Nick Astwick: CEO of Southern Cross Health Society

Posted on 17 Apr 2026 in Featured, Podcast

Nick Astwick: CEO of Southern Cross Health Society

Join Paul Spain for a compelling conversation with Nick Astwick, outgoing Chief Executive of Southern Cross Health Society. Nick shares his journey from a Christchurch schoolboy who once dreamed of joining the police force to leading some of New Zealand’s most influential organisations.
Drawing on his experience helping to launch Kiwibank and guiding Southern Cross Health through major strategic transformation, Nick offers hard-won insights into leadership, building intentional cultures, and creating high‑performing teams. He reflects on the importance of aligning personal purpose with professional success, leading with intention, and his vision for New Zealand’s high‑growth business future.

The New Zealand Business Podcast is brought to you by One NZ and Gorilla Technology.

Listen to the Podcast Here:

Apple Podcasts YouTubeMusic  RSS Feed

Paul Spain – LinkedIn
Paul Spain – CEO, Business & Tech Commentator, Futurist

You can keep current with our latest NZ Business Podcast updates via Twitter @NZ_Business, the NZ Business Podcast website.

Episode Transcript (computer-generated)

Read more

Paul Spain:
I’m your host, Paul Spain, futurist and chief Executive at Gorilla Technology. I love to see individuals and their organisations thrive and the New Zealand Business Podcast is all about this, helping you learn from our most innovative and tenacious leaders. Today I’m joined by Nick Astwick, the outgoing Chief Executive at Southern Cross Health Society. Nick’s story encompasses his journey from Christchurch schoolboy with a dream of joining the police force to an impressive management and leadership career in New Zealand and the United Kingdom. Nick’s drive, grit and determination assisted him in each role, whether it be helping launch the Kiwibank brand, his rise through the ranks to become their Chief operating officer in 2012 before he took on the Chief Executive role at Southern Cross health society in 2017. We also hear about what’s ahead following his recent resignation from leading Southern Cross. The New Zealand Business Podcast is proudly brought to you by One New Zealand and Gorilla Technology.

Paul Spain:
Before we jump into the interview, a quick question to ponder. How confident are you that your mid size or smaller organisation is is appropriately leveraging artificial intelligence and other tech? And have you got your house in order from a cyber security perspective? If you’re not sure, get in touch with Gorilla Technology today to learn how a tech or cybersecurity audit could help you. Alright, let’s jump in. All right, well, greetings and welcome along to the podcast. Great privilege to have Nick Astwick joining us today. How are you, Nick?

Nick Astwick:
Thanks, I’m great, Paul, and thanks for having me today. Looking forward to it.

Paul Spain:
Yeah, well, always like to start at the beginning. So tell us a little bit around where you were born and where you grew up.

Nick Astwick:
Well, I was lucky enough to be brought up in Christchurch, in Canterbury, so I had the classic provincial upbringing in the south island, you know, on the sports fields of Christchurch. Fantastic in the cold and I guess the Nor’, westers, but very lucky. I had a great childhood growing up in provincial New Zealand. Born in 73. Yep. Left there about 94, 95.

Paul Spain:
Fantastic. So what were the hallmarks when you, when you look back at those sort of younger years of the things that you got, you know, stuck into that maybe connected a bit with later life, whether it’s leadership work, business, other kind of interests that you’d see kind of connecting up.

Nick Astwick:
Well, on reflection, I do trace a lot of the way I roll in my life today, whether it’s as CEO of Southern Cross, from that provincial upbringing. I mean, I think I, you know, we’ve all done those, you know, tests around how you think. And I’ve got an achiever mindset. So I’ve always been intentional, wanting to achieve. And that’s come from the sports fields, I believe, you know, and a competitive sport, you know, in provincial New Zealand, relationships do matter, you know, whether it’s on the sports field with others. So the ability to build relationships and work collectively is critical, I think, to leadership today. So sort of that intentionality, the ability to work with others, you know, that ability to, I guess, that community and cause has, you know, shaped, I guess, a lot of my leadership career today. And, you know, it’s been a great privilege, but it’s actually been quite foundational.

Paul Spain:
So when you look back, tell us, what did that sort of sports journey look like? What sports did you play and, you know, how did you do?

Nick Astwick:
Well, I was into everything, basically. I was Christchurch boys high lad. So in the sort of. When was that? That was 87 to 91. The Mertons and the Chris Cairns of those days went through Christchurch boys. And so I played a lot of cricket. Love cricket. First eleven, played a lot of football in those days for clubs.

Nick Astwick:
I ended up playing a lot of indoor cricket at those times, but it was triathlons and things like that, you know, in those. I think Christchurch was a wonderful place to be active. Yeah. And I gave it all. And it was. It wasn’t just the achievement in the sport, it was doing it with others. That’s what I loved. I loved team sports, the ability.

Nick Astwick:
And I sort of deeply understand in the Crusaders philosophy, a champion team will always be the team of champions. And I believe that to be absolutely true. That the culture of a team, the growth mindset, the challenging pursuit of excellence, the confronting the stuff that’s stopping us being excellent, but in a acknowledgement, not judgment way, is critical. And so sport gave me that.

Paul Spain:
And did you build something of a work ethic in terms of, you know, doing jobs and work as a youngster?

Nick Astwick:
Yeah, I did the paper round. I was the Tuesday to Thursday hour, rain, hail or shine, and Christchurch had it all.

Paul Spain:
Oh, yes.

Nick Astwick:
I would get out there, but I was brought up in a family that worked hard. I think that work ethic came from, you know, your values are largely. And your beliefs are formed in those earlier years. And they’re formed by the experiences you have. And so I was lucky enough to get great values. You know, I hated going out at times, but I did it. And so there was that really strong worth ethical around the paper round. I worked, you know, umpiring indoor cricket, which was late at night.

Nick Astwick:
So it was really, you know, my school was everything, but I would do the odd jobs around there. My first real gig though was with the national bank in island branch University Canterbury.

Paul Spain:
Yeah. Okay, well tell us about your university time, your study.

Nick Astwick:
Yeah, it was one of those ones that sort of fell into. I mean, I wanted to stay at the University of Canterbury. You know, a lot of my mates were there. I sort of, from school, I had this bent for business. And so commerce was the obvious thing that I wanted to do. I did a side of Japan. I’d studied Japanese through high school and I wanted to keep that going. And I did spend six months on a ski field in Japan to really practice it.

Nick Astwick:
But having that sort of yin and yang of business and I guess learning language and culture was really powerful for me. But I was very intentional around a commerce degree. I didn’t want to be an accountant. I sort of majored in accountancy and things like that. So as you well know, I was sort of doing that in the pursuit of this sort of weird idea that I would become a detective at some point and a policeman. And then I sort of gapped a job in the national bank and the rest is history.

Paul Spain:
Yeah, yeah. So, yeah, tell us about that. You know, what that looked like to get that role at national bank and you know, what you were doing right at the beginning?

Nick Astwick:
Oh, right at the beginning, I was a teller. Yeah, I, you know, I was sort of a. A young bloke in Canterbury, commerce degree, saw an opportunity at the national bank and just seized it. So, you know, I spent I think six months as a teller. Yeah. And I fell in love with, I guess, the service ethic, you know, serving others. I really actually enjoyed, you know, I got yelled at for asking somebody who’s been there for 30 years for their ID. But actually learning from that was critical.

Nick Astwick:
So I fell in love with first the sense of service. I actually really enjoyed financial services. I think not the products of financial services, but the impact of it. The ability to have people in homes or to build their wealth creation or just survive university and actually really enjoyed the financial services componentry of that.

Paul Spain:
You’d mentioned this interest in joining the police force. How strong was that and what, you know, at what point did it tweak in your mind that actually, you know, you weren’t gonna, you know, pursue being in the police.

Nick Astwick:
I think the quality of thinking was quite low in that one. I sort of. I did it because I sort of grew up with a lot of the Christchurch boys. High dads were in the police. And so there was that sort of hero. I want to be like that. But it dissipated pretty quickly. It dissipated pretty quickly.

Nick Astwick:
I think I found my love in the service and financial services pretty quickly.

Paul Spain:
And what did it take for you to, you know, progress within. Within the banking environment?

Nick Astwick:
I think there was, I guess my achievement mindset was there. So six months Teller banking consultant, you know, so it was probably 18 months in the branch. Loved every moment of it. But when I saw the product manager, Roland Wellington, I said, that was for me. Yeah. And so really I was quite ambitious in that sort of stuff, as you are when you’re a bit younger. I said, okay, I want to make more of this. And so I applied that role in Wellington and got that out of the branch.

Paul Spain:
Was that the first different thing that you applied for?

Nick Astwick:
Yeah, that was actually the first one I applied for. You know, I love the ethos of the National Bank. It was about customers first. You know, we’re here to serve. They really understood the value driver in banking is actually tenure of customers, not margin. They were very people centric to serve customers. So they really understood look after the people, look after the customer, look after the shareholders. I felt like that was a culture that I could be myself in.

Nick Astwick:
And so it was very. I said, that’s the brand I want to work for. What’s the next gig? And it was that one in Wellington.

Paul Spain:
And who was it within the bank that taught you that? How did you learn that? That was what the bank was all about and that was the culture. How easy was that? You know, picked up?

Nick Astwick:
Very easy. I mean, I think what I’ve learned in my careers, culture is the critical success factor. Not just a good one, but the right one for the strategy. And my definition of culture is what does the leadership care about? That is the culture of any organisation. And so what I got to see at a very young age, I had access to the leadership of national bank and you could tell very, very quickly what they care about because it is the context for their decisions. And the culture of the national bank was very visible through the actions and distort of the leadership.

Paul Spain:
And was this access to the leadership once you’d moved to Wellington, to Wellington,

Nick Astwick:
to the head office. That’s right. Yeah. Okay. And so, yeah, I had about three years or so in Wellington for the national bank and the national bank. And the learnings in those three years still is in the frontal lobe of my leadership today.

Paul Spain:
Fantastic. It was the senior leadership that you were really able to learn from or was it across the board? Cause how many, you know, how many layers of people were there? I guess, you know, it wasn’t such a big enterprise as our banks are today. Right.

Nick Astwick:
No, yeah, I can’t remember. I probably was fourth or fifth level down, you know, sort of mid management in those days. But I can tell you at the age, a ripe old age of 22, I was looking after the whole deposit side, which is half of the retail bank. Yep. At a very young age. And so I had access to, to the treasurer, I had access to the head of the retail bank, you know, and so it was a very tight. Yeah, but it was a very flat structure in that sort of sense. And so access to leadership was, was pretty obvious.

Nick Astwick:
I was green as anything as you can imagine. But I had a, you know, I had a growth mindset. I just wanted to consume and learn just how it worked at that, that point in time.

Paul Spain:
Yeah. And then what was, what was next after that three years in Wellington?

Nick Astwick:
Well, I wanted to do the classic OE, so I did the classic OE. I left in 1998, went to London. My dad’s a Yorkshireman and so I had the British passport and so I spent five years in total with two stints. Yep. Over in London and loved every moment of it. I worked for UBS Warburg, the investment bank there. We did some cool stuff like the euro conversion program that was trillions of legacy currency positions had to turn into the euro in a 12 hour window. And it was only Kiwis, South Africans and Aussies crazy enough to take on that challenge.

Paul Spain:
Yeah, I remember doing a little bit of work in London and it seemed to be sort of. Yeah, Kiwis, Aussies and South Africans were very well sought after. And in fact I did some work at a bank as well. Mine was a very short stint in between things. So that sounds like some real pressure to get that right.

Nick Astwick:
It does, but it was my first exposure to, I guess a non movable program where you’ve got to build a culture that has to deliver successfully. I mean the stakes are pretty high if you don’t. And we did it. And so I felt like at that point in time it was a really good learning of what it takes on one of those sort of critical projects. To get it right.

Paul Spain:
Yeah, yeah. And what do you think you took away from that, that experience?

Nick Astwick:
Well, it’s very similar to the sporting analogy. You gotta know what good looks like, you know, what is success well defined? You’ve actually gotta build a team that fundamentally is not. I think we’ve had 60 in that team that doesn’t work in 60 different directions. It has to be bought in to the cause and the purpose and the outcome. And so therefore it has to work as a collective, not as a set of individuals. And so that leadership is fundamentally into that one. It had to have a good dose of two things. It had to have a good dose of management, the how are we going to do it? But it also had to have a good dose of leadership.

Nick Astwick:
It had to get people to rise up, you know, to achieve the outcome, and you had to be motivated and willing to put in all your discretionary support to do that one. So I learned, I probably learned for the first time the difference between leadership and management at that point in time, you know, and so that was the lessons that were certainly learned there.

Paul Spain:
And so how do you define that today in terms of the difference between leadership and management?

Nick Astwick:
Well, if you look at. Well, leadership and management fundamentally are critical bedfellows, but leadership is ultimately about the why and what. It is around the medium to long term. It is around people and motivation, whereas management is about the how. It is about the execution of plans and the development of plans with sort of discipline. And so, you know, one is about setting the direction and why we’re going there. The other is how we’re going to deliver it. And so for me, that should have shone the light on the difference between those two.

Paul Spain:
And what did the rest of that time in the UK look like?

Nick Astwick:
Well, I kept working for UBS World Work. I did a little bit of strategy for them around their operational excellence. And I think the. In a product manager, a marketer per se, in both of those, my role was really marketing, which is around the product, the price, the distribution, how you’re going to sell, you know, the four P’s. And so that is a lot of strategy. I mean, operations jobs were really about doing tasks, you know, when you were young, into a national bank, around the deposits and you had to raise $2 billion a year. You’ve got to start learning strategy. You’ve got to learn about developing a strategy to generate those outcomes.

Nick Astwick:
And so the gift I got through those jobs was being a good marketer, a good strategist. That’s what I learned over that Period of time. And that’s probably some of the skill sets that I’ve taken into my later career.

