Why Am I Not Generating Quality Leads? Payroll Company Sales Tactics That Work With Chris Clark

Chris Clark breaks down lead generation into four quadrants: cold vs. warm and one-to-one vs. one-to-many. He recommends Guru's free HR templates as a lead magnet, cold email with proper domain warm-up, LinkedIn outreach for higher response rates, and personal brand engagement over corporate posting.
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If you don't have a repeatable way to generate leads, I got bad news for you. You don't have a business, you've got a hobby, and a pretty crappy one at that. So today we're going to talk through what are the 4 ways where you can generate leads, how are companies generating more leads in 2025, and some of the strategies that we're using at Guru and Underdog Digital to help not only ourselves but our customers to generate more leads. Welcome to Payrollin', the show where you will learn how to operate and grow your payroll business from the most dynamic minds in the business. If your company offers payroll services, this is the podcast for you. And now, here's your host, Matt Vadie. Let's go! I'm joined here by Chris Clark from Underdog Digital. Chris is a digital media manager. What is your title at Underdog Digital? Marketing coach. Marketing coach. All right, cool, cool. He's also a radio personality, among other things, works at Gamecock Central. He's on 107.5 The Game here in Columbia. If you're local to us, fantastic marketing resource. Thank you for joining me today, Chris. But first, let's go ahead and dive in and talk about what are the different ways we can generate leads, right? So we've got 4 quadrants. I really like this. You and I are reading the book. Have you finished $100 Million Leads yet or you just started? Is this the first time you will have read it is when we're doing it as a book club?
I'm on my second, actually pre-book club. I'm on my second audio. Uh, while I walk around, I like to listen to the book. So this will probably be my third go-round on it actually.
Awesome. Awesome. I love it. In the book, it's a fantastic book if you haven't read it. I think I recently recommended it in a podcast episode, but he talks about the 4 ways that you can generate leads as a business. And there's only, I love the way he puts this because it's just so simple. You can see the quadrants. There's people who know you. People who don't know you. So cold audience and a warm audience. There's one-to-one and one-to-many. So one-to-one cold, one-to-one warm, one-to-many cold, one-to-many warm. So we're going to talk about some of the different ways that we're leveraging each of those different quadrants and different things, what's working, what's not working, and how we adapt and adjust based on what's working there. But first, I mean, what are some of the things you've seen that are working for payroll companies right now?
Well, I think, um, a few different buckets there. I mean, one that I love that Guru does a great job of is you hit their website and you get 42 HR templates, right? And I absolutely love this one because a lot of people think, hey, I'm starting a business, I have a business, I need a website. And you're right, you do need a website for many reasons, but a lot of people get hung up on the design or maybe even how much traffic they're getting. Obviously traffic's an important metric if you're talking about a website, but what are you doing with the space and the real estate, so to speak, on your website, right? So a lot A lot of people love to, when they're designing a website, let me put an email box that says subscribe. To what? You know, what are you asking me to subscribe to? It sounds like a chore. What am I getting in return? And often people say something like, get the latest, keep up, find out more, which is a little bit better than those others, but still not great. Now, when you go to Guru's website, what are you going to get? 42 free HR templates, right? Guru gets an email in exchange, and then they get obviously tremendous value by getting 42 free HR templates. So I absolutely love that example. Another thing I think you see in that is people sometimes are afraid to quote unquote give away some secret, right? But we found a lot of value in Guru doing this because it leads to higher conversions when somebody does hit their website. You can obviously use those assets like free HR templates even in other avenues of marketing like cold outreach, where as opposed to asking somebody if they're interested in something, you can present them that some— with something that's immediately valuable to them in exchange for their email or a call or something of that nature. So absolutely love templates and, or, and, or just, Matt, doing something that's different than, hey, give me your email for no reason at all.
It's interesting because the 42 free HR templates we can use at every stage of the funnel. So that's the thing I like about it the most, is this cold traffic shows up at the website, boom, they can now get into and become a warmer lead by taking advantage of getting a great resource. Like, I mean, this is literally when I remember sitting down and creating the 42 Free HR Templates. It was like, what are the things that every client asks us for in the first 90 days? And let's just put it all together. So, you know, it's a performance management, it's a, it's a new hire packet, it's a termination checklist. It's all the stuff that every business needs for their HR that we just went ahead and put into one thing and said, hey, let's give it away. And it was based on this philosophy. So, so this is funny because I, I actually had to look this up this weekend. We're just coming off of Mother's Day when we're recording this right now, and my wife loves coconut cake. And so this restaurant in Charleston, the Peninsula Grill. I don't know if you've ever heard of it. It's right there on the corner of Market Street down in Charleston. If you're ever in the area, go check it out. For the record, if you buy one of their coconut cakes delivered to you in the mail, like a dry frozen or however they do it, how much do you think this coconut cake costs? You gotta bro me and you gotta, you gotta guess low because I'm gonna go high. So make sure you guess like— this is a good tip to everybody listening at home. Hold on, I'm turning the camera to me here. When one of your friends asks you to guess a number, like if you know that they're, they're gonna go high, you gotta go low. You gotta be a bro. Like, so