Why Entrepreneurs Make Better Lovers Than Husbands
28 Jan 2026 · 26 min
Dave Valentine, who built and sold eight marketing agencies over 16 years, explains why entrepreneurs get bored once the business is running smoothly. He shares his lead-generation tactics, how to tell your team you're selling, and why founders need to protect their health.
Questions this episode answers
Portland, Oregon.
Eight businesses.
Over the last 16 years.
The Creative Act by Rick Rubin.
Apollo, ZoomInfo, Seamless AI.
Chapters
Welcome to this episode of the Unnoticed Entrepreneur. If you ever wondered why entrepreneurs make better lovers than husbands, this show is for you. Now, my guest is in Portland, Oregon. Actually, he's left the screen temporarily because I think I've shocked him with that introduction. But we were talking before because Dave has over the last 16 years, account for over a billion dollars worth of revenues, run eight business and businesses concurrently, and has been selling them off successively. So we're going to talk about why you'd start a business and then not want to carry on with that business. We're also going to talk about the impact of running multiple businesses at the same time. Dave's also going to give us some insight into what really still works when it comes to generating all that revenue that he's been helping clients to do. And he's going to give us a book that might surprise you because it comes from the music industry. Dave Valentine, welcome to the show.
Thanks for having me, Jim. Super excited to be here.
Well, we've got to talk about this. Are entrepreneurs better lovers than husbands? What do you think? Where do we go with that?
Yeah, you know, it's a dicey conversation because I've been married for 15 years. Jim.
You'Ve had more companies than marriage. I thought you could say be married 15 times. That's not in the, that is not in the briefing materials.
That's right, yeah. I think there's two different types of people that are entrepreneurs, right, Jim? I think one is someone that loves to start things. I fall into that category. Right. I'm very good at, as a friend of mine would say, launching rockets. Right. Um, I'm not great at managing the systems and putting everything together. I get bored. So my first company, I reinvented it three times in seven years before I sold it. Right. And so like, that's the, the hilarity of it all is that for me, I need something new, I need something dynamic. And so I'm really great. Whenever there's a problem, an issue like we have to make a sale, we need to have a big ad campaign, we need to hire 12, 15 people because we're growing so quickly, sign me up. I'm in the moment that you go, hey, listen, we've got to do human resources reporting for this state and that state and this state. And we need to make sure that we really button up our policies and procedures. I'm not your guy. And so there is something to. The entrepreneur is a better lover than a long term partner simply because there's a fundamentally different headspace And I was actually talking with a friend yesterday who built, scaled up a company from 3 million to 80 million. And he and I were talking about the differences between an entrepreneur and a CEO. And it was just a fun rap, right? Like, it was really, really enjoyable. And he said, you know, to be an entrepreneur, you could get a company up to 10 million a year in revenue, and then at some point, you're going to have to be the CEO. And the CEO thinks differently than an entrepreneur. And as we started to have that conversation, we started to highlight some ideas of what's different. And what was very plain and simple to both of us was he's a CEO and I am an entrepreneur. And there's a fundamental difference.
Yeah, that's, you know, lovely to think of that. And although as I have been laboring over creating a course, I, you know, I'm with you, I. I've realized, you know, consistency is a kind of a different skill set over a long period of time, isn't it, than origination and innovation. They both got their places, of course, in the same way that, you know, being a lothario has a certain role to play at a certain time in the relationship. And then being a consistent husband and father has it in a family stage, a different set of objectives and qualities. But, Dave, I better move away from the lover and husband thing before we get any phone calls or get your wife charging in and telling me that I shouldn't be talking about this. What about risk then, Dave? Do you think that the fundamental difference is risk appetite between an entrepreneur and a CEO, or is it a process versus an origination? And then the question is, what's the fundamental difference and are they sustainable concurrently? In one person?