Paul Spain:
What were the biggest pressures that were on you at that time?

Nick Astwick:
Well, I think the Euro program, it was sort of a binary success or failure. I think the big pressures on me was really the quality of my work. I had a high standard and I’m unapologetic for that. I do. In those early years I felt like my self worth was attached to my work worth. You know, if I was successful at work, I was successful as a human. Yep. Now that unravelled a little bit of my later life and I needed to put a healthy attachment to that.

Nick Astwick:
But that’s what I measured my self worth on. Was I successful at work? And so I’d always strive for high standards. I was also always strived to make sure that I produced what was sought by the leadership of the organization. But I was all in.

Paul Spain:
What was it that brought you to the end of that overseas experience and decided to bring you home?

Nick Astwick:
My love of home, really. I mean I worked five years for the UBS Warburg in two stints. I had a little stint back home, but I don’t think I heard the word customer mentioned that often. Yeah. And so for me I was a bit disillusioned with the machinery of banking and the politics of it. I had to make a decision at that point in time with now my wife is where do we want to spend our lives? And for me, you know, I thought long and hard about, you know, 20 years in London working through, working for the man, as they say, or actually coming back home and making a dent for New Zealand. And that was my personal context. I was very lucky to meet Sam Knowles and Paul Brock and Kiwibank had just started.

Nick Astwick:
I was looking for a startup and that was a real fortuitous sort of meeting at that point in time.

Paul Spain:
Yeah. So tell us how that came about.

Nick Astwick:
Well, yeah, I landed back in New Zealand looking for a startup. We wanted to spend our time back in Christchurch. Again that was in Wellington. So it was a very short move to Wellington. But when I heard about the opportunity to set up not just a bank but a brand that was rooted in the prosperity of New Zealand. One Kiwi after another and that no one wanted a bank, my marketing sort of, you know, just fired. I said, okay, this is a wonderful once in a life opportunity. It may fail miserably, but I wanted to be part of something that was significant for New Zealand and at that time that was Kiwibank.

Paul Spain:
Yeah. For those that don’t know, you probably can remind us who was it one political party or a particular politician that kind of really pushed for that to happen.

Nick Astwick:
Yeah, it was Jim Anderton in those days. Yeah, I mean, but also too New Zealand Post had a business strategy for its relevance, you know, around. Okay, how can it diversify? So there was the New Zealand Post diversification business strategy, met Jim Anderton, you know, from a political perspective. And the rest was history at that point in time. But I mean, it didn’t have the nation behind it, it didn’t have all the politicians behind us. Yeah, it was one of those. No one wanted another bank in New Zealand. And actually I don’t think New Zealand thought banking as strategic at that point in time.

Nick Astwick:
But remember in 2002, the only innovations really in banking was an ATM. You know, if you think about. And I go 2002, there was no mobile phones, there was no text messaging, there was no open the bank 24 7. It was still locked into the nine till four. And so you think in just 24 years, just the transformation of banking through the digital age was quite. And I saw that ride through Kiwibank actually challenged banking and what it stood for, not the banks. And so it was first with mobile banking, it was first with text banking. It was open seven days a week in some parts.

Nick Astwick:
So it really sort of challenged that psyche and the tradition of banking at that point in time.

Paul Spain:
Right. So where was kiwibank at when you joined? How far along in the development?

Nick Astwick:
It was about eight or nine months. I think it could have been somewhere between six and 12 months from landing in market, sort of still in post project phase. But I would just say it had just launched. And so I got that crazy five years of the startup. Then there was a five years of, oh my God, we need to actually turn this into a successful business because a successful startup and a great business, not the same thing. And so we had to go through that growing pains phase. And look, I’ve been out of Kiwibank since 2017, but I’m still very proud that there is a Kiwi bank. I think banking is really important for all banks in New Zealand.

Nick Astwick:
It’s still really important. It still, it does be a fuel of prosperity for those who want to seek it. And so yeah, it’s great to have that as part of our banking landscape.

Paul Spain:
And how hard was it to build a culture in an environment where you’re building this bank? But there’s really the connection into New Zealand Post in terms of the New Zealand Post Stuff being the front end rather than, you know, I guess what you experienced at national bank where you know, there was a very, a very clear culture, you know, across the board. Whereas I guess you’ve got this kind of, you know, crossing of two entities. Maybe you can just walk us through, you know, what, what that looked like to build out the culture.

Nick Astwick:
No, I think it was very, very intentional from day one. I mean the, I believe personally that Kiwi bank would have failed if we just tried to compete against the individual banks with better products. I mean we had to build a brand first. We had to build something. What do we stand for and what do we stand against? And so we were sort of challenging the notion of banking and how it’s been. New Zealanders have been underserved and that was what we were challenging against. So we had to build a brand first. We actually, the cultures of the two organized were completely separated from day one.

Nick Astwick:
So yes, you could see that Kiwibank lived in a New Zealand post branch for a while there, but actually behind the scenes it was completely separate. And that was very intentional. We needed a certain culture that was different from New Zealand’s post culture to be successful. And so that was separate. So I think the leadership of the bank was very intentional around what culture do we need to be successful in market and they design for that.

Paul Spain:
And then how did that play out when you had the branches sort of operating, I guess, using New Zealand post staff? Is that how that certainly.

Nick Astwick:
Exactly. Right. I mean it’s been almost unheard of that a bank can start up and be profitable by year three and Kiwibank was. And people forget that no bank has stood up and been profitable in year three. That was because we could leverage the infrastructure of the post network from a physical sense. And so it was actually a variable cost to Kiwibank and a marginal cost. New Zealand Post was quite sort of innovative in those days. I mean, when you look at successful scale businesses today, they partner well.

Nick Astwick:
Yep. That is the growth rate. They don’t try and do everything. And so, you know, we started with $80 million worth of seed money and we became profitable by year three or four or something like that. And so that was because we were smart around the business model. Now, obviously, quite rightly, the decisions you make at startup are different in time and as you can see, I mean, tell you what, the branch network model, yeah, has fundamentally been disrupted over the last 20 odd years. And so I think it was a great entry point and it allowed us to evolve the bank over time and Actually, the great thing about New Zealand post was just about in every single region, you know, and every single town and every and large amount of the suburbs of the country so we could get reach very, very quickly.

Paul Spain:
Yeah. When you, when you look back at that initial kind of, you know, startup phase, what was the biggest challenge that you were facing at that time?

Nick Astwick:
Terminal failure. It was, wasn’t it? It was, I mean, it wasn’t like there was a million New Zealanders saying, I need a bank. I mean it was a binary outcome. This was either going to be a success or it was gonna be a dismal failure. And so, but something, you know, might be blind ignorance, but actually something within a small few amount of people wanted to sign up for that job a little bit like the Euro program. And I think what I’ve learned in myself, while I have achiever mindset, I do have a reimagining mindset. I do can see a vision, want to be part of something that is meaningful. And so I signed up to that.

Nick Astwick:
But you had to be very intentional and disciplined. And you know, I learned in my early marketing career that the market buys different, it doesn’t buy better. And so you had to be very clear about how you were different and that building a brand that sort of had the Kiwi psyche, challenging banking, creating a cause and a purpose and delivering, you know, great experiences at the time that were different was really a little bit of the recipe of success. But I was just part of a team of a hundred, you know, that really did that. But it was one of my favourite times by far.

Paul Spain:
And so what was your role at the outset?

Nick Astwick:
Oh, I just started, you know, I was largely came in doing some of the market componentry for them. Head of markets rapidly moved to running sort of the consumer division. And so it was a rapid rise through the ranks. But, you know, it’s one of those classic things. You go away for London, you do some big stuff and New Zealanders go, well, that doesn’t really matter. You know, London experience is not seen by a Kiwi as anything valuable. And so it was really just getting in on that ground floor and then just going for it. And so as I say, I think I was on the executive team, I think there around about 2007 and so had 10 years as part of the leadership team at Kiewa Bank.

Paul Spain:
Yeah, fantastic. And what were the key learnings over that, you know, that period for you? What were the things, when you look back now that laid the foundations for moving into leading Southern Cross and the work that you’ve done there.

Nick Astwick:
I think a lot of it was developing my leadership competency. You know, I was still a manager for a long, long period of time. So what I learned is sort of how to lead a culture, you know, a culture that was right for the strategy at that point in time. So that was clear. I mean, what I learned largely through my Kiwi bank days is the role of leadership is to intentionally care about the things necessary to lead a culture that’s critical for the strategy and to hire people with the beliefs and the values critical to the culture. So that right strategy, right culture, right people was fundamental to me. But I also learned that leadership, you know, there’s three big traits and I learned that through Kiwi bank and Leadership New Zealand. When I look at great leaders, they’re very intentional.

Nick Astwick:
They take action. Yeah. They don’t stand on the side. They actually sometimes have to get in unpopularly and they have to lead and they have to put themselves in vulnerable positions, but they do take action. You know, great leaders are very self aware. They understand thyself, the good and the bad of it. Yep. They understand and they play to their strengths.

Nick Astwick:
Yep. And they can understand their vulnerabilities and weaknesses and they put teams around that. And the third thing, they, they are very reflective. They learn from their mistakes. Yep. They can adjust their style in different circumstances. And I think for me, Kiwi bank leadership New Zealand, sort of, sort of ground what good leadership looks like. And actually how do you make a high growth business? How do you actually cut through and get high growth, but also too successful startup is not a great business and I learned that from sort of the great leadership of Kiwi bank and the national bank in those days too.

Paul Spain:
Now you talked about self awareness. How did you develop that?

Nick Astwick:
I think lots of people can tell you. Well, I think first you’ve got to care about it actually. Do I know thyself? I mean we all go through hundreds and hundreds of assessments, but you’ve got to, once you wise up a little bit, you think in the young age you can do everything. And you learn pretty quickly that playing the same style in a different situation turns into failure. And so you’ve gotta refine your leadership style and your impact. And so that only comes from reflection. Why did that not work? Okay, I led in this way and so I think you’ve gotta have a growth mindset, you’ve gotta confront the realities of failure and you’ve gotta really then refine and deliver that into the future. So for me, just big learning journey and good doses of reality.

Paul Spain:
And how do you help others recognise maybe they need to become a bit more self aware along the way?

Nick Astwick:
Well, it is charity with clarity. I mean, one of my swing thoughts is how do you treat everyone with respect, but be clinical in what you expect? I mean, if you genuinely care about somebody. Yeah. Then you’ll help them be better. I feel like that’s the role of a leader is always to be a coach. Yep. Is to get, I mean, a coach is trying to get from within somebody the greatest potential and you need to be able to help people understand their strengths and weaknesses and support them. But that’s gotta come from acknowledgement, not judgement.

Nick Astwick:
It’s gotta come from care, not critique.

Paul Spain:
Now, you mentioned earlier around understanding where your self worth comes from and that, you know, initially that was probably tied.

Nick Astwick:
Yes.

Paul Spain:
Very closely to your sort of success in the workplace. How did you evolve that, you know, your thinking in that area over time? Were there any particular, you know, triggers for you or things when you, you know, when you look back that helped you to develop that understanding that, you know, you should have self worth, you know, regardless of, you know, what’s happening in terms of, you know, career?

Nick Astwick:
Well, I just developed a very unhealthy attachment to work. I started with, like most young people do, you have successes in your early career and then when you get higher up the stack. Yep, there’s failures. You can’t control everything at that point in time and so then you get drawn down. So my whole self worth sort of collapsed when failures. I am not great. I got quite vulnerable, sort of, in a sense that. And so I actually, with a coach, had to say, why am I feeling like that? And he pointed out that I had an unhealthy attachment to work.

Nick Astwick:
And so pretty much from that moment on I separated my two worlds. And in my role as CEO, I often say, you know, the business has got this challenge and the business has got this success. Nothing to do with me. And so, you know, you’ve actually got to learn to put big distance between that. But if you’ve got a healthy attachment to work, you can really critique it. You can, you know, and I think one of the roles of the CEO is to define reality and give hope. You’ve got to be able to hold the truth, what is actually going on, because everyone in your organisation sees it. If the CEO doesn’t see it, it’s optimistic or pessimistic.

Nick Astwick:
And so having a healthy attachment allows me to define the reality of what’s going on and then it Allows me to objectively go, you know, give hope as what’s the good strategy, what are the good plans, what are the good decisions? And to give hope in the form of taking good action. And so I had to learn the hard way around a healthy attachment. But I see that in a lot of young people today. It’s not that they are highly iq, you know, they’re very intelligent, they’re very intentional, but they’ve got an unhealthy attachment that their whole self worth is attached to their work worth. And that does unravel. And so I try and help them sort of separate those two worlds.

Paul Spain:
Yeah, fantastic. Can you share a little bit about what the circumstance was that, you know, that brought you that point where you got a coach and you know, you re looked at things well, it’s just

Nick Astwick:
a sort of a, sort of a culmination of things that don’t turn out well, whether the system changes that do that or the market or there’s people that you’ve made judgment calls on that don’t turn out. So you go, oh my God, you know, that they are not all successful. And what I probably, you know, that’s where the learnings are and the tough moments, I can tell you. Yeah. And so there was a lot of learning there, but there was actually, you know, it was a culmination of many, many things over time.

Paul Spain:
And so that was obviously quite a key, you know, a key learning from, you know, from those tough moments. Were there any other kind of key learnings that came out at that time, you know, where you got a coach and so on, you know, going through these things? As you’ve said, there’s lots of learnings in there. What else could you share?

Nick Astwick:
Well, I think again, it was really about what leader are you going to be. It’s like a lot of people come in, I want to be the CEO. And my first question is, well, why do you want to be a CEO? And secondly is what CEO are you going to be? And thirdly, what organization are you going to be? The best CEO you can possibly be. And then they haven’t even thought about those sorts of things. And so I think my leadership career had taught me be intentional, be self aware. Yeah. And be highly reflective. And I knew that I would only be a great CEO in a certain brand or a certain culture or with a certain strategy.

