The Finding That Next Gear Podcast

Beau Billington with Dennis Kirwan

Dennis Kirwan
CEO of Dymic



Episode Summary

Finding that NextGear is a relatively new podcast. And it’s really about interviewing and having discussions with high growth entrepreneurs to get underneath not just  “the  WHAT”, “the WHERE” but,  “the WHY” and “the HOW?”.


Host: Beau Billington

Guest: Dennis Kirwan


Beau  0:12  

Hey everybody Beau Billington here. Thanks so much for joining. 


Got Dennis. Dennis Kerwin, here. Thanks for joining.


Dennis  0:29  

Thanks for having me. 


Beau  0:30  

Yeah, absolutely. 


So, finding the next year is relatively a new podcast. And it’s really around interviewing and having discussions with high growth entrepreneurs, and really trying to get underneath not just  “the  What, the Where?”, but “the Why and the How?”. 


How did you actually start a company? Because a lot of times, we all have ideas. But how do you take something from inception, an idea to create in a business then actually the scaling, which I think is probably the hardest part about entrepreneurship, but we’ll get into that. 


So prior to jumping into things, you always like to start with the who? So who are you? 


You’re CEO of Dymic ( of course, and have been doing it for quite some time, about eight years. But tell us a little bit about who you are, where you grew up? And where did you come from until now? 


Dennis  1:16  

Yeah, since you asked where I came from. I’ll say that, I was born and raised in Sacramento, and then I moved to Southern California during high school actually. 


So, I think one of the things that made me who I am is a bit of a turbulent upbringing. So I didn’t have a stable household situation, or money was always tight, that sort of thing. And so, when I moved to Los Angeles, I actually moved in with my grandmother. And she was one of the more stable, successful kinds of the matriarch of the family, and someone that took me in but at the same time didn’t give me anything. 


And so she made me work for everything. So, I moved in right before I turned 15 years old, and she said, “hey, you’re, you’re about to turn 15. I’m sure you don’t want me shopping for you for your clothes, and everything else. So, if you want to buy your own stuff, you’re gonna have to get a job.”


As soon as I was legal to work, I was already working at 15 and a half.  And I started working and saving right away. I think the first lesson that she taught me was how to be responsible and how to make money and use that money wisely. It was nice to step into that environment. But, compared to how things are nowadays, it was still pretty tight. 


When I lived with my grandmother, believe it or not, looking back, it was kind of wild at the time, it seemed kind of cool. But I was living in what was really a tool shed in her backyard. So, for me at the time, it felt like I got my own guest house. I have my own privacy. 


At the time, thankfully, I didn’t feel like it was terrible. Plus, sadly it was kind of an upgrade from where I was coming from. So, it built a lot of character I guess.  I found ways to enjoy it. I enjoyed working, I enjoyed being able to have a fresh start. And I think that really propelled me into becoming an adult fast because when I turned 18, the first thing she said was “while you’re 18 so where are you moving, and where’s my rent in the meantime?


As soon as I turned 18 I had to start paying rent. And I was like, “Well, I’m gonna pay rent, I’m not gonna live with grandma anymore.” And so I quickly moved out, let’s say within a few months after turning 18 and got an apartment from a friend. The rest is history but that’s how I got down to Southern California from Northern California and stayed yonder since. 


Beau  4:03  

God it was. It’s funny to see that. 


So I started working at 15 and a half as well. Never was good at saving until I got into the latter part of my years. But I was great at spending and I enjoyed work, which is great. It’s a similar story. 


After I graduated college, a lot of my friends were moving home for six months or a year, trying to figure out what’s next. My mom was like, “hey, appreciate it, but not going to happen. Go find your own place, get your own thing and go get a real job.” And so I did that. And I think that was the big difference and where I’ve gone with my career and where things could have been. So I appreciate that segue. 


So talk a little bit about dymic. And how’d you get excited about owning your own digital agency?


Dennis  4:44  

Yeah. I think it’s one of those stories where just one thing led to another. I had different ideas and different things that I tried and didn’t work out as I was young. I think one of the setbacks of having to go beyond my own so fast was that I had to jump right into the working world. It was very difficult to get through college because I can only go part time. And I had to do that on the side and work full time ever since I was 18. So, that journey was a lot of trying to find what it is that I like doing? And where can I be successful? 


And for me, that was always a big motivator. Was not lit, continuing to live in that lifestyle. So to speak, I had it as a kid because frankly when I was young, there were times where I’m literally hungry and didn’t have clothes to wear. And I think that in a way sort of scarred me a bit where I didn’t want to ever have to experience that again


I think more recently, I’ve had a business coach and this is I guess was a few years back, and then I’ll kind of go back to where we were. But I never really knew what my big motivation was. I just said, I’ve always felt very driven, I’ve always felt like I’ve had this entrepreneurial spirit. But, I don’t know where it came from. Maybe it’s just the way I was wired or born. And that could be part of it, for sure. 


