Evan Schneyer is Co-Founder & CEO at Outlaw

Outlaw's Co-Founder and CEO Evan Schneyer started his first tech company nearly a decade ago. It later sold to TripAdvisor, and the experience left him inspired and determined to build a platform that would help users through the contract process. That's when he and his co-founder created Outlaw, an end-to-end contract management platform.

Tony Zayas 0:04
All right. Hey, everybody! It's Tony Zayas. Andy Halko is my partner. How you doing?

Andy Halko 0:11
Good. How are you doing, Tony?

Tony Zayas 0:13
I'm doing great. Thank you.

Andy Halko 0:14
Anything new? Anything new on your background that we haven't seen before?

Tony Zayas 0:20
I hope so I think. Yeah, I have to Yeah, I got a sensor that at some point, possibly if I

Andy Halko 0:31
Stop drawing dirty pictures back there, so I can.

Tony Zayas 0:35
Yep. So welcome, everybody. This is the SaaS founders show. Again, I'm Tony Zayas. Andy Halko is our founder, Insivia. And we have a special guest today. This is second week of our live show. So we're excited about these to be able to do these live. And just to let everyone know, if you have a question or comment, and you're watching live, then by all means, go ahead and just type in your comments section, we get kind of a unified feed, depending on where you're viewing this should be able we'll be able to see the responses, and we'll we'll get to those. But with all of that, let me go ahead and let's bring on our guest for today. We have Evan Schneyer from Outlaw. Evan, how are you doing?

Evan Schneyer 1:19
Hey, guys, I'm good. Thanks for having me on. How are you guys doing?

Tony Zayas 1:23
Real good. Thank you.

Andy Halko 1:24
Yeah.

Tony Zayas 1:27
Yeah, so this show, we like to talk to different SaaS founders, just hear a little bit about their story. And so I guess I'll just kind of kick things off and just ask you a question. And we're happy for the conversation to go wherever it goes. But you got a pretty interesting background. So we really want to learn all about Outlaw, dive into you know, some of the other experiences you've had and the things you've done along the way. But I would love to hear something that you talked about in your LinkedIn profile was just how you're, like pretty passionate about building a great team. And I'm just wondering how that, that interest, and that's being something that you really enjoy doing? How does that like parlay into your work at Outlaw and like something I saw at the site was your core values. And I thought those are interesting. So I'd love to hear how that plays into it.

Evan Schneyer 2:19
Yeah, sure, I think that I do, it's kind of a byproduct of that, for me, it's, I'm a Product guy. And so it's always kind of the product idea and the business idea come first, and the team kind of rallies around that purpose. And then I tend to realize pretty early on, and I've done this, I don't know, depending on what I count three or four times now kind of full cycle. And pretty early on, you know, after it gets to maybe two or three people, even just starting from some cofounders, it's, it can't be the purpose. You need a kind of a power of purpose to rally around. But that's a very, very close second. And it's just, you know, we're going to be spending so much time and energy and focus, doing this thing, whatever this thing is that you got to be doing with people you love, and supporting each other, you know, and there's really no place for ego. And for competitive kind of internal competitiveness, especially on a startup, you know, you're kind of the world is against you already, just because you don't exist yet. And so you got to band together. And that experience is really, just really a delight, I would say it's very challenging as well, especially now, with kind of startup culture becoming mass, I would say there's a lot of people who, who think they want to do a startup or think they're ready for a startup who are not, and vice versa. Those are some of my favorites. People who don't never have, never had that ideal. And, and kind of just are looking for a job or something. And then they fall into it. And they're and they just really take to it and they love the feel of the uncertainty or maybe not the uncertainty, but they love it. They just adapt very, very fast. And those are some of the best people. And then of course, there are people who, I guess like myself, who have to have to be our own bosses and have to be founders and can't really can't really work for anyone else and be happy. But yeah, actually on the team side, we've recently hit a personal milestone for me, which is that we are now at 14 our total team size is 14. And the my first startup waterslide, we peaked at 13. That is a, that is not a success, a primary success metric. But it's just only something I realized as a byproduct of, of our growth and a cool realization to have.

Andy Halko 4:48
Yes, it's interesting with that number of people. So I've had my business now for 18 years. And I'll tell you the first half of the business it was I don't know there was something inside me that said Oh, it's about the number People. And I think as I've matured and got older, there are obviously different things about culture and profit that come into it. And so I think more the interesting fact is kind of your evolution as a founder too. And for people that are just starting out of like, what you determine success means for yourself, you know, and so, I mean, and I'd be kind of curious to turn that into a question of, you know, how do you define success now for yourself, and moving into the future now that you've had a couple experiences and different things like that?

