- Platform: meet
- Source: Read.ai 01JF0DE4GE5Q6W6VT29AHZMPCS (via Ben Ornstein’s account, imported 2026-08-06)
Transcript
Ben Ornstein: So, but I appreciate that. It’s all good. I completely understand. It happens to the best of us. Yes. Jake Stein: And, uh, uh, yeah, I think what happened is that I had a, I don’t remember what the reason the first time was. And the second time was I inadvertently rescheduled for Thanksgiving day. And so I assume you didn’t want to actually do it on that day, but I certainly didn’t want to do it on that day, but I think I saw that and I was like, look, if Jake wants to do Ben Ornstein: it, then I’ll, I’ll set aside some time and we’ll get it done. Jake Stein: Nice to connect for sure. Ben Ornstein: Yeah, where are you based? I’m in Philadelphia. What about you? Jake Stein: Oh, I’m not sure. Ben Ornstein: I’m in Newark, Delaware. Oh, really? Oh fun. That’s great. That’s cool. Jake Stein: I you’re probably the first founder. Ben Ornstein: I’ve done like 80 of these first one in Philly. Oh, nice. Wow, that’s great. Jake Stein: And then did you grew up in the Newark area? Do you go there for work? Like what brought you there? Yes. Ben Ornstein: So I grew up in New York about an hour north of New York City, actually. And then I recently got engaged to the fiance. Thank you. And her sister had a house here in Newark. And so we’ve been living here for a couple of years now, just with them, getting ready to move out at some point, but yeah, that’s what brought me here. Jake Stein: That’s great. So I grew up in Northern New Jersey, not too far from Newark, New Jersey. Okay. I now know it’s a very different place than Newark, Delaware, but I remember hearing some people mention Newark, Delaware, thinking like, but not making, not realizing it’s a different place. I was like, I think you don’t know what you’re talking about. Like, I know Newark is a really nice place. Newark has some challenges, but anyway, cool. That’s awesome. Where did you grow up? Ben Ornstein: Just out of curiosity. Jake Stein: It’s a town called Montville, it’s in Morris County in New Jersey. Ben Ornstein: I grew up in Westchester County. So I know Montville, I know exactly There you are. Oh, that’s awesome. Jake Stein: Very cool. Nice. You mentioned you’ve done like 80 of these. How long have you been working on Founding Journey for? Ben Ornstein: Yeah, so do you know Michael Hauk from Hauk’s newsletter? I feel like that name sounds familiar, but I definitely don’t know him personally. Yeah, so he is a founder who is, he raised 10 million for his last company from A16Z. He created an email newsletter for founders and startups in DCs It’s specifically for founders, but that is who kind of is a subscriber of the newsletter. And it was 100k at peak. He’s intentionally decreased that number, but he built a few businesses around that audience. So he’s a personal holding company and a few of those businesses are a startup. He’s done a whole bunch of stuff. He rebranded Hauk’s newsletter to Founding Journey. Founding Journey has, it involves a podcast that we started together. It involves just the newsletter that he does like three times a week, and then these case studies. And the case studies came from a resource that he wanted to create for founders specifically related to fundraising. And he figured what better way to do that than by actually speaking with founders who have done it. And so that was, you know, that’s where this, from And that’s what this call is about today. UNKNOWN_SPEAKER: Great. Jake Stein: How often do you do the fundraising case studies? Ben Ornstein: Oh, man, I’ve done a ton of these. I do them very often. It’s so cool. It’s been founders from all over the world, different industries, different stages. Each one of them is unique in their own way. Awesome. Yeah. And so just some more details about this. We have the read AI guy in here because I take the transcript from this call and turn it into a text-based case study. It goes towards our premium subscribers. So it’s painstaking for them to do. However, you still get the exposure to the entire email list because each Saturday we send an email saying which new case studies were added. So you still get exposed to the whole list. You’ll also get a draft of this beforehand. So you’ll be able to check it out before you give us the go ahead kind of thing. Jake Stein: What’s the typical turnaround time? So we’ll do this today, like how long until the case study is live typically? Oh, pretty quick. We can move very fast. Ben Ornstein: Is there a deadline or? No, no, no, just curious. Jake Stein: Like, you know, sometimes like I’ve done an interview one time where it was like, oh yeah, it’ll be quick, like four months. And then someone else was like, oh no, this is going live tomorrow. Ben Ornstein: Okay. Yeah. We can get it from the time that this is done. I can get it. Jake Stein: We can get it posted within a week. Okay. That’s cool. Saturday newsletter, will there be a link to our website? Ben Ornstein: Um, I think how it works is it’s a link to your LinkedIn. Okay. Yeah, which I guess in turn would be we could potentially Yes, I would. If it’s up to me, I would say link to the website. Jake Stein: I mean, both would be great. But it’s not like I’m not gonna be pissed if there’s not. Ben Ornstein: It’s just it’s a plus. Yeah, I’ll chat with talk about it. But um, Yeah, any other any other questions? Um, no. Obviously, this is pre recorded. So if there’s anything that said you’re like, Oh, wait, actually, um, just