248: Ruben Gamez — Cracking the E-Signature Market

Download MP3

Arvid Kahl 0:00
Welcome to The Bootstrapped Founder. Today, I'm chatting with Ruben Gamez. He's a longtime indie hacker, a SaaS experts and then all round treasure trove, both of knowledge and community support. He is wonderful. Ruben shares with me his approach to alternating between low touch and high touch during many processes, particularly the signup process for a software product, then also what he thinks about the whole call to cancel thing and how he deals with much bigger competitors in his E signature business. We chat about customer segmentation, if freemium is a good idea and we'll even get into book recommendations today. A quick shout out to the sponsor of this episode, acquire.com. More about that later. And now, here's Ruben.

Ruben, thanks so much for being on the show today. I recently talked to Brian Sierakowski on this show. And he was the unfortunate target of a lot of Twitter hate back then a couple of years ago must be 2020, when he implemented call to cancel at Baremetrics. It was a big day in the indie hacker community. Man, that was rough. And the indie hacker community really didn't like it. Right? It was just there was so much going on there. A few weeks ago, I saw you tweeting something, not necessarily the same. But along the similar lines where you said you occasionally changed your signup, which is obviously not canceled, but sign up from low touch to high touch occasionally, every now and then, which I find is a similar move. And I was wondering, this was very intriguing and unexpected because I've never seen this done before. Can you explain the why and the how behind this particular approach?

Ruben Gamez 1:38
Sure. So we do this to get feedback, really good feedback and to learn things. It's basically just data and learning. So we understand that when we do this, when we change it right now, just to give a little context. People sign up using a like, sign up with Google button or they you know, click on the link and they enter their username and password. It's really easy. They're in. There's no email verification or anything like that. You can get started. You can upload a document and then send it out to get signed. So it's maybe a little bit not enough friction as far as we don't like even ask who you are, what's your use cases, you know, that stuff. But there are times where depending on the metric and the thing that we're trying to move or improve in the business, we try to get data through, you know, analytics, through support wherever we can get the data. And then there's just times where we just don't have enough data or we don't understand a problem enough to help move a metric. Let's say it's related to onboarding or activation or some other use case. What we'll do is we'll change the signup. And when somebody you know, we'll change it to a button and they'll say, like, sign up for free, they click on the button. And instead of a signup form or you know, the Google login thing, they'll go to a survey. So the survey asks them questions about what type of business there. Like some of the initial questions that we're trying to segment by or understand. And then we'll ask them, like, let's say we're trying to target teams. We want to learn more about teams in the onboarding process. So we'll ask them how many people are going to use this. And if they say, just me, then we'll redirect them to the self sign up and they'll just self sign up. So then we only do this for the people that we want to learn from. And if it's a team, then we'll direct them to a basically a page to where they can schedule their onboarding call to get set up and sign up. So we understand that we'll lose signups. This is a temporary thing. But the way that I think about it is that it's okay because we're paying for data, like the cost the price there is us learning. That's how we're going to learn.

Arvid Kahl 4:13
That's some interesting approach that the segmentation makes a lot of sense. I think that very much shifted in similarity to the full call to cancel thing because, you know, if Brian had kind of segmented call to cancel by the account type that was canceling, that would have been interesting too.

Ruben Gamez 4:29
That probably would have been right. It needed special sort of, like attention or time or whatever.

Arvid Kahl 4:34

Ruben Gamez 4:35
Yeah, that could have been one approach. I mean, I'm okay with just saying everyone like if we needed to, I don't know that we've ever done that. But if for some reason if I felt like we needed to, I'm okay with doing that for we get such a large number of people signing up, the 20,000 signups a month. And so it doesn't really take that much. Before we're like, okay, we're good. We have enough people that say nothing, we're gonna learn what we need to learn from the, you know, in a few hours or whatever or a couple of days before segmenting, it will be longer.

Arvid Kahl 5:13
Yeah, that's the thing. I was wondering about like, how long do you keep this going? For how long would you do such an experiment? Does it depend on the actual outcome of the calls that you have? Or would you just set like a set timeframe for this?

Ruben Gamez 5:25
It really depends on how many people are going through that. So I think the last time that we did it, we were wanting to learn more from people that signed up from a specific traffic source. So we did interviews with them, different types of interviews, but then we also wanted to learn more about them in the onboarding process. So I think that one ran for like a week or somewhere around there just because there was lower volume and we don't get that much from that traffic source. And then you know, just people will, they're gonna be, depending on who you're targeting. If it's team, teams are more likely to schedule. If it's a traffic source to where it's just like, a lot of, oh, it's just an account for myself. I like to do things myself, then you know a lot of those people are just gonna look at that and be like, what is this? I'm not gonna schedule that.

Arvid Kahl 6:22
Yeah, it's kind of like a cold email, but in the form of a form on the website

Ruben Gamez 6:29
Yeah, a little bit. And there's that selects for a certain type of user, right? So we understand that, like, you know, the learning there. It's just a data point and kind of understand, how is that different from the typical user that signs up self serve?

