Episode 696 | The Truth about Product-Market Fit + Doing Sales as an Introvert (With Ruben Gamez)

Rob Walling:
Welcome back to Startups for the Rest of Us, I’m your host, Rob Walling, today I’m joined by fan favorite, Ruben Gamez, and we talk about some things that Ruben has learned over the past year or so running SignWell. As I talk about in the episode, SignWell is an electronic signature app that’s growing quickly, he’s having a lot of success with it. But in this episode we talk about product market fit, and maybe some of the myths around it, or the oversimplifications that we use when we talk about it. And I really like the way Ruben thinks about everything he talks about on a day-to-day basis, but especially things like product market fit. That kicks off the conversation, and I think you’ll find it enlightening if you’ve never experienced it, or if you’ve never thought about it in the way that Ruben talks about. Then we talk about doing sales as an introvert, because I get that question on the podcast a lot. 

Then we dig into decision making, that was an audible, that just came up in the middle of the episode, but I let this one run long because I really enjoyed that piece of it, and I think it’s something that more founders can learn from, and it’s not something that I’ve talked about much on the podcast in the past. And finally, we talk about hiring, getting good at it, why Ruben is so good at it, and why he has a high hit rate, and has built teams that get stuff done without a lot of drama. Do you want to reach tens of thousands of potential customers? Between our MicroConf events, Startups for the Rest of Us, our YouTube channel, our email newsletter, and all the other ways we interact with our large and growing and loyal audience of startup founders, we have a lot of options for you to reach B2B SaaS founders with your product or service. Drop us an email at sponsors@microconf.com. 

And one more thing. We’ve recently reopened the doors for our online community, MicroConf Connect. MicroConf Connect is our virtual hallway track. It’s a vibrant community of SaaS founders helping each other, and discussing wins, challenges, and frankly, how to grow faster. A couple months ago we paused new signups to improve the platform based on your requests. With MicroConf Connect 2.0, we’re rolling out three membership tiers packed with new perks, like weekly coworking, exclusive discounts, a searchable content library, and more. Whether you’ve been a member of Connect or not, you really should check it out, microconfconnect.com. And with that, let’s dive into our conversation. Ruben Gamez, thanks so much for joining me again.  

Ruben Gamez:
Hey, thanks for the invite. Good to be back.  

Rob Walling:
Yeah, back by popular demand. I’m really on a roll here, I had Asia Orangio on a few weeks ago, plan to have Derrick Reimer on in a couple weeks, and Ruben Gamez, I believe the three of you tend to be the most requested guests on this show.  

Ruben Gamez:
Nice.  

Rob Walling:
So, glad you took time here in the new year to hang out with me. In the last several times you’ve come on, we’ve answered listener questions, and obviously there’s plenty in the mailbag, so to speak, but I really wanted to have you talk about some learnings that you’ve had over the past year or two, and catch people up. It’s been a while since we’ve just riffed on things. In the past, you and I have talked about product market fit, about rules of thumb, about funnel metrics, about sale… All kinds of stuff. And you and I chat fairly regularly, once a month, and have for years. 

And so, I have some idea of what you’ve been going through, and I feel like your learnings, and the way… Not just your learnings, it’s the way you communicate them, is very unique in our space. And I sent a tweet out the other day, someone was saying, maybe you should have Ruben back on the show, or they were just saying, Ruben is the goat. And I said, yeah, his doing to talking about it ratio is like 10 to one, right? It’s like 10 x what everyone else on the internet is. And so, that’s why I want to just take the whole episode today to talk through product market fit, is one thing, and we’re going to talk about how product market fit is not as simple as we all make it out to be. That almost every conversation around it, including a lot of stuff I say on the show is it isn’t abstraction, it’s an oversimplification. 

And I want to take the first part to dig into that. And then, I want to talk about, you’re a developer, an introverted developer, for that matter, but you’ve done a lot of sales calls, and you’ve closed big deals. And I want to hear how you’ve done that, and how you’ve thought about it, as well as building your sales team. And you’re one of the most gifted bootstrap founders I know at building a team. At hiring in a very, I’m going to say picky, and I mean that as a compliment. You’re a good judge of people, and you have a high hit rate, a high rate of hiring people who work out. And when people don’t work out, you let them go. And those are unusual skills, I will say, in the bootstrap space. So, sound good?  

Ruben Gamez:
Yep, sounds good.  

Rob Walling:
Let’s dive in, man. So, first point is going to be around product market fit, but I think the overarching topic really that you said is, the whole goal of what you’ve been working on for the past year with product and positioning and all this stuff is increasing your average revenue per customer. And to catch people up, you run SignWell, signwell.com, which is an electronic signature platform, and you have both the web app side and the API side. And so, I guess the first question is, okay, so you’re trying to increase average revenue per customer. Why?  

Ruben Gamez:
Oh, good question. Because, generally speaking, customers that pay more, churn less. It’s easier to grow, it’s easier to grow faster that way, you just need a lot less customers. And depending on the category, it can actually be less competitive. In our category, it tends to be less competitive because we deal with e-signatures and e-sign laws, and once you start to go up the market, there’s more on the compliance and security side. So, there are less companies, the bar is higher, which means the competitive set, when companies are in that group where they need to work with a company that has these things, is just smaller. So, for all those reasons are why we’re focusing on customers with, they’re going to move that up for us.  

