed drinking went up a lot, which you know, is not surprising. And then so since then now people are of course—it's been at least a couple of years if not several that people have been getting back together for conferences. Do you think anything—have you noticed a change before and after, pre-pandemic, post-pandemic in terms of how much drinking seems to be part of legal culture?

Jaimie Nawaday: I mean, during the pandemic, just anecdotally, it seemed to be going way up. Just I guess just the way people were joking about it, sort of drinking at a much earlier hour in the day and sort of throughout the day. And you know, people having a lot of wine tastings, like Zoom wine tastings and things like that to socialize. And then I saw just statistics on how much worse problem drinking was during the pandemic and emergency room visits around drinking and things like that. So during the pandemic, it seemed to be getting a lot worse. Then I guess it wasn't immediately after the pandemic, but just the last few years, it seems like there has been a shift because we hear more and more about Gen Z drinking in much lower numbers. Dry January seems to be getting more and more popular every year. I just seem to hear from more and more people now that they've quit drinking or have cut way back on drinking. I notice that the mocktail menus are getting better and better. It seemed like it was really hard a few years ago to find—even in Brooklyn—to find real mocktail menus, and now we have non-alcoholic bars, there are non-alcoholic spirit stores, and pretty much every restaurant seems to have a decent mocktail menu.

Khurram Naik: Yeah, definitely notice that and there are still vestiges of it. I mean, I was at a conference recently, and so my wife was with the conference with me and my wife is pretty clearly visibly pregnant. And so someone—so I—she had seltzer, I had seltzer, someone walked up to me and said, "Oh, are you not drinking out of solidarity?" You know, just the default assumption is that you would be drinking. That that is the assumption is that what you would be doing.

Jaimie Nawaday: Right, and that's especially true at conferences. So to go back to your original question, I think I've seen changes in society, but I think the legal profession in particular is still lagging way behind. I think a lot of firm events, networking events, conferences are still—they're starting as more people are making noise about it and making the requests for non-alcoholic options, they're starting to include them more. But still, the socializing still revolves around drinking.

Khurram Naik: Yeah, I wonder if—I don't think there's going to be any clear answers to why there's this connection between drinking and law beyond the obvious: "Hey, it's a stressful job." There are many stressful jobs. And yes, we have enough income and so to be able to afford alcohol. So there are lots of answers for it. But I wonder if part of—you mentioned I've consistently understood that Gen Z is drinking less, and from my experience with people that are of that generation, yeah, they drink way less. And I'm so struck with it because I know that at that age I was trying to drink as much as possible, and so was everyone else that I knew. It was just a given and an assumption. And so I think some of it has to do with just a general interest in health that is, you know, a secular trend in health, you know, that people are more and more interested in health as we go along. But I also wonder to what extent drinking culture is tied to work culture in kind of binding you to work in every sense. And so, I mean, the extreme version of it is you see this in Japan and I think South Korea as well, where in Japan there's the concept of a "salaryman." And so the salaryman culture is like it's a—from I think the US advantage point—a very extreme culture where you're expected to work long hours for sure, but then also spend a lot of time after hours socializing and drinking a lot.

Jaimie Nawaday: Right.

Khurram Naik: And so probably from seeing something that seems like a more extreme example, you can understand how it works on that spectrum at all. And I think part of—it seems to me part of the history of the reason that drinking and law legal practice was so tied together was to bind you to your work. So it was a way of like, "Hey, like just the same socialization we were just talking about," but then also like, you're not—you're just—you're barely able to get by, right? You don't really—you're not able to thrive, you're not able to—so you're just—you just survive that day of drinking and now like the only thing that you have, you don't have energy to work out or maybe show up in an extra way for family or friends or whatever. So work is going to be the number one priority. So it's like a tacitly perverse way to like bind you to work. But I wonder if you've observed that, because that's something that I've noticed.

Jaimie Nawaday: That's interesting. I mean, it resonates especially in the trial context, I think, because you know, alcohol, of course, it doesn't—it doesn't really reduce stress or anxiety, people now understand. But it feels like it does in the moment, right? For the first hour, first half hour, right? So if you're working long hours at a trial, you're so high adrenaline and your nerves are so high all day long. And what's going to shut that off immediately? It feels like, well, a really strong drink, right? And so you can see how the culture would start is, you know, it's—it's the way you can power down very quickly once you're done with trial prep for the next day. But then you have that and you become worthless very quickly, so you, you know, you go home, you collapse asleep, you just get up and you do it all over again. You're not—you're not going to have—you want to shut down quickly. It feels like the quick fix, but then you're not going to be doing anything else productive. You're not really engaging with your family in any meaningful way, you're not going to go exercise or anything else, you're just going to collapse and then do it all over again, like you said.

Khurram Naik: Yeah. And so tell me about how you're approaching this. So you—you are a partner at a—at a litigation boutique, and so you've got a—a busy practice. How are you working this venture into your practice?

Jaimie Nawaday: Um, you know, I guess around Memorial Day, I just started setting aside time on evenings and weekends. And I'm, you know, I'm fortunate, my kids are teenagers now, so and they get around on the subway, so I don't—I don't spend, you know, all evening having to chauffeur them around to different places. They get around on their own. And I have a super short commute, about 10 minutes from downtown Brooklyn to downtown Manhattan. So I'm—I'm fortunate enough that I have a little more free time than I had when, say, the kids were younger. And just kind of mapped out little by little what it would take. And it felt much more realistic, I guess, and much more compatible with a legal practice to plan talks and workshops, to do sort of a speaking gig as a side gig, as opposed to say writing a book, which just felt much more daunting and would have taken a lot more time. To sit down and draft an hour keynote is a—is much more realistic when you have a full-time job.

Khurram Naik: You know what I also like about that is like, there's just—you don't have any clue like what the demand is for this book. But like a—you know, a talk is something that is—it's discrete and then you can quickly get some feedback from an audience and then learn what resonated in that and maybe you do a dozen of those, a hundred of those. At some point, you will understand, "Okay, let's see, there's a book to be written here." Then—then now I understand there's an audience for it and, you know, some of them have already heard me speak before on this. And then you're also able to like iterate on exactly on—on what we were talking about is just like what people are looking for. And so can you say some more about some of the—the groups that you think would be—your message would be helpful for?

