In this Unemployable Podcast episode, host Jeff Dudan interviews Rashmi Airan, a former high‑achieving attorney, Wall Street professional, and real‑estate closing specialist who later became a serial entrepreneur, law professor, vocalist, and transformation expert. Rashmi recounts her journey from an Indian‑immigrant family with Ivy‑League expectations, through a demanding legal career and a rapid rise as a solo real‑estate closing practitioner. In 2007 she secured a lucrative developer client, performed roughly 200 closings in 15 months, and ignored gut warnings about the legality of the developer’s “rental guarantee” incentives. After the partnership ended, the FBI investigated her, conducting a four‑hour interview without her attorney present, leading to a grand‑jury subpoena and ultimately a guilty plea. Rashmi describes the emotional toll of becoming a felon, the feeling of being exposed, and the lessons she has distilled about high‑pressure decision‑making, ethical blind spots, and the importance of systematic mental frameworks for leaders. The conversation also touches on the pitfalls of tax‑law complexity, the myth that ignorance is a defense, and the broader cultural pressures that drive high‑performers to take risky shortcuts. Rashmi now focuses on teaching leaders how to recognize and navigate such pressures to avoid legal and ethical missteps.
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I made the very difficult decision of pleading guilty. At the time, it was like the hardest thing I've ever done. 'Cause I, I was like in fighting mode, you know? And my whole life I was this perfect little Indian girl who never colored outside the lines. And I had this path set out for my life like this. I, I was like the good girl. Now all of a sudden I'm in a place where I'm now pleading to be a felon for the rest of my life. And like, I remember one of my friends said, Rashmi, you stood naked and exposed for the entire world to judge you.
Hey everybody, welcome back to the Unemployable Podcast. I'm Jeff Dudan. If you are a former attorney and Wall Street investment banker who served time in prison as a result of activities connected to real estate closings and are now a serial entrepreneur, law school professor, professionally trained vocalist, and globally recognized transformation expert, your name can only be Rashmi Arun. Welcome.
Thanks, Jeff. Thank you for having me. I'm psyched to be here, and I, I have so much respect for you.
Well, I appreciate that. It's been a minute since we've been together, and, uh, I really look forward to catching up with you. We, we've been together at several events over the years, uh, where I was fortunate enough to see you speak and get to know a little bit about your story. Here's my opener today: can someone have absolutely no idea they are doing something wrong and still go to prison?
Yes.
That's the short answer.
That's the short answer. Honestly, Jeff, I feel like we are in a world of, um, every leader facing so much of an onslaught and barrage of information, whether it's from AI, cybersecurity alerts, market volatility, global uncertainty and unrest. You know, talent shortages. We're just in the midst of so much coming at us all the time in pressure and urgency and speed. And in those moments, I think every one of us as leaders at home, at work, in our communities is prone and could possibly make a quick, convenient decision without thinking through the consequences of what those decisions could be. And so, like, so much of my research and work now is in this space because once we can get clarity and awareness, on how to make those better decisions, like what's the mental process we can go through, then we can all have a better roadmap so we don't end up like I did. But it is very easy, and you know, but for the grace of God, there go I is what I always say, right? Like on any given day, any one of us could do something that is currently illegal or unethical, or 7 years later could be found to be, and then they come back to you. So, there's just so many, iterations of what this looks like.
So, yeah, the thing I think about is tax fraud. And you think about Willie Nelson or was it Denzel Washington? I hope— hopefully I got those names right or else there's a claim coming for defamation. But people who, you know, I know that there's been celebrities and there's been people that have made lots of money performing in different states and doing all this. And if you don't have really sophisticated tax people around you, then all of a sudden you get in trouble and you had no idea that the taxes either weren't getting paid. You're not getting those notices. You've got a, you've got a business office, you've got a business manager, but at the end of the day, you're the one that is responsible and accountable if something doesn't get done right under your name.
Yeah, that's a great example. I think, I think the, um, also I think there's another version of that, right? Our tax codes and tax laws keep changing. And so, it could be that you think you are following the law, or your team believes that they are, something changes, they're not paying attention, they're not staying on top of any sort of like, you know, new laws that are passed, and then now all of a sudden you continue to do status quo, or like what you are used to, and all of a sudden that thing is not legal anymore. And so, like, then you get caught in this like issue, well, ignorance is not a in a defense. So then what do you do?
Right, right. Rashmi, you grew up in a, in a family where excellence was expected and high standards. Undergraduate UNC, Cornell Law School, graduating top of your class. You went to Wall Street. Oh geez, Columbia. Started with a C.
Okay, let's get the right Ivy League.
Yeah, well, thank you for correcting me on that. It's, you know, I, the, I never, closest I got to Ivy was, you know, I was working as a landscaper.
