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NYC Founders Club
Jan 28, 2026
How Utter Delusion Helped Build Docsum ft. Shaunak Turaga (Docsum)
How Utter Delusion Helped Build Docsum ft. Shaunak Turaga (Docsum)
00:00
21:27
Transcript
0:00
That's blue. [laughs] Appreciate it. Well, Shounak, hey, thank you so much for taking the time, man.
0:06
Uh, it's so funny because I know we've talked about the, the, you and DocSum a little bit, um, just one-off, but I don't think we've ever talked about the full story, so I'm excited to, to kind of get to it. Absolutely.
0:17
Thanks for having me. Well, Shounak, why don't we start from the beginning? Tell me all about you and DocSum and how this all started. Well, you know, I think my journey starts, um, you know, really back when
0:30
I started my first startup journey with my co-founder, Alex. We're really good friends from back i- in North Carolina in undergrad days at NC State, and we actually started our first- Were you roommates? We weren't, no.
0:42
We were, we just- Okay... met on campus. We were in electrical engineering together, and that's how we met each other. Got it. Yeah.
0:48
Um, and we always had, you know, a passion about, you know, starting something, you know, 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.
1:00
So we actually- Wow... started a mobile bar company called Bar Box, um, down in Raleigh, North Carolina, where we took a horse trailer- Whose idea was that?
1:08
And how many drinks had you had when you guys came up with this idea? I would like to say the number was a lot lower than it actually was, but- [laughs]... let's just say that Alex and I like to entertain.
1:20
Uh- Beautiful... and, um, yeah, we, we originally, you know, in Raleigh at the time, it was going through a bit of a transformation.
1:28
A lot of the downtown area was being developed, and there was a lot of unused space, um, a lot of unused land.
1:35
And so we thought what a, what better way than to create a physical concept where people could enjoy, um, the outdoors, and we were originally thinking about a bar and dog park concept called Bark. So- Ooh, great name...
1:49
we were, we were, uh, thinking about, you know, 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.
2:02
And so, um, you know, fast-forward a couple months, we weren't able to kind of get the permitting process, uh, 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.
2:16
And so we ran that while we were working full time. Alex was at- Yeah... Fidelity, I was at Capital One, and that was our first foray into working together really on a, on a, on a business.
2:25
And, uh, we started that in 2018 and ended up selling it in 2022. That's incredible. Why'd you sell it? You know, it really got to the point where we needed a second horse trailer, uh- Sure...
2:37
to expand the business, and so we felt like, uh, you know, our talents were probably better spent building a, a tech startup.
2:43
But, um, we got really deep into, you know, contracting as a small business, um, alcohol, the alcohol regulations within North Carolina.
2:51
And then, you know, having that p- uh, experience of actually selling a business ourselves, um, to another operator, that was, uh, that was all kind of our first foray into legal.
3:01
So is that where the idea for DocSum came from? A bit, yeah. We really enjoyed kind of the process of, of, uh, of our legal transaction and our workflow.
3:10
And, um, where we really sank our teeth actually was later at another job called Pacaso Homes.
3:16
And so we got a opportunity to work together at a startup that was in the fractional co- co-ownership of, of, of real estate called Pacaso, where, um, a lot of our product was our transaction process.
3:28
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 le- our legal transaction workflows and, um, got familiar with some of the tooling in the space and was really inspired to, um, start a company, uh, to help out lawyers, uh, at the time.
3:44
Did you guys both join Pacaso together? [laughs] So funny enough, you know, we, uh- Have you guys been a package deal since, like, NC State, it sounds like? That's right. That's right.
3:54
You know, when we, when we joined, uh, you know, we were both familiar with...
3:58
We had a mutual friend that was working at the company, and there was this opportunity where they needed a product manager and a back-end engineer. And so, you know, it was kind of a good fit.
4:07
I remember- You guys showed up to the interview together. [laughs] That's right. That's right. I remember three months in, we were having dinner at an offsite with the CEO, and he goes, "How did this happen?
