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This is your destination for feeling empowered in building your business.
These are the real, raw stories of entrepreneurs and business owners who have built their businesses through the messy middle of $1-20 Million, hosted by serial entrepreneur Matt Tait.
Matt knows what it’s like to scale past the first million, and on this show he’ll be bringing on other serial entrepreneurs and business owners who have been there, done that (or, are currently in it) to share what’s worked, what hasn’t, and what’s next.
Transcription
DECIMAL | AFTER THE FIRST MILLION | WIEY JONES
Episode Transcript
This has been generated by AI and optimized by a human.
Wiley Jones [00:00:00]:
I think my journey for a very long time as a founder is going to be about balancing the inherent skepticism I have for my own ideas and the inherent conviction I have for my own ideas. You know, if I have to think about, like, what my journey is going to be building this company, it's going to be in how I reconcile those problems on a daily, weekly, monthly basis.
Matt Tait [00:00:22]:
I'm Matt Tait, founder of Decimal and fellow entrepreneur. Yes, I'm one of the crazy ones. I've chosen time and time again to hustle my way through that first million. Now I'm scaling to the next 50, so I know firsthand what the messy middle is really like. And I know that entrepreneurs and leaders like us need a destination for empowerment, community, and encouragement. This is our place. This is After the First Million. All right, welcome to another episode of After the First Million.
Matt Tait [00:00:55]:
I'm your host, Matt Tait, and I am really excited today to have a conversation with Wiley Jones, the CEO and co-founder of Doss. And this is going to be a fun conversation for the After the First Million listeners because we're going to talk a lot about what Wiley's going through today, how he's scaling his business, and I think we'll have a fun conversation. So, Wiley, thanks again for joining us.
Wiley Jones [00:01:20]:
Thanks, Matt. Appreciate it.
Matt Tait [00:01:22]:
And now that you're running a business, I bet you'll agree you kind of have to be a little bit crazy to start your own company. So when did you realize you were one of the crazy ones?
Wiley Jones [00:01:34]:
The original version of it was more about what we're working on and less about the company itself. The problem kind of was an emergent thing where I had, you know, worked for quite a while as an electrical engineer. I designed a bunch of cameras and hardware products, and I had a lot of fun doing that. I actually love doing it and I miss it quite a lot even today. But there was a lot of problems that I ran into as an end business user of a lot of the things that now we at Doss are going and working and replacing and bringing better solutions to market. And so, you know, in the process of basically banging my head against the wall for many years using these tools, no one else is going to fix this. And if no one's going to do this, then I have to do it. And so it was less about, you know, I would say, wanting to go out and start a company and more about going and solving a specific problem and the compulsion to do so.
Wiley Jones [00:02:29]:
It just required that I had to start a company. And that was kind of like then the realization when people talk to me about this later on, you know, maybe like a couple, you know, a year or so after starting the company, they're like, oh, did you go and find a problem and you really wanted to start a business? And I was like, no. I was like, the idea of starting a business was like, always the last thought. It was like, oh, it's just kind of like a byproduct of like what we need to go and work on. So I think we're crazy for a bunch of other reasons. But, you know, starting the company was always just kind of like something we had to do to actually work on this problem.
Matt Tait [00:03:00]:
I think that's really cool. And it's so different from me and a lot of the people I talk about. Like, I grew up always wanting to be an entrepreneur, and so my entire career was seeking out problems that I could create companies for and solve them. But I do see with engineers that a lot of times people with engineering backgrounds, you kind of get locked into a problem, and sometimes you're able to solve that problem within a role and within another company. But other times, and it seems like it's a little bit of target lock of I'm obsessed with this problem, and I'm obsessed because I know there's. I know the solution or I know how we'll get to a solution. And by the way, that's also going to create a company. And it sounds like that's how kind of the impetus behind Doss.
Wiley Jones [00:03:53]:
Yeah, that's exactly it. I was actually recently at a retreat with a bunch of other CEOs and founders of companies that was sponsored by one of our investors. And we really broke that down exactly like you said, into kind of there's just like two types of entrepreneurs. There's people who are compelled into doing it by the nature of who they are as a person and that they want to be going out and building companies and building businesses. And then there's people who are compelled into it by the problem set that they have to focus on and that they can't go and be a person that solves this problem inside of a large company or some other, even maybe small startup, that they just have to start from zero and address the entire issue. There's a funny interview question of, like, there are two types of people in the world. Like, what are they? Right. You know, I think there's two types of entrepreneurs in the world, and that's the fundamental divide in my mind.