Arvid Kahl 6:48
It's very interesting. I never thought about this. I never thought about optimizing the process itself. Like I was always thinking that I could figure it out somewhere else. And then I would change the process accordingly, but changing the process to figure out, to optimize, that's just a new way of thinking about it. And I was wondering, as an indie hacker that I consider myself as and that most people listening to this probably are more like, when do you start with this? Because this feels like you kind of cut into your revenue a little bit potentially. So do you need to have a certain size or like a certain MRR to start with this? How would you consider or when did you start doing these experiments?

Ruben Gamez 7:27
From the earliest days, I started from the very beginning, even the landing page before we launched, right? Like you put up a landing page and you have an email, like, you know, enter your email to be notified. They put in their email, they submitted the form and that went to a survey. And then we asked more about them, their needs, why they were interested, you know, just to get a little bit of, because they're the most engaged at that moment. Right? It's harder when somebody signs up to send an email and you'll get some answers and replies to those. But they'll be a little light different a lot of times and sometimes you'll get good conversations. And then we asked, would they be willing to jump on a call with us to like, you know, help us with some of the research on this? And a lot of people said no, some people said yes. And then we added them to the early access list. But yeah, so before even launching basically is the answer. And then a little bit, you know, after early on, especially early on. You know the least about your customers, about the use cases, about all this stuff. So it's tricky because you're right. Revenue is a concern, right? So that's a tough thing to balance it like the more you need the money, the more selective you have to think about that. The reality in SaaS at least is that very early on, for most of us, we're just not going to make that much money in the like, the first few weeks or whatever, right? So you have to weigh that against, like how many people are certain, like some people are launching and they're just getting very few people signing up to start with and I understand the fear of like, well, putting this amount of friction up front. They're not even like even the very few are not even going to be able to get into the product and experience it and have a chance to upgrade. I think indie hackers shoot themselves in the foot sometimes with some of these fears like that. Because what tends to happen is let's say they get five signups a week or something like that, like a lower number. So they value each one of these but maybe the traffic sources aren't that good and maybe the you know, the signups aren't of the highest quality. Some of them are, some of them are not. It's always a mix. And what happens is that people go in there and they kind of it's almost like, they remove all friction. They try to let them sign up really easily and use the product and hope they upgrade, but they're not learning anything in the process. What they learn is like, oh, almost nobody upgrades or very few people upgrade. Why is that? I don't know, it's super fuzzy, like, all these fuzzy areas are a big deal. And they're really important to learn as, like as quickly as possible. And it's not a thing of like, well, let's go a few months, let's add more like, yeah, but how much stuff do you not know? And if you knew some of those things, how much faster could you grow or add the right features that will help you grow? You know, there is a balance there. But I would probably encourage people to lean towards the direction that's a little bit more uncomfortable with some of this stuff for them.

Arvid Kahl 11:11
Now that you say this, I mean, it makes perfect sense. Like you learn as much as you can, as early as you can. That seems to be a very quick and tight feedback cycle indie hacker thinking. We should probably do much of that much more of that than we're doing right now. But does this also hold for exit interviews? Would call to cancel actually makes sense in this kind of line of thinking. But do you utilize it? Did you ever utilize it in any of your products?

Ruben Gamez 11:39
No, the closest that I've that I would. I wouldn't be opposed to it if we were just not learning what we needed to. So we never got to that stage. We've done so much stuff to try to learn from people that cancel. And it's tricky because by the time they cancel, they don't really care a lot of the time and they're not like just you know, going to answer your questions and they're done. They're moved on to their thing. Everyone's busy. It's not like, personal, it's just, you know, we're all busy and everyone's calling for our attention. And, you know, we have to protect our energy and our time, right? So, yeah, what we did everything from, you know, the cancel. We email them, you know, automated. We email them, manually. We search into them, let them know that it's, you know, the founder, all this stuff that when they cancel, we send them to a cancel survey and you know, they answer questions and some of that stuff is like, ah used to be familiar with this stuff, like not using why not? Like you know, a lot of times they'll describe symptoms and not the core issues. And then the most useful thing is just cancellation interviews. And that's like in the cancel flow of offering an incentive to do a 30 minute call with us. And then do the jobs to be done like a switch style interview tour. We asked them not why you canceled but what happened not like, what happened? Why did you cancel? More like, when did you first start thinking, like, oh, maybe I don't need this anymore? What happened that day? Do you remember the day like you basically walk through the actual events? And from that, you paint the picture. And then you don't have to ask why it's clear why? What happened? So that's been the most useful. And that's as deep as we've gotten as far as trying to get, you know, information from people that canceled

Arvid Kahl 11:39
The jobs to be done, approach is really powerful, right? Because you see the underlying reasons not just the whatever in the moment happened that made them cancel, but you see what led to that moment. Which makes me wonder, do you ever ask what you could have done to make them stay? It's got the kind of feels like asking people if they want faster horses, you know that thing. But what do you think about that kind of line of questioning? Do you use that in your customized

Ruben Gamez 14:12
No, because once you walk through what happened, then it's really clear what you could have done to them and why they canceled. The reality is in SaaS, a lot of the people that cancel, they canceled long before they actually cancelled. Like they just haven't gotten around to canceling. And then like they'll get an invoice or something like that. That reminds them and then they'll count like we've all kind of probably have done that and we can think of like things that we're like, oh, yeah, like I haven't gotten around to cancel that yet. You know? And a lot of times, it depends on the product, of course. But it's surprising how many times the core reason really has to do with what happened upfront. Like, not so much. They're using it and then something happened and they're not happy. And then they canceled. That happens, of course. But it's really like either they never truly started using it. Or they're like half using it and not completely in the way they intend, you know. And that's why a lot of times time spent on activation onboarding can help retention. That's a really big lever there.

