E372 | Oliver Cummings: left Goldman Sachs for a 4-person startup. built a 60,000 expert network

In this interview, Oliver Cummings, CEO of NuRole and host of the Enter the Boardroom podcast, recounts his move from a decade‑long career in private equity at Goldman Sachs Capital Partners and BXR Partners to co‑founding a four‑person startup that has grown into a 60‑person company with a 60,000‑strong board‑member network. He explains the motivations behind leaving a stable PE role – a mix of regret‑minimisation, family pressure, and a belief that better boards create better companies. Cummings describes NuRole’s dual‑sided business model: a board‑search service (subscription for repeat hires, pay‑per‑placement for ad‑hoc searches) and a board‑development community (annual membership guiding individuals from first board role to chair). He argues that boards matter because they provide strategic direction, accountability, and a “critical friend” that forces discipline, likening them to personal trainers. He stresses the power of compounding – both financial (£72,565.72 invested at 10 % yields a billion in 100 years) and personal (daily 1 % improvement yields ~37× growth). He shares hiring insights, noting that traditional interview intuition is weak; instead he cites Schmidt & Hunter’s research on cognitive ability tests and the importance of attitude and cultural fit. He reflects on leadership challenges: communication clarity, over‑communication of strategy, focus versus diversification, and the difficulty of firing under‑performers. He recommends three books that shaped his mindset – Growth Mindset (Carol Dweck), Drive (Dan Pink), and How Will You Measure Your Life? (Clay Christensen). He also recounts a pricing experiment where doubling price while losing half the customers left revenue unchanged, illustrating price elasticity. Finally, he outlines NuRole’s community pillars – board success, board excellence, and board networking – and how pop‑up boards, coaches, and peer groups supplement formal boards.
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In terms of your evolution, what, what took you out of private equity into startup founder?
Like, lots of people thought I was absolutely deluded. She said, look, you've always said you wanted to do something entrepreneurial. Now's your time to come prove it. I always felt like a bit of a fraud as an investor.
And how, how big was it when you joined?
They're sort of 4 people at the time, burning cash like crazy. So we just sent out our 10,000th invoice. I happen to have 60,000 board members I could call on to bounce ideas. Most people overvalue advice and undervalue accountability. The numbers do not add up. You do spend those first few years working for nothing. I find it easier to live with the oh well than the what if. And I think it took us 5 years to send out our first 1,000 invoices.
Yeah.
I was getting it wrong left, right, and center and realized that actually turns out no one's any good at hiring. So you describe it as fire insurance that only works when there's no fire.
Yeah.
£72,565.72. That is the exact amount you'd need to invest today, compounding at 10% a year, which is what historically you've got from something like the S&P 500, to be worth a billion in 100 years. Hello, I'm Oliver Cummings, CEO of NuRole, the board search specialist and host of Enter the Boardroom, the podcast exploring what makes great boards and great board members. I'm driven by a simple belief that boards matter. They shape the society we live in, and unfortunately, most boards are dysfunctional, destroying value through poor decisions rather than creating it. And that's why we built New Role, to serve 2 primary customers with a singular focus on boards. So for organisations, we have our board search and advisory team who've helped over 4,000 organisations find the best chairs, non-executive directors, trustees, advisory board members, and pop-up board members from our network of over 60,000. And for individuals, Enter the Boardroom community supports over 10,000 individuals wherever they are on their board journey, whether they are just trying to work out if the boardroom is a place for them, whether they are an executive on their board, or maybe taking on a first board role, or they've gone non-executive and they're starting to build a plural career, or even made it through to the chair role. Through our pathway programme, our board masterminds, and a network of 1,000 board-level members, we give them the resources, the connections, and the support to build and flourish in their board career. Before my new role, I spent over a decade as a private equity and growth investor with Goldman Sachs Capital Partners, and later as a partner at BXR Partners.
And I'm intrigued, 60,000 members. How many non-exec, well, how many, I guess Companies House registers those what are registered, how many directors are registered at Companies House as being board members?
So the way we think about it is, I think it's something like there are over 300,000 organizations in the UK with more than 20 employees. And so those are all organizations that I would think should have some form of challenge or support. Now, obviously, every organization has to have a board member, but typically that'll be the owners as other directors.
Yeah.
But whether they are formal, what I call fiduciary board members, or whether they are informal advisory board members who are providing that challenge or support, I think there should be well over 300,000 in the UK alone.
And how many of the 60,000 people in your network then are actively on boards?
All of them? They would all be on boards or board level and sort of suitable for boards. So they might be sort of senior execs or others aspiring to get their first board role.
Wow. And why, why, what's, why do you think that boards make a difference? You said they make a difference to society in what In what way?
