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Ep 63: From Prosecutor to GC at Enfusion with Matt Campobasso
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How can the general counsel become a true partner to the executive team? How about in the context of a public company? How can the general counsel ensure that that same can-do attitude that they bring to the table pervades the rest of their legal team?
Join Matt Campobasso, General Counsel at Enfusion, as he shares stories and lessons from his unique legal career: starting as a prosecutor outside of Chicago, litigating at a firm for more than a decade and becoming partner, then transitioning to in-house and leading legal at a publicly-traded fintech company.
Listen as Matt discusses how his time in the courtroom shaped his approach to in-house legal, how to build a department of independent, driven lawyers, cultivating a business mindset in your team, and more.
Read detailed summary: https://www.spotdraft.com/podcast/episode-63
Topics:
Introduction: 0:00
Tyler asks about his career as an Illinois prosecutor: 1:36
Tyler asks what inspired Matt to be a prosecutor: 4:32
Tyler asks about transitioning in-house roles in tech: 16:33
Tyler asks about managing work relationships after you become general counsel: 24:15
Tyler asks about instilling a business mindset in a legal team: 29:56
Tyler on hiring lawyers with an owner’s mindset: 37:32
Tyler asks fun questions: 43:50
Book recommendations: 49:22
What Matt wish he knew as a young lawyer: 52:16
Connect with us:
Matt Campobasso - https://www.linkedin.com/in/mrc1921/
Tyler Finn - https://www.linkedin.com/in/tylerhfinn
SpotDraft - https://www.linkedin.com/company/spotdraft
SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues.
Visit https://www.spotdraft.com to learn more.
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Transcript
00:00:00
Speaker
I won't bore your listeners with the full story, but on my first day, I was filling out my insurance forms and the head of our criminal division came in my office. Her name was Nicole and she said, hey, I need you to run up to courtroom 301. We've got a DUI trial. I need you to pick a jury. and i i scroll was I was like, what? I just got here an hour ago.
00:00:25
Speaker
How can the GC be a true partner to the executive team? How about in the public company context? How does the GC ensure that that same can-do attitude that they bring to the table pervades the rest of their legal team?
00:00:42
Speaker
Today, we are joined on the abstract with by my friend Matt Campobasso, General Counsel of Infusion. Infusion provides a software platform that unifies the front, middle, and back offices for investment managers. and I'll ask Matt at some point to give us a sort of more detailed explanation about what Infusion does too. Matt was promoted two years ago to the GCU role after serving as their Deputy General Counsel, a transition that we're going to chat about today.
00:01:11
Speaker
He also has prior experience as GC of Truqua, an IBM company, and as a litigator, and he started his career as a state prosecutor. Matt, thanks so much for joining me today for this episode of The Abstract. My pleasure, Tyler. I really appreciate you having me. I'm ah i'm a big fan of the the podcast.
00:01:30
Speaker
Well, that's nice of you to say. We've had a lot of great GCs on. I'm super excited for our conversation. I actually want to go back and and start a bit. I'm watching the show right now, Presumed Innocent yeah on Apple TV. i You started as a state prosecutor in in Illinois, right? Not in Cook County, but in Illinois. I like Jake Gyllenhaal's character on the show, yes.
00:01:52
Speaker
the Great show. i guess yeah First question, is the show accurate? Does it depict the the life of a prosecutor and what the offices look like sort of for real or is it Hollywoodized? You know what? it's I mean, present company included. I didn't have any colleagues that were as handsome as Jake Gyllenhaal. That part was definitely Hollywoodized. It was funny. I watched it and it's been a long time since I was a prosecutor i left the prosecutor's office back in two thousand and eight that being said there were some things that really kind of rang true for me i think the pace with which things can move definitely was there obviously the circumstances around the show are a bit different neither myself or any of my colleagues were accused of murdering any of our college
00:02:38
Speaker
That's, you know, obviously a good thing. But no, I mean, there were definitely some things that I i was like, oh, man, like that feels a little bit like I can remember that like I can remember sitting in an office late at night, like, and and working with my trial partner talking about like strategy or a closing argument and thinking about things. obviously, you know, like most legal dramas or even like, you know, criminal procedure dramas, everything's kind of condensed. But yeah, I mean, there were definitely and you know, I don't know how far you are into the show will avoid spoilers for your listeners. But yes, and for you, obviously, but I, you know, the Peter Sarsgaard character, Peter Sarsgaard character, the prosecutor, Tommy Molto, I think is his name on the show. I really enjoyed his performance, not only because he's a great actor, but because it was very similar to openings, closings, examinations. And, you know, sometimes you'd find yourself getting very kind of swept up in the facts of a case. And obviously in that show, it's very personal. For me personally, like I just I can recall specifically some cases where there were some pretty horrendous crimes committed and just sometimes having to like really be mindful of separating
00:03:45
Speaker
like my own emotion and my own sense of like right and wrong from my job. And that's something that like, right actually, if depending how far you are into the show, like they definitely seem to touch on that idea a little bit, which is, hey, you can't make things personal. And again, it's very different under the circumstances of the the case in presumably.
00:04:04
Speaker
But I consider myself a relatively empathetic person. And so I would oftentimes be in cases and, you know, if we were able unable to obtain like a guilty verdict and a victim had come in and testified, you take that home with you. And so obviously, again, the the stakes and the underlying circumstances are very different um than my experience. But I can say some of the emotional parallels that I had as a prosecutor. So and it's just highly entertaining, like very, very entertaining television.
00:04:32
Speaker
That's really interesting that you you bring up sort of taking it home. I think there's a part of that, though, that is what motivates people to want to work in government or to want to work as a prosecutor or you know as a public defender or is that you feel that attachment to the outcome. It's not just sort of like numbers on a spreadsheet trending in the right direction or the graph headed in the right way.
00:04:55
Speaker
Did you go into the law with the idea of becoming a prosecutor in mind? like what What inspired you to pursue the law as your career? Yeah, i it's funny. I have a daughter. She's 10. We were just driving home last night. She takes it's guitar lessons. and i Over time, as taking her there each week, I have always wanted to learn how to play a string instrument. and I was given a banjo as a gift. I'm a big fan of the Avett Brothers. It's a band. I don't know if you know them or not, but I'm a huge fan. Banjo features heavily. My dad got me a banjo for Christmas years ago, and I like will pluck it. You know, I'm not very good. And so I've gone into these lessons with her for two years and about four months ago, five months ago.