My business coach said, “I think you’re driven by fear and then also wanting to feel safe.” And so coming from a turbulent upbringing, for me, maybe I do not want to go back there. I think there’s always that grit and that drive to do well for myself and provide for my family


Beau  6:49  

Yeah, I think fear and anxiety can be a great motivator. In fact, the podcast that I have coming up is with a clinical psychologist, and it’s all about fear and how we can leverage and harness it. And it’s not necessarily a bad thing. 

But that’s interesting, and I feel like a lot of entrepreneurs have the same story as you     were there’s something in their life that happened that pushed them in one direction, so they can basically overcome earlier feelings in their lives, (i.e fear, anxiety) where’s my next meal coming from, etc?


Dennis  7:18  



It’s almost ironic because at the time that I was told that, I felt like I was very fearless. I’ve always felt like I’ll take on any challenge, I will jump in any business idea that I believe in without worry of what’s gonna happen and keep my eye on the prize. And I realized that it was something more subconscious and something that is now ingrained in me. 


It wasn’t a conscious thought, necessarily. But once she explained everything to me and I thought about it, I said, “No, I think you’re right. I think that’s where this is coming from.” So, it’s a really interesting moment and realization that, what you think an entrepreneur is or what their makeup is, can be different for everyone. But for me, I think that is the big driver.


Beau  8:11  

Sure, I can appreciate that. 


And so, on that day, how long have you been an entrepreneur? 


So you build your company for eight years or so. But prior to us jumping on, on the recorded line, you basically allude that you’ve been doing your own thing for much longer than that.


Dennis  8:24  



I have to say, I think I’ve been an entrepreneur since I was a kid. I remember when up in Sacramento at least, I remember that there was a time where the truck coming around once a week to pick up the recycled goods wasn’t a thing. At least in my neighborhood, I don’t remember that being a thing. But I do remember the time I went with my mother to recycle a bunch of cans. And I realized, wow, we got actual money for that. 

And so, something clicked in me and I thought it was a great idea. Well, why don’t I go around our neighborhood and tell people that I will collect all the recyclables and take and recycle them for them. 


I tried to make a business flyer at her work. Printed out something on a piece of regular printer and made these flyers that said, “at this time, this day, leave your recycled goods on your doorstep, and they will be picked up between this hour and this hour.” And I made it this whole environmental thing to make people want to recycle. 


I think I kind of learned that from school too, and never heard about recycling at school prior around that time. So I just put two and two together and I started recycling the cans of my neighbors to make a little bit of money. I was probably in sixth grade or something at that time. So, I think from that moment forward, I’ve always had this drive and this interest in finding ways to make a business.


That’s great. It seems like most entrepreneurs do as well.


Beau  10:01  

I think it was around 16, 15, 16, 17, I started mowing grass, which I know a lot of folks do. But it was kinda like I had this drive, this innate ability as well to go out and get business. Knock on doors and a little bit fearless. And maybe some of that fearlessness came from my grown up as well. 


But it’s funny how we all had early things that we were doing which would eventually become our day jobs later. So that’s great.


Dennis  10:31  

Your question was, how did I get to where I am now. So I think that was the beginning. 


I guess the point I was making is that I feel like I got into this industry by accident. I started working for other businesses at first, stable, more mainstream companies. I think my first real job out of high school was working for Lexus and from there I actually met one of the Lexus customers. And I think that he was very interested in having me work for his venture capital company raising money for startups. 


Looking at the car that he drove which was a nice brand new at the time, 1998 gs 400, with all the bells and whistles. I was like, “Man, if I could just have a car like that, I’d be stoked.” He just seemed like a guy who hadn’t really put it together and was doing well and he asked me what I was making there. And I told him, and he said, “Well, if you work for me, you’re gonna make at least twice that much.” 


So that was an easy decision to put in my notice and go to work for him. Him being one of their customers, I think they were happy to see me level up and go work for that guy. 


So, I got into the venture capital world and got into sales and started helping generate leads for their venture capitalists to ultimately bring clients on board and raise money for startups. As technology advanced, digital marketing became more part of the equation for the startups. I think that’s when it started to become more interesting to me. 


The last recession that happened back in, 708 right around there. I felt that I had eventually started my own venture capital company after working in venture capital for a number of years. I started raising money for startups through my own business. 


And of course when the last recession happened, people weren’t exactly looking to put money into startups at that time. People were being cautious and so things slowed down really fast. I suddenly was in a situation where I needed to figure out a way to pivot and make money because the music stopped pretty quickly in that world at that time. 


