One Question Series with Dan Kieran: What's the one thing you wish founders & CEOs in SaaS knew?

Hi, welcome to the next episode of the One Question series. Today I'm super excited because we have Dan Kieran with us. Welcome, Dan.

Thank you for having me.

So Dan is an entrepreneur. He has gone through the scale journey as a CEO himself, exiting the business, and since then is now an award-winning author and mentor. The one question we are asking you today is, what's the one thing you wish Okay.

Well, for me, I call it the second journey and everybody's talking about the first journey, which is all about how the business works, scaling, running a business, sales. But I discovered there's a second journey, which no one talks about, which is the leadership journey. And I discovered that running my own business, and that was the journey to the edge of what you think you're capable of. And that was the journey that determined whether or not I made it. Anyone who is an entrepreneur knows all your faults are put under a microscope and a spotlight at the same time. I discovered that I was going to put those flaws in my business if I didn't deal with them. And actually, the outcome of the second journey is more important than the first. But what tends to happen is that people neglect their own individual journey, and it's the thing ultimately it rests on. If you're CEO, How you're feeling in your own head is what success or failure in the business ultimately depends on. So it's critically important, but people don't tend to talk about it because everyone has to portray themselves as being fine and successful, and I'm smashing it and everything's amazing. And you can't tell your investors that you're struggling or you're questioning things. You can't tell your staff because you've got to be this figurehead. So you've got all this strain around behaving in a certain way that can be incredibly toxic. And so I I'm really interested in that space because I think leaders don't talk about it enough. And as I say, it's totally aligned with the success of your business because your business depends on your state of mind. So all the work you can do to fortify that, um, literally pays dividends.

Can you take us back a step? So talk us through what happened in your journey.

Yeah, so we were a tech business and a publishing business. It was all super exciting, but as a leader Like, I would say this, that as a sort of entrepreneur and a CEO, it's the one job title that you get given before you've proven you're capable of actually doing it. There was this sort of delta between my job title and my LinkedIn status update. And so the way I tackled that was essentially by learning to lead myself.

Hmm.

I always say being an entrepreneur is like going to a casino with your reputation. By the time you realize that, your reputation's on the roulette wheel and it's spinning. So you're in a very heightened state of anxiety, and it's all about bravado, and it's just an incredibly difficult headspace to inhabit.

That's really fascinating because in Tarifa earlier this year at the whole Revenue Summit, in the lead-up to the event, as I was doing a lot of research and speaking with the CEOs that were attending, the most— the sessions that were resonating the most with them were all about how to operate at an elite level and still maintain a calm life around you? And can you actually do that? And is that possible? And it's really interesting because even to get to the level of a CEO, you already have to be pretty special. You have to be pretty excellent in some way to be operating at that level in the first place. But the challenge then comes, it's so much greater because you have all of this external, all of these stresses that come on top of that, that make it even more difficult to operate. And so, how— what we would love to do, what we want to do, And what we seek to do at Rebolesco is to be able to support that CEO so that they're able to make the right decisions, so that they're able to see around corners when they haven't navigated that journey before.

The huge problem with them around being a leader now is so much of it's fear-based, fear decision-making. And I, so I discovered over the course of my time running the business that it was the softer approach that actually delivered. And then the pandemic hit. And by that stage, I couldn't afford to do anything that didn't work. So I moved over to that more softer leadership style. And after that, when I— after leaving the business, I started to just research leadership, like where does it come from? And I found that the etymology of the word lead is really interesting. The etymology of the word lead, um, from a language called Proto-Indo-European, which no one speaks anymore, but this is the language that Sanskrit and ancient Greek came out of. And Linguists have figured out that they think the origin of the word lead meant to flow. And in my research about how we'd lived for, you know, 95% of our existence as a species, we lived in small groups, 20 or 30 people, like classic startup kind of size company.

Mm-hmm.

They didn't have any concept of power. There was no patriarchy. However, they led these groups to achieve collective goal that they were pursuing, i.e., to survive and thrive in the landscape. Whatever they were doing was incredibly effective. And I find it fascinating that the, the reason the word lead means to flow is because they were adopting the behaviors of the rivers to thrive as a group, to achieve this collective goal. And then I started to look at the way rivers behaved, and it's really interesting because they're powerful, but they're also very gentle. They have currents. They're part of an ecosystem. They're not abstracted.

Yeah.