Matt Tait [00:04:37]:
One of the things I find is interesting and I'll be interested and so, number one, I totally agree with you on, on that take. I think it's not just engineers too. It can be somebody that's starting a plumbing company as I found a problem and I can solve it better. And so I'm going to start a company that umbrella holds for just people running businesses. But what I think is fascinating about people that come at the problem as the only way to solve it is to build a company. At some point you also realize that you're not just building a solution, you're also building a company. How has that realization been for you?
Wiley Jones [00:05:17]:
It has been an act in being present and re-centering my intentions, which I think lots of product focused, engineering-focused founders, I think run into this problem where they get frustrated pretty quickly in the journey of the company that they go, man, my job is a sales job. Like, I want to work on the product. I started this so I could work on the product. I started this so I could think about whatever the systems that are interesting to me are. And it turns out that the bulk of your day to day is about aligning people, recommunicating and reiterating the same things over and over again. Selling your vision of, you know, what you do, why you do it, how you do it to the broader world, which is fundamentally what marketing is. You're marketing yourself, you're marketing your vision, you're marketing the company. And for me, it's been like having to recenter those intentions on a very regular basis, being like, okay, if I want to have the opportunity for our company to continue to exist and the opportunity for us to continue to work on all these fun problems, I have a duty to market us and sell our vision to the world.
Wiley Jones [00:06:22]:
It's almost like this meditation on what the founder's purpose is. And you constantly have to recenter yourself. It's so easy for me to like, see what an engineer is doing when I walk by their desk and I'm like, ooh, what are you working on? And like, and I get sucked into it. You just gotta avoid that. That's one of the big things for me.
Matt Tait [00:06:39]:
When you start, you're like, I'm gonna solve this. And then at some point, successful founders do the we're going to solve this. How has that kind of transition been too?
Wiley Jones [00:06:50]:
I've given myself permission now in the last, let's say, year we started the company, almost two years and like a few months ago. So like in the last year I've really given myself permission to let the company be an expression of self and that was like something I kind of held back from for a while. I was like, oh well, I need to make it palatable for everyone. I need to follow the patterns that I have seen out in the world of like this is what Amazon does and this is, you know, the Steve Jobs thing and then here's the Bill Gates thing and you kind of like you're trying to pick pieces, right? And then eventually I just like, I kind of wiped that all off and I was like, I just need to make the company about what we believe, my co-founder and I, and we need to bring everyone into that and we need to kind of paint this picture for them and point them towards it and be like, look, look at the pieces of this, that how we think about doing something. And you know, the aggressive way of saying it is you're indoctrinating a bunch of people. You're giving them this like religious, cult-like belief about what you do, how you do it, why you do it. And so then the moment you take your eyes off of their work product and the broader, you know, impact that they're making, you know that they are going and reiterating and re-indoctrinating new people in the organization. Everyone's putting checks and balances around how and why.
Wiley Jones [00:08:00]:
And that's fundamentally what culture turns into is like the founders believe have to get printed into the ethos of the organization. But it all starts with like, you know, for me it started with giving myself permission to let the company be an expression of who I am.
Matt Tait [00:08:15]:
Decimal is my third company and it took the third time for me to realize that. So kudos to you for doing it way sooner than I did. But I think there's an interesting caveat too of for us, we didn't write down our values until two years like when we'd finally gotten to the point where we had managers that were managing team members that I wouldn't see on a daily basis. That's when we're like, okay, it's time. It was also the point when I felt like the company had developed its own self expression where it wasn't just an expression of me and my co-founder Jacob. It had developed an identity that was, I would say, somewhat parallel but also unique in of itself because the more people you add, the more other personalities and other value systems come in and you want to use your core values and maybe some key behaviors as guardrails with the ability to kind of change and evolve too.
Wiley Jones [00:09:11]:
What I call that internally is, I describe a lot of that is like our operating principles. And there's like the, you know, Ray Dalio, the whole like, principles, and then you get like Netflix and like their culture documentation that I think has become very famous for, you know, we're a team and not a family and, you know, things like that. Finding what those are for your company is exactly what you said. It's an emergent property, is what I have found. And it's an emergent property that is, you know, like the first 10 people, let's say, in the company, you kind of have to hire them to almost think the way that you think. And then you bounce these ideas off of each other and you work on your product, you work on your go-to market, and eventually like the way that you do things and the people that you hire, it becomes really obvious, like what you truly care about. The Netflix one, I think, is the one that we look at the most in terms of thinking about how to formalize that. I think their statement about it is one of the most brilliant things, which is that companies values are not about those pithy things that you put on the wall of integrity or whatever.
