#64: An interview with Dave on career path, joining a startup, side projects & more

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Two, three, four, exit, exit, exit. Hey, it's Dave. Just some quick context before we get into this episode. This is a conversation that I did with an old friend and colleague of mine, Dave Charest. He works at Constant Contact. That's a company where I started my career at probably a decade ago now. And he asked me to be on this podcast. But after doing it, I realized I told a lot of stories and shared openly about a bunch of different things earlier in my career that I hadn't shared. And I was like, man, I want to use that audio. I want to put that somewhere else. And so I thought it would be interesting and just some good context and it was a good conversation and I want to run it here. So here it is. This is Dave Charas from Constant Contact interviewing me, which is a fun conversation. I hope you enjoy it. See ya. Exit.

Dave, you were mentioning that, you know, we've worked together in a past life. I think you were. We're both at Constant Contact from, I think, like, what, 2011. Were you 2011 to 2013? I started in 2011. I think you were there through 2013, right?

Yes, that sounds about right. What a time in my life that was. Holy smokes.

Amazing. And you were doing. I think when I first started there, you were in the PR world, right? And then you moved over to product marketing.

Yeah, that was my first, like, actual tech company. That's how I got into sas, actually.

And.

And this, this kind of world was. I was At a PR agency. So graduated college, shitty time to get a job. Didn't really know what I wanted to do to do. Got a job at a PR agency, and I was there for a year and a half, and I was like, I'm kind of good at this thing. And people were like, maybe you should try to go, like, in house. Because if you go in house, you can learn at a company, and you might get paid a little bit. Like, you might get a nice pay raise. Relative to what I was. I was making, like, you know, I think I was making 28 grand. My PR internship. It's all relative. And I got. I applied to Constant Contact. And I talk to this day, I talk about that time in my life was so informative for, like, what I ended up doing now. And I didn't see that path because, like, I learned about SaaS, I learned about tech. I learned about being inside of a company, and they were making, like, a bunch of acquisitions at the time, and it was just a cool time to be there. And I look back on that now, and I'm like, yeah, that actually was a really formative part of my career that I don't often talk about with people. So I was like, when you reached out to talk, I was like, hell, yeah, let's do it.

This is cool. So I want to share what I have in my head, which I know it probably isn't the case, but I want to share my Dave Gearhart kind of origin story that I have in my head that I think would be really cool, if you don't mind.

You ready? Oh, boy. Buckle up. Yeah, I'm ready.

Yeah. So we're talking, right? We both work there, and back in the day, we used to do a podcast, and we had you on every once in a while. We used to do the Speakeasy Marketing roundtable. And so every Friday, Constant Contact used to do a beer cart. So we'd grab a beer, and then a bunch of us would sit around the table, we'd have a beer, and we'd talk marketing. And I can remember your manager at the time and kind of being like, that's just waste of time. Why are you wasting your time doing that?

Right?

And so I have this thing in my brain that you were like, oh, yeah, I'll show you what a waste of time is. And you've kind of built your whole career around, like, starting podcasts everywhere you went, right? And, like, this is kind of good going. So this is my secret origin story story I have for you in there.

But oh, man, that's so funny. You just brought up a memory that, like, that I know exactly what you're talking about, right? And I remember, like, like, yeah, shouldn't you be doing something else? Like, are you. I actually feel like that came from a position of, like, if he's around these other people that are outside of his core job function, he might get interested and there might be other things. And learning this lesson now, I think, like, if you have people on your team that are, like, hungry to be involved in other parts of the company, sure, there is some risk in that. But I think overall, you like, we built relationships, we had chemistry. Like, I got to know you. We all worked on different teams and ended up like, we're having a unique working relationship together. And I think you learn a lot. I learned, hey, this is cool. I like this format for myself personally, and I might go do something like that. I just think you have to give people the freedom to go and do those things. And there was a bunch of cool people there who were, like, just doing those things, and they were like, hey, dude, you want to come in and chat, like, with us? I was like, sure, that sounds awesome. And yeah, that is cool to look back on.

We mentioned a little, little bit before we started recording how, you know, I'm kind of always kind of watching, seeing what people are doing. And you're one of the folks that I think really puts it into practice. And it's at the airing on the side of like, taking action versus kind of waiting for perfect and doing all of that. And I used to talk a lot when I was wearing my content hat, really, about how content marketing is both internal and external. You have to be telling the story and you have to be getting people activated and you have to be doing these types of things. And so I wonder if you can just kind of take us through that journey.

Right.

So, like, obviously, you started Constant Contact, like, what I guess led you down that path of, like, what's your history? And how did you get to where you now have your own business, which.