Rob Walling:
And to be clear, we’re going to call the user facing interface, your web app, and then the API is, people know the difference between those two. So, there’s two separate offerings, and your pricing is very different for them. So, the web app, you have a free plan, you have a personal plan that’s $8 a month if paid annually, and a business plan, $24 a month if paid annually. So, these are relatively low price points. Versus on the API side… We’re not talking about you raising prices five or $10 a month. We’re talking about several hundred if not thousands, literally thousands a month on the API side.  

Ruben Gamez:
Yes. Also, even on the web app side, on that side of things, we’re just selling to larger teams. So, even though the per user price is smaller, we’re bringing in companies that are… More and more companies that are in the 50, 70, 100, 200 user price point.  

Rob Walling:
Got it. And this is what I want to talk about, because you said this right before we hit record, and it’s something that I don’t think is talked about at all, about product market fit specifically. And you said, yeah, we found product market fit or strong product market fit, because you and I both know it’s not a binary, it’s a continuum. I like to think of it as a number of one to a hundred, or zero to a hundred, or whatever. And you mentioned that with the web app, we found product market fit a while ago with individuals, but we didn’t have it with teams. 

With 50, 60, 70, 100 person teams, we just didn’t have the features. So then you were looking for product market fit on the web app team side, the enterprise side, and then you moved over to the API, which does even bigger deals, and you realize, oh, there’s not just one product market fit continuum, there’s all these different use cases. And with each individual one, we have to then go find it. So, we’re going to talk through each of those mental models, or each of those phases, but to kick us off in true Startups For the Rest of Us fashion, I want to ask you, when did you know on the web app side that you had product market fit?  

Ruben Gamez:
Yeah. For us, it became… All the numbers just started to look different at some point. Our conversion numbers improved, our retention numbers, churn was lower, and growth… Ultimately, really what you’re looking for, and what you’re looking at is growth and word of mouth to pick up in a way to where it feels like, we’ve talked about this before, but you’re being pulled. And more, it started for us to feel like we’re having to keep up instead of having to grind and work and push. The feeling was different from that side of things, and this is just broadly talking about it. But it was generalizing it was just more for the segment to where it’s self-serve, it’s smaller, it’s like one person, or just a couple, two or three, and we serve those really, really, really well. It was still not that great of a solution for teams, for even 10, 15, 20 person teams, and that was pretty rough. 

So, not just that, but even on the smaller side, this is the thing with the horizontal product, it’s hard to… You’re just serving so many different industries that if you look and you say, okay, what are our top 10 best customers? We want more of those. You start to break them down. One of the easier things to do with some products is that you could just put them on a spreadsheet by revenue, and then you start to see, okay, so these are all this industry, or this vertical, or whatever, this customer segment. For a horizontal product, a lot of times it just looks like it’s all over the place. It’s like you might have accounting firms here, and then education, nonprofits and all sorts of different industries, so it can be hard to work with if you’re looking at it from that perspective. 

So then, we really started focusing on use cases, and you’ll find that, oh, education and HR, internal corporate, have this use case of they need to send one document to many people, they batch documents. So then, you can group industries that way. That’s how we look at our top customers by use case, even our bottom customers, performing an audit. What are the worst performing? Which ones use it the most frequently, but also the least frequently? And what percentage of the bottom, of the worst performing, make up our revenue? So, just to get a feel for are we adding features that are really meant for that bottom tier, or are we moving in the right direction?  

Rob Walling:
Yeah. And what I want to call out here is, the oversimplification that I was referring to, that I think everyone’s guilty of, and certainly me on this podcast is… Well, I should say, the most common oversimplification is acting like product market fit is binary. I have it, or I don’t, and it’s just has never been my experience, it’s not how it works. But let’s say it’s a continuum, the way that I like about how you described it is even with that, it’s a different product market fit with individual customer segments. And that customer segment might be a vertical, it might be hair salons versus realtors versus bankers versus SaaS founders. But as you said, when you’re a horizontal SaaS it’s oftentimes, the verticals, it’s not verticals, it’s use cases. It’s HR, as you said, HR teams at almost any company that’s 100, 200, 300 people might have the same use case, it doesn’t matter what vertical they’re in, because they all have the same need to hire people and send out things in bulk. And that’s something I think is undercommunicated, or just isn’t talked about enough in our space.  

Ruben Gamez:
Yeah. I think use cases are a big deal. They matter for not just product market fit and figuring out what features to build, but also who to go after, how to do even your onboarding and what that first run experience is like. Because if you think about it, we have use cases to where some industries just have more of a sales type use case, to where it’s simple documents, they just need signatures and that’s it. And the time to value for those is really fast. So, that means they also do one-off documents, and maybe in high frequency or whatever. 

And that just looks very different from an onboarding perspective, from a sales perspective, from the features that you’re going to build point of view, compared to ones where maybe they’re collecting a lot of data, maybe in the government forms, HR stuff. So then, if you think about the time to value, that’s longer because they have to set up documents with all these fields, they have to set up templates, they have to maybe do a bunch of training and all this stuff. And that also tends to change how we reach them and how we sell to them.  

