Episode 345 · 15 October 2026 · 52:08

Values don’t spread. Stories do. With Matthew Hook and Caroline Keylock

Featuring Matthew Hook, Caroline Keylock

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Al ElliottWe're going to hear a story of a founder who sits down with his senior team once a year and asks them just one question. Should I still be the CEO of this company?

Caroline KeylockAnd he said to his senior team every year, every year, I'm going to have a particular point in the business calendar where I am going to reconsider whether I should still be the CEO of this business, whether I'm the right person to continue to lead the business, or whether someone else should come in. And I should have a slightly different role. And every year, he transparently went through that process with them, you know, assessing the next stage of growth, everything they were trying to achieve. And then in a certain year, he stepped back, and he didn't step away from the business. He actually went into like a head of innovation role. And for his investors' benefit, he was still like chairman of the business.

Leanne ElliottHe is the exception. For most companies, it goes like this. Someone launches a new set of values. Again,

Al Elliottour guests today say the problem isn't the values, it's that they only ever come from one person's head, and values just don't spread, but stories do.

Leanne ElliottMatthew Hook and Caroline Keylock help businesses tell stories that work when the founder isn't in the room. But this isn't just for founders, it's for leaders everywhere. Hello, this is Truth, Lies and Work, the award-winning podcast where behavioural science meets workplace culture, brought to you by the HubSpot Podcast Network, the audio destination for business professionals. My name is Leanne. I'm a Chartered Occupational Psychologist.

Al ElliottMy name is Al and I'm a business owner.

Leanne ElliottAnd we are here to help you simplify the science of work.

Al ElliottNow, Matthew and Caroline are the co-founders of Look Up, a storytelling consultancy. Their idea is simple. Everyone's heads down, so stories help us look up. Half their clients are nonprofits and purpose-led businesses, and they take on a pro bono project every month. Nice guys.

Leanne ElliottCaroline's background is in news magazines and fashion. Matthew has spent 25 years as a strategist, including evaluating acquisitions. So they've seen what a story is worth from both sides of the table.

Al ElliottAnd here's why it matters today. Most of us are treating storytelling as marketing. Matthew and Caroline say it's the thing that helps decide who makes decisions in your business.

Leanne ElliottAfter the break, we find out why your team feels permanently busy and what it has to do with you. And Al, I'm looking at you here. They have some pointed things to say about founders.

Al ElliottI'll get a pencil and take some notes. If you have support tickets in your business, then this is going to sound frighteningly familiar. You open the queue on Monday morning, 200 You open up tickets before even the first sip of coffee and you already know what's in there. Password reset requests, order updates, the same questions over and over again. Hey, what if that part of the job just handled itself?

Leanne ElliottHubSpot Customer Agent resolves those repeat tickets using your actual CRM data and knowledge base so your team can focus on the conversations that actually need them and your customers get answers faster.

Al ElliottCheck out hubspot.com, the agentic customer platform for growing businesses.

D — REVIEWMy name's Matthew Hook. I am a co-founder with Caroline of Look Up, which is a storytelling consultancy, and I am a strategist of various strokes over the last 25 years. But my obsession is story as a way of helping people get clarity about big problems. That's what I care about the most.

Caroline KeylockAnd I'm Caroline Keylock, so obviously also co-founder of Look Up. I particularly specialize in the role of story when it comes to brand and culture, and particularly in lifestyle industries. So my background is very much in areas like news and magazines and fashion, beauty, the fun stuff, I like to say.

Al ElliottCan we start off at the very beginning? So when we first spoke, we talked about, I think we called it the founder story trap or something similar to this. Matthew, could you tell us what that means and what it actually does to a business?

D — REVIEWYeah, I think when you're at the start of a business, your story as a founder can be unbelievably powerful because for all the people you are speaking to, you're massively overloaded. Everything's really complicated. Everything kind of looks the same. And it's the founder's story that helps you lock into the idea of a business and why it's unique and why it's interesting and why it's different. So it's such a powerful asset. I mean, if you think you're an investor and you see literally an almost infinite number of pitches, thousands and thousands, how do you stand out from that? Often it's a human being and their story. Or if you're like a big customer, like a retailer, and you're trying to work out why on earth should I stock this in store? Again, almost infinitely oversupplied with options, and it's someone's story that kind of slips past you. So in those early days, it's such a powerful asset. And Caroline and I were recently at Ideas Fest and we heard the story of the Black Farmer, which is Wilfred Emmanuel Jones, and how he used to use his personality, his style, his backstory to suddenly get taken seriously as a relatively small-scale farmer by great big retailers. So it's an amazing asset in those early days, helps you sneak past people's guards, stand out from the crowd, and it gets you started. Because it gets you started in such a powerful way, the danger is that you can end up being trapped inside it. And you don't realize that over time, having your whole business leaning on a single person's story, experiences, style can become increasingly frustrating or can pen you in over time. And we should explore some of the different angles and ways in which that's done. But generally you reach a point and you don't necessarily notice that point where it's beginning to constrain you a little bit. It's constraining your team. It works well in some occasions, not other occasions. And spotting that is really difficult and knowing what to do about it before it's a massive difficulty. That's the trap. And like most traps, you don't quite know you're in it until suddenly you realize, oh, it's too late. I should have been thinking about this for a while. So that's what informs a lot of our work with scale-up businesses, particularly with those founders who have recognized the story that got me here won't necessarily get us there. And I need to get ahead of that feeling of that story not being enough. And, uh, yeah, make sure the business has the opportunity to scale and grow.