Evan Schneyer 5:35
Yeah. I, I said, how I define success, again, it, Outlaw is an extruded form. For me in terms of being a product product and a problem oriented thing. Dan and I came together several years ago around just this frustration around contracts and wanting to just make the whole experience better for everyone. And so, you know, there's there's several to, you know, initially successes, can we actually build what we, what we're envisioning? Can we get into market? Can we start getting customers at this point? I would say success is actually kind of a boring answer, which is just making a real business like becoming valuable. And it's actually funny, I talk to a ton of VCs, we have a lot of interest. And we haven't raised a series that yet, but we're going to come pretty soon. And we have a lot of inbound interest. And they are they asked, they kind of asked that same question. And VCs tend to one, you know, what, not just what require the word billions to show up somewhere and that answer. And I'm like, yeah, we'll get there. You know, it's a huge, huge market. And we're really well positioned. But right now success is actually you have now that we have real customers that we're serving, they're happy they're growing, we're getting more customers, we have a sales pipeline, that that just kind of boring answer of success being a successful business as an operating at a profit, which is supposed to be the goal of any business, or maybe not a goal, but a fundamental goal. And it's very polarizing. Actually, I'd say most, most VCs are like, we hear about that. It's, it's we, you know, it's growth at all costs.

Andy Halko 7:16
I know, such an interesting market of the the startup community and how they look at profit versus, you know, just scale. Yeah, I'd love you to introduce the business. But one real quickly, you mentioned purpose, use that word of developing purpose. I'm huge about that. I've spent years like trying to think about like, our culture and values, and really putting a lot behind that. So how do you? Or how have you developed like, purpose? And you know, that thing that you get these people rally behind to be excited to grow the company?

Evan Schneyer 7:53
Yeah, I mean, that that evolves over time. I think as our as our market and our customers change, it still starts with the same essence, which again, and it was this just deep frustration with the way contracts work. And I should mention, just real quick, my, my, so I'm a second time. Well, I've got several other businesses, but I'm a second time kind of tech startup, co founder, and my dad is a retired general counsel. Just I've been around contracts a lot in in my career, and even before that, and it's always, as a software developer, as well, it's always struck me that this is the perfect scenario for software to really, really help. And yet, it's not like it's the typical way contracts are done. I guess, I guess I can count Microsoft Word as software. But it's, you know, it's kind of so it's so general purpose. And it's not, it's not built for the type of structure that that contracts demand. And so kind of getting back to your question about purpose. Just that that was the original purpose, and still, still is a big part of the purpose is, as Dan, my cofounder, flexes, say, building the right tool for the job. The job of doing a contract is very structured, there's workflow, there's lots of people involved, there's permissions. There's redlining, there's all these kind of mapped out the whole process. And the tools that people that people use traditionally for that job are just not the right one. So to they're too general. So kind of the original purpose of building the right tool for the job. And again, that kind of evolves Initially, the purpose is just building the actual thing, building the tool, then get it done. The purpose is getting that tool in the hands of people to actually use it and see if we see if we did right now I'd say now that we have what I would characterize as product market fit with kind of a real customer mirbase in the mid market here, which is which is just not huge, not huge businesses necessarily, but businesses have probably 50 to 500 employees and up and and where there's a big team around who need to touch contracts in some way shape or form that. And we've got a bunch of these kind of customers just who have contract process and they've got a sales team of 20 people or whatever it is, and you know, in House Counsel of a few people and C-levels, so a bunch of people who are, who are, who have this, have this problem set and have this need. The pleasure of serving these people and seeing them get value out of it, and paying us for the technology for the software and continuing you know, and then renewing and growing. That's, that is so validating. It's so... it's, it's just a delight, honestly, so and I and then I know you can, you can see just how genuinely I feel that Dan feels the same way. And that kind of I think our whole team, both sales and marketing and product just kind of rebels in that in that purpose together. Yeah, it's awesome. I have to admit, I have a really good friend that owns a law firm, and he never goes anywhere without a file folder, three colored pens, and five different colored highlighters. Yeah, quite literally, you will always see him with that tool set. So it's pretty interesting. Yeah, we have, we have dinner, I think it was our original seed fundraising deck, we had an actual picture of a of, of the results of that process of of a contract, where, where one was actually from a real estate transaction that we had done, where one lawyer had crossed something out and written no other side crossed out the no and wrote No, again,

Andy Halko 12:04
I, you know, contracts that and from the consumer side, for me, not even lawyer contracts are like the thing that I avoid. Like, anytime we have to deal with them as a, you know, an attorney involved or I have to read one over myself, it's like, this is the word of my life that I have to document Exactly. You know, there's actually a kind of part of part of the original product vision. My, again, Dan is a UX designer and visual designer. And so he's done a ton of freelance work. And similar to you, you know, he's used to kind of being the recipient of contracts, and just eyes glaze over. And he's going back to whatever the verbally agreed on rate was, and trying to find it in the fine print. And so one of the very first manifestations of the product vision was actually an overview layer, kind of like a cover sheet, to just basically explain the thing in English, and improve that recipient experience, not to replace the contract, but just kind of package it up nicely. So that the sender can actually know maintain a good relationship with with you. And originally, and that was actually in our, like, the very first version of any version of Outlaw. And we were only very recently and what we found was we it was the right isn't a very valuable feature. And we put that overview layer on our all of our contracts, because we know it actually helps to get a deal done. It helps to keep people alive and make it make sure that no one's trying to get get one by anyone. But it wasn't until actually very recently that we start started seeing requests for that feature. And people were for clients who actually had been using it for a year and a half and heard on a product video or something heard us talking about that and said that would be helpful. And and so we like you know, our CES team is, is you know, funneling those product, those feature requests our way and we're like, yes overviews. someone, someone is using the original essence of why we built this thing.

