Leaving the GC Seat: Matt Gipple of Dryvebox on Product Judgment, Regulation, and Becoming a Founder

Matt Gipple, former General Counsel of Cruise and now co-founder of Dryvebox, talks with Cecilia about his the transition from legal advisor to decision-maker.

Matt shares what it was like to join Cruise in its earliest days - working out of a garage, interpreting California’s first autonomous vehicle regulations in real time, and helping shape how disengagements, reporting, and compliance would work before there was industry consensus. He explains how product counseling actually happens when the law is unclear, regulators are learning alongside you, and company culture matters as much as the rules on the page.

Cecilia and Matt also explore the GM acquisition, including the moment a single IP term in an investment proposal changed the outcome of the deal entirely, and what it takes to preserve a startup’s operating model inside a public company. From there, Matt reflects on leaving the GC role to become a founder. He talks about why being a lawyer is often easier than being “the person who decides,” and what he misses (and doesn’t) about legal work.

The conversation closes with practical insights on hiring, working with engineers, learning from non-lawyers, and how AI, much like autonomous vehicles, reshapes how humans apply judgment rather than replacing it. This episode is a grounded, insider look at leadership when there is no playbook.

Follow Matt:

@Matt Gipple on LinkedIn

Show notes:

• Joining Cruise before autonomous vehicle law was settled
• Interpreting California AV regulations without precedent
• Product counseling in genuinely regulated innovation
• Disengagement reporting and judgment under ambiguity
• The GM acquisition and why IP terms quietly matter most
• Operating a startup inside a public company
• Transitioning from GC to founder at Drivebox
• Hiring realities: doers vs. deciders
• Learning from engineers and non-lawyers
• AI as a judgment amplifier, not a replacement

Ideas & Takeaways:

• Product counseling means manifesting legal advice in systems and workflows
• Culture shapes how ambiguity is handled as much as regulation
• Founders decide; lawyers advise, and the distinction matters
• IP terms can define control more than valuation
• AI increases the surface area of thinking, not its disappearance
• Some of the best legal solutions come from non-lawyers closest to the work

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Transcript

Matt Gipple: 0:00

That was my input to the term she this is my side of the story. I'm sure there are other parts of it too. But like that's my my hook in the deal is like we went back to GM and said, like, hey, you know, this we're interested in an investment. This IP thing doesn't work. Like, if you want this kind of IP, you need to buy us. And then GM was like, well, let's talk about that. And that was kind of like, whoa, we did not anticipate that being real. Uh it was kind of a straight comment, like, oh, if you want that, like you got to buy us. Like you bought the company's uh we are the IP and you're buying it with an investment. You're gonna have to actually buy the company, and they said yes. Um Wow.

Cecilia Ziniti: 0:44

Welcome back to CZ and Friends, where we talk with legal leaders, technologists, and operators shaping how modern companies work and scale. I'm your host, Cecilia Ziniti. Today I'm joined by Matt Gipple. Matt started his career in Big Law, moved in-house, and became general counsel of autonomous vehicle company Cruz during a period of massive growth. He also at the time was actually my boss, and I learned a whole lot about product counseling, being a general counsel, innovation, and working in regulated spaces from math. Then he made a pivot that a lot of lawyers, a lot of folks listening probably are um going to be inspired by. But basically, he became a founder. Uh, today he's the co-founder of Dry Box, which brings uh golf everywhere through mobile technology-enabled experiences across the US and Canada. It's been super fun to read his investor updates from the other side. So, this conversation, so excited to talk with Matt. Been wanting to have him on the podcast since I started. Um, it's gonna be about moving from advising to deciding, leading through ambiguity, um, building when the answers are not obvious. Uh, Matt's gonna be super humble about it, but essentially the rules on autonomous vehicles in California, he basically kind of wrote them. So it's super exciting. We're gonna dive into that. Matt, it is so great to have you.

Matt Gipple: 1:58

Yeah, thanks for having me. Um and looking forward to seeing what we get into today.

Cecilia Ziniti: 2:04

Awesome. Let's go. So you started off in big law. Uh, you were at Latham and Watkins, and then uh basically you got a phone call. What what happened?

Matt Gipple: 2:14

Yeah, yeah. I was actually so I went to Latham and then I was clerking and I had every intention of going back. Um, I liked it there. I was doing antitrust, it was interesting stuff, remains interesting. Um, but it's like always relevant. It's kind of it's I didn't realize that when I got interested in it. But anyway, um, yeah, my friend Kyle had started this little company. Like literally he was living in San Francisco and he had a garage as one does, and or some people in San Francisco do. And uh he's like, You gotta come look at this these robots I've been building. It's like, okay, sure. Kyle's been building robots forever. And by the way, this is Kyle Vote, the founder of the Kyle Vote. And he was like, You know, I started this self-driving car company, and my investors keep asking me these legal questions, and I don't want to answer them. I don't know how to answer them. They're kind of annoying. Can you come answer these questions for me? And I said no. Um, because that that was like high risk. I don't like no, I have a nice thing. You get a bonus when you go back to Latham from clerking, like, all makes sense. Um and yeah, he worked on me a lot. Uh, and just like eventually he said, he's like, look, if you come do this, like what's the worst thing that happens? It fails, and then next year Latham takes you back, and then you're better. And that that worked. I was like, oh, you know, that's a good point. So then I said yes. Um, and the rest is history.

Cecilia Ziniti: 3:41

So you basically join what would become, you know, really a a true innovator in autonomous vehicles on faith and on convincing from Kyle. So, so what was it like walking in that first day? And you've got these basically sounds like souped up, was it it was Nissan's at the time, I don't remember, but anyway, souped up cars. And you're like, all right, let me pull out some case law, or like like, what did you do?

