From Hustlepreneur to CEO: Tyler Robertson of Diesel Laptops

In this episode of Know to Grow, host Chandler Kohn sits down with Tyler Robertson, founder and CEO of Diesel Laptops. Tyler shares how he bootstrapped his business from selling diagnostic tools on eBay to building his company. He opens up about scaling challenges, near-death financial moments, leadership evolution, and the strategic pivots that fueled Diesel Laptops’ growth.

Tyler Robertson: Well, first of all, I love the name of the podcast because heavy duty is what we do, right? So heavy duty commercial trucks and equipment is what diesel laptops does. And where it started with just like selling diagnostic tools, it’s really transformed into us being a solution for technician efficiency. So what dieselaptops does is five things. Number one, diagnostic tools like the Amazon and diagnostic tools. Everything from little Bluetooth cold readers to like these ten thousand dollar level dealer level tools. Tools only tell you what’s wrong, they don’t tell you to fix it. So we built the Wikipedia of parts and repair information there. Now you can have your wiring diagrams, your step by step and all this other information you need off the diagnostic tools. We also built a call center staff with diesel technicians for the old phone, a friend. And we have online learning and classroom training centers throughout the United States. We teach diesel technicians how to properly troubleshoot. And we recently acquired another company about five or six months ago that does 24. 7 remote monitoring and predictive AI. So we’re doing what we do in the shop, but we’re going to move it into the in cab and in the cloud essentially. So our industry, like every other industry, is constantly evolving and changing as time marches on here.

Chandler Kohn: Excellent. And who was, who was the acquisition?

Tyler Robertson: Yeah, the company’s called Pretact. So just to like give the audience a little background here, there’s really three companies in North America that did predictive AI for commercial truck. So this is for like before your tire blows, before your brakes are going to fail, like those types of things. Predict was a really hard thing to sell because at the end of the day you go sell it to a business and the other business has to justify why they’re spending these hundreds of thousands of dollars a year and where’s the ROI on it? And when you can’t prove there was a, an actual roi, it’s really difficult sometimes. So all these companies have been struggling and pretact is the same situation. They had a couple nice accounts, small company upstart, a couple million in revenue, and they weren’t getting the renewals. And a big, big customer is a big part of their customer base decide not to renew. And they were kind of like caught in a hard spot. And we, we swooped in because I wasn’t, I didn’t want to buy a predictive company. It’s not why I did it. What they had, what they didn’t, what they didn’t realize is what they had was the ability to do 247 monitoring on commercial trucks. And they had, they already had their diesel technicians in their call centers. So they’re using AI in humans to diagnose these problems, either reactive or proactive. And I was like, man, this is exactly what we want to do here at Diesel Laptops. We want to have it. So now, like, the way the world works today is trucks break down and then it’s all reactive and we’re sending people out to them, we’re towing them places and doing all these things. So now it’s like, well, why can’t we just diagnose these things as they’re driving down the road or when it first happens? If we can even do that before technician arrives, we can at least give a whole bunch of knowledge to the fleet manager, the repair shop, everybody involved to get that thing back on the road quicker. And that’s where we’re going. And it’s been going great with them ever since. We, we actually just last, this last week signed, signed a million dollar deal with the company for monitoring. So it’s.

Chandler Kohn: Congratulations. Yeah, well done. Yeah, I think four or five years ago I had spoken with some of the pre tech folks, but it’s been quite some time. And how many employees do you have now, including 200ish.

Tyler Robertson: Yeah, we hover on that 200 level.

Chandler Kohn: Yeah. Good, good. Well, let’s, let’s hop into it. You know, I think there’s going to be several parts to this podcast. You know, this is about growth, Tyler, as you know, and you are a great example of, you know, entrepreneur, you know, your entrepreneurship. I want to really dig into this and kind of discuss how you went kind of from a hustlepreneur to a real CEO managing $100 million company with 200 employees all over. So let’s talk about the kind of the spark. In the early days, obviously you saw a gap in the market. Tell us a little bit about the original idea and how that came to Fruition?

Tyler Robertson: Yeah. Well, the original idea was, you know, I’m in my mid-30s. I think I’m like most people that are married in their mid-30s and got crushing on a debt on you. You have house payments, car payments, student loans, just. Just everything your life’s going on. And I was the same way me and my. My wife were, and I just want to get out of debt. So I started trying to find ways to make money to. To get out of debt. And because I worked in commercial truck dealerships and essentially my whole career, I knew there was some demand there for some things. So literally my first couple products, I had nothing. I just found other people’s products, bundled them up, put them on ebay, and sold them and was making some good money doing it. And eventually I had to make a decision between staying with my current employer or going out on my own. And when I really looked at the risk, it made a lot more sense to just go try this thing and see what could happen in. So those early days was just me in my garage, my dining room table, and it was like, hey, let’s just go. Let’s just put a roof over the head, over our heads and make sure there’s food on the table for everyone to eat every day and start there.

Chandler Kohn: Were you a bit surprised that there was a gap in the market and that there wasn’t a current solution? Would you actually do this?

