This week we interview Skip Wilson, Founder and CEO of D.R.A.F.T. Ad Technologies. Skip breaks down how to pivot in startup to maximize your team and your bottom line. https://draftadtech.com
00:00 SPEAKER_01 Well, hello, Chaos fans, P1 listeners, as we were just talking about that. We'll get into that in just a minute. But welcome to Hello Chaos. This is a weekly podcast exploring the messy and chaotic lives of founders, entrepreneurs, and innovators. Hello Chaos is one of the many resources brought to you by OrangeWIP. That's OrangeWIP, W-I-P, for Work in Progress. OrangeWIP is a multimedia company dedicated to serving founders and entrepreneurs in affiliate cities through hyperlocal online platforms designed to inform, inspire, and create connections to help founders along their journey. OrangeWIP is part storyteller, part how to guide, and part navigator. We are the megaphone for founders telling real, raw, and honest stories. And why our mantra is where aha meets oh shit. My name is Jennifer Sutton, aka JJ, that's my nickname. I am the founder of OrangeWIP and your podcast host today. We record live every Wednesday at 3 p.m. Eastern Standard Time and publish on all podcast platforms on the following Sunday. So you can find us anywhere. So on our podcast today, we're welcoming Skip Wilson, founder of Draft Add Technologies.
01:35 SPEAKER_02 Welcome, Skip. Thank you. Thank you. Nice to meet you.
01:39 SPEAKER_01 You're welcome. And Skip, this is our 53rd podcast. Sweet. So, you know, we're making it real.
01:46 SPEAKER_02 That's a big deal. You know, Seth Gooden said any podcast that makes it past 50 episodes,
01:50 SPEAKER_01 I mean, that's quite an accomplishment. It is. I was like I was looking at a stat of like the average podcast frequency is like 12 or 16. I mean, it is a low number. So, yeah, the fact that we've we've hit that benchmark, we're doing great. Now, you and I go way back. So everyone, all of our listeners and our viewers, you know, we you and I go way back. I heart days. Yeah. I want to say we've known each other for 15 plus years.
02:21 SPEAKER_02 Yes. And maybe even longer than that. It's hard to say if we bumped into each other when I was freelancing.
02:27 SPEAKER_01 But yeah, for Jackson, so probably. I know. Yeah, you were. But you've always been on, you know, the the media side of the table. And I was always on the buyer side. So we can get into to that. And then you left and I heart after many years and started your own company. But man, did you figure out a solution to. Buyers like me out there. So so just talk about, you know, draft technologies and why you founded that. What you know, why that solution? What was that? What was that journey like?
03:13 SPEAKER_02 Well, so it really started from decades of answering two questions or like two things that I like, hated saying all the time, which I hated the phrase. I hated saying all the time, like, oh, well, after like month three or so, it'll start getting better. Like I hated having to say that there's some truth to that. But but I'll talk about that. But I also hated having to answer the question of like, you know, oh, well, what kind of results can we expect? It's like a very reasonable question, right? Like if I'm talking to a financial advisor or something else, it's like they can say, OK, well, about a 7% annual return or whatever. Like in the marketing world, there is like, it's just sort of a wild guess. And so I hate I didn't like not having solutions to that. And then the three month thing, like I just hated it. It only gets better after three months if things are being tweaked and changed.
04:04 SPEAKER_01 Right. Right. Well, and you and you only control so much. So I'm going to break down for people that aren't in media, because here's a thing I've recognized, not a lot of people know what we do, like what our backgrounds are, you know, from a media planning and buying perspective. You were the one that I would go to. You would sell me those those ad placements, those, you know, I caught time, air and space. Yeah. That I always say, you know, the in the ad agency, you know, that's where my background is and working with, you know, big, big brands and having, you know, millions of dollars of that I was responsible for. So you talk about like your biggest frustration, frustration of me coming to you going, is this really going to work? What should we expect? What's the return? Is this the best place for my, you know, for my outlet? I mean, those are the things that as a media buyer and planner, that's what we're trying to figure out, too. Right. Client comes to you and they say, hey, here's, you know, I mean, I think one of my biggest clients and I was managing a 40 million dollar account. Right. Like where to place that or in a spot market of you've got two million dollars, you know, and you're buying in three markets. They're putting a lot of pressure on them, you know, in an agency, the media department of are you, you know, because it's reasonable. Normally when you spend 40 million dollars, you have some idea of what you're buying. You hope you get some kind of return on that investment. And it was never, you know, and it was when I entered into the agency world in that media space, it was never the pressure of the creative department. It was always like it was me having to stand up and it was the client going, well, I didn't see sales. I didn't see the phone ring or I didn't see butts in seats. Jennifer, you tell me why you chose this. And I'm like, well, well, shit, I didn't even see like one of the first agents. I'm like, I didn't even see the ad like until I got it. The an hour before I had to go send it off to the media outlet. And had I been a part of that conversation, I could have told you that that message is never going to resonate with that audience. Right. And that or that message is never going to create impact on that media outlet. So, you know, it's the media message.
06:38 SPEAKER_02 And sometimes it's the opposite, like with mid to small level clients. A lot of times their expectations are what are what's kind of off.
06:46 SPEAKER_01 That's right. Or I have fifty dollars a day or I have a thousand dollar budget. I should see 10 X return. Right. That money. And so, yeah, but that was so, you know, I became more more vocal in how do I make sure that I am figuring out which outlet is the best, which, you know, have my science down. And then it became once it got easier as the the media planning kind of all with all the tools, then it became, well, yeah, we saw results and you and I can, you know, we have some some past clients that, you know, we can attest to this. But why saw I saw a rise in sales or I saw but some seats or I saw return. But tell me where that return came from. So the attributable of and it's like, well, do you give you made money? Like, does it really matter? No, no, I need to know for for future planning. So, you know, it's whether it should be last click attribution. Or like because I mean, they click for like seven days or 30 days after. And what is that? You know, what is that attributable, you know, window? So, I mean, there's so much science around media planning. And and you're right. Like you said, you know, you and I get those same questions coming downstream from clients and or me coming to you going, Oh, my gosh, is this going to you know, do we have enough science to know that we're going to see a return? Are we going to hit benchmark? Are we going to go above benchmark?
