The Art of Career Reinvention with Gregg Schoenberg

Hello everybody. Welcome to another episode of Studying Law Around the World. Today I have the opportunity to be interviewing Greg Schoenberg. Today we'll be discussing a few different topics. In these last couple of episodes, I was given the satisfaction to interview a few professionals that are not lawyers themselves, but they work with lawyers and they have quite a few, you know, good pieces of advice and all of that. So I'm very happy to be able to interview Greg today. Thank you so much for taking the time to be with us today, Greg. Thank you so much, Claudio. And to just build off your point, let me disclose upfront that I am married to a lawyer. So while not a lawyer myself, I am very fond of lawyers. Amazing. And to start up our episode today, I'd love to ask you to share a little bit about your personal journey and also what kind of experience shaped you into the professional path you're currently in. So I have been fortunate enough to have 7 different significant chapters of my career. I started out working on Capitol Hill for a US senator. by the name of Bill Bradley from my home state. And after that, I spent a little bit of time as a corporate lobbyist where I learned how Washington really works or doesn't work, as the case may be. And proceeded to go back to business school and then became a capital markets banker for 13 years. Spent a lot of time taking companies public and advising companies and the like. And at the same time that I was doing that, there was a sort of a gnawing feeling that I had towards the 11th or 12th year of it that I was not meant to spend the rest of my career as an investment banker. So I left Wall Street without a plan and ultimately found my way into the fintech space. At the time that I was getting involved in fintech, people thought fintech meant technology from Finland. But, you know, I got lucky in terms of the timing. I built a startup in the fintech media space, which I was fortunate enough to sell. I then proceeded to become an angel investor. I got into various crypto-based projects and generally my timing was pretty good, not perfect, but pretty good. And it was through the process of being an angel investor that I discovered that I really enjoyed coaching executives even more so than investing in their companies. And so that's what ultimately led me to the insight that I should become an executive coach. Amazing. So, Greg, it sounds like throughout all your profession, you must have interacted with lawyers quite a bit other than at home, I would guess, you know, in Wall Street and then in the fintech environment. Was that the case for the most part, or were most of your roles very kind of like isolated from the legal world? Oh no, very much so. You know, when I was on the Hill, you know, there are more lawyers certainly than would-be financial types like me. And then as a corporate lobbyist, you know, maybe greater than 50% of all the people for the company that I worked for were lawyers. And then as an investment banker, of course, investment banks have big legal departments. The 2008 great— oh no, the 2000 tech bubble burst. I remember having to bring a lawyer into every discussion I would have with a research analyst. So I used to refer to the lawyers as the police officers to make sure that as the banker, I wasn't putting undue pressure on the analyst to issue positive ratings for the companies that I was seeking to get business from. And yeah, I mean, throughout my entire career, both, you know, as an angel investor, an entrepreneur, I have I work closely with lawyers and, you know, generally speaking, believe that when entrepreneurs, business people ignore their legal guidance, it typically comes back to haunt them. So I know better than that. That's awesome. That's awesome. And considering this career path you've gone through, you know, considering Wall Street, The Hill, fintech, and now career coaching as well, what would you say was the biggest turning point that led you to where you are today? Oh, I never was the type who had kind of like the aha moment. It was much more that, you know, I would feel something gnawing inside. Like when I was on Wall Street, the first several years were great, but, you know, as I got deeper into my Wall Street career, I kind of just felt like I was ready for something new. And, you know, when you have that gnawing feeling, you can kind of push it away and ignore it. But for me, I have always been attentive to the fact that, you know, I need to listen to my gut. And for me, a career is about not doing one thing really, really well, but doing a bunch of things hopefully reasonably well. Amazing. That's awesome. That's awesome. Was there a specific moment that drove you to realize that you needed to reinvent yourself or that you wanted to go towards another point? You just said something about like an internal feeling, but can I hear a little more about like what's been driving those decisions for you? Yeah. I mean, the, for me, I've always been afraid of not being excited about getting up in the morning. To me, there is just nothing worse than to devote all of this time and energy to a career that doesn't excite you. And so, I have always been very attuned to those feelings. And so, as an example, when I was an angel investor and I found myself thinking, you know, I really don't want to invest in this company, but I really like the CEO. And if I put a little money into their company, maybe I'll be able to have a weekly call with them where I can give