Al ElliottSome of the most famous ideas of these, these founder stories are like Dragon's Den, for example. Like, that's the entire idea, isn't it? You stand up there and you tell your story. I, what I don't quite understand is at what point would that story not be helping me anymore? What are the signs of that?

D — REVIEWIt's not so much that it's not helpful at all. It's that when you realize the whole edifice is leaning on one thing. And because that story, whether it's the Dragon's Den story or the VC funding story, those are situations in which that absolutely 100% is for most businesses, their crucial asset, because people are going for super high-risk investment. They're looking for the one thing that makes them believe in it, and that thing is a person. So in that environment, it so often is the differentiator. I think what you realize is as a business scales and grows, you hit a few key challenges and they can play out in different ways. One that I'm particularly obsessed with is for any business to really scale, at some point you've gotta have much, much bigger customers or a much, much wider variety of audiences. And it may be some of those new audiences you need to connect to are not so invested in, so interested in the founder stories. So for example, if you're in the world of technology and suddenly you're building technology that a big business is gonna be leaning and relying on, they're gonna be asking lots of more institutional questions. And the story of where the business came from, Might be a really interesting kind of inciting incident to explain where did we start and how did we get here? But you can't have the fundamental reliability or trust in that product leaning on that one person and their vision and their story. It's gotta be something bigger than that.

Caroline KeylockYeah, 'cause I think particularly some industries rely on a founder story more than others. So, you know, I work a lot in the wellness space, for example, and in that space, quite often the founder becomes the representation of the end target audience. So, when they're going and speaking either to end customers or investors, they are literally the depiction of who they're targeting. And there's a lot of credibility that comes with that. But if you can't move beyond that, they are suddenly then the person demanded in every investor scenario, every marketing scenario, every time where you want a face of the brand. And if you go to other countries and you're scaling there, suddenly you've just got this point where a founder literally can't be everywhere at once. There has to be a point at which they can hand over the story. To some degree. And you see that so much in the wellness industries where you do have these really inspiring, often female founders, and they are this amazing depiction of the brand, but they're so stressed out. They are the opposite to the wellness industry and everything it's standing for because they just can't be everywhere all at once. And so, they become the bottleneck for absolutely everything because what they haven't done is said, how does it grow beyond me? And what does it mean for other people to own this story?

Al ElliottSo if we look at the likes of Levi Roots and his sauce and Richard Branson, then I think some listeners will be going, well, hang on a minute, they are still the person. So how does it work for them? Because they've got massive organizations.

D — REVIEWI think what you see in those cases is what you are looking at is not just an individual looking at a brand. And so they haven't created organizations where Richard Branson has got to make every single decision. about what you do operationally or have every single conversation with a partner or a supplier because you've got the essence of what that person means. Really what you are looking at is Virgin, and Richard Branson is one of the really, really useful assets that you use to express Virginness. But everyone knows what Virginness is. They haven't created a bottleneck where if Richard Branson's not in the room, you can't sell. And I know it sounds crazy, but there are a lot of founder businesses Where you reach a point where no one feels confident unless that founder is in the room. So it doesn't necessarily show up as the story itself not landing, but it does show up as these businesses which end up overloaded and bottlenecked. So you can't make key product decisions unless the founder's there. You can't land a sale unless the founder is there. The founder themselves is just running around tearing their hair out because they can't cover everything. And just the reality is building any business of scale, That story of the founder has to turn into a way of operating, a brand story that operates when they're not there and that other people can input into and drive with their skill and their capability.

Caroline KeylockI think there is a really simple articulation of this. So I saw a founder I know the other day, she was talking on LinkedIn. She's someone who's been on Dragon's Den. So she's been through that journey of telling her story, You know, her business is very much her. She's 10 years into the journey, and she said, for the first time, I'm going to call myself the CEO of the organization, not the founder of the organization. So, in itself, that is a story to her teams that says, my role needs to change. You have a different role. I'm gonna step away a little bit. Mm-hmm. You know, you're no longer like the heart of it, but there's a very particular role that you play. And not enough founders think about that journey ahead of time. So, actually thinking ahead of time, what role will I play in 5 years, 10 years, all being well, would really change the trajectory of how you thought about the story and the operational side of the organisation. But we're in it, right? We're in it as founders, and we're caught up in the day-to-day. So, it's quite hard to think strategically like that about what does it look like without me?

Leanne ElliottWhat impact have you seen this have on the rest of the team? What does it feel like for a manager in that organization working under a founder like that?