Andy Halko 14:26

That's, that's very, I was gonna say, can you have a slider bar for me that's like, summarize it at a third grade level, grade level, you know, and then that way down to like, first grade, and it's like, contract good.

Evan Schneyer 14:45
You're going actually even back to like pre alpha prototype level, we had this crazy idea of like, almost like a Google Maps with zoom levels of detail. Whereas like at a high level, here's a one sentence thing of what you have what you're agreeing to. And then you drill in. And then here's the one pager out. Here's the whole. And that was way too much. Way too much work and way too heady. But yeah, the idea is, and that's just that that feature is just, it's optional. At this point, you know, a lot of customers, it's, you know, they have the contract, and they're just like, let's just use this thing, but is still central in that original vision of just end to end, making the whole thing better for everyone from sender to people generating it to people getting internal approvals on a draft to send out, and then especially the recipient, I think that's actually also because of that feature, where we really, it's one of the one of the major differentiators, to some degree, just our user experience overall is really, really seamless. And, and even enjoyable to use, which is not a word that usually is associated with contracts. But it's, it's really essential, and just kind of focusing on the recipient and their experience and considering them kind of a first class citizen with respect to just the overall contract lifecycle is, is not something we see anyone else doing. Because they're not the paying customers, the paying customer at the sender.

Andy Halko 16:18
Right.

Evan Schneyer 16:19
But we can serve our centers better if we help them give that recipients and their counterparties a good experience.

Andy Halko 16:26
Yeah. You've kind of hinted at your origin story a couple of times. Your dad, being General Counsel, you know, some of your past experience this idea of the, you know, your pain with contracts, but can you really talk about like that, you know, period of time of the Epiphany, and you know why you said okay, this is such a pain, and I have this much knowledge. Yes, let's start something.

Evan Schneyer 16:54
Yeah, so the actual idea came several years before starting, starting in the idea. I always had that general sense of like, there's a better way to do this. And every time I did contracts with Wanderfly, my first startup, from 2009, to 2012, I just always had that frustration, but it was so fun. It was a travel, a travel business that was so far from what we were doing wasn't like, I was gonna jump in and try and solve that then. But we were fortunate to find an exit in that first experience, and we were ultimately acquired by TripAdvisor. And that process was just a bigger, more glorified version of the same of the same thing. It was a lot of talking a lot, you kind of get to that verbal agreement stage with more stakeholders, obviously, but you agree on price and agree on just high level terms. And they signed a term sheet. And that's it for first first discussion to sign the term sheet. And the term sheet is in English, the term sheet is kind of like, kind of like that overview layer that I was talking about. And for an acquisition, it's still a couple of pages, but like it's readable, it's it's in English, everyone pretty much gets what's going on. And then going from the term sheet, to the I think the final definitive agreement for the transaction was like 150 pages or something that took another, you know, seven or eight weeks, and was just so frustrated by that experience, that I really felt by the time we signed that I was like, This is the next thing. This is ], this is the next thing I'm going to do. I'm exhausted, so I'm not going to do it right now. I need to I need to kind of maybe take a step out of startup grind for a few years and recoup energy, recoup funds. And that's so I knew I had that idea from exiting my first startup, I'd say to, to start this next one. And then it was a few years later, when I met Dan. And, and like I said, he just... He had us had a lot of similar frustrations just with the process of contracts. And we actually already started working together on just some freelance work and, and projects. So we knew we knew we could work together well. And also designer, he's a designer coder. And so that's a, that's a pretty good pairing for about a cofounding team. So we kind of started kicking around this idea. And we actually went pretty deep in just kind of UX not not like a formal UX research thing. But just we really mapped out the whole process that I was talking about, we thought about how contracts work, from his perspective as a frequent recipient, from mine as a sender or an admin of just various types of deals. And we have a lot of friends and family and in the agency world. So just lots of knowledge about How can a regular business contract cycles work? And we mapped out a whole thing. And had an upstate kind of kind of pre pre founding retreat. It's one of those things where you'd like you can date from lots of different times there's the incorporation date, but there's still like nine months before that, that you were working on it. And then there's like, six months before that, they were thinking about it and talking about it. So nowhere official, sound like, moment of Inception came, but it's somewhere 2015 2016

Andy Halko 20:33
That's awesome. Um, I'm kind of curious real quickly. Uh, you know, we get a number of founders, we've talked to a number of founders, you know, I talked to a number and, and we're really a big part of this audience is startups and people that are looking to potentially start up. So the exit process since you've been through it, you know, everybody looks at it is like this amazing, you know, like, Oh, I'm so you know, that that's the pie in the sky. This is gonna be amazing. I have some friends that have been through it. And I, you know, I've heard the experience. So tell me, what is the, you know, misnomer? What, what, what don't people really understand about that process? Yeah, what's the biggest, you know, thing that the one thing you can take away? That's like, this is not what you think it is.

