Vibecoding Legal Work

Welcome to Reinventing Professionals, a podcast hosted by industry analyst Ari Kaplan, which shares ideas, guidance, and perspectives from market leaders shaping the next generation of legal and professional services. This is Ari Kaplan and I'm speaking today with Matt Pollins, the co-founder and chief product Officer at Loophole, a work management platform for attorneys and agent teams. He is also the co-founder of Vibe Code Law, an open community platform launched in 2026 for legal professionals to learn how to build apps and share what they've made.

Hi Matt. How are you? Hey, Ari, it's good to be here. Thanks for having me.

Oh, it's my privilege. I'm looking forward to the conversation. Tell us about your background and the genesis of Loople. I am an attorney by background.

I spent about half my career in London and the other half out in Singapore. I went from being a tech lawyer. Working with companies like Microsoft and Meta and the big tech companies as well as startups to legal tech. So pivoted really from practicing to co-founding loophole.

Around 2019 two, 2002, made that leap really from tech law to legal tech. How does the loop platform work? Loophole is a work management system, and the problem that we solve is that what we see in law firms is there's this big gap between, systems for the billing and the time and systems for the documents. The work product that rolls off the production line.

But in the middle there's this whole space, which is who's doing what and what needs to happen next on my case or my transaction, or my project. And right now, a lot of that is managed in Excel trackers and word tables and email threads. Whilst every other industry has adopted work management tooling, like you can't run an engineering team without a JIRA or one of those tools or an IT team without ServiceNow. Or a marketing function without monday.

com or Asana. In legal, we have our word tables and our Excel trackers, and that's crazy. So what we do is we take work out of those clunky manual trackers. We put it into a real time collaborative system, wherever everyone can see what's going on what needs to happen next.

And then increasingly, we started with the. Hey, how can we get people to organize their work to help attorneys organize their work? And now that we've organized it, how can we automate it? And we do that with both deterministic automation.

So that's the whole, if that then this workflows. But we also do it increasingly with AI and. The reference you just made there to attorney plus agent Teams is a new feature, really a new product that we've rolled out at the start of this year, which is, we think AI is gonna go from being what it is now mostly, a chat bot. You look at how it's being used in most law firms, it's a reactive chat bot.

Already in engineering and other industries, it's becoming a proactive teammate. So how do we apply everything we've learned about. Attorney to attorney collaboration and project management for the last five, six years to a new paradigm where, yes, it's attorneys, working with attorneys, but it's also attorneys working with agents alongside them as well. That's the bet that we've made here really in the start of 2026, that is gonna be the new way of working.

How much human input and how much automation is necessary for a team to optimize the loophole platform. We are very much believers in human, in the loop, attorney in the loop, we do not think, and, for insurance reasons, for liability reasons, for all the reasons which we both know, we don't see a world right now where it's just agents. But let's take the example of like contract review. There's a growing number of AI law firms launching.

And what these law firms tend to do is they'll intake a client request. You need a bunch of contracts reviewed. You send it out to the law firm. AI does the first pass.

It triages it, and it says, okay, , eight of the 10 are aligned with your playbook, but two of them look high risk. So we're gonna assign those to a more senior lawyer. The senior lawyer reviews it and they get back to you within. In some cases, these guys are doing like a one hour SLA or a three hour SLA so that's what the new entrants are doing.

We are effectively doing that with big law. We're helping big law to adopt those kinds of processes. You have a first pass review by an AI agent who takes an email or a teams message triages. It does the first pass.

And then assigns it to the human reviewer. I could do others data, subject access requests litigation filings and things like that. But it's all about, how can AI not just sit there and wait for you to ask it to do a thing? How can it do a thing even whilst you're in all day meetings?

It's done the first pass, it's moved things along, and it's and then we can take the next step in whatever the legal process is. How did you evolve loophole's initial mission to adapt to the current needs of legal professionals? We launched in the middle of the pandemic and no one was really using collaboration tools in 2018 2019. Do you remember the days of the.

