“I challenge the whole concept of a CEO. It feels intuitively wrong to me…”

It’s safe to say that firing yourself is a rather unique experience in business. But this is an entrepreneur that has made a career of challenging the norm and thinking differently. Whether it’s taking on the male-dominated insurance industry or questioning the culture of high company valuations (AKA “Ponzi schemes”), she’s not afraid to blaze her own trail.

With refreshing honesty and unwithering self-reflection, in this conversation with Sam White, Founder of Freedom Services Group & Stella Insurance, we cover being “unemployable”, leading teams across the globe, raising funding as a woman, and much more.

Watch our exclusive interview with Sam White below.

Could you give us an overview of your career to this point?

I’d had a job out of university but didn’t really like somebody else telling me what to do. I think I just wanted a bit of freedom. I had this idea that if I started this business, from my sister’s conservatory, I’d be able to choose my own hours, and I’d be able to do a few hours in the day. I was making appointments for other businesses to start with, and then it kind of evolved into this claims management business.

I spent around 10 years building a business that was working with insurance companies, and it built that up to a significant size and scale. We were turning over around £18m and it was very profitable. I got very big for my boots and moved to Beverly Hills. I had a lot of fun over there, like having Robbie Williams sing at my wedding. Then the business hit some challenges in 2010, so I had to scale back a little bit and change direction.

I ended up working much more closely with insurance companies, and then ultimately setting up my own insurance business. Now I have three businesses in the UK, all around the motor insurance space. I launched Stella in Australia two years ago, which is a brand that is focused on designing financial services products around women. I’ve had lots of fun, got involved in lots of different things and been able to really feed into my desire for joy and adventure. I always say business shouldn’t just be about business. If it is, you’re doing something wrong.

You describe yourself as “unemployable”, is that something you notice in your peers too?

I say it jokingly, and actually, I’m hoping with the change in psychology around businesses that people like me do become more employable. What I mean is, when I took my first job, it was very much in a command-and-control type business environment, where somebody at the top has an idea about the way that things should be done. They tell the staff, it has to be done this way, with this process, and there’s no deviations. Now for somebody like me, that’s hellish.

I like to find my own path and feel my way through things. One of the things that I’ve strived really hard for in my own leadership journey is to get past this idea that just because people work for you doesn’t mean that you are the giver of all knowledge and instruction. You should be creating environments in which people can test and learn, and grow themselves, so they can feel that joy of creating something and building something, as well.

You’ve fired yourself as CEO – could you tell us about that story?

On a personal basis, I’ve always been a big fan of therapy. In a working environment, I’ve always been interested in coaching, and I started working with a coach a few years ago, just to shine the light in the dark corners that I can’t see. What am I missing in terms of my leadership style? This coaching worked so well that I wanted to get the coach involved with the team. They started working on a one-to-one basis, and I saw some real improvements from a team viewpoint.

But then I started to challenge this whole concept of a CEO. It feels intuitively wrong to me. The minute you put that structure in where there’s one person above that team, what you do is diminish accountability and empowerment because then there’s a natural tendency to defer to this ultimate leader. When I looked back on some of the challenges that we’d had as a business, it was because I wasn’t actually relinquishing that responsibility to the team.

I speak to a lot of business owners who say the same thing, like “why do I have to come in and fix the problems?” You’re always creating that dynamic yourself. You’re creating that rescue kind of scenario where you lead them for a period, something goes wrong, and then you’re having to dive in and save it, which is really kind of dysfunctional.

I started to toy with the idea of removing myself and replacing the role with a coach role for the team. I really do believe that businesses would function better with a management team that was being coached by an appropriate coach. So, I fired myself and replaced myself with the psychologist that was coaching me and the team. The theory absolutely does stand, as they’ve had a great year and done really well. We’re still experimenting with different elements to the structure, but I am cautiously optimistic about it as a general business philosophy.

Did you find that leading teams in the US and Australia was different to ones in the UK, and if so, how did you adapt your leadership style?