But—
It's important, Ivy. But—
You know, look, I, as an Indian immigrant, a daughter of Indian immigrants, like the goal of like, oh, I have to get into an Ivy League, I think is very common for for not just Indian immigrants, I think for first-generation immigrants, but also just high achievers, type A, right? We, we begin to define ourselves by these metrics and is absolutely was how I was raised. And so it was certainly a goal of mine. Although having gone through these life experiences, I am the first one to tell my kids as well as others, I think it's awesome to have the education. I'm very proud of being a Columbia alum, but I just think education in general is important. Important. I really think as long as you as an individual are focused and committed and study and are intentional and not just like flying by, that's what matters, right? You know, the, yeah, the pedigree is great, but it's not needed and essential.
Yeah. Then you had a career on Wall Street, then you went into private practice with your own law firm and you were doing real estate closings. Walk us through, if you can, your story and what happened to you?
Yeah, so I graduated law school and ended up in California actually first working for a big law firm. Ended up back in Miami, worked for a big law firm. Then I worked for the government as a government attorney, and eventually I started my own practice. Uh, it was, it was, uh, let's say mid-2004, and I was pounding the pavement. My husband at the time was a firefighter. We ended up having 2 little children. And so in 2007, when my kids were 2 and 3, I had the chance to meet a real estate developer. And so, if you can just sort of take yourselves back to 2007, right? The heyday of real estate. I live in South Florida in Miami, so it was like insane here in the market. And I had—
Oh, I was get— I was getting loans I didn't even apply for.
Well, okay. So, this— so, you're speaking directly to what I, what was happening, right? Yeah. So, I, um, at the time I was doing, I was a small solo entrepreneur, you know, solopreneur, running a business of about 5 people, and I was in the process of like constantly hustling. So imagine like being in a state, I'm a young mother, my kids are 2 and 3, you know, my husband is here and there, you know, in and outta the firehouse. And I'm like running around every possible dinner event and networking event and selling my services at the gym and like every possible place. I was like in that speed moment running around the racecourse of life trying to get to the next client. Trying to get the next client to be like, to book me or to use me. And, and in that context, in 2007, I had the chance to meet a real estate developer. So in my mind, what's happening is, oh God, if I can get this one client, it's like, it was like a light bulb, right? Like, oh, that's like the answer to all my problems. I'm gonna have financial stability. I'm gonna have, um, you know, essentially at the end of the day, more time with my kids. And that's how I saw it. And so, I kind of jumped, I like jumped at the opportunity. I was like, okay, I'm gonna, internally what was happening was, I'm gonna do everything I can and I hope that I wow this guy enough that he wants to use me. So, I go, long story short, I met with his two operations guys. They began to describe creative transactions that they were doing and they were creative. And I think there's this part of me not think, I know there was this part of me that was like, oh, I'm strategic and aggressive and I'm a bold out-of-the-box thinker. I, I can do creative things. Like I'm smart enough to do creative things. And so as he began to describe the scenario of what he was doing, which was essentially he was giving a buyer rental guarantee. So it was a buyer incentive to move his condominium conversion units. And I wanted this client so badly. Like I didn't ask the questions that I should have asked. First and foremost is why are you leaving your big law firm that you've been working with for 2 years, right? Instead, what was going on in my head was, oh, I'm special. There's something smart about me. I'm, you know, it was very arrogant, honestly, for me to be thinking that way. 'Cause I, I just assumed that there was something special about me versus, oh, he actually just wants something. So I ended up doing 200 closings for this client in about 15 months. I didn't ask for help. I didn't ask for a second opinion. I didn't look around and say, you know, this doesn't feel right. Like my gut was screaming and I just was not listening cuz something felt off. There were moments that kept happening and instead of questioning, I just pushed down that feeling, you know, like that gut feeling. And I stopped working with him in 2000, uh, uh, 2009, early 2009. And then I went to, I went into private practice with my father, merged my practice with my dad's. And essentially a couple years later, the FBI knocked on my door and they grilled me. I didn't have an attorney. I let them in and like, I should know better. I should know that don't talk to the FBI without an attorney. But it's like human nature takes over and human nature says, well, I didn't do anything wrong, so I should talk to the FBI. Otherwise, they're gonna definitely think I did something wrong. And so, I let them in, they talked to me, they grilled me for 4 hours. So, they were, like, showing me documents and emails and, like, all of these things. And I didn't recognize the reach of the federal government and how important that moment was for me because I did end up, like, prejudicing myself because I, like, instead of saying, I don't remember, I was saying yes, no without recognizing it. And so, Like, did you ever see this email? Did you ever meet this person? Right? Instead of stopping to think, I was answering again in the speed of the moment.
Yeah.
Um, so when they left, I thought that was over. I was like, oh, I'm, I'm the records custodian. I have all the files. That's all they want. Then 2 more years go by and I get a grand jury subpoena for documents. So I'm still operating with the pretense that I haven't done anything wrong, right? Like they just want, They just want my documents. Within 3 months, my attorney called me into his office and he said, Rashmi, you're a target. Which, by the way, I did not know what that meant. I, you know, I'm like,