D — REVIEWWhat's very common in founder businesses that reach this kind of stage is that suddenly things feel very, very hectic and very, very busy. And I think often people misascribe that to going, oh, this is because we don't have XYZ process technology, we need more teams, et cetera, et cetera. And actually what they're actually realizing is that sense of frustration that comes from not really being able to make decisions. So because they're deferring to a kind of person-led decision-making process, this often coincides with people not having a bit more of a framework to go, if I'm in this situation, I've got 3 things on my plate, I see another 2 things I should be doing, I should drop 2 things and move to— which is what in most businesses you would have that kind of prioritization process. In a founder-led business, often people feel like they have to do everything. that they've always done and, and, and, and they don't necessarily have somewhere to go to say, well, how do I prioritize? Because the answer is, I'll have to go and ask the founder. And then you're in a queue of 30 people all bringing their small-scale problems to the founder. So definitely hecticness is a symptom of this. And I think those businesses transitioning through that just feel more crazy and more hectic, and it's more impossible to prioritize than elsewhere. I think the other thing is all great people in any role, in any job, love to have a feeling of agency, of motivation that comes from using your skills and your capabilities, making decisions, feeling like you're pushing things forward. And the danger is in a very founder-dominated business, people just don't feel they can take that leap, and that's not good for them and obviously not good for the founder either.

Caroline KeylockI think the part that gets underestimated here, because these could all sound like operational issues, right? And if any founders are listening to this, they're like, Well, this is what happens with scaling. You know, it's busy, it's a bit hectic. We are trying to make what was a small tight team work on a larger scale. It's the role of story within that, I guess, is what we are trying to talk about here, because a story is where the business is going. A story is what binds the culture of the business and keeps people feeling like that business is the same kind of business as it scales. A story is what enables other people to go and win new business for you. Beyond the founder. You know, a story is central to all of these stages, and that's what needs to move beyond the founder. And I think sometimes they will look at all of the operational processes and think, well, I need a CMO now. I need someone to go and do sales now. You know, it's quite functional. But if they don't do the story bit accompanying it, they never really truly hand over. And that's where all of this starts to become a real issue and where there's friction.

Leanne ElliottI'm curious, like you say, it's about a story, and my psychologist's spidey sense is going, Interesting. I'm thinking a lot of founders and entrepreneurs, including my wonderful husband and co-host, there is at times an element of main character energy that you have to have as a founder. And, you know, a little bit of ego, maybe. You need a healthy dose of narcissism to believe that you can, you know, do, create, you know, achieve such a feat. So, I guess I'm wondering, whilst of course being careful to the The wonderful clients that you work with. Is that something you see that some founders maybe need a bit more convincing that they don't necessarily have to be the centre of the story?

D — REVIEWI think that's absolutely, definitely true, that you need that level of bravado and confidence and self-reliance to get you through those early stages. Absolutely, you have to. And it still continues to be an asset for a long time afterwards. In reality, we're not saying it's not an asset. It's a huge asset. I think it's more a journey of transforming how you think about the way you create value. So it doesn't have to be a diminishing of ego in that sense, but it's just an understanding. If I want to do the really, really big stuff, which is what a lot of founders want to do, they want to do something really, really big. It's about transforming from the story of me and how I got here and what I'd like to achieve to that bigger story that says, Here's the future I'm trying to create. Here's the kind of culture that I'd like to develop. And here's the way that I'd like to go and sell this to the world. And it's just that transition to make that less dependent on the biography of your own life, how you behave when you're in a room, and more to a set of principles that you believe in. And also to retain the flexibility to go, yes, I may believe that I'm the main character, but there's a lot of other characters in this story too along the way. I've built my team, a team I believe in. I must have learned from that team, and therefore it increasingly becomes our story, not just my story. I've learned from my failures and my successes. That helps me to learn what does the market really need? What does the market not really need? And all of those things point you in a similar direction, which is I am an asset to my business. I have an understanding of it no one else will ever have. I have some great stories, which if I pull them out at the right moment, are going to make a really big difference to my business. But the business doesn't exist to be a projection of my own life story.

Caroline KeylockI think founders have got a bad reputation, right, in many circles because of main character energy. And as Matthew said, it's a hard thing. You've literally born a baby in so many ways. And so it is a hard thing to say, how do I distance myself from that and let that baby start to walk and start to run and start to become their own little human being. And I think that's a really tough thing to do. But I think where the founders have realized there is opportunity for it to grow beyond them, that's when teams have a fantastic relationship with the founder, and they work hand in hand. They're all aligned behind the same vision and goals. When you hear these stories in industries, and you do hear them, of that founder was a nightmare, that founder was just really hard work, that founder was phoning me up at 5 in the morning because They expect everything to be as important to them, to me, as it is to them. It's because that work hasn't happened to think, how does the story move beyond me? And it needs to, because otherwise you're always gonna have that friction with that next level of team.

Al ElliottThis makes so much sense. And I think that to paraphrase, I think it was George Bernard Shaw who said, reasonable men ask why, unreasonable men ask why not. That's why the future of the world depends on Now, apologies for the genderization there. Obviously, that's—

Leanne ElliottA quote of its time. Obviously. Yes.

Al ElliottWe'll let you off. Exactly. So, there has to be an element of being unreasonable in the first place to be a founder. What are your thoughts?

