Latest / Scrappy but Successful [Consultant's Personalities When No One's Watching] / 30. Why Most Small Business Marketing Misses the Mark with Jen Best

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30. Why Most Small Business Marketing Misses the Mark with Jen Best · Scrappy but Successful [Consultant's Personalities When No One's Watching]

• 0:03
  What's happening everybody? Welcome to Scrappy What's Successful. It's a show where I sit down
• 0:07
  with your favorite consultants and we find out if they're successful today because they're sophisticated
• 0:12
  or because they're a little bit scrappy. I'm your host, Jack Tompkins, CEO of Pineapple
• 0:16
  Consulting firm, always helping small businesses become more data driven. Fun fact of the day,
• 0:21
  related guest tour, or related fact to our guest here, Raleigh, North Carolina is the
• 0:26
  only city that was actually built to be the capital. So they had a whole
• 0:30
  structure, whole plan in like 1700. to actually make one building the center of the
• 0:35
  city and it was going to be the government city. Everything else just kind of
• 0:39
  happened. So that's, that's my fun fact for Raleigh. But that's neither here nor there
• 0:44
  today. I'm joined by my friend, Jennifer Best. She's the founder of Copper Compass Group.
• 0:49
  She's a two-time entrepreneur in the digital marketing space. Current company helps small businesses and
• 0:53
  startups win online. She's a HubSpot partner, she's an SBA award winner, she's the incoming
• 0:58
  president of the AMA chapter in the Triangle North Carolina chapter. Jennifer, we know that you are successful today, but the question we have for you, do you think that you fall more on the sophisticated side or more on the scrappy side?
• 1:02
  Wow. Well, thank you so much for having me. I'm laughing because nobody would probably
• 1:07
  ever call me sophisticated. Nobody who really knows me would ever confuse that question. I
• 1:11
  definitely fall under the scrappy side. Borderline disorganized, but getting better at that. But scrappy has sort of been my middle name throughout my entire career. So that's sort of what I pride myself on.
• 1:14
  Hahaha Nice, yeah, it's all about, you know, it doesn't have to look pretty, it doesn't have to be the most organized. We get stuff done though, and especially in the online space that you work in, like, there's just, there's a lot of scrappiness that has to come from, okay, let's get this together and we can perfect later, kind of continuous improvement mindset almost, right?
• 1:19
  Right, exactly. and I'm gonna also challenge your fun fact, which I didn't know that about the city of Raleigh, but a couple months ago, my husband and I went to New Bern, North Carolina, which was the first capital of North Carolina.
• 1:23
  Okay. and learned all about the history there and then how they eventually moved the Capitol to Raleigh. So it tracks, definitely tracks. I didn't know that that's how they built it, but knowing downtown Raleigh, the way that it's built and designed and structured, it makes sense. It looks like it was built with that in mind. So that's a great fact. I'm glad you found it.
• 1:28
  . Perfect. Okay, good. I'm glad I got a stump and a learning. But yeah, I'm guessing when they moved from New Bern, they probably said, all right, let's do it right this time.
• 1:33
  You Yeah, that would make sense. New Bern's a very, very small town. It's close to the, I guess, the Eastern Shore. yeah, it's a very, really, really some much bigger populace now. And I'm sure was then too.
• 1:37
  Yeah. And I mean, look, it's a scrappy way to do it. Hey, we're gonna try some of a newborn. Great. Didn't work. Let's do it better the second time. Did you grow up in the area? Did you have any entrepreneurs in the family?
• 1:42
  Mm-hmm. Yeah. Scrappy all the time. Okay, so first question, no. I've lived here since 2020, but I've had family in the area for the last couple of decades. I grew up in New Jersey, went to college in Delaware, lived in Maryland. I kind of keep going south. This is as far south as I'm going though. Like further south is not on my plan. I grew up in a family of entrepreneurs. So my father was an insurance broker who basically kind of was an independent broker working for different companies.
