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Episode 62

Law, Tech, and the Power of Staying Curious with Colin Levy

🏅Accredited by the Law Society of British Columbia
with Colin S. Levy00:15:08Apr 26, 2025
Law, Tech, and the Power of Staying Curious with Colin Levy
0:0015:08

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This transcript was generated by AI and may contain minor inaccuracies.

Hello, everybody. Welcome to another episode of Studying Law around the World. Today I'll have the opportunity to welcome Calling Levy. Calling is a general counsel and educator and author and advisor and so many other important roles. He's also an advocate for mental health and lots of good things out there on the Internet. So please join me in welcoming. Thank you so much for joining us today. Thanks so much for having me. Fantastic. Well, I know that you know, way you're, you don't need much of an introduction. I feel like a lot of people who might be listening to the podcast already know you follow you on social media and all of that. But I'd love to hear a little bit about, you know, your path and especially because I feel like you're legal journey has taken many unique turns and you've built such a nice practice for yourself. So I'd love to hear a little more about, you know, that this direction that your career has taken and and how you got where you're at. If someone had asked me, you know, do you envision yourself doing what you do now? When I started as a lawyer, as with a lot of folks who would be asked this question, I would say yeah, no, you're you're crazy. There's absolutely no way I be 4:00 AM doing what I am doing. But that just speaks to, I think this unpredictable journey that I've been on. And yet at the same time, looking back, the journey kind of makes sense to me. So one in the talk back a little bit, when I graduated from college, I worked for a year for a big law firm in New York as a paralegal, do an ediscovery work. And because I was interested in technology, I was interested in going to law. So I wanted to get a little bit of experience in before I pursued law school. So this, you know, opportunity struck me as sort of the perfect way to to achieve that goal. And it did. It gave me exposure to technology. I was able to understand how discovery works. Some of the tools are used in that in that space. But at the same time, I also saw the disconnect between the lawyers that I was performing this worked for at their request and the technology I was using. The lawyers didn't seem all that interested in the technology at all. They seemed interested in just getting the data they needed to get to achieve what they want to achieve. Come Fast forward a little bit to law school. Law school for me was a bit of a disappointment in that there was very little discussion of technology and law school. A lot of it was focused just on theory and kind of the history of how the law came to be, as many law schools remain focused on that. And yet I just became more and more convinced that either I was crazy or that there really was a gap between the practice of law and the reality on the ground in terms of how technology was impacting other industries like healthcare, insurance, and other spaces. So we're going graduated from law school and started working as a lawyer. I kind of became more and more interested in discovering whether indeed there were other folks that were trying to kind of bridge the gap between the legal world and the tech world. And little behold, there were folks that were doing that. And so I was, I guess at the time, bold enough to reach out to some of these folks and engage with them to learn more about the space, what they were trying to do to bridge that gap. And those conversations helped educate me, orientate me to the space. And I reached the point where I was wanting to share some of my lessons from those conversations with others. And that really started sort of me off on this journey into legal tech and also was providing me with a foundation to build off of. That's fantastic. Thank you sharing that. It's, it's been so interesting to see how different lawyers have, you know, implemented different, you know, technology in all their different principles into their career. Recently I spoke with a lawyer who went into privacy and they were just telling me a little bit about it might not be the case anymore, but just about, you know, a year, 2 ago, you could fast track your career so much using this specific niche because there aren't any lawyers who have been 10 years into this topic. But to continue our conversation here, I'd love to hear a little more about, you know, you've held these many hats I mentioned before, GC educator, author, advisor. How do you balance all of these roles while staying grounded in your core purpose? Yeah. You know, I'm, I'm just the type that like just stay busy and being engaged in a variety of different activities. So I think that I stay grounded through kind of just couple things. One, we're on minding myself that it's important to take a step back and to be grateful for what I've achieved and what I'm doing to, to really just at times kind of refocus myself on why became a lawyer in the 1st place, which was to help