Evan Schneyer 21:33
Uh, let's see. I mean, one thing that comes to mind is that the, it's a, it's an elaborate transaction, there's, there's, there's lots of different stakeholders in any exit scenario. And we were pretty early, we were at a time of acquisition, I think we were seven. On the employee side, I think we had around 15, total investors, combination of VCs and angels. And then there's the, the stakeholders at the buying company, which in our case, the champion was the head of product, C level C, C suite was involved, there is corporate development, whose job is to kind of get the deal, do the deal and get it done. And then of course, there's teams of lawyers on both sides. So you don't know like, I don't know, 40 plus stakeholders and ask for a small one. So, one, one takeaway is that you've got to be really clear, and, and hopefully get it into the contract of kind of what the plan is, with not just the transaction, but what's the business plan after that, and, you know, and there's, and that, you know, that runs the gamut. Some, you know, there are talent acquisitions, where from, from the start, it's like, we don't care about your brand or product, we just want the team, there's other end of the spectrum, where it's like, this is a, I'd say that maybe YouTube is a great example, where it's like, this is an amazing thing, we just want to own it, but we're gonna build it and grow it and grow everything, keep everything totally intact. And then there's, like, everything in between. And I think it because of the complexity of the transaction, even financials aside, that can change and now with anyone's intention, you know, it can just what one person thinks the plan is, you know, the two people can be aligned at one moment, and then you get to term sheet and then you're way deep into it, and things change and, or, or someone else has more power at a certain point. So it can be can really, really morph without without any malice, or, or anything on either side, it can just change a lot. So I'd say, kind of going back to that purpose thing, to me, this is this is one of those kind of pieces of advice that's impossible to follow, at least certainly on a founder side, it's impossible to follow, it's gonna say, you know, be really clear and, and pointed about that purpose and know why you're selling your company, it's impossible to follow it. Because when the when someone comes knocking on the door and wants to buy your company, you know, the party music, as I like to say, just start to add and like, and it's hard to hear over that sometimes. But, but yeah, like to go back to that know what you're doing now, what you want to what you want to achieve out of it and be really clear and forward about that. And if it's, and hopefully, that's exactly what the buyer wants to know. And even if it is, that might not be where you land in six months post transaction, but at least I'd say you you have better odds.

Andy Halko 24:47
Yeah, yeah. You know, I, I had a client that went through the bio process and one of the big things was, you know, what he wanted to do after and, you know, they want to lock them in for five years. With an urn out, and it's, you know, he wanted less time, so then move on to other things. And then you get, I mean, that even just gets complicated of, you know, what do you want your life to look like after this exit?

Evan Schneyer 25:12
Yeah. So yeah, and also, I think as we again, we're, we're, we're, we're in new territory for me personally, not just on a team size, but just in terms of business viability, we have a real a real business here in the works. And we're also starting and we've we've started, you know, we've some acquired or knocking managed to tamp down the party music to keep keep on course. But it's interesting that the personal trajectories can start to diverge from, from a business trajectory, and that's okay. And actually, I think, savvy, that's something that you VCs have talked to me about, had some really, really positive and really frank conversations with them, especially as series A tends to get big, it's just getting bigger and bigger. And a number of VCs are, are cognizant of that and even advocate for founders taking some, some money off the table, even in an egg. Not not, you know, fuck you money as they, as they say from I think it is it. I'm blanking on the movie that coined that, but...

Andy Halko 26:25
Is it Good Fellas?

Evan Schneyer 26:26
No, it's, I can picture. It's not, it's not gonna not gonna come in. But But you know, something to take some to de risk a little bit to take to have a personal win and, you know, not be hundred percent still tied up in the company. And then others, you know, one of the one of the acquires, who's who, who, one of the inbound acquisition in Greece said kind of spoke to the other end. And they said, like, they they buy companies to grow them. But they have options for founders to just exit, you know, and they said, We know how to go from the stage that you're at, to bigger and to, you know, probably then resell it later for multiple is their goal, but it's totally fine for its founders want to stay on. Awesome. If they want to take something off the table, then that can be worked out. And I think that's a good, it's certainly a good discussion to have, you know, it's really good to it's kind of liberating to be able to think of it that way and not just think, you know, what I want personally, is has to be what outlaw? What is right for our left, and it's as an outlaw, it's kind of I'm not a parent, but I, I have a lot of friends who are parents and it there's a lot of parallels, it's like, as as outlaw becomes viable and becomes its own thing, you know, it doesn't have to be completely joined with what then I want person even what Dan and I want, doesn't have to be hundred percent in line, you know, one can continue on, one could maybe exit at some point. It's, it's a, it's all, it's all negotiable.

Andy Halko 28:16
I have another client friend that talks about like, he's the guy that take it from one to 20 people is not the guy to take it from 20 to anywhere else.

Evan Schneyer 28:27
Yeah.

Andy Halko 28:27
And he realized that in his life, and so when he even like start stuff up, and he gets other people involved or looks at itself, and yet, he says that right up front. He said, I'm not that guy. I'm on this. I'm out. We're taking this forward. Yeah. I think that's pretty cool to have that self awareness and say this is either what I want to be doing, or this is all I'm good at. And you know, we're gonna I'm gonna stick to that.