• 1:46
  My mother was a stay-at-home mom and then kind of, you know, mastered the side hustle before you called it side hustles. She had party planning businesses on the side and she did some real estate for a while. So she really instilled, both of them instilled entrepreneurial brain and mindset. And my sister is a long time business owner here in Raleigh. So it's, I joke that it's genetic. Like it's definitely in the DNA.
• 1:51
  I was really excited when I got the opportunity to go back into entrepreneurship because I think that it's exciting, it's challenging, it's definitely scrappy, but it's sort of the way I was brought up. And so it really feels like it fits me more comfortably than corporate.
• 1:56
  Isn't that funny? Cause corporate's supposed to be the here's your dream. It's just nine to five. You get to have a life. You get to have stability and all this stuff. And you're like, Nope, that just sounds like it's not for me. And so do you
• 2:00
  I've tried it. I've done it. You know what? It's going to be great for a lot of people who want to maybe get to do things in their career that they might not be able to fund themselves. So for me, I worked in corporate probably about 15 years. I got to travel to Europe.
• 2:04
  on company. Thank you very much company. I got to learn how to develop programs, work with international audiences, get on stage for the first time in front of a couple hundred people. It definitely was a learning experience. And I'm kind of glad I had that through my career, because I think it makes me appreciate where I am today even more. Because when you've worked in companies, and you find yourself not feeling 100 % fulfilled,
• 2:08
  and you realize that there could be a better way to do this and you bring it to leadership and leadership's like, well, I don't think so. Then you're like, okay, well, maybe I'll take that idea over here and do my own thing. And so it really kind of feeds into like the creative side of the things that I want to do in my life. So it's lot of fun.
• 2:13
  Yeah. Have you always had that like, obviously it was part of the family was part of the probably the dinner table conversations I imagined too. Are you starting a lemonade stand as a kid? Like are you selling candy at school at all?
• 2:18
  No, but when my mom did the party planning business, my first job was helping make balloon arches at one of the party. Yeah, I learned a very valuable skill. I can now make a beautiful, you know, arch rainbow. I know how to do it. No, it was really just, I mean, I worked from a very young age that, you know, might have been a little young, but as soon as I could work, I did. And I worked a side job pretty much all through high school, college and then some. So
• 2:22
  Okay. I don't know if that's probably my parents are where I got the work ethic from. But yeah, I mean, it really sort of, mean, I had some crazy, some crazy jobs in high school though. Aside from doing that, I worked at a Six Flags Park, know, swinging churros and hamburgers. I worked in a party store also there and I did a lot of camp counseling. So a lot of kids. Yeah.
• 2:27
  Yeah, what do we got? Okay. Okay, interesting. You must have stories from those. Like give me a six flags. Like there's gotta be some kids who were really upset about not getting a churro or something like that.
• 2:32
  I don't know about that. But I think the funny thing is that it was a Six Flags park and I hate roller coasters. It just happened to be near where I grew up and my friends work there and they helped me get the job. And I was like, well, that sounds kind of cool. I never went on a single ride when I worked there. I just like the environment. I'm more like the, you know, maybe Disney walk around Main Street USA and see the sights and watch the people.
• 2:36
  Okay. I don't blame you, I'm not a big rollercoaster fan honestly. Okay, would you do a like a water slide instead of a roller coaster? Okay.
• 2:41
  Yes, that's the one. Actually, the log form is probably the one thing I would do.
• 2:45
  Okay, I was the exact same. I have no problem with the water slide, but I would have enjoyed being a kid at that Six Flags, because you would have been like a friendly face of like, here, let's just eat churros instead. It's way more fun and safe. Yeah. Okay, so you've always got something else going on the side. You've got corporate for a decent amount of years. And then you're saying, all right, I can kind of like take this idea and kind of make it my own. When do you, I assume you start
• 2:50
  Thank Absolutely, my love for churros started early.
• 2:55
  the first business on the side then while you're still working corporate.
• 2:59
  So, yeah, so my very first business, I started back when my kids were little. And so I was not working at that time. We had just moved and I knew I wanted to learn something. But this time around, it sort of was a circumstance of the pandemic. I moved in March of 2020 to start a new job in a new state. And about a month into the job, they...