people and to also challenge myself intellectually. And then lastly, I think that being engaged in all these different activities allows me to remain connected to the community that empowers me and I find so inspiring. So that is in part what motivates me to remain active in doing what I do because I'm so inspired by others I encounter in the community and in seeking to help. No, that's beautiful. I love that. And continuing on that sense that you're online presence is pretty, it's pretty interesting. It's incredibly intentional, inspiring. You've raised awareness to so many important topics. So if I may ask you, what role has LinkedIn playing played in shaping your voice and building meaningful, meaningful connections within the legal community and more specifically in legal tech? Yeah. So it's interesting that LinkedIn has been, I think, a really beneficial platform for me because I kind of intuitively understood the value of the platform, which was to share informative content and to build connections with others. And LinkedIn really facilitates that through a variety of ways. And one of those ways was how I first sort of got my start on the platform, which is to comment on other people's posts and kind of provide my own thoughts and try to engage with them. And much to my surprise and some part, those folks did engage with me in response to the comments that I made, which then prompted me to reach out to them and connect with them and learn from them. So I'd say that LinkedIn really has been a key tool in my toolbox in terms of building my legal tech community, in terms of building my own expertise in this space, and then helping to support and inform others. And it remains a very powerful tool, one that I very much love to use. And I think it's important for me and also likely for others as well to not be distracted by kind of the metrics and terms of numbers or numbers of followers or connections or number of views on a post are really just be focused on providing informative and inspiring content for others. And so long as you do that consistently, I think that you'll gain benefit from using the platform. Indeed, that's been the case for me. I love the idea of using it with authenticity as well. I just find it awesome. The idea that you can use it authentically and you're writing speaks to transformation, but also practicality. So if I may ask you a little bit about first in the legal space, how do you continue to encourage legal professionals to embrace more innovation, to embrace more technology into their day-to-day practice? And then seeing that in the fast-paced world we're at, how do you put all these things together? How can you continually do this work? Yeah. So, you know, for me, what I really try to do is make technology as practical and as real per se as I can for others. And the way that I primarily do that is through date, through, you know, showing examples, case studies, sharing data and statistics, really just trying to kind of ground it in some reality. Because too often, I think especially in the tech world, this is not just isolated to legal tech. It's really, I think, a broad based issue with technology where there is so much noise and so much hype around technology, especially these days around AI. And I see myself and other, and I'm attracted to others who try to cut through all the noise and the hype and try to provide sort of a real sense of what's possible, what's not possible, what could be possible. And it's a constant challenge, but it's one that I happily take on because I do think it's important for people to understand a couple of things, that technology is here to stay and that it shouldn't be something that's intimidating or overwhelming, but really should be something that helps them be them being others, being more productive with their time and what they're doing. That's incredible and it's showing that I've I've seen where you where you said that standing still is not an option in this market. So how does that you know and helps you to stay curious to help others and also to avoid the complacency in in the workplace? Yeah, so I am just one who is never happy to just not be learning or what have you. So for me, I just see myself as a constant learner because I see learning as a lifelong process. It doesn't have a defined endpoint, doesn't really have an endpoint at all. So that means that I constantly have to learn and have to adapt. And I think that's important for all of us to do because none of us knows everything or is good at everything. So we all have to be acknowledged sort of wrong shortcomings and our strengths as well as our weaknesses. And so I often kind of been reminded of the fact that the more I know, the more reminded of how much there is to learn. And so that inspires me to keep on learning and keep on experimenting. I think as we've seen with technology being very changeable, very dynamic, that learning really is something that needs to be constantly focused on and done because otherwise you're going to lose sight of what's going on in front of. You yeah, absolutely. And, and talking about that same topic about the workplace and and where you're at, I'd love to hear a little bit about happiness at work. A few weeks ago, I