You're not paranoid, security stakes are getting higher

Jeffro (00:01.122)
Welcome back to Digital Dominance. In today’s episode, we’re going to do our best to ignite your entrepreneurial spirit and reshape how you approach your business. Joining me is Kevin Dooley. He’s a serial entrepreneur whose journey from running a hot dog cart to founding multiple successful businesses encapsulates the essence of innovative entrepreneurship. Kevin’s dynamic approach has not only propelled his own companies forward, but he’s also inspired countless others to turn their visions into reality.

So today we’re going to dive into the mindset, strategies and nuances of building a thriving business in our digital age. That’s what it is. So whether you’re a startup founder or a seasoned business leader, Kevin’s insights are designed to help you refine your approach, enhance your messaging and discover new pathways for you to grow. So let’s pay attention. We’re going to explore the art of entrepreneurship with Kevin Dooley. Thanks for being here, Kevin.

Kevin Dooley (00:48.755)
Thank

Thanks for having me, man. Thanks for the great introduction. I appreciate that.

Jeffro (00:55.116)
Yeah, I’m excited. I think we got a lot of cool things to talk about. So first thing, Kevin, you know, there’s a lot of schools of thought out there when it comes to entrepreneurship. Some of the loudest voices talk about the grind, but you’ve turned the concept of rising grind on its head with your mantra of rise and create. So can you talk about that a little bit?

Kevin Dooley (00:58.999)
Yeah.

Kevin Dooley (01:15.539)
Yeah, yeah, absolutely. Love to talk about this. So being a six time founder back, you know, in my generation, I think I’m a little bit older than you, right? But my generation, was always, you know, if you have to work 10 hours a day, do it. If you have to work 12 hours a day, do it. If you have to work 16 hours a day, do it. So I had this mantra and this mindset that whatever it takes, I’m going to push my way through this. My background is as an ice hockey player too. So that kind of fed into this mantra.

And it was always about, let’s, you know, come on everyone, let’s stay till we get the job done. And when I pivoted to what I do now, coaching other founders, I tried to deploy that same mantra and it just didn’t work anymore. And so I to some deep thinking and, know, it’s become because of, you know, digital world, right? A creator’s world. And people are rising and creating every day, creating new ways to reach customers, creating new ways to launch businesses, all that.

So I kind of shifted my mantra from rise and grind to rise and create. And it’s so much more refreshing, you know, man, I wake up every day and it’s like, let me create my, you my day today. What are some neat and cool and new things I’m going to do? And so that’s my approach and it’s been working.

Jeffro (02:30.261)
Nice. Well, I think there’s something to be said for being relentless in your pursuit of those goals, but it doesn’t necessarily mean burn yourself out physically every day. Right?

Kevin Dooley (02:42.163)
100%. I mean, you need desired outcomes, right? Like you can’t get from point A to point B. If you’re at point A now, your point B are your desired outcomes. It’s just a different approach to get there, right? You still need to be, you know, work with intention towards your desired outcomes. But the way in which you do that, right? The methodology, you know, can be a little different. So for me, based on where I am at my point in my life, it’s just become more about the creation than the grinding.

Jeffro (03:10.167)
Well, how do you make someone or help someone make that transition? Because that can be pretty ingrained, right? And if you tell someone, just, you know, be more creative, don’t grind so much like, OK, what does that actually look like?

