How to Spot Leaders Who Will Scale (Look for This, Not Confidence) | Luke Tobin

In this conversational interview, entrepreneur and investor Luke Tobin shares his hard‑earned insights on what separates founders who can scale their businesses from those who cannot. He argues that failure teaches more than an MBA, that founders who remain the product often stall, and that self‑doubt is a useful growth signal rather than a weakness. Tobin explains why minority‑stake investments align incentives better than full acquisitions, and he outlines the shift from founder‑as‑eye‑of‑the‑storm to a delegating CEO. He discusses hiring and promotion pitfalls at the 50‑100 employee threshold, the importance of deliberate practice, and the trade‑offs between remote, hybrid, and office‑based models. Throughout, he weaves personal anecdotes from his own three exits, his upcoming book on doubt, and practical advice on leadership development, curiosity, and character traits. The interview concludes with recommended reading for founders and ways to connect with Tobin.
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Failure is a better business school than an MBA. I believe that most agencies or businesses will never scale because their founder is the product. The one common denominator across all of the people that I'm talking to, and also in myself, is that you can't undo hard work and preparation. The more they do, the more they prepare, the more they put themselves in those situations, the better they are at dealing with those situations.
Because you can be in a really miserable place, but if you haven't been in a miserable place, you don't know that dawn will come.
And then as you get towards 100, you've got to start playing football.
You've got to get yourself off the field and the team Most acquisitions fall over or don't go as well as they should because the founders aren't incentivized. And if they're still at the center of that storm, you've got to keep them burning and keep them pushing. I'm Luke Tobin, entrepreneur, investor, and founder of Unusual Group. I've been building companies for over 20 years, had 3 successful exits in 3 different industries, the largest of which was a performance marketing agency, a company called Digital Ethos, which I sold in late 2022. And I now run a holding company investing in marketing creative service businesses, helping them to scale without losing control. I'm also a partner in a venture studio in San Diego in the US where we're rolling out certain consumer goods products. I live in Portugal, and I have 800,000 followers on social media, which I support with success psychology week to week.
Very good. Very good.
You said you'd been in business though for 20 years, so you must have some sort of facial routine that you should share with everybody as well, because either that or you left school at 16 and just started your first business.
Well, cleanse, tone, and moisturize, they say, don't they? No, I'm 41. I'm 41. So, lots of good moisturizer is the key and sunshine.
But living a good life in Portugal.
Exactly. Look, you know, good food, good exercise. Yeah, all of those things make a big difference, don't they?
What took you to Portugal?
2 things, really. You know, I was very happy in the UK. I was there before this, but I've always been a traveler. I've lived in Australia, I've lived in the US, I've lived in different countries over the years, and I felt like I'd been back in the UK probably long enough and wanted a bit of a change. And Portugal offered a really, you know, compelling lifestyle. And, um, and we had a lot of friends here as well. So my partner and I, we were like, actually, if we don't do it now, we, we just won't do it. So let's just, let's make the move. So last April, we came over, found a place, and, and here we are, and not looking back. It's been, it's been fantastic. Really good decision.
And whereabouts are you, in Lisbon or down on the, down on the south coast?
Yeah, near Lisbon, a place called Cascais, which is the Portuguese Riviera. It's kind of 20 minutes drive outside Lisbon.
Yeah, fantastic. Right, uh, Luke, what, what are some things that you think are true that the rest of the world might think are bollocks?
So failure is a better business school than MBA.
Okay.
Um, I believe that most agencies or businesses will never scale because their founder is the product. Okay. I believe that minority investment beats full acquisition. And I believe that self-doubt isn't a weakness to overcome.
Oh, I'm going to start with that last one first then. What— why is self-doubt not a weakness?