4:16
Like, how did you guys working together?"
4:18
And, you know, that was, that was a really cool opportunity, um, to be able to, you know, kind of get into trouble both, uh, at Bar Box and at Pacaso together, um, working together on the same problems.
4:30
But you saw all the transaction workflow, you saw the legal back and forth at Pacaso- Yeah... and then you guys decided to, to leave to start DocSum?
4:39
Well, so at the time, I think Pacaso was going through a lot of changes, and so they had gone through, like, three rounds of layoffs.
4:46
And it was really at the end where we were kind of, like, closing up shop as a product team. And so Alex and I both, you know, I would say fortunately, got laid off to be able to start this opportunity together.
4:57
And it was at the time where Alex was living in New York, I was in San Francisco, and, you know, we were thinking about whether or not we wanted to join another company or start something ourselves. Yep.
5:06
And that's really when, um, GPT-3 came out. I remember I had gone to a LangChain meetup at the time- Yep...
5:12
and it was only about 30 people, and 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."
5:28
And, um, met a couple other YC founders while I was there, and they all encouraged me to apply.
5:33
And so, um, Alex and I, um, you know, were tinkering on a couple different ideas and landed on, "Hey, I think we should really stick to legal."
5:40
It's something that felt like a particular pain that we were both familiar with at Pacaso and, um- Yep... probably something that, uh, we, we would enjoy doing and building as, as a company together.
5:50
And so that's when we applied to YC in March of that year. And then you guys got in. And we got in, yeah. That was really cool. There you go. [laughs] Yep. S- so talk to me about the early days.
6:00
Like, how'd you find your first customers? What did the MVP look like? Like, how, what did the beginnings look like? Yeah, the beginnings were, you know, kind of a, a scrappy prototype.
6:11
We had, at the time, the magic was being able to chat with a PDF, right? So the first- Yeah... versions, versions of Chat GPT, you couldn't have external file upload, right?
6:20
And so we built a chat with PDF app, and we made it a little bit more legal focused.
6:25
So we had some metrics that you could pull specifically about contracts, and really were thinking about contract review and building kind of a web-based, think about like a Google Docs editor for legal, and that's what we got into YC with.
6:39
And the original intention actually of the app was to build for other startups. So, you know, startups are negotiating. They typically don't have budget or time- Right... to be able to work with outside counsel.
6:50
And so our intention was to get into YC and try to kind of validate our idea with, um, with early stage companies. Got it. Got it. And how did you find those first few customers? It was in our batch, you know?
7:01
We were, you know, meeting other folks that were like, "Hey, we're signing this deal," or, "We're meeting this enterprise," and, you know, trying to test the, the, the product with them.
7:10
It was mostly early stage companies where founders were d- leading, you know, negotiations themselves. Um, and, you know, it was through the batch that we learned kind of a couple things.
7:20
One, early stage companies don't really have the volume necessary for kind of a scaled B2B kind of motion. Yes. And two, it just turns out that, uh, early stage founders don't actually negotiate all that much.
7:31
They kind of, except for- They just roll over [laughs]. [laughs] Right. They just take what we can get. Take what we can get.
7:37
And so that's when our, our, our focus towards the end of the batch really focused towards, you know, B2B, um, enterprise SAS companies focusing on in-house legal counsel where they, you know, had a perspective.
7:49
They, they were really informed about the product and, and, and the outcomes they wanted to drive and really building for them. Got it. Got it. What have been some of the biggest lessons you've had so far as a founder?
7:59
Yeah. Um, you know, I think, I think one thing that YC says during the ba- batch, and I think y- we can all learn from, is like launch early. You know, always get your ideas out there because as much
8:13
thought we have around, um, you know, putting something into the world, like oftentimes it's a little drop and a little ripple, right?
8:21
And so getting that muscle of just pushing things out there and getting feedback I think is, is one. I think another one was, you know, at the time who we were getting feedback from.