Rob Walling:
And then you mentioned on the API side, which is a much higher ticket sale, so to speak, just higher annual contract values, that even on that side there are multiple use cases and you had to work on them in order, individually. Talk about patience. This is where folks either who have never started a SaaS, don’t realize how long it takes and how patient you have to be, or people who are working on a SaaS, and are like, but I’ve been coding for months and we’re just not going to get there. It is taking longer than [inaudible 00:13:49]. It always takes way, way longer than you thought. Because you think that you understand this full view, and usually, once you get to the top of that little summit, which is I’ll say product market fit with one use case, you realize, oh, there’s four others that I now have to build and it’s different features, and each one is a few months, so I’m talking eight months of… Or whatever, I’m making up numbers. 

But that’s usually how it feels. But the other thing you said was the further up market you move, the fewer prospects you have, the fewer customers you have, the less data you have to work with to make these hard decisions with incomplete information. So my question, because I get this a lot on the podcast, is how do you make those decisions? It’s not like it’s super clear cut. In retrospect, when the biopic is made about you and SignWell, and Aaron Sorkin’s going to write it, in retrospect, it’s going to be so clear that from day one you knew the exact vision and where you were headed.  

Ruben Gamez:
But yeah, looking back, it’s always super clear.  

Rob Walling:
It is. So, what is it? How are you making… You’re in the midst of this. How are you making those decisions these days?  

Ruben Gamez:
Yeah. So, you are working with less data, typically the more you charge, that’s just the game. So, because of that, you have to go deeper with each of these customers, and understand them at a… You have the time and you don’t have a lot of data by volume, but you can get a lot of data by depth.  

Rob Walling:
Qualitative versus quantitative, right?  

Ruben Gamez:
Yeah, exactly. Right. And you do qualitative even with volume, but a little bit less. And you’re just depending on the numbers being so high for you to understand the full picture, but you don’t have that. So, you have to talk to customers, and you have to sell, and you have to do… Every time you’re interacting with a company, you have to try and gather data that will help you in this journey. And then afterwards, after you sell them, not be afraid to come back and be like, I’ve done this on the API side and with teams, with companies that we don’t have a lot of, but we know this is a good customer and we want more of. 

And it’s just, we need to understand as much as possible about this customer, how they buy, what triggered the process of buying? Who was involved? What were the conversations like behind the scenes? What are the things that are important to them? What were they worried about when getting started? All this stuff. And the more you know that way, the less people you need before you start to see patterns. You still are, it’s not going to be perfectly clear or anything like that, but that helps a lot.  

Rob Walling:
And so, you take this qualitative data, and at a certain point you just have to go with your gut?  

Ruben Gamez:
Yeah. So, part of it is where you want to go with the company, and what you see. Because you just have to think about, okay, we like this type of company, how many more are there out there? And the thing that I think a lot of people miss is, oh, what can we… So, everyone focuses on what they can build. It’s like how long is it going to take to add these features, and will there be more companies that will use these features? How big of a market is it? And the thing that I think a lot of companies overlook is that they don’t think about how easily they can reach them. How good are they at selling to them? You can have a really big market. So, for us, an example is real estate. And this was early on, we saw, okay, this use case has more of a back and forth than some of the other use cases. 

So, this back and forth is good for real estate and a couple other industries, but not many. That market is really big. There are e-sign companies that are just real estate. And looking into it, and researching it, there were things that I found that I felt made it harder for us to reach them and sell to them. And it’s not necessarily just a general thing, these are hard to… Sometimes it’s like that, like, oh, they don’t like to talk to sales, and they don’t hang out online, and all this stuff. 

But none of that matters if you have a way to reach them, like, well, we have good relationships with these organizations, or a superpower for us and our company DNA is doing this, which is a really good way of reaching. We didn’t have any of that. So, because of that, plus we were lacking just expertise when it comes to how to sell to real estate, and how all that works, it didn’t feel like a good… And we purposely ignored building those features. And we still have a good amount of real estate customers, but there’s a lot more that we can do to better serve that. And we don’t have product market fit for that segment, those types of back and forth use cases.  

Rob Walling:
And you’re just willing to do it.  

Ruben Gamez:
And we’re okay. You have to decide, right? Prioritizing is a huge part of it. There’s only so much you can do, you have to pick and you have to decide what you’re doing. But also, what you’re not going to do.  

Rob Walling:
That’s the big conversation. And I don’t like it when people use Steve Jobs and Basecamp as examples, Apple and Basecamp. But there is a quote that I like from Steve Jobs, where, I believe he told it… It’s Tim Cook quoting Steve Jobs. And he said, one of the things he told me is, “There will always be 1000 good ideas, and usually we have time to pursue one.” And so for every 100 or 1000, or whatever the number is, we have to say no. And we will be great by saying no to a lot of things. And that’s prioritization. Maybe he’s overstating it, maybe he’s exaggerating, you can do more than one thing. But the reality is, in the final days of Drip when I was there, we’re doing tens of millions a year in revenue, team is 125 people or so, we were getting close to… I think it was about 175, 200 feature requests per month. How many can you… Even with 18 engineers?  