them some guidance and coaching. And so, you know, I listened to what I was saying. And I'm like, wait a minute, why, why am I writing checks when that's really not what turns me on? Why am I not doing the thing officially that I enjoy doing unofficially? And so as I started asking myself that question, it became an obvious decision for me to move on, get trained and become a coach. Fantastic. That's awesome. Greg, I know you have a channel on YouTube, you've been, you know, producing content as well. And recently you shared a video on Sun Tzu's Art of War book, specifically about the death ground strategy. And it was so fascinating. I'd like to recommend everybody to check it out. It's super short, but the message is so good. And I think it applies to a lot of people, you know, getting out of college, even thinking about, you know, young lawyers specifically. If I may ask you, like, can you tell us a little more about like what the strategy is about and the concept that how could they use that in their lives? Absolutely. So I'll assume that you have a very smart listenership. I'll assume that everybody knows who Sun Tzu was, The Art of War, a brilliant strategist. Sun Tzu was incredibly good at understanding human nature. That was one of the reasons why he was such a brilliant general. And I've applied it to my own career and particularly for people who are in finance, law, and consulting in the following way. You may not notice it, but many people in these fields can gradually find themselves enveloped in what I'll call a gilded cage. And I'll give you an example of what I mean by that. Let's say you're a lawyer at a big corporate law firm. You're working your butt off, you're doing very well, and you decide, you know what, you're going to take your family to Anguilla for the holidays, and you justify that. By saying it's a one-off thing, it'll be expensive, but you know who doesn't like going to Anguilla? You go to Anguilla, you bring your spouse, you bring your kids, and your kids wind up bonding with the staff at the hotel. They become like a second family. Next thing you know, your kids are asking you to come back to this very expensive hotel in Anguilla the next year. Nobody likes to disappoint their kids, and so before you know it, voilà. You are in a gilded cage where you have now committed to spending a ton of money per year on a holiday that you never intended to have become an annual event. And I link that to the death ground strategy because, you know, to, to borrow the words from, or the title of a famous Pink Floyd song, Comfortably Numb, there are a lot of careers that you can become very comfortable in and allow your expenses to sort of meet or exceed the pace of the growth of your income. And when you do that, you are imprisoned and you can't leave even if you want to. So the death ground strategy for me is about having a different mindset. It's about having a mindset where you think to yourself, there is absolutely no way I can stay doing what I'm doing now because I'm miserable at it, and I am going to make sure to not allow myself to be bound by economic obligations that would ever prevent me from leaving. So as long as you have the ability to leave, you force yourself to do it. And when you have a mountain behind you or a river behind you, an army has no place to go but forward. You want to have that mindset if you're really serious about leaving your job. and you do not want to take that very fancy trip to Anguilla, absolutely, positively don't do it. I like that. And it makes me think of careers, right? So kind of following up on that then, to some extent, I feel like professionals in different areas might feel stuck. If I may mention quickly, it happens that I know a lot of legal professionals here in Canada who are internationally trained, but up until right now, they decided not to become a lawyer in Canada, for example, right? But it also happens on internationally trained lawyers that became lawyers here and maybe might not want to do that anymore. I don't know. I feel like that, that can apply just to so many different career paths. But after all, after all of this context or information in general, I feel like we could say that there's a reasonable amount of legal professionals that feel stuck, whether inside the profession, outside of it, trying to leave. the profession or just to leave the office they work for right now. So whether it's a job, practice area, what would be a meaningful step that, that people in general or legal professionals in general could take towards reinvention? Well, look, let me just say upfront that every reinvention is a snowflake, which is to say everyone is unique and different, but there are a couple of principles that I tell my clients to consider following. Number one, you have to do things differently if you want to become a different version of yourself, right? If you want to get into crypto as an example, a space that I know a fair bit about, if you want to get into crypto, you don't hang out at the veranda of the yacht club. You know, you need to go where you can find like-minded people because it's not enough to read about crypto in the Financial Times or the Wall Street Journal and think you're ready to reinvent yourself. As a crypto lawyer, that would be one example. So yes, you have to read different things and take in different inputs. And I think most importantly, if you want to make a switch, if you want to become a new version of yourself, you have to get your hands dirty. You know, I am a big believer in engaging in small