Nick Astwick:
I mean, I can pay politics like everyone else, but I’m not at my best. Yep. And so that was a little bit of the story of Southern Cross, really was, you know, I Went for a CEO gig. Yeah. And I thought, oh, they’re gonna look at my weaknesses and I’ll.

Paul Spain:
I’ll.

Nick Astwick:
In my interview, I’ll manage my weaknesses and say all these. Right. Technical things. Yep. But I blew it. Yep. You know, I. I tried to be the person I thought that they were seeking, and they could see straight through that.

Paul Spain:
Yeah, yeah.

Nick Astwick:
And so then again, failure learned from that. And so then when I had the opportunity to the CEO, in fact, I went to INSEAD and did the advanced management program in Fontainebleau there. And a large part of it was thinking about the leader, you know, you should be, you know, about sort of, what potential have you got and how can you realize that? And so I came back from Fontainebleau with a sense that I just don’t want to be a CEO for the sake of being a CEO title. What I want to do is lead an organization that’s got this type of impact and meaning, and I think I’ll be the best leader in this type of culture. And so when I got to Southern Cross and I saw the opportunity of Southern Cross, I said, if you want somebody else, fantastic. Yeah, but this is the leader you’re going to get. And I could do it with humility and I could do it with clarity, but it was quite empowering not to again say, I must, you know, I must try and be the CEO there. I could be authentic and say, this is the CEO you’re going to get.

Nick Astwick:
I think it’s right for the time here. And as history would show, they managed to give me the job, which was wonderful. And this is, as I say, to have the national bank, to have Kiwi bank, and to have Southern Cross, I feel very blessed.

Paul Spain:
Oh, fantastic. And so when you went into Southern Cross, that was what, 2017?

Nick Astwick:
Yes.

Paul Spain:
Yeah. And so what were those things that made you, you know, feel that this was a really good alignment for you and that, you know, this was gonna be. This was gonna be good for everybody?

Nick Astwick:
Well, I think, you know, I grew up with Southern Cross. My mum and dad didn’t have a lot of money, but one thing they did care was the health and our education. And so Southern Cross was in my life, you know, not that I needed it. You know, no one, you know, needs health insurance, you know, when you’re young, really. But what it taught me is it was a brand that was really meaningful at that point in time. So that was born in 1961, Southern Cross, you know, I was born in 1973, so it was still, you know, early part of that, of course, I surrendered it when I was in my 20s and bulletproof. Yeah. But I came back to, you know, remember, health is actually quite meaningful and has a huge resonance.

Nick Astwick:
And so a large amount of New Zealanders say, actually I want to have some sort of control about access to health when I need it, I care deeply about it. It’s a little bit like private education and there’s more and more of your normal Kiwis caring about that. And so for me, the first thing was it was a brand of significance and meaning I’d just come out of Kiwibank and National Bank. So it was a brand of significance and meaning I knew nothing about health at that time, but I knew that it was powerful and it had a huge resonance. You know, mortgages and health, you know, there was a difference there. But I also thought it was quite a heritage brand. It needed a dose of contemporisation and energy. And if it was gonna be around for another 60 years, it had to really confront its brand, its proposition, and how it was going to be relevant for New Zealanders.

Nick Astwick:
And I felt like I could help with that. And so, you know, I’m coming up sort of just over nine years, this is the best job I’ve had and I have probably really learned about the health sector, but the fusion between financial services and health has been wonderful. But this is a meaningful brand for New Zealanders. I mean, we do. We fund 3.8 million health events every year. You know, a lot of people can complain to me about the price of it, but we exist to get our members the care they need and we do it pretty well, I think over 3.8 million and we’ve probably earned 60% of the market share and 70% of the health funding in the private market. We’ve earned that, I think, because we run a good business and we deeply care about our members health outcomes. And I think for me, I feel at home in brands that really are good for New Zealand, are very customer and member centric.

Nick Astwick:
Yeah. And the culture deeply cares. And I think that’s what we have at Southern Cross, I’m very proud to say.

Paul Spain:
Now, explain how Southern Cross operates, because it’s not a business in the usual sense, it’s not a company, you’re a society. So what does that mean in practice, in terms of how you need to operate?

Nick Astwick:
The Southern Cross brand in New Zealand has two big business groups. First, it’s got what I would call the Health Related Insurance group, which is the Health, Life, Pet and Travel. Yep. Which I look I’m the CEO of the health insurance business and a director on those other product lines. But that is our financial services group, which I’m part of. And then we’ve got the healthcare delivery, that is your hospitals, all your JVs, all the white coats and delivering your surgery. Thank goodness I’m not involved in any of that. Yeah.

Nick Astwick:
And so you’ve got two, what we call funder and providers. We’re attached by a brand there, but they’re very, very different businesses. So the health insurance is actually what’s called a friendly society. There’s not many of us around, but what it largely means is it’s a profit conscious but not profit driven. It sits there. Yep. Not as a company, but as a friendly society. It’s gotta operate in the interests of the collective membership and it’s there to provision health, to be there for health and sickness, really.

Nick Astwick:
And so it operates as a company in every form of it. It’s just under our old legal structure, which means it doesn’t have shareholders per se, it gives a tax, we don’t have to pay tax. But that largely means that we can only do a tight scope of work. We can only look after your fund, your health and life orientated stuff. So it’s a very tight scope of business. But that’s a very old status, the friendly society status. But it’s like a mutual. I mean the best way I describe it is like a mutual.

Nick Astwick:
We’re here for the mutual benefit of the membership. Yeah.

Paul Spain:
Yep. So there’s not profits that are needing to be, you know, funded out to external shareholders. Everything really goes back into.

Nick Astwick:
That’s right. I mean, we need profits to have the capital to sustain ourselves. But we’re not driven by generating a profit, we’re driven by getting our members the care they need to get. Well.

Paul Spain:
Now, what did you find when you came in to the role?

Nick Astwick:
Well, I think it had good bones. I mean, a company that’s been around for, you know, 50 years already has got to have good bones. It had good bones, it had wonderful people, had a very causal based culture. But I think it lost its energy in its way. Yeah. And so what I could help with, I think was, I guess, bringing back a bit of ambition. You know, it hadn’t grown membership for 20 odd years. And so I saw I could bring from my Kiwi bank and national bank days, I felt like I could help them get this sort of growth mojo back, build a brand that was a little bit differentiated.

Nick Astwick:
I mean, there’s many organisations that are for good that go by the wayside. No one cares about your friendly society for goods legal structure at all. It cares about the quality of your experiences and products. And so as a result of a friendly society, we could be very customer driven. I learnt that from the National Bank, I learnt that from Kiwi Bank. And so that sense of making sure that we’ve got relevant proposition for the future and so a lot of energy has gone into making sure that that’s the case. And so I think just really modernising and contemporising, I guess what was a very heritage business has really been my role as CEO and to set it up for the next phase.

Paul Spain:
It’s been what? Nine, nine years?

Nick Astwick:
Just over nine years now.

Paul Spain:
Just over nine years. You know, if you’re looking in at say the culture side of the business, what are you most proud of in terms of what’s been achieved over that period?

Nick Astwick:
Oh, well, I’m most proud really that we have kept a customer centricity to the organisation. I feel like we’re a lot more modern organization than we were before. I feel like we’ve got energy and fight. Yep. And competitive nature to it. I do feel like we’ve got a plan and a strategy that will continue to make us more relevant into the future. But I’m really proud of, I guess, the culture of the organization. You know, it is a, it is a customer centric, caring can do cause based organisation and I think we probably just, you know, I do believe Southern Cross is a meaningful organisation in the New Zealand context.

Nick Astwick:
Health is very meaningful and I think, you know, I do feel a lot more comfortable that we can be around for 20 or 30 years. That that doesn’t mean to say that we don’t have to fundamentally still change and evolve. That goes without saying. But I do feel like we’re a lot more contemporary organisation.

Paul Spain:
What would you say you had to practically do in terms of stirring change and bringing change from that culture perspective and ensuring that everyone had that customer centric mindset and focus?

Nick Astwick:
Well, I don’t think our compete to win strategy was very clear. So I think the first thing, you know, define reality and give hope. We had to confront that just because we’re good, you know, that guarantees nothing. And so I think we had to confront our reality that our risk is irrelevance. Unless we’re relevant to, you know, close to a million members, I think we’ve got about 950,000 members. Unless we’re relevant to them in five to 10 years time, we’re a goner. And So I think confronting that reality that just because we are for good and our intention is pure, that means nothing. And so we articulated a very clear modernisation and contemporization strategy.

Nick Astwick:
And then we were very intentional around the culture that we needed. We were slow and methodical and so we became a scaled agile business. The leadership was focused on delivering the strategy, not running their businesses. We brought in some fresh talent and energy into the business but we were very intentional around that change. And so, you know, again, I think a lot of the systems were modernised. I think this is the thing, it was underinvested, I felt for a long, long time. And so we’ve progressively invested in its technology and I do think the moments of truth that really matter. You know, anytime I go out there with Southern Cross, I say you’re a Southern Cross member, what do you like about us? And they say at claim time, which is the moment of truth.

Nick Astwick:
You make it so easy. And for me, as a friendly society, no one cares about that. But what we care about is our members get what they deserve, what they are paying for in their policy each time not making it hard to give a profit to a shareholder. And that’s the Southern Cross difference is funding your healthcare when you need it. And so I feel very comfortable in an organization where actually the shareholder and the customer’s interest are fundamentally aligned.

Paul Spain:
And what did that modernization journey look like?

Nick Astwick:
A significant rebuild. I mean I think if all our systems now and all our providers to give instant decisioning your claim time. We’re trying to get rid of claims, you know, in an insurer. Yeah. We’re trying to fund all your, what you’re entitled to at the point of sale. So there was a massive amount of systems re engineering to get instant decisioning at the point of sale. All our mobile app and Internet was completely and utterly rebuilt. You know, I come from an Internet banking world.

Nick Astwick:
Yep. And so that’s why your mobile phone, you know, you know we feel like that’s your, my Southern Cross and your mobile phone. So we were, were very intentional around making sure that 24, 7 you could engage with Southern Cross. All our core infrastructure had to be remodernised. You know, if you think about we do 17,000 claim lines a day. You know, we largely do that instantly. Yep. Through you know, rules based engines and systems.

Nick Astwick:
And so that has to be 100% accurate, it has to be reliable, it has to be delivered every single day. And you know more than anything else, how technology becomes old pretty, pretty quickly. So there was a lot of modernisation of systems. Our whole information security posture and our resilience posture needed to be invested in. So again, it’s a lot of that, it’s like the foundation stuff you don’t see in your house. But we’ve had to strengthen a lot of that.

Paul Spain:
Yeah. So doing that has then allowed you, you know, I guess part of the same journey. But modernizing the core foundations has allowed you to have an app where people can do those claims quickly or with some health providers, GPS and so on, where they can manage that. Right.

Nick Astwick:
You don’t even have to, don’t even have to get involved, it’s just doing the core. Well, I’m a big believer in doing the basics exceptionally well and so we’re really focused on that.

Paul Spain:
And so what have been the results of that in terms of, you know, if you sort of, you know, look back to 2017 versus today, how do you measure that success?

Nick Astwick:
Well, I mean membership growth is quite a dramatic up, you know, I think it was about 700,000 and it got as high as 960,000. It’s come back in the last couple of years because. Cause obviously we’ve had a massive post Covid demand. So I think you can see that in the customer growth. You can see that in some of the net promoter score of our members, you can see that in some of the tenure, you can see that in some of the transactional volumes that go through. I mean I think the. So there’s some really good traits there, particularly our brand relevance in New Zealand. So I think we measure all those sorts of things.

Nick Astwick:
I think the challenge that we’ve still got is the affordability of our products and that is the, you know, to be relevant, you also need to be affordable. And so in our model, the more you use your pay, I mean for every dollar of premium, 90 cents pretty much in our model through the long term, goes back to pay your healthcare, only 10 cents in the dollar goes to our operating costs and that’s gonna get down to 6 or 7 cents. So pretty much where a money go round, your premium goes to your claims. And so fundamentally we have to make sure that over time the private system is actually sustainable. It does the right care in the right setting at the right time to make sure that it is sustainable. Because, you know, it’s not. You know, we contract with our partners, our healthcare partners. The price, your price is going up by inflation, but our members are using more and more services and so that’s a wonderful thing.

Nick Astwick:
Yep. But our members have to pay for It So we do have to make sure that the private health system actually does the right care at the right setting at the right time and does that efficiently as well as effectively.

Paul Spain:
What’s driving your, you know, your members, you know, using more health services, what are the drivers there, the spend is going up.

Nick Astwick:
Well, health insurance is slightly different. You know, no one says, fantastic, my house burnt down, I got to use my general insurance. And my, you know, in health insurance people join us for peace of mind, but they stay with us for value. And so there’s almost this sort of sense that I’ve got Southern Cross, I need to use it to get value. And so we’ve got 50% of our members that use it all the time in a sense, and 50% members don’t need to use it in any one year. Now that 50% changes. But there is a currency and a cadence to health insurance. And over time, you know, we exist to give you the care you need when you need it.

Nick Astwick:
That’s the reason for us existing. And so we do that 3.6 million times a year the next five or ten years is how we’re relevant to low claimers. I mean, that’s the thing in today’s world, you’ve got to be highly relevant to your low claimers. And so that’s a large amount of our work around our proposition.

Paul Spain:
And if you sort of stand back and look at how you operate versus, you know, for profit insurance provider, what would you say the big difference is? There’s obviously a difference in terms of how much of the funds that, you know, people are, you know, paying in their premiums, you know, gets used back for their healthcare. Right?