• 3:04
  Nice. decided, thankfully, we had jobs. They kept almost everybody, and they only furloughed a small handful of people. But I was fortunate enough to avoid that. But everybody in leadership too took pay cuts, which we were more than happy to do because we had jobs. So because of that, and because we had just built a house and my husband hadn't found work yet, I started doing more side projects again. And so I had worked with a creative agency in my last company when I was in Maryland and, I reached out to her and I said, Hey, if you ever need any help working on SEO strategy or UX review or anything like that, SEO, send it my way. I'm happy to kind of, I need to supplement. wanted to pick up a couple of projects every month on the side. And that was, that was kind of the turning point to kind of shift me back into entrepreneurship because I did that pretty much on and off until I started the business full time last year. It gave me exposure to some really, really different kinds of companies that I hadn't worked with before. one was like a brew brewery. That was fun. Another was like an Africa Safari trip company, healthcare agencies. And then there was some like financial education, different things like that. But it most of my career I spent in B2B.
• 3:08
  Whoa, okay. And so for somebody coming out of B2B to get to work kind of in the B2C space on like a dip your toe in the water basis, it was sort of, it was really fun because I got to learn these new industries, but also how cool, right? Like African Sephora's, yes, please. So from there, I really started ramping it up and I had been transitioning late 2024 into 2025 when things just shifted at the company I was at and I
• 3:13
  Right. Fortunately, I already had a head start. So I was able to flip the switch pretty quickly and picked up my first clients within the first month. So everything was set up behind the scenes, the LLC, all of the systems. I just needed to get the leap, know, take the leap. When leap was shoved a little bit more, I was like, okay, all right. It took about five minutes of whoa, whoa, it was me. And then I was like, oh, wait a second, working towards this the whole time. So.
• 3:18
  Right. Yep.
• 3:22
  Nice. Okay. I have to ask as a marketer, I just came from a conference was it's all marketers and the importance of the ICP, the ideal client profile is as you know, it's the core of everything. And I keep thinking like, that's such an easy, obvious statement. But then I thought about all the different things that impacts, and it is such an important fundamental thing that has to be so precise. And so then you start and you're like home healthcare and African safari sign me up. How do you define your early ICP?
• 3:27
  That's a great question. For me, I'm probably going to give more of an example from the clients that I work with directly because those clients were ones that I worked with through an agency. And so the agency had client facing conversations and then handed me some decent profiles ahead of time. So I didn't have to necessarily do that research. They kind of handed it to me. But I work with a couple of clients now that
• 3:31
  Okay. You know what? It's interesting. ICPs are really, really interesting because they're not static, right? Like what I started with, I'm working with a client right now where we went maybe a little over a year ago. We've really dug in on a couple of different ICPs. I rolled up my sleeves. I got in, started doing a lot of research and then sanity checking things and back and forth. And we did surveys. We did all of this stuff. And now we're getting ready to go through the process again with some different audiences. It's a little bit daunting, but It's important, I think the biggest thing that I would say about ICPs is it's not to me as much of the detail oriented because people are fluid. They are changing their minds all the time. Platforms are coming to be all the time. mean, just this week, Google's like, hey, guess what, guys? We're going to change how we do Google. That changes everything we're doing. So we kind of have to take the ICP with a grain of salt. who they are and how they act today. That might not be the case in three months or six months. Their behavior might be very, very different. And so I go at it maybe not with as strict of constraint, but also just trying to get under, how do they purchase? How do they make decisions today? Where are they hanging out today? Where are they asking questions? Those type of things that I think are consistent aside from where they hang out and what they do.
• 3:36
  Bye. But yeah, AI makes it a lot easier to do that research today. It's available, but should never obviously replace the critical thinking that has to happen when you're creating ICPs because don't take it as what it says. I've seen that time again. I'm sure you have to.