8:31
So at the time we were working on this web-based editor for- Yeah... uh, um, for building out contract review, and it was pretty complicated.
8:39
You know, we were both trying to build a legal tech platform and a web-based document editor, and you- Right... definitely have a lot of experience with- Yeah... with this with, uh- It sucks... with Audra, right?
8:48
It's really tough. And so- [laughs]... um, at some point we decided that what we were taking on was quite ambitious, and we- Yep... actually ended up pivoting the idea a bit, which I'll get to in a bit.
8:58
But, um, but yeah, you know, I think like focusing on distribution, focusing on, you know, talking to more customers, and maybe building something that was smaller and more simple, um, instead of so kind of ambitious from the get-go would've been something that, um, we would've probably taken a, a second pass at, um, if we did it again.
9:16
Shaunik, I'm so curious because as you and I know, launching early with an MVP and getting feedback, uh, is the MO that, that we've been taught. Uh, and also we've been taught that works.
9:30
At the same time, when you're dealing with a customer base that has higher standards or maybe lower risk tolerance, it's hard to find that balance and to figure out, hey, is what's not working because
9:45
it's not a real need, or it's what's not working because the MVP just didn't hit the, the minimum viable threshold that they just might have. How do you guys go about that?
9:55
You know, I think, I think that what we learned the hard way was that the minimal bar for a bu- our buyers, which are- Yeah... innately a risk mitigation role. Yes. Right? Is, is- Very risk adverse...
10:07
and they're very allergic to change as a result. Yep. Right?
10:10
And so anything outside, you know, one degree outside of what they're normally used to, um, is something that we have to take on as a huge change management challenge.
10:20
And so, you know, for example, like 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?
10:31
So we're introducing kind of a, a 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."
10:45
So, um, you know, I think, I think, uh, all of our buyers at the time and our early users, lawyers, were very, they're very forward-thinking, right? Like a lot of these- Right...
10:55
in-house professionals are dealing with innovation day in, day out. They have an appetite, you know, for the things that are new. But when you ask them the same question of, "Well, would you use this?"
11:04
I, I think it's a quite a different answer.
11:06
So, um, you know, we had to be a lot more selective about the kind of feedback that we were seeking rather than, you know, folks that are generally pretty positive about anything, uh- Right...
11:16
that they wanna support as opposed to what they're paying for. Right. I'm so curious, what have been some of the toughest lessons or maybe like the toughest times you've been through as a founder? Yeah.
11:30
You know, I think, I think one of the things that we, we were kind of deciding, we, we kind of pivoted to being more of a post signature management platform.
11:39
So the idea being a lot of businesses don't necessarily know what they've signed. You know, they have- Yep... contracts that are sitting in DocuSign or Google Drive. Yep.
11:47
And being able to become a system of record, um, that seemed to be an obvious place that a lot of the market wasn't focusing on, and was an obvious, um, opportunity because a lot of the incumbent software CLMs in the space weren't very good at it.
12:02
And so we said- Yep... "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 lovable product, right? Right.
12:14
Integrations, data extraction quality. Um, and there was a time period for about nine months where we were just kind of In the weeds building software, and we had a couple customers that were- How'd you handle that?
12:26
I found the hardest part about that journey is the mental part.
12:29
Yeah, I mean, the, it was crazy because we would, like, 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?"
12:38
And they would be like, "No, but we need X." Or- Sure... "No, but we need Y." Yes. Yes.
12:41
And there was, like, this period of just kind of utter delusion that we had to go through that, like, at some point there was gonna be a light at the end of the tunnel, and we were- Well, maybe that's what being a founder is, utter delusion.
12:53
[laughs] Yeah. Yeah, and you know, there's just, like, so many darts that we're throwing at the dartboard that, like, felt right, but just weren't sticking. Sure. And, you know, we were thinking about burn.
13:03
You know, we were also then being like, "All right, well, we just need to survive to the point that we're actually making some revenue." Yeah.