So boards are responsible for the strategic direction of the organizations and for ensuring that organizations are well run. So they have all the most critical decisions effectively coming up to them and have the ability to shape those decisions. So when an organization has the choice of path A or path B, the board has the opportunity to influence which path it goes down, whether that's for better or worse.
In smaller businesses though, do you need, do you need a board? I mean, you know, Where there's no investors, why do you think a board would matter?
So you've got to think about, you know, what, what is the purpose of the board? And I think boards can serve different roles. And unfortunately, I think a lot of boards serve what are called the oversight role, which is basically making sure people aren't stealing from the company, or doing other things that they shouldn't be doing. And though there are some boards where I guess that's required, although actually, I had a very entertaining guest on Enter the Boardroom called Roger Martin, who basically says this was a complete nonsense reason for having a board, because it's what he's called the agency problem. You have someone to make sure someone else is not stealing. Well, who's making sure the person who's not, who's watching, isn't stealing? And the reality is, if you've got a crooked CEO in place, they're going to pull the wool over the eyes of the board anyway. So he described it as fire insurance that only works when there's no fire.
Yes.
Quite entertaining. But I think the more valuable role of a board, particularly in a startup environment, is the sort of the critical friend that provides challenge or support, that provides, you know, when you're especially in the early stages, but actually throughout my experience, that ability to just get you to stand back and see the wood from the trees when your head is down in the operations, that can pull kind of insights from outside your immediate area and help you see things in a different way. And also that can provide you with a sort of sense of accountability.
Yeah.
Why do I have a, you know, why does anyone need a personal trainer? We could all go along to the gym on our own. And yet most people, when left to their own devices, don't. There are a few exceptional people I know who can manage without a personal trainer, but most of us fall by the wayside. But when you have a personal trainer there who, you know, when your alarm goes off at whatever time it goes off and you think, am I going to go? Am I not going to go? When you've got that commitment to the personal trainer, to go do it, you show up. And it's kind of the same with a board. Like, actually, a lot of the value comes from the discipline that it brings in, that it forces you to put your thinking down on paper, to lay out the options that you're considering, the assumptions you're making, where you might be going wrong, and then has an external party that then sort of interrogates those and can also bring their network to bear to help you unlock problems in different ways from the ways you might have anticipated or spot holes in the road. that you might not have anticipated.
Yeah, I buy that. I think the art of writing things down, putting something in the diary monthly or quarterly, and having some commitment to an external person to even just turn up and tell them the story, and having some commitment to making the whole thing feel logical and sensible. And it's hard. Even that's hard. Yeah.
And it doesn't need to be in a formal board setting, and you can get it in lots of different ways. I work with combinations of a coach, a peer advisory group, what I call a pop-up board, where we pull together these groups of experts for a specific issue. Like, when we were trying to launch our community offering, got a whole load of people who are expert in community to come and interrogate our thinking around that in a 2-hour discussion.
Yeah.
Brilliant, because the chances of me having any real experts on community on my board are quite low, whereas suddenly being able to get 5 of them in the room together, all focused on the problem, and then at the end of that, not needing to sort of commit to them was invaluable. And then obviously the main board itself, where you have that sort of formal discipline. So I think, you know, in a startup, what you need changes over time, or what you get from each of those things is slightly different, you know, from your peer group is different from a coach, which is different from a pop-up board, which is different from the fiduciary, but they all come together to, I think, help you make better decisions.
And what is it that you think is true that other people think is nonsense, or vice versa, that things that other people think you think Total rubbish.
So a few things. I think most people don't understand the power of compounding. So if you think £72,500—
The 8th wonder of the world.
The 8th wonder of the world. So £72,565.72, that is the exact amount you'd need to invest today, compounding at 10% a year, which is what historically you've got from something like the S&P 500. to be worth a billion in 100 years. And most people haven't done it. The question is, why not? Because it's, you know, $72,000 is a significant sum, but it's within the reach of many families. And as I say, the S&P 500 has returned that roughly annually with the dividends reinvested. And so the question is, why aren't there billionaire families everywhere? Because basically no one lets compounding run. We interrupt it, we panic sell in downturns, we cash out. for a Christian extension, and we can't stomach 100 years of doing nothing. And I think that same kind of lesson of compounding in a financial sense also applies to, you know, relationships, friendships, education and learning, business decisions. And I think most people, while they might rationally and cerebrally, cerebrally understand it, don't live it in their daily actions.
I— but also, I think there's something about human evolution has meant Because it's not that compounding isn't a straight line, that compounding is exponential. You know, it's $100 grand, it's $100 million at the end. And so because, I don't know, there's something about the way our brains are wired that we only, it's really hard for us not to just think in a linear way.
It's availability bias. And Kahneman and Tversky sort of talked about this, that basically we haven't evolved to think exponentially. So one of the questions I'll often ask people At interviews, when I'm sort of talking about one of our values, core values, is be better as an organization, constantly compounding improvement. If you improve by 1% every day for a year, how many times better are you at the end of the year? Go on, I'll ask you.