Matt Gipple: 4:08

Yeah, it was so to be fair, Kyle, like he's always been like the the guy who was gonna do big things. And at that point, he had they had just sold uh he just sold to Amazon um Twitch, just sold Twitch to Amazon for you know a billion dollars or whatever. So it was like not that large of a leap of faith. Like he's already the Midas Touch character. But I was I was more or less oblivious to this. Like I knew about these things, but I wasn't like in tech. But yeah, like even growing up, like Kyle's this achiever. So it wasn't that big of a leap. But yeah, like you go from law firm to clerking, like pretty structured, pretty known environments to like it was 25 people in this modified house that happened to have a garage because we have cars. And Cruz had just they started out with they were gonna do a highway autopilot, um, and changed between me saying yes and starting, they changed. Uh so like I didn't know that until the day I showed up. I was like, oh, full self-driving, got it. Um and they had a a gem, like the golf cart, the fancy golf carts, uh, as well as a Nissan leaf at the time. And it was like, what are we gonna do? Are we gonna do low speed people moving type stuff? Are we gonna do full-on self-driving everywhere? So what did I do? Um California's regs had just like the first wave of them had just come out. And we were deciding, like, do we need to apply for one of these? And it wasn't clear that you did, because like one could argue you don't, because you can you can make a bunch of different you can put some things together to say you don't need to. And that was kind of my first thing was like, hey, do we need to get one of these permits? Um and decided that we did. And then the next year was how do you one of the big parts of the California regime was reporting uh accidents, which is fairly clear, and then these takeovers. Um, and like what counted? It was not clear. No one had reported before, and we all had to report the first time. And there were like seven companies doing it, fix six or seven, like Mercedes was in at the time, Tesla, Tesla reported none. Uh Waymo or Google at the time was doing it, and we like all everyone else landed like fairly close to the same manner of figuring out what to report. Tesla reported zero. Um, so but no one ever said, or as far as I know, has said like what counts for them. So that was an interesting endeavor trying to figure what would count for us.

Cecilia Ziniti: 6:44

So in that process of this ambiguity, so this is like a real, this is like a law school hypo. Like literally, what is uh is the official term is disengagement, or what was the official term? Okay, so what is a disengagement? So I now so I happen to drive a Tesla now. So now we've got the benefit of hindsight because we're uh what is it, 10 years later or maybe eight years later. And uh, well, I'm gonna admit that I turn on self-driving, and when it yells at me, it's like, look at the screen, I turn it off because I know that if you get yelled at twice in one drive, it will turn itself off. So I am, I guess I'm gaming the system. But going back to actually being um a lawyer for this, how did you do it? So did you literally like pull up the regs? Did you call the regulators? And is it, you know, what is the standard that you apply? Like, I mean, I know what I would do, but is it something like, okay, what's reasonable? What's the goal of this regulator? Like, give us a lot of our listeners are in product counseling. This is, I would consider this to be product counseling, you know, on hard mode. What what are the what frameworks did you use at the time? And then um, maybe you can get into what you learned over the course of working it, Cruz.

Matt Gipple: 7:54

Yeah, so and I don't remember perfectly, so I'm gonna I'm gonna remember what I remember. Like you kind of do the like legislative history work where you look at when they were making the reg and what was talked about. So I did that. Um it was the the building of that, so you started like, oh, Matt wrote the red. Like Google, they they tried to get a law passed uh like in 2011-ish. Um eventually got some things done that led to these these regs coming out from the DMV. And so there's there's a couple uh couple guys at the DMV who wrote the red, like they wrote them, they were tapped. There's there's a story published about this. Like the they were doing something at the DMV, I don't remember, and they got tapped to like build the regs. Um and really at the time, Google was the only one uh like giving input as to like what this was about, educating them. And I think, you know, they did a pretty good job uh being the first out there. Anyway, so they did that and I looked at this history, and then they were taking comments on the the future iterations of these regs. There were like three tiers or two tiers that needed to come out for testing and then testing uh without drivers and then paying without drivers. Anyway, so I did like get involved in some of that. Um, but yeah, you I looked at the history. I didn't, I I definitely called, I think his name's Brian. I can't remember, but I I like had his phone number at the DMV. And I I had called him for other purposes, but not to ask him, like, hey, what what am I supposed to do here? Um then at I think in other places you may have industry groups where like you can get together and talk about it. That was not the case here. It was still too early, like no one really wanted to share what was going on. Um another piece which is like relevant is like what kind of company are you? So like we you knew Tesla was gonna say zero before you know the things got started. Like that was gonna be the answer. Um so you kind of have to like you you talk with your founder and your leadership um about what's going on. Like, hey, here's the situation, here's what the rules say, here's what I think. And ult you're there, you're gonna be guided by that as well. So that was for us like Kyle's a pretty reasonable person. He's like, that seems to be what it says. I your approach makes sense. So that was kind of where we went.

Cecilia Ziniti: 10:19

Interesting. We had uh Jordan Breslow, who was uh GC for Ben Horowitz at ObSquare on the pod, and famously essentially went through the exercise that you just described of like, here's the rules. And the the question there was about stock option dating. And Jordan's conclusion was like, hey, look, I've read this nine ways to Sunday. I don't see the interpretation those are taking being real. And at the time, Ben Horowitz agreed and said, you know what, cool, don't do that. And famously, of course, Ben now says that that kept him out of jail. Amazing. So put us in that moment, the conversation with Kyle, it sounds almost relatively casual. So you you go into this meeting with Kyle. He's a billionaire already at the time. You're looking at the cars, you're in this garage, and you're like, you literally pull up the rag and you're like, all right, disengagement says, you know, a human, you know, clicks on something or whatever it says. I think that means XYZ. Um was it just that casual? And then how did you adjust over time as the cars were literally on the road?