Nick Astwick:
Yeah, that’s exactly right. I mean, I think, I mean, I believe in having a competitive market. I think if you’ve got competition in your market is really, really healthy. And so we’ve got a number of competition. Some of them are like us, some of them are for profit. I don’t really, I’m not questioning motivations around there. I mean, we live and die on our value proposition. That’s what matters.

Nick Astwick:
So I think healthy competition actually gets you to be better. What I’m trying to do at Southern Cross, you know, I’m a deep believer that loyalty really matters, your quality of your experience really matters. And so we’ll make different decisions than others that may be product centric or operationally excellent centric, you know, and so really we’re trying to compete to be different. And so our difference largely manifests, I think, in our culture, like claiming for example, we just want to make that entitle your benefits. Yep. That’s our difference, is to make sure that we’re operating in your best interest, not the shareholder’s best interest every day of the week.

Paul Spain:
So what’s next for Nick astwick?

Nick Astwick:
Well, yes, September 30th. Yeah, that’ll be nine and three quarter years. As I say, best job I’ve ever had. Look, I’m just trying to been very spoiled with sort of National Bank, Kiwibank and Southern Cross. I’m looking to move more into a portfolio career to sort of get involved with high growth businesses that have got New Zealand Inc. At their core that really want to make a dent on the world stage. Yep. Or the New Zealand stage.

Nick Astwick:
And so I’m just looking for a little bit more variety. You know, I think being well conditioned as an executive to turn out, you know, seven o’ clock every day and you know, work. And so it’s just really trying to have more variety I think. And so there’ll be some professional governance roles that I’m really seeking at the moment and then sweat equity and some equity into high growth New Zealand businesses because that’s what I believe. I’m a big believer in the prosperity of New Zealand and I’m a big believer in business to try and give that, you know, we need more income as a country and we do need it to be more equally shared. That’s probably those businesses I just want to get involved in.

Paul Spain:
How big do you think the opportunity is for New Zealand moving forward and you know, how much of that opportunity is in sort of the high tech business world?

Nick Astwick:
Well, you can probably answer that better than I, but we’re building capital markets, we’re building an industrial mindset. If you look at halters and, and if you look at the rocket labs, the world has never been closer. And so if you’ve got the mindset that this generation does have, it can reach the world never. And when I grew up you couldn’t reach 7 billion people, but now digitally you can. And so I think we’re maturing, we’re finding some capital, we’re building a mindset that can scale. We can reach the world like we’ve never have before. And we’re turning ideas that we’ve always been very good at into large scale businesses. I mean we’re building billion dollar businesses now rather than five to $10 million in selling it now that largely has because of technology.

Nick Astwick:
Technology and partnership enables you to scale across the world. And so I think we’re just at the start of that. I mean, our country, you know, our GDP is still relatively low and we’re only going to get there by building industry and not selling it early, is actually scaling business and having those benefits brought back to New Zealand. Whether that’s employees, higher paid jobs, those sorts of things, that is critical. But technology landscape is the critical. Not just technology businesses, but leveraging technology to reach the world and make a good return. I want to be part of that journey.

Paul Spain:
Yeah, that’s great. If you were to leave listeners with some tips, whether they’re nichisms or, you know, things from, you know that you’ve learned and things that you live by, what would those things be?

Nick Astwick:
Be ambitious. Think big. I mean, I think that is quite critical. I mean, choose to lead. I would say be very intentional in that. Be a champion team. Not just a team of champions. I think that’s what critical.

Nick Astwick:
I mean, that’s what New Zealand. I mean we are as a country, we value relationships, we do things, you know, we’ve got a team orientation. So I would say, as I say, build a culture, go for it, think big. Yep. And don’t sell your short. Don’t sell yourself short.

Paul Spain:
Fantastic. Anything else you’d like to add, Nick?

Nick Astwick:
No, thanks, Paul, that was fantastic. Thanks for your time.

Paul Spain:
That’s great. Thank you.

Nick Astwick:
Thank you.

Paul Spain:
Cheers.

Nick Astwick:
Great.

Paul Spain:
Well, I trust you enjoyed hearing from Nick Astwick. The New Zealand Business Podcast is brought to you by One New Zealand and Gorilla Technology. Be sure to listen in to our other episodes featuring many of New Zealand’s most successful leaders, including founders such as Sir Peter Beck of Rocket Lab, Brooke Roberts of Sharesies, Sir Rod Drury of Xero Cecilia and James Robinson of My Foodbag, Sir Michael Hill and many more. And if you benefited from this episode, be sure to share it with a friend. The New Zealand Business podcast brought to you by Gorilla Technology, your strategic and proactive IT partner.

 

Read More »

Sam Kidd – Co-Founder and CEO of LawVu

Posted on 9 Feb 2026 in Featured

Sam Kidd – Co-Founder and CEO of LawVu

Host Paul Spain sits down with Sam Kidd, Co-founder and CEO of LawVu, for a look at what it takes to build a global legal tech company from New Zealand. Sam shares about assembling an exceptional team, maintaining culture across continents, navigating remote work, and the personal highs and lows that come with building something meaningful.

This episode delivers practical insights, honest reflections, and inspiration for anyone growing a company in a rapidly changing world.

Book your Cyber Risk Reduction Review session now (limited availability)
https://gorillatechnology.com/cyber-rrr

Special thanks to our show partners One NZ and Gorilla Technology.

Listen to the Podcast Here:

Apple Podcasts YouTubeMusic  RSS Feed

Paul Spain – LinkedIn
Paul Spain – CEO, Business & Tech Commentator, Futurist

You can keep current with our latest NZ Business Podcast updates via Twitter @NZ_Business, the NZ Business Podcast website.

Episode Transcript (computer-generated)

Read more

Paul Spain:
Well, great to have you on the New Zealand Business Podcast, Sam. How are you?

Sam Kidd:
Yeah, very good. Thanks very much for having me.

Paul Spain:
Look, you know, it’s been incredible sort of watching from a distance the LawVu story, but keen to delve in and hear a bit about your story and your background and to, you know, really delve into what you’ve achieved with LawVu over the last sort of decade or so. So maybe we can start at the beginning. You know, where were you born and where’d you grow up?

Sam Kidd:
Yeah, was born in New Zealand but not necessarily raised in New Zealand. So I was kind of here for the first sort of 10-ish years, and then pretty much from the time I was 10, 11, moved to Ireland. My dad was kind of coaching rugby back, kind of, yes, certainly before the professional era. So ended up what was supposed to be a 2-year stint turned into a lot longer for me. And then, yes, pretty much kind of grew up in Ireland. Never really imagined myself kind of living back in New Zealand. I think, you know, kind of once you kind of got into Europe and always kind of looked at New Zealand as home. And then it was 2013, kind of moved back here with a family.

Sam Kidd:
Just thought it seemed like a nice place to come for kind of a year. And I think my parents had just moved down here up Papamoa Way and were kind of sending photos of them strolling on the beach. And in winter it was warmer than the summer we were currently having in Ireland. So we’re like, okay, let’s just move back for a year and kind of experience that. And yeah, one year’s turned into 13. So it was kind of like, it was quite a strange thing. I always kind of got picked up as a Kiwi overseas, and then when you move back, obviously my accent had morphed a little bit more Irish. And so it was kind of like a foreigner coming home, uh, in some ways, because I wasn’t used to the New Zealand way of kind of living and stuff.

Sam Kidd:
So it was a really interesting experience. But yeah, I’ve really enjoyed being back here. And yeah, obviously it’s, you know, kind of led to the creation of LawVu as well.

Paul Spain:
Yeah, yeah, that would be quite an unusual return when you, you know, really spent so much time, you know, away if you left when you were, you were 10.

Sam Kidd:
So yeah, yeah, I had a small stint back here. I was in New Plymouth Boys High as a boarder for about a year and a half, kind of like the school C age, which I don’t even know what that is here now, like 15 or so. Yeah, yeah. Uh, yeah, and had a whole lot of different companies in Ireland. In the last company, in which when I moved back, I still currently in, was kind of in the online project management space. So when I moved back to New Zealand, it was really with the eye of kind of servicing our clients that were on the West Coast of the US. And so I could do that as kind of before, I suppose, remote working was really a thing, and it was easier for us to support them from there. And then kind of one thing led to another, end up kind of selling out of the company back to the founders.

Sam Kidd:
So I got to take a little bit of cash off the table, and that was when I was kind of looking around, you know, what would I kind of do next. And when I moved back to New Zealand, I was I suppose like you’d be— I’ve been so out of the, the community here and then other business community. And so we’re— I got involved in Startup Weekends, which kind of was quite a big thing in New Zealand around that kind of 2013, 2014 sort of stage. And so I ended up doing a lot of mentoring and, and just trying to network my way around. And, you know, legal came up a few times during that. And also during my process of kind of selling out of my company, I got to experience the utter joy of dealing with lawyers and what that process was like and just how foreign it was to me. So LawVu in some ways was kind of born a little bit out of kind of scratching my own personal itch, like how do I engage lawyers better, how do I have any sort of concept as to what’s required to be done. And during that process, I’d want to move back here because everything I was doing was remote.

Sam Kidd:
I’d set up a co-working space here. And so I got to kind of meet folks there since I wasn’t kind of working with anyone kind of locally. And one of the people that was in the coworking space with me recommended a friend who was at a law firm, kind of work on the business service side, a guy named Tim Boyne who had already kind of started doing something in that sort of space. And so we kind of met and it was a meeting of minds and some of the background that I had in the kind of online project management space and trying to create tasks and templates was very similar to the work that he was kind of working on. How do you template the structure of a legal matter and kind of one thing led to another and we ended up kind of catching up and then yeah, sort of LawVu was kind of born out of that in some ways. This was what, around 20— 2014, 2015 is kind of, yeah, 2014 is when we started kind of kicking around an idea. I suppose it’s the one thing when you’ve kind of come out of a successful company, that fear of starting again and failing, you know, like which I’d never sort of had before. Like I’ve been involved in, a ton of businesses from the time I left school.

Sam Kidd:
I’d been video production, had an internet gaming café, I’d serve hot dogs and donuts to drunk people. And sort of like, so I’ve kind of done the retail business and then end up in a software business. And kind of as SaaS was becoming a thing, so that was the last I was in a SaaS company. And, you know, we had millions and millions of users. And then you’re into starting again. And that was probably starting LawVu was probably the first time I was actually scared about starting another business because it’s like I had money in the bank, things was kind of going well, and I was like, well, what happens if I fuck this up, basically? Yeah. And we’re kind of like, we like, where do you go? And so, yeah, and you’re also older, have kids, have a mortgage, and all those sorts of things were kind of different. But it was— so I spent more time trying to kill LawVu in the early days as to, this shouldn’t work, like, why should this work, why should people care about this? And every kind of step we took along the path is like, well, this, like, this needs to exist, and we kind kept finding reasons to, to continue because it was— I suppose it was a strange concept.

Sam Kidd:
Like, we were creating a category and we were creating something that people weren’t necessarily asking for, but we could just see this gap in this kind of greenfield space, which when I first got into, I thought like a greenfield space would be awesome. But greenfields is actually so much work because you also then have to educate the market and kind of bring people on the journey. For those that don’t know what LawVu is, like, LawVu is a platform that sits inside corporate legal teams, and we really kind of help structure the day-to-day workflow. So for the way that the legal team inside these organizations deal with themselves, how they communicate with each other, how they store documents, how they store files, how they capture communication from the business, so how they interact with the wider business, and then also how they send instructions out to external law firms and then collaborate on their work, but also capture the invoices and things that come in. So we are kind of that cradle to grave around all the legal work and knowledge and information that kind of goes on inside a corporate legal team. It’s fascinating that we think about that. That was a greenfield space. Like, we’re going into companies that actually didn’t have anything at all, so they were basically just operating on the Microsoft suite of Outlook and Word but didn’t actually have a product like a sales team would have Salesforce.

Sam Kidd:
So yeah, yeah, it was fascinating for me that, that that was a space that no one had really kind of tackled. So In some ways it seemed like a really obvious sort of thing that needed to exist, but bringing people on their journey from nothing to something, yeah, yeah, it was— it’s certainly been a journey.

Paul Spain:
Yeah. So tell me about the co-founder relationship and how, how quickly did you kind of click and, and, you know, feel like that that was, was a, an opportunity that was worth really putting more time into exploring?

Sam Kidd:
Uh, Tim and I clicked really quickly. And I’m like, I think about this quite a lot, and because like I know people that have gone to business with folks that have known for a long, long time and it hasn’t worked, it’s been an absolute car crash. And like I could probably count on one hand the amount of disagreements or arguments that Tim and myself would have had in the early days, considering we didn’t know each other, we had no background or history and things. They had like, I suppose, the things that we wanted to achieve, the way that we kind of tackle problems was similar in some ways and complementary in others where we were kind of like, we’re both from the business side so we kind of, I suppose, end up filling each other’s gaps around kind of things and we were probably a little bit clearer in the early days as to who would look after product, who would look after the business side of things. So Tim was kind of doing the product but then we started wrapping other people around us, yeah, quite quickly. So kind of, uh, Sarah who kind of came in as our kind of Chief Technical Officer Patrick, who I’d known from a kind of past life in Ireland, who kind of came as our CFO. And, you know, then kind of ended up with Mark, who was doing all the digital kind of design work and that, who I’d kind of met through other work here, and Sean, who kind of met through LinkedIn. So we ended up kind of getting the small founding team quite quickly.

Sam Kidd:
Yeah, and, you know, like, Tim and I worked away and spent like a a huge amount of time literally in each other’s pockets because in the early days when you don’t have any cash, like I think about all the travel that we did and we’re sharing rooms, we’re at the back of the plane shoulder to shoulder the whole time. So yeah, like it was a very interesting process as to that first introduction, right from the introduction was just banging away, you know, worked together for so many years.

Paul Spain:
What did that initial period look like in terms of building out something initially, finding customers, capital? How did those things fit together? Were you getting early customers?