Wiley Jones [00:10:12]:
It's about who gets hired, who gets fired, who gets promoted, who gets rewarded. Those are the things that determine your values. And that's one of the ones that we really pay close attention to.
Matt Tait [00:10:23]:
Yeah, I even boil it down to. Our values are how we treat people and how we interact with each other every day. And we write them down so that when we have new people, we can tell them what it means. And I think this goes to the Netflix principle of, you know, it's not just creating hypotheses or kind of cultural statements. It's having actual key behaviors that lead to success. And I think that's another important anchoring that a lot of companies don't do, is they'll have their values, but they aren't anchored in actually what to do on a daily basis. And I think that's the kind of key thing is everything that you do as a business, particularly if you're growing, needs to have an anchor. And behavior is how we act is what anchors that.
Wiley Jones [00:11:16]:
I was talking to a friend about this recently, and he spent the better part of his career at Amazon working inside of their category management and also product management. And this was like years and years after the company had started, obviously. And he's like, you could still feel Jeff Bezos's presence in every part of the company because you had category managers that were ruthlessly negotiating, really squeezing a lot of money out of their suppliers and vendors. Amazon doesn't need to do that functionally, you know, but they have this frugality that's baked into the organization. Well, how does that get baked into the organization? It turns out that people were rewarded and there were incentive structures that allowed category managers and vendor managers to be able to say, hey look, look at the money that I saved against, you know, what we had expected. And as a result, like my performance is being evaluated on something like that. And that's that anchor you're talking about. If you just say frugality is something that we value, but when people succeed or fail against it and there's never any impact as a result of that, like it's going to fall away.
Wiley Jones [00:12:19]:
It's, you know, it's going to go away. As soon as Jeff leaves the room, we think about that exact same thing. It's all about incentives.
Matt Tait [00:12:24]:
Well, and it's interesting for us, we run a remote company and that provides its own challenges. One of the things that we do is when clients give us testimonials or somebody gets a kudos or a prop from a boss or a peer, they always tag a value and a key behavior. And hey, this person, Wiley, did something awesome. Here's what it was. And it exemplified this value and this behavior. The other part of it too, and going back to your Bezos example, is it's also constant repetition and it's constantly putting that out in front and you know, now that decimals at almost a hundred people. One of the biggest jobs that I have is Chief Repeating Officer. It's my job to be constantly repeating stuff.
Wiley Jones [00:13:10]:
I have been persuaded because that's the thing that I think David Senra like the Founders Podcast, I'm not sure if you're a listener of that, but that it's one of my favorite things. Now he says that a lot which, you know, it's kind of funny that it's a self fulfilling thing. But that repetition is persuasive and I share that with everyone now because we do the exact same thing. And the thing that you described of like attaching a key value to shoutouts and to like customer wins, I'm definitely sealing that like starting today. So that's great.
Matt Tait [00:13:36]:
It was a learned thing and I had a story I've been, I've told people before of this was our first summer we ever had interns. We had this intern, JJ. I did an exit interview because I wanted to see like, is this something we should do again. Like, should we never do it again? And I asked him and about the, the role over the summer. And he goes, you know, I think I'm the only person going back to business school that could repeat all the core values of the company they interned in. That was my moment of, hey, this actually does work. And having that repetition because every time somebody gets a props or a kudos, you tag it. You guys talk about your values with clients. Like your values are something that like you all talk about all the time.
Matt Tait [00:14:20]:
And he goes, I don't think that's normal. And I was like, actually, it's definitely not.
Wiley Jones [00:14:25]:
We think about the spectrum of what you're describing. I know that a lot of large, large organizations also try to espouse values and print them into their company and they fail at it. And they're still kind of trying some of the same tactics. But there's a piece missing an example of this actually. My dad works for a very large public company. He's an engineer. It's one of those things where he's been there for a long time, he's worked inside of their ecosystem for a long time. And he said that at the start of every meeting, they actually like read off the company's values.
Wiley Jones [00:14:55]:
And I asked him, I was like, can you list me what those are? He's like, kind of not really. He couldn't really remember them. Right. And a lot of this is baked down into the fact that he's like, well, the reason is because they don't mean anything, like we don't really follow them. He has his own druthers with the company and all that. You know, over many years of kind of things going well and things going poorly. But I think about that all the time. I would imagine that a very large percentage of their company couldn't repeat the values.
Wiley Jones [00:15:22]:
Even though I know they repeat. You know, they say it at every single meeting.