Tyler Robertson: So I knew there was demand, right? So I worked in commercial truck dealerships my whole career. I worked as a service manager, parts manager, IT marketing, truck sales. Like, I’ve been around commercial trucks at a dealership repair level for over a decade. And through that time, you talk to a lot of people and you start to get. You understand what’s happening. I know really well what happens when a truck breaks down, but I have no idea how freight moves from point A to B. Like, that’s not my world. But I understand this world. And in the commercial truck space, the big part of it is there is no right to repair. So in automotive, we can all go online, we can go buy tools from Amazon, we can do all these things, and there’s right to repair, which allows us as car owners to be able to work on our own stuff or bring it wherever we want. Essentially, in the commercial truck world, that’s still not a thing. There is no law. There’s things in legislation, they have been for years, but there is nothing there. So now you have OEMs that don’t have to share information, they don’t have to Give training, they don’t have to give you access to look up your own parts, they don’t have to give you access to repair manuals. And now you have these $100,000 capital assets driving all over the country and they’re breaking down. And new technology with the emissions came online in 2004. Nobody knows how to fix them. So all of a sudden now you have a bunch of demand because people just want to fix their stuff and keep it moving. And by the way, dealers are backlogged two or three weeks or four weeks in service work. So now all of a sudden you’re put in a really poor position when you’re an owner. So demand, demand was there. The market was just waiting for some opportunities to come along and for people to start executing on it.

Chandler Kohn: And then let’s talk about the first kind of growth catalyst. You had an idea there was a solution that the market needed. What was the first real growth catalyst for the business?

Tyler Robertson: Yeah, so what I like the old way used to be, hey, if I have a Cummins engine, I buy Cummins software, I have a Paccar engine, I buy paccar, and so on and so on and so on. And what happened is, is about 15 years ago like the multi brand tool started to appear. So that very first product that I got that I was selling on ebay, I was buying some guys all makes read everything software. I was buying a laptop from somewhere else and then buying the hardware from someone else to connect, connect the two. And that’s when we started seeing the dawn of like these aftermarket all make, all model multi brand tools. And when this happened like 10 years ago, when I was doing this 10 years ago, and I told you, man, I got one tool you can hook up and read everything and do everything a dealer can do, they’d say that’s impossible, that doesn’t exist. And I’d be like, well no, here it is, it does exist. And repair shops wanted them. Repair shops, they wanted to work on every make model, take care of their customers and never say no to a customer. So our customer base when it first started was independent repair shops. And these guys were just begging for something, anything at all. They were using bootleg software, they were borrowing tools from dealer, they were doing whatever they could to get access to hook up to these things, to figure out what’s going on. And all of a sudden we came along and we’re like, well, here’s not just one option, but here’s a couple options, like how much functionality do you want and what are you willing to pay for it? And that was like the early days. It was just like as fast as we could get the word out of there. I was selling stuff. It was great back in the day of how easy it was because people didn’t even know such a tool existed and all that to say it’s been going on now in another industry that’s parallel, that’s the off highway diesel world. So again, in that world that people know like John Deere and right to repair and how much John Deere doesn’t want people to work on their own tractors, there’s headlines all the time about it. Same thing. People don’t believe there’s aftermarket tools that can do what the John Deere software does or the Caterpillar software, the Kobelco software, but yet here we have it and here it works.

Chandler Kohn: Interesting. So you were generating some revenue, but obviously there was product development needed. You know, you had a solution that, that, you know, there was a gap in the market. Right. But how, how did you think about bootstrapping and, and you know, maybe taking on a little funding to, to really grow this thing quicker?

Tyler Robertson: Yeah, I didn’t, man, in those early days, those first couple years, I, I just told people I was like too dumb to know any different. I was just like, you know what, I, I live, you know, very modest. I need to take all this money and just keep putting it back in the company. So I didn’t take any disbursements out of the company. I think for like seven years I just kept it all in there. So every time I made a profit and I had, I didn’t have a choice because the company was growing so fast and we were growing fast. Inventory, receivables, R and D and then taxes on top of that, it just like piles on and it’s really freaking difficult to grow. And there were some like hairy moments in there. But on the other hand, I was always debt free. So I was like, okay, I’m not going to have any debt. I already paid off my personal debt. I learned that lesson. That was tough. Let’s try to not take on debt and try to go do this thing. So yeah, we had a bank credit line and we’d hit it once in a while if we got in a jam. But for the most part I was just growing as fast as my cash would let me grow. I think if I took on investment money back then, I probably could have been growing faster. But then I also wouldn’t be sitting here today with, with my equity that I have and have a company this size. So, like, it turned out well in the long run, but in the short term, yeah, it was, it was painful there. And you just got to believe in the long term vision and believe where it’s going. But I, I had never raised money. I was a service manager and parts man. I didn’t, you know, I work with somebody else. I don’t even know how to do that. If I wanted to do that at that point, it was just like a foreign concept to me.

Chandler Kohn: Yeah, understood. That’s helpful there. And then you mentioned vision. Let’s talk about vision versus kind of market feedback. Did you ever have to. To kind of try to stay balanced versus what you think the market needed versus kind of what it was responding with. Did you ever have to pivot or were you kind of always on point?