Ruben Gamez:
Yeah, you’re not going to do all that. Right. No, you have to find a way to prioritize. Yeah.  

Rob Walling:
Exactly. And some of it, and some people prioritize with a spreadsheet, and some people like Derrick and I, and I think you prioritize, I would say it’s gut feel that acts I’m just either smarter than I am, or I just don’t give a (censored), and I’m just picking (censored) randomly with a dartboard. It’s neither of those. It is this, there’s an intuitive side, there’s a right and a left brain, a creative and a science side. And the spreadsheet is science, and that’s helpful. And so, when we hired the first product person, aside from Derrick and I, he was very much in that left brain spreadsheet mode, and that balanced us out a bit, I will say. It was helpful to have that voice on the product side, but that voice alone would not have made the right decisions.  

Ruben Gamez:
Yeah, gut’s a really big part of it. I always felt like you’re really good at this, and you’re decisive, and you tend to more often make, from what I’ve seen, make the right decisions. Not always, but a lot of the time. More than a lot of other people. One thing that I’ve wondered about the way that you do it is, do you feel like you’ve developed that, or are there things that you’ve done or that you do that you think help improve that gut feel?  

Rob Walling:
This is a really good question, and I’ve thought a lot about it, because one of the talks that I’ve given is… I forget exactly the title, but I gave it in South Dakota a few months ago. And it’s nine traits of the best startup founders. And I couch it in the first five minutes of, here’s what I define as best. I’ve invested 171 companies, I have pretty in-depth data about 171 SaaS founders. And I can tell when the founders are having an outsized impact. It’s not just you’re successful, because sometimes you’re successful and you got really lucky and it’s not actually the founder. You and I have seen that. But given the relationship I have with the TinySeed founders in my private investments, I have patterns, there’s pattern matching that I see across my… There’s a framework I have of it. And one of those things is they generally tend to make the right decision more often than not. And, as you said, it’s not 100%, but it’s somewhere in the 60 to 80% range I think. You can be as low as 50 and it’s still probably not that bad. 

This is Rob popping in a day or two after Ruben and I recorded this episode, and I thought back to that statement that I just said, about how if you’re making 50% of your decisions correct or right or mostly right that you’re doing well, and I disagree with that. That number is too low. That’s basically like flipping a coin. As I thought more about it, I think if you’re above two thirds, maybe 70%, 75%, you’re doing pretty good. And I think the better you get at this, I think really experienced founders who know what they’re doing are probably in the 80 plus, 85, 90 plus. It’s like eight or nine out of 10 are at least in the ballpark. 

And as Ruben and I talk about measuring right or wrong can often be hard, it’s usually not just two choices, there’s creative choices, and oftentimes there’s 6, 7, 8 different paths, and you don’t know how they all would’ve panned out, and multiple options can be “right” or turn out poorly or whatever. So, it is all a bit hand wavy and fuzzy, but I just didn’t want to leave it on record that I said, oh, if you’re a founder making 50% or more of your choices, that you know how to make good decisions, because I don’t believe that’s the case. And now, let’s get back to the episode. 

I often list several founders off the top of my head who I think are really gifted founders, and are really good at it, and could do it over and over, and it’s Hiten Shah, it’s Jason Cohen, it’s Steli Efti, so there’s a bunch of folks who’ve been MicroConf speakers. They just tend to make the right decisions. And so, I’ve thought a lot about, well, how do you get better at that? Because it feels like this very intuitive thing, but I used to not be good at it, and I used to second guess myself a lot. And I think the ways I got better at it were by talking to people, either having advisors or having mastermind compadres, like yourself, who think about things differently than I do, and who make decisions differently. I used to make impulsive decisions quickly. You think a lot more in depth about decisions. And that steered me into balancing. What’s my weakness? I know myself to know, oh, a weakness is I’m uncertain, I’m not decisive, I think about things too much, and then eventually I just (censored), I’m just going to make an impulsive decision. 

That’s how I used to do it, say 15 years ago or more. And you balance me out. Just watching Hiten Shah execute, he was an early influence on me because he was a MicroConf speaker, and he was ahead of us, in terms of Crazy Egg, and just with KISSmetrics. Watching Jason Cohen execute. So, some of it I could do from afar, because Jason Cohen and I, we’ve done Zoom calls over the years, but it’s not like we talk every month. But you just observe him, and you read his blogs, you hear him talk about his decision-making. And it’s like, I want to be more like that, he seems to make some good decisions, and being-  

Ruben Gamez:
Some pretty good decisions, yeah.  

Rob Walling:
And being around you on a more ongoing basis, again, we have that monthly touchpoint for more than a decade, that also helped. And then, here’s what the interesting thing, even with TinySeed founders today, watching founders, there are a lot of founders that I work with, and I’m like, wow, you make really good decisions, and I’m still learning from them. They might be better at me than making decisions. And so, I pick up on little things… I’ll say, explain to me why you made that decision. And when I hear them talk it through, I’m like, ooh, that’s smart. That’s a neat framework, or a neat way of thinking about it. So, that’s the answer. The answer is I do believe you can develop this, because I certainly didn’t have it, and I would agree with you, these days, I do have it. And that’s not overconfidence, it’s I generally make the right decisions. 