feel like we both saw one of chat about post chat about and I think his post was very interesting. He talked about intentionality and and all of that. And I feel we both connected in that in in commenting to that. So I'd love to hear from you. What does a a fulfilling career look like to you and how have you built that into your professional life? Yeah. So for me, a fulfilling career means one that is focused on helping others and that is provided me with a sense of contentment and happiness. And because of my passion for legal tech, my role as general counsel Malbec and my role as sort of legal tech educator gives me a strong sense of fulfillment and contentment because I'm helping others, I'm helping myself. And so it's just sort of a really rewarding place to be. And I feel very lucky and grateful to be in this position because it certainly took a lot of work and time to get there. But now that I'm here, I'm really, really, just, as I said before, grateful to be doing what I'm doing at this point. Amazing. And in that sense, you know, a lot of people are starting up their careers and I feel like the legal field has so many different things that you can explore and maybe you're not, you know, feeling that you're super happy at your first job. So I'd love to hear, you know, what kind of advice would you give to someone trying to find know that in that intersection, that sweet spot about where they're what they're good at, what they care about, where they can make a difference and putting that all together. Yeah. So I think it starts from kind of asking yourself the question of why, you know, why are you pulled in a certain direction? Why do you want to do something a certain way? What is the motivation? What what is pulling you or pushing you in that direction? And use that then to guide you as you would kind of explore opportunities. Because I think the more you know yourself, the more you listen to yourself and what drives you, the more likely you're going to feel fulfillment and whatever it is you're doing and, or find something that is most aligned with who you are and what you want to be doing. And that sometimes takes some work, it takes some experimentation and sometimes even takes failing. But that's part of the process, frankly. So you kind of have to kind of sit with that sort of sense of, you know, you may be uncomfortable at times, you may fail at times, but that's just, we all fail. We all feel unhappy at times, such as part of the journey of life. So we have to kind of be comfortable being uncomfortable, as I like to say. I love that. And during the same topic calling, if I may ask you thinking about, you know, again, those people who are starting up their careers and all of that. In your personal opinion, would you feel that maybe you might need to start where you don't necessarily love the work yet in order to build that future practice that then you come to love and appreciate and be able to, you know, have a little bit more of a decision making power and and help on, you know, shaping that workplace. Do you feel like that has some truth to it? Had some kind of have you seen that happening in other people's lives or has that, does that resonate in any way with your career experience? Yeah, well, I can speak from a couple of different angles. One from personal experience where, yeah, I've, I've had a couple of roles where I wasn't happy a lot of the time, but I was getting these skills and experience I knew I needed to get to be doing what I want to be doing eventually. So I had to kind of tolerate it for as long as they could or as long as they felt like I I was able to and needed to. So I do think that especially for younger lawyers or other legal professionals, unfortunately, the reality really is that sometimes you have to take a job you don't necessarily love because of the experience and the opportunities may afford you. And ideally, that would be at a company where you, you know, at least can focus on doing your job and not have to worry about sort of internal politics or other personalities. But the fact of the matter is sometimes you have to because we all have different personalities and we're all not going to be, you know, best friends with everyone. So I think that's important skill as well as being able to kind of just understand how to get along with people that you don't necessarily want to get along with or, you know, frankly don't even want anything to do with it depending on the situation. So, yeah, I do think that sometimes, you know, it's build a foundation requires doing things you don't necessarily want to love to do. Because the other part of it is regardless of what job you have, at any stage of your career, there's a high likelihood of you having to do at least one thing you're not really going to want to have to do. So the more you can get used to and be OK with that situation, the better off you'll be over the long term. Fantastic. Well, I really appreciate your time. I really appreciate your answers here in the podcast today, and thank you so much for joining us. Thanks so much for having me, I really enjoy this conversation. It's always great to talk with you and thank you all for tuning into this episode and we'll see you on the next one.

