INTERVIEW | Make Money by Learning Before You Earn with Dean Matthews

Summary

Travis Makes Money — INTERVIEW | Make Money by Learning Before You Earn with Dean Matthews

Host: Travis Chappell
Guest: Dean Matthews, Founder & CEO of On the Clock
Episode Date: July 23, 2026

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Episode Overview

In this episode, Travis Chappell sits down with Dean Matthews, a self-described lifelong learner and founder of On the Clock—a workforce management platform serving over 16,000 small businesses. Dean shares his journey from a mechanically inclined teenager fixing lawnmowers to running a successful SaaS business. The discussion dives into the value of learning through “doing,” the evolution of business skills, and why prioritizing learning before earning can ultimately lead to much greater long-term financial (and personal) rewards. Listeners get a transparent look at building a business from the ground up, the importance of mentorship, adapting to change, and embracing new technology.

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Key Discussion Points & Insights

Dean’s Early Money-Making Days

[02:16]

• Dean recalls his entrepreneurial spirit at a young age, repairing lawnmowers and weed whackers for neighbors.
  • “I hung a sign on our tree in the front yard… people started dropping their stuff off… I might have made a couple hundred bucks in a week as a 13-year-old.” — Dean Matthews [02:31]

Family Influence and Early Career Choices

[03:22]

• Dean’s father was a house painter, and his mother stayed at home. They encouraged stability but Dean sought independence.
  • “They really encouraged me more to just get a good job… but… our brains are wired differently. I always had higher aspirations.” — Dean [03:22]
• He struggled with traditional education, pursued community college, but ultimately left to work directly in business environments.
  • “I wanted to be around business owners… to start to understand what they’re doing… how a business runs…” — Dean [04:26]

The Value of Learning on the Job

[05:41]

• Dean describes his early jobs as a service technician, learning hands-on skills and customer interaction.
• Found a mentor (Terry) who treated him almost like a business partner, sharing deep organizational knowledge.
  • “He taught me everything that he did… invoicing, the customers, the vendors, the… financials… it was a really great opportunity.” — Dean [06:34]
• Travis underscores learning through proximity and doing as more impactful than formal education.
  • “…that learning period is more valuable than any university degree… you get paid to do it, you know.” — Travis [07:25]

The Reality of Business Education

[11:13]

• Both Dean and Travis stress that degrees can be useful but aren’t required for entrepreneurship.
  • “We've seen a lot of degrees come through MBAs and that's great… but you don't really learn it until you get on, on the street…” — Dean [11:13]
  • Travis shares a humorous anecdote:
    • “My buddy Brad… he was like, oh yeah, I have five MBAs… they all work for us.” — Travis [11:54]

From Mechanical to Software—A Mindset of Adaptability

[13:33]

• Travis asks about Dean’s transition from manual trades to founding a SaaS business.
  • “For me, the way my mind works… it’s really all the same… it’s just reasoning and sorting through things and getting a mental picture…” — Dean [13:33]
• Emphasizes adaptability and seeing transferable skills between disciplines.

Launching On the Clock—Spotting Opportunity

[17:04]

• Dean describes the origin of On the Clock: reading small business forums in 2003 and spotting repeated requests for time-tracking software.
  • “I just saw the pattern and I’m like, yeah, I can build that… literally the next day started working on it.” — Dean [17:18]
• First version launched months later as a passion project alongside his consulting business.

Grassroots Growth: SEO and Word of Mouth

[20:17 – 22:09]

• Early growth fueled by SEO, some PPC, and word of mouth; employees recommending the software as they change jobs.
  • “…having a great product that a business owner will recommend to another business owner.” — Dean [20:36]
• Still prioritizes SEO and referral growth.
  • “One that still continues today and I love it is word of mouth.” — Dean [21:21]

Dean’s Role and Focus

[22:32]

• As CEO, Dean directly leads strategy and product vision, working closely with director-level talent.
  • “I focus real heavily on my direct reports… overall strategy for the company… I love building a product that people love and that’s of value to them.” — Dean [22:32]

Looking Ahead: Navigating an Uncertain Tech Future

[23:23]