Jaimie Nawaday: Um, I think law students for sure, because we all heard about in law school the rates of problem drinking among lawyers. And I'm head of associate recruiting now at my firm, and so I was—I was at a recruiting event recently at a law school and the—and we got to talking about drinking and Disrupting Drinking also. And a lot of the students I spoke with don't themselves drink for one reason or another and they were saying that they now have law school classes where you get the old "look to your left, look to your right." I think it used to be something like "one of you will drop out of law school," but now it's like "one of you will develop a problem with alcohol." And I said, "In what—what guidance were you given in terms of how to avoid this?" And they said, "Well, we didn't really get any." Just sort of the cautionary tale, the cautionary statistic, that sort of thing. So definitely I think law schools can benefit from this because we're scaring them, but we're not really giving them the tools yet. And I think to hear relatable stories and "here's what happened to me" and "here's—here's what I wish I had known and here's how I could have set myself up for a different trajectory in terms of that lifestyle," I think are super beneficial. Also incoming classes of associates or employees. You know, it's—I mean, I'm a lawyer, so obviously my initial audience is—is lawyers. But people in other industries face the same kind of pressure, especially other long-hour high-stress jobs like, you know, finance is another obvious one, consulting is another obvious one. But I would say it can be bar associations, firm retreats, groups of partners, team-building exercise, you know, wherever you're getting a group of people together in the professional setting, that's potentially my audience. Anybody who cares about mental health, wellness, any of those issues, drinking is tied into that. So if you're getting a group together to talk about any of those issues, I think that's a group that I can add value and speak to.

Khurram Naik: You know, what I like so much about that is the drinking is—there's definitely a key part of it that is solo, but of course, so much of the drinking is in a group context. So probably speaking to a group about, "Hey, here's an awareness for every single person here about the influence of this group on you," it allows all these people to individually and collectively choose different behaviors. And so it just—it's so timely, like you're speaking to them in the moment when it's most—that information is most relevant. It's just-in-time information that's the most relevant to them.

Jaimie Nawaday: Right, and there's, I mean, there's an obvious value proposition for firms and companies because, you know, drinking is just costing them all a ton of money. Not just in terms of actual alcohol that they're spending at events or on after, you know, firm-sponsored after parties and things like that, but just, you know, sick days, loss of productivity, workplace incidents. Almost, you know, throughout my career, every workplace incident I've been a part of on a case or seen it at some, you know, wherever I was, always involves alcohol, things like that. And—and women are so often on the receiving end of that, and of those incidents. And so it's also just important for kind of diversity and inclusion, you know, retention initiatives as well.

The Bank of America trial that transformed Jaimie is the kind of experience Joe Ahmad has had over 100 times. He told me trials are a “risk sport” — if you need certainty, don’t go to trial.

Khurram Naik: Yeah, I—I was searching through my phone through a conversation and I stumbled on an old thread with a former coworker. And so I just was immediately plunged into—to just like, you know, our world years ago. And I was—I was just scrolling through it and just, it was amazing how much, like we were talking about poor behavior of partners and just how much of it was associated with alcohol. It was just—that just happened this past weekend. It was just such a stark reminder of—of the associations you're talking about. Could we talk a little more about—so you mentioned some of the context, you know, for you personally in terms of, "Hey, like my children are a little more self-sufficient, so I—I have some space to take on." Can you say some more about, you know, you've been in—you've been at several firms in private practice, you've been in government practice, so you've had, you know, a rounded professional career so far. I don't know many or I—I'm just not thinking of any lawyers I know that have developed this sort of speaking bureau engagement platform venture. And so can you tell me more about how you came to—you talked a little bit about to say, "Hey, you know, I realized there wasn't a book here, but there was a, you know, a potential speaking opportunity here." I see so little of practicing lawyers doing something like that. So how did you even come up with the idea of like, "Hey, this is a thing, you know, like I can do this, I can speak and—and get paid to speak and add value in that way?" Like, how did you come to that idea?

Jaimie Nawaday: Um, that's a good question. I think some of it was—it was probably a combination of things. I mean, some of it was going to partner retreats and, you know, we—as all firms do, you bring in outside speakers on a range of topics. And so, you know, I knew it was a thing for law firms and elsewhere. And then just sort of seeing public speaking courses and gigs and things like that. I—I must have been talking about it or something because suddenly my social media feed was full of it. And then I started poking around at some of those classes and kind of seeing what the—I wanted to see, you know, what does the market already have in terms of people speaking on this topic. I started looking around on TED talks and other things, and it really seemed like there are obviously lots of resilience speakers, grit, all these wellness speakers, but I did see that there was a gap around drinking. And I thought with my background doing trial work, doing a lot of public speaking, it just seemed like a natural fit.

Khurram Naik: And then what is the—so you saw the opportunity for how your skillset would be valuable to other people. What did you identify as the payoff to you? And of course, it will change over time, but at this—heading into the venture, just I—I want to replicate that decision for anybody else that has an entrepreneurial instinct and looking for, you know, inspiration from what you're doing right now. You know, what was—what was the early value that you identified that you would get out of this?

Jaimie Nawaday: I think it was—it just felt like something I had to do, I think, just in order to be fulfilled. It's very satisfying to me when somebody says, you know, "When you told that story, it had this effect on me. It gave me hope. It inspired me in some way." And I've had that in different contexts. For instance, since I quit drinking over the past few years, I would sometimes post on social media different athletic things I was doing as part of different health kicks, but I wasn't really sharing the drinking part of my story at that point, I was just—I mentioned that I had stopped drinking sort of as part of a health kick or a health challenge. But a lot of people would tell me, "You know, I've been inspired by your social media posts and I started doing this or I started…" and that's always been very gratifying to me, super meaningful, and… and then I was at a conference last spring, it was a diversity conference, and we talked about—one of the panels was on socioeconomic diversity. And there was a panel on that we don't give enough airtime to people who grew up with—without money. Like we're sort of focusing on racial diversity and all these other things that we should be focusing on, but we don't often talk about what it's like to enter the law firm world when you grew up without money and how foreign that world can feel when you don't know the types of food you're eating, when you're not—when you don't feel sophisticated at these fancy restaurants that you go to suddenly as a summer associate and that sort of thing. So I told my story about growing up, you know, maybe barely—we'll say barely middle class in central Pennsylvania and what it was like when I was a summer associate and not, you know, not knowing how to eat the food and what it was and sort of feeling a little bit like a hillbilly. And the—and again, like when people came up to me after that panel and said how much my story resonated, how they felt seen and understood, I just—I just love those moments of connection. Like that's what I enjoy so much about getting up in front of people and telling a story. So just knowing that stories can really help someone change their own lives. And so what I got out—I guess what I saw myself getting out of it was just knowing that I could help someone or give someone else hope because I know what it was like when I was trying to quit and it was just—it was a very scary and lonely place to be. And so if I could help someone else out of that, that would mean the world to me.