Matt Gipple: 11:24

Yeah. And it another note about this is like the report wasn't due, I think it was due like end of the year. But obviously, you need to be tracking your eligible disengagements beforehand. So like the law, it went into effect in the spring, I think. And we needed to know what we were doing to track because it was subjective. Like it from from like, at least at that point, the state of the tech, as well as reading the reg, like it was kind of subjective assessment of like, are you going to get in a like, did you avert a crash by taking over? Was was I don't remember the words exactly, but something like that. And simulation at that point, like wasn't good enough, at least for us, to say, like, oh yeah, we definitely avoided a crash. So like you actually needed to ask the person taking over, do you think that you avoided something? Um, so we need we need to give them the standard. So the standard actually like sat with with our operators to some extent for some for like a some period of time. And so, yes, this was happening pretty quickly. And you know, I think it's a big deal. Like, I'm the lawyer in the room, and like this is the only thing I've got to go with, and this is important. Cloud has nine million other things that are very important as well. So I like I get in the door, I talk about these regs, we talk about it, he becomes familiar with it, starts hearing about it. It's like, okay, like what are we gonna do? So, no, it wasn't like some big thing where we sat in a room and uh had a big PowerPoint presentation. It was like, here's what I think we should do. I was like, Yeah, that makes sense. Go make sure that happens.

Cecilia Ziniti: 12:57

Love that. Any other moments from Cruz just really stand out for you?

Matt Gipple: 13:04

Um us being acquired certainly stands out as it should. Um that so as is common, I think, like GM had been sniffing around in the context of an investment. Um they yeah, they sent us a term sheet, and yeah, I was like pretty brief, you know, it wasn't even like a full-on formal term sheet, it was kind of a one-pager. But it had this IP term in it, and it was like crazy. It was basically like they're gonna own our IP. And so, you know, lawyer hat and hat is like, hey, this like doesn't work. I like that was my input to the term sheet. And this is my side of the story, I'm sure there are other parts of it too. But like, that's my my hook in the deal is like we went back to GM and said, like, hey, you know, this we're interested in an investment. This IP thing doesn't work. Like, if you want this kind of IP, you need to buy us. And then GM was like, well, let's talk about that. And that was kind of like, whoa, we did not anticipate that being real. Uh it was kind of a straight comment, like, oh, if you want that, like you gotta buy us. Like, you bought the company's uh, we are the IP and you're buying it with an investment, you're gonna have to actually buy the company, and they said yes. Wow.

Cecilia Ziniti: 14:18

So, so so folks read term sheets and as a founder hearing that too, that like, because the thing is IP, like, I've lived and breathed IP since 2002, you know, but like as a founder, it's not something you think that hard about. So, this is like, you know, of course, when you look at a tur an investment term sheet, people are, you know, people on the VC side are telling you, okay, look at, you know, the liquidation preferences, look at the valuation, look at the amount, look at the board terms, all these things. IP might even be on page two.

Matt Gipple: 14:48

Yeah. Yeah. And like it, cruise is maybe so many companies. I imagine IP isn't like the thing. Um, it to some extent, what like what are you buying with IP with cruise? You know, we had some patents. Um at that point there weren't many, like they were more buying people in potential, but still, like that was it was important to us. I think in some companies, maybe your IP isn't the thing, but it's you know, you're in tech, it should matter. You have to pay attention to that stuff. And this it was atypical. Like you're getting a term sheet from a big, you know, 100-year-old company out of Michigan, where in all their other in a lot of their other negotiations, like their negotiation negotiation with a supplier, like they just kind of get what they want. So that this was different. We're like, hey, that's we get what we want over here. Like we don't need to be bought. Um, and that um position, I think, you know, was impactful to where we like.

Cecilia Ziniti: 15:44

Um, a lot of our um listeners work on MA and integrations, um, you know, without anything too confidential, you get acquired by crews. I gotta imagine, you know, you're 25 folks in a garage, you're, you know, the rules are like you're you're calling the DMV people, and you know, you kind of have this ambitious vision um to have truly autonomous vehicles that Kyle had been thinking about that since he was a child. Um what's your, you know, how were those? So you were there for four almost four years after that um at GM, right?

Matt Gipple: 16:21

Yeah. Um, all told just under five. So yeah, it happened really quick. And I I'm not a deal attorney, so like I don't know what a normal church sheet looks like at that point. So I was just reading the words and seeing what the words say. Like that's it, that that happens to be what you do as a lawyer a lot, is just read the words that other people don't want to read. Exactly.

Cecilia Ziniti: 16:40

So this is amazing. This is like, this is great. So our our themes on the show is like in-house leadership, and then um kind of being the best uh you know, lawyer you can be. And and I think that's right, um, is being able to do that. So that so you get to GM. What was the what what was it like? And then um any if there's um what are you most proud of in the kind of post-integration time period?

Matt Gipple: 17:04

Yeah, um the company's obviously very different, right? Like you have a bunch of like young people wearing flip-flops and shorts, and people from like old line big company in the Midwest. And GM, like the deal was as built out as it could be, but the premise was they're going to let Cruise be cruise and run itself and grow and and build a thing. Like if the like GM has had history, as many companies have, of buying things and accidentally killing them. Um, so they're trying very hard not to do that. And so the way it was set up was like we, you know, kept our leadership and essentially there were like ambassadors going in either direction. And these were like specially selected people who were supposed to not mess things up. So like I would go to Detroit pretty frequently and try to make them feel like everything was okay. I was an adult in the room, and you know, we have compliance, et cetera. Um, and then they would send folks who are like the cool kids at GM and they would come and say, Hey, you know, we're trying to help. So that like everyone was trying, it was still really hard. Like, there's just when you have a huge company that's public, like there are there are different things that matter, and there are things you have to care about that aren't the case at a 40-person company. Um, and what was especially unique for us is like this is high, high risk. Like you have cars, you have 3,000-pound cars driving around, um, driving themselves around.