I don't know, it's some ridiculous number, isn't it? I can't, I don't know, I'm afraid I don't know the answer.
But give me a guess, I'm not expecting you to know the answer. How many times?
No, but it's not 365, it's more. I don't know, it's a ridiculous number.
1% better every day. Go on, give me the number.
I don't know, 300% better.
300%. So 3 times better.
Okay.
Yeah. You've demonstrated beautifully how badly we are at thinking exponentially. And by the way, shouldn't feel bad about that because everyone always does it. It's actually, I think, 37.4 times better or something like that.
Yeah.
And we just haven't, we haven't evolved to be able to think about this sort of exactly as you articulated that the exponential impact of small gains over a long time. I had a successful founder on the podcast recently who described themselves as a tortoise versus the hare. And they started up a business about the same time as Michael Dell. It was Nick Wheeler, the founder of Charles Tyrwhitt. And, uh, you know, he said, he said he sometimes looks at himself in the mirror and feels bad because he sees Michael Dell and he's like raced ahead. But actually he's been going slowly and steadily. And he said, you know, the first 20 years of being a tortoise are very boring. And then after about 20 years, the next 20 years become rather exciting. And most people give up, you know, it's that same compounding thing. Most people give up in the first 20 years, and they fail to keep compounding. And it's something I've noticed from lots of the most successful founders I know, they sort of— one of the things they always say to me is, just keep going, you'll get there eventually. And a part of me sits there thinking, is that just like a winner's history? And all the ones who kept going and didn't get there are sort of, you know, in some hole somewhere? Or is there actually something in that, that actually that ability to just keep going, the sort of, I guess, what Annie Duke would call gritting, is just a superpower that most people might Understand rationally, but don't actually live when the rubber hits the road?
I see it quite a lot when organizations get towards about 100 people, because what people are doing is they're thinking about the amount of change that's got them to here, and they're thinking it might be the same in the future. But that whole, you know, managing a team of 12 people, when you're up to 12 people when you start, and then you put in some managers, and then when you put in that extra layer, it gets exponentially harder, and people do get stuck, and they're caught out. Or even as they look forward and they're scaling, the number of salespeople you need to hire to keep the growth rate up. If a manager in a scaling team can only manage 4 salespeople, and your churn of salespeople is 2 people, for every 2 people you hire, only 1 of them makes it, and it takes them 9 months to ramp, you put that together, and the sales team goes like that, and people just can't believe the maths. And so, they underhire, and they get to the point where they just haven't got enough aren't generating enough pipeline to fuel the growth rate. It's very, very, yeah. What else? What else have you got that, uh, where?
So I think we overvalue advice. Most people overvalue advice and undervalue accountability. So there's that wonderful book, which I'm sure you'll be familiar with, Michael Bungay Stanier's Advice Trap, which is never give advice because you probably haven't understood the problem. If you've understood the problem, you probably haven't got the solution. And if you've understood the problem and you've got a solution, they're not going to listen to you anyway. And I think like as founders, We're often out there looking for like this silver bullet of advice, which is going to sort of solve everything for us. And in my experience, that very rarely exists. But actually, you know, and it goes back to that context of the role of the board plays, like, yes, you can get some really good advice from it. And I can think back to some wonderful moments that guests who've been to the boardroom have shared where they just had an inflection point in their business. Nick Jenkins at Moonpig, when he was sitting there, the business was about to go bust. And one of his board members said to him, Nick, why do we need to sell these cards for £1.99? Why couldn't we sell them for £2.99? And he'd just been obsessing on selling these cards for £1.99. That was one of the pillars he was building on. And suddenly, this transformed the economics of the business and sent them on the way to being a billion, multi-billion-pound business, because that extra pound just dropped straight through. And of course, the consumers, whether it was £1.99 or £2.99, they didn't really care. But I think actually it's that discipline of meeting periodically and the sort of the accountability that the personal training that we talked about earlier gives you that I think people underrate because we always think we can do it ourselves. And then yet actually we're typically not very good at it.
Yes. And I think that assumption thing happens all the time, and particularly about price. If there was If there was one thing I see people getting stuck on more than anything, it's that they have this, we can't put the price up. And it terrifies people, because they just have this fear that if they put the price up, the customers all run away. And in fact, I was talking to Hamish, the CEO at Thriva last week. And he said, it's the same thing about people doing blood tests. The thing is not the needles, it's the fear of what if the result is not positive, or it's the reason that why people, most people aren't good at cold calling. It's the Don't like the rejection, fear the results, so therefore procrastinate or do something else. Yeah. Yeah.