And so, one of my buddies that was still doing quite well even during the recession, he actually recommended that I reach out to this internet marketing company. They were an Inc 500, internet marketing company, specifically specializing in search engine optimization which was really a hot market at that time especially I think there was a bit of a gold rush going on in that market. 


Salespeople were doing very well there. I thought maybe it was a good fit and at the same time, I was hungry and I needed to make money. So, I went there, interviewed, got a job, and I started all over again. I started at the bottom, they made me a telemarketer. It was the biggest piece of Humble Pie I’ve ever eaten in my life. Having to go from having my own venture capital company with employees to taking a starting position at an internet marketing company as telemarketer. 


I kind of looked in the mirror and I said, “look, are you going to let your ego get the best of you? Or are you going to realize that you are where you are? Yes, there’s been a big shake up in the economy. But as you can see, they’re still people doing well. And so if there are other people doing well, you should be able to do well.


So, I looked around and I realized there are people that are making money. I started taking notes and said, “I’m gonna figure this out, and I’m going to start paving the way to rise to the top of this place.” And so that’s what I did. I just had my blinders on my nose and grindstone, started making phone calls and started getting people interested in this. 


And then I became a sales manager.  I think within the first six months. Then, I became the director of international business development, I’d say within a year and a half and actually helped them set up an office in the UK. And things are going really well. 


So how did I get to the point where I started my own company after that? It was a big Google algorithm. And that company was a company that was specializing in SEO. And that was really the bread and butter. And Google decided to do two major algorithm updates back to back, which were known as paying Penguin, and panda back and circa 2011, 2012.


Beau  15:28  

I think they did another one as far as I understand.


Dennis  15:32  

Yeah, they’re doing them all the time. 


I actually just got done grinding out a very long article that I submitted to Forbes, which will probably go live in about a week. Again, it’s all about the latest Google algorithm which is called “its core web vitals and page experience update.” So they do these pretty often. If you’re not prepared and don’t keep your finger on the pulse with Google, it can really be a painful surprise. 


Now, in the defense of my old company, this was a time when Google was operating a little more of a black box. So they had a guy named Matt Cutts that worked for Google that would once a week do these kinds of video blogs and talk about what Google’s looking for. But he was always vague, and never really told you exactly what the ranking factors were, probably because they didn’t want people to know the secret sauce and try to gain the system. 


Over that year of the two major algorithm updates, my prior company started to have some trouble. They were suddenly in a position where they were losing clients, clients were losing rankings. 


As somebody who really cares about my clients and the people that I bring into a business endeavor or people that trusted my advice and guidance to do marketing, for me it didn’t sit well with me. I immediately started thinking,  this is a great company. They were very good at what they did, they got to a 500 status. And something like seven years, five years, something like that. 


They were doing great but the pivot isn’t happening enough, at least for me. And so I started to think about maybe there’s a way to build a better mousetrap. Maybe there’s more to marketing than just SEO. And I already kind of knew that from working there and people asking me about other services, whether it be social media marketing, or web design. There were just certain things my company didn’t do at that time. And I felt like it was a missed opportunity. 


I guess it was a tipping point where a couple of the other leaders had already left the company and started around. And at some point, they invited me to join them and to work at their company. So, we basically became partners. 


I put in my notice for that company. It was tough. I really admired the CEO there. He loved me working there. I was a very important part of this company, and he didn’t want me to go and tried keeping me longer. I just felt like it was time for change. So I felt bad because I really did like him and like the company, and I enjoyed working there. I’m a loyal guy, so it’s very difficult. But, we decided to get our company going and I put in the proper notice there, and said, “hey, let’s try to be that end to end marketing agency that people seem to want.” 


It was becoming clear to me that a lot of people out there with businesses had fragmented marketing campaigns. They were working with multiple vendors. It was just getting messy. And I said, “let’s help people clean up that mess and bring it all into one place.” 


That was really our sort of mission at the time. We really strive to do that and have to knock down one service at a time and master it. The first couple years of our business, it wasn’t all sunshine and rainbows. We were very fortunate to score a big account early on which helped fund a lot of our ideas. But that client didn’t stay forever. And when they left, it was a bit of a wake up call because we had built all these different departments and things and suddenly there was a massive loss of revenue just after the first year of being in business.


Beau  19:40

Just energetically, I think it’s one of the biggest mistakes that entrepreneurs make. And I myself made that same mistake, the first two years of my business where at one point I had like, 70% of my revenue coming from one company. And if that  70% dries up, that’s a significant loss. You can’t live off 30%. 


I think one of the things that entrepreneurs need to do, especially budding ones, is ensure that they’re hedging. Don’t have all their eggs in one basket and make sure to diversify the customer portfolio because things do happen, COVID happens, companies go out of business, they get acquired, leadership changes. And it happens all the time. 


Beau  20:18  

I think that’s a good message that you put out there in the ether because a lot of people get caught that way. And companies go out of business because they just invest too much around one account.