Tyler Robertson: No, I mean, we’ve pivoted like a hundred times. Right. So like, you. So it’s, It’s. I’ve been in this industry forever, and some of the people I hired were also industry people. And my first couple hires were all people from the industry. So we all knew what the problems were. Like, we could sit there over beers and, like, complain about everything. Like, we knew the customer pain points. So it wasn’t like I was coming from the other side where you see a lot of startups where it’s like, I’m a software engineer. I know nothing about this space. I’m gonna raise a couple million dollars. I’m gonna build a solution. Like, in, in my industry, I’ve seen that try to play out several times, and it seems like it never quite works out because they don’t really understand what the customers want or what they’re willing to pay for it. So, yeah, yeah, it’s. And it’s a constant. It’s a constant pivot. But I’ve never. We don’t do like, customer surveys or asking like, what would you want? Or what would you. What do you think you need? Because we feel like, well, we deal with this every day, especially now. I mean, I employ 50 diesel techs in various roles here at the company, so. And our senior executives are from dealerships and repair place. Like, we understand this space really well, so we get the pain points and we talk to enough customers to keep understanding it. So for us, it’s still the constant. The constant. We got to innovate and we got to be better. Because I’ve seen it happen too many times. I mean, I did it to my. Like, I, I was the smallest guy with a little credit eBay. Store selling stuff on the back of my trunk and there was another company doing 30, 40 million in revenue and we Blu ray buying. Right. So I’m like, okay, if I don’t change and constantly innovate and constantly come up with new solutions and better ways to do this, we’re going to be those guys that just get our door blown off by the next upstart.

Chandler Kohn: Yeah. And we’ll get into this in a few minutes on how you actually implement some of that feedback and you know, the communication between your customers, you know, product, market fit. You know, when you were in the early days, you know, I’ve been talking about metrics with a few people in terms of growth because it’s kind of hard data, immediate feedback. That data can sometimes guide you in the right direction. Did you have any metrics that you were paying attention to?

Tyler Robertson: I mean, back in the early days, my bank account, right. That was the, that was the big one. But for the most part I just got so focused on top line revenue growth. Like I was just so focused there, you know, for good or for better, for worse. I was like, I’m going to focus on two things, sales and marketing, and we’ll figure the rest out. And when you do that, you do leave a lot of, a lot of dead bodies, so to speak, behind you. HR, accounting, tech support, customer service. So those early days, I went from three and a half to seven and a half, to 16, to 32 to 50, something like in a heartbeat, just over a span of a couple years. And that all caught up with us. Eventually a lot of bad things happened. People stole from us, had employee fraud, customer fraud, credit card fraud, all those things that happen when you do that. But we just gave up. We just sacrificed it and said, we’re going to go, we’re going to go after this top line revenue growth. And that was really the KPI that, that we focused on in the early days. But it changed. Then it got into like retention and now we do more strategic planning. So things just change as your company evolves and the size your company evolves.

Chandler Kohn: Yeah, you know, this industry, we see a pretty low customer concentration. And you know, I think I have a good question would be, is, you know, how is your, you know, customer acquisition strategy shifted from, you know, your first hundred customers to now your, your, your, you know, your next hundred to 300 or 100 to, you know, 400. How did you change that?

Tyler Robertson: Yeah, it’s constantly. So back in the early days it was, it was real simple. Like I, I was like I’m gonna own, I’m gonna own the Internet. So every week when I was my early days, I would literally sit down and be like, I’m gonna do at least one meaningful thing for SEO and I’m just gonna own this space. I don’t have outside sales rep. I’m getting all my traffic through the Internet, so let’s go position myself on there. So blog posts, getting on page, SEO, getting backlinks, just doing all the things that you want to do to make sure your site ranks. So in those early days, like, and we did paid search, right? So the early days we did paid search and we were bidding on our competitors names, our competitors products, just so I get the phone call so I can convert them to like what I was selling. Today it’s different. Our most expensive keyword we bid on is our own, our own name. Because we position ourselves as the experts, we get over, you know, like I said, it’s a small space, yet we get over a million unique visitors a year coming to DieselLaptops.com trying to find an answer to a problem they have. So we position ourselves really well there. But marketing constantly has to change. So before it was just like market this thing and just market it to everybody and just do the shotgun thing. And now it’s shifted. Now it’s like, okay, well now we got customer Personas. This guy’s a diesel tech, this guy owns a shop, this guy’s a repair tech, this guy owns a fleet. This guy owns a fleet with multiple locations. This guy’s enterprise, this guy’s, you know, it goes on and on and on. And what we’ve learned is, well, those are all different marketing conversations. So marketing points and those are all different sales conversations. So we have to, we have to change how we go to market, how we talk to customers and how we put them through different sales funnels, the marketing funnels to keep driving them back to our website. So it’s definitely a fun challenge. We definitely have a lot of, you know, several, several really good marketing people over here and companies we use to do these things. But at the end of the day, you just gotta, gotta keep getting your name out there and keep repositioning yourself so people understand the value you bring to the market. And probably the biggest pivot that we’ve had to make is before people just cared about a tool. Now it’s not just a tool, it’s, well, I need the repair, I need the training, I need all these other things. How do we sell that against someone that’s Selling just a tool. So having products and having solutions is just different conversations. And trying to convert an entire salesforce to talk about a solution instead of a product is a difficult thing at best.