• Dean is focused on adapting his business to rapid changes in technology, AI, and SaaS trends.
  • “I talk to my counterparts… and the universal answer is that we don’t know right now [where things are heading]… really looking that far out and trying to predict and start to steer the ship…” — Dean [24:11]

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Notable Quotes & Memorable Moments

• On learning before earning:
  “Get out, go find somebody who you admire, respect, who's doing something that you're doing. Go work for them… Prioritize earning over learning when you're in your 20s and then go out, start your business, spend a lot of time with your customers.” — Travis [24:52]
• On not rushing for high income early:
  “…you might be making 60k at 24, but when you’re 44, you might be on your third business and you’re making 3 million…” — Travis [26:37]
• Dean’s core advice:
  “Learn first. Don’t worry about the money right now. Learn, figure out how to serve people… work your way up in that job. Become the owner’s partner.” — Dean [25:23]

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Key Timestamps

• 02:31 — Dean’s first entrepreneurial experience: fixing lawnmowers as a teenager
• 03:22 — How Dean’s parents influenced his work ethic and mindset
• 05:41 — Lessons from early jobs and learning from business owners
• 11:13 — Degrees vs. real-world experience
• 13:33 — Moving from trades to tech: mindset and skill transfer
• 17:04 — Identifying market needs and launching On the Clock
• 20:17 — Early growth drivers: SEO and word of mouth
• 22:32 — Dean’s current strengths and day-to-day role
• 23:23 — Preparing a SaaS business for future changes in technology
• 24:52 — Travis’s masterclass summary and advice to young people

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Where to Connect with Dean

[27:19]
“Find me on LinkedIn… Dean Matthews, one T in Matthews. If you’re a young entrepreneur or a seasoned entrepreneur, just connect with me. I love talking mentoring with younger or even older people, helping them out, spreading knowledge.” — Dean Matthews [27:19]

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Final Takeaways

This episode delivers a real-world roadmap for aspiring entrepreneurs:

• Don’t underestimate the power of learning by doing. Find mentors, work hands-on, ask questions, and immerse yourself in the business world.
• Degrees show diligence but aren’t the only path. Business acumen is built through repeated exposure to real situations and challenges.
• Spotting and solving real customer problems creates success. Market research can be as easy as reading customer forums and being willing to build what’s missing.
• Play the long game: Early slow growth and “lower” salaries can pay off exponentially if you focus on building skills, relationships, and entrepreneurial judgment.

This episode is for anyone feeling “behind,” anyone on the fence about college or career paths, and anyone wanting proof that learning through action is a viable and often superior route to making money and living a rewarding life.

Transcript

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[Travis (Podcast Host)]

You're listening to the Travis Makes Money podcast.

What is going on, everybody? Welcome back to the Travis Makes Money podcast where it's our mission to help you make more money. On this episode of the show, I have a new friend, Dean Matthews. He's the founder and CEO of On the Clock, a workforce management platform that helps small businesses track time, schedule shifts, run payroll and manage HR. Simply and error free. On the clock serves over 16,000 businesses and over 160,000 employees, which are mostly US based small businesses. Lifelong learner, Dean is endlessly curious about business culture, science, tech, AI and psychology. And so he is here now on the show to talk to us a little bit about how he's made some more money. Dean, what's up, man? Welcome.

[Dean Matthews (Guest)]

Thank you for having me, Travis.

[Travis (Podcast Host)]

Of course. So let's, let's go back in time first of all, tell me the first time you ever made a dollar that was exciting or shocking or surprising, like the first time you got paid for something that you were like, I can't believe somebody just paid me money to do this.

[Dean Matthews (Guest)]

Yeah, no, I'll go back to probably early teens. I was kind of into anything that had a motor that would kind of go fast. So I had mechanical skills and I could fix lawnmowers or weed whackers. So I hung a sign on our tree in the front yard and you know, lawnmower repair and you know, I started getting people stopping by, dropping their stuff off and you know, I'd fix their, fix their lawnmowers, their weed whackers, whatever it was. Didn't really know what I was doing. It was just kind of cash and. But it was great, you know, I might have made, you know, maybe a couple hundred bucks in a week as a 13 year old. I mean, I'd say that was pretty good, you know.