Interestingly, it comes up as a theme a lot on Into the Boardroom, and particularly amongst the private equity investors, that price is one of the strongest levers they can pull, where businesses have— founder-led businesses have typically got it wrong. And there was, uh, it was Lawrence Garrett who talked about this founder he was helping with, and he'd sort of, I think he'd gone out for a drink with him and was sort of Giving him advice. He said, just double your prices. And the guy was sort of pretty skeptical. Anyway, he doubled his prices. And of course, everyone carried on paying. And the guy was worried. He said, but what if I lose half my customers doubling? And he said, look, if you doubled your price and you've halved the number of customers you've got, well, you've managed to maintain your revenues and your cost of delivering them has just gone massively down. And so go and double it again. And he went and doubled it again. And, you know, same thing, like, you know, revenue went through the roof. And it's a funny story because I think that the founder, as a thank you, bought him, I think, an Indian. That was his, like, a takeout meal. And the guy's just quadrupled his revenues with this, like, one bit of insight. But it's a recurring theme, like, just, you know, increase pricing until people go away. And more often than not, actually, if you've got something worth having, people Yeah, we did.
I had to do that at IT Lab. We had to put the prices up 50%. We lost one customer. Everybody else said, well, you were always too cheap, so we'll give you a— we'll give you 12 months to fix the service level because it's a pain to move. That was fabulous. Uh, in terms of your evolution, what, what took you out of private equity into startup founder?
Yeah, good question. I think lots of people thought I was absolutely deluded, and I still sometimes From time to time, I wonder if I was absolutely deluded. In fact, actually, I know I was deluded because I'm rational enough to know if you do the numbers on your sort of weighted probability of success in a startup versus, you know, average or sort of best-case outcome, the numbers do not add up. You're much better on a risk-weighted basis to carry on. You know, if you're in an industry like private equity, to stay, stay in that because, you know, your chances of success or whatever it is, infinitesimally small, or the base probability is infinitesimally small.
Yeah.
You might think, well, I'm much better than the base probability, and therefore I can adjust upwards from that. But even applying for your own delusions of grandeur, you know, sort of on an exit, you just, you never get there. So for me, it was, it was actually, it was my mother had started up the business, and she was having some challenges scaling it. So she said, look, you've always said you wanted to do something entrepreneurial. Now's your time to come prove it. And at the time, I always felt like a bit of a fraud as an investor sitting on the boards of companies, working with some super impressive grizzled CEOs, challenging them, having never run a team of more than about 5 people. And so I sort of thought to myself, there were sort of 2 things going through my mind. One was the sort of the Jeff Bezos regret minimization framework, thinking, you know what, on my deathbed, I am not going to sit there regretting that I helped out my mum. And I think I will find it easier to deal with the thought that I gave this a go and oh well, it didn't work, rather than, you know, had I carried on in my previous roles, I think I was on a pretty good track. But I think I would've sat there always wondering, what if, what if? And I decided I'd find it easier to live with the oh well than the what if. So I think it was those 2 things. And then I think the 3rd thing was, I thought there was, you know, as an investor, like we always saw in our investments, you know, the businesses that did best, were the ones who had great boards. And yet the way we went about finding good board members was really unsophisticated. We paid a lot for it and it wasn't— you weren't getting great people. So I sort of thought there must be a better way of doing this. And I'd sort of seen what, you know, Mum had done in the beginning with this marketplace model approach to finding people where she was surfacing these people in sectors I knew really well, which I'd never come across. And I thought, wow, if you can build that community, of effectively the world's decision makers, that becomes a really interesting space to be. And so I think it was those 3 things that made me think, you know, let's give this a go. I was also, I was lucky with the timing of it that, you know, we'd made some exits in the fund that I was at at the time, which just bought me a bit of breathing room at the time that allowed me to spend those first few years working for nothing.
And how, how big was it when you joined?
4 people at the time burning cash like crazy. So it was a fairly, um, yeah, it was sort of basically sort of ground zero. And I joined actually at the same time as my brother. My mum persuaded us to join at the same time. So, okay, there's the 3 of us, which is a fascinating dynamic.
Your brother's still in the business. Is your mother still in the business as well?
Yep, they're all fully in, which is great.
And how big is it now?
So we're now a team of about just over 60 People. So still, you know, subscale, but actually starting that flywheel is starting.
Yeah. Yeah.
We just sent out our 10,000th invoice the other month, and I think it took us 5 years to send out our first 1,000 invoices, 4 years to send out an invoice, and then 3 years to send out our 10,000th invoice. Yeah. Yeah. So the pace is picking up, but it's, uh, you know, taken a lot longer than I thought it would, which goes back to that You know, compounding point. Yeah. Yeah.