So there's a few things at this, but it's, it's the, it's the edge typically that separates high performers from those that are growing. And I'm in the process of writing a book at the moment all about doubt and how we can recognize the different archetypes of doubt. So if we touch on a couple The one that most people feel more often than not is imposter syndrome. But imposter syndrome appears when you are stepping outside of your comfort zone, which generally means you are doing something that's expanding your boundaries, not retracting your boundaries. It means you're pushing yourself to, to become better, to do something new, to, to step outside of that comfort zone. So imposter syndrome, when you actually start to reframe it that way, is something that you can leverage because it means you're actually doing something productive. You're doing something good for yourself. So as much as it feels awful at the time, and you start to get all of those kind of fight or flight responses, if you can learn to recognize it and learn to harness it in a way that benefits you, it can be really good. Another one, there's lots of archetypes, but comparison doubt. And in the age of social media, we all have it. I think a lot of people are living their lives, unfortunately, by comparing themselves to others, and you kind of can't escape it these days, whether it's LinkedIn and somebody getting a promotion and you are not, or, you know, somebody raising a load of capital and you haven't, or whatever it is, you know, there, there's peers everywhere that seem to be doing well. But in the age of comparison, one of the things you can do is learn to, um, to be nice to yourself and give yourself compassion and be grateful for what you do have. And there's lots of frameworks and things you can do to start overcoming that. So again, it's, I've interviewed to date about 30 high performers in different industries, from the military where ex-SBS commandos that are in high stress situations, I would argue higher stress situations than most of us will ever experience. Their lives are literally on the line and they find ways of coping with that and overcoming that kind of high pressure. And then actors that have to put on performances and often be different people, become other people, you know. And that carries a lot of internal doubt. And what I've found is that those that are the people that we probably look up to the most and go, oh, they've just got their shit figured out, or they are the ones that are most confident, often are the ones that struggle with doubt the most. But they, they find a way to move anyway, and that's the point.
And is there something about, ah, Um, you know, that sort of feel the fear and overcome it. Is there, is there something about that they, they're happy to be uncomfortable, that the thing they're learning is that it drives them to do it better, but there's some, they must get something from being uncomfortable, from feeling uncomfortable.
Definitely. I think it forces them to, to level up. You know, there's always another room. There's always another another space or place that you want to get to. And I think what they've realized is doubt is the cost of admission to those places. So in order to be who they want to be without doubt, it means they're not getting there. So actually, they need to have those experiences and those feelings in order to reach those next levels. So they've just learned that that is a bit of a superpower rather than a hindrance.
And how's your doubt going around Writing the new book?
Well, I've got a lot of doubt, funnily enough, writing this book. It's a fantastic paradox. To be honest, I wrote the initial version of the book, kind of V1, from my perspective. And then I thought, you know what? I need to go a lot deeper on this. I don't want to not do it justice. So I've gone out and then interviewed a lot of really other high performers and taken taken a bit longer on the book to really go and get different perspectives and add more depth to the book, which has been fascinating. And I've learned so much more than I ever expected to learn about myself through the process. And if I was to have looked back in my kind of 20s or even early 30s, I would never have considered writing a book about self-doubt because I was one of those people I think archetypally was outwardly confident. And you wouldn't have thought that it was, but I think that's the piece. That is the paradox. Doubt is actually more prevalent in people that appear to be confident, more often than not, than those that are quiet in the room. And the ones that— it's fascinating when you start getting into it. It really is.
Because the more you push yourself, the more you are deliberately occupying a space of doubt.
Exactly. If you stay in your comfort zone, you don't have it.
If you've got no doubt, it's—
yeah. Yeah. But most people are so scared of the feeling of doubt or the different responses that we have as human beings, because a lot of it's physical and psychological, that they avoid it. And they avoid it so much that they never push themselves out of their boundaries. By not pushing themselves out of their boundaries, that's a decision. And they then avoid all of the opportunities and the chances, the luck that you create by pushing yourself.
It becomes self-reinforcing. This idea that people would rather die than speak in public. And in my mind, when anyone says that to me, I've got sitting in the pews at a funeral, And you're going, really? You'd rather be in the box than stand up now and give the guy's eulogy? Really? Really? And people are like, oh no. And you're right, it becomes physical. People start to— the heart races, they can't— it's funny.