Evan Schneyer 28:53
Yes. Yeah, absolutely. And it's one of those things that I think a lot of people are, are kind of gun shy about admitting or it's because there's so much pressure to just be like, I'm gonna take it to the moon. And as you start to ask about some of these conversations with VCs are so interesting, as you as you start hinting at that, you get a range of answers, and it actually can really become just an open conversation. And sometimes, I you know, and this kind of goes back to, to the, the essence of our product too just that that idea of just of being really forthright about what you want, with the other side once and seeing if there's actually a deal there. Yeah, it's pretty intriguing. Yeah.

Tony Zayas 29:42
So I've been backing up a little bit, just, you know, you're talking about kind of the start concept and everything. really start to see you know, you found your the example where you went through the process in a number of different ways with the contracts and realize that this was An opportunity. How did you how did you turn that into, you know, a minimum viable product and then go from there? What did that look like in the early stages?

Evan Schneyer 30:12
Well, so Dan and I are constantly juggling. We both love building products so much that by any measure, we like way overshot whoever our market is we way overshot MVP. But we have, I think, a good way that I like to look at that kind of breakdown that answer is what constitutes a big deal. To in whether it's a financially or just kind of in a life in the life of a company, the answer to what's a big deal for us, is dramatically changing and evolving and growing every couple of months, I would say, I think when we when we started, you know, we've had again, you know, starting with two people, we spent like a good year or so just hacking on it ourselves and prototyping and put it in the hands of friends, and had a lot of of Freelancer friends and kind of very small business scenarios. And so he still had some is still was a big deal. In those stages, it's a big deal to like, have a product at all to be used to use, it's a big deal to use it ourselves for our first couple of contracts. And it's a big deal to have, you know, when you're really starting from nothing to help Ted anyone using using what you've made successfully and paying you for it is a big deal. Even if they're only paying you 20 I think our first price was like 20 bucks a month for like, you know, very, very for for single users or for very tiny businesses. But we very quickly discovered that, that the real I mean, there's still there's still a bunch of, there's still an opportunity space for that market. But I think we were we were gravitating towards much bigger companies, who just who, and it's a bit of a different problem, because the really, really small companies didn't even have contracts that their problem is more like this. For one, they're not usually the sender, they're usually the recipient. And if they are the sender, it's like, you know, once every two months, that they happen to be in control of sending us a service contract to a to a new customer. But most of the time, it's it's enough out there that someone someone sends them a DocuSign link, and they just sign it and cross the fingers. And so we couldn't even really solve that problem for them. So we started going up market. And I think as as the as, as we progressed up market serving bigger customers, that the quest the answer to what is a big deal for us. changed dramatically by orders of magnitude, you know, initially it was, it was oh, my God, someone's going to pay someone signed on for a year to pay 300. You know, is it fair to pay $240 for this thing themselves to us. And then, you know, a few months later was like, it was 10 times that. And then a few more times, more months later, it was 10 times that, you know, now now we're getting now I think we found our real sweet spot now, which actually was the vision that we that we pitched and talked about in our seed round with our lead investor, which was mid market, which which we kind of an even that can be a moving target. But we said there's so many businesses out there who are in that skinny, who in that kind of just not huge companies, but but solid, real companies range, tell it like 10 to 50 million in net annual revenue 50 to 500 employees, they just have their act together. And they use contracts every day. And there's so many businesses like that, and being able to and so and they will and for them paying an annual rate of 10 to 25,000. For just a system that meets their needs is easily any way you slice it, whether it's about cost savings or improving deal flow and upside, this so easily or just about being a repository for further 2000 contracts that they've signed already, over the last 20 years of doing business. Any way you slice it, it's easily justifiable. And there's so many of those businesses out there. There's so many there's a huge addressable market of that of that segment. And so now, it's no longer it's no longer a big deal. When we get a win win, we win that lead or an outbound lead to one of those businesses who said yeah, we need we've got 1520 users and we're looking in the next 15 k annual or something so cool. Added to that. pipeline. Now it's now it's though the order of the next order of magnitude, you know, the 50K, annual deals of getting edging into enterprise. That's a big deal. So I think, sorry, this is a long winded answer, but like it, you know, changes through the years. And, and it's, it's good we do we try to make a practice of taking snapshots of that kind of asking ourselves every couple of months, kind of what gets me excited, what's a big deal? And it's not always about a sale or a customer purchase, like, what is a big event? From our, from our perspective as founders, and it's cool to see the answer, the answer to that getting bigger and bigger.

Andy Halko 35:41
Yeah, it's a fun evolution. This is kind of just, you know, randomly on my mind, we're working with a software now. And, you know, one of the things that I I see, and I'm curious from your perspective, because I think your industry's got to have some decent competitors, you know, and even some, the homeless in the marketplace, you know, and I know what these guys we've been kind of talking about, like, okay, we keep finding some more competitors out there, and some that are pretty well established. Others that, you know, could easily take their software's functionality to add it into what they're doing and quickly evolve, because they've already got thousands of clients. You know, how do you handle that? And I'm asking this more for like, an almost emotional rather than tactical standpoint, up that you've got to hit these like barriers, or these air these places where it's like, well, am I really going in the right direction? Or, you know, is this harder than I think it is? How do you as a founder, I don't go through those cycles and keep yourself motivated. And, you know, get past some of those things that are like scary in some ways.