Kevin Dooley (03:21.969)
Yeah, right. So, I mean, it starts with mindset, right? So any new approach you take, you have to start with your mindset, right? Because the way we’re wired and the way we fire is to repeat, you know, old processes, old patterns and that kind of thing. So it does take a bit of work to break away from this grind mentality to go to creation and hustling, right? So it starts with mindset and then there’s a bunch of tools out there. There’s people that’ll tell you how to

you know, work from the inside out and be in vibrational alignment and manifestation and, you know, meditation and all those great things. To be honest with you, along with my rise and grind, I thought all that stuff was like, woo stuff, right? Like it’s like, no, man, I got the skills and I got the grinding ability. I can make this happen. But really, you know, I started to be more open -minded when I got a little older after six businesses and it’s, it was kind of like,

You know, what are some newer tools where I can advance my mindset, you know? And when I work with founders, there’s no doubt that there’s a bunch of founders out there that have great skillsets, but many of them are stuck, not because they lack skills, but because they lack the mindset to be fast and focused, to take initiative, to take decisive action, you know, to know what they want. You know, a lot of times when I talk to a founder for the first time, it’s like, you know, what do you want from this business? Is this a burning desire or just solving a problem?

And most of them can’t really articulate their desired outcomes. It’s like, well, I want to launch this business and grow it. You know, I want customers and I want revenue. yes, of course. But let’s get more specific about what you really want. And then, you know, then it’s always about mindset. you know, instead of going outside in, right? Like, what is the world telling me I should do? What is the world showing me that I should do? It’s kind of like inside out. Like, what do I really want to do? You know, what do want this business to be? What do want myself to be?

So yeah, for 100%, it takes a shifted mindset to really be able to do this.

Jeffro (05:23.413)
Yeah, so shift in mindset and then break in those habits too, because those are ingrained. they, I’m sure one can hold each other back.

Kevin Dooley (05:29.799)
Yeah, right. For sure, right? Like if you’re used to doing things a certain way, it’s going to be hard to break it. And you know, the Atomic Habits book, which a lot of people read, I think comes into play here and gives you kind of easy step by step ways to break old habits, forge new ones, habits stacking in the morning. I’m a big fan of morning playbooks, right? Like, what do you do to get yourself rolling in the morning? That’s kind of low energy and low brain work, right? So

If you can stack a bunch of good things on top of each other early in the morning, then that really, you know, then you have traction on that day, right? Like we’re all always looking for traction leads to momentum, right? So if you get traction early in the morning and you start the game momentum, then you go into like your first project block or your first meeting or whatever, having already gotten your mindset, you know, in the right space.

Jeffro (06:22.367)
Yeah. And that makes sense. what I have another question. So what about the owners who might say, all right, that’s great. You want me to rise and create? I’m not the creative type. I, I’m the execute type. Like what then?

Kevin Dooley (06:37.181)
Well, I mean, we’re not saying everybody has to be a creative, right? We’re just saying that the world is full of other ways to do things, right? So if your way to do things was always A, because of this creator’s world, there’s like B, C, D, and E. So it’s really about exploring other ways to get to where you want to go. You know, and if your personality, if you’re always been wired as somebody that’s, you know, has got to do things in order, task -related, doers, check -listers, all that kind of stuff.

there’s still room within that to be creative. It’s just changing your approach a little bit and being open -minded as part of that creativity.

Jeffro (07:14.889)
Yeah, and I think as you go through the mindset shifts and figure out these habits, you got to look at your business a little bit differently. Because I think another trap is as owners, we end up working in the business a lot and maybe can’t even picture handing something off to somebody else, right? Like that doesn’t make sense or, you know, so that can be another holdup. But so I guess the question there, you know,

Kevin Dooley (07:39.687)
Yeah, yeah, for sure.

Jeffro (07:42.291)
I’m sorry, but how do we foster that entrepreneurial mindset where we are moving in that direction where we’re more of the owner and not just the doer?

Kevin Dooley (07:52.839)
Yeah, I think it’s looking inside, right? It’s looking inside you, right? Because I think we as humans, there’s two things that we seek, right? We seek satisfaction and joy. And I think there used to be this, I guess, segmentation, like the whole work -life balance. When you’re a founder or you’re a business owner, it’s not work -life balance, really. There’s not a line that you can draw.