[Travis (Podcast Host)]

Yeah, I can't complain about that, man. Can't complain about that. What did your parents do?

[Dean Matthews (Guest)]

So, yeah, my parents, my father was a painter, so like industrial, like house painting. And my mom was pretty much stay at home. So, you know, they, they really encouraged me more to just get a good job, you know, and. Which is really good advice, of course. But you know, as you and you know, a lot of us entrepreneurial people, our brains are wired differently. So, you know, I always had higher aspirations. I didn't exactly know what it would be back then, but I knew I wanted to do something and I pretty sure I wanted to do it, you know, myself. So.

[Travis (Podcast Host)]

Yeah, yeah. So did you end up going to school then?

[Dean Matthews (Guest)]

You know, I did, I tried, but wasn't really for me. You know, school's great, don't get me wrong. Nothing wrong with that. But for me it just wasn't. I was just too far ahead, I guess you might say. And I just had a really. I struggled paying attention. I just wanted to move. So.

[Travis (Podcast Host)]

Yeah, so what did you, did you end up just dropping out? Did you end up taking a job, starting a business? What was the exit plan?

[Dean Matthews (Guest)]

Yeah, so, you know, got through high school, mostly through high school, got the diploma. I, I really just started at the local community colleges relatively full time. I think I got maybe a couple semesters in and just realized I was just really, really struggling to, to just to do the work. It just, it just, I couldn't see the direct application to what I wanted to do immediately. So really I just kind of Dropped out of. It was community college, so it's not really dropping out, but just went out and started looking for a position where I could grow, I could do something. I didn't start on my own right away, but I started. I wanted to learn. I wanted to be around business owners, business leaders, managers, and just start to understand what they're doing and, you know, how a business runs and how to work with people and the money and customers and providing value. So I really did start, really, the first, I'd say, you know, six, seven years. I did start working with other people for other people.

[Travis (Podcast Host)]

What were some of those jobs that you had early on and what were some of the lessons that you learned?

[Dean Matthews (Guest)]

Yeah, one of the first real jobs was I was actually a service technician for this electronic industrial equipment. So started out really with very little skill, but I was electrically and mechanically inclined. So I adapted to that really quickly. And with that, you know, I was directly in front of customers all day long, you know, professionals. So I really had to learn how to work with them, how to properly talk, how to communicate with customers. Also, you know, quickly started understanding the different facets of the business and offering my help there. So was able to start to help out a little bit in the office, you know, created a website for them, you know, started to do some little bit of invoicing and help with the computer stuff and just kind of got my fingers into just a lot of different things. And, you know, that was my first job. The second job was very similar. Similar, basically almost the same industry, but this one definitely had a lot more potential to grow. So I was extremely attracted to that. So I, I went in there and I effectively started working almost as a partner with the. His name is Terry, the owner. I wasn't, you know, financially vested by any means, but really I did. He taught me everything that he did. So nice, you know, the invoicing, the customers, the vendors, the. The. Some. Some of the basic financials and really got to ride under his wing for several years. And really he treated me much like. Almost like a partner in business. So that was. It was a really great opportunity.

[Travis (Podcast Host)]

Yeah, I love the concept, especially when you're younger and you're not exactly sure what you want to do, where you want to be or have a. Have a plan, have an idea. I love the, Love the concept of basically just flowing power to power, right? Like going, going and finding somebody who's kind of just like, look, I don't really know what I want to be doing, but this person kind of seems to have it figured out along the path that I know I eventually want to go down. What if I just go do whatever's required of me for that person, you know what I mean? Like that, that that learning period is more valuable than any university degree is going to be in terms of your ability to really figure out what it takes to run a business. Like you can study it all day long, you know what I mean? You can read a hundred books about it. But when you're, you know, day 12 and you're trying to take care of a upset customer who you're trying to de escalate and then you're trying to see, well, if we lose this customer, what does that do to our financial forecast? What does that mean for our P and L this month? What does that mean for our ability to hire employees? Or you know what I mean? Like you start making those decisions. It's you know, the, that that can be a much, much faster path to learning and you get paid to do it, you know. This episode of the show is brought

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[Travis (Podcast Host)]

pay to do it.