let me know. So all good. All right. Well, with that, Jake, please briefly introduce yourself and your startup. Cool. So my name is Jake Stein. Jake Stein: I am the co founder and CEO of common paper. Before this, I was co founder of two other b2b software companies, one called RJ metrics and data and that was acquired by a company called Magento. The other one was called Stitch, it was in data integration, that was acquired by a company called Talend. Common Paper, the company I’m working on right now, our big picture vision is to turn contracts into APIs. And there’s two components to how we’re doing that. One is standardization of the contracts themselves. So sort of like what the SAFE did for early stage fundraising, where it’s a template contract that lots of companies and lots of investors users use, and it makes things easier for everybody. We’ve created what’s effectively the safe for software sales. So it’s a bundle of contracts that are created by a committee of a little over 45 attorneys. And that’s run sort of like an open source project, where only one of those 45 attorneys is actually an employee of common paper. The other ones are from companies like Salesforce and Thomson Reuters and Confluent. And they all contribute and argue and debate over what ought to be in like a sales contract or an NDA. And then we package those up and then release them under Creative Commons license. So anybody can grab those and download them and use them for free. And then the other side of our business is we make contract management software. So you can grab a Word doc from us and then use it in anything. But our goal is to be the best home for those contracts for customization, negotiation, proposal, signing, tracking, and then using the data in all the different applications in your business. And that’s where that API vision into reality. So like, for example, if you want to sign a sales contract, we can automatically, through our integration with Stripe, use the structured data in the contract to instantly create a subscription, invoice your customer, and get you paid right after your customer signs that contract. So that’s like our most popular integration off that contract API. I’ll pause there. Does that all make sense so far? Ben Ornstein: Yeah, really cool. Really cool. Sounds really interesting. Jake Stein: Yeah, of course. And so, you know, what can you share about the fundraising journey? Ben Ornstein: So this could include, you know, how many rounds of funding you’ve raised, the amounts you’ve raised, if you’re comfortable, but of course, no pressure, the valuations, and how long they took to close. Totally. And just to confirm, you want to hear solely about common paper? Jake Stein: Are you interested in the other ones? Ben Ornstein: I’m happy to talk about all of them, but the case study will probably be centered around one company. Jake Stein: Cool. And so just for context, before this, in my first startup, we bootstrapped for the first three years. We ultimately went on to raise about $25 million in total. So Common Paper is a seed stage company. We've raised $7 million in total, different than my prior thing where here we raised right away. So we raised a seed round that was led or co-led by Bold Start and Uncork. And then we actually did Y Combinator after our seed round. I can get into why and that later. And then we raised a small seed extension right after YC. And so it’s like if you add up the initial fundraise IC money plus the extension, that all gets us to 7 million. UNKNOWN_SPEAKER: Awesome. Very cool. Ben Ornstein: And what did you plan to use the funding ahead of time for? Jake Stein: So we knew when we were planning out Common Paper, and when I say we, it’s my co-founder Ben Garvey and I, that there were some unique things about Common Paper where it’s a business where it would take a little while to get going, because I talked about that, like, committee of attorneys and this open source project, where I think like, if you’re just building a random b2b software product, and I say that with no dispersion, I’ve done that before, I have a tremendous amount of respect for people who do that. And like, I use a lot of products like that. But you can pretty quickly, hopefully, create something that’s valuable, and start charging for that, you know, if not on day one really soon. But our strategy about like building credibility in this standard. And so like me and Ben, we’re not lawyers. And so like, we knew we would have to number one, like recruit a really fantastic lawyer. And then also to be like a member of our teams that was like one of our very first hires. And we have this amazing person named Tiffany and she has amazing experience I’m happy to go into. But then also, like we didn’t want this to be just Tiffany’s idea. We wanted this to be sort of like representative of the market So going out, finding the right attorneys, giving them the time to structure these things. And then so like trying to build up this credibility where this would be actually be a standard. People would see this as a very legit thing. We knew it would take some time. And so we knew this was a business we would have to raise money upfront for, as opposed to let’s start building, let’s get traction and then use that as evidence. The other thing that was different than what I’ve done before, is that I was really fortunate to have a successful exit behind me. And so I think it just made fundraising based on a slide deck easier than when I was raising at the beginning of my