Khurram Naik: Where in central Pennsylvania did you grow up? I went to school in Pittsburgh.

Jaimie Nawaday: Oh, I grew up in a small town outside of Allentown.

Khurram Naik: Okay, not so far away from Pittsburgh.

Jaimie Nawaday: Right.

Khurram Naik: Yeah, I think you're right. I think stories are what help people really change their minds. We are really, you know, most influenced by stories and not data, right?

Jaimie Nawaday: Right.

Khurram Naik: And in terms of, you know, you're already exercising skills that you already have from, you know, the public speaking skills are things that you already have. Are there—are there any other professional benefits that you see for yourself from pursuing this?

Jaimie Nawaday: Um, that's tough to say. I mean, potentially, right? I mean, apart from the obvious, somebody can pay me to come speak. But really I think it's a huge benefit to all of us if we start to change the legal industry and everybody feels a little more included and they don't have to stress about "How am I going to navigate this event?" And when I was at this recruiting event recently, some students told me that they've been secretly stressed out about how they're going to navigate the law firm world as a non-drinker. And they shouldn't—they shouldn't have to worry about that. I mean, there's enough stress that you deal with as a young lawyer, just, you know, the hours and whether I make a mistake and a privileged document goes out the door and all the things that you worry about as a junior associate. The last thing you should have to worry about is, "Are people going to—am I going to be held back in some way if people know I don't drink alcohol?" That's just—that's crazy.

Khurram Naik: I think what I really like about this, adding this to the conversation of legal practice, is because, you know, so many interviews you see in, you know, major media legal media publications or bar—you know, if you go to a bar association kind of interviews to do, it's, you know, fairly formulaic about the career decisions that somebody makes. And so it's just based on the analytical qualities of one option or another. Like you and I could—could jump in that right now. You and I can ask you, "Well, tell me about, you know, why you went to Seward & Kissel and tell me why you went to the US government." And those are definitely a key part of, of course, the career decisions we make is, you know, some analysis of the payoff we're doing right now talking about Disrupting Drinking: "What's the payoff?" So yes, these kinds of things are part of our careers for sure and helpful to share. Um, but what I like what you're doing is, you know, you've identified drinking as this nexus of all these different forces in law and all these different—so I mean, like why do we drink? We drink, you know, in key part to relieve the stress of the kinds of work we're doing. Okay, what—what is stressing you out? You just said, "Well, okay, like am I going to blow some privilege issue? Or, you know, am I going to…" You know, just like, "I—I'm—I'm really worried about this brief and there's only—there's only so much I can spend time on writing on it." And so it's a juncture point to say, "Okay, how are you practicing? Is there some other way that's better to practice? Is it inconceivable the only way to practice is pressure, pressure, pressure, do an amazing job?" Like there's got to be other ways that we can relate to each other and get excellent work, meaningful work. And so I think it is a useful touchstone to—to hit on a lot of areas of fulfillment and excellence in the practice. So I think there's… yeah, I think adding this will really be I think very enriching for just getting people to have conversations and take pressure off and figure out other solutions for what's really driving this behavior of drinking. Well, I think it would be helpful for a little context for your practice to understand how you got here. And—and of course, you know, talking about experiences you had with drinking could be relevant to that, too. Um, but I guess we can start with going into government. Could you talk a little bit about why you went to the US Attorney's Office? Like, what were your goals heading into this and—and talk about some of your experiences there? Because you mentioned—you mentioned in the context of drinking that was kind of a, you know, you felt like you're joining a new culture and, you know, wanted to fit in. Um, so tell me—tell me about that—that change, because you were already in private practice, exposed to that world, found a new world in government practice. Tell me about the differences that you saw between those two worlds even as an experienced litigator at that time.

Jaimie’s journey from barely middle class in central Pennsylvania to leading a BigLaw practice resonates with Patti Burris, who had two kids and an associate’s degree before she started the path to law school — and ended up at the top of her class.

Jaimie Nawaday: Yeah. Um, I guess I thought about—I'm not sure my early stage career choices were the most thoughtful. I think a lot of it was, right, opening up the Vault, looking at rankings, and then you know, somebody tells—you know, or having certain mentors who said, "Here's what you need to do, and you need to go to this type of firm, then you need to go to the US Attorney's Office, then you should make partner." And so I sort of marched through Law Review, clerkship, white-shoe firm. Um, then I decided I need to go to a different firm to get more kind of stand-up-and-argue experience. So I changed firms with the eye of going to the US Attorney's Office. And you know, some people have really great stories about why they chose to go to the US Attorney's Office. I think mine was less thoughtful. It was, "This is kind of what people who I respected had done and suggested I do." And it sounded really cool, and so I thought I would—I thought I would give it a try. And when I got there, I mean, it was—it did feel sort of like a dream come true getting the job. And I was just immediate, you know, you show up and you feel like you have so much responsibility right away. I started on the civil side. I was in the civil side and then I later moved over to the criminal division. But you start and you just have no idea what—how to do anything. I mean, you're assigned all these cases, you don't really know the first thing about kind of running your own case start to finish. I was a mid-level associate at a firm just before that, but you still, you know, you get very specialized in firms very quickly, you're kind of doing the same things over and over again. And suddenly you're kind kind of running the whole show. You're almost like a solo practitioner when you join the US Attorney's Office. And um, you know, the camaraderie's great, but I think one of the most stressful things at first is you go into court, the judges are very hard on you. They tend to defer to the government a lot. You have a lot of credibility when you walk into court, but the—the trade-off there is that they're holding your feet to the fire constantly and they feel like they—they have to. And so you feel, you know, inexperienced, a little bit bumbling, you get screamed at a lot by judges and—and it—it's hard, you know. I'd go back to my office and cry. I mean, every—every junior AUSA has that experience of walking into court, um, getting blasted for something or other. Maybe it wasn't even something that was their fault, but whatever it is, like the government is always responsible. You learn early on that you have to take responsibility for everything. And so there are a lot of very humbling moments, and then you go—go back to your office and you beat yourself up again and again and again, at least I did, and a lot of people do. And—and then you look for a way to kind of clear your head from all of that. And so we would have, you know, Scotch Fridays, we, you know, liquor cabinets or—file cabinets full of liquor. And we'd break it out and we'd tell stories and that was kind of the way of decompressing from the week, you know, telling the war stories from the week, telling the humiliations of the week, bucking each other up. Um, and—and in a way that's—that's kind of how the hard drinking started.