08:30 SPEAKER_02 And that really is like that, I would say, is the more impetus like behind like the actual starting of the company and everything else is that there is like a landing page should convert between three to five percent. Like that's a hard number.
08:42 SPEAKER_01 Like it's you know, there's enough data out there. Exactly. We have said, if you're in this industry in this category, this is where this is what a landing page should do. This is what a banner ad should do.
08:56 SPEAKER_02 And you have all that. Yeah, exactly. And so it really was not it really. You know, finding all that information and just bringing it all into one place, it kind of blew my mind that like it didn't already exist. But there really was no sort of single place where you could go and sort of do your planning with the return on ad spend and those types of things, sort of the end in mind. It was there was all these tools where like you could calculate like, OK, you can get approximately this many clicks or something like that. But then there was nothing that really brought everything together. And so, right.
09:32 SPEAKER_01 Because so did did what is it? The DMA does it? Did they not have all of those? Because I know you guys went way deep into all the the benchmarks. But I was surprised that there wasn't like one industry that was or association for the media, you know, for for the media category.
09:57 SPEAKER_02 Yeah. Well, what's funny is that there are so many like that. So there was the the information kind of lived in two buckets, like either it would be like you're looking at using like radio, for example. If you're looking at radio stats that are based on numbers from the RAB, the radio advertising, it's like, well, how accurate is that information? Because it's you're leaning on numbers and stats from like that own industry. That's right. Right. And so like there was those types of numbers where it's like, is that actually true information or the other end of the spectrum? Like you were looking at competitive information. In other words, you'd be looking at like, what is the, you know, the out of home association say about like what a radio campaign should be, which is almost skewed the opposite direction.
10:45 SPEAKER_01 Right. The TV and, you know, and the whole digital spaces of like you've got different the programmatic tools all have these different, you know. Stats. Exactly. It's like, which one do you trust?
11:01 SPEAKER_02 Exactly. And so but there, you know, so it was really about mixing sort of those things together, combining sources and then bringing it all into one place so that you're able to say, OK, if I'm and then also to just in real time, I mean, just some basic arithmetic of like, OK, if I put in a Facebook campaign to this at the average Facebook cost per click, what is that likely to convert at? Because we know Facebook's going to convert it like more like three percent as opposed to, you know, nine percent or whatever. Right. But, you know, so just knowing all of that and so just building that out. But then also to that was how it started. Yeah, that's it.
11:41 SPEAKER_01 That's it. That's it. You were just like you're like, there's got to be a need. If that was something you wanted and you saw the the endless questions over 20 years.
11:51 SPEAKER_02 Yeah, exactly. The same four or five questions being just asked repeatedly for 20 years. Right. Right. It's you're right. It is the same ones over and over again. Right. Where I'm like, I can't be the only one that's like that's that has no answer to this. And so so, yeah, that was that was the starting idea was OK, was building out the building out exactly that platform so that you can say with like just like a financial plan or would give me X amount of dollars.
12:20 SPEAKER_01 You should expect this kind of return. OK. So more of a predictive benchmarking kind of tool. Is that OK? And so when you left, that was like, OK, this is the this is the the problem. I'm solving. And then. Were you the one that was building it? Did you have to find a team like what was that that whole like creation of the company?
12:43 SPEAKER_02 Yeah, so I had to find so found the team. You know, I got like very basic coding knowledge, but like not not enough to like build something that's like workable and usable. So, yeah, I know that was the first step was building a team. And I will say that was the thing that like because I'd managed teams before, right? So I had several. You had a lot of. And, you know, I was thinking, well, I've managed teams. I've even met, you know, and even was over the the PNL of my department and the profit and loss of my department. So I was like, I would have guessed if you'd asked me like, what's different when it's your own company, like versus the other. I've been like, nothing. It's building a team and managing profit and loss. But I was wrong. Like there was still like even with that experience, like it was quite a learning curve, like building your own team is, is, you know, you realize, oh, wait, I can't recruit with the same power that I had before. You know, and you know, and those types of things, it's like things that I wasn't expecting to be different.
13:42 SPEAKER_01 Did you start the company under like under with your own investment or did you take this idea like a I'm a caught up paper napkin idea to investors? Because I know you have like a board and all and all that. But how was that? How did that process work?
14:01 SPEAKER_02 If the adults started originally with me, I mean, we had a working prototype, like based off of my napkin and my own like my own finances. I mean, we went off, we went overseas for like the coding and stuff. And thankfully, I had enough to like build like frameworks. Yeah. Like I kind of wanted to do this. And then so mostly it was having in the early days was having to outsource just to make things look better. Right.
14:22 SPEAKER_01 Make the user experience better and stuff. You were more the architect.
14:26 SPEAKER_02 Exactly. The designer. Yeah. For this spent time. I keep in mind that even though like the reason we had such success like at launch, it's because it was kind of a company that I was like sort of building nights and weekends for like five years. Right. OK. What I was doing instead of playing golf was like working on this.
14:45 SPEAKER_01 You're like, this is I've got to find this. Yeah. The solution to that. So how did you so when you got an investor, was it more of your prototype was done and the coding was done and you're like, OK, for me to really like make this an actual company and make, you know, to go to the next level, I need X investment.
15:06 SPEAKER_02 Or what was that? Yeah, no, that's exactly right. At that point, we had more or less the basics of what would be a company. I just needed, you know, we just needed to build out the team
15:17 SPEAKER_01 and be able to devote the time to it. Is that what the investment went to was was more labor? Yeah. And staff. OK. Exactly. And then and so this has been two, two years since you launched.