Matt Tait [00:15:26]:
It's such a good point of how values are misconstrued. It's almost better to not have them than to do a crappy job with them. Actually, when I had my leadership team after a couple of years, I said, hey, it's time for us to actually write down our core values. And to do that, I said, hey, I want to give you three or four examples of company values that I think are really awesome. Let's talk about them. So I put up four different companies values and we talked about them and people were like, these are amazing. Here's what I like here. And then we paused and I said, great.
Matt Tait [00:16:02]:
These companies have all failed spectacularly. I had Enron on there. There was another one in our industry. Like, I paused and I was like, let's go to lunch. And we went to lunch, and we all talked about it, but it created this, like, oh, how do we do it differently? Like, what are we going to do? And it wasn't just about creating values, but it was locking in kind of what you've talked about and what we've been discussing is that anchor. Like, how do we anchor that into the company and make it so that it's something that every new employee, every intern, every client, they all understand, and it becomes a common language. Like, you talked about how, you know, you. You embraced your personality and the company being a reflection of your values and your personality.
Matt Tait [00:16:49]:
I think the next stage there is you create a common language, and if you have both of those together, then I think you have a great opportunity to create a growing cool culture.
Wiley Jones [00:17:00]:
Yeah, that's such a good way of putting it. It's finding the semantics that everyone can implicitly internalize. That's a thing that I talk a lot about with our team, is, like, the power of naming things and the power of, like, implicit understanding. This goes down to chemistry, where people, especially who play sports, you'll play with a player for many years or, you know, even, like, you're married or something, you can, like, look at your wife and, like, kind of make a face, and that's a whole conversation, right? And players who have worked together for a long time, they know, like, oh, I run this play, and he's going to be in the corner ready to take the three, right? Like, there's all kinds of things that emerge as you start to build chemistry. And chemistry is that implicit internalizing of the semantics of what things mean. You know, when I can say to a team, I'm like, hey, is this thing ready? I can just say a short sentence like that. And they know what ready means to me. They know what ready means to the organization.
Wiley Jones [00:17:55]:
That it doesn't mean, oh, the slide deck is done. It means that we've done an extreme amount of scrupulous preparation so that when we go and present to our customers, they're not going to have questions about this broad class of things that we. We expect to have dialed in. Right? But those are the kinds of things that you have to set, you know, and correct. When someone deviates from what ready is supposed to mean, you go, guys, this is not ready. Ready to Doss means X, Y, and Z. Every day you're calibrating those things.
Matt Tait [00:18:23]:
I think if you're going to do any of it correct, and you Just hit on it right there. Accountability is so important and it's understanding what is being accountable, how to hold people accountable and how to improve and learn from when you're held accountable. And I think that's really, that can be hard to do.
Wiley Jones [00:18:45]:
I think it's extremely hard because the organization a lot of times is not set up to even enforce accountability. This is not like a really a broader commentary on like the state of how. I think a lot of workplaces maybe have gone a little easy on people or whatever and not, not trying to make that like a broad categorical statement. But my wife actually recently moved from a startup where we actually met and we worked together. We went and saw, you know, from that company growing from a hundred people to now multiple thousands of people. When we both were working there, they went through a massive growth trajectory and they maintained a lot of intensity. And now she actually moved and she now works at a public company that's much, much larger. And the thing that shocks her and I've overheard some of her calls and things like that is like people miss deadlines, people will fail to live up to the expectations set by their teammates and the managers go, okay, sounds good and they just move on.
Wiley Jones [00:19:36]:
Her and I have talked about this and we're like, why is it that, why is that like that? Because the management team is not rewarded and they're not incentivized to hold people accountable for things. There's no structure by which they can do it. There's not really any reason to be the bad guy and to come down on people when they don't deliver on what they're supposed to deliver on. It's still just about like top down values. Like are those things being anchored to some level of incentive or some kind of thing that exists in the real world. That's a process that enforces people to be accountable.
Matt Tait [00:20:06]:
Something that I've learned is it's also our job as leaders to enforce culture and to do the hard things and to set the example. I have two examples that I think stand out to me and I'll be interested in some from you. Number one is I talk a lot about my failures, about what I failed at, what I've screwed up, because I want to normalize failure in the company because one of our values is to move fast and make things better. If you're going to do that, you're going to fail and that's okay. But I want to normalize that failure is okay. And in order to do that, I talk about how I screw up frequently. And to be fair, I have a lot of examples to come to pull from. The other thing is I have a coach.