career, where it was like, hey, I swear, I’m great, that I’ve got more proof points now Ben Ornstein: than I had. Awesome, now that makes total sense. And when you were deciding which investors to kind of bring on board? How’d you decide who would be a good fit? Jake Stein: Yeah, so we were fortunate on a number of dimensions. Like we were, it was, I think a good time in the market to be raising a seed round. And we had a number of options, like a number of, like we didn’t go on a really exhaustive thing, but we were talking to people who either we knew personally, or we had like, strong one degree connection to, or like had like extremely specific domain expertise in what we wanted to build. And we had a number of term sheets for basically all on like really great terms. And so it was like, and again, I’ve had fundraising experiences in my life where I like went out, spent a couple of months and then came back with zero. So like, this is not all sunshine and roses. But in this time, we did really fortunate. We had, I think it was actually four term sheets that we would have been really happy with any of them. And each investor brought something a little bit different to the table. The reason we ultimately chose Bold Start and Uncork, they had a lot of things going for them. But the thing that sort of tipped it over for us was that we had worked with both of them before. So they had invested in the prior things. And so we knew how they We knew how they acted in good times. We knew how they acted in bad times. We knew that when they said they were going to do a thing, they actually did a thing. And there were certainly times where they could have made our life way harder. And it’s not like they were always nice to us. They would give us tough love or say, hey, I think you’re wrong, whatever. But just that level of trust is something that it’s hard to duplicate that with someone who you’ve had a couple of conversations over a month or two. That was like ultimately the deciding factor of why we decided to work with them, those two firms, as opposed to anybody else. Ben Ornstein: Makes so much sense. I mean, if you already have that trust, and if it was successful in the past, I mean, why not? Right, exactly. That’s awesome. And so this question, it’ll be kind of obvious, and then you’ve kind of already answered it, but how do you get in touch with these investors? The answer is, of course, you worked with them previously. Jake Stein: Yeah, so I worked with them briefly, but one thing that I think is potentially a little bit unusual is that I reached out to both of them somewhere between three and six months before we decided to go start fundraising. Oh, interesting. So after I left Talon, that was the company that acquired Stitch, I took some time off and started doing research for what would eventually become Talent Paper. And it was a lot of like customer development and thinking and getting people’s advice and also like starting to talk to Ben to try to, you know, sell him on this. And cause he had a great job. He was a senior engineer and like has had an amazing career at a bunch of different companies, including one where we worked together, which is how I knew him. But one of the research calls I did, or one of the batch of research calls I did was with Ed from Bold Start and first Jeff Clavier and then Andy McLaughlin at, at Uncork. And this was like, no slide deck. It was not, hey, I’m raising money. It was more like, here’s this thing I’m working on. What do you think? Are there people you think I should talk to? Do you think like, if I was pitching this to you, what would get you really excited? What would you be skeptical of Like, what sort of evidence would you be looking to address that skepticism? Like, you know, just basically doing customer but instead of for customers with investors. Exactly. It was investor development. And like, those are really great calls. Cause like, I wasn’t trying to come away with a term sheet. I was trying to come away with like, basically tell me the questions that are going to be on the test so that I can, as, and like, I was already planning on doing more research, more prep, more thinking about this. I’m thinking about like, I mean, cause these, it’s not only what do I need to do in order money from these people, but also these people are really smart. So if they have questions that I haven’t thought of, or if they have skepticism that I don’t have, I should think hard about that and think like, do they just not know what I know? Or are they should I try to find that out? So that was really helpful. And I did that with, you know, a few investors. And so when I we were ready and said, Okay, you know, Ben’s quitting his job. Jake is going full time on this. It’s not like my time off anymore. I’m like, going full speed ahead. We were able to sort of hit the ground running and say, okay, we’re ready to go. Let’s talk again. Here’s like the deck and oh, by the way, we’ve got answers to all these questions that you had. Ben Ornstein: So I think that helped a lot too. Yeah, no, totally. That’s, that’s really interesting. And so I actually, this is gonna be interesting, because I don’t, if you think about the process as a funnel, you know, how roughly how many investors did you reach out to? This could be cold, this could be like intros. What subset of those turned into initial meetings and then ultimately maybe even like second, third meetings. And then ultimately how many ended up as investors? Jake Stein: Rough numbers, obviously. Yeah, yeah. So