stakes experiments. So it's not about saying, I wish I could do X, Y, and Z with my career as you look out the window of your office. And you don't actually do anything to put your body into those environments where you can try it out. You know, I once told a, or I once had a client who wanted to get into AI. This client was not a lawyer, but the point remains. And he told me about an interview that he had for an AI firm and how excited he was and how he read all of these articles all weekend. And I was like, that's good, but how much AI have you actually messed around with? And the answer was, well, no, I haven't really. I just sort of read about it. That is not an acceptable way to reinvent yourself in my view. Well, that does highlight a great point, you know, like having some kind of practice. I love that. It does help a lot other than just reading, you know, third-party experiences. And in your career, I'm sure you must have seen it a couple of times and now in your current coaching profession as well, would there be a few, you know, common mistakes that people make when they're trying to pivot inside their careers or, you know, going into another area? Is there any kind of thing that you notice that sometimes could be a common mistake? Yeah, I want to answer that question in general and then offer up a specific observation for lawyers. So I'm going to first handle it in the general context, but don't let me forget to talk about lawyers. So yeah, I would say that A very big mistake people make when they try to reinvent themselves is they try to throw a bomb into the end zone, which means they try to seek to make a pivot with a level of hubris, right? I was a corporate lawyer and now I want to do something completely new and I want to go in at the same level. But the best reinventions I've seen typically entail, not always, but oftentimes entail an interim step. You know, a private equity lawyer I know who was very much interested in becoming a private equity banker first went to an investment bank and he had to take a step down to do that. But it was an important step along the way to ultimately getting what he wanted. But he probably would have failed if he had gone straight from being a private equity lawyer to a private equity principal. So he did an interim step and This is all about, in my opinion anyway, the benefits of declaring war against your own ego. So to take 2 steps back to get 3 forward, or however you want to do the math, is typically a better way to go amongst people who are ultimately successful. Now, the one other thing I just want to say about lawyers, you know, not to say this is always true, uh, and I don't mean to stereotype the millions of lawyers out there, but in general, lawyers are used to being the adult in the room. And sometimes I have seen when lawyers seek to take on a position in a company on the business side, they fail to realize that it's often the children who are in charge, right? They resist this new reality. They resist experimentation, working in gray areas, asking for forgiveness rather than permission. These can be foreign concepts for well-trained lawyers, but I've seen them, if they don't have this sort of new mindset, about life on the business side, that potential transition cannot go well. So it is really something to be mindful of that, and oftentimes I think lawyers don't even realize that while they can be brilliant, they can sometimes be a little bit over-regimental in their thinking. Amazing. Thank you for sharing that. Something else that I saw that you've published recently was an article, and you were talking about, you know, an experimentation that you did with using LLMs. And to clarify for our lawyer audience, we're not talking about the Master of Law degrees, talking about, you know, the AI LLM, the large language model here. So can you tell us a little bit about your experience with LLM and The Great Gatsby? Yes, I would be delighted to. Hey, this was so much fun. It was painful, but it was fun. So just to sort of level set, I'm sure your audience has heard of ChatGPT. You go onto ChatGPT, there's a free version. It's great. It can handle a lot of requests that you make. But I had this idea, and the idea involved trying to coach famous fictional characters from books and movies that I have loved since I was a kid. And The Great Gatsby has always been high on my list. I live in Princeton, New Jersey. F. Scott Fitzgerald went to Princeton, so I just love that book. I love the period in which it's set against the whole thing. So I had this idea that it would be fun if I could ask a large language model to play the role of Jay Gatsby and play the role of Nick Carraway, and I would create a prompt, a coaching situation, and then I would be the coach and then they would go back and forth with me. But one of the things I learned was the sort of free version of ChatGPT isn't the right LLM for that kind of job. And also I discovered that many books are still on copyright and many sources of information that you may want to feed into an LLM might not be allowed because of the violation of copyright laws. So What I ultimately did was essentially configure my own LLM, and you can do that. It doesn't cost anything. You can go and download an LLM onto your computer, an open-sourced LLM, and then configure it in a much more customized way than the good old-fashioned ChatGPT that you, you can punch up on your website. And I soon found out that The Great Gatsby went off copyright. A couple of years ago. So I was able to download the whole book and