Khurram Naik: And then what was the experience of being in government that transformed you as litigator? Like, what was, you know, you went through this experience and you came out on the other side. What was different about Jaimie at the end of that experience compared to the beginning of the experience?

Jaimie Nawaday: What was different was, I would say, my first major trial when I was in government was so high stakes. It was a case against, um, it was a case against Bank of America. And it was before Judge Rakoff, who's known for moving cases very, very quickly. And it started as—as a qui tam, as a whistleblower case. And the government often gets a very long time to investigate whistleblower complaints, especially against a large financial institution, because you could imagine that takes—it could take years to do an investigation like that. I was given six months to investigate before I had to make a decision to either resolve the case or file suit. So six months of investigation, and then we filed suit against the bank and Judge Rakoff set the trial date for less than a year from the filing of the complaint, which is extraordinarily fast for a civil case of that size. And I later found out that we had—they were something like… we knew that the—that the team on the other side was large just based on the number of attorneys on the docket, but of course, there was an army of lawyers behind the attorneys on the docket as well. And so at our largest, we briefly expanded I think to five AUSAs on the case, but typically we had a three-to-four AUSA team. And we had roughly 100 lawyers on the defense side. And so we were, I mean, we were just unbelievably outgunned. We had this impossibly fast litigation schedule. And so there was absolutely no room for error, because we had numerous experts in the case. If an expert report were not done properly, if the sampling of the—the case dealt with defective loans, we had to sample loans and evaluate them—if the sample size was not drawn correctly, there would be no time to redo it given the pace of discovery and how quickly the trial was approaching. So I worked just the most grueling hours of my life for that really entire year period. And I—I just remember being nervous all the time because so many of the things that I was doing for that trial, I was doing for the very first time. And it was my very first trial. And I was against Brendan Sullivan, who is this, you know, he represented Oliver North in the '80s, he's this huge giant of the DC bar. And leading up to the trial, I was reading a book on trial techniques on the subway, like how to lay a foundation for a question. Like the basics of trial practice, and I thought, "This is so crazy." And this—not everyone at the US Attorney's Office has an experience like that, where it feels like you feel so inexperienced and you're against such experienced lawyers out of the gate. But you have this dramatic moment where you're like, "This is—this is how you grow up as a lawyer. This is how I became an adult lawyer, and this is when I developed the skills that carried me forward." And after that point, I felt like, "Okay, I can—I can do anything, I can learn anything." It might be scary, but I made it to the other end. We won the trial and it was a completely transformative year for me professionally.

Khurram Naik: Tell me some more about that because you enter, like so many lawyers, into government. You enter as an associate and you've come out as a partner. What is that transformation? Can you say some more about like, you know, it's—it's… I don't think it's as reducible to say like, "Hey, a mastery over the Federal Rules of Evidence" or something like that. Like, what is—is it some attitude in you, some—some perspective that, "Hey, like," I think you were just saying it, you know, that "I can—I can take on any problem"? That's some of it internally to you. And then what is it, you know, that firms in assessing you are looking to see to say, "Yes, you are in fact a partner"? You know, I'm sure it's not reducible to how many trials you had or just anything quantitative like that. What do you think is that quality or—or what do you think, apart from this trial, like what was the inflection point in you in terms of how you saw yourself and approach work? Is there something you can speak to that that's just different that somebody else can assess?

Jaimie Nawaday: Yeah, I think it's—I think a lot of it's just a confidence game. I mean, there's—there is a certain level of experience, skill set, obviously that's going to be a necessary component in that, but it's never sufficient for somebody to regard you as a partner, of course. I think it's really having that confidence and being able to inspire that confidence in others, where you can command a room and you can tell the client, "I can handle this for you. Here's what I propose to do. Here's the result I believe we can get," and you inspire that trust and confidence. I think that's—that's what firms look for in making a partner.

Khurram Naik: And then were you active in the white-collar bar as US Attorney, or did you get active in that after you became a partner?

Jaimie Nawaday: After I left.

Khurram Naik: Is that common? I don't—I don't know if it's common at all for US Attorneys to be part of white-collar events, or maybe they'll speak at them, but I'm not really familiar with—with the level of…

Jaimie Nawaday: Right, it's typically people in the defense bar, but they'll have sometimes some supervisors from the US Attorney's Office sometimes come and speak or attend select events. But they're—but they're not often there because a lot of times we're talking about the challenges of dealing with the government.

Khurram Naik: We had talked a little bit before about the white-collar bar and, you know, I practiced in a—in a pretty small bar, the Hatch-Waxman bar, which is like a subset of patent litigation. And so um, there's a lot of advantages to being in a specialist bar. Um, but I'm curious to spend a little more time on that because I think um, it was very interesting um to learn about the nature of the white-collar bar and the work. Um, I think it'd be exciting for a lot of people who are earlier or—or somewhere in the middle of their—of their experience to start thinking about how they fit into that. Um, so can you talk a little more about, you know, compared to your commercial litigation counterparts down the hall, you know, what are some of the differences that you've observed in the white-collar bar versus commercial litigation?