Arvid Kahl 15:28
Yeah, it sounds like you want to onboard the right people and not onboard the wrong people. Just give people this opportunity to understand that either this tool is for them and they'll use it or is this not and they don't even get to not use it and then cancel. Am I getting this right?

Ruben Gamez 15:44
Partly, like, there's definitely that part of it, for sure. But there's also if a lot of people that are the right users or could be the right users, but they didn't use it because you know, something was confusing or complicated or they didn't think they could do something like typical onboarding and activation sort of issues and problems that can be fixed and improved. So there's definitely a lot of room there for improvement for most SaaS products.

Arvid Kahl 16:15
How actionable are these interviews for you when you do them? Like how quickly do you turn those learnings into a change in the product?

Ruben Gamez 16:25
Super actionable, we document all that stuff. And the way that we do it is I'll right. So I've done that a few ways. And I'll talk about it like in terms of like if I was a solo founder, almost like the you know or very small team. And our team is pretty small as it is to begin with. But what I like to do is do these interviews, record the audio, take notes in Google Docs or whatever. And then I'll listen to the audio at a separate time, like the next week or something like that or the next day and I'll go through and I'll you know, with fresh ear or whatever you call it, I'll document stuff. And notice things that maybe I missed. And then put my takeaways, organize that base of like, okay, this is actionable stuff that we could do based off this one interview. And what I like to do is I like to give that same audio recording to somebody else and have them you know, do the same thing separately, us not talk about it. So then I want to see what their takeaways is. Because compare them to mine because I have certain biases and especially if when we're trying to improve like a thing or metric or something like that. We have these ideas of like, oh, we think it's this or you know, like a direction that really can influence what we take away, like there's the data and the information. But we're still translating that into actionable stuff. And our bias definitely comes into effect. So it's really interesting to see take somebody who doesn't have that bias and see what their takeaways are and then compare them to ours and see if we're like missing something. Oh, okay, you know, there's something over there that I probably should look at. And the way that I've done it, is somebody else on the team or I've done an even tour. I've hired or have had a writer that was doing just like content for us, you know? And asked him, hey, I'm doing this special project. Would you be up for it? So it's not even somebody on the team, like, you know, its core team is just like a contractor that's helping us out with some other stuff. And if they're, you know, there's usually writers, copywriters and all that are good about, like, the good ones, paying attention to the information and then like writing down takeaways and having, you know, asking them to do that and then seeing what their report looks like compared to us just giving them something to write.

Arvid Kahl 19:12
Interesting! That actually sounds and feels like a product that should actually exist outside of just your organization. Right? Like bias free summaries, I was thinking as you were saying it like you want to externalize it more and more away from the bias, the inherent bias in your team. Have you ever used like AI tools for this like a ChatGPT, which is summarize it upfront.

Ruben Gamez 19:32
No, I have not. That would be a really interesting use for it. Right? That's a good that's even maybe a better way. Right, definitely cheaper. So now you could do that. I'd still probably I do like, I'd probably do three. I'd probably do AI and then have somebody else do it as well. And then me, you know, because sometimes I think that people would, you know pick up some things as well.

Arvid Kahl 19:58
They would be very interesting to see the differences. I think there's rarely a better way to see just how inherent your bias is and how maybe even you already kind of transported it on to the people that work for you. And then how there's a completely neutral thing that looks at it. So, yeah, that'd be really cool. Wow. That's a very interesting approach to dealing with. It's a very elaborate or involved. I don't know which one of those two words I would use but a very, you take it very seriously, that's really cool to hear just how valuable this information is to you.

Ruben Gamez 20:29
Yeah, I mean, you asked like, how actionable and how quickly do we put into, like, as quickly as the next day we start doing stuff, if there's stuff that's easy for us to do. And then some stuff is like, a year later, we're still referencing, like, we have these interviews from this, you know, segment here, like, oh, it could be useful. Let's see, let's refresh our memory and see what's there. So we always come back to it. And it's just like an evergreen sort of resource. And sometimes it needs to be refreshed if it's been that long and the product has changed a lot, you know, depends.

Arvid Kahl 21:05
That's very cool. Do you do these kinds of interviews at other stages of the customer journey too? Like, just post onboarding or in the middle of people using it for a couple of months?

Ruben Gamez 21:14
Yeah, so mainly, like the switch style ones like onboarding and cancellations what we've done a ton of those. And then sometimes we are, you know, trying to learn something about a specific feature or whatever. And we do those and try to follow the same structure. I'd say that a little bit more like the Mom Test sort of approach there when we're doing it based off of like, in the middle of, let's say, one of the ones that we added recently was bulk sending, so the ability for people to upload a CSV file. We want signatures of 300 people for this one template. So some people would do that manually, before we had books ending and then we added that feature, but to learn how to create a good box editing feature we did that. We're like, okay, let's talk to the people who are doing this process. And we interviewed them like, what are the steps? Who are you sending this to? Why are you doing this? And then walk us through it. And what do you do after? Like the after, I think is missed a lot and and super underrated and/or before. Like the stuff around the edges? And why are you doing these things? Like you can make your features much better based off with that information.

