“My journey starts really back when I started my first startup journey with my co-founder, Alex. We're really good friends from back in North Carolina in our undergrad days at NC State… We were in electrical engineering together, and that's how we met each other.

We always had a passion about starting something throughout college, and had the opportunity to start a business together, which was not in the tech space at all, which was in the alcohol catering business. So we actually started a mobile bar company called Bar Box down in Raleigh, North Carolina.

Raleigh, at the time, was going through a bit of a transformation. A lot of the downtown area was being developed, and there was a lot of unused space, a lot of unused land, and so we thought – what better way than to create a physical concept where people could enjoy the outdoors? We were originally thinking about a bar and dog park concept called Bark.

So we were thinking about ways that we could activate some of these unused lots, and so our idea was to buy a mobile horse trailer, flip it into a bar coffee unit, and run these concepts. Fast-forward a couple months, we weren't able to kinda get the permitting process to where we wanted, but we did figure out how to build a horse trailer out, and we decided to build an alcohol catering business, and so we ran that while we were working full time.

Alex was at Fidelity, I was at Capital One, and that was our first foray into working together on a business. And, uh, we started that in 2018 and ended up selling it in 2022.“

“You know, it really got to the point where we needed a second horse trailer, to expand the business, and so we felt like our talents were probably better spent building a tech startup. But, we got really deep into contracting as a small business, and then having that experience of actually selling a business ourselves to another operator, that was all kind of our first foray into legal.

We really enjoyed the process of our legal transaction and our workflow, and where we really sank our teeth actually was later at another job called Pacaso Homes. And so we got an opportunity to work together at a startup that was in the fractional co-ownership of real estate called Pacaso, where a lot of our product was our transaction process. And so Alex and I got to work with our sales team and our legal team there, where we were really thinking about some of our legal transaction workflows and got familiar with some of the tooling in the space and was really inspired to start a company to help out lawyers at the time.”

“That's right, that's right. When we joined we had a mutual friend that was working at the company, and there was this opportunity where they needed a product manager and a backend engineer, and so, you know, it was kind of a good fit.

I remember three months in, we were having dinner at an offsite with the CEO, and he was, ‘How did this happen?’ Like: ‘How did you guys work together?’

That was a really cool opportunity to be able to kind of get into trouble, both at Bar Box and at Pacaso together, working together on the same problems.”

“So at the time, Pacaso was going through a lot of changes, and so they had gone through, three rounds of layoffs, and it was really at the end where we were like, closing up shop as a product team.

So Alex and I both, I would say, fortunately, got laid off to be able to start this opportunity together. It was at the time where Alex was living in New York, I was in San Francisco, and we were thinking about whether or not we wanted to join another company or start something ourselves.

And that's when GPT-3 came out. I remember I had gone to a LangChain meetup at the time and it was only about 30 people. I met a lot of interesting people, specifically the CTO of Zapier, who told us, ‘Hey, like, I'm actually gonna step down from being CTO for a bit and making my head of engineering CTO, and I'm gonna go off and explore this whole AI thing.’ I met a couple other YC founders while I was there, and they all encouraged me to apply.

And so Alex and I were tinkering on a couple different ideas and landed on, ‘Hey, I think we should really stick to legal.’ It's something that felt like a particular pain that we were both familiar with at Pacaso and probably something that we would enjoy doing and building as a company together, and so that's when we applied to YC in March of that year.”

“The beginnings were kind of a scrappy prototype. At the time, the magic was being able to chat with a PDF, right? So the first versions of ChatGPT, you couldn't have external file upload, right? And so we built a chat-with-PDF app, and we made it a little bit more legal focused. So we had some metrics that you could pull specifically about contracts, and really we're thinking about contract review and thinking about like a Google Docs editor for legal, and that's what we got into YC with.

The original intention of the app was to build for other startups. So, you know, startups are negotiating. They typically don't have budget or time to be able to work with outside counsel. And so our intention was to get into YC and try to kind of validate our idea with early-stage companies.

[Our first few customers were] in our batch. We were meeting other folks that were like, ‘Hey, we're signing this deal,’ or, ‘We're meeting this enterprise,’ and trying to test the product with them. It was mostly early-stage companies where founders were leading negotiations themselves. It was through the batch that we learned a couple things:

Early-stage companies don't really have the volume necessary for a scaled B2B motion.

Early-stage founders don't actually negotiate all that much. They kind of accept what they can get.

We take what we can get, and so that's when our focus towards the end of the batch really focused towards B2B enterprise SaaS companies, focusing on in-house legal counsel, where they had a perspective. They were really informed about the product, and the outcomes they wanted to drive, and really building for them.”

“One thing that YC says during the batch, and we can all learn from, is: launch early.

Always get your ideas out there because as much thought we have around putting something into the world, oftentimes, it's a little drop and a little ripple, right? And so getting that muscle of just pushing things out there and getting feedback is one.