Well, somebody said something to me the other day, actually one of the interviews. They said, look, 5% of life is perception. The rest of it is just It's just noise, and it's like it's really it's the voices or the things that you tell yourself become your reality. So if you tell yourself I'm not somebody that can do something like that, or oh I just really know that when I tried to do that last time I felt like shit, or I just couldn't do it, and you tell yourself that enough you end up believing it, and then you just don't give it a go. And actually the the high performers that we see and people aspire to want to be, they just move anyway. They still feel those things. They still get nervous before they go out. I spoke to a famous actress the other day, and I can't name her yet, um, but she will feature in the book. Um, she's, she's been around making movies since the '90s, you know, incredible actress, um, really well renowned. Um, but she was like, Luke, I just used to get petrified. I'd feel sick before she went on stage, before she did a movie. Said sometimes I would throw up, but I just do it anyway because I knew as soon as I got into the into it and the camera was rolling, I would love it. And it's that perception often, that feeling that you get before that stops most people. But when you actually do the thing and you realize you can do the thing, you can then overcome because it just compounds. So, you know, deciding not to do something is a decision still.
Is there something about training as well? You know, because I was watching Newcastle get massacred by Barcelona last night. Right. And, um, you know, I, I think 90 minutes of football, somebody, they're on the, they're on the ball for 2 minutes in 90 minutes, you know, and, you know, 2 minutes in 90 minutes once a week, but it's a full-time job.
Right.
And so, uh, you know, I was thinking about, you know, you mentioned the SBS guy, actresses. There's, there's a, there's a delivery, but then there's the this massive pyramid underneath of all of the things to training, development stuff. So when you're under pressure, it doesn't— you don't fluff it. Is that a component to it? Like, you know, wanting to put the work in? Because again, if you think about the sort of social media world, it's like, oh, all you have to do is do a thing and you can have a £10 million business. Like, if only it was that easy. But—
If only it was. Yeah, the one common denominator across all of the people that I'm talking to, and also in myself, is that you can't undo hard work and preparation. So one thing that they all do is graft really hard, and they've honed their craft over years of doing. And also, the more they do, the more they prepare, the more they put themselves in those situations, the better they are at dealing with those situations. over time. So it's everything. Dealing with doubt is a practiced art, similar to performing or doing your job. Most of us find that we become quite competent over time by doing our jobs. They say that 10,000-hour thing, anybody that does 10,000 hours of a thing can be in the top 1% in the world of that particular topic or subject. Well, most of us, if we go down our routes of careers, after 5, 10 years of being in those careers, we're all experts at what we do. And we, you know, that's hence why we, why we can keep getting work and getting employment. But these people, they realize that, but they realize that when it comes to doubt, and, you know, their belief in themselves comes from proving to themselves time and time again that by preparing, and by putting in the work, they can overcome and they can continue moving to the next level.
But the 10,000 hours thing is interesting because the original research that Gladwell quotes in his book, I think the thing he misses is that it's 10,000 hours of deliberate practice, not just sort of 10,000 hours of doing, which is why when you see people playing golf, for example, and you think, God, you've been playing golf for 30 years and you're still shit. It's because they might have played golf for 10,000 hours, but without any deliberate practice behind it. And also, the other thing that the research found was that the people who ended up being soloists, because it was a violin or viola school in Austria that they were doing the research on the students there. The people who went on to be soloists didn't enjoy practice more than anybody else.
Yeah.
And so it's deliberate practice, but it's not that anybody enjoys it. And I was thinking about Andre Agassi's book about his tennis career, and he claims never to have enjoyed playing tennis ever, but it was a way in which he and his family could become wealthy and therefore had to do it.
Incredible. Yeah, incredible, isn't it?
Look, let me, uh, I think the next one that links most simply to this is that failure is better than an MBA. Have you got an MBA?
I haven't. So I mean, this is, this is from my perspective. But, but also, you know, I work with a lot of founders and I work for a lot of people that do have them. Um, and don't get me wrong, look, you know, MBAs are fantastic and really good tools, and a lot of people need the, the frameworks and the discipline that it teaches and gives people. However, from my, from my experiences and a lot of the founders that I work with that have been arguably the most successful, most of them have just gone through a lot of trial and error and have had—
Yeah.