if you say $500 right now, like you're really 'Cause then I'm gonna come in and be like, it's $270, Chris. Like, thanks a lot for blowing up my number. Like, no, no, it's not $500. What are you, ridiculous, man? Of course it's not $500. All right, so you didn't get to guess. That's me talking over you as usual. But just, just be a mensch, you know, like help your homies out. Don't guess high. All right. So it does cost $270, Chris. Great guess. I'm on one right now, as they say. I haven't even had a C4 this afternoon. But so what they did though, Peninsula Grill in Charleston was about, it was 10 years ago, 2015. They published the recipe of this famous coconut cake that costs $270 to have delivered to your home. And you know, it's $20 a slice if you go there and you buy it at the restaurant. And you know what, why on earth would you publish your award-winning recipe, right? Like, why would you do that? Well, I know if I publish this recipe— well, guess what I didn't do? We had, we made Mama a coconut cake on Sunday for, for Mother's Day. Well, guess what recipe we didn't make? Peninsula Grill. Because it's a nightmare, dude. It's like, I mean, it was, it would have taken us 6 hours to make this cake, and there were ingredients I've never even heard of in this thing. And so I'm looking at it, I'm like, me and 13-year-old daughter are getting ready to make this cake. There's no way we're going to be able to do this. And I have tried in the past and guess what? It didn't come out as good as how they make it. It took me 4 hours. I had to go buy all these ingredients, took me a ton more time. By the time I tallied up all the time, money, energy, well, $270 seemed like a heck of a deal, right? And so in content, in our world, what we want to be doing is giving away the recipe. We want to make sure that we're giving away whatever it is that our customers are coming looking for. Again, what templates do my customers come looking for in the first 90 days? Here's all of them. Let's rock and roll. So I love that. Where does that fit, right? Let's think about that. So if that's— if I go to the Guru website, I get a free resource, free download. And just for like people's knowledge out there, we probably get 60 leads a month just from that form on the 42 Free HR Templates landing page. So it's a good lead magnet for us. Where do you think that fits in terms of the quadrants? One-to-many, one-to-one, cold, warm?
You know, it's, it's one-to-many, I think, because it's coming off of your website, which obviously is not, you know, an outreach unless it's somebody finds out about your website from a one-to-one cold email communication. That's very possible, obviously. Or if you're just saying, hey, do you mind if I send you these HR templates instead of, hey, can I run payroll for you, right? As a service, that's this different ask and a honestly a better ask. So I would say one-to-many would probably be where that fits in. It can be warm or cold-ish, but generally I think it's going to be more in warm because chances are somebody's found your website, it's from Google or You know, it's probably from Google, honestly, searching for pay— payroll company near me or best payroll companies or whatever it may be.
Yeah. And you're right. And we'll stuff it in a bunch of different places. So we'll do one-to-one cold, we'll run ads to it. So it's got a landing page, we'll run ads to it and we'll get some good leads from that. We'll do one-to-one warm like I talked about it. We'll use it as part of the nurture sequence once we have somebody in sales process of, oh, hey, here's a small example. And now just imagine us making the cake for you on the other side, right? So we can use it at each stage of the funnel. It could be middle of funnel content, bottom of funnel content, but it's— it's definitely usually a one-to-many play in that it's either— so, or somebody's going to find it organically cold, or somebody's going to find it warm, and that we're going to kind of push it to them. Good stuff there. So that's a good play. What else do you see in that's working well in the payroll space right now?
Well, I think— so let's talk about cold email. It can still work. You know, I've tried to talk to a lot of people who are— and learn from people who are really, really good at email marketing. And the funny thing about it is you're not going to get the same answer even from people who are really good at it, right? Some people send from one domain Send from 50 domains, send this amount of emails per day, send way more than that, use one sentence emails, make very, very long emails, right? You will get those answers and everything in between and you'll get them from people who've had success, right? So the point is, you know, yes, you have to have strategy, but don't get so bogged down in that that you never start, right? We know email marketing— we're in 2025. It's a lot harder than it was 10 years ago, 5 years ago, 2 years ago. We've seen it get way more difficult. A lot of the changes to email service providers, spam filters, quite frankly, make it more difficult. So the main thing that you need to do when you're thinking about cold outreach, you can think about different types. There's just, you know, there's cold outreach where you're sending HR templates. There's cold outreach where you're, you know, finding somebody on a list and you're reaching out to them and just straight up asking, hey, are you in need of this? That goes back to kind of the one sentence emails. You see a lot of those things. The biggest problem that people have that I see is that they're not hitting the inbox. That's the number one thing you need to be thinking about instead of, should I do a newsletter? What should my copy look like? Those things are important. Think first though, are you getting in the inbox? And so there's a lot of, and that's a great example, right? For us at Underdog, a lot of clients who are thinking about cold email, a resource we could create is here's how to get your emails in somebody's inbox. They may then look at that and say, awesome, that's a great resource. It's helpful. I'm gonna use it. They may also say, I don't understand this and it's too much work. Can you do it for me? Right. So it's a great actually lead magnet for us. But cold emails still can work. Two keys. Get it. Three keys. Get in the inbox, add some type of value right there. And you've got to be able to achieve scale. You can't send 100 emails in 2025 and say, where are my 20 leads? It's just not going to work.