I’m pretty confident I reached out to zero investors cold. Yeah. I definitely got some warm intros from people I think I probably, and again, I know this is abnormal, but I think I had first calls with maybe eight investors. So like maybe three or four I knew personally. Actually, no, I’ll take that back. Yeah, three or four I had some personal connection with, I could just reach out directly. And then the other three or four, yes, by six to eight total, three or four I knew personally. Got a warm intro to because, you know, I like the other thing I did when I was thinking about this is like, I asked a few close friends, either who are investors and maybe like later stage funds, or founders who like I know really well, like, if you could invest from anybody from the world for this kind of business, who would it be? And then they say, Oh, you know, my person XYZ is like perfect for this because of the reason. So it’s probably like 5050 between one degree warm intros, and my personal connections had called with 100% of those, probably had second calls with something like 50% of those. And then ultimately, like got to a term sheet with 100% of those. Yeah. So again, again, I know that this was the most successful fundraise of my life. And I’ve had some where the 100% conversion from second call to term sheet. I’ve also had the zero. Ben Ornstein: Yeah. Yeah. I mean, look, the previous success for two companies certainly helps. That’s awesome. Very cool. And so when you were pitching, you know, what did you emphasize in the pitch? Jake Stein: The thing that I, like, I think when I thought about it, it was, you know, like, this is a problem that, like, I didn’t need to spend any time convincing people there was a problem. Everybody who’s involved in B2B software or any B2B sales, really, knows, like, hates contracts, thinks they’re annoying, thinks they’re a pain. So, like, sometimes I would give a little bit of preamble for that, and certain investors would be like, yeah, yeah, we know, we know it sucks. Let’s fast forward on that. So I would, like, sometimes just try to connect, like, my experience to that, and then just, like, talk about I validated this with a lot of people. Basically, and then the big points I was trying to say are, like, This is a huge problem. This is a gigantic opportunity if we can solve it. And not only there’s a big market opportunity just to solve this, but this turning contracts into API opens up other adjacent really big markets. So it’s a big problem, big opportunity. Opportunity is actually even bigger than you realize. And then here is what we think the right wedge is for how we’re going to go from nothing today to getting traction. And then a little bit about like, we think we’re the right team to do it. We’re legit people. That was the main pieces. Very cool. Ben Ornstein: Off the cuff question, this is not on, this is just out of curiosity. Did you think about like a verticalized approach where like, get the nudge in and then build upward in a certain niche? Yes. Well, yes. Jake Stein: And we ended up going, after working on it for a little over a year, going even narrower. I first started saying, we’re focused on B2B, so actually B2B SaaS. And that was gonna be like our critical mass where we focus. And then ultimately after working on the business for a little while, we realized we should go even tighter and say very early stage B2B SaaS. So like the idea is, can we get in front of all these founders, basically when they get their first verbal yes from a customer or a design partner, and then the customer says, hey, send me a contract. And the founder says, oh crap. Okay. Like that’s like the moment when we got any, we have people that start using us after and like now many of our early stage customers who started using us then have now grown and raised seed A, B rounds. But we decided to like get narrower. And that was a big needle mover for us. Oh, I can imagine. Ben Ornstein: That’s awesome. Very cool. And you know, when you were fundraising and and trying to like close these investors. Did you do anything to drive urgency among them? Any FOMO tactics? Jake Stein: Was it even needed? I mean, I was transparent about the fact that I was talking to other people. And then like I did tell them, like when I got a term sheet from one, I would tell the others. And that certainly gave us more negotiating leverage. Um, but I don’t think, uh, I think the other thing that I did was just try to set expectations that like, I’m starting this process and I don’t remember exactly what I said, but it was something like, you know, I’m having a few of these meetings. I’m hoping to decide the partner we’re going to work with relatively quickly. And I think I may be, I think the other thing I did is just ask them, about their decision timeline like you know because I want to be respectful to that but I also want to set my own expectations and then that’s also something that’s helpful for potentially holding them accountable later like it was not an issue this time but it’s the same thing again if you’re doing sales to like you know because then if the customer drags it out you can say about I thought you told me that this was really urgent and you needed to get make a decision in three weeks it’s been six weeks um so I I try to ask that with investors and partners as well. But this time, I think the thing that really helped, and it helps with a lot of negotiations, is just having credible alternatives. And I think that lit a fire under everybody. And