Cecilia Ziniti: 18:34

And by the way, so I worked on privacy as well. And also they have they're basically have what is it, 32 onboard cameras. So they're constantly recording. And and there's there's tell us about the levels of regulation, right? So there's there's the city, there's the state, there's the federal, there's like three federal regulators. I don't know. Anyway, it's it's it's it it's literally like if you had to come up with a more challenging regulatory schema, like I think maybe healthcare, but other than that, I can't think of one.

Matt Gipple: 19:06

Yeah. Yeah. And like a lot of it what the kind of hack, so to speak, that we had was a lot of it was sort of in a, like, oh, doesn't apply. Like, um, I don't have a driver, so you don't have to license me. Um you know, and and you can take that too far. And so that's that's going back to that question of like what do we report for our first disengagement thing, is you're operating in a s in a space where they're on an ant there on answers, and so you work with like where your company is and how you're gonna be, what your culture is, and what you think is gonna work. Like you and and if your culture is report zero takeovers, you know you're gonna fight about it. And that's if that's what you're gonna do, so be it. Like that's the path you take. Um, so yeah.

Cecilia Ziniti: 19:51

It is that's actually been something super interesting just in the development, and we can we can talk a little bit about AI, is you know, so GC AI. We're legal AI for in-house counsel. And one of the things that very early on occurred to me is that you do actually modulate your advice to the client, right? And so like it's a different situation where, you know, you've got Elon Musk out there saying that he that he wants cowboys as his lawyers, fighting everything all the way to the chancery court, literally writing Delaware law. And then you've got others that are like, well, look, like, is there a benefit to reporting zero disengagements here? Is it a piece of marketing? No, it's a regulatory thing. We're going to be working with these regulators. Um, so really just like adjusting to the client. Um, so how did you you hadn't been in-house before? Was it just like a deep kind of like, like, how did you learn that? Was it just from this like deep trust with Kyle? Did you um, I think you and I have talked about you read Ben Heinemann's book, you've done other things like that. What, you know, the sort of learning on the job and becoming great at that? What how did you do it?

Matt Gipple: 20:58

Wasn't intentional. That, like the notion, I remember, so it was very like there was there's this group called Tech GC, which is a group of general counsels of tech companies, and it was brand new. And so when I first started, a big change is like you're the only lawyer. No one cares about the law. Like they all have things to do, and they're like, law is this thing that they don't understand. They're like, you know, what is the rule about water running through my neighbor's yard? And you're like, I have no idea, but they think you do. It's it's that experience. And, you know, there are these as a lawyer, like, I care about the legal issues, I find them interesting, and I'm used to being around a bunch of lawyers and talking about them. Now, like, that's you don't have a colleague, so to speak, in that, in that sense. Um, so TechGC was very useful just to like have a space where I could go and people would say, like, oh, here's, you know, here's you need to have an employee handbook. Like, oh, okay, yeah, handbook. That sounds good. So that was helpful. And then with regard to product counseling, it was kind of a new concept at the time. I I don't even know that it was called that.

Cecilia Ziniti: 22:07

Um Yeah, I think you're right. And kind of Google was calling them product counsel. I had that, I was one of the first at Amazon to have that title. But I think these like regulated industries where you're doing something new, that's where it gets it gets super interesting because you can affect the development, right? So like you're literally in there working on like dashboards and stuff back to the reporting example or simulations or like a pretty deep partnership on with the with the operators and the product folks, right, Matt?

Matt Gipple: 22:35

Yeah. I mean, it was fundamental for recruit. Like I think that's why you know many startups don't hire a lawyer to pretty far in. Like Kyle, you know, saw that pretty early and was like, okay, this is you're gonna need this. So yeah, we were hand in hand. Like another big piece was how the cars drive. So we need to know the rules of the road. And all of us pass our driver's license tests and all that. But the like we actually went through the whole uh the motor vehicle code in California and like mapped out all the rules and then worked with engineers to say, hey, what does this mean? Like a good one that I always think about is like when you're turning right and there's like an intermediate. So you're driving down the street and there's a Burger King entrance, but then you actually are turning right on the real street that's past the Burger King. When do you turn on your blinker? Because you're supposed to turn on your blinker 200 feet before, but there's a Burger King entrance. Like, how do I? So that's not clear in the motor vehicle code. Um, our answer is like turn the turn it on 200 feet before, even though you're gonna go past the entrance to the Burger King and go to the real street.

Cecilia Ziniti: 23:36

You've got people thinking that you're that your AV is stopping burgers when in fact it's turning right on out camino or whatever. Okay.

Matt Gipple: 23:42

We decide like the earlier is better.

Cecilia Ziniti: 23:44

Um it is fascinating. I mean, and and that actually was like really fun. Like the intellectual aspects of it. I mean, I just I I really did I I I miss it sometimes actually now that I now that I'm a founder, is I actually miss that. Um, and you know, it it is definitely a um for my lawyers, like what I look for in both my outside counsel and and in our in our team in-house, is like that ability to think hard about something so that I know someone's thinking hard about it. And then they can like make the recommendation and use their judgment to me. But yeah, I I w I wish I still I I miss it too. I'm like you.

Matt Gipple: 24:21

Yeah, I get that like the transition from being, you know, lawyer to founder. Yeah, I I very much miss the that piece of of the work. Although I'm still doing the legal work here, but um Oh, good stuff.

Cecilia Ziniti: 24:34

All right. Well, let's let's talk about it. So, so um, so tell us about your your so so when did you so you left cruise and and and and you decided to found a golf company. Okay, so like that's just wild. So tell us like what was going through your head. I'm assuming you took a little bit of a break. Um, and then and then tell us what happened.

Matt Gipple: 24:53

Yeah, uh no breaks, no breaks.

Cecilia Ziniti: 24:56

No breaks. That's not like Midwest.