Failed businesses early in their careers. Um, they've had their fingers burnt, and off the back of that, they've learned to be shrewder, better, wiser in the next businesses that they build. And I think time and time again, if you're in a room with somebody that hasn't been through failure in business or hasn't had to really be up against it, they can become like the most dangerous people in the room, right? You need somebody that's actually got a few scars along the way in order to weather the storms.
Well, it's the— Because you can be in a really miserable place, but if you haven't been in a miserable place, you don't know that dawn will come, right? It's that.
Yes, exactly.
Exactly. What's your biggest— when you look at the scratches on the bed, the headboard, what's your biggest failure?
I've had 3 businesses that I kind of wound down because they weren't getting anywhere. And I look back at some of them now and I think, well, you know, we could have— I could have worked harder, could have been smarter, could have, you know, didn't have the passion for them or whatever. Then I had one that, that failed, um, and was really kind of giving it my all. So, you know, I look back at those and, you know, I think I could have— I've learned a lot. You know, hindsight's a powerful thing, isn't it, if you look back and you actually take the lessons that it gives you? Um, so, you know, there was a few things there. Also my last business, which, which arguably was my most successful. So I've had 3 exits, but each one has been bigger than the last. My last business, Digital Ethos, we scaled to an 8-figure exit. But along the way, I made a lot of mistakes with team members, hiring the wrong people, promoting people based on their tenure rather than on their experience and what they could actually deliver. I just made so many mistakes that actually, I think back, We could have been an even bigger and more successful business had I not made a lot of those mistakes. But again, those scars and those wounds make me a better manager and leader today. So, you know, it's all part of that process.
Okay. Most agencies, most businesses never scale past the founder because the founder is the product.
So yeah. I think this is a really key issue because most founders find it very difficult to delegate. And they sit at the kind of— if you imagine you've got like a, um, like a force or a storm, they're the eye of the storm, aren't they? And they try to keep control of everything that happens around them. And I think that can be a real danger. I think actually the founders that I know that have been most successful are the ones that basically start that energy, moving, and then as quickly as possible, splinter off and have mini storms going on in other people and find good people to facilitate their weaknesses or their gaps as quickly as possible. I actually think the founder's job really, more than anything else in the first few years, is to make themselves as much as they can redundant and focus on the areas that they actually can add the most value to. But 99% of the time, founders don't do that. Actually, and that's where the difference between those 1% real outliers lies, I think.
So in my mind, I have this, as you have a startup and you're gaining momentum, you can probably pull this through 30 to 50 employees. It's like playing basketball. It's exactly the eye of the storm, right? You're involved on the court in every move, and you are better than the people on the court, right? If you, me, and LeBron James are playing, we're still going to win because we've got a rock star with us. And then And then as you get towards 100, you've got to start playing football. You've got to get yourself off the field and the team have to be self-sufficient.
Yes.
And be able to change the game and hold each other to account. And I think my thesis is that people get stuck somewhere between 50 and 100 in no man's land because it was working. And so that you can work hard and you can get the business up to 50, 60 people and 5, 6, 7 million turnover. And then it's really hard. And because it was working, there's no— maybe they lack doubt. Maybe they lack doubt and/or curiosity. So they're going, somebody else must have fixed this. And instead they just keep trying to work harder through it. But every week the phone rings with somebody going, I'm working 14 hours a day, 7 days a week. Like the business is successful. What do I do now? And so because you've been through it, And you can see it. Why do you think other people— what stops people, I don't know, maybe looking outside and going, maybe it's just that— are they just too busy?
I think a lot of it probably is that. I think they're so scared of the wheels falling off if they weren't in the business every hour of the day. They probably don't have time to strategize, pull themselves out the weeds enough to maybe see sense. And actually, that's where it's important to have coaches and consultants and people that you can lean on, like mentors, because Yeah, your own perception and your own perspective becomes all-encompassing otherwise, doesn't it? Because you're just in it every day. And I was definitely one of those until we got to 90-odd people before I sold. But you're in this weird limbo, as you well know, at kind of 50 people. You've got a decision to make. You're probably as profitable at 50 people as you're going to be at 90 people because you're going to have to go and hire a load more senior people. You've got to build a structure. You need to So actually, if you really want to go for it, you've got to sacrifice that bottom result or the kind of profit to get to that next level. And that's where a lot of people get stuck. They go, well, hang on, I don't want to hire internal HR. I don't want to hire— which is what they have to do to splinter away from themselves. But they try to hold on. I think some of it's margin, some of it's profit, some of it's just used to their lifestyle. I don't know. But most of it, I think, comes down to time. Time and experience.