Jaimie Nawaday: The commercial litigation bar is just much, much larger. So I think you—they're fewer—you don't have the repeat player factor the way you do in a smaller bar like the white-collar bar. So your reputation just follows you much more easily in the white-collar bar. You have a lot of repeat players. Um, prosecutors will always ask, you know, if somebody come—when I was an AUSA and somebody calls me up and says, "I represent so-and-so, you know, can we talk about this case?" I would always look them up. I would see were they in the US Attorney's Office, I would ask my friends about them. "Do you know this person? How are they to deal with? Are they credible?" Right? You want to know is this—should I give this person a meeting? And if so, how much time should I give them? Are they going to try to play me? Are they going to be straight with me? That sort of thing. So your reputation really matters. You want to deal with people fairly because you are a repeat player with the government, with your fellow defense counsel in a joint defense group, things like that. You—the joint defense group only works if the fellow members of the group trust you to share information with you. And if they're sharing information with you, you can better advocate for your client, obviously. But in the commercial litigation context, I mean, sometimes you have joint defense agreements, but it's just such a sprawling bar that I think it's… you can get away with being sharp-elbowed um for a longer period of time.

Khurram Naik: Can you say some more about that dynamic of what it is that a—a white-collar lawyer can engage the government on to learn about, you know, and then what are some of the gamesmanship involved that you're looking to avoid? Tell me some more about that dynamic because I think that's, for people outside of white-collar practice, I think that's um kind of a black box. They don't really understand, "Like, what is there to learn?" You know, like for myself I only did commercial litigation, so there's a complaint, it's a publicly filed document unless it's, you know, there's something, you know, that needs to be redacted or whatever. Um, but broadly speaking, it's a public process and transparent in that way. So can you speak some more about, you know, what it is that these lawyers are looking to assess and—and tell me some more about how credibility and um reputation play in—in both among members of—of the—of the bar and then between the government.

Jaimie’s decision to launch Disrupting Drinking as a speaking venture — building a business around her authentic voice — is similar to what Sunny Kim did after quitting BigLaw. Sunny now teaches lawyers how to build personal brands by combining vulnerability and insight.

Jaimie Nawaday: Right. So especially if you are primarily doing investigations, which is what I do, so the whole game is to prevent somebody from getting charged. Because once your client is criminally charged, they already suffer—even if they go to trial and they prevail, right, they've already suffered so much reputational damage. And so that's really what especially white-collar defendants generally want to avoid is getting charged in the first place. But when you're at the investigation stage, there's no discovery that you can engage in. If you—it's such an information game and the only way you're going to get information out of the government at that stage is basically by having a relationship, having rapport, convincing them to just voluntarily share information with you. They don't have to share anything with you at all. So I can call them up and say, "I represent Jane Doe in this matter, you know, what—what can you tell me?" They might just say, "Well, you know, we can't really share anything at this point." And I can't—I can't force it. Then that's—that's where we are. I go back to my client, they're not going to be very happy. Like, "What do you mean? You can't—you can't tell me anything at all that they're looking at?" Or, it can be, "Well, Jaimie, let me tell you. We've, you know, we've spoken to a lot of people, we think your client's in a bad spot and here's why and blah, blah, blah," and share all this information with me um to just give me a sense of the strength of the case. And they can say—they can do what's called a reverse proffer where they call you in, especially if they want to resolve the matter in some way. Uh, they can call you in and basically share, you know, in detail the evidence against the client, which allows you to then consult with your client and make a much more informed decision. They can say, "All right, we'll do a reverse proffer and then we're happy to hear from you." Some sort of counter-presentation of why you think that we shouldn't charge. And again, they don't have to allow you to do that. They typically will allow that as a courtesy, especially if you are an alum of that US Attorney's office. It's sort of a professional courtesy that they would extend. But all of those little things, it's kind of um as, you know, just a system of—of courtesies that they don't have to allow, but they will allow if they think you're not going to abuse the process, if they think that you are a credible person um and you're not somehow going to twist it against them. So that's why all of those little things just—they really matter, especially if the government is pretty dug in and you want to go in and tell them, "I know you guys have spent a year on this case, but here's why you've got it all wrong and here's why you shouldn't charge." Right? Like, that's—that's a pretty big ask because, you know, there's sunk costs and all of that that—that might be at play at that point. Agents can be very dug in, even apart from how the AUSA feels about the case, and the agents can be pushing the AUSA really hard. So you just want everything that you can get that will allow for you to get additional information out of the government and for the government to give you a fair hearing before they make a charging decision.

Khurram Naik: What's the payoff to a US Attorney for sharing this information? So, you know, I'm in private practice, I'm looking for the government to share some information. How do I frame it for the benefit of the government to share that information?

Jaimie Nawaday: Um, if they're—I mean, for a responsible AUSA, they—they want to get it right, too. I mean, some people can just be hyper-aggressive and dug in no matter what. But generally, they want to get it right and they don't want to be embarrassed. They don't want to charge a case that's going to blow up in their faces. And so if they think you have something that will allow them to reach the right result, that's—that's in their interest, too. Right? The flip side, but, you know, cynically, I mean, sometimes they might want to know their weaknesses to see if they can then make their case stronger, which is why some people don't like to share a lot of information on the defense side with the government because their view is, "Look, they're—they're just—whatever holes I poke in their case, they're just going to plug through other means and then still bring the case."

Khurram Naik: Sure. Yeah, then the same commercial litigation analogy might be rather than deposing a witness and, you know, making clear like the reason—you're just inferring the fault lines that you're trying to establish for that witness, just examine them at trial to, you know, to show right then and there, "Here's the weaknesses with this person's credibility or theory."

Jaimie Nawaday: Right.

Khurram Naik: So then um, there—you know, so you—you return to private practice and um you're part of a small bar, but there certainly is competition among your peers. How do you differentiate yourself? So what—what has differentiated your approach compared to other peers with comparable experience?

Jaimie Nawaday: Hmm. I—I mean, I'm not sure I've ever done anything intentionally to sort of pitch in—in terms of as compared with my peers from the US Attorney's office. Like I can't think of a pitch where I've said, "Here's why you should hire me instead of so-and-so," you know, somebody else. And I don't—I don't tend to pitch in white-collar defense work anyway. Um, I think because I guess what I—what I've always said to clients is it's just a very personal choice. There are lots of excellent white-collar lawyers out there with very similar and—and I think this is true, with very similar backgrounds, right? There are lots—I mean, the US Attorney's office is a very big place. There are lots of us who come out every year with great credentials and I think ultimately the decision for a client is, "Do I feel comfortable with this person? Am I going to be able to share everything I need to share with this person so that they can really advise me? Do I trust their manner, demeanor, messaging that I think they can properly represent me and represent me the way I want to be represented?" Right? And for everybody, that's going to be different. Some people want a softer approach, somebody want—some people want like bulldog from start to finish. And that's just going to be a personality fit.