00:05:34
Speaker
the owner was like hey you should schedule banjo lessons like at the same time that your daughter's taking guitar so last night we were at banjo slash guitar lessons and on the way home she started fifth grade today so we were talking about like education in school and it's not a super long car ride but i was like you know what do you do you think you know what you do you have a sense of what you want to be when you grow up ah she was like i want to be a lawyer and i said are you sure like really like You know, I'm a lawyer, right? Like you've seen, you've you've seen what it did to me. um And she's like, yeah. And it's funny of my three kids, people often say that she is like, from a personality perspective and intellectually like the apple that fell closest to the tree. And and I actually said to her, I could
00:06:19
Speaker
100% CU. She has like that analytical mind, that desire to help people, the desire to solve problems. and so I had that at a young age also. It's not uncommon that I am told that I overthink things, which I don't think is necessarily a bad thing as a lawyer. you know In my personal life, it can create a lot of friction, as you might imagine. um You know, for me, it was always an idea that I liked, you know, I saw legal movies growing up and I thought, well, it's cool. yeah It's Hollywood eyes. But my uncle, who is also my godfather, is a lawyer or he is a retired lawyer. But he is someone I looked up to when I was younger and I remember thinking when I got older about a career.
00:06:57
Speaker
And I just said to him, like you know do you like being a lawyer? And he's like, I love it. like it's You get to help people, you get to solve problems. And I remember he said, you know you should really look into it. And I and i did. I was pre-law as an undergrad, and I enjoyed it. I took some like legal learning classes in high school. We had some local lawyers that came in and taught us a zero period like before school started. I was kind of weird. I was like, let me take extra classes.
00:07:23
Speaker
That's pretty cool. Yeah, it was cool. um It was a very cool experience. And we did like mock trials and stuff. And yeah, i just I was fascinated by the idea that really regardless of what part of the world you're thinking about, right? Region indifferent, industry indifference, whether it's education or health or criminal justice, like lawyers are there, right? And they're not just like there. They're there in a way that influences outcomes and they have you know a lot of our elected officials are are lawyers or have law degrees you know and it's it's an incredibly versatile education um i always think i considered i would want to be more of a traditional practicing lawyer which is what i've been since i was licensed in two thousand and six so that's what kind of got me to the law when i was in law school my front my first year i was a good student i wasn't like top of my class by any means and so when on campus interviews were happening You know, I threw my hat in the ring with a couple firms, didn't get any bites. And I was like, okay, time to think about, you know, my contingency. And in talking with my uncle, the same uncle, he said, you know, some of the best lawyers I've ever worked with in my career came through the state's attorney's office. They were prosecutors. And so I thought, okay. And he's like, look, you could do it for a couple of years. You cut your teeth, they throw you in the deep end, and you're going to learn a lot of lessons. You're going to fall on your face.
00:08:40
Speaker
but you come out of it so advanced for that point in your career and so i did it and i was there for almost two years um i clerked as a student a law student in lake county illinois which is just northwest of chicago and then i actually prosecuted as a licensed attorney from 2006 to 2008 in McHenry County, which is due west of Chicago. So all of which is about 45 miles from the city. The reason I went to the Collar counties was because in Cook County, where we see presumed innocent taking place, there's a hierarchy of time served. And so you go through appeals and then family court. And it's kind of like before you're trying cases in presumed innocent, you've been there for 10 years.
00:09:19
Speaker
And I knew this was probably a two or three year thing for me. And so I thought, where can I go? You know, I'd rather be a bigger fish in a smaller pond because for me, it's all about extracting the experience. And so I went to McHenry County and I won't bore your listeners with the story, the full story. But on my first day, I was filling out my insurance forms and the head of our criminal division came in my office. Her name was Nicole and she said, hey,
00:09:42
Speaker
I need you to run up to courtroom 301. We've got a DUI trial. I need you to pick a jury." And i i scroll was I was like, what? I just got here an hour ago. And she's like, yeah, so and so is out. I didn't know who so and so was. And I was like, okay. And so I went up there and I walked in and there was another lawyer there. His name is Bill Stanton. He was like a long time prosecutor. And I was like, oh, thank God. and he's And he's like, what? And I said, I think we're trying this DUI together. And he's like, no, no, I'm leaving. And he left.
00:10:11
Speaker
And I picked a jury. I did an opening. I you know put on the the case, the the state's case in chief. the The officer, the deputy was incredible. Like he, I mean, this guy was just like, his report was impeccable. His testimony was great. And, you know, the judge, I think a few times was like, this guy, like this is the best the state's got. And, you know, And I and and we've got a guilty verdict. And I walked out of there and I was like simultaneously like exhilarated and just terrified. And I was like, what just happened? And I went back to my desk and I finished filling out my insurance forms and I went home and I thought, OK, well, there's that experience that you were looking for. And then.
00:10:49
Speaker
you know two years later i had tried a hundred cases um wow made some like horrifically boneheaded mistakes and lessons and learned lessons and yeah and then i turned that into you know an opportunity to go work for it's the firm was acquired but the name at the time was freeborn and peters which was a renowned litigation firm in chicago And I went there, I was one of 120 litigators. And I spent 11 years there as an associate and then a partner. And I, you think about bootcamp, right, for like the Marines, it's intense. It's like what, eight weeks or whatever, or six weeks, I had an 11 year bootcamp. And I can say without any hesitation,
00:11:27
Speaker
that the lawyer that I am today, for better or worse, is a byproduct of the incredible lawyers I worked with at that firm. And just like, it's almost like a kid in a, you know, to the extent that your candy is learning how to be a good lawyer. from the candy store There were the best brief writers, the best like ah lawyers, the best deposition takers, the best people who were able to client to counsel their clients.