Matt Tait [00:20:55]:
And one of the things he pointed out when we were first, and this goes to the accountability to tie it together when we first started working together, he goes, you are a conflict avoider. And I said, there's no way. If I got a problem with you, I guarantee you and I are talking about it. He goes one to one, you to somebody else, you are not a conflict avoider, but as a boss, you're a conflict avoider. And I asked him what he meant, and he said, when two people that report to you have a problem, what do you say? And I said, I tell them to go fix it, go figure it out. Like, guys, you have a problem with each other, go figure it out. The problem is nobody does that. Nobody actually goes and figures it out.
Matt Tait [00:21:31]:
And he said, if you want your organization and your company to be healthy, it's your job as a leader to not avoid that conflict, but to actually pull them into it. And hey, you can give them the first, like, hey, you guys, go figure it out. But if in two hours I don't have a solution and you guys haven't worked it out, you're coming to meeting with me. And I now run a conflict process of what's going on, how are you feeling? What are you doing? How do we solve this? And it's created that level of accountability because your situation with your wife and her examples actually highlight conflict avoidance, where nobody wants to dive into that conflict or that accountability, but it actually creates conflict with people like your wife who want to be held accountable and see others held accountable, and they spend enough time there to, you know, give her 10 years there, she'll stop wanting to be held accountable because nobody else is.
Wiley Jones [00:22:23]:
The deviation from what she expected as the norm is, which is, you do a job, people, you communicate what you're going to go and do, and you execute against that. And, you know, if you fall short or go above, people recognize that the deviation from that standard is really, really fast. Like, it just completely falls off a cliff. One other interesting thing I saw also at kind of a growing company previously that I was at was that when management teams become a conduit through which conflict is resolved. And it's not a group activity, it's like, oh, just run it up the chain. They'll figure it out and they'll come back down to us. That gets really dangerous because what you're doing is you're removing people from that conflict. Resolution process, then people just say, oh, if I don't know how to do something or I don't like, want to deal with this other person and do things myself, I'm just going to run up the flagpole and they'll figure it out.
Wiley Jones [00:23:12]:
Management will figure it out. People look at that as like, oh, we're really good at avoiding conflicts and resolving conflicts, but you're removing individual contributors from so much of the decision making process. And that's a huge problem too.
Matt Tait [00:23:24]:
You have to trust and empower your team. And if you're going to grow as an organization and be successful as a CEO and as a leadership team, you can't do it all. Fundamentally impossible. You will break. And so you have to develop that empowerment and trust. And I actually had a situation this morning where my COO was caught in meetings. And so one of our sales team members had an issue and wanted some help. And he had already come up with his first solution because kind of like you said, my biggest thing is go solve it yourself and then tell me how you did and do you have any problems? He had gone and solved it himself.
Matt Tait [00:24:05]:
And so we talked through. He had this client that came and I was like, number one, did you ever call him? He goes, no. We were texting and I was like, so you never called him? He goes, I should have called him, shouldn't I? I was like, yes, this is definitely a nuanced conversation. Text messaging, not good for nuance. And he was like, yeah, I was trying to do quick. And I was like, look, what happened was you were flying in a plane, you saw a fire and you jumped out. At some point you realized, oh shit, I could have let the plane land and still put out the fire. You needed to like pause and take some time and have the conversation.
Matt Tait [00:24:37]:
I told him, I was like. He goes, well, what would you have done? I told him, he goes, that's way easier. And I was like, I know. Then I was like, you would have gotten there too, but you decided, hey, fire, I'm jumping out of a plane.
Wiley Jones [00:24:48]:
You know, when we look at hiring people, I think there's kind of like three things that I look at a lot. It's the quality of someone's judgment. That's performance. At the end of the day, if someone is a high-performing person, they make fantastic judgments. They're not wrong. Almost ever. You look for high-intensity people who have a bias for action and they go very quickly towards the problem. They're, you know, they're heat-seeking missiles and then people who are high integrity.
Wiley Jones [00:25:14]:
And when you combine those three things, you get this like, person who's extremely collaborative. They work really hard, really fast, very effectively, and that's great. But if you drop any one of those three things out, you have a huge problem on your hands. It's basically a toxic workplace at that point. What I think you're describing here is someone who, in this example, they did a great job of like moving with intensity and with force and having that bias for action. But the judgment piece, like, they just didn't balance it correctly. You know, it's like when you look at leveling people up and I'm always thinking about how to bring people on our team to the next level. I'm like, look in those three areas, like, you just made the wrong judgment.
Wiley Jones [00:25:49]:
You, you approached it with enough urgency, but you did X wrong. There's very no room at all for like low integrity. But sometimes, you know, that comes back to judgment. Sometimes it'll be like, hey, I know you didn't realize this is what you were doing, but this is what you were doing. Right? And that's why we can't have that. It all kind of ties back to that. The values being the substrate for which you look at hiring people, you hit.