Dennis  20:30  

That’s exactly what happened. It sounds like we had a similar experience there. And it certainly was a learning opportunity. 


And anytime we make a big mistake in life, in general, that’s what we have to do, right?. We have to just learn how to do things differently next time


Beau  20:47  



Dennis  20:49  

That’s unfortunately exactly what we did, we had kind of all our eggs in that basket and we didn’t think they were going anywhere. We’re really focused on trying to make that client happy and we weren’t focused enough on getting a lot of other clients and diversifying. 


That tunnel vision unfortunately blindsided us a little bit early on. But as I said, it was a wake up call and we were able to thankfully we had put some money aside from that campaign and we were able to grind it out. And I think that was one of those moments where I wasn’t sure if I made a mistake by starting my own company. Truth be told, that was really my wife now, she wasn’t at the time. But we had been together for some time already. And I was kind of venting about how difficult things were. And maybe I should go back and work for somebody else. And she talked me out of it. 


Beau 21:03

You don’t hear that often. Usually, it’s like, “yes, please, this is too stressful. I want a stable paycheck, please go back to corporate America.


Dennis 21:58

Yeah. I think in fact, when we got married that was one of the things I vaguely mentioned in our vows that moment because she believed in me more than I believed myself at that time. It was nice to have someone that has your back and gives you that reassurance and reminds you, “Hey, you’ve accomplished some pretty impressive things over the years. And you should have the confidence to get through this. I think it will pay off if you stick it out“. 


And from that moment, that’s exactly what I did. I said you know what, “I’m not going to just give up when the times get tough here, I’m going to stick this out. I’m in control of my own destiny now with my company. And I need to prove that I can do this.” 


We really worked hard for that year following the loss of that big client and did diversify, did get many clients all over the country and all kinds of different industries. Cast a really wide net, built a sales team, and experienced a nice, steady seven years of growth every single year until COVID happened. And that was where things started to get a little turbulent again. But I’m happy to say that, we’ve stabilized and got through that which was another big recent challenge we had to get through like many people.


Beau 23:24



I think that entrepreneurship is that, kind of like getting into a house of cards. I’ve been in business for four and a half years, almost five years. I’ve got a client base, life’s relatively good and we’re stable. But, you never know. I mean, COVID was a huge wake up call for me. I think for about six or seven weeks straight where literally I couldn’t get customers to answer my calls. Even customers I’ve been working with for two years. 


Beau  23:47  

So you just never know what’s gonna happen. And I think part of that though is perseverance. So you gotta get up every day, you got to work every day, and you gotta fight every day. And that’s really the best way to get through situations similar to COVID, or losing your biggest account. 


Dennis  24:03  



Beau  24:05  

So, you’ve been in business eight years, you guys have an end to end digital agency, what is your role now at the company? I realize you’re CEO but that’s a bit nebulous. Are you kind of a number one, business development individual? Are you kind of the face of the company? Are you working on ops? Like, what does your role look like now?


Dennis  24:23  

That’s a great question. I think it’s a little bit of a mixed bag. 


As probably a lot of midsize companies experience when you are working full time for your own business. You end up wearing a lot of hats. And of course, we’re striving to always make that as organized as possible and more siloed. 


I think one of the pitfalls that many businesses run into is they get caught up in too many different activities, and they can’t really scale up because of that messiness. So that’s really been I think the last years since fallen COVID. One of our focal points is, strengthening the foundation and making sure that we’re highly organized, and that we know what the duties and responsibilities are of the other partners. Because I do have two business partners. 


I think the first six years or so we’re in business, we’re really shooting from the hip a lot of the time. Just kind of roll with the punches and grind and run a company and doing pretty good at it considering more or less sales managers from another company that started a business together. 


All of us have their own life experiences and business experiences. But we weren’t formally groomed to run a marketing agency. I guess you could say, we had experiences that came in handy. But there was still a lot to learn. A lot that we did learn is as we were getting going. 


Fast forward now, right before COVID started, actually, we hired someone that was originally consulting our business, and later we made him our COO. And he was able to be on the outside and look in and say, “here where you guys are falling short, here are the areas that you need to improve.” And he was very good at laying that out. He made what’s called a “State of the Union speech” and dissected our company, put it under a microscope and told us where our shortcomings were, and where we can improve. 


It was a tough pill to swallow to hear some of those things. But at the same time, that’s how we all get better. You find out where you’re making mistakes, and you try to improve. That’s what we did, and it’s worked out quite well. We’ve become more integrated. We really want to be able to practice what we preach, and not only help people with their online marketing. 


They’re integrated marketing strategy. But in order to really effectively do that, we have to accomplish that and be good at it ourself. I think that this past year, especially with how rapidly things are changing, and how fast technology is accelerating into just a completely different dimension, we have to sort of keep up with this light speed of change, and dial in our own business. 