And they've done it.
Yes.
And I think that they don't know that they're going to end up being less profitable. And then that the lack of, as the profitability gets squeezed, they try to work harder and it becomes less enjoyable.
Exactly. Exactly.
And so, businesses do end up going backwards or get stuck.
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And then the last one you've got is minority investments better than full acquisition?
Yeah, this is an interesting one because most of the private equity market moves for majority ownership in businesses when they do acquisitions, or, you know, holding companies tend to take controlling stakes. And I did a lot of research into this. So coming out the back of my last exit I had last year, kind of figuring out what I wanted to do next. And I launched Unusual Group in October. There was a lot of pre-work before that, but effectively we looked at the creative service and agency landscape and we thought, well, look, with AI and disruption going on, there's a lot of work to do. There's a lot of good founders out there that need a lot of help. And we looked at the different models. Do we go in and buy controlling stakes? But the problem I've seen, and even in my own exits before, as soon as you get 50, 60, 70% of the cash upfront and there's an earnout or there's some sort of trigger there for the additional capital, you're not as motivated as you were when all your chips are on the table, and for obvious reasons. And you had to make sure that it had to work. So that bit we were just talking about before, where founders of the product, for most businesses, most acquisitions fall over or don't go as well as they should because the founders aren't incentivized. And if they're still at the center of that storm, you've got to keep them burning and keep them pushing. So we go in for, and we believe that minority stakes align interests better. And then you find the right founders that are still hungry, that still want to push the thing, and you go on a journey with them basically, rather than kind of stripping out control day one. You obviously want to have levers in there so that you can end up being majority control, but you don't do that straight away. And I think it's a mistake that a lot of private equity businesses make.
Yes.
Well, because I see it all the time where not only is the motivation broken, but in about a third of the cases where we have a client who sells majority stake but carries on doing an earnout, somewhere in that first year they lose the will to live and they walk away leaving the rest of the money on the table because they've They've signed up to a plan. They were running the company and now the new owners are just doing ridiculous things and decimating their business and they just can't bear it anymore.
Exactly.
So they just pack their bags and go, mainly for mental health issues.
Yes.
Save their sanity because they just can't bear it anymore. Okay. So I want to go back to one— you started talking about scaling and management and leadership. And one of the things, one of the recurring themes is exactly that. You said you exited the business and you were 90 people and you've had to bring in some external people to free you up. And also you've promoted some people into sort of management or leadership roles based on tenure. So maybe you could talk about some of those lessons. Did some of your leaders were with you at the beginning and they survived and they were with you all the way through? Other people didn't make the leap and why?
It's interesting. I mean, speaking honestly, I think The original people that were in the business kind of day one, I think we ended up with maybe 1 or 2 of them at the point we exited. We turned over the team for good, bad, or ugly at least a couple of times, I would say, during that 6, 7-year journey. So fairly quick journey, but that's because a lot of the people that come in at base level and they come into a small business, that type of mentality, And then as you start to scale and you're scaling quickly, you know, they don't all have the, the want, the desire, the ability, um, or the ambition to go through that journey at that kind of speed. So, you know, um, there was a lot of people that, that didn't make it or couldn't make it because of the ambition that we had overall. Um, I think we became better over time at finding the right people, but normally that was because initially, yes, I'd promoted a lot of people because we needed it. You know, at one point we were hiring 5, 6 people a month.
Wow.
And it was just really difficult to find good managers. So I was like, well, you know what, I've got someone here that I trust, that I like, let's give them a go. And, you know, that was a mistake because a lot of people shouldn't be managers. You know, they're great at their disciplines, they're great at what they do, and, you know, you might get on with them, but they really shouldn't be managers. So I made all of them.