Is exit 5 connected to constant Contact for me in this story, and this is cool because I'd never shared a lot of this before, and I'm starting to reflect a little bit more as I think about what I'm going to do next and all these other things. And I think being at a company like Constant Contact, I got to meet a lot of more entrepreneurial type of people. And I saw that for the first time in my life, I think, like, work, and I wasn't that old. So I can't say like, you know, for the first time in my long, long life, but like early on in my career I saw people that like, had a kind of like related work passion, but it was outside of work. And so it might be like they worked in social media. And social media was really blowing up industry at the time, right? Like, Erica's team was such a core function of like that kind of world and, and Constant Contact had a big social media presence and that was a huge lever of their growth. But I think through that world, through social media and through marketing and through tech, I started to see these people kind of talking about what they were doing in a work related context, like outside of work. And so they might have a blog about social media or they might have a YouTube channel or a newsletter. And I thought it was cool to like be inside of a company and do these things in my job. And then like, I found myself like wanting to. I was reading, I was early reading. You know, I was into like RSS feeds and early podcasts and I was already trying to follow, you know, it was such an interesting space being in social media in that time, like 2011. It was like, it was like early Gary Vaynerchuk, Chris Brogan, Brian Solis, like all these people in this kind of social media world were like blogging and I just remember all these people's names and they started sharing stuff and I, I thought it was cool. Like there was like, what I happen to be working on. I was doing PR for Constant Contact social media products. And so I had to like, pay attention to TechCrunch and learn what things were launching. And Constant Contact had acquired a company at the time called Nutshell Mail. And I got to work really closely with this guy, Mark Schmulin, who was an entrepreneur and sold his company and I got exposed to like world through him. And so early on I, I had this feeling of I wanted to start a blog or something of my own, talking about marketing, because I saw all these people in, in my work life talking about marketing and they kind of had their own things. And I was like, I got things to say, I want to do this too. And so I remember it kind of like the beginning of it was really wanting to start something, wanting to start a blog or start a newsletter. But I kind of like had a little imposter syndrome and didn't feel very credible yet. And so I kind of held off on doing that. I didn't fully execute on that until like I went to start My Tech Boston podcast a year after I left Constant Contact. But it all connects back to me. I remember specifically being at Constant Contact, being like, man, I should start a. A marketing blog or whatever. But I, I don't feel like it's right for me right now. And I, I was kind of embarrassed by it. Like, none of my actual friends are going to think this is cool. And now I've kind of just been able to scratch that itch. And I guess there's something deeper down where I like, I like creating things, I like pulling things together, like having an idea and being like, oh, actually, you know what? I could do that and sign up for a landing page tool and sign up for email and write the copy and get the page published and get the domain and get traffic to it. Like, there's something in there that I guess appeals to me as a creative and competitive type of person. And I think having my own blog was like a. Wanting to do that was a way to also scratch that itch. And then as I progressed in my career, I actually went to early stage companies where I got to kind of do those things. They're like, hey, you've never run a website before. Like, Constant Contact, it was like, do not touch the website. Like, yeah, such a staple of the business. And there's, there's a team of people that work on the website and there's like 20 people on that team, right? And then I go to a company, we're like, oh, you've never run a website before? Sure, why don't you run our business website? The core function of this freaking company. And that was cool because that, I guess to me that's at least like how I've needed to learn is like, by doing. And so then I got to like go to startups and take this idea of wanting to start a blog and start a newsletter and apply it to a company. And so I'm launching Content Strategies. Looking back to me, it's just, I can say the word strategy now, but it's like, we need some traffic, let's start making content. And you build a strategy as you go. But that's kind of always been a staple. And I guess I got to do it at bigger stages, like versus my from myself to Drift and some other stuff. And now I actually am doing a really similar thing with what I'm doing with Exit 5. There's a website, there's emails, there's social media, there's podcasting, and I just get to do it all. And I think that all stems Back to that time at Constant Contact.

You mentioned something in there. Imposter syndrome. I think it's something that all people go, I was gonna say business owners, but I think just people in general.

Right?

It doesn't matter what walk of life or what it is that you're doing, whether it's just your everyday 9 to 5 or whatever the case may be. And I mean, I would say I've been doing this for a while. Like, I still have it. There are times where I'm just like, I'll create something. I'm just like, ah, man, this is not good. Like, nobody's gonna like this. Like, like, do you still feel that in your day to day? And there are other times where I'm like, no, I'm. I'm really good. This is awesome. Like, you know what I mean? But there are other times where like that self doubt comes in and so.

Like I'm literally going through this as we speak. Like, okay, so I've been wanting to start my own podcast, Chalk. Okay, if I have many.

Wait, you do you do podcasts?

No, but I've wanted to just like have like the Dave Gearhart podcast and just talk about like whatever I want to talk about. Like, I like this format and I have learned so much, like through interviewing people. And this would be separate from like marketing stuff. Like I don't work for a company now. I can just kind of do whatever I want. And I'm like, you know, I'm just, I want to make the podcast that like my friends or my wife and my mother in law would listen to. Right? And I was like all set to do that. And then I kind of just like was like, there's so many podcasts. Why would someone listen to me Again? I already have like Exit 5 podcasts, which is marketing stuff. So I go through it all the freaking time. Like, and I found that the only way through it is to like make some progress on something and chip away at it. But oh my gosh, I have it. I have it all the time. Every day I have it. I have like, is exit 5 going to be like too big? Is this too big of a. Like a. Is it generating too much? Like, am I, can I manage this like myself? Like, is this real? Did I fake my way to get here? Like, I really. Every day I have that conversation. Like, is this real? Can I do this? So hell yeah. That's just a part of human nature. I feel it in many ways. I love golf. Golf is my favorite sport and I play golf sometimes and I'll, like, enter in a tournament and I'm on the first tee and I'm like, dude, what.

Are you doing here?

Like, go to work. Go to your real job. And then I go to my real job and I have imposter syndrome there. So I think it's a natural. Must be something how we're wired.

Yeah, totally. I remember hearing a story of Anthony Hopkins, you know, the actor Anthony Hopkins, and having a conversation with somebody else and, you know, asking how things are going, and his reply was like, well, they haven't figured me out yet.

Right?

Like. Like he has no idea what he's doing. Like, you know what I mean? And I think I remember a key moment in kind of my life cycle, career, whatever you want to call it, right? Like, noticing that, like, oh, everybody's kind of winging it in some instances.