00:11:49
Speaker
And I just would like sit back and work with 50 different lawyers and think, like I like how she does this, or he's great at that, or she's an amazing trial lawyer. And I just like learned, and I i i stole. right I just was like, I'm going to absorb this. And yeah, I became, I think,
00:12:05
Speaker
um an effective litigator because I tried to turn myself into like a Swiss army knife of skills. i mean that My road to my success was paved with like the work and the experience and the successes of like so many other lawyers. i mean I could spend an hour naming them and talking about them, it's it's incredible. You don't realize that when you're a young lawyer, you're like, oh, I just need to go do it. and Then you're like, no, no, you need to like learn from people. right That's the best way. Then obviously, learn enough to then you can go do it and then you make mistakes and then you evolve and you mature. so It is a practice, I think. hundred per percent And I think folks, even in other professions that aren't so clearly defined as a practice, ah like being a doctor or being a lawyer, I think that it's good for, you know, even folks like me to sit back and remember that sometimes we should approach our careers and our professions like that, too. We should try to learn from others, learn by osmosis, recognize that experience
00:13:04
Speaker
make you just lessons that we're not going to be able to pick up in a book. I mean, and and you know, again, that's another episode of podcast altogether. Yeah. The way I was taught to be a lawyer did not prepare me to be a lawyer. Law school was a great experience. It rewired my brain. Some of that overthinking I mentioned earlier is a direct product of those three years that I spent in law school.
00:13:25
Speaker
Yeah, you know, you realize like why when Abraham Lincoln was a lawyer, that most lawyers didn't go to law school, they had apprenticeships, right? They just, they went and they did it. And, you know, it's funny that you say it's a practice. I had a one judge specifically that I appeared in front of many, many times as a criminal prosecutor. And I would make, again, boneheaded mistakes. And he would say, Mr. Campobasso, that's why they call it the practice of law. Like,
00:13:49
Speaker
Because I'm just be like, Your Honor, I'm embarrassed. And he's like, it it was he was incredibly gracious about it. And, you know, he did his job. And but at the end of the day, he just was like, Look, I see, you know, this young lawyer who cares, he works hard, like he's showing up, he makes mistakes. And he was funny. He his name was Charles, which he's now retired, but he was a former public defender, the former public defender.
00:14:11
Speaker
And so you would imagine, and he was incredibly impartial, but you would imagine as someone who was responsible for defending people who couldn't afford their own counsel, he had a lens of, hey, the burden of proof of beyond a reasonable doubt is like, you know, and it's already the highest burden under the law, but then you get a former public defender who's hearing your case.
00:14:30
Speaker
And you had to be perfect and he and I, I don't want to be butt heads because again, he was the judge. I was in his courtroom. I'm an officer of the court. I was always tried to be very respectful, but I'll never forget after my year and a half, almost two years in the office, I went to his chambers. I no longer appeared in front of him at that time.
00:14:47
Speaker
But I went to his chambers to let him know I was leaving. And he said, you know this was this was in March, February of 2008. And he said, you know Mr. Campobasso, I know we did not always see eye to eye. He's like, but it is my sincere hope that 15 years from now, you're going to look back and you're going to say, you know what? I'm a better lawyer because I appeared in front of Judge Wiech. And obviously, here we are 16 years later. And I'm saying exactly that. And you know you just don't realize, I think, this isn't obviously specific to the law. This is specific to life.
00:15:16
Speaker
You don't realize like there's a very famous quote and I'm not even going to try to say it because I don't remember the exact words. But the sentiment is like your friends are like they don't make you better. Your friends like you for who you are. It's actually your enemies that make you better. Right. Because they challenge you and they look for your weaknesses. And if you're paying attention, they give you an opportunity to be stronger, to be better, to be faster. And so I don't think Judge Which was my enemy by any means. He was doing his job, but he was incredibly difficult to practice in front of. But again, I am a person who believes that you make a mistake once and you know you learn from it. If you make it more than once, that's a behavior and that's not good. And so with him, I made a mistake. He would absolutely let me hear about it. It would be sometimes embarrassing. I'll go back to my office and think never again. And so absolutely, it's a practice. I practice
00:16:07
Speaker
today, I will practice until I stop practicing. I learn constantly. And that's one of the things that I love about my job is that the law is ever changing. And because so much of the law is analyzing and applying the law to facts, right? Every time you encounter a set of facts, they're different. And so even on days where I'm dealing with similar issues, I find myself finding new ways to look at those issues, and hopefully new and exciting and effective ways to solve for them.
00:16:33
Speaker
Talk to us a little bit about your path to GC, into tech and to the GC role, both sort of before infusion and and afterwards. And then I really want to dig in on this transition from DGC to GC, because I think that's one of the most interesting moments in your your career.
00:16:50
Speaker
Yeah, it definitely I'm happy to expand on my particular journey there. I mean, yeah, I mentioned I had my 11 years at my in my law firm experience, and I loved it. And I kind of got to that, what I would say like, I don't know if it was the top of the mountain, but near the top as it a partner.
00:17:06
Speaker
hi And I was like, you know, I think I want to go be an in-house lawyer. And ah people were like, what? Like you just made partner. I was like, yeah, I know. But also, I feel like there's something else out there that I could be even better at. And right. And if you're not growing, I feel like you're dying. And so I just was like, look, that's a challenge. I'm not trying to be reckless. I just think this is something that I want to explore. And so I just i think I just turned 40. I went to a company called Elevate as a kind of an outside-sourced, almost like an incremental AGC. And it allowed me to kind of straddle that line between law firm and also learning about what an in-house lawyer did. And to me, that was kind of a way to hedge. you know I was like, OK, well, if I don't love it, I'll just jump into the law firm thing again, and I'll be fine.
00:17:50
Speaker
right I loved it. And um I did that for about a year and a half. And I was like, okay, this is for me. That's when I synced up with Truqua. And they were a small consultancy that was later acquired by IBM, ah or GC for like six months, I thought I was going to be there forever. COVID hit and the owners of the business were like, you know, we're a little worried about our revenue. They were a thriving business and they continue to be I've stayed very close with a lot of people there.
00:18:13
Speaker
But I was like, you know what, I don't want to, you know, no offense to IBM, I didn't want to go necessarily be like a rank and file IBM lawyer. I asked if they needed a GC, they did not, they already had one. So and I was like, all right, well, I'm gonna take some experience, I'm gonna try to like, parlay that into something. And yeah, I like, found out about infusion. You know, it's coming up on four years for me there. When I joined, we were a private company.
00:18:37
Speaker
I was brought in as the DGC. I was the third lawyer. and yeah i mean The first year was getting ready for an IPO and essentially institutionalizing legal ops. ah The two lawyers that I joined, really smart people. Obviously, there's only so many hours in the day, only so much bandwidth. um I came in and I was kind of given like carte blanche to just like start building process in all the parts of our business that we didn't have legal really involved.