And it's terrible for 2 reasons, isn't it? Because you promote them And then typically what happens is when they don't work out as a manager, they don't go back to being the amazing sole contributor that you trusted. They end up leaving as a failed manager and you just would've been better leaving them where they were. So what did you do to get better at hiring?
A few things. So what I came to realize was by promoting those types of people, you had loyalty, but not necessarily capability, and they would kind of agree with you on things. Actually, what I wanted was people that would challenge perspective and, you know, free me from some of these roles. So, um, as we, as we scaled more, it was going out and finding seasoned people that could fill in the gaps and, you know, could come in with experience. We, we hired and resourced from a lot of competitors, you know, larger competitors. That, that helped. But a lot of it is, you know, what do they, they say, you know, Hire for attitude, train for skill. I think there needs to be a bit of both. Um, you know, I definitely needed both in, in that environment. But one thing that we did, which I think is still fairly unique to this day, is we would pay people for a full week in the business. So senior leaders, we—
Wow.
But even if they were still employed elsewhere, we'd tell 'em to take a holiday and we'd pay them extra for a week, you know, um, and come and spend 5 days in the business and get a feel for it. We, we want to know you as much as you need to know us. And let's see how we would work, how culturally it would fit. And that was a non-negotiable for anybody kind of mid-tier management or above.
That's fab. And did you ever have people saying, no, I'm not going to do that?
We did. We did. I would say probably 1 in 2, 1 in 3 would say that actually, because they're like, oh, well, I don't want to waste my— I can't take my holiday, or what do I say to my employer or whatever? But actually, you just wean through people really quickly.
Yeah, they weren't really serious. They weren't moving for the mission. They were moving for the money or what they didn't really like you, they just like you a bit more than the other company. It's not—
Yeah. You can weed through people really quickly. Really, really quickly. Yeah.
And what's your definition of, as you go from say founder to CEO, right? And it's all on you, eye of the storm, and then it's not. What are the things that you think founders should keep a hold of as they become the CEO? What's the job of the CEO at 90 people? And maybe there's 2 things. One is there's a generic answer and there's the Luke answer. What's your superpower? And is that the same as other CEOs that you see?
Yeah, I think kind of the generic answer would be giving up getting into every detail of execution, of course, and finding people to do that, like handing that off to people. From my perspective, I still wanted to hold on to relationships and a lot of the sales process because that tends to be a fairly strong part of mine. I've had a commercial background throughout my career and I enjoy that piece. So if it gives you energy, then I think it's a good thing to do. You don't want to do something that's not going to give you energy. So I try and hold the relationships as much as I can, not obviously from an account management perspective, but from a new business perspective, and then find great people like CEOs or whatever to take on and and look after the rest of it outside of that. And that's always worked for me. And actually, this new business I launched, for example, with a COO in place day one, she's effectively managing the business day to day, and I've just brought in really senior people from day one to allow me to be much more strategic.
But you still own the vision and therefore the sort of product or service specification and standards?
Absolutely. Yeah, yeah, I set, I set that from day one, and I think that's critical, and also stay very close to that. So we're building out our own frameworks, methodologies, ways of working, um, and I still sit very central to that. But then once I've delivered that as a vision and an expectation, as a framework, then it's for other people to implement.
And how do you, how do you know, how do you know that they've that they're doing it as well as you would like? I mean, as opposed to stumbling across it later to realize that they're not.
Yeah. I mean, look, you're not always going to get that right. And there will be some things that go through the cracks, but I think there are things you can do to protect yourself from that. So I have weekly check-ins with the CEO, COO, and the rest of the team. I track overall results from an output perspective for our members, as we call them, basically effectively our investments. So I think staying close to it, but not in it is the key.
Yeah. Okay. And what do you— so what do you— is the team office based in London and you're in Portugal, or are you fully remote?