I had a friend who was also a client whose father fought in D Day. He was on Utah beach. And one of the things that his father always said when he came home was, you got to get off the beach, can't stay on the beach. Whatever you do, you can't stay on the beach. And I think that that's the fundamental function of an entrepreneur. They realize that there's an urgency to get out of the I have to scale role, I have to grow role. So I coach and mentor a number of marketing and advertising agency owners. And oftentimes, what ends up happening in those conversations, Jim, if they're sub $3 million in revenue, sometimes even sub 5 million, they're going, how do I get more leads? How do I get more sales? That is every conversation, right? They will listen to a conversation about operations or management or whatever. And they, in the back of their mind are going, I need more leads, I need more sales. It's about the 3 to 5 million range that they start to go, oh, no, I have people. How do I train them? How do I lead these people? How do I hire? And that's fun too. And I help them with that as well. But the entrepreneur is going, how do I get more leads? How do I get more sales? How do I handle customer issues that are. Because we didn't deliver at an early stage versus a CEO is going, right. And how do I liberate all of Europe? And so the entrepreneur is just going, we gotta get off the beach. And that's a very different mode of operation than someone that's going, I've got a bigger vision for what we're going to do. And it's to get the company to 100 million. That's a fundamentally different form of thinking.
Yeah. And the. And the CEO, perhaps, if you follow that analogy, which is brilliant, is the CEO is sort of really thinking about building the roads and the. And the infrastructure that gets all the tanks to the next town and worries about the logistics. Right.
And that's.
Right. Is maybe not dealing with the same kind of incoming fire and concentrate on an operation. So that. That's a wonderful wonder. Wonderful analogy there, Dave. You've been on the beach several times. You've probably run out of northern French beaches, actually, in that way, you have to move on to Italy, maybe in Spain. So you're going to do a whole European tour. But what about from a communications perspective? Because that's what this show is about. If you start a company, as you know, I've done as well, I've started seven or eight businesses of my own. People buy into you. Right. The first member of staff, the first client in whichever order that comes in that first eight to 10 people, you're still very much almost like a small team or an extension of a family or a social group. How have you dealt with the engagement and the transition from, hey, I know I started this business, but I'm not going to be there for you when you get to the other side of the sand dunes?
Yeah, it's a great question because I have people that come to me all the time like, hey, I'm thinking about selling. How do I even start? Tell your people that it's the goal. Tell your staff it's the goal. Right. So what I always did was I would say, hey, listen, I love all of you so, so much. I'm so grateful to Be working with you. This isn't it. This isn't the end game. The end game is not to have 25 people. The end game is not to have 47 people. The end game is really big. And some of you are going to go with that new company when we sell. That's the goal. The goal is to sell. Some of you will stay here, and some of you will want to say, dave, do you have anything else for me? Right? And so, you know, either way is cool, but I always set up conversations with staff the same way. Jim, there's only one of two ways that this is going to go. Number one, you're going to leave. You're going to say, hey, I want to go work for someone else. I want to go do something else. That's fine. Number two, you're going to get fired by me, right? Like, there's only one or two. You're not. This is not the United States Supreme Court where you die on the bench. It's not going to happen. Right? So I've hired my family, I've hired my close friends, and I've had that same conversation with them. And guess what? I've had people that are very close to me leave, and I've had people get fired. And so when you. When you establish it, you say, look, the outcome is, I'm going to try and sell this company. And I've got a track record of doing that. I'm sure I'll be successful. If you don't want to come work for a company that's going to get sold, then don't work for me. If you do, if you find that exciting, if you find the growth exciting, you know that we're going to grow really, really fast. We're going to add lots of people. It's going to be kind of like a party, then come. And there is something, I think, Jim, in a personality for people as well, not just the entrepreneur. I found that there are employees that are really excited by that prospect of building something and then moving on to the next thing as well. And there are certain employees that are like, I want to build a thing. And then as soon as I say, hey, we've sold, they start looking for another job. Not because of anything other than they're like, I love Dave. Dave's my guy, and I don't want to work with anybody but him. When it comes to the clients, though, every time that I've sold a company, Jim, I try and sell it in a way, and at a point where I haven't been doing sales for at least two years. So what that does is most of the clients, most of the customers know that I exist, they don't know me. And so whenever I leave, it's not a big suck on the company at all. They know that I was there and now there's a new ownership group and they don't care.
