Why Entrepreneurs Make Better Lovers Than Husbands

Can’t commit long-term to a business like you can a marriage? Serial founder Dave Valentine explains the mindset gap between high-energy entrepreneurs and steadfast CEOs.

Learn Dave’s tactic for prepping staff and buyers that he’ll eventually leave or sell each venture. Hear how cold email outreach consistently wins clients despite hot digital channels. Discover the health wake-up call that forced Dave to finally unwind amid startup chaos.

If you constantly crave new creations over stable systems, Dave will help you self-analyze. His candid insights bridge starting up and smart scaling for those wired to invent but not operate. Take heed before you sacrifice sustainability while launching your next rocket.

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Transcript

Jim James (00:02)
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 important, 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,

eight businesses concurrently and has been selling them off successively. So we're going to talk about why it started 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 insights into what really still works when it comes to generating all that revenue that he's been helping clients to do.

And he's gonna give us a book that might surprise you because it comes from the music industry. Dave Valentine, welcome to the show.

Dave (01:04)
Thanks for having me, Jim. Super excited to be here.

Jim James (01:07)
Well, we've got to talk about this. Are entrepreneurs better lovers than husbands? What do you think? Where do we go with that?

Dave (01:17)
Yeah, you know, it's a dicey conversation because I've been married for 15 years, Jim. Uh, but.

Jim James (01:23)
You've had more companies than marriage. I think you're going to say be married 15 times. Now that's not in the briefing materials.

Dave (01:30)
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? 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 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 1215 people, because we're growing so quickly. Sign me up, I'm in the moment that when 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 entrepreneurs a better lover than a long term partner simply because there's a fundamentally different headspace.

Jim James (02:43)
Hahaha

Dave (02:58)
And I was actully talking with a friend yesterday who built a scaled up an 80 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 it was a fun rap, right? Like it was 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 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.

Jim James (03:38)
Yeah, that's lovely to think of that. And although, as I have been laboring over creating a course, I, you know, I'm with you. I've, I've realized, you know, consistency is a kind of a different skillset over a long period of time, isn't it? Then origination and innovation, they've both got their places, of course. Um, in the same way that, you know, being a Lothario has a certain role to play at a certain time of the

relationship and then being

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?

Dave (04:11)
That's right.

Jim James (04:34)
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?

Dave (04:48)
I had a friend who was also a client whose father fought in D-Day. He was on Utah Beach. One of the things that his father always said when he came home was, you got to get off the beach. You can't stay on the beach. Whatever you do, you can't stay on the beach. 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's the, 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 three to five 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 gonna do and it's to get the company to 100 million. That's a fundamentally different form of thinking.

Jim James (06:21)
Hehehe

Yeah, and the CEO, perhaps if you follow the analogy, which is brilliant, is the CEO is sort of really thinking about building the roads and the infrastructure that gets all the tanks to the next town and worries about the logistics, right? And is maybe not dealing with the same kind of incoming fire and can concentrate on operations. So that's a wonderful, wonderful analogy there. Dave, you've

Dave (06:49)
That's right.

Bingo.

Jim James (07:02)
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 and Spain. So you're gonna 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 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.

Dave (07:08)
Ha ha!

Ahhh! Yeah.

Nah.

Jim James (07:33)
That first eight to 10 people, you're still very much almost like a small team or 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?

Dave (07:55)
Yeah, it's a great question because it, you know, I have people that come to me all the time. They're 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, but 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 wanna say, Dave, do you have anything else for me? Right? And so 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 gonna go. Number one,

you're gonna leave. You're gonna say, hey, I wanna go work for someone else. I wanna 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 gonna happen, right? And 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

Jim James (09:13)
Hehehe

Dave (09:24)
leave and I've had people get fired. And so when you establish it, you say, look, the outcome is I'm gonna 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 wanna come work for a company that's gonna get sold, that don't work for me. If you do, if you find that exciting, if you find the growth exciting, you know that we're gonna grow really, really fast. We're gonna have lots of people. It's gonna be kind of like a party,

Jim James (09:28)
Yeah.

Dave (09:54)
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 wanna 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."

Jim James (10:17)
Yeah.

Dave (10:23)
and I don't wanna work with anybody but him. When it comes to the clients though, every time that I've sold a company to 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, ha ha, 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.

Jim James (10:58)
Yeah, so Dave, I think it's a fantastic point there that you make, I guess you make a lot of fantastic points, but you know, one is about 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. And 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? And that people get subbed in and subbed out and sold on and bought in.

Dave (11:13)
That's right.

That's right.

Jim James (11:28)
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

Dave (11:40)
That's right.

Jim James (11:57)
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 a very small number of potential customers. If you had a red shirt on from Manchester, you might get more. But joking apart, Dave...

Dave (12:10)
Ha ha ha!

Yeah.