Hello, everybody. Welcome to another episode of Studying Law around the World. Today I'll have the opportunity to welcome Calling Levy. Calling is a general counsel and educator and author and advisor and so many other important roles. He's also an advocate for mental health and lots of good things out there on the Internet. So please join me in welcoming. Thank you so much for joining us today. Thanks so much for having me. Fantastic. Well, I know that you know, way you're, you don't need much of an introduction. I feel like a lot of people who might be listening to the podcast already know you follow you on social media and all of that. But I'd love to hear a little bit about, you know, your path and especially because I feel like you're legal journey has taken many unique turns and you've built such a nice practice for yourself. So I'd love to hear a little more about, you know, that this direction that your career has taken and and how you got where you're at. If someone had asked me, you know, do you envision yourself doing what you do now? When I started as a lawyer, as with a lot of folks who would be asked this question, I would say yeah, no, you're you're crazy. There's absolutely no way I be 4:00 AM doing what I am doing. But that just speaks to, I think this unpredictable journey that I've been on. And yet at the same time, looking back, the journey kind of makes sense to me. So one in the talk back a little bit, when I graduated from college, I worked for a year for a big law firm in New York as a paralegal, do an ediscovery work. And because I was interested in technology, I was interested in going to law. So I wanted to get a little bit of experience in before I pursued law school. So this, you know, opportunity struck me as sort of the perfect way to to achieve that goal. And it did. It gave me exposure to technology. I was able to understand how discovery works. Some of the tools are used in that in that space. But at the same time, I also saw the disconnect between the lawyers that I was performing this worked for at their request and the technology I was using. The lawyers didn't seem all that interested in the technology at all. They seemed interested in just getting the data they needed to get to achieve what they want to achieve. Come Fast forward a little bit to law school. Law school for me was a bit of a disappointment in that there was very little discussion of technology and law school. A lot of it was focused just on theory and kind of the history of how the law came to be, as many law schools remain focused on that. And yet I just became more and more convinced that either I was crazy or that there really was a gap between the practice of law and the reality on the ground in terms of how technology was impacting other industries like healthcare, insurance, and other spaces. So we're going graduated from law school and started working as a lawyer. I kind of became more and more interested in discovering whether indeed there were other folks that were trying to kind of bridge the gap between the legal world and the tech world. And little behold, there were folks that were doing that. And so I was, I guess at the time, bold enough to reach out to some of these folks and engage with them to learn more about the space, what they were trying to do to bridge that gap. And those conversations helped educate me, orientate me to the space. And I reached the point where I was wanting to share some of my lessons from those conversations with others. And that really started sort of me off on this journey into legal tech and also was providing me with a foundation to build off of. That's fantastic. Thank you sharing that. It's, it's been so interesting to see how different lawyers have, you know, implemented different, you know, technology in all their different principles into their career. Recently I spoke with a lawyer who went into privacy and they were just telling me a little bit about it might not be the case anymore, but just about, you know, a year, 2 ago, you could fast track your career so much using this specific niche because there aren't any lawyers who have been 10 years into this topic. But to continue our conversation here, I'd love to hear a little more about, you know, you've held these many hats I mentioned before, GC educator, author, advisor. How do you balance all of these roles while staying grounded in your core purpose? Yeah. You know, I'm, I'm just the type that like just stay busy and being engaged in a variety of different activities. So I think that I stay grounded through kind of just couple things. One, we're on minding myself that it's important to take a step back and to be grateful for what I've achieved and what I'm doing to, to really just at times kind of refocus myself on why became a lawyer in the 1st place, which was to help people and to also challenge myself intellectually. And then lastly, I think that being engaged in all these different activities allows me to remain connected to the community that empowers me and I find so inspiring. So that is in part what motivates me to remain active in doing what I do because I'm so inspired by others I encounter in the community and in seeking to help. No, that's beautiful. I love that. And continuing on that sense that you're online presence is pretty, it's pretty interesting. It's incredibly intentional, inspiring. You've raised awareness to so many important topics. So if I may ask you, what role has LinkedIn playing played in shaping your voice and building meaningful, meaningful connections within the legal community and more specifically in legal tech? Yeah. So it's interesting that LinkedIn has been, I think, a really beneficial platform for me because I kind of intuitively understood the value of the platform, which was to share informative content and to build connections with others. And LinkedIn really facilitates that through a variety of ways. And one of those ways was how I first sort of got my start on the platform, which is to comment on other people's posts and kind of provide my own thoughts and try to engage with them. And much to my surprise and some part, those folks did engage with me in response to the comments that I made, which then prompted me to reach out to them and connect with them and learn from them. So I'd say that LinkedIn really has been a key tool in my toolbox in terms of building my legal tech community, in terms of building my own expertise in this space, and then helping to support and inform others. And it remains a very powerful tool, one that I very much love to use. And I think it's important for me and also likely for others as well to not be distracted by kind of the metrics and terms of numbers or numbers of followers or connections or number of views on a post are really just be focused on providing informative and inspiring content for others. And so long as you do that consistently, I think that you'll gain benefit from using the platform. Indeed, that's been the case for me. I love the idea of using it with authenticity as well. I just find it awesome. The idea that you can use it authentically and you're writing speaks to transformation, but also practicality. So if I may ask you a little bit about first in the legal space, how do you continue to encourage legal professionals to embrace more innovation, to embrace more technology into their day-to-day practice? And then seeing that in the fast-paced world we're at, how do you put all these things together? How can you continually do this work? Yeah. So, you know, for me, what I really try to do is make technology as practical and as real per se as I can for others. And the