Well, not unless they're highly customized, right? So if I'm sitting down each day and I'm just like researching, but again, it's, it's, it's the ROI on the time. Time there. Now, I, I could argue either way. If I sit down and write 5 highly targeted emails to 5 people every day that I know are fitting a little bit more in that one-to-one warm category, because that's where— that's the only way that's going to work, is they've got to be one-to-one warm. If it's one-to-one cold, 5 a day ain't gonna cut it. Like, that's just not going to be enough. And so, to your point, I think a lot of people don't understand the complexity of cold email in terms of— I know for each of our companies, you know, we've We've got up to 5 domains we're sending emails from. We've got, you know, like to your point, we just had to go through an extensive warm-up process. So Outsource Scale, we recently talked about on one of these podcasts, a new business. We accidentally sent a blast to like 10,000 people before we warmed up the domain and immediately started landing in spam folders. And we're kind of laughing to ourselves like, of all people, we should know better, right? And we still went ahead and made that mistake anyway. And, you know, look, if you're just going to send 25 cold emails a day and you want to send them from your primary domain and they're going to be a little bit more nurtured, great. I would say with tools like Clay and what you have out there today to be doing that. It's just, you know, as much as people hate Clay and AI email and, you know, just sort of what it is and what it stands for, you're kind of wasting your time trying to sit around and send 25 batch emails out of your inbox directly and not using the tools available to you. Things like Apollo, Clay, and what's the one you love? You love SalesHandy.
SalesHandy is a good one too.
Yeah, absolutely. Tons of good tools out there for cold email. And I hate to break this to you, those of you that hate getting your inbox filled with cold email, because your inbox is filled with them because it works. I mean, it stinks. Anybody wants to say that, but we have another cold outreach tool that works way better. I know this as a customer of Underdog Digital because it's crushing for us right now at Guru. And what's the cold outreach that is crushing most for payroll companies right now?
Yeah, LinkedIn is fantastic. I mean, it's the biggest and best, you know, B2B platform out there. You know, LinkedIn lets you get, if you want to, more granular with what you're doing because, you know, and you just kind of think about from a common sense perspective, put yourself in the shoes of somebody that you're reaching out to. Let's say somebody completely cold. If you get— if I got a cold email from Matt Beatty, it could be literally the exact same message. If I don't know you, you know, maybe, maybe you've included some type of resource in your email. Maybe you've given me a website. I've got to go click the link. I've got to go do some research. Maybe you have your picture, maybe you don't. As opposed to LinkedIn, right? I go to LinkedIn. I get cold outreach from you. Now you've got basically kind of a, your, your persona. You've got a bio. I can go to your page very easily in one click. I can check out, does he look put together? What, what does his bio say? Where has he worked? What does he do? Who does he serve? I can look, do you have posts? Do you post regularly? Who are your connections? Do we have anybody in common? Right? So LinkedIn gives you more answers immediately to where it kind of just lowers the tension, I think, on LinkedIn. And so you typically see better response rates from LinkedIn. Something that we're doing a lot right now— experimenting isn't the right word, I don't think, because there's actually a lot of data that shows this works better. But we're starting to combine email outreach with LinkedIn sequences all in one, right? Because some things— sometimes you may get, hey, here's a list, let me send cold outreach. Here's maybe that same list or a similar one where there's some overlap. Let me send LinkedIn campaigns where I'm connecting and I'm automating messages to those people. And it can, it can get confusing if you don't do it the right way. So if you build in sequences where you're hitting those steps, it becomes more powerful, you know, over a short period of time.
Are you doing those in Apollo or where are you doing the ones that include the multi-omni-channel approach?
Apollo is an option for it. You can also do it in SalesHandy, which is one thing we do. One thing to keep in mind is, and I actually do them in SalesHandy. So Apollo, I couldn't speak as much to how you do them in there, but you are creating a little more manual work. Look when you do them in Sales Handy. For instance, let me give you just a, you know, a layout. Typically you're going to have what, 3 to 5 emails in a sequence. Let's say day 1 is an email. Day 3 is a LinkedIn connection. Day 5 or 6 is an email. Day 7 is a LinkedIn actual message. You're not going to be able to automate the connection. You're not going to be able to automate the message. That can be okay though. It gives you a way to pretty quickly do it, go through, mark it as complete. It moves you to the next task in the stage. And by that time, if you've gotten through all the stages and let's say your LinkedIn LinkedIn messages last, you're going to have some data on that person. Have they opened any emails? Have they interacted? If they've replied, we might have already moved to another stage where I don't need a LinkedIn DM anymore. And so you've got some data where you can now go back and kind of customize your message at the end. You see customization work great. You see cold outreach on DM work great where it's literally completely automated and where you're connecting and sending out campaigns kind of like cold email on LinkedIn. So there's not a silver bullet answer, but you should be using LinkedIn. If you're not, you're missing out. Yeah.