Matt Tait [00:26:08]:
The nail on the head. And one of the biggest things I talk to the team about is ironically, I do the same thing with my kids. Slow is smooth, smooth is fast. And like the reality of any major problem, a deep breath and a lap around the house, it's not going to change in that few minute period. But what that'll do is it'll give you the ability to like reset and mentally get out of like the fight or flight mentality and into the like, think and consider. Because people that have too much of a bias to action, they do the ready, fire, aim. And what you really need is people that are totally cool with ready, aim, fire. And that can be a hard thing, particularly in hiring.
Matt Tait [00:26:49]:
And then coaching is like, hey, speed is good, accuracy is better. So let's index towards accuracy and then speed. They're both important, but in that order is way more important.
Wiley Jones [00:27:04]:
A hundred percent. The thing that I always come back to thought process-wise is I'm like, what you just described is valid for 99% of businesses and to 99% of people or probably even more than 99%. But it's not a hundred. You know, it's like if you're working truly in like you're in an operating room or an emergency room or you're in the military or you're, you're literally having to make split second decisions, then I have no advice for you. You're on a different level than I. But we're building businesses that a lot of times it's not life or death. And so the ability to take 30 seconds, walk over your coworker's desk and be like, hey, I just got this message, what do you think? And, and they can go, oh, you need to call them, or don't even worry about it, I'll handle it, or whatever that is, that, that collaboration, there's pretty much no scenario where if you are running into something that is concerning or confusing, where you can't just bring one other person at least into it, it's not life or death. It doesn't need to be split second.
Wiley Jones [00:27:59]:
That ready, aim, fire. Like the aiming a lot of times I think also gets missed in that process because people don't immediately default to doing something collaborative because they're like, oh, I have to get it fixed right this second.
Matt Tait [00:28:12]:
The irony of the slow is smooth and smooth is fast statement is it actually comes from special forces.
Wiley Jones [00:28:19]:
There you go.
Matt Tait [00:28:20]:
Where it is truly life or death. It can work for them. And part of it is they build the training, they build the habits, they build the workarounds, they build the collaboration. And when you apply that to our jobs, you're exactly right. Like you can take the extra time and it's fine. You can still be hyper-responsive by responding in 30 minutes versus 30 seconds. And that I think is an important thing to consider. One of the things I'm interested in, because as you guys are growing, you're kind of reaching a point that I've always found to be hard.
Matt Tait [00:28:55]:
And that is as you kind of grow in scale as a company, as a CEO and as a boss, you end up having to look at yourself and say, hey, here are the things I'm good at. Here are the things I kind of suck at. You have to hire for your deficiencies, which is also kind of part of being able to look at yourself and say, I have deficiencies. How is that process of growth and as you guys are kind of evolving, how's that going for you?
Wiley Jones [00:29:24]:
There's also a natural point which comes from the fact that I have a co-founder and I think it's very different if you don't have one. So I'll give my answer of like, as someone who does have a co-founder, we are two sides of the same coin. We're not polar opposite people, but we have very different biases towards how to accomplish things. And it's finding this foil for yourself that I think is extremely important. Frankly, a lot of that I have in my co-founder. Now there's like, areas where both of us have deficiencies in aggregate, and then we have to go in and look for hiring in those areas. And that's something that we really pay attention to.
Wiley Jones [00:30:02]:
But the very simple example is I am a long term, like, what do we need to be doing to set ourselves up to succeed over the next few years? What are the things that we needed to be directionally pointed at so that, yes, this first version of it sure, get it out the door, but the second and third versions of it are flawless. Right? Like, those are the things that I'm thinking about. And a lot of times my co-founder is like, hey, but like this thing we need to get out the door because our customers need X, Y and Z. Right? Having a person who can either ground you and bring you back to earth, or if you're the person who's grounded and brought back to earth, having someone who can 10x, 100x your ambition, 10x, 100x. The scope and scale in which you're thinking about something, you have to have those foils. And a lot of times it just comes in the form of, like you said, strengths and weaknesses. My co-founder and I are both extremely intuitive thinkers. We're not really analytical.
Wiley Jones [00:30:50]:
And I say analytical as in, like, him and I are not people who are going to go and look and be like, well, this did 63%, you know, better and this other one did 48% better. Him and I are like, let's internalize a lot of stuff and let's make a call. And as we grow as an organization, we're going to have to fill out the company with a bit more analytical thinkers. Because when you get to a larger scale, being analytical is extremely important. When you're a small company, being intuitive is important, you know, in terms of like, kind of how you lean and how you index. And so those are the kinds of things that we have to pay attention to. But it's also, you have to sequence it in time. Like I said, finding that analytical personality at day one, you know, when there's 10 people in the company is very different than when you're a public company and everything has to be flowing through this analytical set of inputs.