You get on a conference call and there's the ping when Ari has joined the meeting. And then sometimes somebody doesn't announced they've joined the meeting and you don't know they're there and all of that fun stuff. It's like a lifetime ago. And that's actually when we launched Loop was really a lifetime ago, feels like before the pandemic.

And we evolved the product from its initial focus, which was just general collaboration and communication, which very quickly got swallowed up into the world of teams and Slack and Zoom and it wasn't differentiated enough. So we effectively pivoted as a company to focus on work management, legal project management, and workflow automation, because that was the part of the product that people were really engaging with and they were less interested in just general communication type tooling.

So that's how we evolved and really more of a pivot. What's interesting, I think is just in the last few months. We've noticed the Harvey's and the lags starting to do some of what we were doing five years ago with shared spaces and collaboration portals and things like that. Less so on the work management side.

But, I guess everything changes and everything stays the same in some ways. When I used to join those calls and I remember those days where it'd be like. Matt is joining the call. Bob is joining the call and because you had to record your name, I'd say something like Ari Kaplan then all these people would be, Susan has joined the call.

Ari like it. People just start laughing. And I thought, come on guys, this is super boring. Let's let's ramp it up a little bit.

And there was always one guy who didn't announce himself properly, and you'd get half, you're 30 minutes into the call and you're talking about Dave as if he's not there. And suddenly he chimes in with he said, and be like, Dave, I didn't know you were in the room. You, you've been here this whole time. Good times.

Why did you launch Vibe Code Law? Vibe code.law. , So I have a bad habit of buying domain names.

My wife criticizes me for this and right, rightly but it literally started with me. I've been vibe coding for a couple of years. Like I love building stuff. I do it in my day job.

But I also do it for this fun weekend projects and. I saw the Vibe Code, law Domain was available, bought it, didn't have a immediate plan for it. And then got together with a few friends and we spent a couple of weekends building some stuff. And the reason for doing it really is we felt like the conversation on Vibe coding is polarized between, on the one hand, you've got people who say, I could vibe Code Harvey in a weekend.

And there are the others who are saying it's a waste of time. You can't build anything. You're not serious if you're vibe, coding stuff. And neither of those two things are true, in my opinion.

I think the right answer is somewhere in the middle. So we trying to bring a bit of sense and clarity to the conversation. It's also just great fun. And we've just launched a thing called Vibe Academy, which is a place where legal.

Professionals can learn to build. It's all totally free. It's not a commercial thing. It's genuinely like a hobby project, which we're running on the weekends.

But the reaction has been great. And we've got, I think coming up for 40 projects on there from around the world. And I've gotta say the coolest one was from launching. Within a week we had the Harvey of Mongolia had submitted to the platform.

I just love that it went from idea to release to someone in Ulu. Batar is sending in an app in the space of a week. It's just the power of LinkedIn and the internet, what is the underlying technology for them to vibe, code through your site? They don't actually vibe code directly through the site.

We effectively provide a place for 'em to share what they've built and to learn how to build stuff. We recommend a few different tools. So for someone who's just getting started with Vibe coding, we usually recommend Google AI Studio. Because it's free up to a pretty generous limit and you can genuinely vibe code an app in 30 seconds to a minute.

It's got that wow factor that immediate dopamine hit. I did this with a group of law students a couple of weeks back on a. Presentation and we vibe coded an app. The TikTok of English case law was the idea.

We made it in 30 seconds or a minute. And that was AI Studio. There are a bunch of others, repli lovable, they're quite good for prototypes. Claude Code is the king right now.

They built Claude Cowork with Claude Code. I don't know if you would call that vibe coding. The founder says he doesn't write code manually anymore, hasn't done since December. So I feel like the term itself is broadening to encompass virtually all coding is vibe coding safe for legal work.

We recommend what we call responsible vibe coding for lawyers. We always recommend don't upload confidential or privileged data into something you've just built. It's easy to, get ahead of yourself a little bit. And we're all guilty of this.