Chandler Kohn: Yeah. And then want to talk about SEO for a second? You know, I have a client in the space, it’s very niche in the heavy duty side and they are organically ranking they, they don’t have an SEO consultant. That’s great. I mean that’s the ultimate goal. You know, your website looks pretty robust. A lot of pages, probably a lot of backlinking. Do you have keywords that are kind of organically ranking themselves now or is it just a constant focus?

Tyler Robertson: Well, from day one when I decided to name the company Diesel Laptops, the only reason I did that is I did the Google keyword research and realized those are the two most common things that people are searching for for my product. So like, oh, Diesel Laptops it is. So we’ve been conscious since, I’ve been conscious since the very beginning making sure everything was done properly with keywords. Blog blogs. I mean a lot of people think blogs are like to share information to customers. They’re not, they’re to like rank keywords to get traffic to your website to convert.

So in a lot of spaces it’s not that competitive and you can actually rank pretty fast if you just do some basic one on one things efficiently. But for the most part, yeah, organic is obviously the holy grail. Right. Free traffic off the Internet. But even now that’s changing with, with generative AI. So a lot of companies are already seeing their organic drop because generative AIs aren’t referring them. So a whole nother industry cropping up there. And Geo, there’s a couple of names they call it now, but it’s the next frontier.

Chandler Kohn: Early in the days, what were your key strengths and what were your weaknesses and were you aware of those?

Tyler Robertson: Yeah, in the strengths. It was just, look, I’m an entrepreneur, I’m a go fast guy and I’m one of those guys that’s like never, never happy with, with what we did yesterday. Like we can always do better. It doesn’t matter what it was. Right. So when you do that, that’s obviously a strength and a weakness because it focuses me on sales and marketing. But like I said, we had all kinds of not good things happen on the back end. I know customer satisfaction fail. I know tech support fell because we’re taking our customers. We were just growing way too fast on the top and not fast enough in the Middle there. And we stumbled on ourselves quite a bit through that entire process. And even looking at it today, we definitely still have our challenges when it comes to growth and comes to taking care of customers and doing some of these things. It’s one of those things you just constantly have to be looking at, paying attention to and making sure you’re doing the right things to keep growing the company and moving it forward. Yeah.

Chandler Kohn: In terms of your product roadmap, how did you think about development? I know yours is more of a product, not kind of so much a service, if you will. You’re not necessarily fixing the trucks. You’re more focused on the product. How did you think about, you know, that roadmap and, you know, kind of inputting customer needs back into that roadmap? I’m sure early on, maybe it wasn’t as formalized as it has been.

Tyler Robertson: Yep, yep. So, yeah, back you’re right. So here’s what happened. Like, we grew really fast. We hit a number and all of a sudden, like, things plateaued. And when it comes to building, like product roadmaps, it was really the same, same thing. We were just doing so many things all at once because I had so many ideas in my head. And all of a sudden you have 50 parallel streams going along and nothing’s coming across the finish line. And back then, my early suggestions were like, we’ll just hire more people. So I think at one time we had 40 or 50 people working in SoftW. Still nothing’s coming across the finish line. They start looking at your financials like, why are we making any money? Like, oh, that’s because we just are overspending over here. And I tried hiring a couple different managers and none of that worked out. And we ended up doing two things. One, we said, okay, we’re just going to cut this down to about eight people and we’re going to rebuild our complete software division over here. And then two, we need to get really better at strategic planning and getting better at what we do over there. And our strategic plans in the past have been pretty wide, a lot of different strategic plans inside the company. Now they’re much more narrow. And we’ve just said, okay, there’s. There’s only a couple things we need to focus on. We can’t have this many plans with this many things. We’re just not focusing on an alignment. So sometimes you gotta take a step back and really focus on the future. You gotta really sit there and spend time on where your business is going and planning, not actually working in your Business. And you know, there’s obviously stories about, about that whole situation.

Chandler Kohn: Were your developers onshore or offshore?

Tyler Robertson: Both. They were both. And we had outside companies that were both as well working with us. Yeah, when I first started, I would just need something done and I would just go kind of scope it out, go on Upworks or one of these coding sites, hire somebody and be like, build it. And I did that again and again and again. And well, you do it a bunch of times. All of a sudden now you got 10 different platforms and 10 different code bases with all these, you know, like nothing’s talking to each other. And it did create a mess. But again, that was kind of like a, we did go really fast and put some good products out there, but B, on the back end, really take a step back there for a while and kind of re. Architect and reorganize everything and say, okay, how should these work together? So there’s always a good and bad with the decision you make. And that’s one of them.

Chandler Kohn: Yep. Did you ever, you know, let’s, let’s kind of move into surviving and scaling here, you know, in terms of, you know, a near death moment. Some businesses have them like the Great Recession. Right. But was there anything for you where you, you know, you were just cash flow negative and maybe revenue dipped a little bit and you were kind of nervous?