It’s really integrated so much, right? So the line is kind of like this, right? Like it’s integrated together. So it’s, it’s like, what makes you happy? What gives you joy, right? And what makes you satisfied? And then, and then being committed to that, right? Because that’s what we really seek as, as humans, right? As individuals and satisfaction and joy. So, you know, if you use that in a lot of companies talk about KPIs, right? Key performance indicators. I talk about KPIs as key personal indicators.

So, you know, if you try something a new way, right, like a lot of being a business owner and an entrepreneur and a founder is about experimentation. So the stuff we’re talking about now, you could experiment with, right, and see if it works for you using those key, you know, personal indicators. So does it give you more or equal satisfaction to the other way you did it? Does it give you, you know, equal or more joy versus the other way you did it? So I think we’re always experimenting as founders and leaders and business owners. So.

It’s all about trying new things, right? And that kind of falls under the umbrella, you know, thing too, where it’s like, you know, try new things, be creative with the way you approach things.

Jeffro (09:32.902)
I like that idea of having the key personal indicators too because one of the pitfalls that business owners have is they don’t track everything, right? They just kind of do stuff and they kind of go by feel or gut instinct like, eh, let’s try something else now, right? But they’re not actually measuring to see what the problem is and maybe they’re fixing the wrong problem, you know? And so that’s so important to know that you actually are moving in the right direction towards those goals and changing those habits and things.

Kevin Dooley (10:01.297)
Yeah. Yeah. Tracking is really important. Right. And I see that too. Right. Like you put a bunch of stuff out there and you’re building a platform or you’re doing great work in the digital sphere and, you’re not really, you know, and your customers are telling you things, but you really don’t have this feedback loop to go back to everybody that needs to know, including yourself about how you’re doing, you know, setting milestones, whether you can achieve, you know, and then tracking, if you hit those milestones, I mean, I think it’s really important to be goal related.

And I try to do that too. And so when I work with a lot of founders and business owners, they’re kind of like, well, can you get me, you know, can you help me grow or can you help me launch? And then I’m back to, well, what is it that you want with this business? What are your desired outcomes? Right. And then if going back to my AB example, if we have our A where we are now and our B where we want to go, then we have to have something over the top of that, that kind of measures how we’re doing. Right.

Like when you plug in navigation into your car, you have some landmarks along the way. You know you’re on your way to where you want to go. And so that’s the same thing with any kind of road mapping or GTM plans or playbooks or whatever you want to call them. Some set of strategies and tactics to get us from A to B, we need constant feedback in that loop back to say, okay, do I adjust what I’m doing or do I stay the course because I’m on the path to where I want to go?

Jeffro (11:27.612)
Right, I mean you’ve got a certain level if you’re not tracking stuff, it’s just a hobby. If you want it to be a business, you’ve got to run it like a business.

So let’s take a look at how today’s marketplace is shifting a little bit. It’s getting more crowded. Authenticity is becoming more and more of a huge selling point. Can you talk about ditching the pitch, being yourself and how this approach has influenced things?

Kevin Dooley (11:55.801)
Yeah, yeah, for sure. had a website up called ditchthepitch .biz for a while and was kind of pursuing that because I help a lot of founders and business owners with their pitch decks. And, you know, everybody wants to do it the easy way, right? Like they want to take Airbnb’s pitch deck template and then put their own content in it then try to present that to people. Like you said, it’s gotten more more competitive.

If you really look at what investors or potential partners, anybody you’re pitching to really want, it’s for you to minimize risk for them and to show them how, you’ve got a big market, you’ve got a unique solution, and you’re the right person to pull it off. And so as you take somebody through slides one through 13 to 15, you’re minimizing risk along the way so that when they get to the end and you ask them for something, money to do things,

then they say, okay, you know, this one looks less risky than these other 10 that I may have, you know, also looked at this week. So I think authenticity and not just filling in a template becomes really important because authenticity, you know, it’s easy to tell your own story, right? So if you be authentic, you bridge authenticity and storytelling together, I’m being open and honest and transparent and authentic about myself, you know, like why I started this business, what I hope to get from it.

how I think I can change the world, why it’s a great investment, why you can trust me to lead this company. And if you do that in an authentic way, as opposed to rehearsing and watching somebody else’s video on what they said in their specific instance, then I think it comes across to investors and other stakeholders really well.