And I think when you about this in terms of lead gen, right? So this goes back to, back to when I'm a sales rep carrying a bag at a Fortune 500 company. Every single month we would have somebody from the sales team create a campaign. It would be omnichannel like you're describing. It would be multiple steps. This stage of the game, this part of the game has not changed. Like we have to be creating omnichannel multi-step campaigns when you're doing cold outreach. Phone's not enough, email's not enough, LinkedIn DM's not enough. Like we've got to hit them multiple places to make sure that they know who we are. And I know that some of you, again, it's like, it's It's very easy to get lost in this world of like, boy, I sure hate it when that happens to me. Well, again, I got bad news for you. It happens because it works, man. Like, it works. And so, you know, we just saw it happen this week. I just, I see these people come in after that third, fourth, fifth touch, right? Where it's like, you know, if I was doing that manually, I would have given up by now. And that's how we used to have to do it, right? It was like, you know, you could maybe send the mass email, but then we always have a phone call component of it, which is obviously manual, right? And I mean, now don't get me wrong, in our CRM, we have the AI voice thing, which I am very hesitant to play with. And Underdog provides us with this awesome CRM with a bunch of preloaded templates and tools. You know, that little AI bot has been tempting me down there, but I have not turned on the voice yet. So if you start getting cold calls from me that don't sound anything like me, you'll know that I finally fell to the AI bot. But so, all right, so that one's good. So we've got one-to-one outreach cold, but it's scale. So that's kind of the cool thing about that, right? So it fits into that quadrant of one-to-one to cold, but we're doing it at scale. So I love that with, you know, cold email, cold LinkedIn reach, again, like the thing nobody wants to hear because all of our LinkedIn inboxes are filled with junk is that like you're probably going to keep getting more for the foreseeable future. And like I tell people all the time, like especially if you're on the free plan on LinkedIn, you should know that if you're not paying for something, you are the product, man. Like, I mean, you are the product. So it's a very simple equation. It's Facebook 101 right now. One of the hardest ones for us over the years, and we still have not cracked the code on this. So I'll be interested to hear, you know, I know for a lot of our payroll companies, we've done well well with this, with things like what we described, running paid ads to a landing page for a resource that you can download, and then we're going to get leads. They're not the warmest leads, right? They tend to be mixed quality. But, you know, for a couple hundred bucks a month, you can get 30, 40 leads just from that. And so if you've got sales reps that are looking for things to call on, I think it's a pretty good investment of time and energy. But if you're looking for more direct response, paid ads can be a little more challenging, particularly in the space. And I think the thing that people don't realize is, so if I'm, I'm a B2B company and I'm running paid ads, you're almost never going to see paid ads for a product that costs $5,000 a year plus that just says buy now, right? I mean, and it's not going to be book an appointment now either, typically. And on top of that, if it is, you have to get comfortable with what you're willing to spend to get an appointment. What is it really worth to you to have a first appointment with a potential client depending on the size of your, your annual value of a deal, which is the part— so we're in the quadrant now, one-to-many cold. And so paid ads is really your, your kind of biggest thing here in terms of how do I get in front of as many people as possible, as cheaply as possible. Paid ads are the way to go. But in our industry, in the payroll industry, it's definitely been a hard one over the years for people to— if you go right now and you can pull— one of the cool things is Facebook ad library. You can go in there, you can pull any ad running for any company that they currently have active. And I don't know, I've mixed success with whether or not I could pull up archived ads sometimes. I don't know if that's just me and if I forget how to do it or what. But Gusto is a good example. Gusto right now, if you go to their paid ads, this tells you everything you need to know. Every paid ad they are running, well, as of last month, month was for their partner accountant program. Not a single paid ad was focused on direct-to-market like hire our payroll. It was, hey, Mr. Accountant, Mrs. Accountant, get certified on our platform and you resell it. So they're running paid ads to their partners, not to their end users, which is an interesting strategy. And a lot of people here listening can learn from is how do I try to nurture that 1 1 11 group who can help me to sell my products? But for us, we are working on some more direct response stuff on the paid ad side right now, but we're getting highly, highly targeted. You know, I just interviewed Matt Umholtz on the podcast, and, you know, we talked about— this is the first time I've ever maybe held anything back on this podcast. I've shared more on here than I even care to admit, but I was like, this niche that we're targeting right now, paid ads, I'm not going to share because it's a sub-niche to the point where it's kind of like one of those, huh, if that works, that's a really, really targeted industry. And I don't want everybody listening to this podcast to start running paid ads to the same target audience I am. So we're going to keep that one under wraps. But I'm sure if you do some sleuthing, you can figure it out. But so talk to me about paid ad strategy. Where are you seeing it work? Where are you seeing it fail? And what are some opportunities you think in this space for paid ads? I talk to founders in the payroll, HR, and accounting industry every single day, and they all tell me they need more of one thing. It's not more money. Money. It's not more AI tools. It's more time. How do I get more time? Well, I hired a virtual assistant through OutsourceScale.com that helps me manage my inbox, manage my calendar, handles administrative tasks for me, helps support my marketing efforts, and much, much more. The cool thing about OutsourceScale is that they actually train the virtual assistants on the latest and greatest AI tools to make sure that they can't only do that administrative work for you that you need to get off your plate, but they're doing it in the most efficient and effective ways possible. I've been so happy with my assistant from Outsource Scale that I've actually added multiple other teammates to our other companies through them. Their pricing starts at only $7.99 a month, and they make it super easy to get a new teammate onboarded and part of your team very quickly. Check them out today at outsourcesscale.com.