Another one was, at the time, who we were getting feedback from. So at the time, we were working on this web-based editor for building out contract review, and it was pretty complicated. At some point, we decided that what we were taking on was quite ambitious, and we actually ended up pivoting the idea a bit, which I'll get to in a bit. But, I think focusing on distribution, focusing on talking to more customers, and maybe building something that was smaller and more simple, instead of so ambitious from the get-go, [that] would've been something that we would've probably taken a second pass at if we did it again.”

“What we learned the hard way was that the minimal bar for our buyers, which are innately a risk mitigation role and they're very allergic to change as a result.

So anything one degree outside of what they're normally used to is something that we have to take on as a huge change management challenge. And so, for example, today, we have contract review, but it's built directly within Microsoft Word.

We also have contract review, but it's an email agent, right? So we're introducing one degree outside of what they're normally used to as part of their workflow, and that has been resonating really, really well, as opposed to, ‘Hey, we're gonna introduce a radically new different workflow to, to what you're used to.’ A lot of these in-house professionals are dealing with innovation day in, day out. They have an appetite for the things that are new. But when you ask them the same question of: Would you use this? I think it's a quite a different answer. So, we had to be a lot more selective about the kind of feedback that we were seeking, rather than, folks that are generally pretty positive about anything that they wanna support, as opposed to what they're paying for.”

“One of the things that we were kind of deciding... we kind of pivoted to being more of a post-signature management platform. So the idea being a lot of businesses don't necessarily know what they've signed. You know, they have contracts that are sitting in DocuSign or Google Drive.

Being able to become a system of record seemed to be an obvious place that a lot of the market wasn't focusing on and was an obvious opportunity because a lot of the incumbent software CLMs in the space weren't very good at it. And so we said, ‘Well, why don't we go to a place where nobody's focusing on?’ And we quickly learned that there was just so much to build, to get right, to be able to even hit minimal viable product, right?

It was crazy because we would ship something that we thought was good enough, go back to customers, and we're like: ‘All right, will you be willing to pay for it?’ And they would be like, ‘No, but we need X,’ or ‘No, but we need Y.’

And there was this period of just utter delusion that we had to go through that at some point, there was gonna be a light at the end of the tunnel. And you know, there's just so many darts that we're throwing at the dartboard that felt right but just weren't sticking.

And you know, we were thinking about burn. We were also then being like, ‘All right, well, we just need to survive to the point that we're actually making some revenue.’ So we were trying to limit risk, so not making as aggressive investments and maybe hiring.

That changed our perspective. Obviously hindsight's 20/20. You wanna step on the gas now, now knowing what we know now, but it was a pretty scary time in terms of: is this even the right thing that we should be working on? 

Is the information that we're getting from prospective customers even the right things? It was really hard to get good advice. We were kind of at the edge of knowledge in terms of there was not a lot of precedent for what we were doing.”

“It was really helpful because Alex and I were so inspired by Linear in particular. We talk about this a lot because Linear, to us, represents a software company that is just a team of craftsmen, right? They value the artistry of building software and having strong opinion.

As somebody who's been a PM and using Jira for years, I dreaded using Jira. Linear was such a breath of fresh air, and for us, [we thought] there has to be something true of this for lawyers, right, of being able to build the right opinions within the software and move very quickly.

If that assumption was true, that somebody had to do it, and we didn't really see those examples, we were like, ‘Maybe it's us.’ It was kind of blind faith that we could keep building the best thing, and the terminology and the style and the vibe would be picked up by specific customers, and eventually it would work out. And so it is cool now seeing our first 20 customers, using the language that we use and thinking about primitives and software and the way that we think about because they're the ones that are kind of evangelizing this for other folks.”

“You know, I can't complain. I'm getting to build a company with my best friend.

Alex was my best man at my wedding, right? And we've gone through so much of it together, and while it was very difficult, knowing that there's this ultimate support system in your co-founder and being able to just try new things and just get better has always been a motivation for us to even start a company.

I think a lot of people come into this space thinking that they're gonna make a ton of money, or they're gonna get a lot of fame, and while that's obviously a motivation, in some degree, getting the opportunity to just build something cool and do that on your own principles has always been, um, the biggest privilege. We really cherish that and value that every day.”

“Yeah, absolutely. As I mentioned, our core offering is a repository, right? A post-signature management platform, and what we've realized is that a lot of lawyers are precedent-based, right? The first question that they're gonna ask when they see a contract is: What have we done before?

They don't want to invent anything new, and so what we've done is we've recognized that our platform maps that precedent. And so what we can do is then use that information, kind of like mapping the DNA of the choices that they've made, to influence some of the pre-signature workflows.

So we've built two products in the past couple months. One that's an email negotiation agent. It's pretty cool. You can send a contract to an email. If Michael Wang were to send that to us, we would actually review that agreement, negotiate it on your behalf, and send back the red line version, all authored in your name. It's kind of a magic product, within email.