Arvid Kahl 22:36
Yeah, workflow is so important, right? Like a job to be done never stands alone. It's always integrated into some kind of series of other things. To me, it's like, well, if you're a software developer, you innately understand this if you deal with data. Data comes in one format. You do something with it. And people use that what you do. They expect it in another format or maybe the same, just with different data. So you have an input format and an output format. I think the same thing should always happen with any job to be done, like, what data comes in? Or what requirements come in? And what requirements are expected on the outside too. It's really cool to see you thinking about this, like before and after stuff as well.

Ruben Gamez 23:12
Yeah, and same thing with triggers, right? Like triggers are really important thing. Like what triggered this whole thing is to start with, like, that's an important thing to know and keep in mind.

Arvid Kahl 23:21
That's pretty cool. Do you use the same playbook for both of your SaaS businesses? Do you do the exact same things? Or is it different between Bidsketch and SignWell?

Ruben Gamez 23:31
We do a lot of the same things, some things differently, but they're very different businesses. Even though like from a high level, I thought they were the same thing. It's just

Arvid Kahl 23:41
Yeah, let's talk about that too.

Ruben Gamez 23:43
Like, that's a really easy trap to get into. It's like, yeah, it's basically the same thing. Like you have a document and you're sending it out and somebody looks at it and then they just approve or sign or whatever. And that's it. They both work exactly the same way. And these businesses could not be like any more different.

Arvid Kahl 24:03
I do want to talk about this, like with Sign Well and where it came from because from what I understand, this wasn't even meant to be a second business. Is that right?

Ruben Gamez 24:12
Right. Yeah, yeah, it was supposed to be the next version of Bidsketch and Bidsketch is a proposal software. And, like, take everything that we learned, redesign it, improve it, add document signing, which already existed in it, but a very simple form and just say, let's open up the market and then we'll have the whole document signing market as well and support more of our customers document workflows. And then let's start with the document signing and make that a different brand and build that and then we'll have two sites. We can funnel in and we'll merge them and you know, this is all big plan. And then we did document signing and came out with that and like the users are different. They're asking for different things. They were pulling us into different direction and then it was just that decision time. I'm like, do I continue with the vision that I had? Like, which is different than what the pull that I'm getting here? Or do we go in this direction? Went in that direction and then, yeah, so I ended up with two businesses instead of one.

Arvid Kahl 25:18
I'm still thinking it's really cool to just stumble into a successful business, but I don't think there's much stumbling, it's just, you know, it was there. And you opened that door to that particular area.

Ruben Gamez 25:31
With Bidsketch, we never promoted it to Bidsketch customers or leads or traffic sources or anything like that. So it was literally building it from zero and building the hole. And I did that on purpose, because I wanted to have to, you know, like I said, it would be almost like two traffic sources and channels and everything just merged into one. But I never, you know, it just never became that thing. And so it was just a separate business built from scratch and having to have that whole momentum stage built again. Similar, but also very different.

Arvid Kahl 26:08
How long did it take you from like, thinking that it was gonna be version two of what you already had to understanding that it's something completely different?

Ruben Gamez 26:20
I think it was a couple of months where I was like, oh, what's going on here? You know, that feeling? And then it took a while before I just like settled, like, yeah, this is not gonna happen. So I still had thoughts of like, no, we can kind of, you know, do this and still and maybe like a year into it. And then after, I was like, ah this is not. You know, this is a different thing.

Arvid Kahl 26:46
It's funny because I do wonder you were already quite established in, I guess, the field of proposals, right? I think I looked at your blog, your blog post that kind of introduces the thing. The way you talked about it for the first time, I think your first blog post on that blog that you currently still have is from 2009. So that's been around for a while. Right? And you talked about, you had already 10 years experience back then. So you've been around for a while, but kind of you transitioned into online signature. So E signatures, which to me feels like a different field with much, maybe much bigger competitors, at least from my vantage point

Ruben Gamez 27:22
Much bigger competitors

Arvid Kahl 27:24
Right? Like, when you think about that market, you think of the big names and the things that the enterprise businesses send around all the time. What was that maybe a reason that you hesitated to understand it as something that would stand on its own in that market?

Ruben Gamez 27:40
No, at that part of it excited me. So I like that part. It was more about just like, the vision that I had going into it and like having to just let and I'm pretty good with just saying, well, you know, things are different. And it was just more of a strategy, right? Like a higher level strategy was a little bit different than like, your think this feature is a good feature. So you build it. Like, oh, they're not using it, maybe it's not that good. Let's delete it or let's change it in a way. Like all that's been much easier. And I think just from a, alright, this is how we're going to get to this, you know, milestone and we're going to open up the market and have like this higher level strategy and vision to where sometimes that's easy to change if it's, you know, but I felt really good about it. And that's when it was just like, it took a little bit of time, you know, for me.

Arvid Kahl 28:36
Yeah, I guess. Yeah. It's mostly an internal thing too, right? To position yourself for that.

Ruben Gamez 28:42
Yes, exactly.

Arvid Kahl 28:43
Very cool. So having big competitors like this, do you still consider yourself like an indie hacker underdog, doing like serving a very small niche in that market? Do you have ambitions? Maybe that's the question. Do you have gigantic ambitions to dethrone the big Docusign? Or whatever is in the market?