Evan Schneyer 36:58
It sounds like you're kind of saying, how do we think about the competition?

Andy Halko 37:03
Yeah, I mean, that's the kind of the basis of it.

Evan Schneyer 37:06
Yeah, I think, Dan and I, we now we have we have a great marketing and sales, great marketing team and a great sales team and and customer success team at this point who all did there, they kind of funnel the information about, you know, what, how are others, describing themselves, making sure that we're kind of competitive in those regards. But at a kind of gut level, I would actually say, I don't really think about the competition. The customer, I think about the prospects we're talking about, and whether we are whether we are going back to that purpose, that kind of product driven purpose, whether we're meeting the needs lots of people, whether it's inbound or outbound, who are pretty self aware and sophisticated about their needs, because again, these are real businesses now. And they've got they've got, you know, legal operations people and in House counsel and, and VPS of ops and modern sales and stuff, who, whose jobs rely on on these processes. And so they'll come to us and say, We need something that does this, this, this, this, this and this, and then we kind of turn around say, well, we do those, we do all those things. And yeah, a couple of things, we do a different way. I say, well, we're we're comparing you guys to these others. And so we you know, that then the competition gets in, but it's, it's a very, it's just a very problem solution. mindset. And I always kind of say, our, my, my mantra is to follow what works, you know, when you, when you see that someone comes in the door and says, I need this, you tell them that, and then they're happy. And then they ask for something else, or you get three more requests for, you know, an adjacent feature that would solve a different a different flow or different use cases, we say, well, there were, you know, we're 100% on these guys, but we missed the mark. We didn't we weren't able to fully cater to the to this other one or to these prospects, or we're losing deals, because we don't have this thing that someone else has. So let's build that thing. Again, it's very, because we're so product centric, and myself and Dan, it's, it's not just easy, but it's actually fun to, to you know, check those boxes. Yeah. That's cool. Yeah. And then and then the, as far as the competition goes, because I think we're, we're so because it's so product forward, and we're so hell bent on really solving this problem fully for customers. And that shows in our reviews, and so we actually have a lot of really, really, incredibly happy customers, which gives us great, great rankings on the software review sites. Which is where our best prospects are coming from and comparing us to the competition. So again, kind of goes back to purpose, and just really being dead set on solving that problem. But also having the humility to when you get it wrong in a certain way, and going back to that old saying, you know, we in our first in our early in our early, I don't know how long, maybe a year, year and a half, we were very, at least in an eye, and then as we kind of had had sales team doing pitches and demos. We were very bullish on that overview feature. And then we kind of realized, this is what even though we think this is valuable, it's confusing people, they're so used to just seeing the contract. Forget, like, just because we built it doesn't mean it is the right thing to showcase. Certainly not in the first conversation. It's like, it's just too confusing. So make it make it optional and take it out of it. Don't Don't even mention it until a year later, when someone is already using using the rest of it successfully and said, Hey, what about that overview thing? So it says it is a constant? I think I briefly referred back to just having no ego about it. Dan, I are adamant adamant about that, both just personally between the two of us. And I think we kind of like really, I don't even want to say enforced, but just kind of influenced the team about that, that like, gotta you got to take feedback. You can't, you can't be you can't learn. If you think you're always right. I've seen a lot of startups fail because of that, you know, the founder is that ego and they don't want to change and aren't willing to be wrong. You know, instead, they go into the marketplace with a strong idea and try and force their clients. Yeah. to their idea, rather than shaping to what their client's needs are. Yeah, no recipe for failure. Right? Exactly. But But you have to have those experiences in order to in order to improve, but you have to learn from them. I constantly at this point, it's that's that mentality is really baked into our certainly our product development process. And our roadmap is just entirely customer driven at this point. Just people asking for things and seeing patterns and what they need. And then and then kind of putting in front of them and saying, is this? Is this what you meant? No. Okay, let us let us tweak it a little further is this, which meant Oh, good. But even on the sales front, we just had a new a new account exact start. And she was a little bummed about, you know, her adept, one of the early demos not not going totally smoothly. And I said, Look, you have to have that in order to learn, like, you know, as long as you as long as you acknowledge it, figure out what were what could have been better and learn. Learn for the next one. That's a win. You know, that's, that's how you improve. You have to you have to Yeah, acting perfection out of right out of the gate, you know?

Andy Halko 43:20
Yeah, I really love the customer driven roadmap, you know, and having that mindset for sure.

Evan Schneyer 43:27
That's a that's a challenging one. It's a balance, because... Well, it's I mean, I do and I know Steve Jobs is, you know, the famous other like polar opposite, like, like, the customer doesn't know what they want, because they can't, there. There certainly are into that where it's like, they're because they're kind of in their, in their so in so much in their world, they won't even think to ask for a solution that actually would dramatically move the needle. But it seems and so there's, there's there's some of that in terms of just the way that we approach the whole problem. But at the same time, needing to we actually, it's really interesting how we built kind of the order of things that we built, because again, we weigh overshot, minimum viable, and built this really advanced, kind of fully proprietary contract system. And that was much harder to and much more work and not exactly customer driven, initially in terms of the core, the core of the technology, but then as we started interacting with customers, we found we really need to build that bridge so that wherever they are today, they can get quick wins and say, you know, I'm looking for some, you know, I need to move, move these documents from here to here with these people's approvals. And we can say, Yes, we can do that for you, by the way. Yeah, start doing it, start doing that. But by the way, there's this other thing here, like you might want to check out at some point Yeah, and then a year, they're completely off to that process and everything is automated and magic. But it there, it has to kind of have to hold their hand through.