• 3:41
  Of course. Yeah. It's funny. I've been telling my team and we're, we're rolling on AI product. We're doing all this stuff. And the, the order of operations still think first, then ask AI. Right. And so in the context of an ICP and marketing, it's still that same order of operations. Right. And so what you go into is much more like the, what's the, what's the marketing, like the cycle graphics, like the personalities of the ICP a little bit. that? Yeah. Okay. Yeah. I mean, back before we were all using AI mainstream, I would say I would approach it. Here's how I approached it at a previous company. took a look at our existing customer base, anybody who'd purchased from us two or more times in the last six months. I found them on LinkedIn. I started doing some digging into how they talked about what they did, what their pain points were and started gleaning. Shaping these personas. So like we were in the event space and so we went from just saying event planners to be able to say an event planner at a corporation is very different than one at a university or an association. They have different needs and different pain points or somebody who plans events for companies is also a separate demographic. we found like subtle nuances in education and age pain points for sure if somebody is an event planner on behalf of a company. then it's their reputation, their business, their business owner, right? So that's sort of how I used to approach it. Now we've got agents, agents and agents and agents and agents. The hardest thing is learning all the agents and figuring out where to put them. But I think that... That still served me very, well because we were able to customize messaging accordingly by understanding pain point a little bit better than we did before. So that's sort of my next plan. It's a really good plan. And I, again, the same hammer stuff we just had, 300 marketers added. A couple of people talked on agents and how to use agents, like that too. The overall consensus amongst those 300 people was I've totally heard of that. I totally want to try it, but it is totally not in the next three months. And I would give you a whole lot of credit because even though maybe that feels just like, okay, one thing talking to one, but like, that's pretty big. And doing any use case that actually saves you time and you can actually have a real benefit from it. It's a big win right now because everybody's very familiar with GPTs at this point, right? And Claude is insanely powerful. It's doing all sorts of crazy stuff. And by the time this episode comes out, it's probably going to take over the world. But agents are kind of like that next front of, man, that sounds really exciting. I don't even know where to start. So you've started and you've successfully implemented it. I'm going to give you a whole lot of credit there. That's awesome. nice, okay, okay, using some automation, pretty classy. Do you recommend books or do you recommend podcasts? Okay. Always books. I like podcasts too, but I'm a big reader. I was the instigator in my neighborhood book club, which probably everyone's like, yes, we know who you are. But no, I mean, I have always loved to read, I would say like the last couple of years I've really gotten back into it and we sort of to challenge ourselves. So I'm definitely a book nerd. Okay. Okay, okay. Take me inside the office. How many monitors do you have on your desk?
• 3:45
  Right now I have one monitor and one laptop screen. Okay? Yeah, I know it's kind of boring, but my husband's building some new shelving in here. It's just not ready yet. It's in the garage. It's almost done. Fair enough. Okay, okay. Do you have a docking station set up or are all the wires kind of just individually going into the laptop?
• 3:50
  So it's a Mac, so there's not a lot of options when you're plugging into a Mac. I have not a docking station, but like those attachments that have multiple plugs, like USBs, HDMIs that go into them. they're kind of like, it's a little bit of a process, but it's not, I mean, I couldn't connect all of the things that I need to connect unless I use those things. So Gotcha, okay, a couple dongles plugged in. Okay, so you're trying to schedule a meeting today. Are you saying like, Hey, I'm free Thursday afternoon, or are you sending a calendar link?