But it's also a paradox because they're separate from their ecosystem that they're in, but they're also critical to it. And I just started to develop this really interesting business philosophy that's based on a more connected sense of what it means to lead. And it's, it's a work in progress. I'm doing a book called Lead Like a River now. I'm writing at the moment, and it's all about using a river as a leadership analogy because the more I look at it, the more it holds up. And I feel like it takes account of our way of being and behaving that I learned was effective when I ran my business. My view is that female power is massively underused. When I've been interviewing a lot of female entrepreneurs for the book, and I had a really interesting generational split. The older women felt like to be leaders, they had to be like men.

Yeah.

And then there's a younger generation of leaders who are consciously not doing that. But I've spoken to some female founders in their sort of mid to late 20s, and they're not having any of that. They're like, we're doing it our way. Like, we turned down VC money. I spoke to a brilliant woman. She said, no, I turned down VC money because I realized if I took their money, it would make me change my values.

Oh.

Like, this is like the most boldest, toughest entrepreneurial statement I've heard in a long time, right? Um, and most men fall for the, oh, VCs. I mean, I've seen this in events. I've seen, genuinely seen entrepreneurs say, if you don't have VC money, you're not a real entrepreneur. So there's a kind of really interesting questioning, and there's a lot of cosplay macho leadership going on. Leadership isn't about that. Leadership is about following your instincts, like going where the evidence shows is the right way to be successful. That slightly more enlightened, human-focused, um, way of leading actually delivers. And that's so much better for bosses.

Mm-hmm.

Because the problem I think the certainty that I face as a CEO is that I kept hitting my goals and not feeling anything. You know, I would go past £1 million in revenue, didn't even notice because I'm too busy trying to get £1.5 million. And then I get to £2 million and I'm not even— didn't even notice because I was trying to get £3 million. And then I didn't even notice because I was trying to get to £4 million. And it taught me that meaning is relational, right? It doesn't happen at the end of something. I was interviewed for a radio program recently, and they're friends with Matthew Pinson, who won his 4th gold medal rowing a few years ago. And this guy said, well, had asked him how it felt after winning his 4th gold medal, and he said, relief. So I think there's a, there's a huge thing there too. Like, we're all aiming for this, we're all trying to get this prize, we're trying to get these revenue numbers and these profit numbers.

Yeah.

There's a bit of a conspiracy of silence around that because it doesn't really feel very great when you get to them. And I think that, yes, meaning deficit is something that is a huge— plays a huge role in keeping CEOs interested, um, when everybody's in building their businesses.

So the question is, how should CEOs be thinking about that?

Well, that's— I mean, for me, that's the most interesting, exciting question. Um, and I've worked with entrepreneurs who are interested in that process. I left my company when I stopped finding it meaningful. There's no doubt that if somebody had put their arm around me at that point and gone, you've done a great job, Maybe you just need time to get your head together. You're about to make a big decision, you know, and like that didn't happen for me. And I'm trying to do that for entrepreneurs because that is the point. If you don't have meaning running the company, you won't have it afterwards. And I did a talk to exit entrepreneurs a few months ago and they all said the same thing. One guy just bought a house next to some fancy golf course and he was like, I didn't even celebrate when I made my second $200 million. And it's that meaning deficit. And how you find that— well, you have to find out why you did it in the first place. I do a piece of work called Origin Myth where I figure out how you're connected emotionally to the work you're doing. I had all these badges— founder, CEO— and that's because we build these businesses out of ourselves. So the idea of losing them is like losing part of ourselves. So what I help people do is, you know, you build it out of yourself, but then you have to extricate yourself from it in the process of doing it so that when the end comes, which, you know, maybe it's exit, which is great, maybe it's not, maybe you go under, maybe— I don't know, who knows what's going to happen. But whatever happens, you feel you've got that meaning back, um, because that in the end is the only exit you can trust. It's the way running your business changes the way you see yourself.

Do you think— because a lot of, a lot of people say that the meaning of happiness, um, or whether you have a happy life, it comes down to the quality in the relationships that you have with other people near you. Do you think that's the universal truth for all humans on Earth?