Caroline Keylock100% true. 100% true. You have to have absolute blind faith in your idea to start. And so, I think, you know, that is unreasonable to most people because you're either creating something entirely new or believing that you can go up against existing competition, you have to have that blind faith. But the successful ones do understand that it takes other experts, other people, people with skill sets beyond their own. And that requires transition, and that requires trust, and that requires partnership. And all of those things require some communication of your original reason for starting something to become their reason for being there. And their reason for continuing to be there. And that's the transition of story. So, that unreasonableness has to shift at some point. I'm sure Richard Branson understands that other people have their own story about Virgin that isn't just his origin story, right? Their reason for being there, the values it has, the things that it's trying to do in the world. I'm sure he doesn't think it's all about his origin story still.

Al ElliottSo, there are gonna be founders you work with who have started off main character energy. They're like, yeah, we can do anything. And look what we've created. And now you are having to say to them, Yeah, you're gonna have to give some of this away and get other people to start working on the stuff that you used to work on. What does that look like? How do you, what do people want, not want to give up? What do they easily give up?

Caroline KeylockI think it's less thinking about it as giving up and more moving forward because as Matthew said before, that founder story will still have a role in the brand in some way, shape, or form. It should still be the pillar of the brand, even if it's to investors. Even if it's in the circles of founders, which increasingly is a part of scale-ups marketing. Just how amazing is the founder? What's the journey that they're going on is a pillar of their storytelling. But if I take an example of a beauty tech brand that I've worked with a number of times, and they're very successful in market, when the organisation started, it was very much the founder's story. She had been very sick. She had found a solution to feeling that way. She had taken that solution to market, and it was incredibly successful. But it was never gonna be the end of that business. And they've moved into other categories and they've moved into other markets. And she totally understood that to do that, that origin story didn't make sense to explain the totality of that brand offering anymore. It would be rooting it in something that was slightly relevant, but not the totality of why those products came to market. So, as they've gone into that, there has to be that stage of, well, Why does this product exist? What's the market it exists in? What's the USP? All of those traditional things that we do in marketing when we do positioning of products. But beyond that, also, oh, I'm going to need a bigger team. I'm going to need teams that exist in markets where I don't see them and speak to them more than once a week. How am I going to translate why I started this business to them? So, I think if you can position it to founders less as, You're gonna have to give this up, and more as your role is going to change and people are going to need to know how to do a brilliant job on your behalf. And you therefore need to give them a story that comes from your brain and allow them to evolve it, allow them to make it their own. It's not giving up, it's evolving, it's achieving their goals. It's everything that they probably wanted when they started the business. And I think just getting them to go through that transition Yeah, sometimes, of course, it can be a challenge because people feel like they're always going to be the best person to tell that story. And odds on, they will be to some degree because it's theirs. But I think getting them to understand that that is the way to grow is normally a pretty quick route to getting them to understand it's something that needs to happen.

Leanne ElliottCan we dig into that a little bit more then, in terms of this transition from founder to team? Is there maybe an example you can give us of a founder who's manage that transition. So, they're using their profile to spotlight the team rather than themselves.

Caroline KeylockI think an excellent brand example, and then one of my favourite brands, is Finisterre. And they have a phenomenal founder. You know, Tom Kay spotted this opportunity sitting on his surfboard in the sea, in the cold waters of Cornwall, and thinking, the entire surf market of brands does not speak to this scenario where I'm sitting here with my hood and my gloves and my boots and everything else. It's speaking to California. And he started a brand on that premise. And that premise still exists today. It's the core of that brand is that they are for cold water surfers, swimmers, and everyone who kind of exists around that space. But I think he spotted really early on that the values that that brand had were what was actually really instrumental to people buying into it. So not only did it understand the scenario of use, but they've always been incredibly sustainable. They've always sought out new materials. They've always existed in spaces and places that those communities come together. And have built themselves as a community brand. And I would say now they've really recognized that their storytellers are multiple. And I'm really talking multi-layered. So everyone from the CMO for the brand has a real profile as a storyteller. The people who design the knitwear and the technical side of the brand, they're storytellers. The ambassadors for the brand are storytellers. Individuals in the team, when they come together for away days and their away days happen to be in the sea, They're storytellers. Their partners, like the RNLI, they've recently come to the fore behind them. They're storytellers. So, the essence of the brand is exactly the same as when he started it. And I'm sure he's incredibly proud that that hasn't really shifted. But in reality, so many people now own that story. So, if he did walk away, if something, heaven forbid, Tom, happened to him, that brand would still be a phenomenal brand. It doesn't depend on him. And I think that that's the transition. And that's what you're really buying into as a founder when you're handing the story over is the longevity of your business beyond you. And planning for that can only make you more sustainable over time.

Al ElliottQuick announcement for all listeners. Yeah, I've got a, I've got a new toy on my, on my little deck thing so I can make my voice change. Anyway, sorry, Leanne.

Leanne ElliottI love it. Do it again.

Al ElliottHello, Leanne.

Leanne ElliottWhoa! Do another one. Hello. But we didn't interrupt your podcast listening for, uh, for this. We actually interrupted it to tell you about one of our new favorite podcasts. It's called Success Story. It is hosted by Scott D. Clary, and it is brought to you by the HubSpot Podcast Network, the audio destination for business professionals. Success Story features question and answer sessions and conversations on sales, marketing, business startups, and entrepreneurship.