Yeah. And is, is your, if you, if I'm thinking about, you know, you're building a flywheel, is it attraction at the front end? Or is it that you've got, do you have a recurring revenue model? And so, you know, if you're building, you know, if you haven't got a recurring revenue model, then it's about constant attraction and rate of attraction and then number of people in your business, because that's a— this episode is in partnership With CEO friend. I've sat with founders who could see their market changing. They knew it. They said it out loud. And then they put their heads down and they carried on because something else was more urgent that week. By the time they looked up, somebody else had taken the ground. That's not bad luck. It's what happens when you stop looking. You don't get disrupted by something you can't see. You get disrupted By something you didn't bother to look at. CEOFriend gives you an analyst-grade report on your market. Give it your sector and your competitors, and it shows you what's moving, what's changing, and where the gaps are while you can do something about it. You don't need to spend £15,000 on a consultant's report to find out. You just need to look up. Your first month is free with the code in the description. Parallel, you know, that's linked to Yeah. What's, so what's the, what's the business model and has that, has that evolved in the time you've been running the business?
Yeah, it's evolved quite a lot. So, so there's 2 slightly different business models on the different sides of the business. So on the board search side, where we're helping organizations hire board members, we have a mixture of subscriptions where organizations who are hiring board members regularly, so typically educational institutions, investors, large charities where they know they'll probably be hiring 1 to 2 board members a year, they'll have a subscription.
Yeah.
And then other organizations where they just pay to list, to sort of run a search, and then they pay per placement that they hire. So that's on the board search side. And then on the board development side, it's a membership offering. So people pay an annual subscription fee to be part of the membership, and it takes them through their journey from entering the boardroom all the way through to being a sort of seasoned board chair. The board development piece is relatively new. We started that Just a couple of years ago now, so that's you know still the smaller part of the business, but growing very quickly. So you know it's it's been very much the I think we spent quite a lot of time getting our value proposition right at the beginning. We tried going all out with all tech, all tech offering, and we discovered that people just weren't ready for it, even though it was surfacing better people than we have search people within the business. And even though the tech was often surfacing better people, the end client wanted that human. I often sort of draw the analogy with, was it IBM Watson that supposedly, you know, gives you a better diagnosis than a doctor? Yes. People, do you know who've given a terminal diagnosis by IBM Watson would not want to go and speak to a doctor? There was still something about human. And I think it's, um, the same for us, which for a long time has been a source of great frustration. There's a part of me now that thinks actually Now, in an age of AI and disruption, that's actually quite reassuring that people, you know, will not move away from that sort of human expertise and interface piece that I think they're buying. What they're buying, or have come to realize they're buying, is it's more than just a transaction. They're buying a stamp of approval. They're buying expertise. They're buying the right to be able to say, we went to an expert and they helped us through this process so that if something goes wrong, they're beyond reproach. And they're also buying an independent— viewpoint on it, which again, in an age of AI disruption, I think is a really valuable defense to have. Yeah.
And what, what sort of development are you offering in that, in your community offering? What's the, I guess, you know, on the search side, you're saying to people, your proposition is we know more people, we've got a great network, we'll do that third-party validation that these people are good and it's all we do. So we're better, you're better to come to us than a, than a recruitment company. Who do a bit of this. And on the development side, you are helping people on that journey into boards and who are already on boards to be better board members.
Exactly. There are 3 kind of core pillars to it. There's board success, which is about helping you get a board role or board roles. There's board excellence, which is about helping you being better in the boardroom once you're in there. And then there's the board networking piece, which is about expanding your board network, which is both about helping you find more board roles. because you maximize the surface area that you're touching on. Most board roles still go through word of mouth. And also then once you're in a board position, being able to bring your board network to bear. And so, you know, for a lot of people, it'll be just about like, where do we start? You know, historically, it's been the same old names in boardrooms, people who happen to know the right people rather than the best people. And a lot, for a lot of people, they just wouldn't know where to start.
Yeah.
So the board success piece is about holding people's hand through that, making them aware of all the different types of board roles that are out there and what might match up to their expertise and their passions and interests. And then Board Excellence is very much actually again built out of my own experiences. When I came out of the investment world, I got asked to join a board as an independent. It was my first sort of paid board role. And I was the first independent director of this family-owned business. And I just had this sudden moment like, oh my gosh, I have never seen anything like this. And who do I go to talk to about, like, how best to approach some of these, like, really interesting challenges? You know, it's a brilliant organization. And had it been a private equity, in my private equity investment days, I would have gone to speak with my colleagues, and you bounce ideas across. And actually, you've seen a lot of the things before. So, it's—
Yeah.