00:19:04
Speaker
and It was really exciting. i mean It was also terrifying because I thought, oh, building something sounds fun. and Then I thought, wait, I've never built this kind of a thing before. i think so you know you You pull on, you're like, hey, what have I seen work well? Not from a legal ops for a FinTech company, but more like, how do how do good teams work? right How do you leverage experience? What are the concepts that I think need to kind of permeate the overall presence and reputation of legal within our business? and With the support of our then GC and our AGC, we started to really stake out our role within the business and to educate people like, hey, lawyers aren't just people who draft contracts or say, no, we can't do that. Don't be stupid. Sometimes we say that. Sometimes we do. But you know there's a tremendous amount of versatility that a good business person who also is a lawyer can bring to a company. and
00:19:55
Speaker
you know We've grown from, and I'll get to the to transition in a moment, but we've grown from three lawyers when I joined to eight lawyers now. And you know we've got swim lanes, as I call them, like functions. We have people who are responsible. We have subject matter experts. you know in twenty twenty two In the summer of 2022, I started talking with the then general counsel and others about like my career path.
00:20:17
Speaker
ah That coincided with the general counsel, you know and I had i had worked, you know our general counsel at the time, he was very focused. We had just gone public. He was very focused on our board, supporting our CEO, and really that's it. I mean, it was just like, hey, we're a new public company and no one here has ever done this from a legal perspective. And so he was uniformly putting all of his energy in that particular part of our business.
00:20:41
Speaker
everything else fell to me. So I was, he he used to joke. He's like, we're kind of like code general counsels. Like I do the public company stuff. you So when the time came and he decided, you know, he had been there, he was homegrown. He'd been there for like seven and a half years, almost eight years. He had decided to take a step back and maybe just like spend some time thinking about what he wanted next. And he and our then CEO came to me and said, look, we would really like you to be his successor. And i I'll never forget, our then CEO said, you know can you can you do this job? and I was like, of course I can. like What a silly question. and Then i head I was like, can I can i do this job? right now and you know i yeah and I just was like, look, I'm either going to be wildly successful or I'm going to be a hilarious story for someone to tell someday.
00:21:31
Speaker
And you know the jury's out on what the answer the conclusion to that story will be. But you know thus far, almost two years in, it's been an incredible ride. And what I will say is, is you know given the way that our team evolved, I had the incredible opportunity, like I said, to oversee 80% to 90% of our day-to-day while our GC was focused on the public company stuff. So when the time came and he stepped away, all I really had to do was to learn that. And I was able to backfill some rules, hand things off to people on my team who I trust, who I continue to trust and and rely upon. And then I was like, all right, I'm going to spend a year learning what it means to be a public company general counsel. Because I've now been a general company, at a private company. I've been a DGC at a public company. And yeah, I mean, I read books, I went to seminars, I called friends, I called outside counsel. Hey, is this right? Is this wrong? And you know, thankfully, because as you would imagine, at that level, at this level, you know, the margin for error is much smaller than like a guy.
00:22:30
Speaker
who's in a prosecutor's office trying to get somebody convicted of stealing a TV from Best Buy, right? Like it's a different, the stakes are different. And so I, you know, thankfully given the laundry list of people that I've learned from in my career and the people who have advocated for me and taking time to like teach me, I've had, I think of pretty successful two years in this role almost. and Yeah, I mean, it's it's funny. I'll talk to people and they'll say, your career is so unique, like prosecutor, litigator to public company, general counsel. Like, I don't know that I've ever heard that journey before. And yeah, I wish I could say that this was by design. It definitely was not. I mean, I've made incremental decisions along the way. And I've always opted to to bet on myself and say, look, no one's going to outwork me. There's definitely going to be somebody out there smarter than me.
00:23:19
Speaker
But like I'm not going to leave i'm going to leave it all on the field. right and And I've done that. And again, I make mistakes. Thankfully, these days, they're very small and easily reparable. But um yeah, it's been an incredible ride. And obviously, I'm hopefully you know just in the middle of it getting started. I don't know if it's the right way. I don't want to work till all I'm 90.
00:23:39
Speaker
ah Yeah, it's been a really cool experience. And there's times where I'll kind of pick up my head and look around and think like, Oh, I'm actually doing it. Like I'm doing the job, right? And it's not that like I didn't think I was capable, but I just didn't know. And yeah, I every day is is interesting and unique. But I've got there's an incredible team at infusion, ah both my legal team and our executive team and everybody from the top down. Our board is wonderful. And you know, they have faith in me, they trust me, they look to me to be somebody who's practical and I really enjoy it and it's an incredibly fulfilling way to spend 60 hours a week. so
00:24:15
Speaker
you know i mean Part of that transition is picking up the public company stuff and building the relationships with board members. and and I want to hear a little bit about that. but i'm also curious about yeah You're almost like a peer of sorts to the rest of the legal team and now you become the GC and everyone's boss. and like How do you manage that transition? and how do you you know i'm sure the outgoing GC did a lot of things really well. There are probably other things that you want to do slightly differently, right? um Or new initiatives that you feel like weren't prioritized before that now you do want to prioritize. How do you make that transition well with the team? And how do you own own the role with them? that's That's something that I'm really curious about.
00:25:03
Speaker
Yeah, Tyler, I've never thought about that. I mean, I thought about you know building a team and like operating a team function well, but I've never thought about like, hey, how did they, you know, it was happening to me, right? So I wasn't like, right. And and I try to be a very empathetic person and put myself in other people's shoes. But I will say I think I was so hyper focused on like,
00:25:22
Speaker
not dropping the ball in my new role. And I was like, Hey guys, like, I'm going to be over here joining, you know, jump in the water is fine. And I like to think that the success that I've had, we've hired as we've gone, but like, we have not had anybody on my team um since I took over leave.
00:25:40
Speaker
like resign. That's amazing. Yeah. Yeah. And in the continuity, that's it's incredible. Yeah, the continuity is incredible. I'm in it. I don't take credit for that. i I try to lead and build a culture of like, look, guys, like I guys, girls, men, women, like I am someone who will do anything that I asked you to do. And odds are like, if you're busy, and I can just do it without you even knowing about it, I'll do it. Like,
00:26:04
Speaker
Many of our templates and our forms that we now use for various parts of our business, I create it. I draft it. i And I will have people come to me and be like, hey, when you created this. And sometimes they'll be like, look, I think we should do this differently. And I'm like, have at it. like Own it. like I trust you. You're here for a reason. And I try to lead through like empowerment.