the other thing that was just, I had never experienced anything like this before, where it was during the pandemic, and so everything was on Zoom. So I could in the morning pitch someone in California, and in midday pitch someone in New York and then in evening pitch someone in Texas or Florida. And like that also just like, that made things great from my perspective. Yeah. All from one place being able to do that. I was sitting at home in my pajama pants and it was all working. Ben Ornstein: That’s incredible. Yeah. It’s such a, like a different environment. That’s awesome. Jake Stein: It was. And I remember like for my prior company, just like flying to California from Philly for a partner’s meeting and like being totally and then like flying home the next day with my co-founder from the prior business, Bob, and then just finding out, oh, we didn’t make it. Like, oh wow, well, we’ve lost three years of our life. We spent whatever, 2000 bucks on flight and hotel. And maybe we’ll go back next week if someone else wants to bring us out. Ben Ornstein: And so this is a very different dynamic. That’s crazy. Yeah, that’s such a big difference. Yeah. So obviously looking back and talking about it, like kind of surface level, it’s like, oh, it was all sunshine It was so easy, but I assume there were some challenges that came up during fundraising. Jake Stein: Oh, for sure. For sure. And the other thing that I should say is that Bold Start and Uncork were like the co-leads. They weren’t the only investors. And so we also have like a great group of angels and like another fund called Crew Capital invested in the seed round. And so like one of the challenges was like, honestly, Like, I don’t remember how the exact dynamic, but like, well, starting on Cork invested the majority and then, you know, minority came from the other folks. And it was actually much easier to invest, like to get the vast majority of the money than it was to get the, like, whatever, 10 or 20% that was left over. Because, you know, I really wanted to have, and I think we did end up with a great group of like angels and people who have really relevant expertise and people I really respect, but it’s just a lot of one-on-one conversations. And some of them, I think, were people who had not invested in startups before, and some of whom were attorneys. And so they were attorneys who knew a lot about companies and legal stuff, but were just not familiar with the norms of startup investing. And so these people who I’m sure have a lot of great things going for them, they were just like, okay, cool, I’ll check it out. Please send me your articles of incorporation and your charter and all these things. And I was like, I don’t really think- That’s not usually what they ask for. That’s not what they ask for. And I don’t think that’s what you should make your decision on. Either you trust us that we’ve done that well, and it’s not the thing that’s gonna make us make a break. And so there was just like a lot of time and it was like a slog. And I think what I should have done is either time box that, honestly, I should have created more urgency with the angels because there I was just like, yeah, we reserve this chunk of money. We have like an angel list rollup vehicle. And like, in one way that made the logistics really easy, cause I just sent them a link and said, go, but in another way it made it really hard and it made it drag out. And it was just like a lot of one-on-one communication, a lot of one-on-one on one meetings, a lot of one on one, like, follow up answers to data. And I didn’t want to, like, tell someone to go pound sand, because they were only investing $10,000. But in some ways, like the problem, it wasn't that I didn't care about their questions, it was that there were a bunch of them, right? And they had slightly different things. And so that was definitely a distraction, and annoying. And at some point, I was just like, you know, at this point, like, it's a tiny amount of money, I don't really care that much, it's not gonna be real Should we just say, I don't remember what the number was, should we say the last like 30K we don't care about rather than me be distracted for the next two months wrangling these up? What we ultimately did is I think, look, we had a few in progress. I just said to them, hey, there's a deadline now and I just made it up. And I think the other thing is that we had had some people who wanted more than we originally gave them. So like there was, And the final thing, I just said, hey, I limited you at 10. You said you wanted 50. There's 17 more. Do you want it? They were like, yes, done. And they did it in a day. So I think we wrapped it up that way. But that's maybe one thing that was not great about it. And I could have done better if I was going to do it again. UNKNOWN_SPEAKER: Yeah. Ben Ornstein: No, that's a tough situation to be put in when they're not moving quick enough. But you clearly have that leverage. So it was like you were able to be like, all right, here's this. It was a fake deadline, but it was a deadline that you have leverage. True, true. Jake Stein: Because it wasn't going to be a problem for the company if we didn't get their money. And then also, I think we could have just gotten more from both Star and Encore too. They would have been very happy to invest more. So yeah, it was... I made it, it wasn't fake. Ben Ornstein: I made it real, but it was... You made it real, right, exactly. Yeah, 100%. Yeah. That's really interesting. And were there any other interesting