I was able to download several scholarly articles about The Great Gatsby that were covered under a Creative Commons license. So I couldn't download them all, but I was able to download some of them. I then put all of that information into the model. So the model got much smarter. And then I said, okay, you know, LLM, you're now ready to play Gatsby. And now you're ready to play Nick Carraway, you know, 20 minutes later after I was done with my Gatsby coaching session. And it blew me away. I mean, they both passed the Turing test as far as I'm concerned. I felt like I, I was having a conversation with Jay Gatsby and we were talking about things that were not in the book. And same for Nick Carraway. As a matter of fact, I had a better coaching session for Nick Carraway than I did Jay Gatsby because Gatsby was just too preoccupied with his own image to, to really get deep with me. But yes, it was a fascinating example for me to see how I could, as just a guy, I could push the boundaries of what I could get LLMs to do. And this really ties back to the issue of getting your hands dirty. Everybody's got an opinion about AI, but it is much better when that opinion is informed by your own experimentation. Amazing. And taking that into consideration then with the experimentation aspect of it, which I guess has in an extent to do with people's careers and with their personal pursuits, But if I may ask you also, like, your personal opinion on LLMs and their role on the future of law from somebody who's observing this as well. Yeah, look, I think companies like Harvey.ai and Robin.ai, you know, I think they will be leveraged effectively by law firms to make their people more inefficient, but there's no getting around it. AI is a heat-seeking missile headed towards the legal profession. And I'm not saying that AI is going to replace all lawyers, but I do think AI will force lawyers to have to up their game because now people can use LLMs to draft contracts. Now, maybe they're not going to be as good, but for the cost-conscious customers out there, you know, they're going to keep on getting better. And the reality is the number of billable hours is probably going to be put under pressure over the longer term. So I think lawyers need to up their game. I think they need to Early in their career, think about specialties that will be ones where you know an LLM won't be sort of you know easy to use in in lieu of a person with wisdom. You know my my wife works for a law school, and you know there are a lot of people in in the law schools in in the U.S. scratching their heads trying to figure out how they maybe aren't going to reinvent themselves, but certainly adjust to AI. And you know you can either bury your head in the sand about it, or you can try to confront. confront the reality head-on. And I obviously think confronting it head-on and making AI be a weapon in your arsenal to make you as a lawyer smarter and more efficient is the way to go. Well, I must agree with that, especially as a law student. I feel like we kind of have that responsibility to get into the profession and maybe even introduce to more senior people these tools. And I know that comes with a lot of different problems and situations, but yeah, I definitely feel that responsibility to some extent. But something else, Greg, that as I learned about you. I came to know you're, you have quite a few things, outputs there in the public of the internet about, you know, networking connections and all of that. And I saw a couple of your YouTube videos where you talk about connections and you talk about going beyond connections in networking. So I'd love to hear a little bit more, you know, generally on connections and networking. And then if you could tell us a little more about what that looks like in practice. Sure. So I have a stake in a company called Connected Success. Connected Success, it's a bit of a tongue twister of a name, was founded by a guy named Keith Ferrazzi, who famously wrote a book called Never Eat Alone, and Ronan Olshansky, very good friend of mine, brilliant coach. And at the core of the business is this idea that like anything else in life, having a system That can enable you to pursue your goal in a steady, disciplined way is going to lead to better outcomes in the longer term. So they designed a system around relationship building, and I thought the system was brilliant. I coach people on how to build better and stronger and more powerful networks. So it was a natural fit for me to want to invest in the company and, and get involved personally as I have done. The good news is that there is a yawning massive gap Between what people say they're going to do when it comes to their relationships and what people actually do. Most people will tell you their relationships are the most important thing in their life, or it's up there, right? Oh, my relationships are what make my life worth living, all that stuff. And then you say to them, okay, well, how do you go about nurturing those relationships? Are you consistent? Do you schedule time every day to nurture relationships and keep them strong? Do you do those little things that make people feel really good? And the answer is most of the time, no. Why? Because it's hard and everybody's busy. But the reality is, if you do not invest in your relationships, they will ultimately not lead to the outputs that you want. And so Beyond Connections, which is the name of the class that they offer, is a fantastic roadmap to helping people create the networks that, you know, in their mind's