Right.

And so I was just going to say that, like, I was just going to say the other thing that I learned with that matches with that is like. And I don't mean this as disrespect to anybody, like, absolutely.

Yeah.

I've been in rooms with, like, some very successful people, way more successful than me, and I'm like, they're kind of like, they don't really know everything. They're kind of winging it too. Or like, I've seen really successful people, like, admittedly wing it in moments, and I'm like, that is so liberating to see also. And so, yes, I think there's going to be people who are just natural at X and they don't ever feel it, but I think for the rest of us, it's always going to be that way. And I think once you realize that other people are not that great, then that makes it a little bit easier.

Yeah, I think the key lesson for people listening here is just like, figuring stuff out. You just got to do it. And it's through that doing, you learn what you're good at, what you're not good at, and kind of where you got to fill the gaps, right?

Yeah.

And I found early on, if you just come in. Okay, like, so most people don't really know. And so if I could come in with a plan, people would go, like, okay, yeah, that sounds good. Let's do that.

Right?

And so, yeah, I think the really smart people, though, that, like, don't know everything. They have a way of thinking and, like, a system for, like, how they would figure that out. And so I'm thinking like a grip of a great CEO that I worked with, like a Product genius. Like, he was not a finance genius, but he was able to figure out finance because he had some kind of core principles, which is like, oh, when you don't know a lot about an area, like find one or two mentors and expertise and like, you know, read these books and listen to these podcasts and focus your learning on this and kind of make decisions like this. And so he had like framework. So I don't think you can like completely wing it, but if this is not your thing, you can find ways to figure out how you're going to learn about that and have. Have ways of thinking, systems for thinking.

So I want to talk about Exit 5 and how you get there and have you tell us a little bit about that and then to your point of kind of like frameworks. And I think this goes to, you know, your most, I think your most recent book. Unless you're working on something I don't know about, but found a brand, right? Like you kind of put this framework in place of like looking at that and how somebody else can kind of create that model to kind of grow their business.

Right?

And so talk to me first about Exit 5 and then I'd like to kind of go to founder brand a bit. Little bit.

Okay, so Exit five. So basically about two years ago, I changed companies and when I changed companies, I was going from B2B SaaS to more E commerce type of SaaS. And I had just kind of spent seven years in B2B SaaS and I had started to build a following of people that were in that industry mainly through LinkedIn. And my LinkedIn content was like a. It was popular and, and got a lot of engagement in a way that I hadn't had any success with other platforms. Like, I'd been tweeting for 10 years and like my tweet responses were like, just from like you or something, right? Like, I don't mean that in like, it's like you get like one response or like, whereas like I would post something on LinkedIn and there's like hundreds of comments and I'm like, holy shit. Okay, so something is happening here. So I kind of just focus on LinkedIn and I realized like, oh, there's a. For some reason talking about marketing on LinkedIn gets a lot of engagement. It's really grown my content and not, not even just in a vanity way, but like the more people that followed my page and engage in my content, I actually could drive like real results for that. And so like, if we would do an event for drift Like a big ticket sales channel would be like me posting about it on LinkedIn or booking meetings for sales or driving people to content. And so like I didn't just see like the social vanity metrics of it. I saw like the impact of having an account with engaged followers, like could actually drive to something. And so I realized like, oh, I have something here. When I change companies, I was going to like launch a blog, like Dave's marketing blog or something because I was like, I still want to be like perceived as a thought leader. This is the industry that I want to keep talking about. I expect to have a career in here. It'd still be valuable for me to be known in this industry. So like, I want to keep writing about this stuff. My wife Leah, she happened to be listening to this, this comedian that she listens to on Patreon and it was, I had never heard of anybody on Patreon. And I'm like, what the hell is this? And she's like, Yeah, I spend $7 a month and I get like exclusive content and like she doesn't post this podcast anywhere else. And I was like, interesting. I'm going to try to like monetize this. Like I think there's an opportunity to do that. And so I want, I, I, and I didn't even have it like in a big fancy business sense way. I just, I'm into music, I'm into comedians and creators and I see people in all kind of walks of, of life in their craft, like starting to charge for content and it seems to be working well. I was like, I'm going to try this. And so when I left my job at Drift, it was like pretty buzz worthy within like the B2B SaaS niche. Like a lot of people are like associated me with Drift and like, oh shit, he left Drift, like what's going on? And so I took that as opportunity to launch. I knew I was going to launch this site and it was going to be a private podcast. So it's behind the paywall on Patreon. It's going to be a podcast and like just continuing to talk about marketing but just I figured people would pay for it, they could expense to their company, whatever. I recorded the podcast episode about why I left Drift and what I'm going to do next. And that was available in my Patreon only. And so I had a great hook to get people in there. I figured maybe 10 people will subscribe to this and it'd be nice like another, you know, 100, 200amonth. Chip into my rent a little bit and it's a fun little project. I'm going to do it anyway. And all of a sudden I had like 300 members and 500 members and then within two months I had a thousand members. And all of a sudden it's generating $10,000 a month from content. I was like, what the hell is that? Is. This is ridiculous. There's something like much bigger here and I like really committed to working on it. I'm like, I'm gonna post this thing all the time. I'm gonna really focus on the content here. Fast forward about a year into it. Right around the thousand member mark, I got a bunch of messages that were like, hey, there's lots of other marketers in here. Like we want to talk to each other. And I was like, oh yeah, this is not just about your marketing thoughts, buddy. This is like, there's a community here. People want to talk to each other. And so I added the community portion of it, which is a Facebook group. And initially it was called Dave Gerhardt Marketing Group because I suck at naming things. And it was like, so it was dgmg. And then like I'd go to meet with my accountant and be like, so how's DPLQ doing? And like it was actually like I was getting trolled by all these people. Yeah, I was like, this name sucked.