Jeffro (13:42.043)
Yeah, I think people underestimate how important that last factor is. Are you the right person to execute on this pitch that you’re giving me? Because even if everything else looks pretty good, but you’re giving weird vibes to them, they’re like, not worth it. Bye. So important.

Kevin Dooley (14:00.243)
Absolutely. And if they love the idea, they could put you into it for a little while with the intention of putting somebody else in, especially when working with VCs. If they really love the idea and they don’t believe you can pull it off, then you’re gone and somebody else is in there.

Jeffro (14:06.518)
Yeah.

Jeffro (14:16.465)
Yeah. So what else should we know though about positioning and differentiation? That’s obviously one piece of it, who you are and can you execute. But do you recommend any specific strategies for, let’s say, service -based businesses to stand out?

Kevin Dooley (14:31.559)
Yeah, absolutely. you know, I mean, what we’re trying to do is position ourselves, differentiate ourselves, and then have the right messaging to support those things, right? Positioning is where you sit versus other options to solve the problem. Differentiation is how you stand out from those other options to solve the problem. Messaging is how we talk to buyers, right? So I think it all starts with knowing your buyers at a very deep level.

The startups that I’ve worked with and the founders I work with, when I ask them, you know, do you know your buyer? Everybody says yes. Right. Like most people believe they know their buyer yet. A lot of them don’t have product market fit. Right. And they’re a product in search of a buyer. Still you make PMF really, really challenging if you’re not building something to serve a specific market, right. From the get go, right. Like, it happens all the time. Tech founders I work with, right. Like they’re, they solve the problem for themselves. They code and develop something.

solve the problem for themselves and they go, wow, I could build this into a business, right? And then they start, because they’re good at, again, the skillset part of it, they’re good at coding and developing, they just keep building on a platform, build the platform, build the platform, build the platform, and they’re not talking to any prospective buyers as they do it. Most of them skip customer’s discovery, right? Like most successful businesses are started in product definition, right? Like, you know, who, what do they need and why, why are they going to pick you to solve their problem, that kind of thing.

not, or I’m sorry, market definition, who, what do they need and why would they pick you? But most people start in product definition, which is when we build my platform, create some pricing and packages and see who wants to buy it, right? So, you know, so it comes back to knowing your buyer at a very deep level so that you can position to reach them. So you can position for them to see you as an option to solve the problem. Because as a business,

you not only compete against segment competitors, right? AKA other companies that are doing it in a similar way that you are. You’re competing against all options to solve the problem, which sometimes includes do it myself and do nothing, right? So when a buyer thinks about, you know, solving the problem, they evaluate all options to solve the problem. So positioning kind of, you know, is really important and it should be aimed at specific buying groups.

Kevin Dooley (16:47.379)
Again, going back to product market fit, right? Like we can’t get PMF with a wide net approach, right? When you throw a wide net into the market, you get 10 fish, but they’re all different, right? And so I’ve had a lot of tech founders that have done that, right? And then they go to try to get investors and they’re like, well, who’s your ideal buyer? You have 10 customers in the net that, you know, look completely different from each other. I’m not sure you have product market fit yet. In fact, I don’t think you do have product market fit and they don’t, right? So.

Jeffro (17:13.039)
Yeah.

Kevin Dooley (17:16.231)
What we want to do is to go after specific buying groups and then get the positioning right to them. And then differentiation is all about value. Right. So there’s a math formula for value. It equals benefits minus cost. Right. The cost to the to the buyer, the price of the buyer. So do I have my differentiation, you know, benefits list in things, you know, my benefits, are they things that a buyer cares about that a buyer values? Right. Does it make me bigger, better, faster?