15:33 SPEAKER_02 Yeah, we're in our second year. Yeah, we launched in February of
15:39 SPEAKER_01 February of last year was our official launch. OK. Whoa. Yeah. Come a long way. Yeah. And so and your name. So describe the name and because there's there's a
15:53 SPEAKER_02 it's an abbreviation. So well, and our name is sort of has morphed, which kind of follows the change of the company as a whole. Like at first, we were all focused in on this tool that we built this we call dynamic response, advertisement, forecasting technology or draft technology. And because our whole idea was like, oh, well, we've built this cool thing. We'll just go out there and sell this thing as a as a SaaS, as a software service. And that was that was the original idea. So like the branding was all around that. The messaging was all around that. But then we realized, wait a second, we're trying to sell stuff to one of the most cash strapped industries like ever, like ad agencies, PR companies, those types of things run on fairly thin, thinish margins and also don't have like you just don't have like a ton of a lot of times there's float, right? Like you get the invoice before your clients paid for it. Yeah, and those like 90 days.
16:53 SPEAKER_01 Yeah, right. So 90, 120 days float.
16:56 SPEAKER_02 Not that you can relate to any of that or anything. Yeah, exactly. But yeah, so in other words, we're trying to sell like to an industry that was like, no, I don't have money for this.
17:08 SPEAKER_01 But but even if I mean, there are a lot of these agencies, they're already investing in the the Nielsen date, you know, the books. They're investing in media. I mean, those media tools, I mean, like Smart Plus and all that. Those are like 20 grand, sometimes 50 grand a year. And then you look at the data between Scarborough, MRI and the Nielsen data and then the digital data. I mean, sometimes agencies are spending six figures plus on just managing media. Yeah, exactly. So they know there's no guesses, right? So but I'm like, you know, so it makes sense of to go after, you know, those agencies, because it's you're bringing one more tool to take the guesswork out. And ultimately, they could you could lose the other data. Yeah, if you wanted to.
18:00 SPEAKER_02 I mean, we're paying for it, too. So like, you know, there's no reason for for sort of double payment and all that stuff. But so, yeah, that was that was and that was sort of the biggest that was one of the biggest changes is our name.
18:15 SPEAKER_01 Your pivot. OK.
18:17 SPEAKER_02 From focusing in on just licensing that technology as a piece, because we had so many requests for. Well, can you guys just like do that? So in other words, we would we were selling this thing that allows just for the for listeners sake. Our tool basically allows you to be able to plug in. I've got 10 grand a month in budget. What kind of response?
18:40 SPEAKER_01 How many leads can I expect to generate? How many conversions I can get if I place on Facebook versus if I do an out of home or if I do? I mean, it's because it's both traditional and correct digital.
18:54 SPEAKER_02 And so that was the original idea. But then we got in so many like situations where the where we had someone be like,
19:01 SPEAKER_01 can you guys just do this? You built a great plan now, just execute it.
19:08 SPEAKER_02 Exactly. And so that was that was that was a big pivot for us was realizing like, oh, that's actually like a much bigger opportunity. And it's the same team. Like I'd already pulled away. Like I already had sort of built like, you know, David and Nina and like some folks that are great at managing campaigns. I think so that they could analyze campaigns and planning and all that stuff. And these and then I was like, wait, we could just have them executed. So, I mean, that was it was an ended up being an easy and somewhat obvious pivot like afterwards, but was just it's only obvious after something happens. Right.
19:43 SPEAKER_01 Right. Yeah. I mean, so what? So you you started the company last February, so you're in year two. When did you realize the pivot? Was it like six months in or was it just like a few months ago?
19:55 SPEAKER_02 No, it was it was August of last August issue.
19:58 SPEAKER_01 OK. And then I know another category that you guys were talking about going after, too, was like the media companies, you know, the radio, the TV, the, you know, because they're all selling everything. You know, you go to a radio station, they'll sell you outdoor. Yeah, they'll sell you digital.
20:18 SPEAKER_02 They'll sell you Facebook. Exactly. I mean, we're living in a world of like consult, like consolidate, like partner consolidation and all of that. Exactly. So rather than having 20 different partners, like, you know, so if you are a billboard company and you've got five or six different places you're buying stuff from, you know, you've got your PPC vendor and you've got your like programmatic vendor and you've got your, you know,
20:44 SPEAKER_01 over the top television provider like. That's right. I mean, we as an agency, we deal with hundreds and hundreds of media, you know, media companies analyzing and scrutinizing, you know, their offering. So, yeah, I can see where it's a you could be a white label source for those media companies. Correct.
21:06 SPEAKER_02 And even places, even other industries entirely, like we have we've had we've had we have a point of sales company that was just doing point of sales for and they're already in businesses, right, all the time. And they're like, well, we could just start offering the marketing and advertising piece of it. So it's like it's it's kind of a world where like if they were trying to do it themselves, that'd be, I think, a terrible idea. I think. But I think that's the world we're moving towards is like, eventually, it's like if you're going to go order pins from a place, right. And they'll be like, hey, and we can also do your like television buy.
21:44 SPEAKER_01 Right, right. So so you guys did this pivot in and now it's like, OK, how do we it did you have to repitch to your investors or know anything like that, like any any pressure points in that pivot?
22:03 SPEAKER_02 Yeah, I mean, the biggest pressure point was just it was more operationally. Thankfully, like there's nobody that's invested in us that doesn't have equity. So like there's nobody that's like just cares about like the cash. Right. Yeah. They're not just looking at skip going right. Skip. Yeah, exactly. Get it together, man. Right. And so, yeah, so thankfully, if it's good for the company, it's good for everybody. Right. Right. That was and it makes sense. I mean, it's also easier on the pitch side to like, right. Instead of like, you know, we still have this the software as a service. And so something that someone can buy. Right. But it's like, hey, instead of paying this upfront, we'll just give you this for free. And if you sell something, if you use it to make money, then it costs you something. Right. Does it cost you anything? So it's easier on the pitch. It was it was cleaner. So I know the biggest frustration was more like internally, making sure that we were set up to actually execute all that stuff. And then it required us building out other things that didn't exist, like the dashboards and those things that we now have in place where we're able to monitor because originally it was all built like just to predict campaigns. Right. Right. Now it's like now you got to track the performance. Exactly. And so building all of those processes out was just added stuff. But that process also went, you know, is now done, thankfully. So done ish. I mean, I was never done.