Andy Halko 45:10
Yeah. It's like a, you know, ford. Some, you know, they when asked people they would have said they wanted faster horses, you know, and Exactly. But it's this mix, you know, you'd look at Steve Jobs, same thing. I mean, they talked about how the Palm Pilot had been around, you know, and didn't adapt. And then, you know, you had an iPod? And so it's this interesting idea of the of these visionaries that have innovative ideas and can, you know, think outside the current market, but then balancing that with the folks that are in the market and have very tangible needs at this moment? And how do you find that connection between those two things? And then keep evolving on it?

Evan Schneyer 45:54
Yeah, yeah. Yeah, there's, there's a number, there's a number of at this point, we're now about, and we just very recently, like the last couple of weeks, hit a hit a major product milestone where Dan and I realized we're actually from a core perspective, like the core elements of a contract Lifecycle Management System, we check all the boxes were feature complete. From a, from a core, there's still a million, you know, the twos and the threes have certain features and ways to tie things together. So there's, there's still no and no end in sight for product development, which makes us happy. But, but from a core perspective, it's, it's, it's all there. And so now we can have our whole our whole roadmap pretty much be the customer driven.

Tony Zayas 46:45
Pretty cool. So Evan, obviously, you guys are on an, you know, great upward trajectory team is growing, what would you say you look for, as far as when you bringing new people in new talent, what are the traits that you're looking for, that are most important to you.

Evan Schneyer 47:07
I mean, that kind of, it kind of varies a little depending on skill set and an area. But I would, I would say without exception, we need to, we just need to be good, decent people. So that's usually the culture, the culture fit piece, and I've done some writing on our blog of just our company culture. And, and like I said, you know, half an hour ago, we just, it's, it's still we're still at a stage, we're still pretty early stage, and everyone knows each other and really, really invested. And, and it doesn't work to have people who don't, who don't want to work together. You know, and so that, I think I I guess I would say high high EQ, is is a big proponent of that, you know, not not having any not having any ego, obviously, there, you know, there are days there there little, you know, frictions between people here and there, but, and we're hitting a certain size now, where not everyone can know and be close to everyone else, especially now it's, you know, full remote. And actually, we're kind of gradually going back into the office, but predominantly remote. For a couple months in there, there were people who, we had never even met new hires that we were working with for a couple months that we had never met. But yeah, I think that just genuine decency. And, and kind of being in it for the right reasons, being in it to to be part of something and to create, to really create value. And I guess more if you're on the sales side, more more deliver, deliver and kind of exchange value with customers, but but not in it. And we kind of referred briefly back to some of the startup culture stuff, you know, not in it to just to to have a big team under you, not in it for the amount of money that a VC money that you can raise or for the for just not in it for the ego reasons, basically. Yeah, and there's, I kind of look at it as there's like, the qualifications for the job, whatever the job is, and then there's the kind of the attitude and we all have as as hiring as founders and people who are hiring people, you know, you want both of those to be excellent. We want to have the best people with the best attitude, but on but on startup compensation packages, which is obviously you know, there's like constraints there. But given its Shall we do have, you know quite a few people who, who are that, you know, but it's when when you can't, when you're operating within constraints, I found an official, an official addition to the, to the interview, she's been here this whole time. With constraints, it's kind of you're frequently faced with like, kind of one, one or the other, where you have someone who's who's great at the job, doesn't entirely have the right attitude, or has a great attitude isn't entirely, you know, the best person for the job yet, I would, hundred percent of the time, choose the latter. And say it, the attitude just matters more. Because the skills are the skills are learnable the skills are are someone who's got the drive and the and is able to work together well and is in it and is here for the right reasons. They can be flexible, they can move roles, they can acquire skills, they can take feedback. That's much easier said than done. It's really easy. But it's that's that's a better, a better fit for us.

Andy Halko 51:19
It's interesting, you mentioned EQ, I, you know, I talk actually a lot about EQ, IQ. And, you know, where do you rank people on kind of that spectrum. But I had this interesting theory that I work with, with a buddy of mine that owns a company on where, you know, this idea that, you know, if you have a high EQ, you really have to be a founder of a business that you have passion around the industry and product. And you know, as you go towards IQ, it's okay to move away from that. And the reason we talked about it was, you know, we do find some founders that are in businesses where they solve the problem, but they don't really care that much about the industry. And there's a period where if you're a high EQ person, that it's hard to scale that company, because you don't have the passion, and you're more of an EQ. But you know, you can scale an idea you don't like as much if you're more on the IQ side. And so we were just kind of saying like, as SaaS founders, it's one of those things that if you understand where you're on that scale EQ IQ, it'll also help you be successful, if you make sure that you're, you know, on the EQ side and more matching your startup to something that you can have a lot of passion around. And so I don't know, just kind of more of a statement that you since you mentioned, EQ.