And so, we really have focused on that this past year, and are now confidently offering those solutions. Actually just this past month, we started ramping up our own online marketing campaign after we launched our new website with all the new web copy that speaks to the challenges that businesses have experienced this past year, especially. 


So I’m really excited about this next chapter in our business, I feel like we have a much better Foundation, and we’re ready to help people, drive and then in the new normal that we’re all living in. 


Beau  28:10  



I think you probably get the point. It’s all about knowing your identity, and knowing what you do, what you do well, what you don’t do well, and maybe what you shouldn’t be doing. And I’ve been in business for four and a half years. And I think just within the last month, I had had an epiphany in regards to my company’s identity, and where we need to be in the marketplace specifically. 


I’ve been dead set from that point forward on where we’re gonna play it. I think it’s really important for any company that is going to grow is distilling it down to the things that you do well, and putting a bit, creating a business around that, and productizing that if you will. When I first started, we were more kind of like a jack of all trades which is a master of none. And that’s also really hard to articulate. It’s really hard to come up with a tight value proposition if you do everything.


Dennis  29:00  



Beau  29:01  

So, I think it’s really important to again, know your company’s identity, what you do, what you do well, and of course, eat your own dog food which it seems like you guys have begun doing which is important in your space. Right?


Dennis  29:10  

Yeah, that’s right.


Beau  29:13  

Also a couple other questions. Just jumping in here. 


You mentioned that when you first started a company, you had some partners and you explained pretty clearly how that came to be, which is great.


You also mentioned that you were lucky enough to find your first account, which is a large account within the first year. What that looked like, I mean, would you leverage existing relationships? Did you get lucky with a cold call? And what were you doing prior? How were you floating the business prior to landing this account? And how do you expand from there?


Dennis  29:44  

Yeah, I would say at the very beginning, there was a lot of self funding. All three of us were making pretty good money at our previous company. And we were able to pivot quickly enough to where we didn’t start experiencing at least a detrimental degree of the loss of that good income.


It certainly started to dip before we left and we were able to put our resources together to start the company, and very early on, one of my business partners had a business connection through another person that he knows. And they were able to bring the opportunity to the table for us.


Because we all have sales backgrounds, myself, my two business partners, I think that really helped us facilitate the deal. We were at a place where our company was very new and which made the sales process even harder to convince a large national franchise to do business with when you are so new. Takes a lot of salesmanship, I guess you could say. 


But, we were able to put together a very compelling proposal and they liked us. They decided to give us a shot. We’re very fortunate to have scored that deal very early in the development of our company. And it certainly helped fuel and propel us into the next chapter of our business. I think without that deal, we probably wouldn’t have been able to survive.


Beau 31:28

Yeah, I totally understand. And I’ve been there as well. I think it took me seven months to find my first customer. For a long time, I did relatively well. 


Prior to jumping out, I built a house, had my second kid, married, and then I decided to get out of corporate America. You gotta find success quickly. And it’s a very, very nerve wracking situation. I think most people don’t and can’t grasp what it’s like. No paycheck coming in.


Beau  31:58  

And then once you get a customer, you’re still depending on their payment terms, net 30 net 60. Maybe you don’t get paid until projects are complete. It’s a hairy situation. But then you get the first customer and it’s like, “Alright, we did this, rinse and repeat.” You basically have tried to replicate that model, and then go find other customers in the marketplace that did similar business.


Dennis  32:19  



I think that is one of the things that a lot of people find outside of their comfort zone. I don’t think that everyone wants to, or has the ability, or however you want to put it. The grit to grind through dry moments in a business are tough times.


And in our case, we’re in sounds like you may have experienced this yourself too. There were several months where not only was I not getting paid and working my tail off. I was actually taking money out of my IRA accounts and putting it into the business and paying the penalties of cashing that out prematurely. That is something a lot of people would just not do. And believe me, it is much more comfortable working for another business than it is running your own business.


Beau  33:19  



Dennis  33:20  

I think a lot of people like that feeling of comfort and safety and I don’t blame them. I certainly miss the ability to just be able to punch out at the end of the day and not think about the business. And I don’t think I can do that anymore.


One of the things I’d say, running a company is that feeling of not being able to, at least me, I feel like I can mentally check out and I just always have it on my mind. So it has its pros and cons of running a business.


Beau  33:54

Yeah. There were a couple of those. 


There’s a false security with that. And I think COVID showed us better than anything. But you’re not necessarily any safer, right? 


I mean, yes, you have a weekly recurring paycheck but, you can still get laid off. Right? And I had a similar situation as well, where I leveraged some IRA to just for the first few months to keep things going. I promised my wife no change in lifestyle which is probably not a good decision. 