Al ElliottOh, and if you like this podcast, then I think you'll love Scott's episode back in December where the infamous Seth Godin talks about empowering employees. So go listen to Success Stories wherever you get your podcasts. What happens when the founder tells too good a story? So I'm thinking about WeWork, right? So I watched the, uh, the WeWork thing and the guy, I mean, I don't know whether he's, he's a, Whether I wanna be him or I just never wanna be anything like him. He could, he told these stories that were so incredible that everyone went, this is amazing, but it just all collapsed. So what happens when, if you are working in a company where the founder is a bit more Adam Neumann and he's, it's, it's not based in reality?

D — REVIEWWell, I think the first thing is that's a very practical example of why it's so dangerous to build something, all of which is leaning on an individual person. Because Adam Neumann, he's a very, very extreme character and God forbid I should ever find myself in that situation. But any individual, any human being is flawed. We're going to have periods of time where we get things wrong, maybe when we are sick, maybe where we just made a bad choice, maybe we are just tired. And it is unfair, I think, to start with on a whole massive organization to lean everything right on the head of an individual. It's unfair to the individual and it's unfair to the group. Yeah. I think in that kind of example, the example you gave, that's often a certain kind of individual. And I think this is, without attacking any individuals, this is where the ego can be dangerous because there's a certain personality that is very, very convinced of their fundamental rightness, of their fundamental genius. And I think you see this right now. There's a quote this week. I'm going to go straight in there. Where it was a quote from Sam Altman I was reading, and he was describing how businesses in the first, like great founders, of which he's obviously including himself in that category, don't necessarily think about founding businesses. They think about founding religions, and a business is something you found along the way. Now, there's some wisdom in that, in that in some respects he's describing some of the things that Caroline and I did describing, which is Businesses need to be built on sets of beliefs that take you somewhere beyond the— I believe that. I think that's reasonable. When you hear that described as a religion, that takes you into a very, very awkward space because you are saying there is an orthodoxy. That orthodoxy is my orthodoxy. That orthodoxy should not be questioned by anyone. Anyone who does question it is, what's the word, is an apostate or is walked from the path of righteousness. And I think that's a little bit what can creep in. I think particularly it happens in the world of technology and maybe in a certain kind of VC-funded, fueled kind of tech bubble type world. But the danger that you become so convinced as each of your decisions appears to turn out right, you become convinced that every thought you've ever had in your head therefore must be right. And you carry this bubble of rightness around with you. And I think to an extent, back to the earlier questions that we were talking about, kind of ego, allowing that bubble to be pricked has got to be a fundamental thing ultimately to being a really successful founder.

Caroline KeylockI think there is something about the role of the founder story though, and the strength that it can play, because to some degree, especially as the founder has more people around them and a good senior leadership team supporting them, the founder's role should shift to being a little bit ahead. In terms of the story, where is the market going? Where could we go? Like, what's our bigger potential? What's the big vision? Them having clarity on that, even if everyone else sometimes questions it, sometimes worries about it, to some degree is a good role for a founder to have because those people do have an unreasonable quality to them. They do see the world differently. They can perhaps see opportunities where everyone else would have skepticism. But that works as long as you've got a really good story for the now, a really good story that is supported by operations and a great leadership team of the potential of the now, of where the numbers are going to come in next week, next month, of what your customers actually need to hear from you versus what investors need to hear from you. And I think that is the fundamental difference at play, that there should be a point where a founder's greatest asset is the ability to sell in the next round of investment, And selling the opportunity of the future whilst his team are selling a story on the ground. If you can't tell the difference between the two, I think that's where it gets incredibly tricky.

Leanne ElliottSo, I feel like it's a really difficult balance to get right when it comes to taking the personal ethos of the founder and turning that into more shared principles and values that everyone can use. So, practically speaking, how do you do that? And what does that first draft look like?

Caroline KeylockI think one of the biggest things, and where we see this fail, perhaps we start with, is when people have defined values of an organization, the vision of the organization, all the normal trappings of these kinds of documents, and they haven't really consulted. So, it's theirs, or maybe 3 people on the leadership team who have defined that. And then it's launched to everyone. Maybe it's launched in a fantastic way, but ultimately it probably ends up sitting in a document somewhere. And that's not necessarily representative of what it looks like on the ground for people day to day. And people don't feel consulted. And sometimes in organizations, it's the 5th one they've seen in the last 2 years. So, there's a healthy dose of skepticism about, oh, another set of new values, another set of visions, et cetera. So, I think the consultation and the collaboration that should be involved in creating a story of an organization is crucial when you get to a certain size. And actually, things don't fail because they're written down and they exist in a document. They fail because it wasn't collaborative in getting there, and it doesn't match the day-to-day experience of people in the organization.

Al ElliottHow do you work out what parts of the founder story gets moved on to the next transition and the next story that he's creating and what gets left out and what, and are founders not gonna be pushing back going, no, this was, this is why we started our surf company was because I was sitting on my backside and, you know, how do you do that? How do you, how do you decide what stays in, what goes out?