So, I definitely think you can learn it, but I do not believe you can learn it in a vacuum. I think you need to be listening to the right people. And by listening to… Do they have a podcast? Or can you read Jason Cohen’s blog? Can you read my book, the SaaS Playbook? Hopefully I help you make some decisions. I have a thing in there about risk versus certainty and decision making. It’s like, are they putting stuff on the internet in a way that you can follow them, or do you know them personally? I know you [inaudible 00:25:51], that’s actually really good at making decisions, and I’ve learned from him even in the past five years of working together. So, does that all make sense? And does that align with your… Because I feel like you’ve always been pretty good at making these types of decisions, to be honest. But do you feel like you’ve learned it, or got better at it, or was it a natural thing?  

Ruben Gamez:
Yeah, what you said I think makes a lot of sense, and there’s a lot of overlap with how maybe I think about it. I’ve studied, of course, just decision-making, and things you could do to make better decisions. But being exposed to ideas from others that may be different, observing people that are making good decisions, and trying to at least consider and analyze that a little bit about why did they do this? And knowing yourself I think is a big one too. A lot of this stuff is really about just getting out of our own way. Knowing what we tend to do that messes us up, and then counteracting that, and however you need to do that. I think that’s huge. And then, being truly open to-  

Rob Walling:
To learning and getting feedback?  

Ruben Gamez:
Yes, yes.  

Rob Walling:
To asking, if I’m making a decision and I say, hey, five smart people I know, tell me what you think about this decision? And they all tell you the same thing. And then you say, oh, I’m going to do what I thought originally anyways, that doesn’t help you.  

Ruben Gamez:
No, no. Right. There are people, and we see them sometimes, there are people that ask for feedback, or put things out on Twitter or whatever, seemingly to get feedback, but not really. People give them feedback, and if they don’t like it, if it doesn’t align with what they’re thinking, they shut it down. You can’t get good that way, you can’t get better, you can’t improve in that way.  

Rob Walling:
Yeah, I like that. That’s a good way to think about it. So, I want to switch up topics and talk about sales as an introvert. Because you have had to do a lot of sales calls as you’ve moved into this upmarket position, especially on the API side, I’m assuming on the web app side too. A question I get now and again is, I’m introverted, and I don’t really want to do sales, but I have to do sales, how do you do it? Or should I just not? Should I automate everything? You and I stand the same on this. You do what it takes.  

Ruben Gamez:
Right.  

Rob Walling:
If I want to build a multimillion-dollar company, if I want to have an eight figure exit, I’m going to do what it takes whether I want to or not. And so, I don’t like sales, I’m not a good salesperson, I’m introverted as well. I don’t like talking to people I don’t know, Ruben. I have a small circle of friends. And so, how have you gotten over that?  

Ruben Gamez:
Yeah, there are just things that you do because you have to do to move things forward, and they tend to be easier if you know that they’re not going to be permanent things. You’re doing them to get to a place where you can bring on somebody who will do that, who truly enjoys doing that. So, sales for me is, I can kind of enjoy at times, or parts of it, and I can see how people can be so into it that that’s what they want to do for a living. I don’t want to do that for a living, it doesn’t give me energy, it’s one of these things that takes energy away from me, to where I need to recharge afterwards. Being that it’s important for the things that I want to do with the business, I’ve just made it an effort to learn how to do it better, and I’ve put myself in situations to where I’ve had to practice it. 

So, that’s another part. And then, I’ve just talked to other… Same process that I do for anything else that’s new that I’m trying to understand and learn and get better, practice taking in information and then talking to people who are doing it, and learning from others. So, learning from Jordan Gaul, who’s doing a lot of that, I’ve learned a lot from him. Matt Wensing, who’s really, really good at it, and has given me some great tips and advice in the middle of negotiations and all that. And even hiring expertise, and we have a sales advisor that worked in our industry and did exactly the stuff that we want to do, that I’ve hired to help us out and give us advice on this. Yeah, those are the things that I’ve done to help.  

Rob Walling:
So, it’s valuing the business… Not even valuing, but prioritizing the business or the growth over your personal preference of what you want to do. And it’s not what you want to do eight hours a day, 365 days a year. It’s, now and again, I have to do a sales call, and I don’t particularly want to do it. But I’m going to grind it for now, knowing that I’m going to hire this out eventually. But right now it really needs a founder. And then taking information in and iterating, and getting good enough at it… I don’t think you’d call yourself an amazing salesperson, would be my guess. But you’re good enough.  

Ruben Gamez:
Exactly. And I think, even for things like this, to where it’s not my favorite thing in the world to do, I think it really matters, the energy that you come at these things with. It really does. If you’re going into it just dreading it, and thinking about how much it sucks, and all this stuff, then it’s going to be rough. It doesn’t have to be that way. So, I tend to think about things at a higher level in the way where I’m not thinking maybe so much about the specific sales conversations and the tactical stuff. If I’m thinking about the type of energy that I want to bring into something, so I’m not all pissed off and dreading it, I’m thinking about it being a puzzle. All this stuff, these are puzzles. And I love figuring things out, and it’s about figuring this out, and figuring these things out. 