or unique stories that that came up during fundraising that you haven't brought up yet? And sometimes the answer is no, and people go different directions with this. Jake Stein: So the other thing that I thought was very enlightening for me was it was not that initial seed round. It was in the fundraising right after YC Demo Day. And would it make sense to talk about that now? Yeah, yeah, go for it. Yeah. First of all, YC, the demo day is like an unbelievable dynamic where it's tremendous, gives tremendous leverage to the startups. I had some unique challenges around then, which like we knew going into YC, but we decided to do it anyway, where my first child, like my wife was due like right around demo day. And so my co-founder, Ben, he did the presentation. He did an amazing job. It. And like, we were sort of like, debating, you know, we didn't need more money at that point. And so we were just like, demo day is such an amazing opportunity to fundraise. Do we actually want to raise more money now? Or do we want to just wait to, you know, until we're ready to do the Series A And so we sort of debated it. And we decided like, we probably won't regret raising more money on great terms. And like our existing investors They were really into it. They wanted to put more money in, which I, again, appreciated. And so we ended up, like, letting a lot of those leads cool because, like, I was on leave for a little bit because my daughter had just been born and I was, you know, a zombie. And Ben would just, like, reply to those people. He was like, yes, cool. Jake's out. We'll follow up with you. We did ultimately, you know, raise the additional money and it worked out great. And we got what we wanted and a good group of additional investors and more money from the existing investors. But one of the things that I like, it was interesting, number one, both like the drop off rate of like people who were interested the day of demo day versus people who were like still interested, whatever it was, three or four weeks later, when I was back and ready to have those conversations, like it was, it dropped off a lot. And I don't know how much that would be true. I'm sure there'd be some drop if we were doing it the next day, but I think it was a lot. And I think a lot of people raise vehicles that are directly tied to Demo Day. And then the other thing is that because we wanted all those people to be in an AngelList roll-up vehicle, and we wanted, there was a new one that we set up, and we were doing a price round and not a safe, that created a challenge for a lot of those people, again, because I think they are like raising mini funds that invest in YC Demo Day And the expectation is number one, they're going to invest in a very small period of time and they're going to invest 100% in safes. And so we did find great people that invested, but there were some people who were like, I'm in, let's go, I'll write the check. And then I would say, cool, here are the terms, here's the AngelList thing. And they were like, okay, I'm totally fine with that valuation, but I can't invest in a priced round. And I can't invest through AngelList. I need to do a thing. I didn't really care that much about, you know, whether like the exact structure, I care about the ultimate economics a lot. And I care about the logistical overhead. And I talked with my attorney, and he basically said, we set this whole thing up on the assumption that everybody would be going through this other path. We could absolutely change that. But he's like, before I do that work, let me break out to you what the legal fees will be for that work. And he's like, you can decide to do that. It would not be crazy. But like, a significant portion of the check this person is going to write is going to go toward the legal fees for making it happen. And so I was like, yeah, I don't like I, again, we were very fortunate. We had more interest than we had space. And it wasn't like the one that the handful of people that that was an issue for were like, 10,000 times better than the other people that were flexible. And like, we also had at least one person who was like, okay, my fund is not set up to do this, but I'm allowed to have, I have like, whatever, 10% of the fund, I can do whatever I want. And so I'm gonna put you in that 10%. And they're like, situations like this, where it's just like the logistics are where. So that was a, at least the thing that was unique to me. I don't know if that comes up with that for other companies too. Ben Ornstein: No, that is interesting. And it kind of, to me, is interesting for your company's use case, where it's just like, just clean. It's not exactly related. Yeah, you see what I'm getting at. Jake Stein: Yeah, absolutely. Like the legal friction, like makes deals not happen or makes deals happen differently. And also I think the other thing that I'm incredibly grateful for is that I have an attorney who like, and I've now worked with him for almost 15 years, where like I ask him for something that's gonna make him a bunch of money. And he's like, hold on, I think you don't want this. And let me make sure you think And that I think is rare and valuable and something that like, yeah, I really appreciate. Ben Ornstein: Oh, 100%. I don't think many attorneys would say no to money. So that's really cool to have that. Jake Stein: And I think he's really optimizing for the long-term relationship because he knows, you know, this is not about, can I make, can I build the most money from Jake today? It's, we've