Evan Schneyer 52:43
I think I would say just having having the having high EQ is essential to opening up more options, because then you can actually for one, know, know what you actually want. And then hopefully communicate it openly. And then talk about it and say, you know, maybe what, maybe, maybe the founder does want to continue on and grow it to 1000 employees or whatever. But I think I think a pretty common sort of, kind of component of burnout, especially for the stage we're at, or maybe one or two stages be before and after where we're at. It's like, there's this poll to kind of be to be someone you're not or to, or to even just spend, spend your time spend your days doing, doing stuff that you don't want to do, or they just not great at. And if you and if you don't have that self awareness, and I know plenty of other founders, who like a few years in, they're like, I'm, I'm super busy, even if my, even if my business is going well. I'm just stressed out all the time, I'm doing stuff that I'm I'm not passionate about. And I just and they feel really like stuck. And if you're able to say, I mean, I just have to give a kind of funny example. I personally spend way more time coding still now than any other technical founder. I know most of them and sometimes that's fine some some don't want to do it some summer are thrilled to kind of be on the business side. For me, I'm like I just it's not just that I love doing it, it's i'm i'm most valuable there and I can do the business stuff but I can also hire hire people we six months ago or so we recruited a head of sales. And that's been amazing, you know, usually usually the kind of CEO at this stage kind of kind of functions as head of sales and and the constant constant. Not even debate, just discussion with our investor who's like who's like yeah, you guys. You guys are so good on product. Keep doing But you need someone to kind of run the business side. And I was like, yeah, again, my ego is not wrapped up in it, I don't need to be, I don't need to be the one closing. I'm available, like anytime I'm anytime it'll help to, for me to join a join a pitch or join a call. Absolutely. But But you need to be able to know what your know what you're good at what you're not so good at, and what's your kind of, I guess strengths and weaknesses are and also how those things are changing. And I think if you but you that self awareness and communication are essential to to do that and not get kind of not find yourself in that bind, where you're kind of doing something you didn't sign up for?

Andy Halko 55:50
Yeah, I always over the years have really thought that the best folks that I've worked with have great self awareness. You know, they know what they're good at, they know what they're not. And they're a you know, they're able to be confident what they are good at, and comfortable with the fact that that's what it is. And they're also confident and comfortable with the things either they don't like or they, you know, aren't good at it, and they're willing to fill those gaps. And you're one of those people that doesn't have that self awareness, it's really hard to work with those. It just is, you know, because, yeah, they don't realize what they're not good at, or, you know, they get angry because they're working on things that they don't want to be and they just don't have that self awareness around. And they're really hard to work with. So yeah, yeah.

Evan Schneyer 56:36
You know, founders and non founders alike.

Andy Halko 56:39
I agree. Yeah. So we're kind of coming up on, you know, an hour. I mean, I just be curious, you know, what's Is there any kind of summary like, you know, if you were to talk to yourself 10 years ago, one piece of advice for for you have, like, you know, or something that you've learned, that's just been really impact?

Evan Schneyer 57:03
Yeah, well, I kind of, I kind of did that, actually. Because this is my second, my second startup. And actually, somewhere in those early years, I put together a spreadsheet, and I'm a big fan of point systems, I have a whole bunch of things, things that went really well, such as the team and things like that, and the product vision about our first startup and things that I really proactively wanted to change. And the biggest one, as we were in consumer travel in the in the first one, and that is well, especially now, but even before even before COVID, consumer travel is a challenging space, because basically, you're building software, and then giving it away for free. And so I think probably the top, the top thing that I said I want to I want to do this differently, is I know that whatever, whatever I build, I'm going to be 100% focused and just thinking about all the time and put putting everything I've got into it. And so if I'm going to do that, and my co founder is going to do that, let's just sell the software, if we're going to put, you know, treat this amazing product, it's much more direct, to build great software and sell than it is to build great software and get tons of people to use it for free so that this other group can advertise to them or so that more can exist. So if you like map out the value exchange and the business model, I was just like, now I want to build great software and sell it directly can have a direct relationship with my customers, so that when it's not doing everything they want, they tell me what's wrong. It's much more it's much more simple. Yeah. That's great. Anyway, back to that original kind of purpose of end goal that we were talking about, you know, which is why it's kind of boring from a business perspective. But yeah, our goal is just to we have we make product and we're selling the product, we want to sell more of the product to get to the point where where our business is viable.

I if it's gets boring, you want to solve a problem and do it really well. You know, I mean, that's what great founders are problem solvers. So yeah, nothing boring about that. Tony, anything else you have you want to add in or?

Tony Zayas 59:27
No, I'm good. I just want to thank Evan for his time. This was fantastic. We appreciate you spending, you know, the full hour here with us and a lot of good stuff. So we will certainly pay attention to Outlaw so I encourage everybody who's watching to go check out Evan's site, etoutlaw.com and, Adam, thanks again for joining.

Evan Schneyer 59:48
Thank you so much. My pleasure.

Andy Halko 59:50
Thanks so much, Evan. We'll talk to you soon. Take care. Bye bye



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