Well, you earlier, you brought up Alex Hormozi, and I don't think anybody's as good as he has been at paid ads. He's had massive success with it. And so a lot of what we've learned and implemented, you know, whether by design or just because it's smart and sometimes just common sense, frankly, works in this space. So the biggest thing I think with paid ads is a lot of people say, and I've had people call me recently about this, I want to run some paid ads. And my first question is, why, you know, you want to make sure again, when you have a business and you start thinking about lead gen, if you're having problems with it, well, what's, you know, oh, I need a website, right? Or I need to make my website better. Okay, what does that mean? Same thing with paid ads. If you, you can waste gobs of money with paid ads, and you probably have some examples of that, I would imagine, from the past. You can also do incredibly well with ads. And so I would say the biggest thing with ads, yes, there's strategy in terms of which audiences are you hitting. The Gusto example you gave, the unnamed example that you just gave, you know, maybe we can come back on here and talk about how successful or not that was, and hopefully it's very successful. But I think a lot of people run ads, even maybe run them to the right audience, but then there are other problems. And typically what you see is bad copy, uh, bad call to action, pointing them towards an expensive product right off the bat, to your point. So people are seeing it, but they're not stopping, they're not clicking on it, you know. And I've seen several examples of this in the past Hey, you know, another example— hey, video, I'm gonna run video ads. Cool, that can be great. It can also waste you a lot of money. Is your video more compelling than a graphic with great copy? And it can literally be the exact same thing. Karen and I from Underdog were talking about this recently. We were going back and forth between an ad that we had seen, and I sent her something and said, which one of these would you click on? And we agreed on it, it was the traffic, which was probably much cheaper to produce than a video, right? So I think that's the biggest thing. Yeah, you're gonna— you gotta know— you've either got to know or have somebody who can set it up for you, everything that's involved in that, finding your target audience, but nailing your— what people see, making them stop the scroll, adding value, making them interested so they're clicking on it. And then the other side is you got to have great landing page copy, great value, um, all those things important.
Well, it is funny because I click on all the Facebook ads. I am like, if they're relevant to me, I click on them, even if they're not relevant, because it's getting served to me for a reason. It has an incredible algorithm. And now look, let's, let's look at ads in some different ways here too. So you've got your Facebook ads, which might be a little more— so like I said, we've probably the most success we've had on Facebook at Guru has been to the 42 Free HR Templates because it is a good way to stir up cheap leads. But again, the quality Quality, eh, kind of mixed. At Underdog, we're serving a whole bunch of people with a whole bunch of different types of paid ads, and we've had more success with some of those other industries than ours running search ads, right? So a search ad would be Bing or Google where, hey, every time somebody's searching for the term "PEO South Carolina," I show up as the sponsored ad at the top of the page instead of a cold ad, which is just going to run in the feed and, you know, maybe pick up on. Now, here's the thing you have to remember too, man. Facebook is crazy for this because we started Outsource Scale. So it's a virtual assistant staffing agency.
We're finding Filipino virtual assistants.
That are getting trained on AI for companies here in the US. But so as soon as I started checking out some of my competitors' ads, I clicked on maybe 2 of those ads and then I started getting served every other competitor in the virtual assistant space, their ads. So basically, if you're a payroll company and this is happening to me right now because I'm doing research on the payroll companies' ads, I have— I'm getting 5 payroll companies' ads per day. So that means you're paying for another company to also get put in front of of me at the end of the day, right? So like now Facebook says, cool, you're interested in payroll services. Well, let me throw these other 5 payroll companies in front of you too, which I think is crap because I'm like, man, I just wasted all this money on an ad and then you served them up every one of my competitors at the same time, dude. So that, that bothers me as a consumer, but as a researcher, it's actually super helpful. And I got to tell you, some of y'all listen to this, I'm seeing your payroll Facebook ads and they're awful. Just terrible. It's like, do you want a better payroll service? Do you want to save hundreds of hours a year, man? Like, who is doing payroll now that's going to save hundreds of hours a year by switching to you to use a— like, everybody uses a payroll system, dude. QuickBooks does it just as efficiently as our system. There's other value to what you sell. Nobody's saving 100 hours a year with 10 employees switching to your payroll, bro. Um, so, so that piece is important. But let's go back. One, one thing I want to touch on there with ads, though, because people will often get hung up on how expensive ads are. And one place where we hear where they're very expensive is LinkedIn, right? So LinkedIn ads are kind of known for being expensive. But until you've sat down and done the math, what you can afford to pay to acquire a new customer, you really don't know what expensive means yet. So for example, if you told me— if I came to your office right now and said, hey, I'll sell you appointments, you make appointments for $200 apiece, you'd probably look at me and be like, dude, I'm not going to pay you $200 to set an appointment for me. Like, that's crazy. That's so much money. Whereas if you sat down and did the math and said, all right, what's the average lifetime value of my customer? So, you know, they're with us 7 years, they spend $20,000 a year with us. It's $140,000. How many meetings do I have to have to close a new deal? Well, for every 5 meetings I have, I close a new deal. So for every $1,000, I close a new deal. So I can spend $1,000 and get $140,000 in lifetime value. That's an astronomical, off-the-charts low cost of customer acquisition. And obviously you're going to have other things that are going to play into that cost of customer acquisition beyond just the ad spend, you know, the sales rep salary or any other marketing you're doing around that. But you've got to know those numbers before you go ahead and start running ads, because that to me, you know, whenever I'm over there helping out with Underdog is, is like, you know, to your point, we want to run some ads. Well, do you know exactly the offer to exactly the audience and what you are willing to pay to acquire those customers? If you don't know those things, go back to square one.
Yes. Yeah. I mean, and ads are— yes, they're an expense. But, you know, if you think about, okay, I'm going to spend— let's just use a round number, you know, if you're spending $50K on ads versus, okay, I'm going to hire a sales rep for $50K, you know, which one is going to produce more for you? If you're $50K employee, is producing for you, that's a great investment. It's a cost. But a lot of people— I think you're right— a lot of people look at ads as ads are expensive. Well, employees are expensive, you know, and they are human. There can be, there can be other issues there which you could speak to a lot better than I can. But, um, you know, when you're thinking about ads, again, I think to go back to the point from earlier, you don't need to just decide on a whim, oh, we need leads, we got to run ads. You might be, be taking something that can be expensive and flushing it down the toilet. It's all about the the return. And if you can take $10 and have $10 create you on average $100, that's not expensive. That's an investment, and a really good one at that.