Khurram Naik: It sounds like that is highly unique to that—like I can't think of another practice that's so personal in that way. And it makes sense, right? Because so many of the people that are charged, you know, this is their liberty is at stake here, their credit, their reputation, which as we say, you know, even if a charge isn't proven, it just—it still has a stain. Um, and yeah, so it makes sense that it's an intensely personal process then. So um, I guess and that means that you're probably leaning in more to yourself and—and how you are as a person. You know, there's just probably such a nexus between your personality and your practice. So can you say some more about what is your personality then? When—when somebody is considering, you know, you mentioned maybe one person's a bulldog, one person isn't. Okay, those are different dimensions. What is it you think that people tend to be drawn to you and—and really resonate with you on?

Jaimie Nawaday: I think um, I think people find that I really listen to them. And I think that's—that's really important, that I will listen patiently to their account of what happened and think very, very hard about all the angles in terms of how to message to the government. And so I think people often want a lawyer who really listens and understands their perspective. Um, and I think that people find me earnest and credible and they expect that the government will view me the same way and that—and that judges view me that way as well, that I'm straightforward and candid and that that—that if the same things come out of my mouth that come out of someone else's mouth that might be a little bit less trustworthy or be regarded as a little bit less earnest, that obviously I—I can be a more effective advocate for them. But I would say it's—it's really just being myself, that they connect with the fact that—that I will listen to them, I will take their strategy ideas very seriously as well and I will package them as—as earnestly and effectively as I can.

Khurram Naik: I can tell that you do that from this conversation because if I ask you a question, you'll pause, you heard me, you're thinking about it, and then—and then you're willing to say, "Oh, I hadn't thought about me some aspect of this" or whatever. So that really tells me you are listening to me. So yeah, I—I find that effective. You mentioned storytelling, um, and so I'm thinking of I—I did another podcast interview with Neil Chatterjee, who's a patent litigator, um, he's had a number of jury trials. And so he's been on both sides of the V in patent litigation. And he says, "No matter what side of the V that I'm on, um, my position is that we are always representing the innovator. Like, we are always going to tell a story about how we are the innovator here." And so are there principles of storytelling that you have for your clients that—so that's a story that maybe a jury would find persuasive: "Like, okay yes, that's the innovator and that's relevant for this legal cause of action." Are there patterns of stories that you find helpful for the government for um persuasively, you know, seeing your—your client in a beneficial way?

Jaimie Nawaday: Um… yeah, I—I mean, there are. I'm sort of hesitating to say it because I think, "Well, if somebody from the government hears this, are they going to think then this is—this is somehow a ploy? This is just her pattern." But I would say I have had a number of cases in recent years where I was—I was advancing a theory and a message that on its face would seem quite far-fetched. Um, where it was—it was essentially a version of the "you've just got it all wrong. The person you're looking at as the target is really the victim here." Some version of that story. But I 100 percent believed that that is what happened. And I had success in turning the government's view based on just building, you know, receipt by receipt why that was the case. And it took some time. But I would say even though it was sort of a seemingly preposterous theory to advance to the government, right, to tell them, you know, when they think they're rarely wrong, "Like, you've got it all wrong and you have the wrong—you have target and victim in the wrong buckets here," uh, that would also be something that would be very embarrassing to get wrong to the government. And so I think in those cases, my credibility really helped that I got any kind of hearing at all in those cases.

Khurram Naik: You know, it also seems to me that, you know, reflecting now on the nature of your work and how much it is about doubling down on your persuasiveness and authenticity, it just seems like in that context it almost seems obvious, Disrupting Drinking. Because I mean, just like that is just, you know, you by profession are somebody who deeply personalizes stories and contextualizes and says, "Hey, this is a real person's life at stake here," and then um helping the government understand what's at stake for this person and—and what they—what they did or didn't do. Um, so that sense, like these like hyper-personal stories that are persuasive, like it just—it just seems, well obviously that—that would be helpful for you to do that in other contexts too. So just, do you see a connection between your approach to work and how you're thinking about communicating through Disrupting Drinking?

The fear and imposter syndrome Jaimie describes — adopting drinking norms because she felt like she didn’t belong — connects to Hilary Gerzhoy’s core observation that fear, not greed, drives most professional missteps among lawyers.

Jaimie Nawaday: Yes, yes. I'm not sure I did before you said that, but I think I think that's sort of… yeah, I mean—I mean, now that you've said that, I think that's almost a theme through my life, sort of stories that I grew up on that really impacted me or just sort of the power of storytelling through my childhood. Because um, my parents—I grew up in a pretty religious household, and so you know, my parents really wanted us to read the Bible and stuff like that. There was, you know, church every Sunday, so I had sort of that world of Bible stories. On the other hand, my father was really into pro wrestling. So I grew up really on like the stories of the Bible and the pro wrestling, right? And in some ways, like both of those kind of came together in my trial work, too. Sort of the concept of showmanship and the good versus evil narratives and all of that. And I think—but I think that's sort of the power of storytelling, as I'm reflecting on it, that's—that's been kind of a theme of my life.

Khurram Naik: I was just picturing in my head like, and then Vince McMahon the begat, and then just, you know, going through that list of begats for that family. Um, yeah, that's—uh, yeah, I think um… so I guess I'm curious now, in this stage of your career, what story about yourself—it sounds like historically you've challenged stories about yourself or the stories that you accepted from the world. Um, can you share some of those stories that you challenged over time? Like, what were some of the stories about yourself and how you fit in that you challenged? You mentioned, you know, in terms of fit, fitting into, "Hey, like I'm now in the world of big law as a summer associate," so so maybe there's some stories there, um, and then some stories that you had for yourself, you know, heading into the US Attorney's office and making sense there. Is there—are there in these different eras of your life, can you think of stories in the past that you challenged then found a—a new story on the other side of that?