Fully remote, actually. We do have a small office in London, which we meet in periodically. Most of our our members or our partners are spread out across the UK. We've got some in America, one in Ireland. So again, it works better for us to be remote because of their locations. But we do 2 get-togethers a year. So we've actually— end of next week, we've got our first meeting of the year. All the members come together. We bring everyone into the same location, doing it in the UK this time. And then we do a retreat later in the year where we get everybody together for a few days as well. And we spend a few days offsite, leadership coaching, training, everything else. So couple of really good in-person events a year, and then the rest of it is, is pretty remote, which works for us. Okay. And have you—
were your earlier businesses all in office? And then did you transition to fully remote? And yes, why? And what did you learn?
Yes, they were. They were all in office. Don't get me wrong, you know, there are trade-offs in this. And, you know, I speak to a lot of founders about this day to day. I still like—
would you, would you prefer your investments to be office-based or fully, fully remote?
Hmm, a bit of both. I mean, look, I've got investments in both setups, right? I think there's an element of— and I think what it comes down to, of like, there's an element of controls in place if you've got people in one location. I think every deal, that's what it comes down to. However, if you hire— again, it's about hiring the right people that are self-motivated and disciplined, etc. And then you, then you can get good output from remote staff. I think a hybrid model or a blend is still the favorable approach. So if you do have that ability to be together a few days of the month or a few days of the week, like I think that is pretty healthy. Um, but look, you know, for us it works, it works well. And, and this is the first business I've started that is fully remote. Um, the last agency model, you know, at Kadastri, when I sold into those guys, we had 1,200 staff globally and 2 huge offices in Brazil that nobody went into, and 1,200 staff darted around in their houses. So all over the world, which was my first real insight into how it could work at scale.
Um, yeah.
And they've got no, no ambition to pull people back to offices. You know, it's there as a drop-in, it's a hot desk type situation now. They sublet out some of their units that they're not in. Um, and it's like, look, you know, come in, use the space. If there's client meetings, we use the space. Otherwise, to get the work done. And it's about trust and visibility. And I think from a lifestyle point of view for employees, let's be honest, having that type of approach is better, but it's about, can the employee actually be self-motivated? And that's where there are challenges still. Yeah.
It's interesting because in my early career, I decided to not take a job because I didn't think I had the self-motivation to do any work if I wasn't turning up somewhere 9 to 5. And so opted to be in an office. I wanted to be in with people and I just didn't trust myself.
Yeah, I think there's the cultural piece there as well, isn't it? People get a lot from being in the office. I sometimes miss it as well. I'll go and work in a coworking space down the road every now and again because I just need to be around a bit of hustle and bustle and you want that feeling. So look, I think there are trade-offs on both sides. And I think both models have a place. It's personal preference, isn't it? And about the people that you hire. I think for junior staff as well, bloody difficult to get started in a world where it's remote, trying to get the support and the training and those kind of watercooler conversations just aren't there, are they? So that's difficult. That's difficult.
Totally. I think it's a real miss. Yeah, I know.
Yeah.
Um, the sort of junior people that I know, you know, we've got somebody in the office here who's 20, and I just think if she was on her own at home, the conversation, you know, she catches me 10 times a day to just ask me something, and that just, she wouldn't have that opportunity. She wouldn't be like, she just wouldn't, you know, she might, she might, you know, Slack me or WhatsApp me or something, but it just wouldn't be the same. It would be dead easy to Ignore those messages and not give her the input that she needs. So look, talk to me about leadership development if you can, because you've got your own experience with your own businesses and you've got these multiple investments. And I have a thesis, which is no company outperforms its leadership team. And so what have you learned What do you look for in investments and how do you help? How have you helped your leadership teams to scale and how do you help investments, the teams you invest in to scale?
Yeah, I think it's a constant iterative process, right? Everybody always has something to learn and something they can improve on. So enabling good training, mentorship, access to ongoing support is part of the the, the key. Um, one thing I look for when I'm talking to founders or potential investments is how malleable are they? Are they open to suggestion? Are they, you know, do they feel like they've got it all figured out, or are they humble enough to be like, well, actually there's a lot here I need to do in order to get to the level that I want to get to, like, help me map out how I do that? And most of that, or a lot of that, comes down to, you know, how they execute, training them, giving them support, you know, and really giving them the ability to keep expanding as a leader. And I think that's the key. I mean, from my experience today, I still have coaches, business coaches now I work with, and all I do is each time I move to a new room or a new level that I feel like I've achieved, I'll go and find somebody that's in the one above me and ask them how they got there and what they did and look for answers. And I think that's the key. If leaders are curious and they continue to be curious and always striving to be better, then I think you've got a good one on your hands.