Yeah. So Dave, I think it's a fantastic point there that you made make actually make a lot of fantastic points. But you know, one is about the, the transparency with the team and the people and also attracting people who are not looking for their last job. Right. But who are also equally dynamic.
That's right.
I always used to say to people this is not a family, it's a team. Because in families you don't fire your sister, but in a team you all have to compete to be on the field. Right. Y and that people get subbed in and subbed out and sold on and bought in. And also this idea that you are being very clear with your clients that you're not mission critical to the business because if you're mission critical to the business, actually the buyers aren't going to want it in the first place. So you have to then be very clear about that. So that's wonderful that you've shared those insights. Dave, is there something that you did with all of these different agencies? Because I think they've all been marketing related agencies that was particularly successful from a marketing point of view in terms of building the brand and bringing in leads. Because plainly you're wearing a Manchester City shirt. For anyone that knows about football, Dave will know that wearing a man City shirt would appeal to very small number of potential customers. You know, if you had a red shirt on from Manchester, he might get more. But, but joking apart, Dave, you know, obviously you know, being a member of Manchester City supporters club would have won you one or two clients. But apart from that, what any particular strategies that you've used that the rest of us that are not Man City fans could use?
I really. By the way, that's funny, Jim, thank you. And I really feel like I belong in the UK and that I'm displaced. I have this weird accent that prevents me from moving there permanently, but I get along with people much better. So anyways, the point is, yeah, the thing that I found that works really great is cold email outreach. It's how I built my first business in 2013. It's how I built all of my businesses even now in 2024. It's just the thing that gets you into the Space of big decision makers. And I just to prove that it worked. So we're recording this in middle January, three weeks ago, we had a. I had a client who booked a meeting with a consulting firm, and it turned into a $1.8 million deal for my client, $150,000 a month. And I helped them close the deal, Jim, because they're like, we, they were going to try and sell it for like 15 or 20 grand a month. And I said, oh, no, timeout. What you're doing is worth so much more. And so we talked about like, hey, you're really worth like 300,000 per month here, which blew their minds, right? And I said, but I know you need the client because they did. They sincerely did. And let's go get this. And so we had this conversation. We said to the client, look, Normally we charge 300 grand. We want to work with you, though. What could you pay us over 12 months? Let's figure it out. So they came back with 100 grand. And we said, can't do it for that. That's a little bit low again, by the way. 100 grand a month would be their biggest sale ever. Times like 3, 4. 4. And so when I went back and I said, actually, we're going to, we're going to do 150 grand. 1.8. And then we closed it. They looked at me like we discovered fire. The reality is, Jim, cold email outreach gets you into the, the lives and the spaces of individuals that have never heard of you. They're usually at larger corporations, not always. And it's the most cost effective way to reach them. Digital advertising, everybody thinks that that's the place, and it certainly helps. It's not a bad spot to get new clients. It's exceptionally expensive. You're going to have to disqualify an inordinate amount with cold email outreach. When you do it well, you get the right lists, you're able to hit up your ideal customers that have the budgets that you're looking for, that have the level of professionalism that you want to work with, and subsequently, you have a very good close rate.
Dave, how are you getting those emails? We say, cold email outreach. How are you getting those emails?