[Dean Matthews (Guest)]

Yeah, I, you know I, I'm with you on school and nothing wrong with school, you know, I had no issues with it but you know, I definitely, you know, here now, you know, older and having higher, you know, much higher level people working for me. You know, we've seen a lot of degrees come through MBAs and that's great. I mean it shows diligence and shows you can get through there but you don't really learn it until you get on, on the street if you will, you know, in business and, and an actual environment where you're serving customers and you're, you have employees or teammates. That's where the real education, you know, begins. That in my opinion.

[Travis (Podcast Host)]

Yeah, it's not of course, you know, not a knock on school. I just like oh no, no. My buddy, my buddy Brad, I want to say he was a high school dropout. If he wasn't a high school dropout, he definitely, definitely didn't go to college. And when people asked him asked him about that later on, he was like, oh yeah, I've. I have five MBAs. And they're like, wait, what? You have five? He's like, oh yeah, they all work for us. You know, that's, you know, it's like, it was like, yeah, you don't have to be the person who has the mba. And if you need that skill set, there's plenty of them that you can go hire and they can help with this thing that you have a blind spot in agreed. Is not required in order to be able to start a business.

[Dean Matthews (Guest)]

No. And I mean nowadays, I mean you don't. The things that you need to learn and to run a business are free. You can go find that for free anywhere. Yeah, yeah, yeah. There you could read or very little books, you know, the web, AI, you know, videos. It's there. It's just a plethora of information out there.

[Travis (Podcast Host)]

So. So Dean, I asked this question a lot to a bunch of people. Typically what I start doing in my mind is I kind of start sequencing life events like on a timeline in my brain and then I can start seeing a path to where, you know, the beginning of the story matches to the end of the story. But I have to admit I'm struggling with you because it's wild to me that you are sort of like mechanical, electrical, like trades inclined person who works really well with your hands and these types of contexts. And now you're, you have a software company. So how, how did that happen? Where, you know, where did the gap for us, man?

[Dean Matthews (Guest)]

You know, I, for me, the way my mind works, it's whether it's mechanical, electrical, you know, also software engineer as well, not so much anymore. You know, we have a team of that. But in my mind it's, it's. For me it's, it's really all the same, you know, so the things I learned mechanically or electrically, if you will, both really directly apply to the, to the software side. And in a lot of ways it really applies to just in my life, at least a lot of things in life. It's just really reasoning and sorting through things and getting a mental picture of whatever it is that you're working on. And that, that I think is the big connection for me is that whatever it is that I have up there is adaptable to pretty much any, any situation. Mechanical, electrical engineering, people, psychology, business, finances are at least the detailed finances. Not my strong point. High level, I'm good all day. But yeah, so yeah, there's, there's something there. I don't It's a common element between them all. I don't really have a name for it though. Like it's an intuition or just a reasoning ability, something like that.

[Travis (Podcast Host)]

So, so after you work for this other guy, did you go start your own business? Is this the. What, what, what business is this in the lineup of companies that you've started?

[Dean Matthews (Guest)]

Yeah. So worked with Terry for about four years. That's where I, I really learned a lot with him and was put in front of bigger customers and bigger situations and deals. But I pretty much knew right when I started there that I would be doing something on my own. So a few years in, I broke the news to him and he knew, he, he could tell, you know, certain people are just movers. And he was like, no, I understand. You know, he was like, I, I'm just. It was a pleasure, it was an honor to be part of, you know, this part of your life. And, you know, really, you know, made the announcement with him. And I think I stayed another month or two just to kind of help settle things out, you know, definitely wanted to honor that. And at that point I went off into computer consulting. So I had really been working on my own personal time and at that position to really learn how to, to develop software. It even goes back to my early teens. You know, I just wrote games and such, but really took that and opened up a computer software consulting company. It was called Paradigm. I, I still, the entity still exists and I found here in the Metro Detroit area and also inherited a few from the company that I had left from. I ended up with a couple dozen really good clients and I built whatever software they needed, whether it was accounting, mrp, inventory control. I learned a lot there. That was, you know, that was a stint that I got to work with the CEOs, the CFOs of SMBs. You know, a lot, a lot of the M's and learned a lot there.