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And I also wanted to move it from like, I wanted to shift away from it being about me. I want it to be like I realized that there was a bigger trend which is like, oh, all these people are like, they're here because they work in marketing. They work in B2B marketing and SaaS marketing in some capacity. There's like wisdom of the crowds here. Maybe I'm the one who is helping to bring them here. But they're here because they want to like learn and connect with each other. So I want to like remove the Dave. I wanted to unbundle like the Dave from the branding. And so I came up with this story about Exit 5, which is a place in Vermont that my wife and I would go to on the weekends where her parents live and would just kind of like get out of the city. And I always felt like I would get unstuck on a work idea when we would go there. And I was like, cool, That's a cool name. The domain is available for $600. I bought it and rebranded it and called it Exit 5 because I as also for me personally, I don't forever want to be like Dave Gerhardt equals B2B marketing. This is something that I've done, and it's a part of my career, but I see myself as, like, doing other things and more than that. And so I think also rebranding and carving out Exit 5 is like, oh, now I can be Dave and one of the properties and one of the businesses or things that I do is exit 5. But it gives me, like, the room to do other things. And then maybe down the road, if there was a world where someone wanted to buy or partner with Exit 5, it's a little bit easier to do that as Exit 5 as opposed to, like, Dave Gerhardt Marketing Group.

Yeah. You know, so it's really interesting when I actually saw you post something about talking about the naming of the business, and I was like, oh, wow. I thought when you named it Exit 5, I was like, oh, okay. That makes a lot of sense to me. And I had, like, my own story again. I keep making up stories for you. Apparently, that's what I do. But for me, I was like, oh, yeah, Exit five. That makes a lot of sense because you're talking to a lot of founders within the tech industry, and oftentimes the goal is to exit nice within a period of time. And I was like, oh, Exit five. I'm like, that makes a lot of sense. So then when you said, no, it was the exit we got off in Vermont. I was like, oh, okay.

I was like, oh, all right. Well, there you go.

Yeah, Sorry. So blew it up. Blew it up. A couple things I want to touch on here that I hear you saying as we're talking about this that I think are kind of like the key things that I think people need to hear, particularly as you're a small business owner and those types of things, Right? Like, one of them, I think I hear you saying, is focus on your strengths, right? Like, you found a thing that was like, hey, I enjoy this format. This is the thing that I enjoy to do. So I'm going to really commit to doing that, right? Like, focus on that and let that be the thing that kind of drives you. Another thing that I heard you say was inspiration from other industries, which I think is one that's often missed. Like, you were watching musicians or you were watching things like applying these different types of strategies to what they were doing. And I often heard from the small business owners or marketers that I'm talking to is that, like, if you aren't very specific about what you're saying, they often miss tying it back to, like, the Example, like, or how to look at another industry and tie it back to what it is that they're doing. I was wondering if you could talk a little bit about that. Like, how do you find that inspiration from other areas, which I think sometimes just kind of gets us out of our own heads a little bit and allows us to open up a bit. But like, what's your point of view on that?

I don't know. It'd be. It's never been a thing that I've consciously had to like, turn on or off. I think. I didn't really study marketing in school. I got a marketing degree because quite frankly, like, I suck at math. I had no interest in finance. I could write and communicate and there was a. Like, you could get a marketing degree doing that. But I didn't, like, leave college being like, I can't wait to go get my job in marketing. I think looking back now, I've always been doing some form of like, writing and communicating as I can remember. Like, I gave the speech at my 8th grade graduation and I gave the speech at my high school graduation. Like, looking back now, I'm like, oh, there's definitely some. I didn't know. Like, no clue at the time. I wasn't like, yeah, I'm going to be a marketing, but there's definitely some connection in there somewhere. And so I've kind of just always been like, into just understanding people, kind of observing what gets a reaction out of people. You know, ranting to things about my wife. Like, did you notice that when this happens, all these this. I've just always been curious in that way. And at drift, I work for a founder CEO, David Cancel, who was like, very liberating and like, that's how he thought too. Was he. I saw him like, just focus on all the things around him in his personal life and he was like, don't study all that B2B. Like, don't. You know, he'd probably be like, against exit 5. He's like, don't join there. Like, don't listen to what everyone's talking about. Like, because that. That's where you can actually find all the advantages. And so he didn't want me to go to like B2B marketing school. He wanted me to go to, like, just understanding people school and like, looking around. And so I've always had a better. I think I'm good at content and good at social media as it relates to business because I am good at, like, getting feedback and understanding what people want and try to like, triangulate those things. And I'm, you know, much to, like, your skill set too, like taking ingredients and putting them together and be like, oh, if we were to write an article, here's what I think it could be. Like, I'm good at pitching the idea for the video, the idea for the ad, the thing for this and that. And so I think that's always been just a more natural thing. And so I think it's just been turned on in my brain. And I got to work for, like, David at Drift at a formative time where he was like, I remember specifically very, like, in my first two weeks in the job, he was like, I don't care if, you know, CAC to LTV ratio or SaaS metrics or this and that. He's like, you have something when it comes to, like, content and copywriting. Like, let's double down on that. Be curious, like, focus on what people are doing and, like, don't worry about, like, what the industry best practices are. And I think I've. The reason why I'm able to move really fast now is because, like, I, you know, he pushed me to do those things and to do fast in that environment. So now I've seen, like, oh, wow. If you. If I'm doing it just for myself and Exit 5, like, why can't I make this decision in this instant?