00:26:24
Speaker
and giving my team agency and saying, look, and I've said this on many occasions, and not just because it sounds cool to say, but it's like, look, if there's credit, it's yours. If there's blame, it's mine. And you know presuming that if they've got something from start to finish, they know what they're doing.
00:26:42
Speaker
If at some point in time they bump into something that's unsure, bring it to me. If I co-sign on something or I'm like, hey, let's do it. I'm comfortable with that risk. If there's an issue at some point and the CEO's like, what happened here? That's me. And yeah I tell them like, look, I, you know, there's a, there's a saying heavy as the head that wears the crown.
00:26:58
Speaker
it is absolutely like it captures and the but the great thing is you know I find myself on a consistent basis like just reacting you know if you ever read the book blink about just making like yes vision like there's also another book called you know think fast think slow I think is what it's called and um or maybe something some version of that but it's about making decisions from a place of like confidence, but also your gut, which, you know, from everything I've ever read, your gut is the combined, you know, central processing of every experience you've ever had and every lesson you've learned. And so I find myself as DGC, for example, to kind of juxtapose the two, maybe I was making 25 to 30 decisions a day, I probably make 100 a day now.
00:27:44
Speaker
And right i don't I don't allow myself to kind of get paralyzed by the analysis of things. But huge part of that is I'm incredibly lucky. My team, i I have three direct reports. And even the people that are not my direct reports, I just came off of a call with one of them right before this. And I had forwarded her an email yesterday and I was like, hey, I don't even have a minute to look at this. I will.
00:28:06
Speaker
Could you like take some time and read through it and like, let's meet tomorrow. And we got on this call, Tyler, and she was like, I've read it. I pulled the supplemental materials. I've analyzed the issue. There's two questions. Here's what I think we should do on both. I asked her a couple questions and I said, I agree with you.
00:28:24
Speaker
let's do that on both. And I just was like, unbelievable. Like from a user experience for me. Yeah. And that's like one of the more junior lawyers on my team. And, you know, I'm, it's incredible that like, I have the opportunity to continue to learn from people, like people that have been practicing for three years, right? Like they just have different experiences. They came from different places. And I think that's a huge value add for anyone who's a lawyer or any profession.
00:28:49
Speaker
Like, keep learning, right? Keep being open to the fact that you don't know everything. And you wouldn't know it from how much I've been talking on this podcast. But I'm a big believer in if you're talking, you're not learning, right? And that's, there's a lot to learn. Everybody you encounter has something to teach you, good or bad. The abstract is brought to you by Spotdraft, an end-to-end contract life cycle management system that helps high performing legal teams become 10 times more efficient.
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Speaker
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00:30:12
Speaker
straight advice that is practical, that thinks about risk but doesn't just think about risk, that also thinks about the business. Are there ways that you build that mindset or build that as a culture within your legal team, ways that you sort of help set that tone so that way all those other folks on your team are out there talking to the business in the same way that you are?
00:30:34
Speaker
yeah Yeah, absolutely. um Part of it is I think hopefully some of it is but leading or demonstrating that through my own behaviors. um Part of it is we're very rigorous on how we hire. And so i don't I don't look for a valedictorian or an Ivy League graduate. I look for somebody who has practical real world experience. And look, I'm a guy who couldn't get OCIs in law school and I went through a prosecutor's office and I made $40,000 a year for a couple years like trying to pay a law school debt. I don't view there to be one path to being an effective lawyer and I definitely don't view that as the case when you're thinking about being a business person who was also a lawyer as an in-house counsel.
00:31:17
Speaker
So we've been very fortunate to hire people who I think have a similar mentality to the one that I possess, which is like our job here is to facilitate the business and allow it to execute its strategy and to operate. So I tell my team, start from yes and then work backwards. Don't start from no and have them convince us that we can do this in a way that because no is where lawyers I think tend to want to start from because it's like, I don't know anything about this. So until I understand it and I'm comfortable, I can't say yes.
00:31:45
Speaker
right I always say conceptually, meet them at yes. And then more often than not, where we get Tyler is, yes, let's do that. But instead of A, B, C, D, let's do A, D, G, Y. right like totally Same outcome. We're sidestepping some legal, let's call them landmines. um And I always tell my team, people you know we're lawyers. A lot of us have you know God complexes.
00:32:10
Speaker
As far as like, Hey, you don't understand. I went to law school and I joke, but I mean, lawyers tend to have egos, right? And they think like, Oh, let me tell you how the world works. And it's like, look, the business, they know things about things that I'm never going to understand. And so I never, I tell my team lead with like, why, you know, there's a, I think it's Simon Sinek book, start with. Yeah. Like go into every situation.
00:32:33
Speaker
open to learning something from the other person, not just trying to be like King Solomon who says like, here's your solutions, but the baby, right? Like that doesn't help. And and it's not like legal advice is not one size fits all. It's very fact intensive. The other thing to your question about, you know, facilitating and acting as a business partner rather than a lawyer or like a brick wall is I always, I always tell my team, I was actually just on with our COO earlier today and I was talking with him about this.
00:33:01
Speaker
This is advice I've given my team. This is actually advice that I gave my 14 year old son recently. I said, that we do as humans, as lawyers, as business people, every situation we encounter, we have three choices, right? One is make the situation better, like help solve it. One is walk through it without any impact, you know, neutrally. Or the third is leave it worse off than we found it.
00:33:26
Speaker
and i told my son i told my my team i told my colleagues we should never leave something worse off than we found it ever and if we walk through something and we look back and we realize we did double back and and clean it up at a minimum.
00:33:39
Speaker
let's be neutral, right? There are going to be situations where somebody comes to us from the business and they just don't know what they've got. And they're like, I wanted to talk to legal because this is written on paper and papers contracts. And I'm like, look, this is not for legal. Like go talk to that person. and that's Sometimes that's the case, right? But yeah like my default, and I tell my team their default, and I've told my kids their default should be add value. And when you think about the value of why we're here,
00:34:06
Speaker
We're not here to say no. We're not here to eradicate every risk that a business might bump into. We are here to facilitate the execution of our strategy. We're here to help the company return value to our shareholders. And we're here to make sure that when people are making business decisions, like our CEO, other executives, that they are fully apprised of risks. And they have a sense of, hey, not only am I going to give you a roadmap here on how to do this the right way, I'm going to actually co-pilot with you. And we're going to move this together.