Matt Gipple: 25:00

That's not true. I had a small break after cruise. I actually went in-house to a healthcare company called Forward um for a little bit. Kind of the idea was similar. It was like, all right, we're gonna change healthcare and all this stuff. Um very, very difficult to do. And I think was more on changing society first, which uh is also very difficult to do. I don't think you can do that intentionally. So anyway, was at Forward at the time, and my another friend of mine, uh Adil, um, he has started and sold a few companies. Uh, we went to college together. Um, and he he had recently sold his company and picked up golf. I can golf. Um can ask some people at Latham and they would tell you I can't. Uh I I once went out with the partners and like couldn't hit the ball, and it was it was like I have pretty good status at the firm, and then I had not good status. Um so anyway, I was not recruited for my golf abilities. Um but yeah, he he's a friend of mine. He's like, oh, we gotta start this, we gotta do this thing. He had he got to golf, the pandemic hit, you couldn't do anything, you couldn't even play golf, which in retrospect is like one of the few activities you should have been able to do. Um, but nobody knew at the time. So he was like, I need to feed this bug. What can I do? I'm gonna put a simulator in my house. Um, they live in San Francisco, they have children, and that was a non-starter um because it would have taken a kid's room. He lives like off of Geary, and on Geary, there's a bunch of trailers that park on the side of the road, like out west. He was like, why don't I just put this simulator in a trailer? The like the trick is that to swing a golf club, you need more, you need some a decent amount of width. The legal road width in the US is like eight and a half feet, and that's not enough to swing a golf club comfortably. So a deal figured out um and and patented, which is you know, keeps my legal hat on, um, uh a system to make a trailer bigger uh to play golf inside. So he made one for himself. He had it, it was a real thing.

Cecilia Ziniti: 27:03

You know, I literally, when you told me you were doing this, you know, golf in a box, I was kind of like, that's wild. But actually, knowledge of the roadways, it sounds like, and of California motor law is actually sounds kind of relevant.

Matt Gipple: 27:16

Yeah, yeah. Um, it it so he did this pre-me. So he figured that out on his own, like, hey, regular width isn't enough. How do I make this wider, but still be able to drive down the road legally? Um, so he figured that all out, built one, and he was like, you know, people keep like knocking on the door and asking me what this thing is, and I think we should make it a business. So that was um it took me a few, like I had to get for it in a good place where I could leave and not like leave them hanging. Um, but then joined to make it a real company. Um and that was the summer of 2021.

Cecilia Ziniti: 27:53

Wow. Love that. So how um so you went from law firm lawyer to clerk at the federal courts to startup GC to another startup GC, and now it went through to founder. Um what was the transition to founder like? And you know, obviously you handled the legal stuff, but what's how's that been?

Matt Gipple: 28:20

It has been hard. So like I prefer being a lawyer. Um it's it's easier in a sense. Like you have a much narrower scope, right? Um you only have to look to be a good GC, you need to care about the business side and whatnot. But like your role is to advise on on legal issues in the context of the business. As a founder, your role is to like make the best decision, period. Um and and so like it's pretty weird to leave legal issues sitting because you only have so much time, resources, whatever to deal with the things that are more priority. And as a lawyer, like, you know, that's driving, you know, that's that's pretty tough. So it's also I like doing the legal work more. Like, we the issues that Cruise have or that Dryvebox has, 98% of them are not legal. And, you know, I spent 98% of my time dealing with non-legal issues. I actually enjoy this 2% the most. It gives me the most intellectual satisfaction of what have you. But I don't get to do that because that's not the most important thing to the company.

Cecilia Ziniti: 29:25

Um it is interesting because I I I definitely, you know, I I had someone when I became a founder, someone, and you know, you I assume you share this view from from having uh us having worked together, said something to the effect of like, Cecilia, you were never really a lawyer. And I'm like, I lost them 20 years, like what the hell? You know, so much schooling. But I think constitutionally, I always felt the reverse about you, Matt. I really did feel you were a lawyer. And we would joke, and you said, okay, the people in the flip-flops and whatever. But I remember thinking, you know, I think you had, all right, I hope I don't embarrass you too much, but I feel like you had pleated pants, which at the time they were not in. Now I think they have come back in. So you were kind of like inadvertently before your time. But at the time, it was like, okay, he's wearing like his like federal clerk pants to like this startup. And we're like, well, he's just a lawyer's lawyer. And we would discuss, you know, among your team, because you grew a decent sized team. You had 30 people, 40 people, whatever, and we would talk about that. And it actually gave me comfort because I think you're right. You in that environment in Cruz, you needed a lawyer's lawyer. So you went from lawyer's lawyer to founder. Um, so how do you scratch the itch on the lawyer side? Do you read John Gresham on the weekend? Do you still read opinions? What do you do?

Matt Gipple: 30:40

I do actually, but I I will correct the record, they were not pleaded flat front, flat front. Um, but but uh yeah, I would wear like a button-down shirt and slacks uh at cruise every day. Um, probably like unconsciously for some like to give some legitimacy. Cause I was like, I don't know, 29 years old when I started there. And I had legitimacy with the people who worked there because they're 22 um for the most part, but more like more externally, I guess. Um and that, you know, I became a person that people could go to and know that I wasn't the same as everyone else who worked there. Um so that that was very intentional. Uh the one t-shirt I wore was cruise t-shirts, so I'd wear cruise t-shirts with slacks. Um but yes. Uh so anyway, like how do I scratch the itch now? I I still read legal news um and being an ex-antitrust lawyer, like this the it's ever present. Um, so we're seeing some good stuff now uh with some mergers that are proposed. And I I do read opinions uh on occasion, stuff that's interesting. Um trying to think of the last one I read. A lot of stuff that's coming out of the current administration is just like pretty, like pretty movements. Getting to see how courts are are attacking those things has been fun to watch. From uh at Dryve box, we've my legal work has gone up because I mentioned we have some patents, so we're actually into patent litigation. So that has been Wow, patent litigation.