Tyler Robertson: Yeah, yeah. I mean, four, so four years ago, you know, get my financials, I think things are fine. We’re actually starting a capital raise process. We’re projecting we’re going to go make like 4 million EBITDA that year. And we’re like, okay, cool. Um, and then we start kind of going through the process and like, things aren’t lining up right. Like the numbers aren’t making sense. Like, like, why is this so weird? What’s going on? And then I got a call from one of my vendors and he’s like, hey, you guys know you owe us like $2 million? I’m like, wait, what? We’ve been sending you money. Like at first I’m like, do we get hacked? Do we send money to the wrong account? Like, what happened? Because I go talk to accounts payable, like, well, we only have like 500 grand in bills that we owe them, not 2 million. I’m like, okay, there’s a disconnect, like, what’s going on? Well, what happened was we had Transitioned off of QuickBooks locate into NetSuite and we did that transition very, very poorly and come to find out that there’s a lot of issues One of them being all of our vendors weren’t actually getting entered into the system. There was some scripts and some automation that we had built before that was only partially working and no one had caught that. And then we had deferred revenue and we had a bunch of other things that happened kind of all at once. So, you know, we went from Thinker making $4 million. I have a couple million dollars in like a basic money market account for the rainy day fund. And all of a sudden we’re like down to like that whole money market’s gone. After about six weeks, by the way, receivables went to hell as well, because our system wasn’t actually sending invoices or statements to customers. So we weren’t getting paid either. So it was like this whammy of everything happening all at once with messed up financials, messed up money not coming in, bills not being put in the system. And when that year all got all got settled years later and we went back and refigured out everything, we actually lost $6 million that year. But we were flying blind thinking we were making money at the time. So, yeah, that was, that was scary not knowing, like all of a sudden you. All your cash is gone. You don’t know where the end of it is. You’re starting to tap into your credit line. I’m like, it was that moment too. I was like, man, I’m really glad I didn’t have like a lot of debt when this whole thing went down. This would have been catastrophic.

Chandler Kohn: But now, what year was this?

Tyler Robertson: So it was like four years ago when all that happened? It was right around Christmas. Yeah.

Chandler Kohn: So 2021. What’s that, 2021ish?

Tyler Robertson: Yep, yep, 2021ish. So it, yeah, it was a real, it was a real gut check. And I’m, I’m really glad, you know, we did a couple things. I just hired a brand new, see, our first ever real, like, well, competent cfo and I brought in a COO and a chief revenue officer. I just hired all these people, expensive people, and I’m really, I’m really glad I did now in hindsight, because I don’t know if I would have made it through without having some great, great leadership here at Diesel Laptops Underneath helping.

Chandler Kohn: Yep, that makes sense. And you know, when it comes to scaling, sometimes you have to have. The business has to be in a position to scale. You have to have scalable technology. You have to have, you know, middle management that can help help you scale. What were, what were the hardest challenges there, getting the business right to scale.

Tyler Robertson: Yeah, I mean you’re talking about growth pains, right? So like this is what happens with every company in every industry is you get to a certain revenue number and then, then things just kind of plateau. Right. And what it comes down to a lot of times there’s a lot of reasons. Right. But you’re talking about one of them and that’s operational systems, as we like to call them around here. So whether that’s your phone system, your CRM, your ERP system, your warehousing system, whatever it is, you sometimes you outgrow it. And that’s what we did several times. And it becomes a super painful thing to have to go switch your entire ERP system around or switch your entire phone system around, your whole CRM system around. I mean, we’re switching CRM platforms again this year. But you know, it’s just, it’s a year long process and it just sucks all the life out of you and everybody else and it impacts how your processes are and how you do things inside a business. But it’s one of those things that you have to do if you want to keep growing your business to the next level. So for us it’s just being really mindful of like we know we want to get to in five years, what are, here’s the bridges and things we have to do. So let’s just start knocking them out and doing them. And we just went through one about two months ago. We switched our phone system, our own phone system didn’t have the right reporting or call center metrics. I didn’t think I’d have a call center with 50 people in it in several different departments three or four years ago. And we didn’t have software to do that. So we had to have that now to understand call routing, how long customer hold times are and what like all the things you need to know to be a functionally efficient call center. We didn’t have those tools, so you have to swap it out and go to the next thing. But yeah, it’s definitely having the right people, having the right foresight and having the right vision of where you want to get to. If you don’t know where you want to get to, you can’t build a roadmap. Whether it’s people, operational systems, lining up resources, hiring the right people like you just, you can’t do it unless you know where you want to get to.

Chandler Kohn: Yeah. Now it sounds like you have grown pretty aggressively. Obviously if you look at your combined annual growth rate but you’ve also scaled seemingly cautiously. Sometimes those two don’t go together or they’re not successful. Tell us, tell the audience how you have grown aggressively, but done it kind of scale cautiously. I’m interested to understand that.