way that I primarily do that is through date, through, you know, showing examples, case studies, sharing data and statistics, really just trying to kind of ground it in some reality. Because too often, I think especially in the tech world, this is not just isolated to legal tech. It's really, I think, a broad based issue with technology where there is so much noise and so much hype around technology, especially these days around AI. And I see myself and other, and I'm attracted to others who try to cut through all the noise and the hype and try to provide sort of a real sense of what's possible, what's not possible, what could be possible. And it's a constant challenge, but it's one that I happily take on because I do think it's important for people to understand a couple of things, that technology is here to stay and that it shouldn't be something that's intimidating or overwhelming, but really should be something that helps them be them being others, being more productive with their time and what they're doing. That's incredible and it's showing that I've I've seen where you where you said that standing still is not an option in this market. So how does that you know and helps you to stay curious to help others and also to avoid the complacency in in the workplace? Yeah, so I am just one who is never happy to just not be learning or what have you. So for me, I just see myself as a constant learner because I see learning as a lifelong process. It doesn't have a defined endpoint, doesn't really have an endpoint at all. So that means that I constantly have to learn and have to adapt. And I think that's important for all of us to do because none of us knows everything or is good at everything. So we all have to be acknowledged sort of wrong shortcomings and our strengths as well as our weaknesses. And so I often kind of been reminded of the fact that the more I know, the more reminded of how much there is to learn. And so that inspires me to keep on learning and keep on experimenting. I think as we've seen with technology being very changeable, very dynamic, that learning really is something that needs to be constantly focused on and done because otherwise you're going to lose sight of what's going on in front of. You yeah, absolutely. And, and talking about that same topic about the workplace and and where you're at, I'd love to hear a little bit about happiness at work. A few weeks ago, I feel like we both saw one of chat about post chat about and I think his post was very interesting. He talked about intentionality and and all of that. And I feel we both connected in that in in commenting to that. So I'd love to hear from you. What does a a fulfilling career look like to you and how have you built that into your professional life? Yeah. So for me, a fulfilling career means one that is focused on helping others and that is provided me with a sense of contentment and happiness. And because of my passion for legal tech, my role as general counsel Malbec and my role as sort of legal tech educator gives me a strong sense of fulfillment and contentment because I'm helping others, I'm helping myself. And so it's just sort of a really rewarding place to be. And I feel very lucky and grateful to be in this position because it certainly took a lot of work and time to get there. But now that I'm here, I'm really, really, just, as I said before, grateful to be doing what I'm doing at this point. Amazing. And in that sense, you know, a lot of people are starting up their careers and I feel like the legal field has so many different things that you can explore and maybe you're not, you know, feeling that you're super happy at your first job. So I'd love to hear, you know, what kind of advice would you give to someone trying to find know that in that intersection, that sweet spot about where they're what they're good at, what they care about, where they can make a difference and putting that all together. Yeah. So I think it starts from kind of asking yourself the question of why, you know, why are you pulled in a certain direction? Why do you want to do something a certain way? What is the motivation? What what is pulling you or pushing you in that direction? And use that then to guide you as you would kind of explore opportunities. Because I think the more you know yourself, the more you listen to yourself and what drives you, the more likely you're going to feel fulfillment and whatever it is you're doing and, or find something that is most aligned with who you are and what you want to be doing. And that sometimes takes some work, it takes some experimentation and sometimes even takes failing. But that's part of the process, frankly. So you kind of have to kind of sit with that sort of sense of, you know, you may be uncomfortable at times, you may fail at times, but that's just, we all fail. We all feel unhappy at times, such as part of the journey of life. So we have to kind of be comfortable being uncomfortable, as I like to say. I love that. And during the same topic calling, if I may ask you thinking about, you know, again, those people who are starting up their careers and all of that. In your personal opinion, would you feel that maybe you might need to start where you don't necessarily love the work yet in order to build that future practice that then you come to love and appreciate and be able to, you know, have a little bit more of a decision making power and and help on, you know, shaping that workplace. Do you feel like that has some truth to it? Had some kind of have you seen that happening in other people's lives or has that, does that resonate in any way with your career experience? Yeah, well, I can speak from a couple of different angles. One from personal experience where, yeah, I've, I've had a couple of roles where I wasn't happy a lot of the time, but I was getting these skills and experience I knew I needed to get to be doing what I want to be doing eventually. So I had to kind of tolerate it for as long as they could or as long as they felt like I I was able to and needed to. So I do think that especially for younger lawyers or other legal professionals, unfortunately, the reality really is that sometimes you have to take a job you don't necessarily love because of the experience and the opportunities may afford you. And ideally, that would be at a company where you, you know, at least can focus on doing your job and not have to worry about sort of internal politics or other personalities. But the fact of the matter is sometimes you have to because we all have different personalities and we're all not going to be, you know, best friends with everyone. So I think that's important skill as well as being able to kind of just understand how to get along with people that you don't necessarily want to get along with or, you know, frankly don't even want anything to do with it depending on the situation. So, yeah, I do think that sometimes, you know, it's build a foundation requires doing things you don't necessarily want to love to do. Because the other part of it is regardless of what job you have, at any stage of your career, there's a high likelihood of you having to do at least one thing you're not really going to want to have to do. So the more you can get used to and be OK with that situation, the better off you'll be over the long term. Fantastic. Well, I really appreciate your time. I really appreciate your answers here in the podcast today, and thank you so much for joining us. Thanks so much for having me, I really enjoy this conversation. It's always great to talk with you and thank you all for tuning into this episode and we'll see you on the next one.