All right, so we've hit on one-to-one outreach, we've got LinkedIn DMs, we've got cold email, we've obviously got cold calling. And you know, some of this is like— it's funny, at Underdog we had this— I wouldn't call it a revelation, but just a moment where I had to talk to Karen, you know, probably talk to you about over the years too, where it's like Everybody comes to us, says they want marketing services, but what they really want is leads. Yeah, right. Like, I mean, let's call it what it is. Like, marketing is great. Everybody wants to have a cool brand and get impressions and views and likes and all that. But it doesn't matter if it doesn't turn into business and you can't get business without leads. And again, warm, cold, whatever, you still got to have them. And so, you know, the thing that people often— if you're newer in your journey in entrepreneurship or whether it's in payroll or anywhere else, you've got to know that you've You've got a phone full of leads before you start. So you've got your contacts direct that you can reach out to, call, text, email. Now you've got, go to each social channel, work through it. All right, now I've got all my LinkedIn connections. Now I've got all my Twitter connections. Now I've got all my Facebook friends. Now I've got, you have a ton more leads than you ever anticipate. It's just like you're too scared to sell is the reality, right? Like, and this is, you know, I've had a lot of hard conversations with people over the last couple of months where they think they want to start a business. And then I explain to them how to go out and validate the idea. And then they go, yeah, that's— I'm definitely going to do that. And then you'll check back in a couple of weeks later and they'll be like, dude, no, I mean, you know, I'm just busy building the product. It's like, yeah, well, yeah, a lot of products been built with no users, man. So, so we've got to be conscious of that. But so we've got, hey, let's not leave the phone out of it, right? That's so important. The phone still works. My phone rings less than ever. Let me just say that again. My phone rings less than ever on like legitimate calls. So especially from your local market, you've got this opportunity to like call from an 803 number or if you're in Columbia, South Carolina, and get directly through to somebody, every other call is coming through as spam. So if you pick up your cell phone and make a call to somebody, you're not showing up as spam and you can cut straight through the noise. But the kind of last piece that I think when we talk about, you know, one-to-one, one-to-many, warm, cold is content creation, right? So organic, attracting people to you by one-to-many by creating content. And again, that can be cold in terms of I'm just firing a piece of content out there and I'm hoping people find it through SEO or whatever the case may be, or warm in that I've built an audience of followers, and now I'm posting and they're reading it, right? So LinkedIn would be a good example of that. What, what things are you seeing work best in terms of organic content in 2025?
Let me go on another little, uh, I guess mini rant about some of the things that maybe don't work, or just maybe some, uh, miscalculations or some things that, that you need to know. So a lot of times content— to go back to what you said about clients coming to us saying they want marketing, and, and you kind of have to dive into what that means. One of the most common things is we want you to do some blogs for us. And there's nothing wrong with that, right? I'll explain why. We want you to do some blogs and we want you to do social posts. Social posts are a big client ask and we do them, we fulfill them, right? And we try to do the best job we possibly can. But if you're doing social posts just to slap them on a calendar or cross-post them, you know, okay, cool. Are you wasting your time and money? Are you wasting your money hiring us? Are you wasting our resources by your choice on something else we could be doing that would help you more? Like cold email, maybe. Let's talk about it. Let's figure it out. Let's, let's take those one by one. Social. A lot of people think, I'll make some social posts, people will see my business. Not necessarily, especially on platforms, LinkedIn, Facebook, that reward you for paying them. Twitter, X, you know, get your blue checkmark. Oh, there's another level of blue checkmark that'll get you seen more, right? The more you spend, the more you'll get seen. And so So just filling out a social calendar and posting doesn't necessarily help you. Your engagement is actually more important. And there's, there's nothing wrong with posting a social because remember the example I gave earlier, if Matt Vadie DMs me, I would like to go to his profile and see what he's written about. Does he know what he's talking about? But if you think people are just gonna magically find your content, if you post every now and then, probably not. But are you engaging with people on social, commenting and not just putting in the comments? Thumbs up or cool comment.
Let me, let me, let me, let me break up right here, here, because I think I gotta validate Chris here and make sure people know, because Chris is a Twitter king. What's the Twitter handle?
It's @GCChrisClark if you want to read about South Carolina Gamecocks stuff.
Better, Chris Clark.
So another random musings, right?
He, he proves out a couple things, right? So niching down, which was the episode Matt Umholtz and I just talked about a lot about niching down. You're talking about the Gamecocks when he got 20,000 followers on there, 30,000 followers. And you know, if you follow his timeline, and I always joke with him, I'm like, I'm your bro, so I just hit like blindly on everything you posted. And if you're a bro or a sis out there and you're listening to this and you're like, hey man, you're scrolling past one of your bro's or sis's, uh, posts, you hit that like button. Yes. Like, I mean, that's just what people should be doing for their friends, okay? Like, I— it takes me no time. And if you're a real bro, you hit the see more so that expands it and the algo knows you're interested. Maybe just hover there for a couple extra seconds, let it know you're reading the post, right? So I think that's it. Again, is this, is this a life advice episode? I don't know. It's partially that. So, so Chris knows and has— if you look at Twitter, is probably the training ground for social media better than any other, because in order to be relevant on Twitter, and you tell me if I'm wrong here, you have to post what, 5, 10, 15, 20 times a day to really grow an audience on Twitter?