13:10
And so that changed our way in becoming a lot more, like, risk, uh, you know, we were trying to limit risk, so not making, like, as aggressive investments and maybe hiring. That- Yeah...
13:20
you know, changed our perspective. So I think, like, obviously hindsight's 20/20. You wanna, like, step on the gas now, now knowing what we know now.
13:27
But, um, but, but yeah, it was a pretty scary time in terms of is this even the right thing that we sh- we should be working on? Yeah.
13:34
Is, is, is the information that we're getting from prosp- prospective customers even the right things? And so, um, yeah, it was really hard to get good advice.
13:42
Um, and, you know, we were kind of at the edge of knowledge in terms of there was not a lot of precedent [laughs] for what we were doing. Right.
13:47
And so we needed to kind of figure out- And what kept you going during all that time? You know, it's, it was really helpful because I think, you know, Alex and I were so inspired by Linear in particular. Sure, yes.
14:00
Um, and, and we talk about this a lot because I think Linear, to us, represents a software company that is just a team of craftsmen, right? Yeah.
14:07
They, they value, you know, the artistry of building software and having strong opinion. Yeah. And as somebody who's been a PM and using, like, Jira for years, like, I dreaded using Jira. Right.
14:19
And Linear was such a breath of fresh air. And, and for us there was like, 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.
14:31
And- Right... and, and if that assumption was true, that w- somebody had to do it, and we didn't really see those examples, and so we were like, "Maybe it's us."
14:39
And so, um, you know, we, we, it was kind of this, like, kind of blind faith that, like, we could keep, you know, you know, building the best thing and, and the terminology and the, and the style and the vibe would be picked up by specific customers, and eventually it would work out.
14:55
And so it is cool now seeing, like, you know, our first 20 customers, like- Right... using the language that we use and thinking about- Yeah...
15:03
primitives and software in the way that we think about, because they're the ones that are kind of evangelizing this for other people. Right.
15:10
So I do have a little cheat sheet here, because the other thing that Alex mentioned to me that kept you guys going is you were having a lot of fun along the way. Yep. Was that a big piece of it from, from your end?
15:23
You know, I can't complain. You know, I had the opport- I was, I, I got to, I'm getting to build a company with my best friend. Alex was my best man- Right... at my wedding, right? And we've gone through- Yeah, yeah...
15:32
so much of it together.
15:33
And like, you know, 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, um, has always been a motivating, a motivation for us to even start a company.
15:49
Right. You know, I think a lot of people come into, into this space thinking that they're gonna make, you know, uh, a ton of money or they're gonna get a lot of fame.
15:56
And while that's obviously a motivation, you know, in some degree, getting the opportunity to just, like, build something cool and do that on your own principles has always been, um, the biggest privilege.
16:08
And so- Right... you know, we, we, we, we really cherish that and value that, you know, every day. You teased this a little bit, but it sounds like you have a new product or a new direction that, that's coming up. Yeah.
16:18
Can you talk about that? Yeah, absolutely. So, you know, as I mentioned, we, we, our core offering is a repository, right? A post-signature- Yep... management platform.
16:26
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?" So- Yeah. [laughs] With... Yes. Right?
16:36
They don't want to eve- invent anything new. And so what we've done is we've recognized that our platform maps that precedent.
16:42
And so what we can do is then use that information, like, kind of like mapping the DNA of the choices that they've made, to influence some of the pre-signature workflows.
16:50
So we've built two products, um, in the past couple months. One that's an email negotiation agent. It's pretty cool.
16:56
You can send a contract to an email and, you know, if Michael Wang were to, were to send that to us, uh, we would actually review that agreement, negotiate it on your behalf, and send back the red line version all authored in your name.
17:09
So- Wow... kind of a magic product that's cool. Within Word? Uh, right within email actually. We actually have a little- Oh, within email. Oh. Yeah, within email. And then the second product is an actual Word add-in.
17:20
So this is a plugin that you download from the Microsoft App Source. Yeah. Um, and then you, you know, it's a copilot that pops out.