Ruben Gamez 29:03
Yeah. So we compete directly with them. We get people switching all the time from you know, DocuSign, Adobe Sign the big brands in our space. So yeah, we're not niche and we're not you know, we're pretty horizontal and I like the way that we're competing. And I feel like there's a lot of opportunity here because of a lot of what they're doing and because it's so tough to actually compete at the level to where mid market and large organizations will be okay with switching over to your service. It's really at the very low end for like freelancers and you know, certain really light use cases. It's a product that a lot of people can build and get into. But when you start to get into different pricing tiers and different types of use cases and organizations, then it's done. It's a different beast. And it's really easy. I talked to several founders in the E signature space about. Because before I did the whole thing, just trying to understand like, should we even do this in the first place? What did they learn in the process, like founders that had exited or founders that shut down their businesses that, you know, that had E-sign experience? And it sounded really tough. I didn't understand why from the outside, they just look pretty easy. I'm like, okay, we're kind of almost doing the same thing. I don't understand why it's so difficult. But yeah, and the one that I talked to, they had the most success in the space, just advise me, don't do it. Like he was already out wasn't even right. It was just like, yeah, it's a payment. Yes, don't do it.

Is it that bad? What are the challenges that made him say that?

I understand now, like, it sounds simple. And he was talking about, like workflow side, challenges having to do with workflows and just, there's so many like, there are technical challenges that are just kind of hidden and you won't know until you get to it. So there's a bunch of that and just very time consuming. But then there are also things that have to do with branding, you know, with like, when people are talking things that have to do with legal. Like, that can be an important factor. So you have some stuff to overcome there. And then there's also security and compliance, things that larger organizations take very seriously and can be a really big factor. So it was really from several, like perspective, several things that he was talking about.

Arvid Kahl 32:09
Is it a very price sensitive market?

Ruben Gamez 32:10
It can be depending on who the customer is. It can be not always. Like I saw somebody on Twitter talking about like, oh, I only use it a couple times a year, talking about who it was? On Twitter, talking about how they would never pay for it. There'll be a tough business and all that stuff. And it's like, yeah, we give it away for free for people like you. We have a free plan. It depends. There are many different customer segments.

Arvid Kahl 32:46
Yeah. Your free plan is something I've been eyeing there on the side for a bit, like freemium or I would assume it's freemium, right? Like, it's kind of, you get the good stuff once you upgrade, but you get the stuff that you need even for free. That's kind of always a point of contention for many SaaS businesses particularly as it is. You know, it's expensive sometimes to run a SaaS and having a lot of customers that, you know, are a drain on resources. I think, Josh Pigford, we talked about Baremetrics earlier. They had to shut down their freemium at some point because it was just destroying the service with all the data and just through Stripe that they were doing, right? But before he sold the business, he had that and I think he had something similar with maybe as well with the next business that he was in.

Ruben Gamez 33:31
It's not in like for even Baremetrics, right? Like, very successful in the space was ProfitWell freemium, not just freemium, not even like, it was like the whole thing was free. It is very extreme, super interesting strategy that they going out. You can make it work. The question really is and not in every space, but like, is it worth it? Do you have the right strategy to make it work? And should you even try to make it work and push through? Like, especially for like a lot of indie hackers that need revenue for like, early, like for a while you will make less money most of the time on freemium. And I'm not sure that it's the best ideas a lot of times to do, depends on what your personal goals. Like if you have a day job and you're like, okay, I'm done with this. And I'm doing this nights and weekends and I'm trying to get to where I can do this full time. Like, maybe not, like unless there's a really good compelling reason, you know, to do it to do freemium. And that can be. I would lean but I would lean in the direction for people in that situation towards not doing it.

Arvid Kahl 34:54
Yeah, I think everybody just hopes to be Dropbox at that point and have the kind of viral built in referral loop that then gets more people on and some of them upgrade. You know, it's kind of this wishful thinking.

Ruben Gamez 35:06
Yeah, and that's the thing. In a lot of spaces, the viral component part to it. You know, if it's there, a lot of times it doesn't even exist, like, ideally, you'd have something there. But if it's there, it's overplayed. It's not as effective as a lot of people make it out to be, especially if the space, the more established the space and the more people, the more competitors and products are doing it already, the less effective it tends to be. So also the experience of the person who can share or you know, who can kick that whole thing off is really important. And like, if they've experienced this thing before many times, they're less likely to be impressed in a way that would cause that to happen.

Arvid Kahl 36:07
Yeah, I guess. I don't know about E signatures. But I certainly I've signed a lot of documents in many different ways before. So yeah, I guess if it's a highly disruptive thing like Dropbox, which obviously could be built in a weekend

Ruben Gamez 36:24
They're always talking about the early days of that, right? Like, it's different now than it was back then.

Arvid Kahl 36:31
Yeah, that's true. That's a good point, I think, yeah, people. And that's the thing with these kinds of strategies and people only, in retrospect, see the value of these strategies, but they have moved on in many ways, right? This viral loop chasing, now we are looking at a world where the personal relationships between you as a founder of a SaaS business with your potential customers or their customers or their clients, like word of mouth becomes a much more interesting target for many businesses, right? Where sales is more personalized than not even product lead? Have you experienced anything like this as well?