Yeah. And admittedly I don't take my own medicine here sometimes. My tweet volume has gone down over the years, but the way to grow an audience is you definitely have to post more. And Twitter is more informal, is shorter, it's more stream of consciousness. Is it more toxic? Yes, certainly. But like it's, and it's better for certain audiences. One thing that we found, by the way, with Underdog Sports, which is our sports marketing arm of Underdog Digital, is we were kind of trying to apply at first, or we thought, hey, You know, let's, let's do some sports outreach for certain types of clients on LinkedIn. It works everywhere else. Well, it does for founders and B2B and tech and software in the sports space. If you are trying to, if you've got a product for say high school sports coaches or youth sports coaches, you're not gonna find them on LinkedIn. They're on Twitter though. They're on Instagram, right? So that's an example to go back to the cross-posting. Let me just post the thing everywhere. Find your audience. Where do they live? And then what do they want on that platform? Right?
So your engagement is, is very important.
Important. You know, I appreciate your likes on Twitter that, you know, if I didn't know you, I'd be like, who's this guy who likes my posts at 10:30 at night all the time?
Sometimes 1 AM, 1 AM, whenever.
But you know, your interactions help. And they're actually examples of people who, you know, you, you look at, say, their LinkedIn, and they don't post every day, but they're interacting like crazy with people, and they're adding value, and they're going people's DMs, and maybe not just selling them something, but seeing they can help, and those people do extremely well. So it's not just about, let me post 1,000 things and see what happens, right?
Well, I think it kind of breaks that unfair narrative as you're talking here. I'm thinking about it of like the lurker versus the poster, right? Or it's like, I'm thinking about a networking event now in real life because, you know, as you're talking, I'm thinking of the cliché, like it's called social media for a reason, right? Be social. But like, how do you act at an event would be the question, right? So yes, some of us are going to be up on the stage on occasion, right? And I love to post, and I, I— it's just, it's worked well for us. So it's a, it's a discipline I stick with, and that I, I write the post, I do the posting, I do all the things, and the engagement like you're talking about. Because like, yeah, not only would I show up to the event and step up on the stage and maybe give a 5-minute talk, but I'd also hang out and meet people and talk to them and send, you know, have a one-to-one conversation over on the side. I would, you know, have a conversation with a group. I'd contribute as a comment on a post, right? So like, look at these things in real life. So a DM is your one-to-one pull-aside conversation. Commenting on a group post or where other people are commenting is us having a small group discussion. Posting is getting up on the stage and sharing something with a group of people that you have the opportunity to do. And I've beaten ad nauseam on this podcast why you should post more. But I'll say this, and I'm going to call my shot here on this because so Twitter kind of went through this ebb and flow, I think sort of pre-Elon, where there was this moment in time where it got to be where collecting followers was all that mattered and people I would do the follow unfollow move. Do you remember this? Were you on Twitter at this point? I'd follow Chris. As soon as he followed me back, I'd unfollow him and I would just keep doing that until I had 10,000 followers and I was only following, you know, 20 people and it would look like I was some sort of Twitter influencer. I don't think that game works as much anymore, but I'm starting to notice it. Not the same version of the game, but the same collection of connections happening on LinkedIn, which tells me this platform is on the other side of the hill. And I'm hoping I'm wrong on that because we don't have a next place, right? I mean, obviously short-form video is the thing, but there's still going to be a place. There will always be a place for text. But between the AI posts, the AI comments, and the sort of harvesting of connections, I fear our golden era of LinkedIn is getting put behind us. It doesn't mean we don't have a couple more years of great biz dev opportunities, but all the signs are there. And I mean, it starts to go back to, you know, not to go off on too long of a tangent here, but we used to get great organic reach. Tremendous organic reach. Do my best Trump impression there. No political thing there. But as soon as those words tremendous left my mouth, I felt like that was appropriate. And then as soon as they rolled, as soon as they get you all addicted to the dopamine that comes with all those likes and all that reach, what do they do? They roll out paid influencer ads. Then the reach drops and then it drops more and then it drops more until you just get so desperate that you're like, I might have to pay for that reach again. And so we're already already there. And that's every social platform has gone through that iteration, right? Facebook did it, Twitter did it, Instagram did it. Like, they all do it. Like, it's, it's just the playbook that LinkedIn followed.
Well, and that's why I think, um, to the extent that you can take advantage of the algorithm when we're talking about LinkedIn, Facebook, which I don't like as much as a— like, it's got some great value. I personally don't like it as much. I don't like dealing with it as much, but that's like a personal preference. Right? Like you deal with things all the time in business you don't like. Twitter, I like, it's fun, right? Like it's, it's better, it's easier to interact with people, but you don't want to be beholden to those platforms, right? Because you're just an algorithm change away. You know, you think about YouTube, a lot of people, there is kind of a phase, you know, on YouTube, it still happens where we don't like what you said, demonetized, boom. And if your whole business is built on it, whoops. Now payroll companies, which you're talking about here, that's not going to be you, but the general broader point again, That too, don't bank on, I'm gonna make a bunch of social posts, you know, that are just kind of cookie cutter and those are gonna help me. You need to find, be able to deplatform people. And I would say just you, like, honestly, if I could dumb it down, think of LinkedIn or Twitter like a phone. Like you made a great point about the phone. Like the phone doesn't have an algorithm yet, I guess, right? Like there's no, the phone is a tool that you can connect with people. So yeah, post and try to take advantage of the algorithm, but bank on your reach, you know, not depending spending on that and bank on your reach maybe diminishing as we've seen over the years. Those will probably just continue to happen. But what it is, is it's a tool that you can use to reach out to people like a phone, like an email. You can use social media in those same ways as kind of just a mechanism to get in touch with people and share ideas.