17:27
It'll review a contract, generate red lines, you can apply it to the agreement, and really use it as, like, almost a cursor for legal docs, right? Right. It's a cursor, like, add-in.
17:36
So all of that is really, um, we would call that as a, a, as an extension of our repository, like bringing- Yeah... being able to, being able to bring that precedent right into the transaction.
17:46
So, um, you know, and, and, you know, one offering, you know, one thing that we've been doing for a lot of early stage companies is actual contract review.
17:54
So we have a number of YC companies that we're supporting today, but, um, you know, teams that don't have in-house counsel, maybe they're negotiating MSAs and order forms- Right... whether, or, or, uh, DPAs.
18:05
We set up a Slack channel. They work with us, and we're able to offer, um, you know, a flat based bill for unlimited contract reviews, um, directly- Wow... through Slack. So we do that- That's available to any startup?
18:19
It's available to any startup, and the way that we do it is, and, and we're able to actually, uh, make that profitable for us, is that we actually use our software under the hood.
18:27
So you actually have- Yeah, that makes sense An attorney- Yes... who's directly within Slack, they're working with you, um, and they'll turn around, um, you know, contract reviews in your name for you to review.
18:37
So we're not, you know, a law firm, so I just do wanna make that clear. We're not a law firm. [laughs] Yes.
18:42
We're heading toward, um, but we do offer- In, in a conversation about legal tech, we have to make sure all the disclaimers are out there. Yes. Yes.
18:50
Um, but, you know, 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, um, use that as a way to help, uh, inform some of the, and accelerate some of the, the choices that you would already make, um, and then put that, that first draft for you to review and, and accelerate.
19:08
So, you know, we have teams where, you know, the, 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, um- Right...
19:18
get all their deals done. That's incredible. Yeah. Shaunak, this is so interesting. I'd love to ask you a few questions about you as a founder now. Sure. So we talked about some of the ups and downs, the sheer delusion.
19:30
I am curious, do you have any habits or rituals that just help you reset- Yeah... get through the, the days, that keep you sane as you have an insane job? Yeah.
19:44
Um, one thing I would say is, uh, you know, things that I love to... I make sure that, like, my passions are something that I can definitely experience, you know, every day, if not every couple days.
19:56
So one of those is cooking. I feel like as- Oh, really?... as, as found- yeah, yeah. As founders, like, you know, we're working on long-term goals.
20:05
A lot of the things that we want to achieve don't happen in the same day. And so for me- Yep... being able to cook a meal where, like, I buy ingredients, cook, clean up, eat, is like I'm...
20:16
it's one of the few things that I can see from start to finish in the same day. Oh, that's so interesting. And, and I feel like having that sense of completion is one of the most- Yeah...
20:25
rewarding things because oftentimes we don't feel that sense of completion day to day. Um- That's so interesting. Yeah. I get it. Do you have a favorite dish that, that you cook? Um, I cook a lot of Indian food.
20:36
I actually started an Indian spice company with my mother, uh, called- Oh my God... Mama T's. How many companies have you started? [laughs] A little passion project when I- Yes.
20:45
But, um, but yeah, I love making a dish called rajma. It's a north- Okay... Indian red bean dish. Super hearty.
20:52
You know, tastes like Indian chili, but it's super good and I, you know, usually will make a pot of that and have it in the fridge. Can, can, can Jordan and I invite ourselves over to your apartment? Absolutely.
21:01
Ab- anytime. Anytime. We can definitely do that. [laughs] I love cooking. Um, I think that's big. Um, I also play basketball every Wednesdays with the same group of guys, you know- Oh, nice...
21:12
every, um, every week, and so that's a nice ritual. Um- Yeah... and then I think another thing is, uh, uh, daily I, I tend to wake up, I try to wake up as early as possible, and I'm usually the first- Okay...
21:21
one here in the office. But I try to take my mornings a bit slow. You know, drink a cup of coffee and then, you know, I always k-
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