Ruben Gamez 37:04
Yes, in certain segments. So word of mouth is super interesting. I think people just like, think about word of mouth is just this fuzzy thing to where it's like, it's uncontrollable and it just kind of happens. And you just build something really good and great. And that kicks off word of mouth. And the better of a job you do that, the better your word of mouth will be. And yeah, of course, there's some element of that. But the truth is, you can understand word of mouth and you can encourage it. And you can do things, too. So for example, one of the things that we looked at with SignWell was we're horizontal so a lot of people can use us, but certain use cases in certain industries. We like, how do those work? So we're not going to niche the product, but we want to understand from a marketing perspective, how we can reach more people and one of the things I mentioned before, I think on Twitter or somewhere, was education. So it's like, okay, we kind of like what's going on with education. We're mixed on it right now because the budgets are always low and you know, so, but we're like, okay, we've got a little bit of word of mouth. How is that happening? Why is that happening? So it was two things, researching like, our own customers. And then the other part was researching the space. It's like, how does education work, going into? What are the groups where they communicate? And it's more about like, not all of education, it's like, what are the sub networks within this, right? And how do they relate to each other? And how does word of mouth work in there? And then analyzing smaller brands, smaller products, new things that are not well known to have caught, you know, that caught on that started to spread that way? Like, why did they spread? So like, in that research, we found that, yes, their budgets are low. And because of that, teachers sometimes have to buy their own stuff or do you know, so they don't have a lot of money. But when things are free, they really like to share those and if things a lot of free things, education tend to be really crippled and not very useful. If things are free in a way to where it's like basically a paid product like ProfitWell, whatever, then that gets really interesting to them. And that gets shared a lot more. So we took our like paid product and we said for education. For the next year, it will be free. And we went to certain groups and people and that sort of thing helped kick things off. And sure enough, like it started to pick up just like we'd seen with other products and they started recommending this school district of that, this teacher of that and then, you know, eventually this is a long term play because you know, of course, you have to try to at some point. But that was just an example of like under learning how word of mouth works in a specific niche and doing things to encourage that.

Arvid Kahl 40:33
That's very cool. Do you run many of these outreach or even just research scenarios at the same time? Like, I do wonder, where do the ideas come from? Who's doing the research? Like, how long does it take for you to find that kind of information about all these companies?

Ruben Gamez 40:48
I usually do the research myself. Doesn't take all that long. So if it's like for education, it's literally from interviews, we learn from customers, maybe what groups they hang up on. And then we research those groups. And it doesn't it's really like, a few hours to where you start to pick a pile you have to do is just do it long enough to pick up patterns. You're like, ah, okay, I see this pattern here. Right? Yeah. And then from there, it's kind of like you coming up with ideas and things that you think will work and then trying them out.

Arvid Kahl 41:34
I love that you start with interviews like that you actually have conversations with people. Because like, personally, I tried to avoid these kinds of things just because that's, I think, how I was socialized as a, you know, a software person. You never talk to people. Like in the businesses I worked in, they never let our customers talk to us to the developers. They always put like, some marketing or customer service guy, just out of fear that we would be honest with them, you know and probably

Ruben Gamez 41:58
And say the wrong thing. Yeah

Arvid Kahl 42:00
Yeah, that's kind of they didn't train us either. They could have just trained us to have the right kind of conversation with those people. But they put different people in front of us. So I was consistently socialized. That was back in Germany. I'm not sure if it's all over the world like that. But that's just that's where I come from with the work experience that I have, not to talk to people. So that kind of still feels like that. Even as the business owner, I kind of tried to shy away from it. I tried to source my information somewhere else, not from a direct conversation or at least that used to be the case. Now it's very different. Obviously, being very active on Twitter and stuff that is people, that is interacting with people. I can't like shy away from that anymore. But as a founder back in the day, before I was active on social media, I would do everything to avoid those kinds of calls. So knowing that you have to start there to get the information, even just figuring out where they go to the watercooler conversations, right? Where they have those, that you need to ask. You need to actually ask a human being. That's really cool. Do you have a script for these kinds of things? Like do you have a set script for these interviews? Or is it more of a flexible kind of conversation?

Ruben Gamez 43:04
You know, it's a combination. It depends, like, if it's going to be like a really structured like, switch style interview, then we have those scripts from, you know, from that framework. There are a couple of really good books on there. They have a lot of great scripts on there. There's a, I mentioned it before.

Arvid Kahl 43:31
Yeah, yes.

Ruben Gamez 43:32
And then there is the other one that

Arvid Kahl 43:35
Deploy empathy?

Ruben Gamez 43:36
Yes, that one I'm really, really, really impressed with.

Arvid Kahl 43:40

Ruben Gamez 43:40
I bought it for our customer success person. She really likes it. What I like most about that one, I think is the most helpful for founders. That it's just like the way it talks about it as an ongoing process, is, is very, very, very good and a great mindset for people to get into. And then it just gives you the scripts and all the things to ask and how to ask and all this stuff. I think that one's great.

Arvid Kahl 44:10
That's awesome. Yeah, like Michele Hansen was the first guest on this podcast, just want to point out how awesome she is.

Ruben Gamez 44:16
Yeah, she's great.