The second product is an actual Word add-in. So this is a plugin that you download from the Microsoft AppSource and it's a copilot that pops out. It'll review a contract, generate red lines, you can apply it to the agreement, and use it as almost a Cursor for legal docs, right?

We would call that as an extension of our repository, like being able to bring that precedent right into the transaction. One offering that we've been doing for a lot of early-stage companies is actual contract review. So we have a number of YC companies that we're supporting today, but, you know, teams that don't have in-house counsel, maybe they're negotiating MSAs and order forms. We set up a Slack channel, they work with us, and we're able to offer a flat-based bill for unlimited contract reviews directly within Slack.

It's available to any startup, and the way that we make that profitable for us, is that we actually use our software under the hood. So you actually have an attorney who's directly within Slack, and they're working with you. They'll turn around contract reviews in your name for you to review. We're not a law firm, so I just do wanna make that clear. We're not a law firm by any accord.

We're able to take your precedent, we're able to take your templates, we're able to take deals that you've done in the past, and we're able to use that as a way to help accelerate some of the choices that you would already make. Then put that first draft for you to review and accelerate. So, we have teams where originally it's the CEO or the founder owning all the redlining, and now their sales team is just interacting with Docsum directly in Slack to get all their deals done.”

“One thing I would say is I make sure that my passions are something that I can definitely experience every day, if not every couple days. So one of those is cooking.

As founders, we're working on long-term goals. A lot of the things that we want to achieve don't happen in the same day. 

So for me, being able to cook a meal, where I buy ingredients, cook, clean up, eat… it's one of the few things that I can see from start to finish in the same day. 

Having that sense of completion is one of the most rewarding things, because oftentimes we don't feel that sense of completion day to day. 

[Favorite food to cook] I cook a lot of Indian food. I actually started an Indian spice company with my mother, called Mama T's. It's a little passion project with her. 

I love making a dish called rajma. It's a North Indian red bean dish, super hearty. It tastes like Indian chili, but it's super good, and I usually will make a pot of that and have it in the fridge. 

I also play basketball every Wednesdays with the same group of guys, you know, we play every week, and so that's a nice ritual.

Another thing is, I try to wake up as early as possible, and I'm usually the first one here in the office, but I try to take my mornings a bit slow. You know, drink a cup of coffee. I always keep a notepad with me, where I'm actually writing. So I will write down my goals and my to-dos. 

I've always woken up and physically write down what I need to do, even if it's repeating day after day and I don't get it done. Because what I find is that if I physically write it down, my relationship with that work and how I remember it is quite a bit different than just typing it out.

[It] makes it more approachable. It makes it feel like I do remember it. As a founder, you're just stretched thin amongst a bunch of different priorities. And I've tried a ton of to-do lists and to-do apps, and to be honest, a notebook and pen and paper is honestly the best thing, at least for my workflow.”

“Couple reasons. One is, I'm an East Coast kid. I grew up on the East Coast. I actually grew up in New York City when I was younger, I grew up here in Flushing till I was eight, and then moved to North Carolina. My wife's family is also on the East Coast, in North Carolina as well, and then my co-founder, Alex, his entire family is in the New York/Pennsylvania area.

From a timing perspective, it just made sense. If we had the opportunity to just be proximally close to family, that's a big thing that we wanted to prioritize. 

Number two, I love the feeling of being small in New York City. We have this little world of legal tech and working so hard and all of these things, but as soon as I step outside of the office and I'm walking home, there's a million other people that are kind of all thinking about other things.

It's very humbling to be in New York and seeing people experience success that's outside of the world of tech. Whether it's dance or food or other avenues for success, I think is really humbling, and it's just a joy to be around other people that just wanna be the best. 

I think New York is amazing. And I think one thing that was tough for me in SF was as beautiful as the place it is, it was hard for me to continue to stay in a place that relatively had a homogenous culture, you know? And being in New York City is something that just brings me a lot of energy, and I think that is something that makes me a better founder.”

“Yeah. If you are a founder, and you need some help with contracts, we're happy to help out, whether it's contract review or anything from that aspect.

I would say we're looking to also figure out ways to connect with more in-house attorneys. So if you know folks, [we] would love to amplify our message that way. And then, if you're in New York and you're looking to just meet up and collaborate and be friends, we are working with a lot of AI and document processing and we like to get pretty nerdy on some of the technical aspects and technical stacks. So, other really good builders are folks that we wanna connect with and spend more time with.”

If this sounds like you or someone you know, reach out at [email protected] or via LinkedIn.

Shaunak Turaga is the Co-founder and CEO of Docsum, an AI-powered contract repository and negotiation system used by legal and revenue teams to accelerate deal cycles and gain clarity on their commercial relationships. Docsum combines AI-assisted redlining, contract analysis, and post-signature reporting to give companies visibility into risks, pricing, renewals, and obligations. Shaunak founded Docsum in 2023 and has been an active member of NYC Founders Club since 2024.