23:34 SPEAKER_01 You know, it's always a tweet.
23:38 SPEAKER_02 You and I met yesterday and you know, you asked a question about how asking how like tracking because we listen to phone calls or we track phone calls when someone calls in, you're you're asking, well, like, can you give any feedback on that? It's like, well, yeah. So like we keep it sort of extending where our like involvement is, because now we're looking at adding on a tool that will even take like notes of phone calls coming in. So we can say like, you know, hey, your phone people suck. Right. So it's like, right. Only does your display it, you know, so we can show, you know, are you getting the response from the ads you should be getting? Are you getting the response from the page you're getting? And now, like once they call in, are your salespeople doing the right thing?
24:19 SPEAKER_01 Like, exactly. And, you know, putting my hat on is like the, the fractional CMO running Brightco. I mean, that's one of the, the, the things that we get tasked with our clients the most. That's why I was excited to hear, you know, the evolution, because it's not, it's nowadays, not just how did this ad campaign perform of return on ad spend, but we get challenged from a, from Brightco team perspective of, well, did it convert? And we're like, well, what is your definition of conversion? Is it lead for it? Cause like, hey, if it goes over to a sales team and we're not looped in, I can't, you know, I don't control your sales strategy. I'm not over your sales team. We don't manage your sales enablement program to coach people. But we get blamed when stuff doesn't close or, or if there's churn. So it's not just, you know, the, they closed something and they got that, that first little trial, but then people bounce. And a lot of our, you know, the loyalty is not there. And so, you know, we try to look at from marketing from Brightco again, wearing that hat, that holistic kind of closed loop. Yeah. 360 view. I know a lot of agencies don't do that. But also a lot of media companies don't offer that viewpoint of, look, we can do the best ad campaign out there, but if you have a terrible sales team, but the fact that your tool, which I think is just incredible, the evolution of that is then you can monitor that, hand that over to whoever the sales officer is and goes, okay, I'm giving you all the ammunition.
26:13 SPEAKER_02 Correct. Exactly. And it's just, it protects it. It not only protects all sides, like it keeps every, it keeps the sales department from being like, Oh, marketing sucks. Right.
26:21 SPEAKER_01 I didn't get any leads or those leads sucked, you know,
26:25 SPEAKER_02 and it protects them. You know, and it also will highlight if there is a problem and maybe the marketing does, you know, maybe you are getting the wrong kinds of leads or whatever. Like, and so it's just, it makes everything like more objective, which is kind of like, that's my Jan. That's like what I'm all about. As I make it more like getting things closer to like, what's actually going on because if it is the audience that's an issue, well then let's switch up the audience. You know, finding that out as early as possible in the process.
26:52 SPEAKER_01 Like it just saves time and money. And we always say like, even when we're trying to talk to the sales team and like, Hey, if, if these message points aren't resonating, yeah, then that's, we need to go back to the drawing board and look at what are those, you know, those benefits, those attributes that we might need to test further. Right. Because then the story, you know, we need to rescript the stories, but if it's just bad sales techniques, well, that's again,
27:22 SPEAKER_02 that's another, you know, we had a partner, we had an agency, we were working with where they were like, where they had a client that was basically saying they weren't getting anything from the leads. And because we do track phone calls and stuff, you go in and you look and you can see that, well, the phone wasn't being answered. So it's like, well, that's, you know, and it's, again, it's a very objective thing of like, well, I mean, it's hard when you're not answering the phone calls to like, to get, just being able to provide that data, because then the business owner was surprised to learn that, you know, Hey, this is the Crown Office people aren't answering the phone.
27:54 SPEAKER_01 That's right. So, cause that's what I'll see, I'll see CEOs or CMOs. That's all they want is am I generating the sales? Am I getting better share of wallet or I'm increasing my margins? How do I improve on those, you know, those three points? So are you going to shift? So your name right now is draft ad technologies. Are you guys going to keep the name? Yeah. You're still new in the process or are you guys going to do another pivot?
28:22 SPEAKER_02 I don't think we're going to change the name draft advertising technologies. It's just what we might drop is like the dots.
28:29 SPEAKER_01 Cause right now our logo is D dot R dot A. Okay. We may just drop the acronym. If anything changes, it'll be the acronym. Well, you make up a new one.
28:40 SPEAKER_02 Yeah, right. Exactly. That's what we should do actually, is so that we don't even change the dots. You just figure out like new things.
28:47 SPEAKER_01 So, okay. So you're a new founder. What has been your biggest kind of like aha moments in this journey?
28:58 SPEAKER_02 Yeah. Well, I mean, one of the, I mean, figuring out that, oh wait, we're selling something that nobody really wants. I would say like, was the first like, oh my goodness, we need to change. Right. And then figuring out, like it was always, it's like the ultimate nice to have not the not need to have. And so that pivot of that changing from being like, oh actually what people want really is like an easy button. And, um, I would say that is the biggest, that's the biggest aha moment is like, wait, people don't want it. Something, you know, it's like, yeah, a nice, I'll just make up an exam, like a nice lawnmower might make it easier for me to cut my grass. But really what I want is to not even have to think about grass. Right. Right. And I think that's, you know, is much of that that you can take off of your customer's plate, like whoever it is, like, I think that's the biggest aha moment is like, um, you know, if you're still a nice to have, maybe you're just not taking enough things off people's plates.
29:56 SPEAKER_01 So it's that, it's that value creation. Yeah. Right. Um, what, so what's been the biggest, oh shit, like your biggest, holy crap, what have I done moment?