I was in the same situation, same boat, totally get it. And also when you’re not finding success, you’re wondering, “hey, is the business model flawed? Am I flawed? Was my hunch incorrect?” All these things are going on behind the scenes. And it’s a pretty interesting situation.


Beau  34:42  

But again, you find a little bit of success. And you really need to sit down and figure how you can turn that little win into more wins


One thing that I’ve seen with regards to entrepreneurship is the biggest trait and I’d love to hear your thoughts on this, but perseverance.


I think that perseverance has kind of helped me stay in business and get past those three, four extra muscles I needed to start my company. When I first started, I really thought that it was gonna take me three months to begin getting revenue and then within eight months I replaced my income and oh man it was far from that. Perseverance is what made me get to the place where I am now because I never gave up and kept fighting and digging for gold


So what do you think is the number one trait for entrepreneurs that find success versus those that don’t?


Dennis  35:30  

I think that could be it. I feel like just having that drive and the tenacity and the willingness to continue to grind. Even when you might not be finding the oil that you’re digging for, or the gold that you’re looking for.


You’re just digging and digging, and it’s just not happening. And to get through that it’s a mental battle. I feel that maybe it’s my life experiences that I had where I went through some pretty crazy times in my childhood, possibly, that’s what I guess molded me into who I am. 


I was able to get through it perhaps because of that and maybe for other people who had much more stable upbringings. And maybe they’re even wired differently, they just don’t want to stomach or maybe they just don’t have the desire to go through that. It’s certainly a choice.


In my case, I could have continued working at the company I was at or got a job somewhere else. And I suppose that would have probably been easier. I’ve always had this drive and this desire to run my own company, as I mentioned earlier, ever since I was young. So I think that’s where that came from.


Beau 36:56

Yeah, me too. 


And also, you have to just embrace the suck. I mean, you mentioned earlier that you wish you could turn it off and you feel that way sometimes. But I’ve also come to the realization in conclusion that this is the path I’ve chosen. 


When I go on vacation, if I’m gonna go out on the beach and just pick a random day, a Thursday, I’m gonna need to pick up my iPad or get on my phone and go through some emails for 30 minutes before I reach that level of comfortability that I can walk away.


First of all, my company has struggled with that because I wanted to be able to completely unplug. That was one of the reasons I wanted to start doing my own thing. But then I finally realized that’s not the path that I chose, right.


And so ever since, I got to the realization that was not going away and I’ve been able to embrace it. And that’s part of it. I’m going to vacation tomorrow for a few days and bring an iPad and I will be doing some work. So when I get back to work on Tuesday, my inbox is small, and I don’t have a lot of catch-up, just part of what we chose.


Dennis 37:52



I suppose folks like us that are running a company have a similar mindset. It’s less stressful to just check the email for 30 minutes than to think what’s going on with my business and just “No, I’m not turning on any devices, today. I’m just gonna relax on the beach.


Well, it sounds like we might be in the same boat as me where you can’t really relax unless you feel like everything’s under control. So I’m the same way. I think I’ve gotten better at it. Probably you do with taking a vacation and being able for the most part to enjoy and focus on spending time with my family or whatever it is I’m doing and try to shut that off.


I always leave the line of communication open in case something comes up that needs my attention. But I think part of growing a business is to get to a place where you can rely on others, and where you can get people to have your back and for the most part, keep the gears turning while you’re not there.


And I think that’s something that we’ve improved on for sure over the years. But it doesn’t mean that we can completely turn it off, right? So I feel like on that one, I’m kind of in the same boat, I’d say check the emails maybe in the morning, then maybe at night and then have my phone on just in case. 


Beau  39:14  

Absolutely. Yeah. It’s what we signed up for, unfortunately. 


So if you could go back to younger Dennis and give yourself one piece of advice, prior to starting your company, or would that be what would you have done a little bit differently?


Dennis  39:28  

Not take things for granted


And specifically in this case, I’m referring to that large client that we had. I think that we were  almost borderline fat cat syndrome pretty early on from that client and felt like we just had this blind confidence that they’re gonna stick around and then we’re going to get other companies like them. I think that it was a very humbling experience to realize that they can just leave the contracts up and then what are you going to do then? 


If I could go back in time and sit down with myself, before we started the company, I would have said “don’t take things for granted as soon as you’re going to lose that deal, what are you going to do when you lose that deal? And then while you have the deal, what are you going to do to stabilize the company and make sure that it’s not going to rock the boat when they do leave? 


I don’t think we were thinking that way. I just feel like we were fat and happy, so to speak, and just really enjoying that deal. And focusing on that client and nurturing that relationship. One of those things happens where you just don’t know what’s going to happen. What happens when that relationship you nurtured is with somebody who leaves that company? So I guess you don’t know what you don’t know. But we didn’t see that coming. We didn’t think about it. 