D — REVIEWSo one answer that I have to that is that if you actually look at any really successful, thriving, scaled company, they will have some version of Here's where we started. And often the here's where we started will include the story of a founder or of the community that the founder was in. The reality is that storytelling is endless rewriting. And those versions that you read from those companies, they are probably a 3rd or 4th rewriting of that origin story, by which I don't mean that they're not true, but that if we ourselves in our own experience look back on incidents from our life, They should look different with the vantage point of 3 years later, 5 years later, 10 years later. So it's not about ripping the founder story out or the origin story out. Origin stories are so invaluable as a point of truth for people to go back to. The question is to, with a mature and sensible mind, keep relooking at that story and go, what aspect of that would we bring out now? Rather than to keep robotically retelling the same story in the same words that says, one day I was walking down the road and I saw this thing and it made me think of this. But to instead go, okay, that incident from my life, that's acquiring more and different meaning as time goes on. As more people have become part of this story, how do I think about that differently? So I think a really mature founder that has all of that necessary ego and drive but also has that perspective on themselves and how the idea they've nurtured is growing, would keep naturally going back and retelling that story and thinking, how and why is that relevant now? I mean, I'm sure the version, we talked about Richard Branson earlier, the version of Richard Branson that started out was just about how angry a kind of young entrepreneurial hippie was with record companies and what they were doing to music. That's not the Virgin story now. It's the same DNA as that story, but when you are telling stories about airlines, you're not telling stories about record companies. Richard Branson has endlessly retold that story and gone, well, what does this mean now? Like the essence of it is still the same. I'm a bit of a pirate, I'm a challenger to the establishment, but what version would I tell of that story now? So I would never throw away the founder story, but I think just it's constantly reflecting on where are we now? What element of that is most useful? Yeah. And also just on reflection, knowing who we are now and what we wanna be next, what is the meaning in that story? It's probably different to what it felt like 6 months after that story had happened. And I was desperately trying to get my first listing in a retailer. Now that I'm a global mega company, the way I feel about that story is probably different.

Caroline KeylockStorytelling is always picking what you say and what you don't say, right? Like editing is possibly the most important part of any story. And if I went back to that beauty tech example that I gave earlier, You know, at the beginning, that story was all about she was sick, there was a cure, and then they launched that product, and that other people could have, you know, their best version of themselves as well through taking that product. Now that there are other products and they've disrupted other categories, the bit that they've taken out of that story is her recognition that there were often solutions in health that the everyday person just didn't get access to, and they wanted to go on and disrupt with that thought into other categories. So, it is still connected to her origin story. Yeah. But it's more the innovation quality and the kind of pulling the curtain back on certain industries element that gets played out. And that's what everything's reinforced behind when you see any stories about her now. But it means that those products and categories have strong stories of their own, of innovation and disruption that don't rely on her story. And I think that's the point. It's, does it still rely on it or can it stand on its own and the founder story be complementary? And that's really where you want to be as you scale. You want to have scaled the story to the degree that the founder story is a brilliant bonus on top, but it doesn't have to be there as the foundations of the business.

Leanne ElliottI imagine we've got lots of business owners listening who are on board, who are getting it absolutely, the story needs to evolve. But how do I really decide what to prioritise when everything feels core to Well, to who I am as a founder. So, I'm guessing, I'm wondering if we can use examples. We founded Truth, Lies and Work because I was really frustrated with quiet quitting going viral and putting the emphasis on individual fault. So, that was kind of the origin of Truth, Lies and Work. So, me being angry at the injustice of the world was probably one of the pillars that started it. How does that, what questions could I ask myself? Yeah. Now, or what questions do you ask of your client to help me reflect on what I need to prioritize, both in terms of where the business currently is and where I want it to go in terms of its growth and the story supporting that?

Caroline KeylockI think one of the things we spend a lot of time on is the future story of the business. And when we say the future story, not just, you know, I've got a vision for my podcast to be the number one business podcast In the world, et cetera. But what does that look like? What does that feel like? What will every day be like? What will the team be like? You know, like really bringing color to it. And I think if you can get to that and have a much better understanding of the destination, you can then go back and reconsider your story and just think, well, what parts of that make sense in that world? Like, if I was still talking about all of that, would that feel like a diversion from that future story? Or would it feel like they go hand in hand? And that's a really quick exercise to do actually, but you can immediately see, well, at this point, maybe the injustice isn't the thing anymore, but maybe what is really interesting is just a totally different perspective on the business world. And maybe that's the bit that I would bring out more about my current story as we get bigger and bigger. And I think just connecting the two is the bit that we don't always spend a lot of time doing. We kind of do one or the other, but it's what is the messy middle? What's the connective thread that gets us from here to there? Yeah. And how will the story aid us is the exercise.

Leanne ElliottSo, what you're saying, Caroline, is that to think about this in an effective way, rather than focusing on the metrics, so how many downloads we want or what chart positions you want, or for a founder, how much revenue they wanna generate, it's actually thinking about where do we want our service and product to be? What impact is it having and how does that feel? And then working backwards.