30:08 SPEAKER_02 Well, there have been some literal answers to that. Like, like one month where I like, I had a, I had a very hard time letting go of like, of things, like do it, being in the weeds. Yes, exactly. And, uh, which is bad because as of, you know, like it, usually if you're good at certain, at like leading teams and founding and stuff, you kind of suck at the, at the details stuff. So like went literally a month where I like forgot to invoice anybody. Um, so which is an issue. So I would say that those are, that's like one of the biggest like moments, but then like I said, the biggest, the biggest overall, like more meta, like a shit moment was just realizing that, oh, our whole company is like based on a premise that I don't think anyone's willing to pay for. So let's, let's change that.
30:56 SPEAKER_01 Oh, I think I'm hitting my light back here and it's like flexing. It's like, all of a sudden we'll get, I don't think you're seeing it, but it's like this little light like does a little spark. Um, so skit. So what's, so what's next for you? Like if you look at, I mean, what was your milestone? You told me after a year, you guys hit what milestone?
31:20 SPEAKER_02 Yeah, we cross, we crossed the one, we crossed the 1 million mark. Um, our goals, I mean, our, our sort of stretch goal, I'm not, you know, the goal I would like to really hit is 5 million. Um,
31:31 SPEAKER_01 within like into this year or, okay.
31:34 SPEAKER_02 So, um, I'm not, we're not, that's different than our projection number. That's our more like if everything goes well number, but, um, that's the number I'm trying for him. That's the one I've got on my little board over here. That's the aspirational. Right. Exactly. It's the, it's your BHAG, right? Your big audacious. Exactly. And, um, so, you know, that's, but even, but even on a conservative projection, I mean, we'll be up, you know, close to two. I mean, even if like, unless just we have another oh shit moment, right? I forget. Yeah. I don't handle my own business stuff anymore.
32:08 SPEAKER_01 Is that, is that where you had to like hire people to balance out your strengths?
32:13 SPEAKER_02 Yeah. Well, and what's, what's, what's truly tragic about that is I'd already done that, right? Like I already had the team in place. I just wasn't using them. So that's, having a great team is one thing, but then not allowing them to do things is, yeah, another, another piece of that.
32:29 SPEAKER_01 So you and I talked about this, uh, a little bit of the difference in when you leave a company, you know, a brand that you could promote, you're a part of you, you feel that culture and you feel a part of it to then now be responsible for creating a brand, creating a culture, recruiting a team, managing a team, leading a team. What's been that shift in mindset? Um, you know, hasn't been a shift in mindset for you. Were you like walked into this and went, got it?
33:08 SPEAKER_02 Yeah, no, it was a total, it was, I would say I went through a very, like I said, I almost went in sort of with a naivety of like, I've managed teams. I built, you know, I built my own department. I managed teams. I handled P and L. That's all there is to running a business. All I gotta do is do that again, right? Build a new team, build new processes, manage profit loss. I would have said I had all of it done. Like, but you realize that, what was the difference? The big, the difference is that is the, um, is not how is being is doing all of that without having, um, like you said, culture and things like company culture and like having your own brand. I would have said, didn't matter at all. Like anytime I would hear things, like, Oh, you gotta have a good corporate culture, company culture. I would almost sort of eye roll at those things. And I'd be like, yeah, but then when you lose it, you realize, Oh wait, that actually does matter a whole lot. Like that's it. Now I've got to build that or like, we're just gonna be a company of assholes. Right. You know, and that's like realizing, um, realizing how much, you know, how much, how, how easy it is to go off the rails if you don't set parameters upfront, like parameters of like, Hey, it's okay to, um, because if you think like corporate politics and those types of things are bad, like in a company, which they are in large companies, right? Yeah. But it's even, I would almost say it's even worse when you don't have it with in small companies because they don't have the guard rails and print. Right. And so there's even more like chaos. Yeah. Right. Exactly. And so you know, putting all of those things and then just, you know, realizing like how little I know about like anything, I would say that that's the biggest.
34:54 SPEAKER_01 What are you talking about? What do you mean you don't know? A little bit.
34:59 SPEAKER_02 Just every now, like for example, I mean, even things, dumb things, like I remember, um, I remember being a four weeks in ish, um, and I bought a printer and I literally spent like, and this is like a really embarrassing story. I probably should have.
35:17 SPEAKER_01 I can probably share a thousand of these.
35:19 SPEAKER_02 But I remember like installing this printer and it took me like four freaking hours to get this, like the, this printer done. Um, which is normally I would have, it would have just been a phone call to it. Right. Like, right. So like, but instead I've spent like four freaking hours putting in this. I literally almost started crying. I may have even started crying. Like is it just like, I can't do this is dumb. I don't have anybody in place. You know, you have those moments as like breakdown, I guess,
35:48 SPEAKER_01 that just you're not expecting. Like what have I, what have I thought? What have I done?
35:51 SPEAKER_02 Yeah, exactly. I can't build this. I can't even install this stupid printer without it taking a freaking half a day.
35:57 SPEAKER_01 Do you feel, so do you ever get, I know I felt it, the imposter syndrome and I still feel it. I'm nine years into being a founder. Um, and, and, and shifting, you know, from Brightco, but then even when I started orange web last year, like it, it magnified my, my ignorance, or just my naivety and self-confidence. I mean, it just,
36:25 SPEAKER_02 yeah. Yeah. Well, it's like a constant roller coaster, right? Of like being like, okay, finally I got this. And then you'll start something new. And it's like, well, nevermind. And yeah, I think being uncomfortable with like just not knowing the answers to things. And then also, you know, like, yeah, I get imposter syndrome a ton. And I will say one of the biggest challenges for me is like, I'm big on like making like self-deprecating jokes and those types of things. I think that that's a good thing. And I think in a lot of ways, chances it is, but like I realized how damaging that can be though. Like when I'm, when you're the leader of a company and I'll, and I, I remember I said a joke, the, um, this was not even four months ago. So fairly recently, I was like jokingly like, and of course, you know, we might go out of business tomorrow. That time. Yeah. I was like, and I mean it as a joke. I mean, we're not, some ship like would really have to go wrong for that to be the case, right? Like there would be like, it would be zombie apocalypse level for that to happen. Right. But like, um, making that kind of joke when you're the leader of a team is not a good idea. So like, because then, because like there, you know, they got their own stuff to worry about. Like, and then now you've, now the leader of the company has just been like, yeah,
37:39 SPEAKER_01 of course we might go out of business tomorrow. Ha ha ha. Right. Right. I know. But they don't know. Um, is that been, is that been the hardest thing is around like the, the culture and like building a team or has it been in other areas?