Cecilia Ziniti: 32:12

Yeah, I will say patent litigation as a startup GC or as a founder or any kind of IP litigation, it is not good. Like I do not like it. As an IP litigator, like I loved the litigation part of it, but being on the client side, we had a trademark matter at one of my companies, and the entire exec team got deposed. It was, you know, I think it's you know, it's a public matter, but it was absolute garbage. Like it literally was like there was no likelihood of confusion. Like I feel very, very strongly about it. And it was a classic, like, and the person would say this, and this is in the public record, they, you know, that was, it was a lot of egos involved, and just, oh God, it was, it was like, I think I'm much more pragmatic now. So I guess like now that you're on the founder side, like what's your advice for GCs helping founders with IP litigation or any other kind of litigation?

Matt Gipple: 33:02

Yeah, like it is, it is much more than like you could I we wrote it down on paper. It was like this is gonna be really expensive, this is gonna suck up our time, and it's gonna be like mentally, it's gonna be toll, it's gonna be emotionally tolling. You can write that down, you still won't like grasp it fully. Um, and I think I could be accused of being like a litigation avoider. Um, despite the fact that you mentioned this, I love litigate. Like that is, I really enjoy that.

Cecilia Ziniti: 33:29

Like it's like we're a little kid and you're like, I'm gonna go to court, I'm gonna write briefs, and this is such a good argument, and I'm gonna write a tell a narrative and all these things. But the actual like underlying thing, it's like move on, do something else. Like it literally, like my my reaction half the time now is like, get a life. Like, you know.

Matt Gipple: 33:47

Yeah, like the business practicalities of it, you don't, it doesn't make sense. Um, it almost never makes sense. In our case, like this is the foundational thing for what our product is. So I'm a plaintiff, which again, like theoretically should be fun. And as as our lawyer, I would love it. The case, it's like a pretty interesting map.

Cecilia Ziniti: 34:05

Really it is. Yeah, yeah. Well, I wrote a I wrote a I wrote a cease and desist letter one time, and the the recipient apologized. And I was like, this is amazing. This is so fun. Please leave us alone, scary lawyer lady.

Matt Gipple: 34:17

We get a lot now where Chat GPT copies our website, someone makes a golf company, and they have like our same text. And we I write them a nice letter. I'm like, hey, you know, we're flattered because I wrote the copy. Um and that's what I get to do. Like as the as the ex-lawyer, as a founder, like I do all the words. So when we do words, Matt does the words. Um sometimes there's too many, and then a deal does a good job cutting them down, but I I usually start. Anyway, so yeah, like they say, Oh, like I had no idea. I just put it into Chat GPT, like give me a good thing about um like about a golf being inspiring, and it it uses the words from our website. Um, so we we say, hey, like you should come up with your own stuff. Thanks. And they do.

Cecilia Ziniti: 34:59

I love that. I love that. So you said something interesting. You said, I'm a lawyer, lawyers do the words. And I think that's actually super fascinating to link to AI. So you and I have talked about AI before, and you and you mentioned something very insightful, which is that a lot of the fears around autonomous vehicles um are similarly being applied to now, you know, LLMs and, you know, this like fear of jobs going away and truck drivers and what have you. Um, what's your your take on AI? So you are literally, or you lived in San Francisco, you're part of the kind of Y combinator folks, which of course, you know, Sam Altman came from there. You probably know Sam. What um what's Matt's take on on AI? And then we'll talk about AI and legal.

Matt Gipple: 35:43

My take on AI, like that's a very broad question. Uh I think it's wonderful. I think it is, it's so drastically changed like how people do things, myself included. It is, there's some study, I haven't read it, about how like people stop using their brains when they're using AI. Um and I I sh again, I haven't read it, so I can't say, but I think about that snapshot when I use AI, um, because I use it very frequently just to like answer questions. Um and I think people will use their brains in different ways. So now I'm thinking of more questions and because I can get answers more quickly. But before, like I would have had to research, you know, how like how some pumps will result in subterranean uh liquefication underneath my my basement. It's been running on should have been running some pump, and I'm like, huh, should I drain it a lot or a little? And I could have read you know five different things about that, and now I just kind of got the answer. But I can ask more things and learn more. So I'm I'm actually like learning more in less time. So I think that is pretty cool. And you know, the impacts to to society and business and what we do as humans, like they're unfathomable to me, but they're they're big.

Cecilia Ziniti: 37:04

I love it. I love it. Do you still um on the AI um uh theme when you see so now obviously Waymo has autonomous vehicles all around the city, they've come to Burlingame, my town. But do you still like get the chills or notice when there's no driver in the car? I don't, I don't, you don't, it's commonplace for you now.

Matt Gipple: 37:25

Yeah. I I think a lot of people experience this like getting in a self-driving car is such a big thing, like, oh my gosh, this is exciting. They got their cameras out, and you're in the car for two minutes and you're like, Well, works, it's kind of boring. I feel good. Like, so I think I my the sentiment that is that I still have occasionally is like, God, like cruise, you know, could have been us, uh, should have been there. But it is really cool to see that dream be a reality, whether it was us or someone else. Like we knew it was gonna happen, and it is happening, and it's awesome. So yeah.

Cecilia Ziniti: 38:03

I love that. Wow. All right, let's talk a little bit more about leadership. So hiring and team dynamics. So you have done, I still remember when I interviewed with you uh to take the role. It it was, I believe it might have been your first paternity leave, possibly, or maybe it was it was a holiday, something. And you told me at the time, you said, Hey, you know, there is no vacation from hiring. Hiring is the most important thing. I will take an interview, you know, anywhere, anytime. At the time, I'm not sure I quite fully understood that. I mean, obviously I was like, oh, this is just a guy that works hard, which of course you are. But now as a founder, it really is like it's been shocking to me. One of the most shocking things is how important hiring is and how hard it is. And so I guess on that note, what is your advice for hiring and um you know, any other kind of theories or hot takes you have on um on hiring and on on people to work with?