Yeah, I blew another client's mind last week when we went and looked at Apollo I.O. and I said, okay, who do you want to target? And she threw out consumer packaged good companies, Right? And so I throw in the parameters for that at large corporations and we start scrolling through, and she says, hang on, wait a minute. You're Telling me you just typed this in for, I think it's 50 bucks a month. You just type this in for 50 bucks a month, and all of a sudden I can be meeting with the head of Hershey's and I'm like, yeah, here's his email address right here. And she's like, that is why. How did I ever run my business without having this information? So there are a lot of databases out there. Apollo's a great one. ZoomInfo is very, very good, but it's also exceptionally expensive, so I don't recommend for entrepreneurs. The other one that I really like is called Seamless AI. It's quite good. S E A M Seamless AI. It's very, very good. It's scraping LinkedIn. And so you can basically get about 30,000 contacts a month for about $300 a month. It's pretty good. And so you're able to use any one of these databases to really leverage. And they're always new ones, too, Jim. So if you go to appsumo.com you will find deals where you can get lifetime deals from specific databases that are just getting started. And usually you'll get them on the cheap. Maybe 100 bucks. You get a lifetime deal of 10,000 contacts per month. And so there are different ways you can go about this, but the general rule here is go find a database. It's going to make your life a whole lot easier.
Well, that's amazing because, Dave, you've mentioned, is it called Apollo, as in, like the rocket ship Apollo? I hopefully won't meet the same fate. But it says one platform to close them all. Yep. And it has, you know, millions of sellers. Over half a million companies beat their number with Apollo. So, you know, they've got 275 million contacts. Of course, that's less than LinkedIn. Right. With its 6,700 million. But you're getting presumably a detailed and broken down and usable mailing list of people that don't feel as though they're being tackled at every twist and turn on LinkedIn. So thank you for that, Dave. That's absolutely fantastic advice there. Dave. We're going to touch on something that's a little bit more sanguine, if you like, because, you know, putting, you know, putting your energy into that many companies simultaneously, and I've run a few concurrently myself, and it's pretty exhausting.
Yeah.
And I did ask you whether you're willing to share about this, because a topic that we don't often touch on is about mental health and mental wellness, because One of the reasons perhaps you've also been selling down these businesses is to kind of get to a normal state of life when it comes to sort of work rates and so on. Do you want to share with us just how have you been impacted by running all these companies and how did you sort of work your way through to a place where you'd be in a, in a good place and a place where you can have a good laugh with a complete stranger like me from England, who's not a Man City supporter.
Okay, Jim, none of us are perfect, so I forgive you. And.
Being British or.
No, no, you're my favorite people. You're my people. I. One of the things that I struggled with, four years into my first company, I went to my doctor and they did a stress test amongst a myriad of other blood work and whatever. We just had our second kid and my wife was like, you know.
You.
Haven'T had a physical since you played proper football in college. It's been a while, so maybe you should go get a physical. So I did. And in the course of going back the next week and talk with the document, sat down and the doctor said, hey, Dave, I just got one question for you. How do you know you're going to have a heart attack? And I was like, I don't understand the question, Doc. And he goes, how do you know you're going to have a heart attack? I'm like, repeating the question doesn't help me understand it better. He goes, you don't know if you're going to have a heart attack. You just have one. He said, You're 29. We've tested 4,500 people. You're the most stressed out person we've ever tested. Like, you're off the charts. You win. And he said, if you don't change your behavior, you're not going to make it to 40. So that took me on like a trip, right, Jim, of like, what do I do now? At the time, by all standards, I'd been successful. So in the United States, if you have a million dollar business, if you do a million dollars in one year, which I did in 2017, you were in the top 7% of all companies in the U.S. if you are an agency doing that, you're in the top 3%. So I was in the top 3% of all agency owners. And I'm stressing myself out into the grave. So I had to figure out how to do things differently. It started very simply with, hey, I'm going to take a walk for five minutes and I'm going to drink a glass of water because I had this terrible habit, Jim, where I'd go from drinking coffee all day to like 4 o' clock to, to opening a pint and sitting down and enjoying that. And I, so I switched from caffeine to alcohol seamlessly so bad and, and sometimes there would be days where I wouldn't have drank a single glass of water which sounds absurd to me now, but at the time it was how I was living my life. So I set the bar very low. Hey, one glass of water and a five minute walk. Now most days I would have multiple glasses of water because I was thinking about it. Most days I would go for a 30, 45 minute walk. But I had been an athlete in high school and college and so for me I'd really let myself go. I just stopped working out because why? Blinders on. I'm building the company, right. I'm also a new dad so there's a lot that's happening that's not conducive to me making time for myself. So I really had to get back to going, what do I need? And at this point, you know, it's 2024, it's seven years after that event at this point. Jim My self care routine is pretty robust. I've been on the road for the past month doing speaking gigs and holidays and whatnot so I haven't been able to do it as much but usually it's hey, I sauna every day, I do a cold plunge in the river every day, I go work out every day I'm lifting weights and, or running and staying in some sort of shape, I meditate and all of those things are, are really feeding the hey, Dave needs to be well beast, as it were.