00:34:33
Speaker
and I'm going to own this through the end, not because I don't trust you, not because I don't think you're capable of handling it, but because I care and my commitment is to our business. so i think it's I'm a big i'm a big um acts of service person. think that's like I think that's my love language someone told me once. and I think that actually suits in-house lawyers' roles well. How do you serve a person that's coming to you? No one ever comes to a lawyer and says,
00:34:59
Speaker
Hey, no problems here. Everything's great. Just wanted to tell you, have a good day. No one comes to me and says that. People come to me and they say, my world's on fire or hey, everything burned to the ground. What did we do? Or I want to do this thing and I don't want to start a fire. And it's funny, I think I was a third year associate and I was telling a colleague of mine, I'm like, why does everyone who calls me have a problem?
00:35:21
Speaker
like He's like, are you serious? And I was like, yeah. like I was legitimately exasperated. And he was like, you're a lawyer, man. like That's what people go to lawyers for. People don't come to lawyers for like high fives. right They come to lawyers because they're like, hey. I got a problem. Either I might have a problem and I want to avoid it, or I do have a problem and I need you to help me solve it. So that has been you know what I've preached probably too verbosely to my team, but I'm just like, look, let's add value. Let's find ways to lift up our business partners.
00:35:52
Speaker
Let's protect the company. And if we have to say no one out of every 20 times, say no. And what I have found, Tyler, and this is an incredible, like you have ah you have a concept and you're like, I think if we can get to this point, then I have to say no. People will be like, yeah. and And what I've had people say to me, to my team is, you know what? You guys never say no. The fact that you're saying no right now, this conversation can be done. like I get it. like If you're telling me no, you will turn over every rock to find a way to help do what I need to do. If you're saying there's no way, there's no way. And that has manifested itself time and time again in my life and my career here at Infusion. And it's great to have that sort of trust and ability to collaborate with people and that they'll defer to you and not just say, oh, well, you're being too conservative because you're a lawyer. And I tell people, I'm a business person who has a law degree.
00:36:44
Speaker
I'm responsible for legal risk, but I'm not special. right people Somebody here who's an accountant doesn't just sit there with an abacus all day. They have to think about how numbers they think about how those numbers influence the business, right money in, money out. and so I think that anybody who's thinking about the transition to being an in-house lawyer, if you feel like you would like to stretch some of those muscles and not be purely kind of more academic and not that all law firm lawyers are academics, but you know you go to a law firm to be a specialist, right? Oh, we're going to charge you $1,000 for this person's time because there's 10 people in the country that know this much about this area of law. yup you get You go into a lane and look, people have had incredibly brilliant storied careers doing that. It wasn't for me. I was like, look, I need a little more variety. I want to really continue to evolve. And yeah, the move-in house has absolutely helped me realize that.
00:37:32
Speaker
I think one of the things you're sort of talking about is having an owner's mindset. like i am a part of This isn't my client who I'm advising and if they walk away and they don't take my advice, like who really cares? I'm going to invoice them and they'll pay me. yeah Whatever. um I am curious. i you know i I try to ask this to a few different people. like How do you hire for that? ah How do you actually uncover someone who you think is going to be an owner or someone who you think is going to be practical as a part of the hiring process? You seem like a very thoughtful guy. I'm sure you've thought about like how do we actually evaluate candidates as they're coming into the pool for these these roles? Yeah. I think, you know, one of the gating questions we asked Tyler is just like, why do you, you know, if you'd ever been an in-house lawyer before, which we have a lot of people on my team who came from law firms, I say, why do you want to be in a house lawyer? Right. And I've heard, shockingly, I heard the hours are less, more work-life balance, like all the bottom.
00:38:31
Speaker
I'm like, number one, yeah that's false advertising. like number You're not keeping your time in like six-minute increments, but like you have busy weeks. you know and and There are times where this job is as demanding as any job I've ever had. ah um so you know Why do you want to do this? right like What is it about working at this company in this sort of a role? and Then I do a lot of questions that I think probably different leaders on my team have different you know ways that they approach it.
00:38:57
Speaker
but we've talked about this. like We want people who want to like think beyond, you know oh, well, I feel like at a, you know and I've heard people say this, at a law firm, everything is very reactive. You're a hired gun. like To your point, you give advice, they hang up the phone, you're like, I don't know, phone rings again, it's a different client. Whatever happened with that thing, I don't know. There's no accountability. I mean, you can lose ah you can lose a client if you're not giving them good advice, but like you know when I was a law firm lawyer, I would work on 50 different clients' matters a year, and I cared about each of them.
00:39:26
Speaker
I didn't really know any of them. and so When people come to me and they're like, hey, I really want to know this business and I want to get to know this client like inside and out and I want to understand. so you know Again, the best lawyers that I know are able to, on an active ongoing basis, absorb information and pivot their thinking efficiently and fluidly. And you know we do a lot of i do things. I'll say, like hey, if you got this, we have ah we actually have a question, like ah almost like a hypothetical that we give. And it's ah when somebody gets past a certain level of screening, it'll say, hey, you are at lunch with your new head of HR.
00:40:01
Speaker
And in that conversation, she says the following. And then it's like, spend no more than 30 minutes and give me an itemized list of every issue that you feel like you have to leave this lunch and go look into. and Interesting. Yeah. And you'll get like novels, like law school exams, you'll get like just buzzwords. And each one's different. And it's funny, I took that, that was part of my interview process.
00:40:26
Speaker
And I did it and the GC, my predecessor, called me. ah Well, the talent acquisition person called me and was like, hey, you know our general counsel would like to talk to you. And we got on the phone and he said, can I ask you a question? And I said, yeah, of course. And he said, how long did you spend on that? And I said, six minutes.
00:40:46
Speaker
And he basically, I mean, it didn't go quite like this, but if it was like a movie, it would have been like, his next question was like, when can you start? And I think he was thinking, look, you are in a pressure cooker, right? And not to add a analysis or a critique of law firms.