37:56 SPEAKER_02 I wouldn't say that's the hardest overall thing. I think that was the hardest thing that I wasn't used to at all. That was like the hardest thing that I just had no experience with whatsoever. Cause when you're, you're working for a large corporation and you're just over a part of it and you make a joke like that, everyone laughs. Right. Right. Um, but I would say that was the biggest difference, but no, I the hardest thing in general is just the, the stuff that everyone sort of talks about it that you know, it's going to be hard. Like the, the, the getting up and going and putting in a full, you know, long week when no one knows whether you did a long week or not, or, or putting in a long week when you, um, I don't know, when you're always balancing that, that roller coaster of, Oh no, we don't have enough business with, Oh no, we just got these several big orders and now we've got too much business. You know, it's like, it seems like it's one, you're going from one fire to the other. That is truly the hardest thing is just the like, like sisyphatic, like roller coaster that it is, but it's also like what makes it awesome too. I mean, that's, that's also the fun part of it. So.
39:05 SPEAKER_01 It's that it's that bounce, that bouncing back and forth. So is there anything that you're putting in place for the company or for yourself that's like helping to manage that balance or creating the balance to minimize the chaos, welcoming the chaos or.
39:27 SPEAKER_02 Yeah. Operationally putting in a ton of, basically we've made as many things as audit is automated as possible. And then, and we now have like true like communication practices and like, um, and man in workflows and you know, we've got all of our, we're all on the same task managers and just things like that. Um, yeah. Operationally making sure that's all set up. Then on the personal side, making, like taking, making sure that while here I'll use, I'll share my little, I've got my own little like planner that I have every day where it not only tracks like my appointments and those types of things, but also to making sure that I'm getting the right sleep, making sure I'm taking the right events.
40:11 SPEAKER_01 Is that full focus?
40:12 SPEAKER_02 It's no, but it's probably the same thing. This is the unstoppable journal. Uh huh. Probably the same thing as full focus. It's a different flavor.
40:23 SPEAKER_01 I'm an adopted full focus. I've not heard of the unstoppable journal. Do you like it?
40:27 SPEAKER_02 I do. Yeah. I like it a lot because it was, it makes a huge difference. A dumb example, um, is, is, uh, you know, things like making sure that I'm not like that I'm not, you know, sleeping, you know, that if, if I get up at like, if I stay awake till like one or two AM working on something, I kill my productivity for like the next couple of days and just, you know, and that's, it doesn't matter as much if you're just writing the clock, right? Right. But when you're steering the ship, like that's a huge deal. So, things that I never paid attention to, um, I'm now starting to, so, I mean, I'd say that helps a lot. Making sure that I'm going to the gym and those types of things. I mean, I'm, still, I'm obviously early on that journey still, but, um,
41:13 SPEAKER_01 aren't we all? I was telling, so I started these seven minutes wall Pilates. Uh, I have, I started that earlier this year. That was like my junior. That was my 2023 resolution of like, okay, I'm going to do these daily seven minutes. I can get through that. That's like two songs, you know, right. For my, for my era of songs, not these, you know, I mean, or it's like one day Matthew's, you know,
41:43 SPEAKER_02 or a third of a fish song.
41:45 SPEAKER_01 Yeah. It's one who song. Right. I was like, but I can't, I have not made, I have not made it past like three minutes. That's how sad I'm so early in my journey. I'm like, used to be in such good shape, but I, I did not get that discipline early enough in my entrepreneurial journey that, I'm trying, I'm trying to do better, but yeah, I'm at like three minutes.
42:10 SPEAKER_02 That's solid. That's a whole,
42:13 SPEAKER_01 and then I'm out of breath and I was like, if I can just get, so now Michael, just get through another song, just get through or one, one song, one song. So what keeps you at, you talk about sleep. What keeps you up at night?
42:29 SPEAKER_02 Well, I mean the literally answer to that. I mean, if you mean that in terms of what I'm worried, then that's a different answer. But like the things that literally keep me awake at night are usually when I'm working on something like I get like this past weekend, I was working on this AI tool that we're at, that we've added to our social media thing. That's the kind of stuff that I actually stay awake doing.
42:48 SPEAKER_01 You're in the weeds. You are building.
42:51 SPEAKER_02 That's often when I'm working on a campaign or when I'm doing those types of things. But I mean, in terms of the things that worry me, you know, you just, you never know like what worries me is the constant state of like what, whatever could be like, whatever could happen like next month that I just don't see happening. I would say that's the, I would say.
43:13 SPEAKER_01 You don't know what you don't know. Yeah, right. And that is kind of scary.
43:17 SPEAKER_02 Exactly. And yeah, you get, you get in these like situations where you're like, Oh, I didn't, I didn't know what that was. We had a, I got asked, you know, we, we had just signed a big partner. We just signed this partnership and I got asked, Hey, can you send us your liability insurance information?
43:37 SPEAKER_01 You're like what? Yeah. Yeah. Like you haven't described like what that is. Like, and then you're like, I need to call my insurance carrier.
43:50 SPEAKER_02 I'm like, Oh yeah, absolutely. Dial. Exactly. And so, yeah, just little things like that. You just never, I would say that's, that's the thing. Those are the things that, that worry me. I would say the most is just, you never know.