And running a business is certainly a chess game. You have to think multiple steps ahead and plan for the worst. As we can see, especially with this past year, you just don’t know what’s going to happen. And you have to be as prepared as possible. And sometimes that’s still not enough.


Beau  41:11 

That’s great. That’s very sage advice. And I kind of had a similar situation. It’s funny how there’s similarities. We do different things, we’re from different places, but there are a lot of similarities in our stories. 


I had like my second or third client and they’re big for me especially they got acquired six months into our relationship by a very large company which I knew would preclude me from having a relationship with them. So I was out. 


And the big learning experience for me was that you always continuously have to be hustling. Always have to be hustling, always looking for new business, new relationships, because those situations will present themselves. And then conversely the flip side of that is that, sometimes you have to fire customers. I had fired two customers in the last three weeks. 


I no longer fit the mold in regards to what I expect out of a partner bond. Again, so you need to be hustling and you can’t take relationships for granted because they change. Be it on their own side.


Dennis  42:12 

That’s right. Yeah. 


I think we certainly learned from that. Ever since then, believe me we’ve been grinding in even though we’ve experienced nice growth for seven straight years. We still work hard. And I think we were all a little bit damaged from that experience and knew that anything that happened in new time and I feel like we all worked harder after that moment. 


Beau  42:42

Absolutely, it’s very interesting. 


And again, just in recent days, I’ve had a few things fall out of the sales funnel that we’re just about guaranteed. So, you never know. And if you don’t have enough, I don’t say residual, but enough things kind of in the hopper of the funnel. That’s really where you expose yourself.


Dennis  42:57

Yeah, it’s an old sales tactic too. To not, when it comes to business development, get so focused on one deal you think you have or one hot lead. It’s all about continuing to make sure you have a full pipeline so that if one falls out, it doesn’t emotionally wreck you that you lost that deal, right?


So, we’ve gotten really good at that too, just trying to make sure that we have a steady flow of leads coming in at all times. We always have new business. And inevitably, some people are going to back out or it’s not going to go through and that’s why it’s important to keep that lead generation going. And to keep that pipeline full.


Beau  43:40  

Pipeline or no pipeline still be a bit tough to stomach. That last week, I had a couple of things that were pretty significant that just kind of disappeared. They were sure things and it still hurt even though I’ve got the full funnel and I’m not too concerned about them lacking or not being in a revenue number. It’s still hard. 



For sure.



Well, I do personally a little bit.


Dennis  44:06  

I felt one of those this week. So I know. Believe me, I guess I’m not completely callous but I still feel it a little bit too. I think I’ve gotten better at it taking those punches to the chin but yeah, they still sting a little bit for sure.


Beau  44:20 



So let’s get to the lightning round here. Just gonna ask you a few questions, real quick. Burn through them. 


So what’s your favorite aspect about being your own boss?


Dennis  44:29

I would say the feeling that I’m in control even though that’s probably not real. I’ve learned through a lot of life coaching and stuff like that over the years that my desire to feel like I’m in control is from not having a lot of control. When I was younger, it’s funny because I’ve traveled a lot. I’ve flown all over the world and done things right. But I still am not comfortable on planes.


Part of that reason is because I am not the one with the steering wheel. So I feel like my fate is in someone else’s hands. And I really don’t like that feeling. 


Logically, planes are super safe. I mean, they’re way safer than driving. Yet when I drive my car, I feel like I’m in total control. I feel very comfortable.


Beau 45:20

No anxiety. 


Dennis 45:21

Yeah, none. I feel great. I love driving. I don’t like flying, but I fly all the time. I just flew again last week. So I mean, I do it. And I get through it. Because I know it’s my own problem.


And strangely enough, I feel like maybe that’s one of the things I love about running my own company is I don’t have that kind of looming anxiety of like what’s going to happen. It’s just I feel like I have this. I’m in control of my own destiny is how I feel. Whether that’s true or not, that’s the feeling I like running a business.


Beau  45:55

It doesn’t matter if it’s true or not, right? Whatever keeps you going. 


So what’s your least favorite part about being your own boss?


Dennis  46:02

Kind of what you were talking about. 


I find myself having a difficult time. At times where I should check out and should turn off and not think about the business. And it could just have been a really heavy day at work, a lot of stuff happened. And I try to go have dinner with my family and sometimes it’s hard to focus.


Beau  46:25 

You’re like halfway there. I’ll tell my wife sometimes she was like, I need 10 minutes. Just give me 10 minutes. Let me finish to tie this thing off but I can be with you guys. Otherwise, you’re gonna get 50% of me, and nobody wins. 


Dennis  46:38

Hey, that’s good advice. I should probably try that out. 