[Travis (Podcast Host)]

Yeah, yeah, yeah. Okay. So what initially got you thinking about this? You know, payroll, manage your employees, manage your team? What, what, what got you thinking in that direction?

[Dean Matthews (Guest)]

Yeah, so that's, I call it the kitchen table story. So this was approximately December ish of 2003. So like 23 years ago, I was sitting on my laptop on a Friday night browsing through like Accounting, the small business forums. Remember the forums that used to be a thing like 20 years ago? Yep, they're still around. But I, I was just looking through these forums for hours and I was, I started to notice this pattern. All these small business owners and accountants and CPAs, they were looking for a time tracking system, you know, for employees to clock in, clock out, generate hours for payroll. And I just saw the pattern and I'm like, yeah, I can build that. I haven't done it before, but I can do that. And I had the confidence and literally the next day started working on it. And then a few months later, the first version of on the Clock launched. That would have been May, April of 2024 at this point. And it was super simple. It was just me. You know, I learned. I did all the marketing, the SEO, did the development, the customer support. And it really was a passion project at first. You know, I still have my consulting company and I had a few other online websites similar to that that I had started. Yeah, that was, that was the inspiration. I was just reading through these forums, these posts by all, you know, dozens, hundreds of small business owners and accountants.

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[Dean Matthews (Guest)]

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[Travis (Podcast Host)]

What a great way to get some customer insights. Yeah, you know, like that's. I mean, that's basically doing market research without even realizing it and then spotting that there's potentially this blue ocean that existed there that nobody was serving.

[Dean Matthews (Guest)]

It was, yeah. What.

[Travis (Podcast Host)]

What was your initial strategy to start bringing on clients for this business?

[Dean Matthews (Guest)]

So the Biggest thing back then was SEO. You know, get your website out, focus, you know, the on page and off page SEO. We did a little bit of ppc, paid that kind of got a jump started. But really what drove us for that first, you know, several years is just continuing to work on that SEO, the marketing and also, you know, having a great product that a business owner will recommend to another business owner. We also found, you know what, what we do is we track employee time that employees, when they move, you know, the turnover rate is around 25 to 35% depending on the year. Every year a group of employees moves to a new company and we found, I found that they would go to their new company and recommend us because we had a great product that worked well and was easy. So, so yeah, so it was, you know, SEO, marketing and word of mouth. What were the big drivers in the

[Travis (Podcast Host)]

beginning and what about now?

[Dean Matthews (Guest)]

Now it's, it's, it's actually very similar to be honest. You know, we definitely focus heavily on SEO. Marketplaces are a big thing. Partnerships also are a big thing. We go to a lot of the shows, some of the local ones, some of the bigger national shows, you know, for us, you know, ago or there's several terms, you know, AI optimization, making sure we're found when people are searching there. But one that still continues today and I love it is word of mouth. We did a poll a few years back and it was, it was in the single digits, but it was the high single digit percentages of people that said it was recommended to them by somebody else. Wow. So, so that, that, that to me is, is really invaluable.

[Travis (Podcast Host)]

Oh yeah, no kidding, man. I mean it makes it a lot easier to sell the product when you have a bunch of free leads that are coming up.

[Dean Matthews (Guest)]

Customers do it for you.

[Travis (Podcast Host)]

Yeah, right, exactly. It gives you a stronger position to be able to do that from. Would you, what, what would you say your strength is inside of the business? Is it, is it product? Is it customer service? Is it sales? Like what, what exactly do you feel is like your primary role these days?

[Dean Matthews (Guest)]

Yeah, well, my primary role, you know, CEO. So you know, I run the company but I'm also product director. So you know, I focus real heavily on my direct reports. We every, we, we have, you know, all departments are covered with director level talent. So I work with them a lot on strategy for their departments, overall strategy for the company. And so that's a really strong point of mine and I love, I love doing that. The secondary would be product. I love product. I love, you know, building a product that is, that people love and that's of value to them and that, again, that they recommend. You know, that means a lot.

[Travis (Podcast Host)]

Dean, what is, what is the thing that you're really focused on these days? What are you trying to work on? What are you thinking about? What are you excited about?