Jaimie Nawaday: Yeah, I mean, I think—I think the biggest one was I grew up um just temperamentally I'm very shy and introverted. Or—or was, growing up. And some of that has faded over time, but you know, I just would—I just avoided public speaking wherever I could growing up and—and really through college, you know, dropping classes that required speaking or trying to skip if it—if it was a high participation class. And even—even early in my, you know, I tried to kind of fight through it in—in law school, tried to participate and things like that. But because I sort of had this feeling that I could be good at trial work, but I was just was so petrified of public speaking. And I would, you know, battle just not just nerves, but like nausea and nightmares and, you know, really felt kind of phobic about public speaking. And when I was a junior associate and we had a mock trial exercise at my first law firm, and my partner mentor said, "You should—you should really do this, it would be great for you." And I said, "Okay, I'm going to do this." And then I just got so wound up with nerves that I just sort of told the program organizer, "I can't do it. I'll do it next year," whatever, I made up some excuse, "I'm too busy," and just sort of dropped out of it. And I could tell my partner mentor was disappointed and I thought, "All right, well, I guess that's it, you know, I'll never be a trial lawyer, I'll never go to the US Attorney's office," and I just thought, "I'll just be a quiet behind-the-desk lawyer, I guess that's—that's what I'm meant to do." And then I don't know, and then I—I can't really think of a clear pivot point, but I just decided, "You know, well what if I just—what if I just did it anyway? What if I just kind of got over it? What if I just applied and did it little by little?" And of course, you know, that's—that's all it takes. And the first time I did an oral argument, I was up most of the night with nausea and was, you know, worried about my voice shaking in court and all that. But I got through it and the adrenaline on the back end was so great that it sort of made all the nerves worth it. And I think that's when I then started to get hooked on, "Okay, I'm—even though I'm much more outgoing now than I was as a kid, I, you know, everybody battles nerves with public speaking, but I—I guess I just—I see the reward. I see the reward both in terms of connecting with the audience and how meaningful that can be, whether it's jury or law students or whoever, but also just that—that excitement and that adrenaline on the back end is so, so satisfying."

Khurram Naik: You know, it's interesting because I also have always historically, I have thought of myself as being very introverted, and through—I just—I was just talking to my wife this weekend about how funny a profession I've chosen as a legal recruiter, because um, I—I'm on phone calls all day. As a litigator, I'd just be—I'd have my door shut mostly and just be working on whatever discovery issues or briefs or whatever, just it was very solitary. I enjoyed connection through, you know, bar associations and that kind of stuff, um, but I was uh very solitary historically and not—didn't have any training beyond tons of phone calls. So I'm just on tons of phone calls all the time and it's um and it's intensely social in that way in a way that um I—I don't consider myself to be an extroverted person who um… and then you know, my role also involves um persuasion, uh sales. And so that also is—is… I'm not natural to those things at all. I'm not like a charisma-driven person who just naturally is, "Oh, of course, that person's in that function." So um, I—I have also had to—to work, I've chosen to—to work inside, but I'm really proud of myself for doing that. Um, and it's funny because you mentioned connection with your audience, and that's a really interesting takeaway from public speaking because it could be very surprising to think that, right? It's a very distant experience where there's a public speaker, audience, and there's a very separateness, and you're speaking to this general large room and your voice is booming and it's just—it's a one-way street largely. Um, but I, you know, in my history going back to say even high school, I found that even though I was and then way more introverted, I have always enjoyed public speaking because of what you just described, is that intimacy. And so I should also add like, hosting podcasts, this is a one-on-one conversation. This is like probably my favorite, two or three people is like my favorite format for communicating, uh for really understanding other people. And but yeah, I've found that public speaking is a surprisingly good way to do that at scale where um it wouldn't seem obvious that an introvert could really enjoy public speaking, but I—I think that's what you're communicating, that you've experienced that as well.

Jaimie Nawaday: Right. Yeah, because you're talking really to a bunch of individuals at the end of the day when you're in the moment in public speaking. And what you look for is that—that recognition on someone's face when they go, "Oh," you know, when you see a little bit of an emotional shift in them or something resonating, and it's—and it is like you're back having a one-on-one conversation.

Khurram Naik: So we're talking about stories and—and how we challenge those stories over time. So today, what is the story about yourself that you're challenging?

Jaimie Nawaday: Hmm. I guess that I'm not exactly sure how to frame it, but I think as lawyers we're very often safety seekers and sort of, you know, reputationally conservative and all that, sort of concerned what the market will think, what people will think, all—all of those sorts of concerns. Um, and I feel like I've—I've sort of dropped that, and I kind of had to drop that in order to do this whole project. And some of it was just—it just sort of felt like the next chapter of my life. And I've been listening a lot to—I don't know how I got into this—but I started reading and listening to death doulas, who are just like birth doulas but they, you know, they guide people basically in hospice who are getting, you know, are very near death. And they're very positive people and they have all these great life lessons about, you know, what people say at the end of—of life and what their top regrets are and things like that. And one of the top regrets that comes up again and again that this one death doula mentioned is that people say, "You know, I just wish I hadn't cared so much what everyone thought." You know, I cared so much what other people thought and I was never authentic as a result. And—and I think as lawyers, it's—it's very easy to be like that. We're in such a conservative profession and it's not like I've just thrown caution to the wind or I don't care what anybody thinks, but when faced with a choice of "I can do this thing and maybe there—there will be some reputational blowback," but there really A) shouldn't be, and B) whatever is the blowback to me, I am 100 percent certain that this can help other people. And so I'm going to make the choice to help other people. And I don't know that I mean in—and I have a certain amount of luxury, I'm at a point in my career where I can do that too. You can't ask somebody who's up for partner to make the same choice. It's just not realistic. But if those of us who are sort of in leadership positions now in firms can't do that, can't share these kind of stories, then who can in the profession? Really no one. You know, do we have to wait until we retire to tell these kind of stories? That seems really unfortunate and doesn't send the right message. I want to be able to say, "You can share this story and the world, you know, an anvil won't fall on your head, your clients won't run out the door, everything's fine. We can have these conversations and it's so beneficial to the industry."