Sam Kidd:
I think that the short version is it was freaking painful. I think that’s it. When you look from the outside in, it always looks like fun, and it always looks like things happen really quickly. When you live it day to day, like the first 3 years, was super grinding. Uh, you don’t have customers, you’re trying to build product. We’re building product in a very regulated space. You’re dealing with the most sensitive data of most organizations, so you can kind of get to that MVP stage quite quickly when you’re building. And then we go to roll into a customer, and the— we roll into massive multi-billion dollar organizations that don’t really like the MVP approach.

Sam Kidd:
So what’s your security kind of infrastructure, what’s all your documentation, where’s your ISO certifications, all that sort of side of things. And then you kind of get into a pilot customer, and then it’s, we need this feature, we need this feature. So the first 3 years was a lot. It was quite lonely in the fact that you’re just building product and you’ve got a relatively small team, be it 1 or 2 people kind of doing that because you can’t afford more.

Paul Spain:
Yeah.

Sam Kidd:
And you know that you can’t sell, so you get to a certain stage where you would kind of— would get in front of people would get them on board, and then they would generate feedback around the massive gaps that we had in the product. Yeah. And so in some ways, that way we don’t want to burn our leads, and so you almost can’t sell. So you’re trying to talk to people while you’re trying to fix these huge gaps, and then you get to the next stage, and then you kind of roll back out and start talking to people and that. So yeah, like, it was, it was basically 3 years of really building the product with little to no traction other than some early pilot customers and some positive feedback. And also you’re out in the market trying to talk to people and you know that there’s a gap, you know you’re solving a problem, but you can’t address that problem just yet. So yeah, as you can imagine, when you’re trying to bring clients on and you’re trying to grow a product but you don’t have any sales, that obviously eats into your pocket. So yeah, I was 5 years without any sort of salary or wage at all.

Sam Kidd:
So I was kind of investing money into the company. And then we got some local angel investors that were sort of, were able to put some cash in. So we kind of raised in, in some ways in dribs and drabs. So you sort of like, you get $400,000 or $500,000 and then you got some sort of proof points and then you kind of raise another little bit. And then we, I think we were starting to kind of get somewhere. We started to have a bit of traction with some clients overseas and later enabled us to kind of do like a $3 million round with some kind of super angels and that. And that that started kind of get us on the map. So yes, yeah, it’s again, when you kind of live it day to day, it’s like you, you feel busy, you feel like you’re not achieving a lot, uh, and then people on the outside, looks like it’s going really quickly because they just see the flashpoints or the proof points or the things that you’re kind of loading into LinkedIn.

Sam Kidd:
Like I’d be in Australia and meeting all these epic people in the legal ops community, which was one client, but again, it’s how you promote yourself and all that sort of smoke and mirrors that kind of comes with that in the kind of the early days. But yeah, like you look back now with rose-tinted glasses as to the fun days. But yeah, like it’s, it’s so much work. you, Like, like, I think of anyone that’s starting off now, you take your hat off them because like it is, there’s so much to get done with so little resources in the early days.

Paul Spain:
Yeah, it’s through those harder times that often the biggest learnings and so on come. What would you say were those, those kind of key learnings from the earlier phases of LawVu. Obviously you have to have a real level of tenacity to kind of keep going for a period of years when, yeah, you haven’t kind of cracked it as such, right?

Sam Kidd:
Yeah, I’m trying, like, I’m trying to— you ride the line of being absolutely and utterly crazy and believing too much you’re on cool, but knowing, but being able to kind of spot the reasons as to this should exist. And that’s what kind of— in the early days, you’re trying really hard to be like, is this, is this really a thing? Are people— because also when you ask people for feedback, everyone, yeah, I love, like, really like this. Like, it’s really hard to get really honest feedback because it’s like when you go to a restaurant and everyone’s like, did you enjoy your meal? You’re like, I loved it. And you’re thinking, that’s terrible, I’m never coming back here again. Because most people want to be nice the whole time. And so you have to kind of be able to filter that feedback that you talk to people about. And so you’re trying to ask in certain ways about what are you trying to do here, what are you trying to achieve. And you can see by usage patterns or what they’re doing as to what’s— what are the actual real gaps.

Sam Kidd:
And so I think that’s probably the secret in the early days is you’ve got to really ask probably more the why, because I think if you, if you’re looking kind of for feedback as to do you like this or do you enjoy this, if you ask the wrong questions, you end up with a kind of a false positive and you can kind of continue forward and you’re not really addressing the right things. So I think that, that whole point of kind of being curious and questioning yourself the whole diamond question, why customers or potential customers are doing the thing they’re doing or not doing it, uh, becomes your kind of secret sauce.

Paul Spain:
And how easy was the sort of the early capital that you raised? How— I’m guessing easy is probably the wrong word to talk about raising capital usually.

Sam Kidd:
Weirdly, it’s easier. Well, let’s say, is it easier in the early days? I always think of that— I don’t know if you’ve ever watched that sitcom kind of Silicon Valley Yeah, and they talk about, they’re like, we need to get to revenue. And they say, no, no, we want to be pre-revenue. And the craziness is that is actually true, because once you’re into revenue, your stats and your statistics and all your data points and things like that are far more kind of under scrutiny. In the early days, it’s based on the idea what you believe you can do, and there’s, there isn’t much to dig in on other than do people believe that this is the team that can achieve that, that your hypothesis on what the market could do and what their TAM could be, like, that, that’s infectious. If if you, you kind of got the right way and people can kind of believe in that, once you’re there and you’re selling and then you can prove or you can’t prove how easy this is to sell, that’s when people kind of dig in. So kind of weirdly, as we, as we got further down the track, every raise is always like, well, it’s going to be easier after we did— like, we did a Series A during COVID but each subsequent raise is almost harder because you really have to then back into the data and the numbers, and you’ve got a lot more modelling. There’s a lot more kind of reason behind the, the why we should take this and what can that actually kind of be.

Sam Kidd:
So yeah, in some ways, or whether it’s just you’re kind of a little bit naïve and gung-ho in the early days, so you’re like, yeah, we got this. So yeah, the, the early raises almost easier, uh, in some ways, and, and smaller sums of cash, you know, when you’re kind of talking about raising $500,000 or a couple million, you know, it’s different to kind of— we’ve raised probably about $50 or $60 million to date now, uh, and kind of done those in tranches throughout the time. So yeah, every raise comes with its, its challenges, and then it’s economic conditions, what’s kind of happening, what the sort of macros in the space and things like that as well, that kind of change that dynamic.

Paul Spain:
How did sort of building out that, that early team look? You know, it seems you did, you know, pretty well with bringing together a great group early on. How did you achieve that?

Sam Kidd:
Yeah, that, like, the team is everything, and, and so being able to identify people that have the same passion and excitement around the space. And so, like, there’s a bit of serendipity there. You get lucky, certainly, with folks, but, but you also get used to kind of just talking to people and kind of seeing, can you bring people on that journey with you? And like, all our early team has pretty much been there right from the get-go. Same as you kind of scale as a company, the, the selling people on the dream and also kind of learning about what skills that they have. And so like, I always kind of believe like I’ve got talents in certain areas, but I also know that I need to, to bring other people on who I can also let loose because I don’t know as much about engineering, I don’t know as much around kind of the product design. And so you’re looking for people that you can bring into the company and enable them to do their best work. So I was kind of on that whole track of like spotting that talent, bringing them in, enabling them, and then there’s an ownership from them as well. I think when people own something, they feel like they’re contributing, then they give their full selves as well.

Sam Kidd:
And so it’s like, how do you get that right? I think that’s, that’s always the, the danger of a founder is that trying to get that balance right between how much you should lean in and how many grenades you can throw, and then how much do you trust the people that you brought in. If you’re just bringing in bodies to tell people what to do, you’re never going to get the best work out of people. So it’s that, it’s that real enablement kind of piece. And you know, like, I think that’s been one of the joys of building LawVu, is seeing people come in with just incredible talent and being able to see what they produce. And like, I’ll sit in, in some design meetings or some of the kind of product engineering, and you kind of listen to the that they’re solving, doing each day. And it’s like this weird kind of almost like an out-of-body experience. You’re like, I’m sitting there being— I don’t have a freaking clue what half these people are talking about. How did I convince these super intelligent people to join? And you just listen to the passion that they have for your baby and your product that you’ve kind of created, and they’ve helped elevate it and bring it to the next level.

Sam Kidd:
I think that that’s— for me, that’s that excitement in the building a company like this is enabling people to do their best work and take your idea to a whole other level that you couldn’t have imagined. And then for me, it’s like, how do you help steer where you need to steer and give guidance but allow people to kind of do their thing?

Paul Spain:
So what’s, what’s been your approach to get that, you know, get that to work and, and yeah, give, give people that opportunity to achieve their best work?

Sam Kidd:
Part of that’s the, the nature-nurture thing, is it’s just Well, it’s just my way of operating. Yeah, it’s kind of a little bit like how do you breathe? It’s something that I just don’t think about. It’s probably, if that’s been my superpower that I’ve kind of had in starting a company, it’s been able to kind of do that, find the right people, give enough guidance around what we’re trying to achieve, but then be able to kind of listen. I think that like I wasn’t as good with that in the early days. And so I think it’s like probably getting better as I get older. Is to learning when to lean in or when to be quiet as well. Because it’s, as a founder voice, your voice carries a lot of weight, good and bad. And so it’s like, when can you use that for good? But it can be super distracting if you kind of roll in and just say something, it’s like tossing a grenade into a meeting, and then suddenly everyone starts leaning across to, okay, maybe we should be doing this.

Sam Kidd:
And so Yeah, I’d love to say I have that spot on, but maybe if you interview the rest of the team, they’ll be like, ah, so painful when he comes into this uh, meeting, and as well. So yeah, it’s— yeah, trying— you’re trying to get that balance right, uh, the whole time. And you know, there’s probably sometimes I’ve done that really well, other times where not as much.

Paul Spain:
How important has the, the hiring, you know, been for you? And presuming that’s pretty closely connected.

Sam Kidd:
Yeah, the team’s everything. Yeah. Yeah. Like, your product is one thing. The people that you surround yourself with to build a company is, without a doubt, I think it’s how you win. It’s also how you lose as well. And so getting the right people in the right seats and— I think probably where we’ve been better is as we kind of get older and kind of mature into the kind of company is, you know, when do you make those tough calls around, okay, this person got us to this place, but we actually need to bring someone else in now, which is not a very Kiwi thing to do, like the way it’s kind of structured. And also, you know, to the restaurant comment, like everyone likes giving positive feedback, but like it’s hard giving feedback which, you know, isn’t always nice.

Sam Kidd:
And it’s like, and you’re trying to do it in a way that’s kind. And like we always sort of say, assume positive intent. Like you’re trying to bring people on a journey, trying to make sure that you’re offering feedback which they can do, which is constructive, which you can do something with. And that’s, that’s a skill that has taken us time to kind of learn. How do you kind of pass that down to other people inside the organization? And we’re still trying to get better with that. But yeah, bringing people in, but also working out how you can let people go. Like, business is ruthless in a sort of way. Like, you’ve got numbers and targets, you’ve got to build a product that people want, and you’ve got to surround yourself with the right people.

Sam Kidd:
And I know people often talk about a business from, you know, like it’s like a family, but it’s not. It’s not a family, it’s a team. And so, like, it’s been really interesting to see when we bring people in who’ve had sporting background, I’ve been in professional sports. And in sports, like, you’re at the right place at the right time, and then you change the division and you’re not the right person, it’s like you’re gone. Like, yeah, look at the— we’ve just cut our All Black coach. And like, you can’t say he’s not a successful coach. Like, the, the background and pedigree and the results he had in before in the last gig, hands down, you would have thought he would have been the right person for the job. But it just didn’t work in this environment.

Sam Kidd:
And they’ve made the tough call there, but doesn’t mean that he’s not a good coach. And I think that’s the same inside a company. You can have the right person in the wrong role, and then the kindest thing to do is actually have them leave, and they can go somewhere else and they’ll be so successful, ’cause that company will just suit their skills and the kind of what they’re doing. So that’s, I think, kind of the approach that we started to take with people is like, it is a team and it’s time and place and role, and sometimes you get that right, but if you don’t, you have to actually kind of address that.

Paul Spain:
What’s your approach to addressing that with people? How do you do that? Obviously there’s, you know, in New Zealand we’ve got, you know, particular kind of legal framework around, you know, how you exit people from, you know, from roles different in different places in the world. So you’ve gotta have your head around all of those things ’cause you’ve got, how many countries have you got people in?

Sam Kidd:
Yeah, I think it’s about 16 different countries. Yeah, yeah, uh, yeah, and obviously, yeah, there’s different rules and regs for each country. I think the approach that you want to take is, is like just an honest approach with people. So regardless of the laws, if you can have an honest conversation with someone, most people will take that on board. And then you can, you can like— we look at the way you onboard people, but how do you offboard people in in a positive way and you’re trying to do the right thing by people. So, you know, you’re not looking to just walk in like you can in the US and be like, everyone on that side of the building, you’ve got a week to go away, go and leave. So again, it’s your approach to it. And I think honest conversations with folks, which is hard to do.

Sam Kidd:
And I know people can listen to this and be like, well, they weren’t as honest conversations as I would have liked. And, you know, we get better at it and sometimes we do it well, sometimes we don’t. I just think the laws are there. You want to make sure that you’re following the kind of the right legal routes, but in the end it’s people. It’s people to people, and it’s a lot of it’s conversations, and you want to make sure that you’re setting people up for success. And if it’s not working, you need to have that conversation. Yeah. And then you of— you kind can, can go from there, but it can be quite a kind of a mutual process in some ways.