Sometimes I just get from my mind wandering a little better at checkout. And someone might notice that it doesn’t look like I’m 100% focused on being present at that moment. It’s definitely something I’m becoming more aware of and working on. But I would say that feeling of not being able to turn it off or check out. I didn’t have that feeling before when I was working for somebody else. I felt like I was able to go have fun and do whatever not think about it. And I think that’s the one thing that I’m not a huge fan of. I’m trying to get a better handle on it.


Beau  47:14

Same way like when I worked in corporate America to go play golf, completely relaxed because I was off and they knew not to disturb me. And now if I go play golf, well, usually the busiest day for whatever reason is just how it works out. I’m busy, I’m getting calls, things are blowing up. And it’s less enjoyable. But again, it’s part of the plight of the entrepreneur who signed up for.


Dennis 47:37

A similar life in that regard with golf too, by the way. 


Beau 47:40

What would you consider your biggest success?


Dennis  47:45

I’d say the biggest success, the first thing that comes to mind is that the big account we landed when we started the company which I guess you could say is also our biggest failure was losing that client. So I would say, that’s what comes to mind first but I think more recently just being able to get through another really turbulent, uncertain time this past year and still be able to keep our head above water and run a business and help other people also keep their head above water. And I feel very good about that. And that gives me a sense of accomplishment. 


That stability of feeling like I can get through anything with a business. So that I would say more recently is a big sense of accomplishment that I’ve had with the company.


Beau  48:31

I think that’s great. I think it’s a great perspective to I feel most companies do if you can make it through situations just COVID. Like, you’re golden. That’s the way that I’m kind of treating this whole thing like revenues were up this past year. Not as high as I thought they would be and as high as probably they should be but made it through. If I can get through that crap, not even worried about it. 


So I was gonna ask about your biggest failure. But I think you’ve alluded to that a couple times about losing your biggest account. It’s bound to happen to any entrepreneur out there, it’s happened to me, happened to you. Now, it’s kind of old hat to be honest with you like you’re gonna get accounts and things are going to happen, people are going to leave, etc. 


Beau 49:13

I would say the hardest part about having your own business is the inability to unplug? Is it kind of stressful? Like I’m up at 3am almost every day. What is the hardest part?


Dennis  49:25 

It’s funny you mentioned that because I woke up today at 4am with no alarm. And I went to bed at 11. 



You need more sleep.



I do. I usually get six hours. And I feel like that’s enough sleep. Maybe it’s not. 


I think that’s one thing that’s been tough too with so many things on my mind. And that comes from the business. It just really occupies your brain a lot of the time. And I feel like that’s what keeps me up sometimes at night and what makes me rise early. 


I just have all these things that I know that I need to do, or take care of, or goals, or things that we’re striving towards that I’m just really eager to accomplish or achieve. And so, because of that you don’t sleep like a baby at night, at least I don’t and get maybe the needed eight hours of sleep or whatever it is. I know it’s totally different for everybody. But I probably use more than five to six hours of sleep a night.


Beau  50:26 

I’m the same way. What I’ve started doing and you’ve been doing this thing longer than me. So I should probably take any advice from you. I’ve put a notepad next to my bed. Of course, my phone in the blue lights off. And if I come up with an idea, or something goes through that needs to be taken care of, I’ll just go ahead and just pony up and write it down.


That kind of allows my mind to escape a little bit. Most of the time I go to sleep and that doesn’t happen every night. As you know sometimes too you’ll be dreaming or something will happen. You’ll just wake up like, “Oh, man, this genius. I have to try this tomorrow.” 


And then then it can be kind of comical looking back at your notepad about what we wrote down. It’s completely nonsense. I’ve tried that and it’s been helpful for me. So it’s great man. I really appreciate you joining us. 


In closing, where can people find you and find more about you?


Dennis  51:10

Yeah, so our website is That’s D Y M I C dot com kind of like short for dynamic, it’s not a real word. But that’s the website URL. 


I would say that’s the primary place. I’m also a contributor on Forbes. So keep an eye out for my articles. I try to get them out there about once a quarter. I do have one coming out, supposed to be in the next week or two. And if you have any interest in what Google’s doing and their search algorithm, I spent a long time writing that article more than I’d like to admit. And so there’s a lot of good information there.


Beau  51:49

Awesome. I really appreciate you taking the time today. Sincerely, I appreciate it. You know, we’ll put up your information so people know how to find you. And keep fighting the good fight, man. 


Dennis 52:00

 Thanks for having me. There’s a lot of fun. 


Beau 52:02



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Dennis Kirwan

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About Beau


Beau spent over 14 years in enterprise-level software sales and was exposed to high-level talent by working alongside companies such as Apple, AT&T, Amazon, Coca-Cola, and more. 

In this podcast, Beau aims to interview high performing business leaders in the hope that their insights will bring about real change positive change the businesses of his listeners.

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