Khurram Naik: Yeah, I really like that. I think the North Star of, "Hey, as long as I'm being helpful, there really can't be any risk in that," is—is a great message. And then I also think it's a great message that um this can be this incremental approach, this isn't—this isn't all or nothing. Um, and yeah, I think, you know, in your role, it could cut in both directions where people could feel they have a lot to lose now. "Like, hey like, now I've worked—I worked so hard to become partner, and now this is the thing I have to lose." So I actually think you deserve um recognition for that, that you are—you are taking this step in a phase where others would actually I think um could choose or—or maybe we've even observed choose to—to be more conservative about it. Um, yeah, I felt for myself, you know, I went to a law school that uh Big Law recruits out of and I ended up in Big Law and always felt for myself that was such a blessing for me because I didn't have the attachment to that identity uh that other of my peers… Like if I went to Harvard or Yale, I—I could imagine all the pressure I'd be putting on myself based on my peers, based on my perception of myself to say, "Hey, why did you do that thing? Why did you achieve that credential? It was to—for this narrow set of options for you." And so um, yeah, I think there's a lot of of um gratification for removing identity. Um, there's a—a writer and investor Paul Graham who—who talks about, he's got a great essay, I think the title of the essay is "Keep Your Identity Small." And uh haven't read it in a while, but I—that's my recollection and takeaway of it is, is the fewer things that you um connect yourself to… Um, I think Bruce Lee also talked about this in Jeet Kune Do. I think that's the—the empty fist he's referring to is if you've got a knife in your hand, you do knife things with it, but if you have an empty hand, you can do anything with it. Um, and so on that topic, I saw that you are also part of a board for wrestling. I think it's encouraging women to wrestle. Can you—can you talk some more about that? Because that also seems pretty iconoclastic, um, and uh tell me some more about your—your role in that in—in your advocacy for—for women's wrestling.

Jaimie Nawaday: Yeah. Um, so I—I mean, I love strength building overall for women. I just find it very physically empowering and I like lifting weights and have tried since I quit drinking, did different um like a—kind of women's fight camp in DC and some Krav Maga and stuff like that. And—and raised my daughters in CrossFit for a while and then we—we tried different sports, but I think that gave them some early strength and confidence. And my older daughter was having—she was like 13, 14 during COVID and was having a pretty tough time like a lot of teen girls were. And initially I got her some—she had mentioned before COVID about trying boxing lessons. And so I got her some boxing lessons with a female trainer and she very quickly like I noticed a—a change in her after just a couple lessons. It seemed to really be pulling her out of, you know, some of what was bothering her during COVID. And then when she started high school, I encouraged her to try out for the wrestling team. And—and she got on and it completely transformed her. I mean, she—she had some talent in it, but she loved just this crew of women who were all, you know, obviously all different body shapes and sizes because you have all these different weight classes. So it sends the message of "you can be strong and powerful and athletic in a variety of sizes, not everybody's trying to be 100 pounds or 110 pounds." Um, she's, you know, taking pride in her big strong legs and stuff like that. She's not, you know, when I was growing up in the '80s everybody wanted to have like thin thighs and stuff like that, and this was a whole different mindset that I thought was so positive. And she just changed, you know, just the way she moved through the world was different. She just started moving through the world with such confidence. And so my younger daughter who's now a sophomore in high school, she ended up when she got into high school trying out for wrestling as well and had the same experience with it. And I've just—I've just watched it, the effect it's had on both of my daughters who were also super shy and introverted just like I was, like really take on this both physical and social confidence that they didn't have before. And the wrestling, the girls' wrestling community is just—it's just an incredibly empowering place. You know, it's like there's so much nonsense that teen girls have to deal with in terms of, you know, looking a certain way or whatever, and I feel like wrestling is such a great antidote for that and such a confidence builder. So um, so I got involved with Beat the Streets, which is a um it's a nationwide organization. I'm involved with the New York chapter and it—it's basically a free wrestling club um for um middle school and high school wrestlers around the city. And they have just fantastic coaches and a fantastic community and that's why I wanted to be involved with it.

Khurram Naik: Yeah, I guess what—first thing I thought about, I mean, it's obvious because we're talking about a handful of things so I'm going to connect it to other things you're talking about. But I—I'd also be curious there if there's some connection between your experience with that organization, which is taking a new message for a group of people to say, "Hey, like, you know, maybe historically women have not been in wrestling, but hey, this is really beneficial for all these different reasons for how it influences how women, girls think of themselves." Um, that, you know, maybe you just at least tacitly got, "Hey, there's new ideas and new ways that we can present um new ways to relate to each other in these communities that are about uh improving ourselves" that, you know, maybe had some foundation for you for—for for ideas in this in Disrupting Drinking.

Jaimie Nawaday: Right. Can you say that again?

Khurram Naik: Well, it's possible that, you know, picking up ideas for new ways for people to relate to each other in this one community where just the benefit was pretty clear, but it's a new story. It's a new story for women in wrestling, so that's a relatively new story. That there's ideas from there that's influenced you to say, "Hey, you know, maybe there's new stories in my practice that I can share and help people relate to each other a little bit differently."

Jaimie Nawaday: Yeah. And I mean, I—to be honest, I also am just super inspired by—by watching them wrestle and watching these girls wrestle in general. Whenever I feel nervous about something, I often think about it. I think, you know, what—whatever, whether it's starting Disrupting Drinking, sharing my story and "Oh well, what will people think and what—what might be the fallout," and I think about my kids just stepping in this circle for physical combat about somebody and they often wrestle boys too, you know, somebody who is bigger and stronger than they are and knowing, "I—I'm probably going to lose. I'm probably going to get pinned" or whatever in front of all these people, but I'm just going to fight my heart out no matter what. Like, that's—that's incredible. And that's so moving to me. And I think, "Yeah, I can—I can take this risk."

Khurram Naik: Yeah, no one's coming for me physically.

Jaimie Nawaday: Yes, much, much less at stake. Uh, not getting pinned in front of other people.

Khurram Naik: Right. Well, Jaimie, thanks for coming to share your story. Uh, it's really—it's really admirable what you're doing. I think it's very interesting, I think it's very compelling and uh it's early days for you, so it—I'm really excited to see where you take this and where else you take uh your story in your career.

Jaimie Nawaday: Thanks for having me.