After a while, it becomes just pattern recognition. But suddenly, in this different environment, I was kind of a little bit at sea. And I went, started going to a lot of the sort of classic, like, education providers for the board space. And I sat there thinking to myself, Have these people actually ever been in a boardroom? He says, no. And you'd have like lawyers and accountants who are basically selling services, giving you the textbook of what a boardroom should be through the eyes of the law or through the eyes of— Yeah, yeah, yeah, yeah. But not actually people who'd been in the trenches. And I was super lucky because I happened to have 60,000 board members I could call on to bounce ideas off. But I thought, well, what does everyone else do? Because it's this really lonely life once you become a board member where you don't have a group of colleagues. And so that was kind of, I guess, really the genesis of the podcast, starting to speak with people who'd had experiences in boardrooms and getting them to share them so that others could learn from them. And the genesis of the Enter the Boardroom community, which is about bringing people together very much through sort of peer-to-peer learning. Like, if you want to go get the academic answer, you can go to, you know, the business schools or whatever. We'll never be as good as them for a sort of pure academic offer. Give us 100 years, maybe we would get as good, but we don't have a right to win. Whereas what we could do, my sort of, I suppose, strategic view was what we can be the best in the world at is using our technology, using our network to bring people together to learn from each other. And we can do that better than anyone else at a bigger scale than anyone else to build really valuable insights for those in the boardroom. So that's what it is. It's very much about experiential learning and people sharing challenges they're wrestling with, with a group of well-matched peers to help them be better in the boardroom and expand their board portfolio.
And looking back, what are some of the things you wish you'd known that you know now that you wish you'd known earlier? What are some of the gotchas that you've had to overcome?
I suppose I'm not one for regrets. I think I was very lucky at the beginning. I had a really good coach when I first started out. who really helped me make that transition from investor to operator. And at the beginning, I used to just get overwhelmed by everyone coming to me when we were sort of going through that transition of sort of 10 to 20 people.
Yep.
Helped me sort of put in place the frameworks and the structures to batch time, to get people to understand that, you know, they should batch their questions in, you know, at a time when we've We were doing one-to-ones, not just come to me at any point in time, to think about the sort of different reporting lines in the business. So I think that I was really lucky with that. I think, you know, one lesson that's constantly tripped me up has been this, you know, the greatest challenge of communication is the illusion that it's taken place. If you haven't said something 10 times, you haven't said it. And so I used one of the bits of feedback I used to get in the early years is like, what's the strategy?
Yeah.
And I'd sit there tearing my hair out, because I'd be like, we've been through the strategy. And so, over time, what I realized was, well, there were 2 different things people were looking for. When they talked about strategy, actually, what they wanted was a plan, not a strategy. So, I'd spent a lot of time thinking about the strategy and not enough time on the plan. But then also, the first time I talked about the plan, they were picking their nose or thinking about what they were going to be sort of shopping for that evening, so they didn't hear it. And then the second time you did it, they had some other crisis going on, or You know, 10% of the people did. So it wasn't until you'd said it 10 times that it came out. And of course, when you're saying it, you think people must be bored of me by now. But it was one of my early podcast guests who sort of shared that insight of if you haven't said something 10 times, you haven't said it, which has actually really helped me over time. So I think that's been really good. I think the other one that I sort of still wrestle with is how to make sure that I'm maximizing the value that I'm adding as a CEO. Uh-huh. Not getting caught up in the day-to-day or the weeds. And there was a really helpful piece I came across. It was an HBR article looking at how the best CEOs allocate their time and just benchmarking how I was using my time against that. And there's this sort of wonderful insight that dropped out of that where someone said, look, your, your to-do list is what you want to do, your inbox is what other people want you to do, and your calendar is what you end up doing. And I think when I'm operating at my best, I'm being run by my calendar and I'm really on top of my calendar. And I think that is something that I wish I had sort of discovered earlier to ensure that I wasn't being sucked into things that, you know, other people wanted me to do and was remaining sort of crystal clear. And that probably feeds into another thing, which I still haven't learned as a lesson, but as an investor, I used to tell people to focus, focus, focus. And now as an operator, I'm just constantly coming up with brilliant ideas. Which? Which of course create, you know, you're constantly navigating that line between diversification, you know, hedging your bets a little bit so that if one thing blows up, the whole enterprise doesn't sink, and diworsification, which is where, you know, in investor parlance, once you go above sort of 20 positions in an investment portfolio, the marginal benefit you get from the additional diversity is offset by the fact that you don't know those positions as well. And actually, many of the best investors I know probably will only have 10 positions in their portfolio. They'll be really concentrated, but they'll know those positions really well. And I think there's a lesson there as an operator. And actually, it came out in one of the podcasts I did with, uh, it was episode 123, with this private equity partner where they looked across all their portfolio companies. And one of the recurring themes of those that were were doing best were the ones who had surfaced the 2 to 3 key things to focus on, and that sort of power of focus. And when I first started, I said, we should do executive search as well as non-executive search, because there's a huge market opportunity in there. And of course, that is right, but suddenly everything is spread, your product budget, your marketing budget. And so, you end up, you spread across 2 things, suddenly you've got 50% of the resource, and it's hard enough when you've got small resource, when it's concentrated 100% on one thing, to succeed in that area. Once you split it 50/50, or often in my case, it's like spread across 10 things, you know, you haven't got a hope. So I think, you know, that focus has been one of the lessons I have still not learned, but I wish I'd learned earlier.