Caroline KeylockIt's quite a qualitative approach to it. And I think sometimes as founders, that feels really uncomfortable because we want numbers and a plan and all of those kind of things. But, you know, a big part of the thinking that we have when it comes to the future story of an organisation is as much about what will you not be doing as it is about what will you be doing. And as founders, we are additive, right? We love a new plan, a new launch, a new thing. Yeah. But we're not very good at saying, well, if I'm doing that new thing, what can I no longer do? And the same applies to your story. If you are going out and selling a vision of this business in this new world, what can you imagine the sales pitch being? What are you saying is your USP at the time? And then looking back at your story in light of that, it's quite a soft side of it, it seems, I think, to founders, but it's not soft because it's the thing that's actually going to get you commercial wins is your ability always to tell your story. Yeah. So, I think spending some time on that and really thinking, how do we make that transition then? Like, what's going to have to happen to allow us to get to that point? That's where the really big strategic work happens.

Al ElliottAssuming that we have done this, so we've, right, okay, right, the founder's now gone, right, I understand. Yep, the story's gonna be less about me and more about what the company is. What does the founder do then? And is there an example of someone who's actually had the grace and the ability to step back and allow the story to have a life of its own.

D — REVIEWEasiest to think about the mega examples. I'll touch on those quickly and then maybe we'll move into some more helpful territory for founders. But when you have all the resources and infrastructure and great advice of a mega company, if you're doing things right, you should be able to do this well. So you'd look at the Microsofts of the world, which to all intents and purposes, It was Bill Gates Incorporated for a long, long time. He had a very long transition plan supported by mega resources, loads of brilliant succession. So the answers to this in the corporate world are storytelling and PR management, succession planning, operational, blah, blah, blah, blah, blah, all of that kind of stuff. And there's loads of great examples of people who've done that. Some people who've failed. I think what that shows is that if you have a huge amount of intent, And put a huge amount of action in, you can prepare for a business that survives and thrives after you. I think the trick is how do you do that? Or how do you provide that kind of intent when you're in a more realistic world where your resources are smaller? And then you have to, I think, do some things that feel quite counterintuitive. So I'm going to give an example of someone I'm working with now. I'll be vague enough that they don't feel called out on the podcast. But I thought this is really powerful. A founder of a business who really is the business's most powerful storyteller, really is the product leader and the marketing leader, drives all of the growth, but who is thinking, I need to get this business to a point where I can do the things that only I can do, which are things like talking to investors, as Caroline said, seeing round corners, predicting the future. But I need to enable my team of my management team, my co-founders, the people around me to step into these leadership roles that I keep stepping into. And in order to do that, I'm going to give them the support for each one of them to imagine, well, what if you were the person who's in the spotlight? What if you were the person who had to lead every big pitch or every company meeting? What story would you be telling if you had been the person who was the figurehead of the business? And giving them the time and the support. both emotional and practical to go away and do that. That's a very, very proactive thing to do and is a difficult plaster to rip off if you are used to being that person to put that in practically. But you've got to take these very, very proactive steps. And you've also got to have a clear idea of what does stepping back mean? Sometimes people just treat this very, very informally. And what they mean is, I'm going to try not to fiddle too much, but I'm still the CEO, I'm still the boss, I'm still in the office, I'm still around the corner. Yeah. But you guys get on with it, rather than thinking, actually, we need some more clear-cut definitional roles where people say, look, I am now going to be the chair and I'm only going to have these interactions with you, or I'm going to only be in this specific domain of innovation. And I want you all to know that you can tell me that I can't have budget if the budget isn't there. But you've got to be very intentional and very specific and clinical about that because So much has built up in terms of your equity, your hard power, your soft power. It's not something that just happens by a process of osmosis. You've got to take a point at saying, this is my role now. This is your role. I'm going to invest in you. I'm going to support you. I'm not going to call you out when you say something that isn't quite what I would've said. I'm not going to correct your emails. I'm not going to change your budgets. You've got to really, really commit to that. You've got to really plan for it. You've got to put effort into it. You've got to do everything you can to suppress your ego, as we talked about before, and to constantly make yourself the servant of that team that's taking over, all those individuals that are taking over, not the person who steps in every now and again when you think things have gone wrong. But so I think it's a really intentional process.

Caroline KeylockWe saw an excellent founder at Ideas Fest actually, who spoke on a panel, and he was the founder of a very big tech Intelligence organization, huge. And he said that he said to his senior team every year, every year I'm gonna have a particular point in the business calendar where I'm going to reconsider whether I should still be the CEO of this business, whether I'm the right person to continue to lead the business, or whether someone else should come in and I should have a slightly different role. And every year he transparently went through that process with them. You know, assessing the next stage of growth, everything they were trying to achieve. And then in a certain year, he stepped back and he didn't step away from the business. He actually went into like a head of innovation role. And for his investors' benefit, he was still like chairman of the business. So, he wasn't stepping away, but, you know, it was very clear that he felt everyone needed to buy into the story of him as a leader and that at a certain point, someone else would be. the better leader for the next stage of the business. And we just thought that was amazing. Like, why doesn't that happen more often? Because it makes such good sense. But planning ahead and bringing your team on the journey in that way, that's all storytelling, isn't it? It's actually saying to them, there'll be a point where I entrust this to you, and I will lean on what I am best at. And that is phenomenally grown up as a founder, I think, to know that there will be a stage where it outgrows you.

Al ElliottSo, I think most founders want an exit. So, really briefly, Caroline, most founders want an exit. At what point should they be writing themselves completely out of the story, or should they not?