Arvid Kahl 44:18
She's spectacular. She sent me like a signed copy of the book too. So I'm over the moon with the book. I have multiple copies of it. And I think Rob Fitzpatrick was a guest on the show too. Like the Mom Test is the older one. I'm so lucky to be able to talk to amazing people like them and yourself as well. Just because the knowledge that he codified in the Mom Test and the knowledge that Michele, she started this as a newsletter just sharing her experience from doing all these many customer interviews back in Geocodio, right? It wasn't even meant to be a book and then people just clawed at her. Give us the book, give us the book and turned out that that's how you write books nowadays, apparently. Yeah, it's super useful for those of us who have a, not too an easy time talking to people. Those scripts are super helpful, too.

Ruben Gamez 45:05
Yeah, yeah, I love stuff like that. Anything that's super actionable. I remember reading roommate safety's book, I Will Teach You To Be Rich. That was like, probably my favorite part of it was where you would just call these companies like credit card company or whatever. And he gives you a script, just tell them this. And if they say if you missed a payment, just say, can you, you know, get rid of the fee on that, the late fee or whatever, like nobody asks. So he has some really simple things to just ask. And I remember for the first time calling and trying it out and was like, oh, it just works, just ask. That's it. Yeah.

Arvid Kahl 45:50
Well, since we're at the topic of books, do you have any recommendations for SaaS founders indie hackers? I've got a really small tangent here because I recently looked into your blogs because I wanted to see like your oldest blog to just how far back you went. And I think you described the business you were founding as a micro ISV. You know,

Ruben Gamez 46:11

Arvid Kahl 46:12
Remember when you still called them independent software vendors back in the day?

Ruben Gamez 46:18
That's the term.

Arvid Kahl 46:20
That's how far we've come, right? And I think now we have books out like what Rob Walling's latest book about SaaS businesses. That's kind of what we call them now, right? Solopreneurs, SaaS businesses, any suggestions in the field for people who may be struggling with the things we talked about mostly real like customer, interviews, where we have two recommendations there, but just like even just understanding how to implement these kinds of processes in the business?

Ruben Gamez 46:47
Yeah, I think I'm glad Rob, he's a good friend, of course. And but like, the title of it has playbook in it SaaS, that's literally what it is, legit. It's got a lot of the things that people struggle with. So I think that one, like, it's gotta be. Like nowadays, you know, it's one of the few because before it just felt like you just cobble a lot of books together, right? So that one for sure. Let's see, I like very actionable ones. So one that I try to push on people, but people don't seem to read it. And I'm like, it's really, really good. Once you have a start to have a team or start to work with contractors or other people, is called Crucial Conversations. And it's, like, what it sounds like about having difficult conversations in a way that's very productive. And, you know, like not delaying those because a lot of times, they just get delayed until things get really bad or whatever, right? It just gives you a very specific framework on like, how to handle these conversations. And I use it as a guide, kind of, like whenever I need to refresh my memory and write notes. And then, you know, do it that way. So I think that one's super underrated and underused. And I think it depends on the type of business that you're trying to build because different books will be more useful for founders of like, if you have a sales lead business, then I would look at something like the Ultimate Sales Machine. There's Predictable Revenue, which is like outdated and like, you know, not much of it is some of it applies. But you know, I wouldn't recommend it. And then if you're like, more product lead, you know, there's the, it's called the product lead book, might even have product lead in the title. So it kind of depends on what you're trying to do. I like Ready, Shoot, Aim. Ready, Shoot, Aim. I don't know if you've read that one.

Arvid Kahl 49:08
Yeah, I've read that one.

Ruben Gamez 49:09
Yeah, so only like, I'd say like, just read the first three chapters or whatever, like, you'll know when to stop on that one. It's just a type of mindset that is interesting that a lot of people don't do. I think, Great Leads on the copywriting side, a book called Great Leads is really good as well.

Arvid Kahl 49:33
I love that for Ready Set Aim. You suggest just to start reading it and then decide if you should continue on that. That's very much in the spirit of the book. Love that. And also, I'm really happy that Crucial Conversations made it almost the top of the list here because it just shows like how much you care about communication in a team. The fact that this is a recommendation to you know, software business owner tells me a lot about how you run your own team. Now I think your team is around six or seven people, right? That's currently the size of the team. Do you still consider yourself like an indie hacker? Like a solo bootstrapper? Or was there a progression towards more like a managerial position? Like, where do you see yourself? I know you have a team and I know you lead it, but like, how does it feel like internally?

Ruben Gamez 50:21
It's still a very small team and everybody that joins the team needs to, like be able to work independently and you know, like be able to own projects and contribute in meaningful wealth way. So feels different than if I had a team to where it was just like, I'm there and they need direction from me at all times. And I am, you know, like, a manager manager in that sort of way, right? So there's like, being a manager and managing like, task based people. And then there's kind of just leading a team. And I feel like, I tend to do that more than, you know. I do work with contractors to where then I become a manager to where I'm like for a marketing, we don't have anybody for marketing, but it doesn't mean we don't do marketing. We've done a good amount of marketing. It's just that I'll come up with a strategy. And then in the earliest days, I will do the work to try and get a feel for like how this, you know, goes and I'll spend the time and then it's like, okay, I think I got it. And then I'll write some stuff up. And then I'll go to Upwork or wherever and hire somebody to help execute and then they'll do the execution, right?