You type in a prompt, an app appears and you're like, wow I'm amazing. I know how to build stuff. But there's such a huge gap between something that you build in a couple of minutes that looks great, and production grade, enterprise grade software, and particularly in our industry, there's just too much risk. And in the same way as we wouldn't recommend a client.

Vibe, draft a share purchase agreement on a big m and a transaction. Probably not a good idea to vibe code, something that's gonna process confidential data. Reach out to a proper experienced engineer who can help you take what you've built and take it to the next level. Something that's production.

Prior to launching Loophole, you were a partner at a large law firm. How does that experience inform the work that you do at Loophole? I was a tech lawyer back in the day. I definitely apply a lot of what I learned from working in the tech sector.

I probably had an advantage over other lawyers who hadn't necessarily worked with startups, but still there's such a difference between advising a startup and actually being in a startup. And that's been quite the learning. Process, quite the rollercoaster ride. It's not for the faint of heart founding a startup, I will say that.

But we've had some great times and I love it. But how does it inform it? I think there's partly also some stuff I've had to unlearn. As an attorney, you are so focused on finding problems.

The racing track analogy is, we're focused on the barriers around the edge of the track. We're not focused on the road. Sometimes. That's probably a bit of an unfair generalization.

And as a startup founder, you've gotta see opportunities everywhere. You can't just focus on the risks. And you've gotta balance those things a little bit more. But I'd recommend it to anyone, any attorney listening.

It's not for the faint of heart, but it's an incredible journey and the barriers to entry to founder company these days are lower than ever as well. Why do you think so many lawyers seem to be starting legal technology ventures? It is a couple of things. Obviously we are very close to the problem space and there's still plenty of problem space out there that's unsolved, despite all the press releases and the funding rounds and everything.

The fact that there are may be more legal tech companies than law firms these days there are still plenty of problems to solve and lawyers experience those every single day. When they see them unsolved, they want to do something about it. There's a sense perhaps of fomo. You see a junior associate from a west coast law firm found an $11 billion legal tech company and you think, gosh, maybe I should do something there as well.

So there's a bit of that. And then, to the discussion just now on vibe coding, we are at a time where a partner or a founder can vibe, code a prototype. Again, not a production app, but a prototype. Get it in the hands of potential users say, would you use this?

Maybe get it in the hands of investors and get some seed funding and start to build something. The days of look, it's gonna cost you 250 K to get a prototype behind us. You can move so much faster now and I guess that's gonna be appealing for a lot of attorneys. Turn founders.

How do you see the practice of law evolving? The revolution's not gonna be evenly distributed. Maybe I'll answer it for big law. We will see a growing productization of legal work.

It's already starting to happen, but we're gonna end up with what I call a multi-channel law firm where. Some categories of work that used to be done in a very artisan manual way. Hourly rates, it's just not gonna happen anymore. Either the clients are not going to outsource it, or if they do, they're going to want fixed fee.

Fixed SLA turnaround time and outcomes. They're not gonna be paying for inputs. They want to know. What the outcome of that is going to be.

So a bunch of work will flow down that productized channel. Which is scary for some law firms because, do you cannibalize your own practice groups and target that productized work? 'cause you know where it's going. The whole iPhone cannibalize the.

iPod. It does seem to be where it's going. That's the product size channel. But then there will always be room for the bet the company stuff.

So the run the company stuff goes down the product size channel, the bet the company stuff probably isn't gonna change that much, and probably the hourly rates for that are gonna go up even higher. This is Ari Kaplan speaking with Matt Pollins, the co-founder and chief product Officer at Loophole, a work management platform for attorneys and agent teams. He's also the co-founder of Vibe Code Law, an open community platform launch this year for legal professionals to learn how to build apps and share what they've made.

Matt, thank you so very much. Thanks again. Thank you for listening to the Reinventing Professionals Podcast. Visit reinventing professionals.

com or ari kaplan advisors.com to learn more.