44:04 SPEAKER_01 Where do you tap? Like, where do you go for inspiration? And, and resources and like, we're, you know,
44:12 SPEAKER_02 So I'm a, I'm an avid, I mean, I literally listen to, um, I'm, I'm, I'm dyslexic. I actually have like a hard time reading. Um, like I, like literally, um, the, I'm almost illiterate, like the, uh, in terms of, uh, I don't know if you have, like, no one's ever noticed, you know, no one ever noticed it, but a lot of times I'll at a restaurant and be like, Hey, what do you guys have? And stuff. It's because I have a hard time reading, but like literally, um, but he, um, uh, but I actually listened to about seven plus books, almost a book a day.
44:46 SPEAKER_01 Well, I listened to you and business or are these like fun? Are there most of business?
44:51 SPEAKER_02 Mostly, although I will say I read a lot of spiritual books too. I, you know, I'm a, I'm a, I'm a Christian and I, and so a lot of it does steer that way too. But most of what I'm listening to is, is business books because it's kind of follows like the trends in my life. Like I was, you know, power housing through parenting books. One of my kids were, you know, I was having kids, I went through like a period of time there where I was having a kid a year basically. And, um, and those times, so it kind of matches whatever period of life I'm in, but right now it's, it's almost all, it's, it's almost all business books. And I, I, there are some great business books out there.
45:30 SPEAKER_01 What's your favorite? What's, what's been your favorite,
45:32 SPEAKER_02 like two or three books? The, the books that I would say have had the biggest impact on me, like, like literal impact. Um, the, uh, there's a book called profit first, which is, I would say a biggest accounting book. It doesn't, the book, the title is very misleading. It's actually not about like being an asshole, right? Like it's not, but it's about making sure that, you know, you get paid. Correct. Exactly. Which is kind of a big deal. It's the book that I see so many businesses. I actually had a friend of mine that was talking, it was going over, he was considering buying a franchise and he was having me look at the books and I was like, I don't think you're ever going to actually make money from this. And that's the ability to know those types of things like, so profit first I'd say is a good one to read, especially if someone hasn't had like a true business accounting experience, like, um, then, uh, I would say that's a good one. The, the, I would actually recommend not, this is the unstoppable journal, but the book unstoppable is actually a really good book. Um, it does a good job of mixing health and business advice.
46:47 SPEAKER_01 Okay. So, so like physical health or like mental health or
46:52 SPEAKER_02 both. Yeah. Okay. Because to be unstoppable, uh, you have to have all of those things. That's right. That's, um, cause if he, you know, you can't be unstoppable. And then like, uh, because even things like, you know, I mean, early on, I think I had, uh, last, last year, I got strep throat, right? Which not a big deal, right? Like, it's not, not like threatening at all or anything, but, but losing a week of productivity because of something like that. Yeah. Yeah, exactly. When you, especially, you know, in the early days. So, um, so that, that book, um, bias towards that one is I literally just finished it. Exactly. Um, but then also too, uh, I would say anything by, by Donald Miller, like the, his, the story brand guy, um, his, uh, his book, uh, flight plan, pretty sure it's called flight plan. I think the book is called flight plan. If you'll find it, if you Google flight plans, I know that's the PDF that you can get as I like, as a download is the flight, is this flight plan test, but basically thinking of a business as a plane was a really good part way to, um, think through making sure that you've got the cockpit and the engines and the engines sales and marketing equal sides of the same of the plane, you know, making sure that, you know, the, the center, the main part of it's your operational operations, keeping that as lean as possible. Um, cause the bigger that is, the more fuel it takes, the more sales and marketing has to work and all that. The other side, but that's, that's a really good book too. Um, those are the ones that I think found the most. I mean, there's, there's so many, Navarravakan has the, his almanacs really good. There's so many good ones, but those are the ones that like, I would say structurally framed like the way we built the business.
48:47 SPEAKER_01 Okay. Those are good. I've, I have not read flight plan, but I, um, I'm gonna go check that one out. That sounds great. Yeah. Well, what motivates you to get you out of bed in the morning?
48:59 SPEAKER_02 I'd say so two things, my, you know, obviously there's like my obligation to my family, right? Right. But not a great provider, right? If I'm, if I'm not, if I'm not taking care of them, but also too, I mean, I genuinely wanting to make an impact in the world. Like the, the, the entrepreneurs and things that I've found most inspiring are, um, like the Milton Hershey and Walt Disney and these people that actually built not just, um, companies, but I mean, like they literally changed their lives for both employees and customers. That's the kind of impact or legacy that, um, that I think we should all be striving. You know, I think everyone's trying to make as large an impact in this world as they can to, you know, good impact and impact for good. Right. I think that that genuinely motivates me a lot thinking through like, who can I help today? You know, there's nothing worse that I see than like when I see like, uh, when I see like a, you know, a campaign, um, and I'm like, well, I know that's not generating a return. How can I help them? Right. Exactly. Like that. It's, it's heartbreaking to see those things.
50:11 SPEAKER_01 I mean, we see, yeah, it's a bad marketing and bad. It's like, it's painful. It like hits you in the chest of, Oh my gosh, you know, we can do so much better. You know, so you want to be inspirational. What are, what are three things that you, uh, would tell other founders or entrepreneurs advice that you would give them?