So, there was something I read recently, they were talking about… I don’t remember where it was, maybe it was a podcast. But I like the way that they phrased it, to where they’re saying, once you’ve made the decision, go all in, and go into it with a positive energy and attitude as much as you can. It makes no sense making the decision and then afterwards just trying to fight it. If you’ve decided you’ve decided to do this thing.  

Rob Walling:
Then do it. Stop waffling.  

Ruben Gamez:
Yeah.  

Rob Walling:
Go in.  

Ruben Gamez:
Yep. Exactly.  

Rob Walling:
Yeah. And I like what you said right before that, essentially gamifying it. To you, it’s like, huh, I don’t like sales, but you know what I do like? I like my MRR going up. I like having a challenge that I really am not good at, and that I’m going to be good at in a week, or a month, or six months. And I’ve often thought about building businesses like that. I built several businesses, pre-Drip that I kind of didn’t care about. I had these little, you remember, little eBooks about bonsai trees. 

Or I’m trying to think… I had duck boat plans, where you could build your own duck boat. And it’s like, they were quality things that I stood behind, I wasn’t just shilling crap. But I liked the product, I wasn’t passionate about the product or the niche, but I gamified it in the sense of how high can I rank in Google for all the terms? How fast can this grow? And it wasn’t… One of them did $500 a month, it wasn’t even MRR, it was just in sales of this $30 ebook. But it was still this fun challenge that I could work on. And I was learning, and if I screwed up with those, screwed up and Google booted it out, it didn’t matter. But it was still a fun challenge.  

Ruben Gamez:
Yeah. There were legitimately fun things about those.  

Rob Walling:
Yep. So, I want to mix it up and talk about hiring and firing. And really, I think the overarching thing is building a team and building a functional team that gets (censored) done, and that I never hear an excuse from you, of like, yeah, I don’t know, there just aren’t any good developers out there. Or, my team’s really dragging us… We’re not making progress because of my team. You just never say that. Because I think you tend to be pretty picky about who you hire, I think you tend to fire pretty fast, and somehow you find… Even during COVID where we were at, bootstrappers were at a disadvantage again, because everyone was remote, and usually being remote is this big advantage. Even during COVID, you still kept making forward progress. 

So, what is your mental model around this? Why are you… Again, I was telling you offline, you’re probably in the top 10, 15% of all the bootstrap founders I know, in terms of hiring, firing, motivating, building a team, basically the overarching thing of your team. It’s not just software, it’s the whole team. They just get (censored) done, you have good people who are competent, who are doing customer success and support and all this stuff. And a lot of founders struggle with this, and I don’t know, it’s like, Ruben, are you a natural at this? Or do you just have a framework or two that you think could help a listener who might have no idea what they’re doing?  

Ruben Gamez:
So, I didn’t know that I was as picky… I felt like, I’m a little picky, but I didn’t realize maybe how much more picky I was than the average founder hiring, or company hiring. Until recently, where I was working with Dynamite Jobs, I think, is that what they’re called? I’m not sure.  

Rob Walling:
Yeah, they’re called Remote First Recruiting now. Yeah, it’s Dan and Ian from Tropical MBA. We use them at TinySeed and MicroConf as well, to help hire.  

Ruben Gamez:
Yeah. And they do a good job of putting the job descriptions out there, and taking calls, and doing an initial interview and then sending you people that they think are good and qualified, and getting feedback if that needs an adjustment, and then sending you more people. It was something they said to where we, we were at about person 15 or something like that that they had sent, and Krista who had been working with on that, I don’t remember what I asked, but she said something like, well, actually, typically we send about three to four people before a hire is generally made. I was like, really?After the second, third, fourth person, that’s it? I feel like people are maybe a little bit too quick to hire, and maybe some of that comes from, we really need somebody and we need to fill that role. There’s some pain there. And not being willing to just wait to find the right person. 

I think that’s part of it. Also, when you’re hiring for a new position or something new, I tend to do the same thing for sales. Sales advisors are very involved in helping hire this person, helping… I don’t have the experience to have the gut feel yet for this being a really good person for this type of position. In certain ways. I understand if somebody’s well organized, and they have good attitude, and all this stuff, but there’s some gaps there, and I think it’s important to fill those gaps with help and expertise when you can. And then, I do follow, I like the book, Who: The A Method for Hiring, something like that, to where it’s a very specific process, to where part of it is, beforehand, I think an important thing that maybe some people skip out on is identifying what makes a great hire, and going down the list of the things that you’re really looking for, and then when you’re interviewing people, scoring them, they call it a scorecard, against each of these things. 

If it’s selling, their ability to follow up, their expertise with selling to the mid-market or enterprise or whatever, what people tend to do is, they’ll get somebody that they really like, and they think is really good, but maybe they’re not as good in the areas that they thought initially going into the whole process, that they needed, and they end up hiring this person, and then it doesn’t work out. Because it’s not… They just feel like, oh, this person’s a really good… And you’ll hear this sometimes, if you come across a really good person, then just hire them. But when you’re a small company, you do tend to have very specific needs, and there is less room for that. That, and then, one of the other things, even with hiring contractors agencies and things like this, I tend to keep track of companies… No, I should say, of people, that I think are really smart and good and doing interesting things. 