That's a question. Um, yeah, I mean, it's— I'm reading lots of books at the moment in my quest to understand indigeneity and indigenous thinking, and One of the most interesting concepts I've come up, noticed, and discovered is that post-Enlightenment, René Descartes, he basically said this very famous quote, which is, I think, therefore I am. And we all in the West kind of live according to that. We think that we exist in our own heads, and we sort of— we're separated from the world, and we are existing in our own brains, and that's it. And we're cut off from everything else. But But in indigenous thinking, there's an amazing writer called Tyson Yunkaporta, and I heard him talking about this, and he said in indigenous knowledge, it would be much more appropriate to say, I'm located, therefore I am. Which is that you get your sense of who you are not from your brain, but from the way you relate to the world around you, your community, the land itself, what you're doing, your family.

Yeah.

And I think there's some utterly critical kernel of meaning and truth in that statement is that we see ourselves as taking our sense of identity, like, from just who we think we are rather than how we're showing up. Um, and it's how we attend to the world, it's how we show up in the world, how we relate to the world. That's who we really are, and that's where meaning is. Because meaning, you know, in the end, Mm-hmm. you're not gonna find it in an exit. You're not gonna find it in building a company of a bigger and bigger size. But there's this massive meaning deficit in entrepreneurship, and you have to be aware of that, and you have to be fortifying your relationships, your sense of meaning, your connection to the environment that you're living in, like physical and emotional. So I mean, it's all about relationships.

Yeah, it's really interesting, that point about being located, because it's maybe when we naturally say, I feel lost. It's because we don't feel located.

Totally. Exactly that. And what I'm excited about is how you can go on a journey to figure that out. Can you go through that process without leaving your company? Can you be involved with it in a way that means you don't have that meaning deficit? And I think that's really interesting. But so many founders, they get to the stage that I got to. A friend of mine literally Yesterday, you know he's just just got out of his business, and the headspace between knowing you want to leave and leaving like that is the hardest headspace to navigate. Like that's the true test of entrepreneurship.

How do you start working with CEOs? What's the thing that you tend to do with them? Is it a framework that you can put everybody through, or is it just really individual?

No, it's the same for everyone. It's basically it's called your origin myth, and I work out. Why you do what you do. I have a theory. Some people don't like this, but my theory is that all entrepreneurs feel inadequate in some way, which is why they have to go out into the world and create this big thing that other people around them tell them has value in order to fortify their sense of identity. That's certainly how I did it. I'm like holding my hands up, right? 100%. Yeah, yeah, yeah, yeah. Every entrepreneur I've ever met after a few beers agrees, even if they—

Really? I was gonna ask you.

I'm not saying there aren't entrepreneurs who don't agree with it, and fair enough. I'm not suggesting everyone is like this, but everyone I've met, that's absolutely what's going on. And so what we do is we use it— we're using our professional lives to soothe that wound, whatever that wound is. But the thing about wounds is they give you compass and they give you energy, because every success I've ever had in my life has been acting in a way that soothed my wound. But it, it made me absolutely obsessed to stop other people being overlooked. You basically rewrite the story of yourself to re— to start the process of restructuring the way you see yourself, and you change your role in your own life by doing it. It's insanely powerful. But the reason it's brilliant for entrepreneurs is it reconnects you with why you did it in the first place. I think the most important thing is to understand why you're doing what you're doing. Connection from that.

What will be some of the Indicators that show me I really need to start thinking about coming back to the why?

Well, I think, so everybody always knows, it's just how much you're admitting it to yourself. So it will be, I had a really bad stomach problem I was taking medication for, for 3 years. When I left my business, within 2 weeks I didn't need it anymore. Yeah, I mean, I wasn't sleeping. That's your unconscious mind saying, this is the most important thing for us to deal with right now. You have to listen to your body and Talk to the people closest to you. Ask them how they think you are.

Mm.

It's a question of how do I make myself act on what I already know, but I don't feel I know how to deal with it. Like, that's the question most people stumble with because they'll just drink more or do more triathlons.

Yeah.

Performative stuff that's not really getting them anywhere. But it's so much better if you engage with it before that point.

Oh, well, thank you so much. That was, uh, super, super motivating as always chatting to you, um, and exhilarating. And you're going to be joining us, you're going to be joining us in Tarifa next year at the Whole Revenue Summit, right?

I'm so excited to come. Yeah, I couldn't come last year, this year, but I am so excited. Yeah, I can't wait. And I love everything you've shown me about it. Looks incredible. I can't wait to be there. And yeah, and it's going to be great fun to figure out some events and Yeah, I can't wait. Can't wait.

Definitely. Yeah. Awesome. Cool. All right. Well, we'll, we'll talk to you soon. Thanks, Dan.

No worries.