Paul Spain:
Yeah. And In terms of your experience with going through those, I guess each individual you can sit down and have an honest conversation, but you know, each, each person is going to be unique in their response, aren’t they? So I guess that can be pretty painful to kind of, you know, for the you person, know, on the receiving end of such a conversation and can be pretty challenging, I’m sure, for the person.

Sam Kidd:
Yeah, like, and, and, you know, like, it’s, it’s not often myself who’s giving that, you know, because we’ve got hiring managers and people that look after— like, it’s— be on the receiving end is tough. Being the person giving the news is hard. It’s so hard to do because, like, unless you’re an absolute psycho, you’ve got empathy, you understand what it would be like if you’re on the receiving end. And so that’s what I mean, you’re trying to do the right thing and have a conversation with like, in a— we’re assuming positive intending, you’re trying to do the right thing, but like the outcome’s not always nice for both. And like, I don’t know of anyone that enjoys letting people go at all. And like, I think you look at this during COVID you know, like always kind of look at all the rifts and things that companies had to do. But in New Zealand, it was hard work. Like, I think of like we’ve got a lot of folks from zero, and so you heard the stories where the decision was predetermined even though you can’t by law, but you have to go through this convoluted process because in the end a business needs to survive and you’ve got outgoings and you’ve got incoming.

Sam Kidd:
And if your income is not matching your outgoings, like you have to make tough calls, but the laws are set up there where you have to go through such a long process. Everyone knows what the outcome’s gonna be, but you drag it on and on and like it’s mentally taxing on both sides. And so it’s like, those laws are there to protect, but they also do hinderance a lot of work when, you know, in the end it’s like there isn’t an unlimited amount of cash inside an organization. You need to make those calls. I think that’s where the US can react really fast. And so like, that was to our benefit because obviously when COVID hit, US laid off a ton of staff incredibly quickly. That was a massive opportunity for us because suddenly remote working became a thing and we were able to pick up some epic people really quickly who wanted to work remote for a New Zealand company, and we were kind of away. So, but New Zealand companies were slow to react.

Sam Kidd:
He saw how slow New Zealand was to actually come out of COVID because, yes, companies were running out of cash. They were kind of put themselves in, into this kind of dangerous position. They couldn’t react quickly to it, uh, through the people side. So yeah, it’s a double-edged sword.

Paul Spain:
And what’s what’s your, your approach to, to hiring? How do how do you, you go about finding people? And what’s your— yeah, what’s your— what are your techniques there?

Sam Kidd:
I think it’s different for— like, for me, it was very conversational with folks. Like, the culture piece is huge. Obviously, once people kind of go through and you’re looking for people with the right talent, and like I say, like, everyone can act really well for a really short period of time, so you don’t— you don’t always know. I was always trying to look at how do I get out of this, like a very kind of heavy process interview and make it more human. For me, throwing a couple of fucks into an interview was fascinating because it could change people both ways really quickly and suddenly people became a little bit too much themselves.

Paul Spain:
Okay.

Sam Kidd:
And then you’re like, I’m not sure if this person’s actually going to be the right fit. Or just relax people, and then they could kind of talk freely. And you could see actually this person, the way they act, and it just took the stuffiness out of the interview. And then suddenly you got a much better read on what this person would actually be like, and you could, you know, have a, like, a more human conversation without feeling very stilted at times. Because it’s, yeah, it’s a nerve-wracking process to kind of be— if you, if you really want a job and you sort of like, you’re trying to give these perfect answers and you’re like, you know, this is not like, I don’t believe that this is the way you kind of actually kind of operate. And then other people would just get too loose, like, oh, this is kind of a chilled interview. They start talking like, okay, interesting. So yeah, yeah, it’s, uh, yeah, you’re just trying to break the formality of an interview, uh, was kind of my approach, uh, to it.

Paul Spain:
Yeah, yeah. And in terms of, you know, building that global work force, how, you know, how challenging was it for you to find the, the right, uh, you know, people, you know, particularly in those early days? But I guess as you’ve, as you’ve scaled, you know, you’ve, you’ve been able to bring in roles to, to really help and, you know, facilitate that, uh, yeah, that hiring and growth.

Sam Kidd:
I’m picking, yeah, the, the early days is certainly harder, uh, like, terrified around the culture piece. Like, what’s that going to be like to bring people in overseas? Are they going to feel like they belong with LawVu? Like, you know, is it going to suddenly be an us versus them kind of mentality? Which in some cases in the early days, it was a little bit like that when you’re bringing US stuff on because they were— US stuff always used to be top dog. And now suddenly all the decisions have been driven out of New Zealand, of which the US is our biggest market. So that with some of the people you get, they’ll be like, but we, we should be the ones kind of making some of the control decisions because we’re in the US and there’s this— we’re the biggest market and we used to be in bigger companies, we know. But so you kind of end up with that kind of power struggle. So that’s sort of when you realize that you haven’t got the right people there But that was also because you end up with a massive time lag as well, where you’re trying to bring people on board and you don’t have enough people in one country for it to feel like they’ve got enough people to surround themselves with and to ask questions. So for them, it’s like they’re working their day by themselves and then we come online and then they’re gone. And so that, that, that it’s always really hard and Probably obviously the hardest is when we started to stand up the UK team and we ended up asking one of our team here to move over.

Sam Kidd:
And so she moved over and is still there. So it will probably be her third year. I think she might do— I think she’s doing one more year in the UK. And that was in some ways to ship our culture over there, but for her to be that kind of voice and to kind of help rally the team and bring the team on when they’re small until it starts to kind of develop its own LawVu culture. And they’ve got enough teammates around them to be able to kind of answer questions and get shit done and actually kind of sort of operate. And then you end up with our offsite. So we do 2 offsites a year. We do a go-to-market at the start of the year, and we do our EPO, which is our engineering, product, and operations offsite.

Sam Kidd:
And so we bring everyone in to one space. So we brought our whole go-to-market team, which is global, into HQ. Last year. This year we’ll be in Hawaii, and so we’re flying everyone in. Um, all the engineering product offsite we did in Rotorua last year, we did in Auckland this year because most of that operations and engineering is in New Zealand. So when you’re like— we’re 160 people globally now trying to actually bring people together and unite them. And then we try to do that on a smaller scale where we bring our sales team in to have them kind of collaborate together because everyone’s kind of remote. And so yeah, it’s like I’m jealous when I kind of read books from other founders who have had everyone in the— I’m gonna say the olden days, you know, but you’re thinking like through the ’90s and early 2000s where everyone was in the one office or in separate offices, like that culture piece and just that water cooler moments that you— that we’re trying to create virtually now.

Sam Kidd:
Yes, because there’s so much information that you transfer through osmosis by hearing conversations that you, you have to now somehow look at how do you recreate those moments through a Teams call or through Slack or bringing people together and kind of having those kind of touch points. So yeah, I actually think that culture piece is, is so much harder to do now. Like even in New Zealand, we’re what, about 100 people through NZ? We’re still geographically spread. We’re about 40 here in HQ and then we’re split between Christchurch and Auckland and Wellington and some folks in Invercargill and that. So yeah, like even, even inside New Zealand you’re quite geographically spread now.

Paul Spain:
So, you know, walk us through how you went from— your initial team was working together here in Tauranga. What were the triggers to, to hire in different, you know, locations? Obviously, you know, at times it’s like, well, we need to sell into this market, we need people, um, and so on. But there’s always a, you know, I guess a mix of of drivers at times.

Sam Kidd:
Yeah, the, the fact that our markets are in other geographies was, was the driver. So our engineering and operations has always kind of been NZ-based. Uh, the fact that Patrick, who joined, was CFO, he was already based in Ireland. So right from the get-go, we kind of had someone who was overseas, and that was just because he was my contact and someone that I trusted with my life and with our bank balance and that as well. And so he was the right person to kind of bring in I think that the, the fact that a lot of us on the founding team, when I look, like, obviously myself, I spent a huge amount of time overseas in Ireland. Sarah, who came as CTO, was from the UK, who just moved back here. Yeah. Sean, who’s on our legal team, is from the UK, who’d been living in Hamilton, so he you know, he was, was remote for us.

Sam Kidd:
Some of our engineers were kind of Auckland-based, so we were kind of local, but we were actually quite remote right from the get-go. And then, yeah, as we look to bring people overseas, I was doing a huge amount of travel. It’s like, if you’re going to sell into the US market, you need people in the US market to talk the talk as well. And so, like, you do quite well selling remotely, and we were kind of doing that whole remote sale before it was a thing. COVID was obviously a horrible experience for the world, but I think for New Zealand like it flattened the world for us. And I think a lot of tech companies have actually kind of reaped the, the rewards from that because suddenly we had the muscle memory from being able to sell and operate remotely. And then it wasn’t weird for us to be joining a Zoom call or Teams call and selling. They, in some ways, they stopped asking the what’s it going to be like to buy software from a New Zealand company because that was a real block in the early days.

Sam Kidd:
And so that’s why we put people on the ground. We wanted people within a US accent, so they would stop asking the— I don’t know, like, it was a real thing back then that this is— you’re going to be supported from New Zealand? I don’t know, like, yeah. And then that just, that just vanished literally overnight. Uh, but that was our reason. We still wanted to have our support and sales and implementation and market, uh, just from a time zone perspective, because it just— like, I worked all the hours, uh, and the other days, like, you’re talking to the UK, you’re kind of obviously doing the night time, and then you’re starting to get into selling into East Coast, and so you’re up really early and doing that, and you can do that for a period of time, and then you realize you just, you have to have folks in region. That was the driver.

Paul Spain:
Yeah, yeah. And, you know, through this sort of journey, you know, how stretched have you been at different, you know, different times? You know, it seems, you know, reasonably common for, you know, the work hours to get pretty crazy in a new business, in the startup world. How’s that, you know, played out for you?

Sam Kidd:
It probably depends on who you ask. Like, I enjoy— like, I enjoy the busyness.

Paul Spain:
Yeah.

Sam Kidd:
Uh, like, I, I suppose it comes out if you enjoy what you do, it’s not— it doesn’t feel as much like work. Like, there’s, there is times where it is quite grindy. And like, I logged my flight time for the first time in the 10 years last year. I did like 320 hours, I think, of flying. I knew I spent about kind of 3 months of the year kind of out of the country and did that pre-COVID. And then obviously I think that was quite nice to not travel as much then and then have kind of kicked that back off. There’s times where, yeah, that feels hard when you’re away from family and that as well, but I suppose I enjoy the work that I do when I’m there. And like always, I suppose I always looked at it as this is a marathon.

Sam Kidd:
And so, and try, I try to get this with the team as well. I think this, when you’re kind of building a company, you want everyone to be go, go, go, go. But if you do that all the time, if everything is always at 110, it’s like everything’s crucial, everything’s on fire, people will flame out. Yeah, and, and so like anything, you’ve got to learn. And it’s fun when you’ve got sprints like that, like, and at times in the marathon you’re like, you’re feeling good, you’re like, okay, I’m gonna go harder. And you have the deadlines and you’re achieving things, you know, knocking things out of the park, and you’re hitting things and you’re getting the positive feedback, and that energizes you. And then you finish that sprint and everyone’s like, I’m exhausted, but, but you get recharged from the energy of of what you’ve achieved, and then the pace kind of slows and you’re kind of in the planning stage, and then everyone gets riled up and ready to go. And I suppose now that you’ve— we’ve got more people in the company, you’re kind of doing that in, in different phases with different groups.

Sam Kidd:
And so like Q4 obviously is a massive sales time, so we operate calendar year, uh, here. Like the sales team, legal was at absolute 110 through November, December, our product team will start to do the planning phase. They kind of slow down, and then so they’re starting to kind of recharge, and that obviously fits with the New Zealand summer. And then we start to ramp up, and then, you know, things for us will be full tilt during the summer period with the sales team in the US, and that are kind of coming down. So you start to kind of balance that through different regions, and, and then you just, you need to listen to yourself. And at times it’s like, I think people talk about burn themselves out. And it’s a— you got to be able to identify that yourselves. You need to make sure you surround yourself with the right team and people that can pick things up, pick you up.

Sam Kidd:
And it’s a little bit of like— it’s again, it’s kind of back to that, that sports. I play rugby a lot when growing up, and you feel that there’s times when you’re going onto the pitch, you’re like, I just don’t have the energy, but the rest of the team kind of lifts you for that. And then you get going, then you’re kind of into it, and vice versa where you’re lifting other people. And So yeah, I’d love to say I have the perfect formula for that, but yeah, it’s a little bit of trial and error. But I think the fact it comes down to I just freaking love what I do.

Paul Spain:
Yeah, yeah, well, it makes a big difference, doesn’t it? And you get a lot more energy when you’re loving what you do.

Sam Kidd:
When you’re winning. And so making sure that you’ve got those goals that you can achieve and hit. And so like you always think about what you want to achieve, and you— and those are the, I suppose, those dreams and those highlights that you can have, and they sit out there. If you just focus on those the whole time, I think it would become grinding, and you’d be like, well, I’m just so far away from achieving that. So then you peel back to what are the little things that I can achieve now that I take that off, and we’ve won that, or we’ve done that, or we’ve hit that milestone. I’ve hit that milestone. Yeah, I think like We’re not great at doing that as Kiwis, at celebrating those wins. We’re a little bit like, oh, stoic.

Sam Kidd:
Yeah, it’s all right, you know. Yeah, the US are better. I think other countries are better at celebrating those. And so I, I think though, but those celebrations, those moments are the things that also energize you. And you— and that times when you get to certain milestone, when you actually look back at what you’ve achieved, because you never feel like that when you’re building a company. I think that’s, that’s what I’ve started to realize is that you are never happy. You never reach that nirvana. And if you look at every successful company out there, if you look at Apple, if you look at Microsoft, or like, they’re never happy with where they’re at because if they don’t reach that next milestone, then the shares tank and the company’s terrible.