[Dean Matthews (Guest)]

I'd say really the biggest thing right now is trying to understand we're a software solution, right? So we're online, trying to understand where technology, AI, the Internet, everything is going and where companies, not just us, but Companies like us, SaaS, companies, fit in. You know, there, there may not be a lot that changes, but there are going to be some changes, and I would say there's still going to be significant. So that is probably one of the biggest quests I'm on right now. I wouldn't call it a struggle because, you know, I'm discovering things and we're figuring it out. I have talked to does, I've been to conferences with CEOs, my counterparts, and other companies, and I talk and I ask them the same question. You know, where do you think things are going? And the answer, the universal answer is is that we don't know right now. So. So I think that's really one of the bigger topics that I'm working on nowadays is where do. Does a company like us, and it's not just us, because there's hundreds of thousands of us. Where do we fit in in three years, in five years and 10 years, you know, really looking that far out and trying to predict that and starting to steer the ship in that direction.

[Travis (Podcast Host)]

Dean, I appreciate you coming on and sharing. Man, this is like a masterclass of entrepreneurship in my opinion. This is what I recommend to young people, is like, get out. Regardless if you go to school or you don't go to school, get out. Go find somebody who you admire, respect, who's doing something that you're doing. Go work for them for a period of time. Prioritize earning over learning when you're in your 20s and then go out, start your business, spend a lot of time with your customers. Grassroots, like, this is the, this is the step one, step two, step three to starting your own business and actually seeing it be successful.

[Dean Matthews (Guest)]

So 100%, I think you're, you're right, you're learning first. Don't worry about the money right now. Learn, figure, figure out how to serve people, how to serve customers. Provide something of value. Yeah, and yeah, use, use a job and, but work your way up in that job. You know, become the owner's partner.

[Travis (Podcast Host)]

Yeah, yep, yeah. Earn a paycheck while you learn from the person who can help you, you know, succeed later on. And I, I think prioritizing that, it's,

it's difficult for young people, I think,

especially because if you have friends that went to school or you have friends that are doing well, right off the bat you kind of have this like, this idea like, oh, I'm behind, you know what I mean? I'm not going to be successful because my 24 year old friend is already making six figures. And here for some, you know, local entrepreneur, making 60 grand or whatever you're making. And so you can start to think that you're behind, but the incremental jumps in income for that person are going to be so much less than the jumps in your income over the same period of time. You take like a 20 year swath. It's like, okay, well, this person might be making 100k at 24, but at 44 they're probably going to be making 180k or 200k, you know what I mean?

[Dean Matthews (Guest)]

Whereas, or maybe at 34 they'll be, yeah, right, right. Or, you know, or 30. Right.

[Travis (Podcast Host)]

The other, on the other side of that coin, you know, you might be making 60k at 24, but when you're 44, you might be on your third business and you're making 3 million. You know what I mean? Like there's just, you gotta, you gotta be willing to sacrifice a little bit of the income right now so that you can just learn as much as you possibly can. Because the only way to increase your income is by having greater skills that offer more value to either your employer or to a marketplace. And that's a fantastic way to do it, Mat. So I appreciate you coming on and sharing, Dean. That was awesome.

[Dean Matthews (Guest)]

Yeah, it was great, Travis. I really appreciate the time. Can I give. I don't know.

[Travis (Podcast Host)]

Yeah, I was going to say, where can people go to connect with you if somewhere you want to go.

[Dean Matthews (Guest)]

Yeah, you can find me on LinkedIn is the best way. Dean Matthews. One T and Matthews. Yeah. If you're a young entrepreneur or a seasoned entrepreneur, just connect with me. I love talking mentoring with younger or, you know, even older people, helping them out, spreading the knowledge. I've really kind of moved to that as really one of my primary things that I'd like to do outside of just regular work.

[Travis (Podcast Host)]

Love it. Dean Matthews. Matthews with 1T over on LinkedIn. Go connect with Dean, tell him what's up. Dean, I appreciate you for taking the time. I know you're a busy guy. Don't take that for granted. Everybody else tuning in. Remember, money only solves your money problems. But it's easier to solve the rest of your problems when you got some money in the bank. So let's start there. Here on the Travis Makes Money podcast. Thanks for tuning in. We'll catch you guys next time. Base.