Matt Tait [00:31:35]:
No, I think that's exactly right. For me, it was. I hired a COO a couple of years ago, and Michael would tell you it's his job to run the business I needed somebody that was that manager of execution that could run the day-to-day company. Because I always joke with people. I'm very good at convincing people to jump off a bridge. I'm very bad at getting them to line up to do it. And so I needed somebody that could line everybody up, get the processes in place and really build that kind of side of things in the business. One of the things I found has also been hard in this kind of adding new skill sets and stuff is you and your co-founder, both are more on the technical side.
Matt Tait [00:32:21]:
And so how has hiring people on the soft skill side more selling like sales and marketing, how has that gone in terms of adding that to your guys kind of quiver of arrows?
Wiley Jones [00:32:34]:
Fortunately that's actually something that I have internalized pretty early on. I worked at a company previously that I would describe as a world-class go-to-market organization. They have one of the best demand gen and sales functions I would say, in any tech company in the world today. Like they're in the top 50 for sure. And that's a hard thing to accomplish. So when I got to see that happen, you know, at scale where this company is now getting close to making $1 billion in top line a year, and I saw it when it was like below 10 million and seeing that growth, you know, of how they went through that process, it made me realize that I needed to obsess over all of the inputs to that machine. The same way that I obsess over product. Approaching go to market with the same level of curiosity that I approach product with has made it a little bit easier.
Wiley Jones [00:33:27]:
But there are things where the easy answer honestly is you kind of have to just test stuff and see what happens. You know, you'll, you'll hire a salesperson, you go, okay, how good are they at like X, Y and Z? And you test those things and you go, okay, they're good at this, they're good at this and they're really bad at that. Is it this person or is it that like this broad class of people who kind of think this way are bad at this? Or is it that I have the organization set up in such a manner that we're not giving them the things they need to succeed. And it's like you're peeling away all those layers and approaching it very experimentally. And that's just learning. At the end of the day, I think I've kind of approached the same way I approach everything. Just extremely curious, trying to find patterns to match against, experimenting, seeing what the results are like, and trying to be as thorough as possible in evaluating where the fundamental properties of things emerge from. You know, is it the person, is it the process, is it the organization?
Matt Tait [00:34:19]:
Well, pro tip, all salespeople every time are really bad at entering information into a CRM consistently.
Wiley Jones [00:34:26]:
We've got some fun hacks for that already where we've actually been able to have kind of a remote team that helps us on like sales operations. And that's been a huge level up for us is just being able to take a lot of the administrative burrs the same way that, you know, CEOs and founders a lot of times will have like an executive assistant finding ways to build a sales operations part of our company that they're really focused on the minutia and there are people who are excellent at it, the same way that a salesperson's excellent at doing discovery.
Matt Tait [00:34:53]:
We're getting close to the end of the year. This will come out of the beginning of the year. But I'm interested for you personally. I know a lot of people are probably asking you now like, what's the forecast, what's the budget, what's the company looking like for the next 12 to 36 months? But you personally, what's your level up and what's your goal heading into next year?
Wiley Jones [00:35:13]:
I try to be as much of a like, continuous person as possible. You know, instead of thinking like this quarter we're doing this next quarter we're doing that. I'm more like as of today, what did the next six months look like? I would say the end of this quarter and into the next quarter. On the tactical side, like we've really focused a lot on demand gen recently as a company. And that's been one of the things that I've been the happiest with is how we were able to make a bunch of assessments and hypotheses about what happens when we go and really invest money in spending on generating demand, getting people into our funnel and then seeing how they convert. You know, you have to kind of spend money in demand gen to run experiments. You can't really run them for free like you can maybe in some other categories. And so we were pretty meticulous about saying like if we spend X dollars and we generate Y qualified pipeline, that's a great signal.
Wiley Jones [00:36:06]:
And there will be about a three to four-month lag in where we'll start to see that. And now that we are seeing that uptick, now we're evaluating other parts of that entire funnel and that entire customer lifecycle. We're saying, okay, where's the new bottleneck? We have a bunch of qualified pipeline. How are we converting people? How are we qualifying them? Oh, it turns out we're overqualifying. We have a really high qualification rate. That means we're still probably, we have more pipeline to build, like, you know, and trying to find those set points, that's been a big focus for us in the last few months. And then seeing now how that'll play out down funnel is, I'd say over the next, like quarter or two quarters is something that's going to be really interesting. We currently have one account executive we're going to be bringing on more probably in mid next year.