00:41:02
Speaker
But if there's 10 hours of work that you can justify, you're going to do 10 hours of work, right? It's directly tied to your revenue. and And there are ethical boundaries, and I know lawyers are very good about that. In my experience, I'm sure there are people who push the line. I do not want to stretch anything out beyond one more second than I need to because I have 20 other things right behind it. And yeah so decisiveness an ability to make snap decisions once you know that you've given something to do amount of attention and so this example that we use. To me is and i can i understand why my former my predecessor was like how long did you spend on this and i think you know and and we never talked about it but i think his thought was this is impressive.
00:41:44
Speaker
assuming he didn't spend three hours on it. Right. And I was like, yeah, seven minutes. And he's like, really? And I said, yeah, why would I lie about that? Like, that's not, yeah hopefully it doesn't look like I did it in seven minutes because that means that I, you know, he's like, no, he's like, look, you grabbed every meaningful issue.
00:42:01
Speaker
And you did it in a way that's reflective of the pace of what we do here. And again, you got to be and smart enough and aware enough to issue spot. But you also have to be like thoughtful enough not to overspend resources because it's just not a luxury you have. So it's a blend of a lot of things. I know I've given you kind of a few different pieces to that puzzle.
00:42:21
Speaker
Yeah. And it's an art, right? It's not a science. And again, I'm sure at some point we're going to make a run higher and we'll come back and it'll haunt me. But we've been incredibly lucky so far. And we tend to have every candidate. We have a small team. We have every candidate meet every person on the team, either for a substantive conversation or we'll do like a three on one. Let's get to know people.
00:42:39
Speaker
In person. ah Sometimes in person, sometimes in Zoom. It depends. Yeah. yeah um But we you know we have conversations. And I'm just like, hey, like tell me about how you spend your time. And at the end of the day, like we're all human beings. And I don't want a robot. right like AI is coming. That's the AI when it gets here. like I want somebody who's going to be thoughtful and human. And yeah, like i I've said many times, like leading this team has been the honor of my career. like They're some of the smartest, kindest,
00:43:09
Speaker
hardest working people I've ever met. And I'm lucky to call on my colleagues. And like I said, I could give you 10 examples of things I've learned from people on my team today. And these are people that report to me, right? You think of a boss. It's like, well, you should know everything. I don't know everything. I know that I don't know everything. But yeah, I think you know trying to lead that way, trying to empower people to be thoughtful and help people not be scared of the consequences should they try to reach for something as a business person, which isn't a natural muscle for a lawyer.
00:43:38
Speaker
And then knowing, hey, if you fall down, I'm going to pick you up. And if there's consequence, I will be standing in front of you, right? like in that I think it gives people a confidence that they can get out there and and really try. so This has been a great conversation, Matt. I've got a few fun questions for you that I like to ask all of our guests as we start to to wrap up. Sure. The first one is, and what's the your favorite part of your day to day? I mean, you probably have a lot because we've had such a great conversation.
00:44:08
Speaker
yeah i love the people i had a lot from you got a ton of smart people but they're all. Kind of versions of each other unless you kinda dig down and get to know people at a human level here it's like you got like technologists and you got people who are hr professionals and you got finance people and it's like.
00:44:26
Speaker
the diversity of yeah backgrounds and like the lenses through which they see the world. like I will be on call sometimes and i and I'm just like sitting there listening and I'm thinking like, this is fascinating to me. This is not at all, and less so now that I've been in this role for a couple of years. But yeah I can remember early on and just really smart people and people who want to do good work, who are passionate and care about the outcomes of things. And yeah, I mean, just honestly,
00:44:53
Speaker
nice people like just even nice nice is something you can pretend to be the kind people who are kind and yeah people who like actually give a damn about like what their work says about who they are and they take pride in those things collaborative there's not a ton of ego you know there's a lot of like let's just get to the best outcome and yeah I mean I joke I mean we've been laughing here a little bit I joke with my team constantly like we have a We use Slack, and so we have a Slack channel, all eight of us, and it is nonsensical, like the things that we joke about. I mean, it's all, you know, it's business. I mean, it's all professional. Yeah. Workplace appropriate, but still fun. Thank you. That's the words I was looking for. workplace Workplace appropriate, but like just nonsense. And, you know, it allows us, you know, any given day somebody will be like, hey, random question of the day. And then it's like,
00:45:41
Speaker
If you weren't a lawyer, what would you be? And then it just goes on these crazy tangents. Like what was the worst job you've ever had? Don't say infusion, right? Like we're just like, you know, and it's just, it's great. And we all, you know, it's Slack. It's sitting here on my monitor all day. A lot of days I don't look at it until like bedtime. And then I'm like, Oh man, I missed some great stuff today. You know? And, uh, but I, I'm definitely the one to get in there and like heart something and, you know, and be like, Oh, this is great or hilarious. Or, you know, my, I, my daughters, I have a first grader and a fifth grader. They had the first day of school today.
00:46:09
Speaker
I took pictures of them. I sent them to my parents. I put them on Slack and everybody was like, here's my kids on their first days. And next thing I know it was like 12 pictures. And I was like, you know what? At the end of the day, we're all on our deathbed or we're all, you know, what are they shuffling off this mortal coil? like It's not going to matter how many issues I solve it in fusion. This is a means to an end. I care about it. I'm passionate about it. I take pride in what I do. But this is something to facilitate, like living life. And, you know, like I said earlier, I'm very lucky to be in the role that I'm in. But yeah, the people are just absolutely wonderful.
00:46:43
Speaker
What was the worst job you had? That's a good question. I might have to work that into my podcast scripts from now on. So it's a good it's like it is a good question. So growing up, my mom, who is one of the most amazing people in the world, ah she'll be listening to this. So that will mean a lot to her that I said that. That's cute. She worked at a hotel growing up. She was like the front desk manager, ah bookings, incoming, outcoming. She's an incredibly,
00:47:11
Speaker
personable. I get a lot of my energy and zest for life from her. And I had had a job for a couple years, not at a hotel. And I had come home from college and she's like, hey, instead of going back to this other job, which you've done for a couple years now, like come work at the hotel. And I was like, what would I do?
00:47:27
Speaker
And i was nineteen twenty maybe hot at a car she's like well there's like a facilities manager and i was like manager sounds cool like i didn't know what that meant i was like. cool so I showed up day one it was like beginning of june is chicago summer but for some reason it was like the dog days in june.