Arvid Kahl 51:42
That sounds very indie hacker. Like to me still, after all these years, that's really cool. I like that. That's kind of how you approach this that you don't like over, you know, overgrow, like start to have a team of hundreds or two hundreds of people. I recently had Jason Cohen on the show. And like, his business now has its own building, right? Like, that's a different story. That's like, 1000s of people. And he seems to be fine with his role at the company that he'd be found out and stuff. But do you have similar aspirations? Or do you just want to keep a small team and work on things that you like?

Ruben Gamez 52:14
I am. Yeah, so I'm okay with growing the team up to a certain size. And then I'll see like, I'm not overthinking it too much. You know, I'm sort of like enjoying the journey. And then making decisions like I have these ideas in my head about what I like and enjoy and what things might be at a certain size. And I tend to like smaller teams. That's just me. But maybe when I get there, I might say this is pretty good. There's a lot that I'm learning. I'm growing in a specific way that where I want to keep going or maybe not. Maybe I'm like, okay, time to bring in the CEO, somebody else to drive this thing. And then I'll figure out if I'm, you know, what my role is there or not, you know.

Arvid Kahl 52:17
Yeah, that sounds reasonable. And I think that's exactly what Jason did too, right? Like, he hired a CEO for WP Engine. And the company's doing great and he doesn't have to do the CEO stuff, the stuff he doesn't like, right? So that's perfect. I really hope that you get to enjoy this journey for as long as possible. Because you've been not only have you been enjoying it, hopefully. For a long time, you've also been sharing a lot about it. You've been like sharing your insights into this not just on podcast, but also on Twitter. Do you consider yourself somebody who's building in public? Is that something you feel you're doing? Or is it not enough for that? Because you share a lot but it doesn't feel like very, you know, you're forced just whenever you feel like it, you kind of share stuff.

Ruben Gamez 53:10
I'm never thinking about building in public or anything like that. It's just it's very freeform. Like, I'll share something that I think others might find interesting or that I've been thinking about or some you know, podcasts or something like that sparked a thought and I'm like, ah, okay, like, I need to like, say this somewhere. And that's like, you know, a good place to say it. So that's kind of how I approach it.

Arvid Kahl 54:14
Well, I love that. And I'm a big, big fan of your social media content, obviously. You never cease to post enjoyable and thought provoking things. So if the listener or viewer of the show would like to find you on the worldwide web, where would they go?

Ruben Gamez 54:29
Thanks. Twitter, basically or X, I guess now like, is this like

Arvid Kahl 54:36
The other name Twitter. This has happened.

Ruben Gamez 54:39
Shoot. Yeah, earthling works. That's why I am on there. And then for, of course, document signing needs, signwell.com.

Arvid Kahl 54:50
Thank you so much for being on the show today, Ruben. That was really, really insightful. Thanks for sharing all your little insights and strategies that you have for running these really cool businesses. I'm very, very grateful.

Ruben Gamez 55:01
Thank you. Thanks for the invite. And it was great talking to you.

Arvid Kahl 55:05

And that's it for today. Ruben talked a lot about building solid SaaS businesses, even spaces where there are gigantic competitors. And a lot of founders end up in those kinds of places, that can be a lot. There's a way to capitalize on that position without having to fight your way out of it. Let me introduce the sponsor of this episode, acquire.com. Imagine this, you're a founder who's built a really solid SaaS product. You acquired customers and all of this is generating consistent monthly recurring revenue. The problem is, you're not growing for whatever reason, lack of focus or lack of skill, just plain lack of interest. You just feel stuck. Maybe there are big competitors around. You don't know what to do. The story that I would like to hear is that you buckled down, you figured it out, you reignited the fire. You get past yourself the cliches and you started working on your business rather than just in the business as people always say. You built this audience you always needed to build. You move out of your comfort zone, do sales or marketing, you just do everything, right? In six months, you've tripled your revenue, everybody's happy. Reality is not that simple. And situations are very different for each founder who's facing these crossroads. But too many times, all stories end up being stories of inaction and stagnation, until that business becomes less valuable or worse, worthless. So if you find yourself here, where your stories likely headed down a similar road, I can offer you a third option. Consider selling your business on acquire.com. Capitalizing on the value of your time today is a smart move. Acquire.com is free to list and they've helped hundreds of founders already. It's really a good idea to just check it out. So go to try.acquire.com/arvid and see for yourself if this is the right option for you today.

Thank you so much for listening to The Bootstrapped Founder. You can find me on Twitter @arvidkahl. And you'll find my books and my twitter course there, too. If you want to support me and the show, please visit the guest that was on the show today, subscribe to my YouTube channel, get the podcast in your player of choice and leave a rating and a review by going to (http://ratethispodcast.com/founder). Any of this will really help the show. So thanks so much for listening. Have a wonderful day and see you around. Bye bye

Creators and Guests

Arvid Kahl
Arvid Kahl
Empowering founders with kindness. Building in Public. Sold my SaaS FeedbackPanda for life-changing $ in 2019, now sharing my journey & what I learned.
Ruben Gamez
Ruben Gamez
Founder @SignWellApp and @Bidsketch. My personal blog: https://t.co/xrb5rfnsMg
248: Ruben Gamez — Cracking the E-Signature Market
Broadcast by