Yeah, I love that. You know, one of the things that I really love about what you're doing, and I kind of got started in this industry around 2006, is when I started kind of getting interested in it and kind of learning and doing a lot of the same things you're talking about. Like, at. For me, it was like, copy blogger was a big one, like, Brian Clark, like, those folks. And one of the things that I like that you're hot on, and I think this is important because it's. It is that understanding people piece that really drives everything that you do. Like, the technology is always going to change, and that's fine, but it's ultimately, it's about applying the technology to how you communicate. Like, oftentimes, like, I'll see, like, you post something and you're talking about a thing, and I'm like, oh, yeah. I'm like, that's like, not a new idea, right? It's something that's been around for ever, and it's just fundamental to who we are as people. And I think if you can spend more time understanding that, like, people always want to know, like, oh, when's the best time to do this? Or When's the. And it's like, it doesn't really matter if you're hitting the right things. Like, you want people to be like people looking forward to. Right, like, because they're connected to you and some human level. And I think that's really cool with what you do and you put into practice and just even talk about.

I also think it's tough to be an effective communicator. You can't just like, say it your way. You have to like, make sure the message has been received. And I think that's. I actually learned how to do that less as a marketing skill and more as like an internal career skill. Like, I just remember having to learning how to manage my, my managers and manage my boss. And in a way that was like, hey, here are the things that I'm working. Like, I, I've always been very like, proactive as like an employee. And it's like, okay, you're not giving me a plan. Like, I'm gonna come up with a plan. And I think that has also now kind of played out into how I've done marketing.

Has starting your own thing always been something you, you thought you wanted to do or how did that come along?

No, I would say the honest answer is no. I don't ever, I don't ever think I've thought about it. I'm not that person who is like, yeah, you know, I, I was, I'm a hustler. I, you know, I had a lemonade stand when I was in the fourth grade and that's how I knew I was going to be an entrepreneur. Like, I don't have any stories like that. I've always been like a little bit. Not as good as like at following directions and following the rules or like, or I get bored with like, really, if you tell me, like, hey, you have to do it this way and here's how it's going to do it. Like, my mind always kind of looks for like really there's not another way. And I, that's always kind of been baked into me and I've always learned best by doing things myself and so myself. So I've always had to like, have a lot of freedom in my jobs to be successful. But I didn't ever think about it because I never, I honestly never thought. I come from a great family. Like, we're def, we're middle class, like well off family. But I don't have any money. Like, I didn't have any other than what I've earned for my, like, I don't have any money that's coming from anybody. And so it was never real to me in that being in my 20s, like, I had no money. And so I was like, I can't go. Not like. And to do a startup, you always hear these stories like, oh, you gotta. You can't take a salary for X months, right? Or even if you raise money, you got to pay yourself some salary. And so I just was never like, well, that's not an option because I guess I could start a business, but it would have to, like, pay for itself. And so I had lots of ideas for, like, a business, but it was never anything that was going to ever get off the ground because I needed to make money. And I think what Happened was my DGMG Exit 5 started to become like, that income. And I was like, whoa, this is a business. And so I never, like, was like, I'm taking the big leap. Like, you know, when I left my job, I had a business that was generating more than my salary already. And so there was like, no, there was no risk in doing that. And so, no, I've never thought about it for that reason. And I think there's lots of stories I can tell myself now, like, revisionist history of like, oh, yeah, this makes perfect sense for things that have led me here. But no, I. I never set out to, like, be a business. I thought that I was going to. My hope was like, work at some tech startups. Like, I seem to be okay at like, doing marketing for B2B SAS and, and find my way around successful companies. My honest hope was like, maybe one or two will have an exit or have a sale and we'll make a little bit of money and then I can just kind of like, figure it out for there. And what ended up happening is that that did happen, but I also happened to build this other business on the side and. And that's kind of like, that's where I'm at now. But I don't have more stories of being an entrepreneur.

How does that accomplishment, though? Like, this is working, this is doing. How does that make you feel?

I don't know. I'm still, like, processing it every day. Like, I still wake up and I'm like, oh, you don't have to. I'm not going to work today. Like, I have my office in my house, but I'm not like. Like, I don't have this nagging feeling of like, someone's looking for me or like, this person needs me or I gotta do this. And so the I'm like, trying to be real with you. Like, I. It's so very unique and rare that this has happened. And I am still in, like, this weird point in my career where, like, I can't. Like, I have a hundred new ideas right now because I, like, haven't accept. Like, is this what I'm doing? It's crazy to me. So I don't know, Dave. It's my honest reaction to that that's.

Interesting, because I think. I don't want people to misconstrue.

Right.

When you say, like, oh, should I work today? Because the reality is, I mean, what you are doing and what you're doing in Exit 5 is a lot of work, and it's because you're creating. I mean, it's comfortable for you, but you are actually putting in a lot of effort. So I wanted to maybe move us there a bit.

Right.

Because, like, one. I guess the big question is, what is that process of coming from where you're working at a company where you probably have. Whether it's a small team, large team, whatever the case may be, you've got. You've got resources that. At least from a human level.

Right.

That maybe you don't have now. And so what is that transition like?