• 3:54
  I am now sending a calendar link because it's so much more convenient for people to book plus HubSpot offers that the meeting scheduling link and then it puts everything automatically into HubSpot for me and I don't have to type it. Nice, okay, okay, using some automation, pretty classy. Do you recommend books or do you recommend podcasts? Okay. Always books. I like podcasts too, but I'm a big reader. I was the instigator in my neighborhood book club, which probably everyone's like, yes, we know who you are. But no, I mean, I have always loved to read, I would say like the last couple of years I've really gotten back into it and we sort of to challenge ourselves. So I'm definitely a book nerd. Okay. Okay, okay. Take me inside the office. How many monitors do you have on your desk? Right now I have one monitor and one laptop screen. Okay? Yeah, I know it's kind of boring, but my husband's building some new shelving in here. It's just not ready yet. It's in the garage. It's almost done. Fair enough. Okay, okay. Do you have a docking station set up or are all the wires kind of just individually going into the laptop? So it's a Mac, so there's not a lot of options when you're plugging into a Mac. I have not a docking station, but like those attachments that have multiple plugs, like USBs, HDMIs that go into them. they're kind of like, it's a little bit of a process, but it's not, I mean, I couldn't connect all of the things that I need to connect unless I use those things. Gotcha, okay, a couple dongles plugged in. Okay, so you're trying to schedule a meeting today. Are you saying like, Hey, I'm free Thursday afternoon, or are you sending a calendar link? I am now sending a calendar link because it's so much more convenient for people to book plus HubSpot offers that the meeting scheduling link and then it puts everything automatically into HubSpot for me and I don't have to type it. Nice, okay, okay, using some automation, pretty classy. Do you recommend books or do you recommend podcasts? Okay. Always books. I like podcasts too, but I'm a big reader. I was the instigator in my neighborhood book club, which probably everyone's like, yes, we know who you are. But no, I mean, I have always loved to read, I would say like the last couple of years I've really gotten back into it and we sort of to challenge ourselves. So I'm definitely a book nerd. Okay. Okay, okay. Take me inside the office. How many monitors do you have on your desk? Right now I have one monitor and one laptop screen. Okay? Yeah, I know it's kind of boring, but my husband's building some new shelving in here. It's just not ready yet. It's in the garage. It's almost done. Fair enough. Okay, okay. Do you have a docking station set up or are all the wires kind of just individually going into the laptop? So it's a Mac, so there's not a lot of options when you're plugging into a Mac. I have not a docking station, but like those attachments that have multiple plugs, like USBs, HDMIs that go into them. they're kind of like, it's a little bit of a process, but it's not, I mean, I couldn't connect all of the things that I need to connect unless I use those things. Gotcha, okay, a couple dongles plugged in. Okay, so you're trying to schedule a meeting today. Are you saying like, Hey, I'm free Thursday afternoon, or are you sending a calendar link? I am now sending a calendar link because it's so much more convenient for people to book plus HubSpot offers that the meeting scheduling link and then it puts everything automatically into HubSpot for me and I don't have to type it. Nice, okay, okay, using some automation, pretty classy. Do you recommend books or do you recommend podcasts? Okay. Always books. I like podcasts too, but I'm a big reader. I was the instigator in my neighborhood book club, which probably everyone's like, yes, we know who you are. But no, I mean, I have always loved to read, I would say like the last couple of years I've really gotten back into it and we sort of to challenge ourselves. So I'm definitely a book nerd. Okay. Okay, okay. Take me inside the office. How many monitors do you have on your desk? Right now I have one monitor and one laptop screen. Okay? Yeah, I know it's kind of boring, but my husband's building some new shelving in here. It's just not ready yet. It's in the garage. It's almost done. Fair enough. Okay, okay. Do you have a docking station set up or are all the wires kind of just individually going into the laptop? So it's a Mac, so there's not a lot of options when you're plugging into a Mac. I have not a docking station, but like those attachments that have multiple plugs, like USBs, HDMIs that go into them. they're kind of like, it's a little bit of a process, but it's not, I mean, I couldn't connect all of the things that I need to connect unless I use those things. Gotcha, okay, a couple dongles plugged in. Okay, so you're trying to schedule a meeting today. Are you saying like, Hey, I'm free Thursday afternoon, or are you sending a calendar link? I am now sending a calendar link because it's so much more convenient for people to book plus HubSpot offers that the meeting scheduling link and then it puts everything automatically into HubSpot for me and I don't have to type it. Nice, okay, okay, using some automation, pretty classy. Do you recommend books or do you recommend podcasts? Okay. Always books. I like podcasts too, but I'm a big reader. I was the instigator in my neighborhood book club, which probably everyone's like, yes, we know who you are. But no, I mean, I have always loved to read, I would say like the last couple of years I've really gotten back into it and we sort of to challenge ourselves. So I'm definitely a book nerd.