50:34 SPEAKER_02 Yeah. The biggest piece of advice I would say would be to be super empathetic, like constantly listening to feedback from customers and, and employees. So like your staff and customers soliciting advice, if someone, you know, I would say that there's, if you've got that angry or combatant client or customer or somebody, that's actually somebody you can learn a lot from because yes, they might be an asshole, but they also might be an asshole with really good advice that nobody else is telling you. And so always listening for those things, um, both internally and externally, like what should I be, what should I change? You know, like what should, what should be different? Um, I think that's the key to business success. And I think that's also the key. I mean, I think that also helps in life too, like just always being willing to listen to you, other perspectives and willing to put yourself in, um, and then being loving and kind, like in respecting, like there's no, um, there might be crazy people, but there's no crazy person, right? Right. Walk in their shoes. Exactly. Yeah. And so, so radical empathy I'd say is, it would be sort of rule number one. Um, beyond that being disciplined, um, you know, discipline the root word that, you know, disciple, um, means to teach. So discipline is teaching yourself, right? Like being constantly disciplined, working on yourself, making yourself better. I always have a list of things. I had literally keep a list of things that I want to change about myself. And so always looking for self-improvement. Um, you know, the, um, which I kind of goes with the, I mean, I guess one sort of leads to the other, right? Like I'm, you want to be empathetic so that you can learn what needs to change and then being disciplined to work and change on those things. Right. Um, and or to continue with what's going well, cause there's plenty of times where you're like, things are going well. I'm bored now. Let me do other stuff. Right. Right. And that's when things fall apart. I would actually, you know, to change an answer to what I'm worried about that, I would say is the, the worry part of it is like when things are going well, you almost start to worry like, well, are we going to stop doing the fundamentals or those types of things? Um, being disciplined to not do that. Right. Right. Right. Keep what's going with what's doing well. Exactly. Right. And third piece of advice, I don't know, look, try to make an impact and do good things in this world. I'd say that's,
53:03 SPEAKER_01 that's it. Yeah. I love it. You can change the world right from here, right from your seat. Um, now before we go and I were, I know we're, we're, we're wrapping up here. Uh, I do have one, one other question. This might be an off a really off topic because we're media nerds and with all the craziness that's happening in the, are you following the WGA strike at all and how AI is impacting and that's going to lead into second, you know, sag and I EPSA and all those other associations. Are you following any of that? Yes, very much so. So we might have to do a side, another podcast, just on that subject, because I want somebody to talk to about it. Cause I, I have another, I'm on Tumblr anonymously, and I'm not going to give out my, I'm not going to dox myself there, but, uh, but yeah, I, I write a lot about the just the media industry and how it's changing and where streaming is going and the big players and how the strikes affecting and just, you know, um, and I have no one to talk about it like in real life.
54:18 SPEAKER_02 Yeah. Well, right. That's the kind of thing you bring. It's a good way to lose them.
54:21 SPEAKER_01 I do it in like the hell side of Tumblr where that's where I am.
54:27 SPEAKER_02 You know, I started in advertising cause I was a writer at heart. I still am a writer. I still like, I'm an avid, um, you know, I can't read hardly. Like I'm still a writer. And, um, so I still, I kind of emphasize, empathize more with that's just to give you sort of where I land. Yeah. I'm a writer at heart. I'm still a creative at heart.
54:48 SPEAKER_01 Exactly. Well, and it's just, it's, and I'm, I'm, I'm empathetic on media and like them, you know, um, the content and the productions and, um, but then I can also look at it, go, Ooh, I can see it from a, from a founder and the, you know, the CEO perspire, like they're trying to get as much out of it. But at the same time, it's like, you know, that where AI could take us if they don't block it as scary. Um,
55:17 SPEAKER_02 correct. That's the thing. It's like, it's, I can see, I can definitely see both like as a CEO, like your job, your job is if you do the same job for 10% more efficiency, you should do that same. Right. It's your, especially if you've got shareholders and investors, that's your, I mean, that's your, that's what you do. That's what you're charged with. But at the same time, yeah, it's like, you do want to, I don't know, there almost needs to be safeguards in place. And that's where,
55:42 SPEAKER_01 that's where the unions come in. They're creating the safeguards, protecting, you know, those jobs and, and the content producers. Um, so yeah, um, well, we'll, we'll might have to do another podcast on a, on a different channel or something so I can have somebody to chat with in real life. Yeah, it'll be fun, but we're, but we're out of time, skip. And, and before we go, tell us how people can get ahold of you, how to look for your, you know, draft ed technologies, where do they go?
56:15 SPEAKER_02 Yeah, as well. Draftadvertising.com is, is our, is our site. And as far as, as far as reaching out to me, skip at draftadvertising.com. We'll, we'll get you right to me. And, and yeah, we're happy to, we, we specialize now, like in our pivot, we getting a specific message to a specific group of people to achieve a
56:36 SPEAKER_01 specific result. That's the, that's what we do. Right time, right place, right audience. No guesses. That's right. That's the media mantra. Exactly. Well, thanks for hanging out with me, skip. I enjoyed the conversation always. We'll have to do it again. And thank you. I appreciate it. So for everyone listening or watching us live, thank you for joining us. And this podcast episode will be published this coming Sunday and available on all podcast platforms. So subscribe to Hello Chaos, like, comment and share this great content, help us grow and build a more connected entrepreneurial community. Because skip had a lot of good advice. People need to hear it. Hello Chaos is one of the many resources brought to you by OrangeWIP. OrangeWIP is a multimedia company dedicated to serving founders and entrepreneurs and affiliate cities through hyperlocal online platforms. We are the megaphone for founders telling real, raw and honest stories. OrangeWIP is a one-stop content hub for a founder. It's part storyteller, part how to guide, part navigator with a filterable resource directory for founders, a curated events calendar, and a social media chatter wall. We are currently in three South Carolina markets with our goals to expand to be in 30 cities in five years. If you'd like to be a guest on our podcast, just like skip was, head over to orangewhip.com. Again, that's orange, W I P dot com. Fill out that form on the Hello Chaos page and you'll hear from us. And while you're there, go ahead and subscribe to our weekly whip newsletter. We are ad supported through sponsored native content. Our content is free, accessible and inclusive. And our studio that allows us to produce great content is Bright Marketing. Bright is a full service marketing and advertising agency. That is the content studio for OrangeWIP. Bright was founded in 2013 to support the business community in a better way, solutions and media agnostic, strategic thinkers, sense makers and dot connectors, supporting growth companies across the U S as fractional CMOs and fractional integrated tactical execution teams. If you're interested in becoming a sponsor of OrangeWIP, please email us at hello at orange whip dot com. Y'all thank you for tuning in to Hello Chaos. Again, it's where I have made so ship and I'm your host signing off.