How's your leadership fared? So one of the things I love to contrast is, I suppose my analogy is if you're in the 3rd division and you want to be in the Premier League, not very many of the players will still be on the field by the time you get there. Have you— has your leadership team grown with the company, or have you had to replace some along the way? And, and has that journey given you some lessons?
Yeah, for sure. Lots of lessons. Yeah, no, it has grown and it has evolved as we've gone over time, and some, you know, real sort of mix. And, you know, what, what have been the, the lessons? I mean, I guess there's a sort of the classic of, you know, what got you here won't get you there, that there are some people who just Won't scale, don't quite step up. And I think if anything, I've probably been too slow on that. I think there have been some sort of toxic behaviors from time to time that I have sort of tolerated or sort of worked around. And actually, it's only with hindsight that I've seen what the cost of that has been to the broader team.
Yeah.
Individuals who are exceptional in many ways, but had one or two sort of traits that were, you know, just slowed the rest of the team or de-energized, you know, other members of the team. And it's one of those things where I'm not 100% sure if it was right or wrong, but I tried to sort of coach them through it. And actually having sort of, you know, seen it from both sides now, I think I should have moved on faster. And actually, there's a piece I was listening to the other day, I forgot what the source is now, but where the person was asked, you know, have you ever fired someone too soon? And the answer this person gave was no. And I was thinking about, well, have I ever fired anyone too soon? And the answer is no. And the follow-on question is, well, if you've never fired someone too soon, how do you know where that line is? And I think that's probably right. And I think it's something I've got better at now. And I'm tired sounds like a horrible, a horrible word. But I think it's sort of being really on top of, you know, really clear on what the performance metrics are and really clear on when someone's meeting them. And if they're not meeting them, that, you know, they realize at the same time as you. And so then it becomes a natural parting of ways. And I think I'm much better at that now than I used to be.
And have you got, have you got, what are the characteristics that you might've got better at spotting the people who can scale and the people who can't? Is it behaviors or is it personality traits?
So we've gone through a real journey on thinking about hiring, which given the whole platform is built on. Yeah.
Yeah.
Yeah. We've thought a lot about, you know, in the early days I've read a lot, like as an investor, I used to think I was pretty good at hiring. And if you'd given me, you put someone in front of me, you know, for half an hour, an hour, I could have told you, you know, whether they were going to be any good as an investor or not. And then when I came into this role as an operator, where suddenly I was having to hire salespeople and marketing people and all these roles that I didn't really know what they did as an investor.
Yeah.
I was getting it wrong, left, right, and center. And so I sort of started researching and realized that actually turns out no one's any good at hiring, whether they know it or not. But there are a few things you can do that can increase your odds of success. So there was this study by this pair called Schmidt and Hunter that I came across through Laszlo Bock. Work Rules book, which showed that basically there are a few things that are good predictors, which are general mental ability tests. So, numeric reasoning, verbal reasoning, and job-specific tests are 2 of the strongest predictors. So, if they're going into a board role, give them a board paper and have a board-type discussion in a board-type environment around it.
Yeah.
It shouldn't be that surprising. So, I think we went down that path for some time. We figured out, for example, when you're hiring engineers, Often people who score very high, good engineers tend to score really highly on verbal reasoning, because I think they're very logical, and that translates into engineering. But actually, we ended up at a point where we had some really academic, book-smart people, but we didn't always have that sort of drive and resilience.
Yeah.
And we sort of then went back down a path of looking much more for attitude, and much more into the school of, if you give me someone with the right attitude, we can teach them everything. And we're probably now somewhere in between those two of trying to be much more structured with the kind of being really clear about what does success look like and how does this person match up against success, but with a sort of real focus on do they have the right sort of attitude, the right cultural fit. But I think it's one of those things again where the needs of the business change over time, but actually what you need when you're a 10, 20-person Yeah. Is quite different from what you need when you're 50, 60, um, you know, from my investment days, you know, $500,000.
Yeah, yeah. What you— obviously you read a load of stuff. Harvard Business Review, you recommend having that as a subscription. You— is that— is that— is— did you reference HBR because you get it and read it regularly? Is that a thing that people should do? Or maybe you've got books that you recommend as well that have helped you along the way.
Yeah, I think sort of the challenge now, and we have no shortage of stuff to read or listen to, and you can spend all the hours in the day reading, listening to. The challenge is figuring out the sort of signal from the noise, what's going to be really helpful for you. So I go through periods. So right now I am not subscribed to HBR. Occasionally I'll come across an article that I think is useful or a series of articles, and I might read Resubscribe, but I have not got the time to systematically be reading stuff. But I will go through phases of listening to specific podcasts, or I tend to try and read books rather than articles. I did get an insight from someone who said, look, the advantage of a book is it's been distilled over time. Lots of articles tend to be reasonably ephemeral. They haven't stood the test of time.