Well, first of all, because I. I do realize who we're talking to, like, not to take that advice is, like, I don't go into an office and do work. Like, back to the point we're talking about with content. Like, these are just notes and things that I've written down in the last hour. Yeah. And so, like, I'm not physically, like, going to work for someone else, but, like, in running Exit 5 allows me to, like, play to my strength and superpowers, like, in the ultimate degree. And so, like, it's a website, it's a podcast, it's social media. My brain is always going on like, oh, I should have this person on the podcast. Okay, I should have this person on the podcast. Let's get. Here's a good timestamp. Here's something I just said to Dave that would actually make a good. A good video for next week. I got to remember to write tomorrow's newsletter. And so, like, now we just have the freedom to, like, do those things all the time. And, like, I think of, like, I've now built a business around, like, a superpower of content creation, and therefore, it is easier, as opposed to, like, I'm not a great manager. I'm not great at finance. Like, I'm not, like, banging my head trying to do those things. So that was a good connection and observation. Sorry, what was your initial question?

The question is like, how do you get shit done? Basically right, I guess is what we're getting at is that, you know, you're moving from a place where you're not always doing the work like somebody else is doing that work. And now, I mean, do you have a team? Do you have people that you reach out to? I'm assuming you probably do, like freelancers and things like that. Like walk us through what that looks like.

I think I'm naturally like a competitive person and a goal oriented person. And so I think one of those things is driven by like, I have some rough goals that I have for exit 5. And so, and I'm not, this is not crazy. Like I don't have an operating plan for Exit 5. There's no spreadsheet business. And that's how some people are. Even if they came from that they might have the whole spreadsheet to run the Exit 5 business. I don't have that because I don't.

Need to do it.

I can see what I need to see. But I have basically two bullet points of a revenue goal and a content goal that I'm trying to get to. And guess what? Nothing happens if I make it or not. But I like to use those as a benchmark. And I found that as a person, I need those kind of regularly competitive things. I just got into running and my wife is like, you're 100% going to sign up for some type of race. And I'm like, no, no, this is just fun. Here I am, I'm now signing up. I signed up for Half marathon in April and that's just who I like. It helps me be productive when I.

Have those types of goals.

And so I think you have to be able to set goals if you're going to go and work for yourself. And so I have a clear business plan and goal for exit 5 in my mind. And the next thing that's really important is I think, just having regular routines and rhythms. And so, like, I am doing a lot with the Exit 5 podcast right now. And so I know that like from every, basically every Tuesday and Thursday from 1 to 3pm I'm going to be recording podcast interviews. And that's my time to do that. I know that, that every Wednesday I send out my newsletter. I know that every Friday I do this type of thing. And so like I can kind of use those as guardrails for like things I gotta build around. And so like yeah, tomorrow afternoon, like my wife and I want to go out to lunch or I want to go do something else in the afternoon. That's great. I know that in the morning I got to spend two hours and get my newsletter done. And I spend two hours, you know, sometimes two hours, sometimes it's 30 minutes. I got to get that out. And so I have like having those regular systems and check ins. If I didn't have any of those things, it'd be really tough. And now I have, I have three sponsors for Exit 5 for the year. And so like I have commitments that I have for them. And that means we got to do this this quarter and this, this quarter. So I think having the schedule and for me just being somebody that operates off my calendar is the other thing. So I think goals and deadlines for me is the thing that drive action.

Yeah, that makes a lot of sense. I think. You know, we were just having this discussion. I'm actually talking to somebody later in the week about like goal calling it goal getting.

Right.

But that idea is that like if you don't, I always look at it like if you don't have something leading you in a direction, I don't mean to sound woo woo, but like the rest of the universe doesn't know how to help kind of put you in the right path.

Right.

Like, and so you.

Right, you know, to your point about like how do you find inspiration and ideas like from outside sources? Well, if like that's the thing you're working on, it's like it just happens to find its way in there right now. And so like, yeah, you see it. And so like, oh, my goal right now is to grow members of Exit 5 from this. My brain is just going to be kind of like subconsciously working at that problem. And so I might all of a sudden sign up for something like golf community. And I'm like, man, that's genius how they do that. Oh, there's an idea that I can take. So I think, yeah, your brain, that is not too woo at all. I think that's so true about like having your brain turned onto that tuned.

Right.

You're just attuned in a different way.

Also just like on the goals thing, like I'm not a crazy goal. There are people who talk about goals and they have crazy processes for goal. Like this is my go goal is like a bullet note in my Apple notes that says like, because I should have a goal. And to me the goal, it doesn't always have to be like, I want to grow from 3,000 members to 5,000 members by this quarter. Like for much of last, for like six months out of the year. Last year my goal was transition DGMG to exit 5. And so what does that mean? That means I got to do the brand, I got to do the website, I got to relaunch the podcast, I got to find this. So there's like plenty of that that helps me figure out what I have to work on. It's not always like a numeric growth goal. When I talk about goals, it's like that's how I chunk up like what I'm working on this quarter or this month.

What would you say is your biggest kind of business related challenge or challenge slash? Maybe it is or maybe it isn't. But what, what's something that scares you?