And I do that, often, I see them on Twitter or something like that, and so I literally have a bookmark for freelancers, writers, or marketers. And this is just random people that I think are really smart, doing super interesting things, that might be working at a company, might be working for an agency, might be freelancing, might be whatever, that I might at some point in the future want to work with. Maybe an external agency or something that can help us with things, or if they start something like that, or a freelancer, or hire them. Hey, this person, if they become available, and we’re looking for this type of position, they would probably be pretty good. I think it’s helpful, I’ll say, to always do that, even if you’re not hiring for that specific thing.  

Rob Walling:
Right, you’re just paying attention because you know that you’re going to grow.  

Ruben Gamez:
Yeah.  

Rob Walling:
It’s interesting what you say about being picky, because I used to be accused of that as well when I was a development manager at a credit card company. We’d hire these contingency recruiters that make an egregious percentage of the first year salary, 15% or something of 100, at the time, 120, $130,000 salary. But they only do it if you hire them. So, there was all this pressure on us, and the recruiters would get so mad, and they’d be like, what are you looking for? Can I see your resume? Do you have the stuff you’re asking for? And I was like, no, you can’t, A… And my boss got super mad when they asked to see my resume. But I said, no, I’m just not going to hire someone who’s not a fit.  

Ruben Gamez:
That’s funny.  

Rob Walling:
Yeah. And the thing I think about… Maybe I should write this out at some point. But when I think of… You were talking about evaluating someone. Let’s say I’m going to hire a designer. If I simplify it, there’s three skills a designer needs. This is oversimplification. But they need the actual design skills, the chops to do it. And whether I’m going to hire or just for a one-off job, are they a good designer? And you know how I can evaluate that? It’s easy. Go look at the (censored) designs.  

Ruben Gamez:
Their work.  

Rob Walling:
Yeah, just look at the work portfolio. So, designers are actually, in my opinion, easy to evaluate, because I can look and say, I like that, or I don’t. I think they’re skilled or they’re not. That’s the easy part. But there’s two other factors that are hard to evaluate. The first one, I guess it’s the second one of my three, is communication. Do they take feedback and iterate well? Do they communicate with you and say, oh, I’m going to be late, or… Whatever. Are you able to have a back and forth with them in a way that the two of you understand each other? So, communication, and that’s what I’m going after in an interview. I’m trying to suss out, I know what your skill is, I can see your design. So, I’m trying to figure out, can you communicate, let’s talk about some complex topics, and figure out if we’re on the same page. And the third one, I’ll just say, do they deliver? Meaning can they hit deadlines? That one is the hardest of the three to figure out.  

Ruben Gamez:
That is, yep.  

Rob Walling:
Because you can’t figure that out by asking them a question. It has to be either references, or maybe you ask, hey, when was the time you didn’t hit a deadline, how did that play out? And listen to how they talk about it. And if they’re like, oh man, it was two years ago that I totally missed a deadline, and here’s what I did. Or if they’re like, oh yeah, so a couple of weeks ago I did this. It’s like, huh? But even that’s not 100%. It’s just, we are trying to evaluate. And if anything of when I’m hiring designers, usually the thing that I miss is that they don’t hit the deadlines and they’re unreliable, because that is the… I just know there’s uncertainty in that. And it’s hard in an interview process, until I work with them, figuring that out. Similar, let’s say we’re hiring a customer support, email support rep, for a SaaS company. 

Again, I think there’s about three things. One is communication, for sure. Can they type the email or the live chat [inaudible 00:41:48]? Second is, will they get the understanding of your customer and your product? I think that’s the second thing. Can they [inaudible 00:41:55] that and get it all in their head? And the third one then I think is speed. Does it take them five minutes or 50 minutes to write this email? If I gave more thought to it, maybe I would pick different ones. But I think those are the three. Now, can I figure out communication? Probably. I could probably email them with them, I can talk with them during an interview. Can I figure out whether they’re going to understand my customer and my product? That one’s tough. I would do it on a sample project.  

Ruben Gamez:
Yeah. We have an application… We hired for that. We have an application for that. To where, sign for the product, do this task, upload a document, all this stuff, and then fill out this form that has these questions, from real customers that we’ve asked, to where they don’t know the product that well, but they have to answer the questions, and see if they can find the right answers, or understand, a lot of it is about understanding what’s coming at them.  

Rob Walling:
Yep. So, all that to say is, without those mental models or without any experience hiring, I think people… I’ve heard this phrase used of, resume and small talk. Where, I get on an interview with anybody, developer, designer, support person, and I’m looking at their resume, saying, oh, they worked at Google, they worked at Facebook, they must be really good at the… No, don’t do that. Or they were there seven years and they became a senior, blah, blah, blah. It’s like, so? I worked at a ton of companies with (censored) people, with dummies that rose to senior manager.  

Ruben Gamez:
Right, yeah.  

Rob Walling:
Don’t use that. That is one of the least important things. I look at tenure, I look at some experience, blah, blah, blah. But I’m trying to get into nitty-gritty, and ask them, I won’t even say hard questions, but just questions that actually get to the root of, what are the skills that they need to succeed at my company? Because guess what skill they don’t need? The ability to work at Facebook for three years is not a skill you need to work for me.  