been working together for a long time and keeping that going. Ben Ornstein: 100%. That's awesome. If you were, Talk about fundraising advice to other founders. Jake Stein: What advice would you give? I mean, it's something that ideally you spend as little time as possible on. And I think there are some people who really enjoy it and find it interesting. And my co-founder from the prior business, Bob Moore, he is great at it. And he loves it. He loves deals. He loves playing poker. He loves that and like I think that's awesome. And he's done like with his current company He's done a great job and it raised a ton of money Like I sort of view it as a necessary evil where like I like dealing with investors. I think they're smart But like I just don't get energy from this process I would much rather be doing customer support or selling someone new or talking with our team about like what Nick the next feature we're gonna build so I try to Like it's really important to raise money and to have good partnerships but I try to control the amount of time I spend on it. The other thing that like, maybe two other things that I think are like not, I think a lot of people know, but maybe they don't take as seriously as they should, is that one, raising money is like mostly a one-way door and who you raise money from is also mostly a one-way door. And so like, if you are a bootstrap company today, And you decide, like, you can always, you can't always, but you can go from bootstrap to raising, to being a VC backed company. It's like very hard to stop working with investors. Like it happens that people buy out their investors or something like that, or get a different partner from the fund, but it's not very common. It's not easy. It's a big distraction. And sometimes you just can't do it. And so like, oh, and then like, raising money converts wins into losses. And by that, I mean, like, if you're just two co-founders, and you haven't raised any money, and you sell the company for $5 million, that is awesome. You are rich and you, you know, it’s an unambiguous win. If you are two co-founders, and you raise $7 million, and then you sell the company for $5 million, that is a loss. And you, at least according to the contracts, you end up with $0. And your investors are like, you know, bummed. And like, so like that, that same outcome goes from being a win to a loss. And there’s a lot more companies that can be sold for 5 million than 100 million, and a lot more that can be sold for 100 million than a billion. And so thinking about what like, you’re going down this path, it’s hard to reverse. And that like these people that you’re going to work with, It’s like really, it’s harder to stop working with a VC than it is to get divorced. And so you’re probably going to, you know, if things go well, you’re going to work with this person for a decade. And so just thinking, is this someone you’re going to be excited about talking to and working with? Or is this someone who’s going to like, make you feel like crap for the rest of the time? And the person really matters. And I think it matters. I mean, the valuation, the economics, all that stuff matters too. But also just like, you’re going to die someday. So like, how do you want to spend your life? Ben Ornstein: Great way to cap that off. I completely agree. That’s awesome. Those are great pieces of advice. If you were to recommend an investor, who would you recommend other founders work with? Jake Stein: Oh, I mean, I absolutely love Ed and Andy from Bold Start and Uncork. Like they’re fantastic. If I was starting a new company tomorrow, they would be the first people that I talk to. No question. I think YC is also just like a singular thing. Like it’s not necessarily the right thing for every founder and every business, but it was like tremendously valuable for us. And I think it’s like really special and unique. So I definitely recommend that. And I think that the folks at Crew Capital, they’re not someone who I worked with before. And they’ve really like, I started talking to them when it was just like Brandon and Daniel, two UiPath executives. And then now they’ve really built out into a fund. And I know a lot of the people there and I think they’re great. So they’re really fantastic. So like, yeah, I mean, this time around I’ve had really great experience with all of them. Ben Ornstein: Amazing. Are there any resources you would recommend to other founders? This could be books, podcasts, newsletters, really anything. UNKNOWN_SPEAKER: Yeah. Jake Stein: Lycee has some template decks that they make available and they’re like extremely lo-fi. It’s just like, here’s the 10 slides you might wanna do. Here’s the order in which they are. And I absolutely use those starting point, even before we did YC. What else? One thing that I take for granted is like, I actually the first few years of my career, I worked at a VC fund. And so like, I think I take for granted just like, you know, what is the difference between convertible preferred and participating preferred? Like, what is a pre money cap versus a post money cap? Like all that I sort of like, I’m fortunate that I had to know that for my job. I actually don’t know the resource for someone who does not have the benefit of that experience. I would say like, I’ve heard there’s a book, Venture Deals, I think Brad Feld maybe wrote. So like, I think he’s really smart. I haven’t read that book, but I would read that or something like that, just so that I knew like what the vocabulary tab was, like, I don’t