Dave Valentine I think that sounds fantastic and you don't want to get too late in life to realize that the health is really the wealth that we all need.
That's right.
Because there really is no point in having all that money and being unable to enjoy it. Dave plainly you've given yourself plenty of time to relax and literally let your hair down. What about reading or listening? Because I love to ask entrepreneurs, you.
Know.
What books or audio are they getting enjoyment and inspiration from?
Yeah, I actually just recommended this to a friend last week. It's called the Creative act by Rick Rubin. He's a music producer in la and it's this like very, it's great for entrepreneurs because it's bite sized chapters. Right. It's as we were discussing before Jim, it's two to four pages per chapter. Very short, simple ideas that have been cataloged and that are really inspirational. Whether you're a creative in business or not, the reality is if you're an entrepreneur, you are a creative because you're problem solving and problem solving requires. Necessitates creativity. And so I highly recommend it. And it's just this beautiful big permission book. And I do recommend that you go look up who Rick Rubin is. He's got like an Einstein like hair effect going on and a beard down to his belly button that's, well, that's very unkempt and he surfs every day. He, he is what you think of as an LA music producer. You've got it. He's a fascinating character and his book is remarkable. So I can't recommend it highly enough.
Dave Valentine, I can't recommend highly enough time with you as well. If people want to find out more and get a chat with you, maybe, maybe talk about the Premier League, how can they do that?
So you can go find me on any social media channel at my handle is EAL R E A L D val D V A L Tick tock, Twitter, Instagram. I'm on all of them. And then as far as reaching out to me personally, daveave Valentine co is the best way to get to me. Hey, I'm giving you my email. Practice what I preach. Find me where I'm hanging out at. I'm hanging out in my email inbox, so find me there.
Great. I'm gonna, I'm gonna think of something to sell you, Dave, now I've got your email address. Do it, Jim. Manchester United merchandise.
Oh, come on.
Well then, then you could leave it out the Portland cold, couldn't you? So like to get revenge actually these seasons you don't need any revenge against me. They're inflicting on themselves. Dave Valentine, thank you for joining me so much on the Unknown Entrepreneur show today.
Jim, it was such a pleasure. Thanks for having me on, brother.
It's been wild. So maybe Dave, we'll see him over here in the uk, but if not, check him out. He's in Portland, Oregon, but you can get him on his website. Of course. I'll put his details again in the show notes as. And we've talked there really about entrepreneurs being great lovers, not necessarily great husbands. Of course we can be great husbands at home and still be great lovers in business. So it doesn't mean that we're inconsistent and love starting new things in the office and in the home. We can actually have almost sort of bipolar disease, where we are good at starting things in the workplace, but also great and be consistent men and husbands and fathers and so on, sons and brothers. Perfectly possible to do both of those. And Dave is an example of that. And the other takeaway there, of course, is using email. Apollo IO. Thank you for that, because that sounds like a really nice alternative to spending lots of money on Google Ads. And also fundamentally, that this is a journey, but we must look after the vehicle on the way. The health of our body is paramount or we're just not going to get to the destination. So thank you to Dave for all that wisdom and hearty chortles as well. So thanks for joining me. Jim James from the UK Dave's Important, Oregon Wherever you are today, we hope you're doing well and just encourage you to keep on communicating.
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