A lot of tech founders I work with are so feature focused, right? Feature technology, right? So that’s how I’m going to deliver my service to you. What technology, what product attributes, what benefits are outcomes, right? Those are outcomes that buyers and users get from using your service. So most websites that I see, you know, when I go in and do a digital audit, it’s incorrectly positioned because first of all, they’re talking about features, not benefits. And then they’re talking too much about themselves on their website, right?

Jeffro (17:52.719)
Mm

Jeffro (18:15.759)
right.

Kevin Dooley (18:16.487)
Like, you know, the whole idea of an anchor message, you know, most tech founders, you know, use it to say, Hey, we got the sweetest sauce, you know, in the world. And it’s like, that’s not positioned to a buyer, right? You know, an anchor message, you know, and then I take them through my, my analogy, right? An anchor message, you know, if you’re a boater, right? Like when you decide to go find a cool place to hang out and you throw the anchor overboard, you can’t go anywhere. Right? So your anchor message has to anchor somebody to your website.

Jeffro (18:28.221)
Yeah.

Kevin Dooley (18:45.277)
so they don’t bounce, right? So they look further. And then we’ve got some consumer behavior and some science of buying on, you know, things that a buyer wants to see as they look into, you know, your product or service to solve their problem. it starts with positioning. It starts with knowing your buyer, positioning to them, showing them the value through differentiation, and then talking to them in their words, right? A lot of the founders and entrepreneurs that I coach or consult with,

Jeffro (19:09.71)
Right.

Kevin Dooley (19:14.685)
They’re using their own words, right? Like, and I made this mistake, you know, in our businesses, we’d whiteboard a bunch of stuff in a room and then we’d say, okay, yeah, put that on the website. Well, buyers don’t speak our language that we’re speaking in, you know, in this, you know, conference room with a whiteboard. You got to use their words. And this is where not doing customer discovery comes back to hurt you again or bite you again, because when you do customer discovery, AKA talk to prospective buyers about the problem before you build it.

Jeffro (19:26.745)
Yeah.

Kevin Dooley (19:44.551)
they give you the words you should use back to them in messaging, right? Because you’re doing recorded interviews, you’re writing words that they use down, and now we use that in our messaging.

Jeffro (19:49.143)
Yeah.

Jeffro (19:55.531)
Yeah, and I think, you you’re talking about tech startups, they often start with their pitch decks for the VCs, right? And the VCs might care about the secret sauce that they have. And so while that messaging is directed to them, but if then you just copy paste that to your website for your customers, it’s not going to work for the exact reasons that you’ve described, because now you’re talking to a different person. They’re not going to be caring about the same things. You got to speak their language and translate that message to them.

Kevin Dooley (20:09.491)
Exactly.

Kevin Dooley (20:20.849)
Yeah, for sure. And those same things, right, in marketing technical terms are called purchase drivers, right? What are my motives to pick you as the option to solve my problem? And so that’s the key to getting, you know, positioning correct, right? There’s a thing called a positioning grid, which is one of those two by two boxes, right? That has an X and a Y axis. And if you can make the assumptions, right, and most of the things we do are assumption driven,

If you can make the right assumptions or you can do customer discovery work to get what their motives to buy are, then that makes things very easy for you. It doesn’t guarantee wins, but it makes it easy for you to get your position right. I talked with lot of founders about optimization, right? And a lot of times when I’ll do a website audit, I’m not telling them that this website is never going to drive any sales. What I’m telling them is,

Let’s optimize your website so that you get all the buyers you should, right? Like, like again, targeting specific buying groups and not going wide net. When, when you really look at the value you provide for via on a buying group by buying group basis, there’s going to be one that really stands out or two or three that really stand out. So let’s make sure we get them right. Let’s optimize our website to get them because we’re built to serve them. yeah.