eye, they've always wanted. Amazing. And in the same context, I feel like another topic that you explored quite a bit is just etiquette. And maybe that's something that people are just not being taught or that, you know, it's one of those secret things of business that, you know, everybody knows they should do, but maybe as new generations coming, they're not really told about that. or they don't see enough of it. So in today's world, things are so digital, so quick, in some ways transactional. Can you tell us a little more about things like handwritten notes, phone calls, formal introductions, and follow-up reporting back, all of that? Can you give us a high-level explanation of your approach to it? Absolutely. And I think it was really influenced by the fact that I have spent a fair bit of time advising and coaching people in the hedge fund world. And You know, in hedge fund land, people are incredibly creative about trying to, you know, find new sources of advantage always, right? Another term for that is alpha. And just like poker players who, you know, figure out an edge that nobody else has, really go in and exploit it, or professional handicappers for horse racing, I started thinking about where there were sources of alpha in terms of really building deep relationships quickly. And as you were saying, by virtue of the fact that texting is so pervasive and Slack, and there are just so many ways to interact with people now, I think etiquette has really become a lost art. And so as a way to sort of build relationships that outperform For me, I go an extra step and practice any number of different forms of etiquette in how I treat people and how I communicate with people that won't necessarily make a difference, you know, the first week that you're doing it, but over the long haul will. Now, I don't write people a thank you note every time I have an interaction, but if I have a lovely conversation with somebody, or if I meet somebody for coffee who I haven't seen in a while, They'll typically get a handwritten note from me. And if somebody takes the time to call me and check in on me, I'm not going to send them a text back because a text is a lower form of communication than a phone call. So I have a number of different rules about dos and don'ts and how you should treat people that, again, everybody would agree if I were to— I'm not going to bore you with my whole list now, but if I did, you would agree with them all. It's just that you're not going to do them because time is precious. I think it's worth it. Most other people don't. I'm trying to convince people otherwise. Well, and I'm happy that you got to talk about a few of them here. I hope that this further, you know, helps on your mission to convince people that it is important and that, you know, the small things really, really take you a long way. So I'll just give you one more just because it's fun. Claudio, let's say I introduce you to somebody new. Let's say I introduce you to a guy named Frank, and you're really excited to meet Frank. You and Frank proceed to have a great conversation, and Frank is going to Toronto in the near future, and you're gonna meet up with Frank. Most people will not tell me, the introducer, that you met up with Frank and had a great coffee with him. The smart thing to do is to write me a note saying, Greg, just want to let you know I met up with Frank, had a fantastic discussion with him in person. Thank you so much. By taking care of me, by making sure that I knew that you had the follow-up with Frank, I'm going to be more incentivized in the future to make introductions for you. I find it amazing that most people don't follow that practice. Absolutely amazing, but it's the nature of our world. That's incredible as you, as you talk about that, because I can recall, even though I'm quite young and all of that, but because of the podcast and being active on LinkedIn, I ended up meeting so many people, uh, in, in the last few years. So usually if you tell me, I really just wanted to connect with somebody to know about the bar exam in New York or how to do, you know, the, the licensing process in England. I usually have somebody to connect people regarding that, right? And as a matter of fact, I usually offer to do that, but I rarely hear back. I rarely hear back from either of the parties. And it always makes me wonder whether people like reached out at all. So I can totally understand how that in a way really doesn't incentivize you to do any more of that work, especially with that particular person. So it's definitely, Something that sounds like common sense, but I think we just don't speak enough about it. And I'm glad that I'm getting the chance to have this recorded in the podcast today. Good. Good. I'm glad too. And I feel like, especially as lawyers, right, as you're building a book, as you're preparing, and those relationships are so, so important in this profession. And I'm sure in all of them, but in this one, they really play a big role, right? So I really just appreciate your time to share with us some of your experience and And these tips. Thank you so much for being on the podcast today. It was my pleasure. I wish you and the podcast all the best. I hope your listenership continues to grow. It deserves to, and I look forward to continuing to listen. And thank you so much, you all, for tuning into today's episode. Please check the show notes under here just so you can see how to connect with Greg and see more of his work and channel, and hope you all have a great week. See you on the next episode.