think the goal is to be the master deal structurer. Like, again, I think that’s something that most people should spend as little time as possible on. But just so that like, and then even I who have, like, I have way less experience compared to a typical VC, but I have way more experience than that compared to a typical founder. Like, there are there have definitely been times where an investor and this is not the current company, but in the prior company, investor suggested something to me. I thought, oh, that sounds good. But I didn’t do the math. And I was like, oh, that is not nearly as good as it sounded. And they weren’t lying. But I was like, oh, wow, yeah, they are more sophisticated than I am about this. Ben Ornstein: So it can definitely help, just again, to be able to have an intelligent conversation about it. 100%. And our last question here is, do you have any hot takes regarding the fundraising process? Jake Stein: Hmm. Ben Ornstein: You can take your time. Jake Stein: Some people take as much time. We’re in no rush. UNKNOWN_SPEAKER: Yeah, yeah. Hot takes. Jake Stein: I think the brand of the VC fund matters almost not at all. I don’t know how hot this take is, but I think the person you work with matters an insane amount. But like, I mean, maybe it helps with recruiting a little bit, but like, I guess just not in my experience. And yeah, I think it matters so much. Like, who is the human you’re going to do check in calls with? Who is the human that’s going to be at your board meeting? Are they going to be like, slowing you down or speeding you up? Stuff like that. But like, whether it’s the fund that like, everybody knows the name or not, I think it really doesn’t matter. Yeah, and then here’s one other thing that is like, I’ve heard a number of people say this, and I really like it. And the most recent, maybe the first person I heard say this was Bob, my co founder for the prior company. It was like, nobody’s coming to save you. Where it’s just like, if you think, oh, great, we’ll get that great investor will get that great fund and they have the team that does X, Y, Z, and then they will solve our problem. Like, no, you have to solve the problem. And a great investor can certainly help and they can pour fuel on the fire, but they can’t help you get product market fit. They can’t hire a great team for you. They can’t do great customer support for you. They can really just like amplify what you are. It’s sort of like people say power corrupts, like power actually reveals. And so I think the investor is going to help you do more of what you’re already doing. And that’ll be either good or bad. It is a good investor. And then a bad investor can absolutely slow you down and sap your energy. Ben Ornstein: I love those. Those are so great. Jake, this has been a ton of fun. I’ve really enjoyed it. How big is the team now? Jake Stein: Oh, so we’re eight people. So still relatively small. UNKNOWN_SPEAKER: Wow. Ben Ornstein: So you eight people who have and you’ve raised 7 million, I think. That’s pretty amazing. That’s awesome. Very cool. And why choose Philadelphia to stay in? So I originally came to Philly for the prior company. Jake Stein: So I was working in New York for that VC fund. That’s where I met Bob. Bob had like, was growing up, he grew up in the suburbs outside of Philly. And like before we ever talked about starting something together, he was moving back here I already bought a house there. And so when we started talking about working together, he was like, by the way, like I’m leaving New York. And like, I had gone to college in Philly and had a great experience. And so I was like, sure. Oh, and we were going to bootstrap that company. So it was going to be a lot easier to do that in Philly than in New York. Oh, that’s for sure. And then after working here, like I think ultimately for RJ Metrics and Stitch, which we have the benefit of being sort of a bigger fish in a smaller pond. So that helped us with certain kinds of recruiting. And ended up, we built a really great community of team members and friends. And then I met my wife here. Her first job was in Philly. And so now, Philly has become home. And Common Paper is totally distributed. So we have about half our team is based in the Philly area, half is spread across the rest of the United States, and the half in Philly are people that, like, my co-founder Ben, he and I met because he was an engineer at RJ Metrics. And he eventually, like, he started as an entry-level engineer, got promoted, got promoted, got promoted. And by the time we got acquired, he was, like, leading the engineering team. But, like, now it’s just, like, he, you know, grew up right outside the city. No, I’m sorry. He has lived outside the city. He grew up, I forget where he grew up. He’s a couple places. But in any case, this is just a home for us and we feel like we’re hiring great people from all over and so we could stay here and do that. Ben Ornstein: That’s super cool. I love to hear that. I’m so big on the remote, if you can. Yeah, there’s trade-offs too. Jake Stein: Like there’s stuff that I miss about being a person for sure. But yeah, it seems like the right fit for us. Ben Ornstein: Really cool. Awesome. Well, yeah, thanks again for taking the time here. I really enjoyed I’ll probably get this to you Monday, Tuesday, Wednesday at the absolute latest. Sounds good. And yeah, we’ll get it live as soon as we get to go in. Sounds great. Amazing. Great to meet you, Jake. Likewise. Thanks, Ben. Jake Stein: Have a good one.