Tyler Robertson: Yeah, I mean, I. Look, I think if we would have went out and raised a bunch of money, we could have really thrown a lot of gasoline on the fire here and gone even faster. However, our industry is really, let’s just say, really specific. It’s really niche, right? Like we’re doing truck repair and equipment repair stuff. And the problem we ran into before, especially with like engineering, software engineering, is we hired a bunch of people that were great software engineers, great software managers, but they didn’t know anything about our industry. So all of a sudden they’re building things and trying to do things that don’t really help anyone in our space. They look good on paper, but they don’t actually help. So we’ve. I’ve learned like, hey, we really gotta, like, think through these things a lot more and not just go wild west. I had that, like I said earlier, I had that problem of doing so many things all at once and nothing was getting done. And I think if I just had an unlimited checkbook there and it was just throwing money at things, I’d probably still be doing that and thinking I’m accomplishing a lot, but I’m not really doing that. And strategic planning is a big thing the company started doing five or six years ago is saying, okay, where are we at now? Where do you want to be in three years and five years? What’s this year’s goals? Where are we going to get to? What are the smart goals? Who’s responsible? What are we doing? And by doing that, it really got us focused on what are really the top three or four things every year that we can go focus on. To go grow the company in the right direction and not have everyone not get distracted by shiny objects all year long and not have all these other distractions coming in. We can easily say, like, this is what we’re doing. This is the path. We all agreed to it. This is what we’re doing. Unless something dramatically changes, let’s not deviate. And that was definitely missing in those early mid years of us doing that. So what I’ve learned is like, it’s not a race. There’s no first place here at all, right? This is about building something sustainable that’s gonna be around for a long time. I’m not just trying to be a flash in the pan. Grow a company, cash out, and be gone. I’ve been doing this for 10 years. You know, we’re probably gonna raise some money here and do some other things so we can go a little bit faster now that I think we do have a good foundation. But until I felt comfortable with that, it just. It wasn’t even an option I really needed to explore because I didn’t. And I didn’t need to.

Chandler Kohn: Mentors, coaches, and advisors had. You know, you probably didn’t have many, if any, in the early days when you were working out of your home. Maybe you have some now.

Tyler Robertson: Yeah. So back in the early days, I mean, I’m a family of business owners. So when I grew up, my. My. My father owned a business with his brothers. My great grandfather had started it. When I grew up, we didn’t sit around the table talking about the weather and sports and whatever. We literally. My dad would literally sit there and talk about business. Like that was. Our family gatherings are talking about business. I was involved in the family business from the beginning.

So he went before for Diesel, and after college, I went to work for my family. So I’ve been around business. I’ve been around business forever. Like, I’ve. I’ve loved business, and I. Plus, I had advantage of working for somebody else for 10 years. So I got to see how other people did this thing with truck repair. So for me, a lot of it was like, okay, I know what to do. I know how to do these things. I know how to do accounting. Like, I can handle the basics here, but in terms of mentorship, there really hasn’t been, like, anybody out there. I am a member of a Vistage group. We do meet once a month. CEOs read a ton of books, listen to a ton of podcasts. And of course, like, as you become a CEO or senior executive, you start to make friends with other CEOs and other executives. So I have friends that are running other companies, and we go vacation together and do all those things as well. We hit each other up on text or email if we have questions. So there are. There are people around me that I’m able to bounce questions off of. But the biggest one is really my C suite, my CRO, CFO and coo. Those are the guys. The three. The four of us, we. We talk constantly. We have a group chat going, and we meet for cigars and whiskey at least once a week and probably have dinner at least once a week as well. So we’re really in tune with what we’re trying to accomplish.

Chandler Kohn: That’s excellent. Appreciate that. Now, I think maybe the last section here is kind of your leadership evolution. You know, how have you gone from that? Hustlepreneur. Right, I like that word. I heard it somewhere else. But how have you gone from that to be basically delegating and strategically managing the company at a high level? Sometimes that’s hard to do.

Tyler Robertson: It’s really hard to do. And it was a lesson I. It was a lesson I learned, right? So I remember this is gonna be like five or six years ago now, but I remember sitting in my office one day, it was like the non stop revolving door, people coming in asking questions, right? And I’m trying to do something, and it’s just like one after another, one after another, one after another. And, you know, I got thinking about it. I’m like, you know, why is everybody coming to me like? And I started to realize. I started talking to a friend about it and he’s like, Tyler, you realize, like, you’re probably the biggest roadblock to your company’s growth at this point is. Is you. Because everyone’s coming to you for everything. Like, your. Your job should be to not do or not to deal with any of those things and get them empowered to do those things. And he was absolutely right. So from that moment on, I was like, you know what? I have to go hire people and I have to not do this day to day stuff. I have to get out of the day to day so I can focus on the future. Like, I don’t. I need to get to the point where I don’t. I’m not even needed around here. And this thing keep running the way it is. I’m just needed here to keep the vision going forward and for the company to keep making the big pivots and the big changes to go in the right direction to what the ultimate goals are here at Diesel Laptops. So for me, that was a big one, just getting out of the way. And we went down an entire path with leadership training. We, we some leaders, some people that were leaders didn’t want to be leaders after that. Some people that we didn’t think could be leaders wanted to be leaders. Like, it was. It was a really interesting experience, an interesting time, but it led us down the right path of me just getting out of the way. I had to learn to trust people. I had to learn that just because they do it their way doesn’t make it better or worse than mine. And I come to find out a lot of times their way is better than mine. So it’s been nice to, like, relinquish that control, but it took a long time to get there. But that’s exactly why a lot of companies get stuck at certain revenue thresholds. They just. They’re trying to do it all, and they’re just not spending that time working on the business. They’re just working in the business.