You know, I have a good friend and mentor who is a multi-preneur like I am. And one of the things he, he told me early on when I sort of fell into his Michael was like, you know, he does a really good job of keeping together his list of like true connections. And so, you know, we've got these big massive email lists, but I don't really have a great list of like, you know, you and all my other peers and friends who like, when I want to just send a blast to like the people that know me well, I don't really have that, but he does. And he's like, look, if you're in my circle, you can expect at least once a year, I'm going to reach out to you to buy something from one of my companies. And like, you know, he's just like, that's the expectation. You want to be in the circle of trust, Like, just know, like, I mean, friends do business with friends, you know, like that is a totally fair thing to say, thing to do. And I don't think as many of us do it. I don't do a good job of it. To your point, I mean, you know, it's almost cliché at this point, but like you've got to own as much of your audience as you can. So when you're, you know, even though you've got a big YouTube following, like you always want to drive them to a form to get their email so that you can, you know, bring them to the next platform with you when you have to make that move, which is a great segue into we now have a signup form where you can get emailed every time there's a new episode of Payroll In, and we just launched this great— it's funny because Matt mentioned it in our pre-interview. I was glad to hear it because Matt's an industry vet in the payroll industry, runs, I think, one of the top 3 largest private payroll companies in the country. We are distributing a weekly newsletter, the top 5 headlines in our industry from the week, top 3 things from the competitors, growth tip, and a couple other things in there. We're refining it. We're continuing to improve it. But I'm physically curating this thing myself because I've been on some of these other newsletter lists before. Where they're just clearly got somebody, you know, either a virtual assistant or a scraping tool pulling together 20 links that are, you know, 15 of them are garbage. I'm getting rid of the 15. I'm leaving you with the 5. So make sure you subscribe. We're going to put it in the comments of this video because certainly by the time this video is done, the Underdog team will have it ready for me. But you go back to your point and I know we're at time here and I'm going to be conscious of your time, but I just, you know, Karen, just the other day we were, you know, not only am I the Hair Club president, I'm also a client. So, you know, I'm having my monthly meeting with Underdog Digital as guru. And I was like, let's just stop posting from our company account. Like, this is stupid. There's nothing— all this is doing is letting people know we're alive. Nobody's reading them. Nobody's engaging with them. Nobody's— there's nothing here. We're posting from individual accounts. My account, they get engagement, they get reach. We can share real perspectives. But company pages are just dumb and they're done. I don't think it's— there's any value in posting from your company page. And it's so obvious when you go and look at these accounts with 2 million followers, they'll get 3 likes on a post. And it's like, why? Somebody spent the time to cross-post that. Schedule it, whatever. Even if it's easy, it's still, it's another wasted minute. And every waste of motion is a waste of motion, right?
No, you're right. And I mean, if you're thinking about, I actually get this question a lot. We've got some social posts. Should we post them from the company page or a person? And the answer is always a person. But you also have to say, you know, if it's a Merry Christmas or Happy Veterans Day, you know, things like that, then if the person posts it, great. But like, let's, you know, add some perspective to it or something like that. Let's make it interesting. And, you know, people like people and not brands and You know, even with, with what we do in the, in the sports space, it's, it's about, it's a connections, relationships industry. Like sports just in general is that, and the more people you know, the better relationships you have, it's always better. People build brands. Now there are huge businesses out there where maybe you just need a service. So the people maybe don't matter as much, but in a lot of sectors it matters a great deal. So don't just to, to kind of bring home the point. Don't just post a bunch of stuff to a social media page or your pages because you feel like, ah, that's just what people should do, right? There's a lot of other things that you should prioritize for your marketing and, and for your sales, right? Because that's not really, when you're looking at what brings in leads, oh, I posted 4 things this month on our company LinkedIn page is probably not gonna be one of them.
So we have given you a bunch of ways that— not just ideas to generate leads, legitimately the ways that we are generating leads for our clients in the payroll industry through a marketing agency. So that's pretty valuable information. And all I'm asking from you is— it's pretty simple. If you've been around for a minute, you've heard me ask about— tell you the gentleman's agreement and the lady's understanding. If you're newer to the show, you know this. So we create all this great content for free. We don't charge anything for this. This took us, uh, we're already over an hour of our time we took out of our day. All I'm asking from you is to just hit that little subscribe button, hit that little like button, just go ahead and smash it. I'll wait. And I love saying smash that like button. It makes me feel like a real YouTuber. You know what I mean? But that's it. I mean, we do all this for free. That's all I'm asking. It's 2 seconds. Just go ahead and do the thing. And we're, okay, if you stayed around this long, clearly you're seeing the value, dude. Come on. Just hit that like button. We appreciate you, Chris. Thank you for coming in and dropping bombs today.
Appreciate you as always, my friend. Always good to be on. Thanks for having me.
Thanks, brother.