I think there’s always cultural differences. I definitely had some barriers when I set up in California. For instance, Californians have a very different sense of humour to a northern one. There was a couple of times where I mortally offended the locals with what I thought was just a bit of dark English humour, and they thought it was a sign of a serious psychological issue.

You do hit those kinds of cultural boundaries, but there’s also different rules of the game. So, if you’re raising money in the States, they raise money in a different way to the UK. When I first went over to the States, I was very naive, and just a bit overly enthusiastic and not as well planned as I could have been. Whereas when I set up in Australia, I think I went into it a little bit older, a little bit wiser. Culturally, I find myself much more aligned with the Aussies, and I really enjoy doing business there.

I think finding a place that feels the most aligned to you is really important. So, if I was incredibly process-driven, and left-brain focused, I might love doing business in Germany. However, I think I probably would struggle doing business in Germany because it doesn’t really fit with my personality. So, as an entrepreneur, it is also important to align that stuff. If it doesn’t feel right for you, and there isn’t that fundamental connection for you, then you probably shouldn’t be doing it.

What has your funding journey been like?

I had a pretty torrid time trying to raise money from the start. Statistically, it is much harder to raise money as a woman than as a man. I really struggled with it probably because when I was approaching banks, they were not seeing what they were expecting to see. Now, it’s ironic, because I grew all of my businesses from scratch, and most of them ended up profitable with multimillion-pound turnovers. But I couldn’t get any funding. I actually got my dad to pretend he was part of the business at one point, just so I could get an overdraft.

As the business developed over time, I learned how to leverage what we had. So, I would go to larger partners and do projects with them, where they would put up the funding and I would get the deliverables for them. That’s how we managed to kind of move forward.

Stella was the first time that I really got proper investment in my whole career. The first VC I met with in Australia was like, “I love it. I love what you’re doing and I’m going get behind you.” It’s been absolutely fantastic. They’ve been very supportive, and they get where we’re going with it. I’m now on a fundraise, again, because we’ve got global expansion plans for Stella, and I’m hoping that my experience of the whole thing is different to what it’s been in the past.

Do we need to change the relationship with and view of failure?

I love a good failure. When we go back to neuroplasticity, you cannot make change without suffering failure. I think most people are overly concerned about what other people think, and actually, other people don’t care. My general experience of people is that they’re far too obsessed with their own stuff to really give a damn whether you made a success out of that thing or not.

I saw something this morning that said, “don’t accept criticism from somebody that you wouldn’t go to for advice.” I think that that’s a great statement, and it’s the same thing with failures. Somebody that’s going to revel in you having a bit of a hard time is unlikely to be somebody that you want to engage with on a general basis. If you remove the fear of what other people think, what you’re left with is just a growth experience.

What are your thoughts on the trend of companies raising a lot of money, with wild valuations, before even turning a profit?

Having not raised money before and trying to understand the way that the game is played, I was recommended a few investor books. This is a bit tongue in cheek, but I read them, stepped back from it, and I was like, “oh, so it’s a giant Ponzi scheme”. If you’ve bootstrapped your business, you can’t spend a pound until you’ve made a pound, so everything about the business is “how do I get it into profit with cash in the bank?” That is how business exists. I was chatting to this investor, and he was saying, “I’m not really concerned with all of that. What I need to know is that in the second round of fundraising, there’s going to be an increase in value”.

So, it doesn’t necessarily have to be linked to any trading, it just has to be that the story is now more powerful than it was to start with. We see this played out to an extreme example with things like WeWork, where the story gets more and more fantastical, increasing that value more and more. I find that fascinating and highly disturbing at the same time because this imaginary valuation of this imaginary unicorn (and we even use the word unicorn!) is actually being given a lot of resources and, as a result of this valuation, that enables people to have these giant super yachts whilst we’ve got a cost-of-living crisis and people really struggling.

What makes a great business leader?

I think that the best trait for a business leader is self-reflection. Also, being able to appreciate the things that you, perhaps, haven’t got quite right and make some changes to move forward.