Chandler Kohn: Is there anything else that you kind of had to, quote, unlearn?

Tyler Robertson: I just had to unlearn, yeah. I mean, there’s been other things, right? So it’s like if I walk around, I. I used to do this, right? I’d walk around and I’d be like, oh, hey, Joe, like, what’s going on with this thing? I haven’t heard anything in, like, a couple weeks or months or whatever. And, you know, he’d answer me. I’m like, cool. That’s it. Great. And then I come to find out two weeks later. Joe now spent the next 40 hours a week working on this one thing I happen to ask him a question about. Not because he wanted to, because he thought it was important to me.

So I’ve learned, like, when I. When I undermine or go, like, down too far and start asking questions, people get really nervous and really squirrely real quick and start acting completely different. So I’ve really had to learn and trust the managers we have. And it gets hard because now you get separated from things. I. I used to do everything right. The packing, the shipping, the sales, tech support. You gotta talk to customers every day. Now I don’t get that experience. Now it’s just something. It’s something different. So learning to adjust on how your company runs, who’s running it, how things are getting done during the day. I mean, there’s things I don’t. I don’t even know how they work around here, but it’s not my job to. It just knows, like, hey, like, it. It works. That’s all I need to know about this. Let’s not get too deep into the weeds. But, you know, as someone. Someone like me who was entrepreneur and constantly wants to get involved in things, I’ve got to learn to, like, not get involved and take a step back and trust the people that I have there.

Chandler Kohn: What’s the toughest call you’ve had to make as an entrepreneur? Starting diesel laptops.

I know there’s been probably a million of them, but if you. If you had to pick one, I mean.

Tyler Robertson: Yeah, I’ll tell you, the biggest one is, what am I doing with this company? Am I. Am I going to own this thing forever. Am I going to own it for three years and sell it? Am I going to make it an esop? Am I going to have my kids run it? Like, what. What am I doing with this thing? And until I made a decision and I realized that decision was holding me back, like if I want to sell the company or if I want to turn into an ESOP or I want to go public, those are probably three different CFOs. I need to hire in three different directions. I need to bring the company versus I’m going to pass this to my kids. And it’s a family business for the next 40 years. So that would by far was one of the biggest decisions that I. That I had to make was where what am I doing with this company and what does the end look like? Because the end comes to all of us, whether we want it to or not.

Chandler Kohn: Yep. Any. Anything that basically negatively impacted your employees or, you know, essentially maybe their families besides, like, you know, poor performance, where you had to let somebody go sometimes, you know, I see in the lower middle market, these people become families, right? Like they’ve had employees with them for 15, 20 years. The employees rely on them. Have you ever had to work through that where you kind of negatively impact somebody in their family for kind of the overall health of the business?

Tyler Robertson: Yeah, yeah, it happened about two years ago. So when we really looked at. I was talking earlier when we looked at that software engineering division, we had those 40 or 50 people, we were down to eight. We kind of looked at it out like, well, if we’re heavy here, where else are we heavy? And you start looking around and you really start questioning like, well, do we really need this? Is this person really lining up with our strategic goals of where we’re going? Is this really the best use of our resources to. To invest this much money in this role for this year? Are we overstaffed in some areas? And we just were being nice, not really cutting people when we knew they weren’t performers. Where are we? So we went through that whole process and yeah, there was a bunch of cuts we did all at once. When we looked at it was like the right thing for diesel laptops. Here is kind of do a reset. And there’s some people that have been here for a while that unfortunately aren’t. We did everything we could to make that work. But even now, I just had a situation this week. We have someone I’m friends with, my kids are friends with them, they work for me. And unfortunately, the company’s going A different direction. And it’s like, hey, I’m sorry. I like you, we hang out, we’re friends, but unfortunately, I just don’t have a role for you anymore in the company. And those are hard conversations to have. But at the end of the day, we’re not afraid to have hard conversations because our guiding lights, always the same, what’s best for Diesel Laptops. And as long as we kind of look at that as our North Star, it doesn’t matter how we feel about a situation. Then it’s like you just. You have to do it. And unfortunately, a lot of times, a lot of times the right decisions, the hardest decisions, and that’s, I think, trips up a lot of entrepreneurs and business owners too. They don’t want to make the hard decisions due to. They feel like they’re gonna hurt someone or whatever. But honestly, most of those employees, almost all those employees now, they have other jobs. Some are excellent and doing great. I’m still Facebook friends with them. I follow them on LinkedIn. They’re succeeding in other areas, so it’s not like it’s the end of the world. And some you just. You gotta do what’s right for your company.

Chandler Kohn: Yep. Yeah, I’ve heard that kind of a guiding GPS for a business, particularly a young one, is having a game plan, having people having systems. So gps, game plan, people, systems. When it comes to making hires, you know, I don’t know, maybe you do two to three interviews per person. I would guess that’s 600 interviews. If you have 200 people currently, what are two to three things you look for in these folks that you feel like best translate to a successful employee?