I think one of the biggest challenges is probably is growth in that. There's a lot to unpack in that actually, because I think that, I actually think that there's a world where like exit 5 can be a 10 or 20 million dollars a year business. I've seen it like with other businesses like Content Marketing Institute, they're a little bit different, but there's lots of comparisons for this. And I go back and forth on it because I'm not sure that I want to do that. If I wanted to work a hundred hours a week right now on Exit 5, it could be a 10 to 20 million dollars a year business. No doubt that would require a, lots of hours of work that I don't want to sacrifice right now. B, it would require me hiring people and managing a team. Like there's a level of like, I could have gone all in and I could have, I could have a team of three to five people right now. Full salary, benefits, we'd have standups and one on ones and performance reviews. And there's a lot of things. So like I know for sure that I don't want to do that, but I also want to grow it a little bit. And so there's like the, like okay, well what should that be? And so it's like, well I could hire a freelance person and like have them grow my social media, but I'm not sure I want to like seed control to that and I want to train them on that. And so there's also some things where like I do like doing this and this is my little kind of project. And so I like, I like doing some of the things. And so I do. I read all the life hacker growth hacker articles about like automating everything and like, you know, I'm, I'm not a real boss because I should be outsourcing all this stuff to other people. But like, some of it gives me joy as like, I'm learning how to do these things and I'm tinkering with these things and it doesn't happen to take up 100 hours of my week. And, and I got to do something with my time. And so there's part of it that, that. So I think like one of the biggest challenges is just like growth. Like, I was just having a conversation this morning with my wife about like, hey. And I like bounce ideas off of her all the time for sanity because she knows that I'm very impulsive. And I'm like, I think I want to do this thing and hire somebody to do this thing for Exit 5. And she's like, well, but like, you change your mind a lot and like, you know, why don't you just try the experiment yourself and like, maybe do it for 30 days, do it for yourself and then if you want to hire them, you can do it. And so there's like little, just little decisions like that that add up. Like, there's lots of things I could do, but it's the like, decision factor of like, what do I want to do? What is worth my time? Should I do it myself? Should I hire somebody else to do it? I do have people that I work with. So I have somebody that I've met Chrissy, I met her through like an early DGMG member. Now they're married. And Chrissy's just like been in the Exit 5 community. She helps me with like, just kind of support stuff and she knows how all my systems work. And then I have people that I work with on a freelance basis, like I need video, I need a design thing, I need website. And I'm actually just working with an agency now that I pay them just like on a retainer to help with some marketing stuff. But I don't, I don't have any full time employees. So growth is the biggest challenge. Dave.

Gotcha. I want to shift this a little bit so we can talk about just, you know, from your, your expertise, particularly in the B2B space and marketing. Obviously we have tons of customers that are in that area, like, like, you know, and maybe this kicks us into some of this founder brand stuff, but I'll let you drive where this goes. But what are the things that you see from a marketing perspective, particularly in B2B, are the things that are, if I were to say to you all right, Dave, you're starting from square one today. Where would you start first?

The company story. Like positioning. Why does this company exist? How are we different and unique and or better, who do we serve and why? Like really nailing that true differentiated positioning just solves like. So I mean, you know, this like solves so many of the minute growth hacking challenges. And that's where I would spend most of my time. And I also say that answer because there's lots of other implications there, like the product that you're building and the customer that you're serving. Like, you can't do great marketing without strong connection to that.

You know, I just want to stay on that for a second because, like, I think this is one of the things that, you know, I'm always like, you know, the way you, it comes down to like the way you say something based on who it is that you're trying to reach, right? Because like, I would say, like, if you were going to explain quantum physics to your wife, your grandmother or a five year old, although it's the same thing, because of the people, you know, who you're talking to, the way you're going to do that is a lot different, right? And I think it's the same with the business. If you know who it is you're serving and what you're trying to do, the conversation becomes uniquely attuned to those people.

Right?

And I think that's really important that I think a lot of times, particularly businesses starting out, they don't want to, or they feel like they're getting too narrow or pigeonholing themselves like, oh, we're for everybody. But like, really you can't be, because if you're for everybody, you're for nobody, right? Like, and so it's an interesting thing there.

I also think it's much easier to like, build and be everything for everyone later if you first have that, that wedge and that niche and you can like, you can add more things on like, the great coffee shop is gonna also be successful if like, after people come there and they love the coffee, you add a breakfast sandwich and you're like, yeah, that place I go to, they have breakfast sandwiches now, you know, then the customer's not like, well, how, how do I brand them in my head? You know, like, are they coffee or are they sandwiches? It's like they're. And I think you can do the same thing in, in B2B and whatever you're selling to, whether you're a small business, a tech company, whatever, being specific and Carving out that niche and having that clear strategy has everything to do with how successful you'll be with marketing.

So, well, let's go there, right? You've got the story, you've got the positioning marketing. Where do you go from there?

Well, I think one of the big pieces of that is instead of even thinking of it as marketing, it's like, okay, now we have this story. Where are our customers hanging out and how do we tell this story to them in a way on these channels? And I'm always a believer in, you can call it content, you can call it inbound marketing, you can call it whatever it is. I've always, my bias is towards wanting to build an audience and build owned traffic to my own thing. And so I realized that there's a lot you need to be doing with advertising and paid media when it comes to E commerce and direct to consumer brands. But ultimately, I think always the marketing advantage is like, I think content is the greatest marketing channel. And so I come back to like, okay, well this is our story. How are we going to tell this story? Does that mean, and that can mean everything from like, what's the content of your website? To thinking about how do we get people to our website? I mean, I think today, brick and mortar business or online business, like, the website is going to be the most visited thing. Even if someone's going to come to you in person, they're going to check your website for, you know, hours and, and location and menu and all that stuff. So it starts with like, what's the content in your storefront, which is your website? And so how do you articulate that story? You can have a great strategy on paper, but if you can't articulate it into a compelling website that attracts readers and converts readers, it's going to be a tough challenge. And then I think I'd think a lot about the social media channels that we are. Like, look to yourself and most importantly, like, have a deep understanding of that customer and where is your customer spending a lot of time? They're in these subreddits on Reddit or they're not on Reddit at all. They're following these people on TikTok or they have no interest in TikTok. They only find out about information from each other at these local events and we got to be at these local events. Great. So like, you can't be everything to everyone from a story standpoint and you also can't do everything from a marketing standpoint. And so I think like, if I'm trying To think about how to get marketing started. I'm looking for one or two channels that are going to help us bring eyeballs back to our, our website. And. Or maybe there's a path where the website is still important, but it's not about traffic. It's about like, you know that quarterly meetup example I use?