Caroline KeylockI don't think it's a case of writing themselves out of the story. And I think hopefully we've got that across in this interview, in that there will always be a role for that founder story, but it's very early on, actually. I think they should be thinking, How will I get to the point where I am not an essential component of the story? I am a beneficial layer to that story whilst I'm here. Because if there's any point, and Matthew, you can talk to this a little bit more from being the other side of the table and looking at investment opportunities, et cetera. If there's any point where an investor looks at a business and thinks it can't survive without that founder, And that will happen if the founder's story is the only story the business can tell. That is not going to be seen as a good investment. So, if they are thinking exit, you've got to be thinking early, how do I think, what does this look like beyond me? How do I benefit it, but how does it not depend on me?

D — REVIEWYeah, my background in this is I used to be just a part of a group that were evaluating acquisitions and then working on the integration process for acquisitions. So, The opposite side of the table for us were entrepreneurs, and they were entrepreneurs in the space of digital marketing agencies, data companies, all of which naturally are very personality-driven and personally driven companies. That's just the reality of the sector. But obviously your absolute paranoia in that situation as the person acquiring is the magic word concentration. Anything when you are buying an asset where concentration is too much in a small number of client relationships. Because, you know, if you run a business and 50% of the business is one client relationship, you know that's a person-to-person relationship ultimately. And that therefore, if that relationship disappears, if that person disappears, the relationship disappears. If the relationship disappears, the business disappears. Or concentration might be Concentration of reputation. If the reputation is built on the reputation of that person rather than a methodology or a set of IP that they've codified, the asset that you're buying is diminishing the moment that you are buying it. So all of these issues of concentration, of reliance on a person or a set of people, in fact, these are all considerations, A, as to whether you will or won't buy a business, and absolutely what level of multiple that you're going to pay for it. Because you are looking for a business. The fact that it's been founded by a great founder is a huge asset because it makes you believe that there's a great idea behind the business. But you are looking for a business where that founder has already started thinking 5 to 10 years before, how do I create an operating system that makes all of my ideas come to life on a much bigger canvas than I could ever make them happening? How do I create a reputation and a brand that codifies all the things I believe and I learn? But could be dropped into another market in the middle of nowhere without me even visiting that market, and it would be meaningful and it would be useful. And as an acquirer and also as an investor, these are the things that you're looking for. You're looking for a business that is scalable, and concentration on a founder is the single thing most likely to diminish your sense of scalability in a business. So you have to imagine, could I imagine this business being 10 times as big And not having the founder in it and still being special and brilliant. And you cannot get to that by frantically rewriting your investor deck 6 months before to make it look like you're not that important. Like a serious investor or a serious acquirer can smell that, knows it, and will know, have you built a vision of the future? Have you built a culture? Have you built a scalable model? Have you built a brilliant sell for your customers? That is not me incorporated, because that's not a scalable idea.

Leanne ElliottI guess I'd love to know, Caroline, if there's a founder listening that thinks, I need to start transitioning my story, is there one thing they could do today that would really help with that?

Caroline KeylockI think to sit and sketch out the answer to the question that is, what would it take to have my business exist without me? is actually a really good first question, and they may never want to get there. You know, there's a lot of founders who don't want to exit and want to continue, but I think it starts to give you a really good steer of where your gaps are. You know, do you have a really strong story for the product, brand, service, whatever it is, that isn't dependent on you? Do you have a story that your senior leadership are able to tell? Do you have layers of storytellers who would easily be able to tell your story for you? Even if they don't know your founding story. And I think even that first exercise will quickly illuminate some gaps for you to be able to scale effectively. And it wouldn't take you very long, but I think you might realize really quickly, wow, we are more dependent on my story than I even realized because I'm so used to telling it and I'm so used to it being at the core of the brand and everyone buying into that when they come and work for me. But actually, if you can plan for it being obsolete, or as we've said, a lovely addition, then that is a really good way to think about the operational side of scaling your business as well, because the two should really be going hand in hand.

Al ElliottThat was Matthew Hook and Caroline Keylock, and I've got a few uncomfortable things to think about this weekend. Thanks, guys.

Leanne ElliottLet's wrap up with our top 3 takeaways for leaders. Number 1, a business that depends on one person's story is worth less. Matthew has been on the buying side. The thing investors and acquirers fear most is concentration. If the business can't run without you, they will pay less for it.

Al ElliottYeah. And lesson 2, sketch what it would take for your business to exist without you. Caroline says to do it this week. Do you have a story your senior team can tell? Do you have layers of storytellers? You'll find the gaps in minutes, I promise you.

Leanne ElliottLesson 3, build the story with your team. Don't launch it at them. Values fail because people weren't consulted and the document doesn't match daily life. Give the story many owners.

Al ElliottWhich brings us back to the title nicely. Values don't spread, stories do, but only when more than one person is telling them.

Leanne ElliottYou can find Matthew and Caroline at wearelookup.com. Their Substack is there too, and all the links are in the show notes.

Al ElliottThat's all for today. Thank you so much, Ellie. for introducing us to these amazing guys. This is Truth, Lies and Work. We'll see you on Tuesday. Bye.