Ha! Very popular. Yeah, yeah. Hehehehehehe.

Jim James (12:28)
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?

Dave (12:33)
Hehehehe

I really, by the way, that was 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've 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.

Jim James (12:53)
Hehehehe

Dave (13:13)
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 were like, they were gonna try and sell it for like 15 or 20 grand a month. And I said, "Oh no, time out. 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 have this conversation, we said to the client, look, normally we charge 300 grand, we wanna 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, ah, 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 three, four. And so when I went back and I said, actually we're gonna 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 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 everything so that's the place and it certainly helps not a bad spot to get your client.

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 wanna work with, and subsequently you have a very good close rate.

Jim James (15:27)
Dave, how are you getting those emails? When you say cold email outreach, how are you getting those emails?

Dave (15:34)
Yeah, I blew another client's mind last week when we went and looked at Apollo.io 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 she, 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 typed 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. Zoom Info's

Very, very good, but it's also exceptionally expensive. So I don't recommend it 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 a hundred 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 gonna make your life a whole lot easier.

Jim James (17:30)
Well, that's amazing because Dave, you've mentioned, is it called Apollo as in like the Rocketship Apollo.io? Hopefully won't meet the same fate. But it says one platform to close them all. And it has millions of sellers, over half a million companies beat their number with Apollo. So, they've got 275 million contacts. Of course, that's less than LinkedIn, right, with its 600, 700 million. But you're getting...

Dave (17:36)
That's it.

Yep.

It is.

Jim James (17:58)
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 day. That's absolutely fantastic advice there. Um, Dave, we're going to touch on something that's a little bit more sanguine issue like because, you know, putting, you know,

Dave (18:10)
That's right.

Absolutely.

Hehehe

Jim James (18:24)
putting your

energy into that many companies simultaneously and I've run a few concurrently myself. It's pretty exhausting. 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 get to a normal state of life when it comes to work rates and so on.

Do you want to just 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 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?

Dave (19:11)
Okay, Jim, none of us are perfect, so I forgive you. And, no, you're my favorite people. You're my people. 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 had just had our second kid.

Jim James (19:17)
You mean being British or?

Dave (19:41)
And my wife was like, you know, you haven't, you haven't had a physical since you played proper football in college, it's been a while. So maybe, maybe you should go get a physical. So I did. And in the course of, you know, going back the next week and talk with the doc, sat down and the doctor said, hey, Dave, I just got one question for you. How do you know you're gonna have a heart attack? And I was like, I don't, I don't understand the question doc. And he goes, how do you know you're gonna 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 gonna 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 gonna 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 had 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 US. 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, right? Go from drinking coffee all day to like four o'clock to opening a pint and sitting down and enjoying that. And so I'd switched from caffeine to alcohol seamlessly. Oh, so bad. And sometimes there would be days where I wouldn't have drank a single glass of water, which sounds absurd to me now.

Jim James (21:30)
I'm sorry.

Dave (21:36)
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?

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, 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 really feeding the hey, Dave needs to be well beast, as it were.

Jim James (22:58)
Dave Valentine, I think that's 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, 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

Dave (23:07)
That's right.

Jim James (23:23)
because

I love to ask entrepreneurs, you know, what books or audio are they getting enjoyment and inspiration from?

Dave (23:34)
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 L.A. 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 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 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.

Jim James (24:35)
Yeah

Dave Valentine, I can't recommend highly enough time with you as well. If you want to find out more and get a chat with you, maybe talk about the Premier League. How can they do that?

Dave (24:56)
So you can go find me on any social media channel at my handle is @realdval, R E A L D V A L. TikTok, Twitter, Instagram. I'm on all of them. And then as far as reaching out to me personally, dave@davevalentine.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.

Jim James (25:22)
great. I'm going to think of something to sell you, Dave. Now I've got your email address. Maybe I'll sell you some Manchester United merchandise. Well, then you could leave out the Portland cold, couldn't you? So like to get revenge. Actually, these seasons, you don't need any revenge, as mentioned, they're inflicting it on themselves. Dave Valentine, thank you for joining me so much on The Unnoticed Entrepreneur

Dave (25:27)
Do it Jim, I dare you. Oh come on.

This. That's right.

Oh.

Jim James (25:45)
show today.

Dave (25:47)
Jim, it was such a pleasure. Thanks for having me on, brother.

Jim James (25:50)
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 always. And we've taught there really about, you know, 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. You know, so it doesn't mean that we're

Dave (26:14)
Hehehe

That's right.

Jim James (26:19)
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 sons and brothers. Perfectly possible to do both of those. And Dave's 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 gonna get to the destination. So thank you to Dave for all that wisdom and hearty turtles as well. So thanks for joining me, Jim James from the UK. Dave's in Portland, Oregon. Wherever you are today, we hope you're doing well and just encourage you to

Keep on communicating.