Yeah. You know, it's interesting now particularly how when you think about a lot of social channels have changed.

Right.

It's a lot different from back in the day when it was like you could post something, you post the link up and people come to your website, the channels. Now obviously there's algorithms, there are things and there are also they want the engagement on site and so a lot of the content has to be there.

Right.

And so how do you think through that?

It's tough to be successful on a channel without having a deep understanding of the channel. And so I think what you can't do is you can't have one idea for content. Like we come up with a campaign like we're going to do this month. The big thing that we're trying to promote is X and we come up with an idea for that campaign. Right. We can't just like make a video or make some content and then like post it on Instagram and post it on YouTube and post it on LinkedIn and send an email about it and like, expect that things are going to work. Each one of those platforms need to be uniquely considered. And so like the LinkedIn content is going to be different than the TikTok content, is going to be different than the Instagram content. And I think the people that do those things. Well, you see this all the time with like TikTok creators. It's like they're kind of, or Instagram reels, like they're kind of on one platform or the other. And the reason that the content is working is because they're creating unique content for that platform. They use that to figure out that it's successful. And then they might start posting the same stuff to like YouTube shorts and the same stuff to Twitter. You're focusing on one or two channels and I think you have to really commit to like creating original content for that channel. We're just in a different era than like, if this was 2010, 2011, 2012. I would say probably the answer is like just being on those channels, like, if you were on Twitter, like you could get more customers maybe than somebody else who wasn't. I think now it's gotta be much more about like, what is our Interesting. Like, what is our content angle? Is it educational? Is it witty? Is it funny? Is it serious? Is it. You know, what is it? What's the message? And then I would think hard about, like, one or two channels where you're. You're making bets. I mean, and I think everybody has examples of these things now in our. In our personal lives of, like, somebody that you follow on some channel and you ended up buying a thing from them. And I think that, to me, is, like, the best approach to thinking about marketing for your business. Like, how am I. I sell this widget.

Right.

How can I be a great resource for things that the people who would buy this widget would be interested in online? Get them to follow me, get on my email list or something, and then I'll have a much easier time selling them that thing down the road.

Yeah, love that. Listen, we're coming up to end of our time here, so I want to ask you one last question. Which is what's the best piece of marketing advice you've ever received or that you could offer someone?

Ooh, that's a good one. I don't have, like, one definitive answer, but I just think of, like, the first quote that I thought that came into my head. And sometimes I tell this to people and they don't understand it, and so it might not be the best quote in the world, but it's from Roy Williams, the wiz. The. He write, the wizard of ads. He's a great.

Yep.

He says that the risk of insult is the price of clarity.

Unpack that for me a little bit. What does that mean to you?

It means exactly what we were talking about earlier, which is like, being specific to a core audience. So the risk of insult is the price of clarity. Oh, what the heck? You don't have this type of pizza here. What the heck? I'm pissed off now. I thought. I'm sorry, man. We only sell this.

This.

The advantage that you create from being so specific.

Right.

And so. And I think that advice can be applied from, like, a customer targeting thing all the way down to, like, a website headline. Like, the amount of times in my career I've, like, gotten in an argument with, like, the head of sales or head of whoever about, like, well, this headline doesn't speak to this audience. I'm like, the risk of insult is the price of clarity. It might not, but for, like, 80%, we're trying to appeal to this. Like. Like, this is the one person. So I think just the more specific you can be, the more clear you can Be the risk of insult is the price of clarity.

Love it. I'm going to end there. Dg, thanks so much man. Appreciate your time.

Yeah, thank you, Dave. I appreciate you having me. Hey, thanks for listening to this episode of the Exit 5 podcast. If you're in B2B marketing and you want to grow your career, you should also go and check out everything that we have have over@exit5.com we've got articles, we've got videos, we've got templates. Plus we have a community. A community of over 4000 B2B marketing pros. Whether you're deep in your career and want to connect with your peers or just starting up and you want a place to go where you can see what people are talking about, get smarter about B2B marketing in your own time to grow your career and help grow your company. Go and check it out. It's exit5.com you can get on the email list there. You can can join the community. There's 4,000 marketers in the community. We have a job board. We're always adding new stuff. It's really becoming the number one place you can go if you want to grow your career and learn more about B2B marketing outside of what you're doing inside of your company every day. So check it out. Exit5.com and I also want to make sure I give a shout out to my friends at Hatch. That's Hatch fm. They produce this podcast. It sounds amazing because of the work that they do and they work with B2B companies just like yours. They offer unlimited podcast editing and strategy for businesses. You can get unlimited podcast editing and on demand strategy for a low monthly cost. All you gotta do is just upload your episode and they take care of the rest. Go and check them out. It's Hatch fm.

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