Sam Kidd:
But you always think, well, they should be happy. And, but the only way to do that is to look back and reflect on what you’ve actually achieved. And I think you actually can achieve so much in a year, and you’re like, oh, and then it’s like, okay, cool, now let’s go for the next thing and the next thing. And then you have those little wins the whole time, and as long as the team is winning, then everyone feels pumped up, uh, about kind of what they’re doing. And I think that the hard times is like during COVID where it got harder to hit things and budgets being pulled and you’re not hitting your numbers. Like, those are tough freaking times to pull the team through that. You can do that for a short period of time, but yeah, that’s tough.

Paul Spain:
And so how do you tend to celebrate wins with, with with your, your team? How do you make that work when it’s not, yeah, all in person, it’s not all remote? You’ve kind of got that, that mix of, of people. You have to take different approaches and different teams and different situations, I’m picking.

Sam Kidd:
Yeah, uh, obviously we do our all-hands. We’ve got our annual sort of kickoff all-hands, which will be next week, and then we’ll celebrate the year that was. And so kind of go through the milestones throughout the year. We’ll have kind of moments we get to the the quarter and you talk about the wins that you’ve done. Or if marketing have had a huge campaign, they’ll kind of post the things and talk about what they’ve done. And then people kind of celebrate. You celebrate as an organization for the big things, and then also there’s the smaller team kind of things where the marketing team will celebrate this, or the CX team will celebrate, or sales will do this, and they kind of bring people together. And like, a lot of my travel is not just catching up with clients, be catching up with the team and you’re doing the team dinners and the team drinks, and you’re kind of just talking about what’s worked, and you’re congratulating people for what they’ve achieved, and you’re talking about what the next thing is going to be.

Sam Kidd:
And so like a lot of those touch points become really important, um, a lot of fun, uh, and it’s, yeah, let’s say it’s something that we’re trying to get better at. Uh, and then we’re like, we do our company awards, uh, now. So for our engineering offsite, we had kind of the engineering awards and product awards. As weird, like, in the early days, I think it’s really kind of felt naff and embarrassing, which it shouldn’t. But yeah, I don’t know, it’s a weird thing to kind of let you celebrate. And now you see how much it means to people to win MVP for kind of engineering, or to win awards for support and all the work that they’ve kind of done, how much it means to them. Yeah, like when I— like, I actually find it really hard to watch those because it gets like— there’s no way, there’s not a hope I could present any of those awards, like emotionally, which is such a weird thing. Like, happy things like that tear me up.

Sam Kidd:
Yeah, I think because I see how much it means to people and how much it means to me and how much they care. Uh, and so yeah, like those sort of award things. So now I’ll go to market that we have coming up next month. Like there’s a whole bunch of sales awards and CX awards and like, and just celebrating the epic work that people have done throughout the year. Uh, but yeah, I’ll be in the background trying to— who’s cutting onions near me? I’m okay. Yeah, no, it’s cool. It’s really, it’s just, it’s one of those things that just fills me with immense pride to see how much it means to other folks on the team, uh, for what they’ve achieved and how hard they go to bat for, for LawVu day in, day out. Yeah.

Paul Spain:
What, what do you think are the, the hardest things that, yeah, you, you and the team have achieved over over this, this period? What would be the the big, big points when you look back you that, uh, know, you’ve really achieved something that, that, uh, you know, has been really key for the business?

Sam Kidd:
Oh, I think it’d be a really hard thing to call out because they sort of feel like moments in time that when you look back now it’s almost kind of hard to pinpoint what they were. And a lot of it is, it’s communication between teams and handover points and finishing kind of the process and the operations around how a lead comes into Salesforce, how an AE picks that up, what’s the process, what’s like that sales process and journey documents. Like back in the day when I did sales, like I’m jumping on the calls with folks, I’m chatting through things. I have zero PowerPoint and slide decks or anything now. Like if I was to jump on a sales call now and the sales team did look at me, I’d look like such an amateur chump doing what they do now. So the, the level that things are in every year, you’re just getting incrementally better. And I look at the process that we run now, how tight it is, and those are things that have been game-changing. And then the way the sales team brings in our implementation team, the way they come in and they talk about what that implementation looks like to a potential customer, and then those handover points between our implementation and our customer success, who before were one team, and then they’re kind of— we divided them, and now they’re kind of— more united so that the whole handover process is just smoother.

Sam Kidd:
The way our product and engineering team was separate and is now intertwined, and the way that the cadence and their operations and the kind of trios there between the designers and the product managers. And so like each one of those things, when you look back now, seems so obvious, but as you’re growing as a company, you’re trying to put those systems and processes in place. Those are the things that fundamentally have shifted us hugely, but they become really hard points to kind of pinpoint the why. And a lot of it It’s freaking communications. Like, it’s how we talk and collaborate with each other, which when you think about it, it’s absolutely mental. Uh, the why— like, why is that communicate— that intercommunication between people is, is actually such a hard, difficult thing to get right? Because people also have to feel comfortable about letting go of things, especially scale. So when you’re 20 people you own a lot, and then you bring in other people, it’s like, okay, I don’t need to do this now, I trust you explicitly, so I hand it off. And people like, I don’t want to hand this off, I’m going to hold on to it, and that slows you down.

Paul Spain:
Yes.

Sam Kidd:
Uh, and so like, those are some of the things that’s quite hard to explain to people and, you know, to ourselves as to what that’s going to look like and all those stages that you’re going to have to kind of go through as you go from 20 to 50 people, from 50 to 100, uh, we’re— and what is it— at 160 people now. I know a lot of things that we have in place are going to break when we hit 200 because you’re just going to end up with needing another layer. And so how are you going to communicate between those layers? You kind of bring in the management. And some of that was, for me, was as we grew, was letting go of the hiring. Like, I do almost no hiring now. And so you’re trusting people with your process and to hire the right people, what that’s going to look like. And so, like, for for me, I was like for ages holding on to that. But you have to trust the people that you bring in to, to be able to then bring in the right people.

Sam Kidd:
And so, and that happens in every area of the business as you scale up.

Paul Spain:
Yeah, we talked about sort of capital a little bit, but how did this, this last sort of capital raise, you know, look? What did that look like for you? What the, what are were the sort of things that you had to put on the table? What are the sorts of things that you get, you know, create pressure or challenge in the process. Because obviously that went, you know, pretty well. You know, you come through with what, a $400 million valuation? Share a little bit.

Sam Kidd:
Super easy. Yeah, yeah. What you read in papers and the process that goes through, that’s a journey. Like, the valuation piece to me again is you want to be very careful around what that looks like and not fall into the trap of vanity metrics as well. And so if I think about kind of our capital raise journey when we kind of were raising funds in the early days, I think the first Series A raise we did was about $12 million US. At a $50 million valuation, I US. think, It was sort of what we did during that process. We were looking at other companies that were in a similar space, in the contract management space, that were raising $100 million at a $3 billion valuation with frickle revenue.

Sam Kidd:
And, and there it is. I’m like, how and why? And I’m so jealous of all the money they have But that valuation that you have there is now like a noose around their necks. It’s like, how do you grow into that? And so while it’s nice to have the large numbers, you have to pare it back to, am I actually going to be able to get there? Because it’s really easy to give those valuations away in the early days. The devil’s in the detail around what that actually kind of looks like if you start to move towards an exit. Because I tell you, the way the contracts and stuff are written the VCs aren’t the ones that are risking anything. So as a founder, you need to be very mindful about what you feel is actually achievable, what you’re going to get to, and being willing to make sure that you feel comfortable with the targets and the goals that you’ve kind of set for yourself in that kind of valuation. And so same for this, this last round is looking at what our metrics are, what I suppose kind of a dilution and kind of willing to take what that is going to mean for all the shareholders that we have on board, what that amount of capital is going to enable us to kind of do, and are we capitalizing ourselves enough to get to that kind of next milestone. Because that’s hard if you don’t bring enough capital on and you can’t hit the milestones that you’ve set for yourselves on the valuation, then that next round’s going to be quite painful.

Sam Kidd:
And we certainly had times during Covid, you kind of rate trying to raise capital when the markets are shifting, the valuation expectations had gone from insane kind of valuations to a more realistic kind of paring that back, but that put a lot of pressure on companies. So during this last round, like you’re always talking to people, you’re always kind of out there seeing what’s kind of going on in the market, and then obviously having good internal investors as well. And just trying to have honest and open conversations with them as to what we’re trying to do, what that’s gonna look like, what metrics we have around acquiring kind of new customers, and really trying to kind of lay that story out. ‘Cause as I said at the start, know, you the pre-revenue is much easier. When you’re in revenue and you’ve got sales stats and you’ve got retention stats and you’ve got churn stats, and like how much does it cost to acquire a like, you know, customer, like people dig in a lot. On those. And so those numbers and that story needs to kind of stack up. So there’s a huge amount of work, especially that the finance team that we have here had to do in all the modeling to kind of make that, that happen.

Sam Kidd:
So as I said, you’d like to think that those rounds get easy and easier. What gets easier is I’ve got better and better people wrapped around me.

Paul Spain:
Yeah, yeah.

Sam Kidd:
The work that goes into getting there, like, it’s a lot, it’s a lot of work and a lot of people that you need to kind of bring on on the journey as well. Yeah.

Paul Spain:
What can you share around your growth sort of revenue-wise and so on?

Sam Kidd:
Like our growth-wise, we’re kind of, yeah, we’re sort of north of 40%, so kind of up there. The logo retention, the NRR, like we’re, that net retention revenue need to be, I think we’re at 103, 104-ish kind of now. And then it’s, yeah, like we just, we spend a lot of time looking at kind of that logo retention that’s up into the kind of up above the, into the 90s. So those sorts of metrics need to be top class to allow you to kind of, uh, pull the revenue in or pull the, the funding in. So yeah, we’re obviously got our eyes set for kind of pushing towards that, that 50 million kiwi, which we’re kind of on, on track for now as well. It’s just the next thing is how fast you can kind of get there and how you can do that in a way that’s as cost efficient and effective as possible. And that’s the game, really.

Paul Spain:
Yeah, yeah. Now, one of the things that any business can, can go through is the different phases of people being in the business, people leaving the business. In your case, you’re here leading the business, but, um, you know, Tim, as your co-founder, has exited along the way. What was that sort of experience like? How, you know, how did you guys sort of work through, through that? Was that a sort of a shock to you when, when you found that he wanted to move in another direction? Was that something you talked about for a period?

Sam Kidd:
Yeah, I, I think it’s always a shock but not a shock, as in like we sort of knew and we started talking and it was just a time where I think the, the age and stage of the company and the things that he really enjoyed weren’t there as much. And, you know, we talk about raising capital. When you raise capital, it’s a different business. It’s— you’re founders of a company, but it’s your company but not your company. Like, I’m under zero illusions that I could be axed in the morning, uh, and like, that’s the game you play. Uh, I’m the highest individual shareholder. I’m not the largest shareholder, uh, as well. And, you know, people that invest Millions and millions in you, they want their money back and then some.

Sam Kidd:
And so that, you know, changes the game, uh, and the, the sort of stuff that, that Tim really, really enjoys, that scrappy stage at the start, they’re kind of about to kind of move really quickly. And then you, you just turned into a different animal. We just, you know, we’re having conversations around, you know, talking about before, you kind of enjoying what you’re doing, and we’re doing a lot of travel and given the stage that his family was at, he wanted to do this travel. And he was also getting really excited about a few other opportunities that were kind of appearing. And so, yeah, you have that conversation, you know, it’s, as I said, like we had kind of one hand the amount of arguments he sort of had, and, you know, just turned into a good robust convo. A bit of tears were shed from both sides. And yeah, like, I spent, I spent, uh, as I said, spent more time with him in those kind of early years than I probably did with my family. So you’ve got incredibly close, uh, and we’re yeah, still, still in contact all the time and that as well.

Sam Kidd:
So yeah, it’s tough, uh, and I think that the same with anyone that’s kind of been in a company for a long time, you know, whether it’s kind of in the founding team or not, is, you know, there’s ages and stage. And we had people that really enjoyed the holding all the Legos and doing everything, and then as the company grows and the team changes, they actually, they want to go back to, to that size of a company, uh, and Like, we always talk about that, like, I really want to see people that were really successful here go on and kind of and do the same thing somewhere else and kind of bring that knowledge experience on. Not right now for everyone because, you know, quite a strong team. But it’s the same as, as like when we were starting, like, we were going around trying to poach as many Xero folks as we could because we were trying to fast-track the learning that we needed because they were the company that had been there and scaled. And so like I wanted that experience. And so you’re reaching out to people that were, again, had gone from the smallest stage and zero all the way up to the kind of scale that they were at. It’s like, well, if they were to come to us, like, they would just fast-track us and would, you know, would move a lot faster. And it was true.

Sam Kidd:
And so you bring those people in, and that’s exactly what— like, I know we’ve got people reaching out to some Love U staff, and some of the team who have done that here have already started in kind of other places. It’s awesome to kind of watch their journey and and see what they do as well. So that’s, you know, I’d love to see that, that LawVu alumni actually kind of out there doing things. But again, this is not a— don’t, don’t start poaching my folks yet. We’ve still got a lot to do and a lot of things to kind of hit this year. So yeah, back off, people. Yeah.

Paul Spain:
And, and looking at, at New Zealand as a place to, you know, to build LawVu and and, you know, even, even down to Tauranga, Bay of Plenty region, you know, what do you think are the, you know, the strengths and maybe some of the weaknesses, you know, too, that, that, you know, we, we have, or the pros and cons of, of, um, you know, starting and running firm from, from here as opposed to being, you know, headquartered in Silicon Valley or, you know, UK or another market?