Jeffro (21:43.339)
Yeah. And even if you think of, you know, I like to think of plumbers or something like that. And you talk about differentiation or commercial residential, I’m residential. Therefore I now that’s my product market fit. That’s as specific as I need to get. Like, but no, you’re still generic. You’re now a residential commodity. Like you can start talking about, okay, we do, we handle sump pumps or, you know, sewage tanks, but nobody else does or whatever it is, like get more specific because now instead of your messaging being broad and vague, like we can help with any type of plumbing problem.

You can get real specific about the people who have that sewage pump in their backyard that they have specific problems that you can speak to. And now they’re like, okay, you’re the guy I’m going to hire. Right? Done deal.

Kevin Dooley (22:24.359)
Yeah, yeah, yeah. Yeah, and you get traction in that market, right? And you build systems reaching that customer. And then, so then you’ve got one system built to reach a specific target group. Then you just start teeing up the other ones, right? And if you’re a tech company, you’re going to try to get funding, you say, hey, we got PMF, there it is, PMF in this buying group. And we have these other ones teed up, and we have this system that we built to reach them that we’re going to tweak for each of these additional buying groups.

What do I need? need money to grow this company, right? And so like that’s the authentic story to tell. And it makes sense, right? Because I proved it in once. Now it’s just a matter of implementing my systems, you know, to reach those other buyers.

Jeffro (23:03.874)
Exactly. Yeah. And that takes a little bit of discipline and focus, right? That’s part of the mindset shift. You can’t just go after what sounds good to you or what you like doing. Like you got to think about this stuff from the growing the business perspective too.

Kevin Dooley (23:19.859)
Absolutely, yep, yeah, agree.

Jeffro (23:21.93)
All right, well, we’re coming up on our time, Kevin. Thank you again for joining me today. Business is more than just a game of skills, like we talked about. This mindset component is way more impactful than people realize. For those of you listening, you can use the links in the show notes to connect with Kevin, see what he’s all about and the kind of work that he does. Last question for you, Kevin, before we wrap up. Which do you like being better, a founder or a freelancer?

Kevin Dooley (23:47.039)
How about a founding freelancer? Now, I love the freelance, like the whole freelancer model just makes perfect sense to me. I kind of wish what I was in, I was in an accelerator when the pandemic hit and I was building another software company, a SaaS company. And that’s when I did the deep thinking, the pivot to what I did now. But like it was just getting going, like the whole freelancer model, because it can be so cost effective for people starting businesses now, right?

Jeffro (23:49.526)
Ha ha ha.

Kevin Dooley (24:14.001)
Like I have a specific gap. I’m going to find a subject matter expert in that gap, right? And I’m going to hire them for a short period of time. And then when I have the next gap, I’m going to go find somebody that can do that instead of hiring somebody with a marketing degree. That’s a generalist and really isn’t great at any one thing. So I love freelancing because there, you know, there are certain things I think I’m really good at. There’s certain things I, you know, I’m really passionate about. it allows me to kind of narrow my focus, you know,

Being a freelancer is kind of like being a founder of a business of one, right? Like I have a bunch of relationships with people out in a digital marketing space that I loop in the projects, but you know, my business of one, you know, really gets me going in the morning. And that’s why I can be as creative as I can be, right? Because I don’t have to worry about all the people that I’m connected to and that are working for me or alongside me, right? I’m just creating for one, a business of one. So.

I don’t know. guess if forced to give an answer, it would be freelancer right now.

Jeffro (25:14.028)
Yeah, I mean there’s pros and cons to both, but I like that. And you’ve seen both, so I’m sure some people, grass is always greener, right? If you’re freelancer, like, man, it’d be cool to be a founder and other way too. Well, thanks again for being here, Kevin. Thanks to all of you for listening. Don’t give up, keep growing, get creative, and I’ll see you guys in the next episode.

Kevin Dooley (25:17.139)
Sure,

Kevin Dooley (25:25.659)
Yeah, yeah, for sure.

Kevin Dooley (25:36.435)
Thanks, Jeff, bro.