Ruben Gamez:
Yeah, no, that’s a good point. There is generally some sort of exercise to try and evaluate the quality of the work. And depending on the position, you can, on the design side, you can tell, on the development side, even on that side, we do have people that go through a four-hour coding exercise and all that stuff. And that’s been, we’ve improved that to where it tells us pretty well where they are on at least the code quality point of view. So, that helps. And if you can work with them, of course, on a smart project or something like that, that’s the best, then you know. But that’s not always going to be the case. 

But, like I said, we hired both a developer recently that did that, and then on the customer success side, also for support, we’re having a lot of people just not being able to understand, or understanding but missing little details that matter and that result in a bad support experience, because somebody’s… It’s like, wait a minute, you’re not… And we’ve all gotten this, to where we send in the support, and then they just send in a copy and pasted reply, or link to support article, and you’re like, no, you’re not really answering my question. 

Yeah, that’s a big part of it, and then in the communication part, that’s partly why we have everyone write, in their application, we have them write why they were interested in the position, all the basic stuff, and then just get a feel for their writing and their communication. Generally, even in the exercise, there’s a feedback and improvement part. Can you change something? And this is about seeing if they’re open to criticism, and if they’re open to write some pushback and all that. And it’s not super strong, but you’d be surprised at how many people are just… The way that they take… It doesn’t have to be super obvious, it can be subtle, to where were like, ah, okay, there’s something there.  

Rob Walling:
There’s something there. Yep. And there are skills, like you’re saying, that are easier to evaluate, like communication, or response time, or understanding. And there are certain skills that in any role are just harder. They’re just harder. Like hitting deadlines and this and that. It’s like, I can’t figure that out in a interview, I need to do a sample project. And I think having that dichotomy or whatever it is, that mental framework in your mind as you go into interviews, I think can be helpful. Because I’m going to check the boxes for the ones that I can evaluate, and then the other one I’m looking out, this is why people do trials, 30-day trial, or a single project trial, if it’s project-based, to try to suss out that other one or two. And if there’s any wavering, you just cut bait.  

Ruben Gamez:
You know what’s pretty good, surprisingly good too? Is the question where I’m asking… You ask everyone what are you not good at, or what do you want to improve, and all that stuff. And they’re all like, oh, I’m too much of a perfectionist and blah, blah, blah. And then, the one where you’re asking about specific jobs, and who they work with, and if I ask, who did you report to at that place, at the job? Okay, so I ask so-and-so what they thought was something that… If I asked them, what’s something that they could improve in? What’s an area that they could work on? What do you think that person will…  

Rob Walling:
Right. So, your former boss.  

Ruben Gamez:
Yes.  

Rob Walling:
What would your former boss say that you could improve about yourself?  

Ruben Gamez:
Yeah. Being specific at each one of the jobs. It actually works really, really, really well. Sometimes you’ll get pushback toward, oh, I don’t know what they would say, and then at that point, it’s like, they don’t want to say anything bad, but I say, sure, I get that. But somebody like Christian on my team, he’s our lead dev, he’s great, but he also wants to know how he can get better. So, I go out of my way to let him know, because nobody’s perfect, how he can improve. So, what would they say, in your opinion, that would be… And usually though they know, because those conversations have been had, so then when they say the thing, it’s like, oh, can you give me an example of that? And it’ll usually come up like, yeah, it came up because of… And these types of things will give you clues into their strengths, and maybe the areas where they’re not so good.  

Rob Walling:
Right,. And another point you just made, without even making it overtly, is sometimes you have to ask a question two or three times. Sometimes you have to push a little bit. You don’t have to be a jerk, but I ask some hard questions, very tactfully of people. I’m the guy in our TinySeed interviews, it’s like, so I can see your churn is 12% per month, I’d imagine you want that to be quite a bit better, because that’s not good? Or talk to me about why it’s there. Talk to me about how you thought… So, basically, I could have said, your churn is (censored) catastrophic and your business is on fire, why haven’t you fixed it? That’s one way to ask it. Or you can ask it the way I just did. So asking… So you don’t have to phrase things like a jerk in order to ask hard questions. And that’s actually, Crucial Conversations is a book that you recommended to me years ago, and I learned a bit about phrasing and all that from there.  

Ruben Gamez:
Yeah. No. And coming at it… That’s a good point. Coming at it multiple ways, because people will try to give you fluffy answers. It’s like, oh, so for this project, give me an example of this, what happened? What was something that where you ran into… What was a tough time at the company or whatever? It’s like, oh, blah, blah, blah, so and so, we had a problem with whatever. And it’ll be very fluffy. It’s like, oh, tell me about that. And then they’ll kind of tell you, but it’ll still be high level. It’s like, yeah, I wanted to understand what happened there, tell me about your thinking. What kicked it off? And you sometimes have to push a little and just keep asking.  

Rob Walling:
Ruben Gamez, you are earthlingworks on Twitter, everyone should rush over and follow him there. Thanks so much for taking time to come back on the show with me.  

Ruben Gamez:
Thanks. Always great being on here.  

Rob Walling:
Thanks again to Ruben for joining me on the show, and thank you for coming back this and every week. This is Rob Walling signing off from episode 696.