00:47:45
Speaker
and It was like 90 degrees and it was an older hotel, so their conditioning wasn't great. I walked in, I was immediately sweating. and i was like and I was like, hey, mom. and She's like, hey, go find so-and-so. He'll be your collaborator here. I went and I found out that Facilities Manager means janitor and no no offense no offense to janitors. like Everybody has to earn a living. My dad started out his career at a company he ran for many years as the janitor. and so yeah wow yeah and so I did it for like an hour. and I went to the front desk and I was like, mom, like I don't love this. and She's like, why? and i was like i I'm not a mechanical person. They want me to to sweep for the pool and fix a faucet. And I'm like, I don't know how to do this. And she's like, well, what do you want to do? And I said, I want to quit. And she was like, really? And I was like, yes. And I quit. And I quit like two hours after I started. And so that's an unfair, to say it's the worst job I've ever had because I really didn't do it. He didn't have the job for very long.
00:48:51
Speaker
But I honestly, I actually think that what I did was noble, because I think we all need to be very honest with ourselves about our shortcomings. And they were never going to get the ah ROI from me that they deserved. And so I did everyone a favor. And I went home, and I slept the rest of the day. And then I went back to my old job, and I worked there all summer. So so um I worked two hours as a facilities manager at a courtyard by Marriott in Waddell, Illinois, back in 1997.
00:49:17
Speaker
slightly different type of management. ah Very different. your currently Absolutely. I'm always looking for good books to read. Do you have a book recommendation you want to share with the audience? So yeah, I mean, i'm I've got two, um I usually have one or two books on my desk at all times. One is a book that my brother who is a lawyer, he actually is a lawyer at IBM. um He, I'll hold him up here in case people need to see what they look like and they want to buy him. What is called the psychology of money? I think it's a pretty well done book. And it's about how people think, you know, wealth, greed, happiness are,
00:49:52
Speaker
scientific things, a lot of how you manage money, investing, how you run a budget, how you invest, all those things is more emotional than it is like not emotional, I guess, or practical. haha well I'm reading that, it's great. And then the other is a book that I'm reading for I think the third time. um And my mom, the aforementioned front desk manager at the court, Rabbi Marriott gave me this book a few years ago.
00:50:15
Speaker
It's called The Mount of Olives. hi it is The subtitle is 11 Declarations to an Extraordinary Life. and It's definitely the furthest thing from like a self-improvement book or anything like that. But the thread of the book, and I'll keep it very short, is there is a this this takes place hundreds of years ago.
00:50:35
Speaker
There is a young man who is a soldier in the Roman army and he is he's deaf. I've read it multiple times. and I just actually picked it up again yesterday. He's an orphanage. He's in an orphanage and he gets older and he leaves. But as he's leaving, this young girl tells him she treats him very kindly and basically, he plants all these olive seeds before he leaves on the hills of Rome. And this book takes him on this journey around Europe. And he kind of learns about life and how to treat people when he meets fishermen and people like that and mothers and things. And he comes back, you know, I think 10 years later, and he's like a different man. And you find out and I didn't know this. But apparently, when you plant an olive tree, it takes anywhere from like six to 10 years to bear fruit. And so the whole idea of the book is like,
00:51:23
Speaker
do the things now to give yourself a fuller, more like robust future. And yeah, I've read it now. This is the third time. it's an incredibly it'ss I'm not an overly spiritual person. you know i i I was raised Catholic. I went to Catholic schools. I don't attend Mass regularly to the extent your listeners listeners were curious.
00:51:42
Speaker
But I'm a pretty faith-based guy, and I always feel like you know there's just there are tried and true ways to live life. And this book is a good reminder. It kind of anchors me a little bit. And so, yeah, anytime I'm feeling like whimsical or reflective, I always grab this book. and And again, my mom is listening. She's going to be like, I gave him that book. So thank you, mom.
00:52:05
Speaker
Perfect to pick it up right before a podcast like this. Exactly. Speaking of reflective, my last question that I like to ask all of our guests, and that's if you could look back on your days being a young lawyer, maybe just getting started as a prosecutor or just graduating law school, something that you know now that you wish that you'd known back then. Yeah, i it' so that's a great question.
00:52:35
Speaker
I think what I would say is it's okay to doubt yourself. like I feel like lawyers are often times perfectionists. I am absolutely someone like that. i have It has taken me 18 years now practicing to shut to start to be able to show myself like grace. and When you're young and you doubt yourself because you don't know how to do something or you've never encountered it, you start you know if you don't harness that energy the right way, the self-talk becomes You're a fraud. You're an imposter. I remember my first two years at Freeborn and Peters, I was like, they're going to fire me today, like every day. And then I would get the review and they would be like, you are our top second year associate. i think ah you guys like You guys are messing with me, right? like i that's And I honestly, and eventually you start to think, oh, there is I'm learning. Everybody's figuring it out, right? We go back to your comment about the practice of law. And I think
00:53:32
Speaker
when you doubt yourself when you're young, you push it down, at least I did, and you don't allow yourself to just like kind of live in that. And so I think my advice to myself when I was a prosecutor, um when I was a young litigator, don't be afraid to doubt yourself, like explore where that doubt comes from, and then make a conscious choice to like lean into that and attack the things that cause that doubt, right? Whether it's a lack of experience or a lack of like, not value, self worth, you know, any a number of doubt comes from so many different places, right? And I know every single human being has doubts in some shape or form. um But yeah, I think
00:54:11
Speaker
people view doubt as a negative thing. And it is, I think, conceptually is not great. But like, it's not going anywhere. It's like fear, right? Like, you're always going to be scared of something. but You can choose, like, do I ignore it? Or do I, like, double click? And do I like dig into it? And do I use that as a method or a tool to be better? And I think doubt, for me, when I learned to have a healthier relationship with doubt is when I feel like I started to really accelerate my growth as a lawyer and as a person. So I love that answer. That's a ah great way to end this conversation. thank you Thank you. Thank you so much for joining me for this episode of The Abstract, Matt. This has been a lot of fun. Thank you so much for having me, Tyler. Again, I really appreciate it. Thank you. And to all of our listeners, thank you for tuning in to this episode of The Abstract, and we hope to see you ah next time.