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Law, Tech, and the Power of Staying Curious with Colin Levy

studyinglawaroundtheworld.com

Law, Tech, and the Power of Staying Curious with Colin Levy

With Colin S. Levy. Recognized leader in legal tech, Colin S. Levy is dedicated to revolutionizing the legal industry by bridging the gap be

Legal Technology
Contract Lifecycle Management
Legal Innovation
Career Development

About This Episode

Recognized leader in legal tech, Colin S. Levy is dedicated to revolutionizing the legal industry by bridging the gap between technology and law. As an author, educator, and speaker, Colin demystifies the complexities of legal innovation. He’s the author of The Legal Tech Ecosystem, co-author of CLM for Dummies, and editor of the Handbook of Legal Tech. With a passion for empowering the legal tech community, Colin’s insights appear in Today’s General Counsel, and he serves as a judge for the American Legal Technology Awards. As General Counsel for Malbek, he stays at the forefront of Contract Lifecycle Management, advising startups and investing in emerging tech. Colin’s mission is clear: to inspire and lead the legal world into a tech-driven future.

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Disclaimer: Guests participate in Studying Law Around the World in their personal capacity and not as representatives or spokespersons of their employer, law firm, organization, clients, or other affiliated entities, unless otherwise stated. The views, opinions, experiences, and statements expressed during the episode are those of the individual guest and do not necessarily represent the views or positions of any organization with which the guest is associated. Nothing stated by a guest should be understood as an official statement, endorsement, or position of their employer or any other affiliated organization.

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