Yeah.
By the time someone's written a book, it's really had to go through a filter. So there have been, I suppose, 3 books that have been really helpful for me. The first was a book called Growth Mindset by Carol Dweck, which came back from my investor days where someone, an investor, you know, said to me, Ollie, how many brilliant investors do you know who don't read a lot? And at the time, I didn't read a lot. And around that time, I heard Carol Dweck speaking, and she talks about, she talked about the plasticity of the brain and how it compounds over time. And, you know, that was just a sort of game-changing moment for us where I suddenly thought, oh my gosh, I've been like wasting, wasting all this time not reading enough, and just went into overdrive on reading.
Yeah.
So that, that was a really important sort of moment for me, and understanding that the power of the brain to constantly evolve, and literally like a muscle, you know, it's epic teach us books, the weights of the mind, like a muscle. The more you read, the stronger your muscle gets. So that was a game changer for me. I think the second one that's been really powerful for me was a book called Drive by Dan Pink, which I'm sure you all know.
Yeah.
When I sort of left the investment world, where people will walk through a brick wall if you ask them to in the investment world, just because they're paid so much. And coming into the non-investment world, where people's motivations are often different, suddenly, and I'd never had to sort of manage or inspire people before, and I'd ask people to do stuff and they wouldn't do it. I was like, well, I told you to do it, why are you not doing it? And it made me sort of really question, well, how do you motivate someone? And Dan Pink's book is brilliant because it's all about, you know, the surprising truth about what motivates us. And it boils down to 3 things: autonomy, mastery, purpose. If you give someone clarity about why they're doing something, and a deep why, like a meaningful why, like why—
Yeah.
—you get excited and out of bed every day, and you equip them with the skills to do it, the mastery to do it, and then you give them enough space to get on with it, then you unlock a sort of a sense of drive that, you know, you'll never replicate. And I'd seen this in a couple of other businesses after I'd left the investment world. And this was just a real unlock for me of how to think about inspiring and leading people and fostering passion and commitment in a resource-constrained environment. And then the last one would be, but by guy called Clay Christensen, who was one of the most brilliant thinkers, wrote The Innovator's Dilemma.
Yeah.
That's probably best known for, but he wrote this book, How Would You Measure Your Life? And, you know, basically, he applied his sort of brilliant strategic management sort of consulting mindset to this problem of, you know, when he'd set out, I think he was at Harvard or somewhere like that, you know, he was alongside what he called the masters of the universe, and they all set out with these incredible ambitions. And every 10 years, they'd come back together and reconnect. And every 10 years, they'd come back looking a little sadder, a little more overweight, a little more miserable, a little more depressed. And he sort of got to the end of it, and he's like, how did all these people with such potential end up in such a horrendous state, effectively? And it's worth reading, but it boils down to the fact that the level of discipline, and it goes back to that accountability that we talked about earlier, that they applied in their professional lives, they never applied to their personal lives. And so when they had the kind of, you know, the budget meeting or whatever it was, they went to it and they did an A-star job on it because their bonus was going to reflect the job they did. Whereas when they got the call for their kids', you know, I don't know, play or, you know, concert or whatever it was, they said, well, I'll come next time. I can't make it this time. And so, they got a C grade on that. And a C every now and again is not the end of the world, but coming back to the compounding thing, it compounds over time. And so, really powerful, the way he articulates that, is a really powerful illustration of the compounding effect in your personal life. And for me, I'm someone who obsesses about things. And so, it's a really helpful reminder to keep those obsessions balanced, or at least focused the right things and the things that matter most. Because, you know, another great book, Regrets of the Dying. Most people, you know, don't regret that they spent too much time at work. They regret they didn't spend more time with their friends, family, significant others.
Well, 18 summers, was it? 96% of the time your kids will spend with you is by the time they're 18. So you've got 18 summers. Enjoy your time in Berlin this summer.
Yeah, exactly right. It's always terrifying. And same thing applies to, you know, your parents. When you think about the number of days now, you know, at the age we're at, if you're lucky enough to still have them around, you know, the number of days that you'll have is very small.
Yeah.
So it's sort of treasure each one. And, you know, sometimes it can be difficult.
You said that with way too much feeling.
Bear in mind that I'm so lucky. I've got incredible, incredible parents who Just been amazing. But it's easy to take these things for granted. And, you know, just having seen it recently through friends, significant others who've lost their parents, it's easy. Again, it's that availability bias, you know, just to take these things for granted.
Yeah. Ollie, thank you very much indeed for sharing your time with me today. It's been great having you on.
Thanks so much for having me. Pleasure.
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