Matt Gipple: 38:59

I wish I had something. Like, I don't, I haven't figured it out. It's I've hired a lot of people. I have not figured out like the thing that that guarantees success. So, you know, my gut reaction is like whatever that phrase is, hire fast, fire fast, because you just need to like get to the right person. That's very hard to actually do in real life. I don't have the guts for it, so I I don't I I can say that, but I I I don't actually live it myself. But what I can't say is um on the flip side, it's very apparent pretty quickly who's really good and who's not good. And I mentioned like I don't have the guts to hire fast fire fast because you've heard this phrase before too. Like the moment you let someone go who you should have let go like a long time ago, you realize it. Um, that holds true for me too. Like when you think they're not the right person, you're right and don't delay it. So on hiring, do your best. I yeah, listen to podcasts with people who have better advice than than me on that one. That's what I would say.

Cecilia Ziniti: 40:05

Good stuff. All right. You've said before something that with two types of employees, those who do what they're told and those who do what they think should be done. Um why are both valuable? And I presume you've managed both. What are your tips?

Matt Gipple: 40:23

Yeah, yeah. So the there recognizing that these are like generalizations and whatnot, I think there's two types of people. So people who like they will do what they're told. You tell them to do a thing, they're gonna do it. And they can be, there's people who are really good at doing that thing and people who aren't. And so that's the spectrum there. And there's people who like are gonna go figure out what to do and they will do it. Um, they're both useful because there are times like you just need someone, you need people to do things that need to be done and need to be told. You know what the task is, you just need people to do it. And it's not even about like it's not a this person is better than that person. Like you need them both, they're both good. And if you have a person from category B and you tell them to do a thing, they're gonna do it differently than you need it done, and it's like unnecessary. So the the like they shouldn't cross. But then there are also a lot of times where you're actually not sure what needs to be done, or you're thinking about what needs to be done over here, and you need someone else thinking about what needs to be done over there. And so if you have a person from category A who's trying to fill in that space, they won't, they won't succeed at it. Like they will try. Um, or if they're a good employee, they'll try. And I've seen this a lot. Like they're trying, it's just not their nature. They they need guidance, they need someone to tell them what to do, and then they'll like knock it out of the par. Yeah, that's I think there's those two types of people. It's important to know what you need when you're hiring. A lot of times you act you think you need B, but you actually need A, and vice versa. Um early on in a startup, you often need more B. Um, but and then within those, there's there's good and bad. So yeah.

Cecilia Ziniti: 42:02

Yeah, no, it's interesting. I mean, it's definitely also like a what you need also is probably gonna change too, right? So for us, we've gone from you know, C to A to B very quickly, from zero to 1200 customers. And, you know, servicing 1200 customers is different than servicing 10 or whatever it is. And so yeah, it is definitely, and it is, I don't know, I I'm with you that it just has been like shocking to me how hard that part is, like the substance, you know, the law or the sales or the marketing or whatever it is, like that's words. We're good at that. But yeah, it's uh that's that's been a thing. So um, you do also, though, I remember this from from working on your team, have a really strong commitment to excellence and um, you know, a view that like excellence can come from anywhere, lawyers, non-lawyers, whoever it is. Um, any good stories with that? Anybody, anything either at cruise or since um surprise you that somebody maybe was not a lawyer or thought of an elegant solution or um or anything, any any stories to share?

Matt Gipple: 43:06

Let me think about that first. I will say, like, more often than not, non-lawyers come up with good solutions to legal problems. And not in the sense of I'm product counseling with you and we're working on an issue with your product. More like, hey, I'm a lawyer, I'm sitting down at the lunch table with you, and I'm gonna tell you about what I'm doing. And then they're like, oh, just do, why don't you just do this? I think often lawyers like we're trained, um, you know, think by by example, analogized to what has happened in the past. And the classic tech thing is like, oh, first principles and and all that, uh, all that. I I try to get too into first principles, but it is nice, maybe fresh take is another one. Again, this can this can get you in trouble when you're like, oh, just do a fresh take and forget about laws and come up with it the first time. But it is you get uh you get different perspectives when you talk to people who aren't in law, and that often helps you solve your problems. Specific examples or commitments to excellence, like uh actually, yeah, going back to takeovers. So this is this was more practical, but like when we first started, we had like a manual way of of um tracking our takeovers. And one of the engineers, like, because we had to, you know, going back to product counseling, this was fundamental to the thing. Like we had to build that into the process for how we were doing driving and training drivers. Um, one of the engineers was like, he he had he was relatively new, and this is one of those people who's like really good. And you can tell immediately because he's doing his normal job. And then he like at lunch heard me talking about this. It was like, this is insane, like use technology. So he built a thing that would drop a pin for like whenever there had been a takeover, and it would immediately take a note and take all the stats. And like that was the beginnings of us not doing this manually. And he did it in like an hour, like the next day. He's like, Hey man, I made this thing, come check it out. My my mind was blown. I was like, wow, you've just made one better.

Cecilia Ziniti: 45:07

That's awesome. Well, and I actually, for me, that's been one of the most fun things about AI is that as lawyers now we have the power to create systems like that. And, you know, literally like creating a playbook. So we're launching uh basically playbooks uh here where it's essentially checks that you can run against a contract. Because what do you do as in compliance? You run checks, right? You're looking at a piece of marketing, make sure that it doesn't do this, this, and this. And AI is objectively better at that than most humans. And so I've been just like the power of almost like creation of being able to be creative in that way that we have that now as lawyers. I love it. But that is an excellent story. Um, and it sounds like, and then you worked with this engineer for years later, then it sounds like too. Yeah, yeah.