Sam Kidd:
I think that the hardest thing here is the talent. I do think that is changing. Like, if you look at that kind of cohort of companies that are on the rise now, there’s the Auras, there’s the Rocket Labs, there’s the Halters, there’s, you know, like, like I was looking at, uh, Icehouse’s kind of, uh, list they put up of all the startups. Like, there’s some epic companies that have now started to come out of New Zealand. So before, when we were trying to just hire zero staff there wasn’t really zero. And Trade Me was like the two options of people that have done anything at scale. I, I think in the next 5 to 10 years, that amount of talent that’s going to be floating around that will be interchangeable between different companies at different scales, it will be game-changing. So we will— I think as a country, we’ve had to go on that journey, uh, and kind of build that talent in and look at how we pull people in, uh, as well.

Sam Kidd:
So New Zealand’s a very attractive place to be in, to live. And so being able to kind of pull that, that talent globally in here, I think the more that we can do. And so that, that’s probably one of the disadvantages of being here. The other disadvantage is you— people can get sucked into thinking New Zealand’s a great test market. And I think it’s, it’s— yes, it’s handy as a place to get started, but it can also probably send you down the wrong path. And so I think when people start here, you have to think globally right from the get-go. And like, like, I could have counted probably on one hand in the early days the amount of clients that we had here and the people that we thought we were building product for. And then as you head into the US or head into Australia, what the requirements that they needed were different.

Sam Kidd:
And for us selling enterprise tech, like, New Zealand companies move incredibly slowly. I always thought there was going to be— I don’t know why I thought New Zealand companies or large corporates were going to have this kind of, we want to get shit done attitude. For me, New Zealand enterprise is dead. It’s just, it’s so slow moving because I just don’t feel like there’s this hunger and this pressure like that, that you get when you go to the US or Australia. There’s so much competition that when you’re inside those large organizations, there’s a real desire to get stuff done. We have to move fast because company ABC is breathing down our neck. Here there are two of them. There’s going to be two big companies in that space.

Sam Kidd:
You just can’t survive with such a small market, and so they just don’t move that quickly. So if you’re trying to build enterprise technology, you’re just not going to get any real urgency to get stuff done here. And so I think that’s probably a— the downside of being New Zealand is it’s not a it’s not a great— great test market in the enterprise software space. Uh, then yeah, then just the time zone issues, uh, is always a hard one, but As I said, like, you know, COVID has flattened the earth, and so that, that whole thing of not being able to kind of sell and be here and be based here, I think that that certainly evaporated. And so there’s some epic people that you can build really good global teams from here, and then how you connect to folks in other regions is, is a lot easier.

Paul Spain:
Yeah, gotcha. I’m thinking just sort of some wrapping up stuff so we don’t take up too much more of your time, can you maybe sort of talk to advice that you would share with others? You know, so maybe some sort of standouts from your journey around how you like to operate, or, you know, ways that you encourage others with your mentoring or talking to others. Are there some specific, you know, tips and things that you like to encourage people to take on board?

Sam Kidd:
Oh yeah, that’s an interesting question. So yeah, It’s the— like for me, it’s the surrounding yourself with epic people. Like building a company is so fricking hard. And if you’re going to spend a ridiculous amount of time with these individuals, make sure that you surround yourself with the right people. Because you’re going to spend a huge amount of time day in, day out fighting the fight. And you know, if you don’t feel like you’ve got the right people around you or you’re going to clash right from the get-go, it’s only going to go one way. The other thing that people are always going to say is, oh, make sure it’s something that you’re deeply passionate about. Which I don’t know if I was deeply— like, I can’t say I was deeply passionate about legal, but I am now.

Sam Kidd:
as Like, in, it’s a space that when you get into it, you have to be passionate about the customer and the outcome and what you’re trying to do. But when everyone sort of says make sure you follow your own passions, it becomes your passion as you get into it. So like, I think there’s a different approach to it because otherwise like you’d all be kind of trying to do something kind of vanilla or looking at something that you’re super passionate about. But there’s some really cool stuff hidden in plain sight. It’s like when you dig into an industry, uh, I did see someone the other day online talking about that you know, to really build something in the legal space, you’ve had to have come from a legal background to really understand it. Like, obviously I call bullshit on that because I had zero legal background at all, but, but what I was incredibly curious about the space. So it actually, in some ways, I feel like it freed my mind because I had zero preconceptions around the way people operated. So I got to ask all the stupid questions and the why and the why and the why and the dig in.

Sam Kidd:
And then you, like, if you’re that sort of way inclined, you can start to see the gold that’s hidden right in front of people’s faces. But if you’ve grown up in a space, you’ve grown up in an industry, you sometimes accept it for the way it is. And I remember in the early days, Tim and myself going and talking to some folks in legal team— in legal teams— because we were looking at like LawVu in the early days was like the unbundling legal matters, and we’re trying to like break it down. And what stuff would the lawyers do and what stuff could you do as an individual? And he was like, oh, you can’t do that, you don’t understand how complex these legal matters are, and it’s like it’s all in the deal. But like, when you actually dug in, you didn’t— they’re doing the same freaking things. The detail changes, but the actual step-by-step process was identical for every single type of the same type of work. But they couldn’t see it because they cared so much about the detail that they didn’t realize that everything they did along the way was so formulaic. But because I didn’t care about the deal, I cared about the process, we were able to kind of see that.

Sam Kidd:
So, so that also can be a superpower, that you, as long as you’ve got a deep passion, you’re curious about something, it really can kind of open your eyes up to a whole, like, an industry that you actually have no experience in. And, and so I think that’s always something that I say to people is like, you don’t have to have had a huge background in a region to be able to kind of create a dent. And I feel like the space that we’re in and a lot of the folks that we have coming in, they’ve got such a curiosity and they’ve got such a desire to help our customers achieve these amazing outcomes and make their work life better that they get super passionate about this. And suddenly we’ve all become kind of legal ops experts and we care so deeply about this sort of space. But not all of us came from it.

Paul Spain:
Gotcha. Yeah, it’s interesting. What would you say has been your darkest day on this journey? The sort of hardest thing that you’ve had to deal with?

Sam Kidd:
I’ve been pretty fortunate that there hasn’t been that many dark days in LawVu that, you know, we’ve had goals and targets and we’ve kind of been able to kind of move towards them and that everything’s been going in the right direction. Probably the hardest ones was, yeah, we obviously during COVID had to lay off a number of folks early on the kind of across the board, not a huge amount, But again, every person that you’re kind of talking to and actually having to kind of make those decisions where you look at the numbers, you look at kind of what we’re doing, what happens if we don’t hit our targets, what’s this going to do. And so kind of pre-empting that and having to kind of make those calls and then having to relay that back to the rest of the team to be like, this is a call we made, we’re letting go you of, know, some of your colleagues and your friends and things there, but this is the right thing to do. ‘Yeah, trust us,’ uh, and the company can survive and continue on. And so, yeah, and you’ve got to think about what that was like for those people to kind of receive that message. And it’s, yeah, you’re sacrificing a few so the company can kind of continue and grow. So that was probably in some ways the hardest time because we, we sort of did a whole whack of people in one go, but we felt like we can either take a small step-by-step approach and let a few people go and then see how we go, and what happens if we don’t hit it? We’re going to go again and then it could get worse. So we just took the, the approach of let’s go bigger sooner so we can do this once and then kind of re-message that.

Sam Kidd:
So I think that was probably one of the, the tougher things to, to kind of do. And then yeah, other than that, being pretty fortunate. Either that or I’ve just buried it in my mind. I can’t remember that. Someone will watch this and be like, but what about this? Person’s like, yeah, I forgot about it. It’s my coping mechanism. You kind of just, you move on, you focus on the positive stuff. You have to be, uh, that’s what keeps you going.

Paul Spain:
Yeah, well, there’s always another challenge to deal with. You can’t spend too much time looking back.

Sam Kidd:
100%. There’s always, there’s always things, and there’s always those decisions every single day that you make, and some sit with you longer and others— like, I, I spoke about this in another podcast, that in some ways I’m as deep as a puddle, and I think that also becomes my kind of secret sauce. There’s only so many times you can look back at the decisions you’ve made and question that, question that. And if you, you could end up in this paralysis where you actually just need to make a call, live with it, move on, uh, and then you feel that it’s the right decision. And don’t— you can’t spend too much time analysing it because you end up just kind of paralyzed. And you just got to feel like you’re making the right call day after day, and hopefully that’s lead you in the right direction.

Paul Spain:
Yeah, yeah. Um, anything else you’d like to add?

Sam Kidd:
Oh, nothing else I can think of that would be, uh, like, I’m obviously always keen, and I do have people, uh, reach out every now and then through LinkedIn just saying, look, I’d love to pick your brains and, uh, and talk through or ask questions around kind of decisions. And I suppose I can get kind of more in detail with individuals on that. Like, I’m always surprised at how little people kind of reach out, uh, as well. And the folks that have, I’ve been, you know, it’s, it’s gonna say it’s weirdly quite, uh, therapeutic for yourself, uh, as well when you’re kind of sharing the things, the indecisions they’ve been. And it’s, it’s really cool to kind of connect with other folks that are in the New Zealand startup space because, you know, it can be quite a lonely thing when you’re kind of getting up and running and and you know, you’ve got a lot of decisions to make. When you are sitting there and you’re looking at your LinkedIn feed, it looks like everyone is smashing it and you’re like, why the fuck is this not working for me? And why is this so hard? Because you don’t share the shit stuff. Like, I’m not posting I had to do this decision. I’m sharing the fact that I’m traveling to this conference, I’m doing this thing, and everything on my LinkedIn feed looks golden and everything’s up and to the right.

Sam Kidd:
And that’s the social media world that we live in. So, you know, at times people kind of want to get real or, uh, or ask certain questions or how I kind of went through a process, I’m certainly— connect with me on LinkedIn. Yeah, like it’s been quite cool to jump on with a few folks and do a Zoom call and you talk for an hour and a bit, and I’ve had kind of regular catch-ups with some folks. And yeah, there’s something nice both sharing and kind of helping people along. And I’d love to see the New Zealand tech ecosystem continue to grow and thrive because like I do believe as a small country at the bottom of the world. Like, yes, we’ve relied a lot on agriculture and other stuff, but like, we’ve got some— like, we’re really well positioned. We’ve got some epic talent here, and we can do some really, really cool stuff from this part of the world and grow massive companies from here. So like, anything that I can do to contribute to that in some small way and, and that, like, I’d be keen to, to get involved.

Paul Spain:
That’s awesome. That’s really cool. And yeah, I mean, I think, you know, the community aspect and that, the opportunities to, to feed in and support others that are coming through can, can make a really big difference, right?

Sam Kidd:
Yeah, it’s huge. And I think that’s, that’s always the thing in the early days, that the things that kind of accelerate it for us were the conversations that I got to have with people and the people that connected with. And again, it’s talking about when you print pulling people into the company that have been there and done that, it accelerates you as a company. And you, you just learn things, you take elements what they’ve done and you kind of remould it for what works for you. And like everything, it’s very hard to invent stuff. You’re basically big borrowing and stealing the whole time as you’re kind of forming a company. And, you know, and then you kind of mould it into what works for you. And yeah, that enables you to kind of take off and go a little bit faster.

Paul Spain:
Yeah, yeah. Well, that’s great. Oh, thank you very much, Sam. Really appreciate it.

Sam Kidd:
Yeah, thanks very much for calling in.

Paul Spain:
Yeah, cheers.

Read More »

Mark Powell: Leadership, Logistics, and Life

Posted on 30 Sep 2024 in Featured

Mark Powell:  Leadership, Logistics, and Life

Host Paul Spain sits down with seasoned business leader Mark Powell to delve into an inspiring journey of leadership, resilience, and transformation. Mark shares invaluable lessons from the frontline to the CEO’s desk. Discover how he navigated the complexities of unionized environments, spearheaded significant operational turnarounds, and adapted strategies to fit diverse market contexts. Mark’s reflections on servant leadership, work-life balance, and the importance of continuous learning provide a treasure trove of wisdom not just for aspiring leaders but for anyone striving to make an impact.

Listen to the Podcast Here:

Apple Podcasts  Googlepodcasts    RSS Feed

Gorilla Technology
Paul Spain – LinkedIn
Paul Spain – CEO, Business & Tech Commentator, Futurist

You can keep current with our latest NZ Business Podcast updates via Twitter @NZ_Business, the NZ Business Podcast website.

Read More »

Andrew Young: CEO, NZ Cancer Society Auckland Northland division

Posted on 26 Aug 2024 in Featured

Andrew Young: CEO, NZ Cancer Society Auckland Northland division

Andrew Young, Chief Executive of the Cancer Society’s Auckland Northland division join’s Paul Spain to discuss his learnings over 20 years of leadership and governance in the business and charity sector. Andrew shares his journey, driven by personal loss and a commitment to reducing cancer’s impact. Listen and learn from a key New Zealand leader, plus support Daffodil Day and the fight against cancer.

Donate at Daffodil Day 2024

Listen to the Podcast Here:

Apple Podcasts  Googlepodcasts    RSS Feed

Gorilla Technology
Paul Spain – LinkedIn
Paul Spain – CEO, Business & Tech Commentator, Futurist

You can keep current with our latest NZ Business Podcast updates via Twitter @NZ_Business, the NZ Business Podcast website.

Read More »

Jamie Hunt – Founder & Executive Director of Pressio

Posted on 5 Jan 2024 in Featured

Jamie Hunt – Founder & Executive Director of Pressio

Jamie Hunt, founder of Pressio, co founder of 2XU and professional triathlete, shares his journey from athlete to entrepreneur. Discover how Jamie’s unwavering passion for retail, ethical business practices, and innovative product development have propelled his ventures to international success.

Listen to the Podcast Here:

Apple Podcasts  Googlepodcasts    RSS Feed

Show Links:

Gorilla Technology
Paul Spain – LinkedIn
Paul Spain – CEO, Business & Tech Commentator, Futurist

You can keep current with our latest NZ Business Podcast updates via Twitter @NZ_Business, the NZ Business Podcast website.

Read More »
Malcare WordPress Security