Tyler Robertson: Yeah. So, you know, I don’t do a lot of the hiring, but what I do do is a lot of the employees that we hire come sit with me for 20, 30 minutes because I want to know who they are. Right. That goes back to the early days when I hired them, brought them to lunch, got them their families, the whole thing. But now it got weird for me at one point, walking around, not knowing, is that an employee? Employee, spouse, like, who. Who is this person? What do they do here? So they all come sit with me. And I would say I usually ask them, you know, I asked them a bunch of questions. And one of the ones I always ask is like, you know, where do you see yourself in a couple years? And most of the time you get the same generic, like, oh, I see myself at Diesel Laptops doing blah, blah, blah, blah, blah. And every once in a while you get these Other employees that walk in and they have a different answer. Their answer is, you know what, here’s what I’m going to do. And they have like the five or ten year blueprint of their life laid out on what they’re going to do. Those are the employees I want to hire because they know where they’re going, they have a plan where they’re going, and I know if they have a plan there, they’re going to have a plan with me.

Chandler Kohn: Yep, excellent. That’s helpful. That makes sense. So let’s focus on, you know, we’re about 40 minutes in. Let’s focus on closing advice. This is a basically an owner to owner podcast. It’s built to support small business owners. That’s kind of the reason why I started this. You know, if you could give owners, other owners, one piece of growth advice that’s not obvious, what would that be?

Tyler Robertson: Look, a, don’t take risks. You can’t afford. Right? So like take risks, but don’t do one that’s going to bet the entire farm on your business. The other one I say is just think differently. There are so many different ways to go grow a business and attract new customers. You just gotta go go where your customers are. You don’t need billboards, all these fancy marketing things. I grew mine with, by myself, with nothing essentially. Right. There’s plenty of resources that are out there. And three, it’s not a race. Just take your time, make the right decisions, make sure you spend time every single day of the week just thinking of ways to improve your business, not just getting whatever needs to be done that day would be the three pieces I would give.

Chandler Kohn: And then for, for owners that aren’t content, you know, they’re trying to grow their business but are stalled or stalling outside of market drivers, like tariffs. Right. You know, what do you see? What mistakes do you see some owners making that other owners should be aware of to prevent that?

Tyler Robertson: Look, if you want to grow your business, it’s real simple. You just start spending some time putting some strategy together, get the whiteboard out or get with your co workers or whatever it is, figure out what part of the market you want to go after and put a strategy in place. And it’s probably not going to work. And then you’re going to go do another strategy and another strategy. Another strategy. There’s a thousand ways to go grow any business. It doesn’t matter what it is, but you got to put that time and energy into it. So if you think writing a check to a marketing company or somebody is going to just magically grow your business overnight. It’s not. No one knows your business as well as you do. I have yet to meet someone that’s got this genius idea and promises you can promise me the world and actually go execute and go grow my revenue 3x. Like it just, it’s not a thing. It just takes consistent daily effort, trial and error and finding out what sticks. There’s obviously best practices, best strategies out there. Donald Miller’s story brand obviously is a big one that we follow with our marketing side of it. Duct tape marketing. There’s all kinds of books and tools out there and things to do, but you just got to go, you got to go try them and experiment with them and find out what works best for you, your company and your industry and your customers.

Chandler Kohn: So now you’re sitting here, this is the last question. Maybe around $100 million in revenue. It sounds like. What would you go and do differently if you restarted it today? I know that’s a loaded question.

Tyler Robertson: Yeah, I mean if there’s anything high level in hindsight, nothing. Right. Like we gotta get to a great place in 10 years and great revenue and we’re profitable and all those things. But I will say I’m taking that exact advice. So for me it’s lessons learned. So I started a new company 18 months ago and it’s doing what Diesel does but for the marine world and it’s just going much faster and much bigger there. It’s not going to be as big of a company just because of what the way that market is. But once you have some knowledge, you know how to do things, things can go so much faster the second time around. So for example, I don’t have to figure out how to use QuickBooks online. I already did it once. I don’t have to figure out how to like build a website or who I can go to get paid search going or how to get our phone system set up or how to get email marketing campaigns going, going or what skill sets I need to hire for. Like we already know how to do all those things because you’ve been there and done it. So I get now like going through this, why people that launch one business tend to launch another one and another one, another one and be successful at all of them because they know what they’re doing and there’s no real like magic sauce to any of it. But it’s just like experience that you have doing those things. So for me, I, I wouldn’t say like, I, I’d say I, I do things earlier. So like at Marine, I definitely hired a bookkeeper earlier than I did at Diesel. I’m definitely more concerned about it, security. We had a hacker at Diesel get into one of our accounts and steal $44,000 in the early days, like, okay, now we’re going to be a little more serious about security, but I’m able to lean on Diesel’s teams and Diesel’s resources to do those things over at Marine. So it’s just, it’s just so much easier and smoother the second time around. You’re not having to figure out a lot of just like the, the operational systems and the pieces of the puzzle that you need. You know what they are. You just got to go implement them. And you can go so much faster when you do it over and over again.