Wiley Jones [00:36:48]:
Turns out, you know, between myself and that one account executive, we've been able to actually get a lot of efficiency out of just the two of us. It's just kind of things where we figured out how to split up work people are doing, where a lot of our implementation team, they're taking on a lot of what down funnel selling normally looks like. And so the account executive doesn't have to be as involved. And so being really present in that loop myself has allowed me to be, I'd say, accurate in how we instrument new processes. That's the phase that we're in and I think where over the next six months, stuff that I'm really paying close attention to.
Matt Tait [00:37:22]:
One of the key characteristics of successful founders is their ability to evolve and adapt. How are you looking to evolve and adapt yourself?
Wiley Jones [00:37:32]:
I think my journey for a very long time as a founder is going to be about balancing the inherent skepticism I have for my own ideas and the inherent conviction I have for my own ideas. You know, if I think about, like, what my journey is going to be building this company, it's going to be in how I reconcile those problems on a daily, weekly, monthly basis where I'm like, are we really doing the right thing or am I just telling myself this story? That's a really big thing for me. And it down to even how we like, okay, you know, finding the right people to go in and level them up. And right now we're. We're still a flat company, very flat. We don't have any middle management. At what point do we need middle management? And that's me, you know, convincing myself it's fine, I'm doing it, I can keep doing it right. Those are those kind of, you know, ideas that come hard in conflict with each other, to be honest.
Wiley Jones [00:38:18]:
And the next big part of that journey is how the company building and building our first management layer. That's going to be a really big challenge for us next year because we're still flat. And then honestly, personally, my wife and I are expecting, we have our first, we're going to have our first child. Congrats. Early this. Thank you. I really fundamentally believe that you can have it all, that you can, you can have everything you want in life. And the same way that I have to ruthlessly prioritize with the company, I'm going to have to ruthlessly prioritize in my own personal life that I want to be a present parent.
Wiley Jones [00:38:47]:
I want to be the best parent I can, the best partner I can to my wife. And finding new ways to unlock more profound impact in the company and in my own personal life and being present with my family and with the company at the same time, that's going to be a huge challenge. And I know that that's the thing that everyone talks about as founders is a big part of the journey is finding ways to balance yourself and your whole life. That's going to be a big thing for me as well next year.
Matt Tait [00:39:10]:
Well, congrats on baby number one. I have two 10-year-olds and an 8 year old and I miss the stage when they can't move and talk. It's a great stage.
Wiley Jones [00:39:19]:
Yeah, that's great.
Matt Tait [00:39:21]:
But what I would say is, let me add something that every founder hopefully gets to give yourself grace because you're going to suck at all of it at some point and you can't be great all the time at everything. But that's just life. I, I've learned that myself is sometimes I'm really great as a boss and I'm really great as a dad, but I'm struggling as a husband. Other times I'm great as a husband and I'm great as boss. I'm struggling as a parent. And it's always constantly moving. It's kind of like go-to-market fit. You have three moving targets now and you're going to have to constantly be recalibrating how to hit them all and bullseye.
Wiley Jones [00:40:01]:
Yeah. And it just comes back down to that thing that we tying it all back to full circle. It's just about values at the end of the day where like, you know, you have to learn to say no to things that are now no longer in that set of your values and say yes to things that align in a new way where, you know, like I might have bent over backwards and spent 100 hours in a week doing a certain thing for a set of customers. Just to delight them that extra amount. And now I have to learn how to delegate that to other people because, you know, I have a an 8-week-old or something. I can't be doing a hundred hours this week. It's not going to be physically possible and it's probably not a good idea for anyone. And so how do you do that? Well, it just comes back down to values and like finding ways to level people up to scale back the things that no longer make sense for yourself and for the company.
Matt Tait [00:40:52]:
It's hardest for a CEO and co-founder. A hundred percent. Everybody else it's hard for it is harder. As the CEO and co-founder, I am excited for the journey. I'm excited to watch how you guys keep just growing and I really love your intentionality about culture and Wiley. I really appreciate you coming on to after the First Million and look forward to just continuing to watch.
Wiley Jones [00:41:17]:
Thanks, Matt. Really appreciate it. This has been great.
Matt Tait [00:41:20]:
Thanks so much for listening. After the First Million is presented by Decimal. To listen to more episodes and find tips to help make running a business easier, visit decimal.com/afm. Want to join the conversation? Reach out to me on LinkedIn and let's explore the messy middle.