Okay. And can you coach curiosity into somebody or is it an innate thing that's there? I mean, I suppose what I'm asking you to do is to think back about the people who failed and Were any of those failures a result of curiosity? And did you try to make them more curious? And did you succeed ever?
I think there's certain character traits that are really hard to train into people if they're not there. I think there's a reason why you can probably look at good leaders and start to understand the types of traits that make a good leader. And that's just because there is a character piece to it that you can't you can't make up and you can't fake. And I think you've either got it or you probably haven't got it. Um, I do, I do believe that if people are genuinely open and malleable, that you can make them the best version of themselves that they could ever be. But, you know, can you, can you create character traits in people that weren't there? Maybe with enough time and enough curiosity and enough want, but I, I haven't seen it. You know, the problem is people And especially as we get older, people, you know, those character traits are ingrained, aren't they? They're harder and harder to undo. Um, so yeah, I'm not sure. I've seen a lot of people that have on the surface wanted to do better and wanted to move up and into management roles and into leadership roles. Um, but when that pressure unfolded and they realized the difference, um, that needed to come with that and that kind of piece of separation that you need in order to manage people versus lead them. There is a big difference between managing and leading.
Define that for us then, that difference for you in terms of managing and leading.
For me, I think one of the key things I see in good leaders is that they are willing to— they're the type of people that would be willing to do any job they ask somebody else to do, they will have done themselves. And they're quite happy to show that they lead by example and they lead by doing rather than It's that kind of show, don't tell piece, whereas managers often tell, don't show. And that's a kind of generalist sweeping comment, but you see where I'm going with it. It's very much inspiring rather than telling.
Yes. And you could link that to the whole doubt, curiosity. I don't know if you think of the medical training, it's see one, do one, teach one, right? And so, if you are going to have to lead a thing and you don't have the skill, Well, get the skill and then, you know, or at least know enough about it. And again, it comes back to curiosity and it comes back to the thing we were talking about earlier. It's hard work. And people go, oh, I'd love to be a, but it's hard work. So I'm not going to. Okay. Luke, what books have you found helpful, useful along the way that you think other people should pick up?
Oh, there's been so many. One is Never Split the Difference by Chris Voss. I think it's a great book all around kind of negotiating. Skill that underpins kind of everything you do. It's a really good, really good read. Um, Psychology of Money, um, that's a fantastic book if you want to understand. It's not just about, about money per se, but it's about the discipline of compounding and how your daily actions and, um, your decisions compound over time. And it's really good from a money perspective, but also from a habit stacking perspective. Um, and then probably, um, The Obstacle Is the Way, Ryan Holiday. Really good book as well. Um, practical kind of reframing adversity, um, kind of fits a bit into the doubt piece I was talking about earlier. Um, but really good book if you want to look at kind of how you can practically overcome some of the adversity that a lot of us feel day to day.
Fantastic, Luke. That's brilliant. If people want to get a hold of you, Find you on LinkedIn or—
Yeah, LinkedIn's a good one. I've got a website, luke-tobin.com. You can join our Success Method newsletter on there. We've got 120,000 subscribers now receiving weekly newsletters from us, effectively all about frameworks for improving yourself in business and in life in general and kind of the success hacks that you need to continue growth.
Luke, that's absolutely brilliant. Thanks for coming on.
Thank you for having me. Cheers.
Next time.
So you want to be one of the world's best negotiators? Here's the thing.
Here's the trade secret. You need to practice it. But by you having the courage to raise it first, that shows a lot of understanding and it helps the rapport building where the other side to go, you know what, even though this might be at To Scott's detriment, he's raising this. You've got to get yourself into the right place first emotionally, because if you're rankled, if you're irritated or frustrated with this person, that is not going to end well. You've got to be the right person to have the conversations where you may not be.
Techniques or tools or tips have you got for somebody thinking about how to get it done?
There's a number of things there. First of all is
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