Matt Gipple: 45:51

You know, I would try to grab him, like he very quickly got grabbed for more important big projects. But like every once in a while I would go and I'd talk to him, like, hey, you have any good ideas for this? Because there's two parts. One is AI, I agree, like it gives us the ability to build a thing. And that is a new thinking, like a new way of thinking for a lawyer is not just like, what is, you know, as a product counselor, you're supposed to like manifest your advice. Like you're working with engineers to build the thing to make it work. Now, actually, it's like, no, just go build your own thing to make it work. Um that turning that part of your brain on of like, okay, not only do I understand what the rule is and how I think it should apply in the product, like how do I build it? Um, so like that's kind of cool.

Cecilia Ziniti: 46:39

I love that. I absolutely love that. All right, let's go to a lightning round. So um is there anything about being a general counsel or um that that is a myth that that you would you would want to debunk?

Matt Gipple: 46:54

Uh gosh, I'm thinking through a lot of different things. I think this is this is a bit of a contrarian take, but like the there's this big push in legal to say like, hey, we're part of the business, we are like we're as much in the business as you are. I think that has that that can be taken too far. And you don't see it happening in practice, you just see it see it in words. It's like lawyers want to pitch themselves. It's like, no, I'm a business person too. Um like you, you aren't. You're there not to be. You still need to help the business, but like you aren't. Um, so the like I I was not a business person at Cruz.

Cecilia Ziniti: 47:37

Um well you you had the the flat front pants, right? I'm just kidding.

Matt Gipple: 47:42

Yeah.

Cecilia Ziniti: 47:42

No, I actually I actually think that it's true. And you know what for me, you know, I I I think that's good advice, actually, because for me, I deciding to become a founder, part of it was, you know, and and I worked for you and I had a great time working for you. Um, incredibly impactful year of my career, fascinating issues, one of the best lawyer jobs I've I've ever had, easily. But ultimately I left to be a GC partly because as a GC, I think you get more of that permission to be the business person. And ultimately for me, also, you know, the decision in my career to become a founder was that the lawyer side for me, like I hadn't, like it wasn't deep enough. And playing that role for me wasn't the right one. So, like, but now, just like that conversation that, you know, that I mentioned, that like I want my lawyers to be thinking deeply about the law, particularly where it's a big thing, you know, in a funding round, when we have a term sheet, all these situations where I want to be protected. So I think that's a great contrarian take. That being said, you know, of course, here at GC AI, really big, move the business forward, business accelerators, yeah, do the creation. But I think if you can actually do both, like that that advice to manifest your product counsel is manifest your advice, like, oh my gosh, that's like that's gonna be that's gonna be the clip of this show. So good, good advice. I love that, Matt. Um, awesome. What about a book, idea, or mentor that's shaped you?

Matt Gipple: 49:05

Yeah, I have a couple mentors. Mentor is a is a broad term. One is my judge. I like sucked at writing. I was terrible at writing. Um, yeah, I I just haven't ever really been trained.

Cecilia Ziniti: 49:18

I am making like I got my eyebrows raised because Matt is an excellent writer.

Matt Gipple: 49:22

So I came out of law school not really ever having been trained well. Like I took legal research and writing one other year. Uh worst grade I got in law school. And like I chopped that up to like being busy or whatever. But no, it turns out I just wasn't very good at writing. And as a first, second year associate, like, you don't do a lot of writing, at least at the time you did it. And I had gotten some opportunities to do some, and like a partner like kindly brought me in. He was like, Matt, this is really bad. Like, this is not good. You can't, he's like, what you're trying to convey, you know, you want to convince someone of this argument. I'm reading this and I don't even understand what's happening. It was like, you know, that was a that was a tough day. Um, so I I chopped that up. The person's name was Matt, and he just like got real with me and said, Hey, like, this isn't good. You gotta, you gotta, and then it just so happened that like that was pretty close to right before I went to clerk. And then I went to clerk and just got smoked. Like my judge just every day was working on me, like, Matt, this is how you convey things clear clearly. Like, stop using so many words, just help people understand. So those two people, my judge, and then the like kick in the pants I got from that one partner, um, really impacted my abilities and like my mind of just like thinking, oh, I'm some smart person. Like, no, the the the craft of of being a lawyer, at least in that context, is writing, and you weren't doing a very good job of it. You're not conveying ideas well. People are not understanding what you're saying. So I love that.

Cecilia Ziniti: 50:53

Wow, this has been so much fun. Matt, um, thank you so much for coming on the show. Where can people um follow what you're building or try out Dryvebox?

Matt Gipple: 51:02

Yeah, um, Dryvebox is all over. So we're actually in the UK as well. So we we launched in the UK this summer. Uh we're in there's 50 of them now. So most major cities in all yeah.

Cecilia Ziniti: 51:14

I remember when you had one. That's incredible. Congratulations. Wow. Um it's super fun. It's literally like like a trailer. You go in and play golf, they do parties. It's kind of like, you know, there's these like here, they have those those trailers where you can play Xbox, but this is this is golf. So fun. Can't wait. Next GC AI off site, done.

Matt Gipple: 51:33

Yeah, have us out. Um, yeah, so we do events all over the place. There's 50 of them, so pretty much anywhere in the in the US, continental US. There's one going to Hawaii soon. Um, so we're everywhere. Uh, dryvebox.com and we'll show up.

Cecilia Ziniti: 51:47

Awesome. Thanks so much for joining me, Matt.

Matt Gipple: 51:50

Yeah. All right. Thank you.

Cecilia Ziniti: 51:52

That was my conversation with Matt Gipple, a former general counsel turned founder who shows what it'd like to move from advising to building with judgment and clarity, incredible stories. He talked about manifesting. I am just uh so excited to have done this episode. Follow CZ and Friends wherever you get your podcasts. To learn how legal teams are using AI to work smarter and lead with impact and lean into the lawyer side. Visit gc.ai. Thanks for listening. We'll see you next time.