We use cookies to enhance your experience on our website, and to track traffic and campaigns. If you continue to use this site, we’ll assume you’re cool with that. If you want to find out more about cookies, including how to disable them, please head on over to our cookie policy.

"I’m a start-up guy. I love the scrap, the feeling of success against the odds."

Simon Dennett
Career stories

In the first of a series of stories about how people have forged their careers, and the decisions they've made along the way; we hear from Voco's co-founder, Simon, on the choices he's made and the lessons he's learned.

I’d describe myself as a massive generalist when it comes to my career. I don’t really fit in a box and I am not sure I really want to. I have always hated the “what do you do?” question at parties. I either dodge it completely or launch into a very long winded rambling explanation that leaves the other person wondering why they ever asked. 

Like many people I had no clear vocation or passion to follow, I was pretty good at most things so I chose a route that would expose me to lots of different opportunities. What I was clear on is that I loved variety, change and challenge.  

When I look back to my school days, I can see that I was always interested in entrepreneurship. I loved problem solving and overcoming the odds, and I always had a deep rooted confidence that I’d be able to do something significant. As a bit of an introvert, I never saw myself as a bombastic self-made business leader, but I knew I liked the idea of being accountable to myself. 

Making a switch

I’m not really sure why I chose to study Computer Science at university. It was the late 90s, the tech wave was here but it wasn’t as all dominating as it seems today. I recognised that I wanted to be part of that wave perhaps, but I just wasn’t sure how. I was always good at maths and science but I was never one of those kids into fiddling around with code. I preferred playing football. 

Perhaps unsurprisingly, I quickly found I hated my course; I felt stupid every time I walked into a lecture, and while I liked the logic of programming, I found writing code really difficult. I finished my first year but then switched to study Physics, which was a better fit as it was more theoretical, and less focused on knowing where to place a semicolon! I think it’s easy to make a change when you know something is really wrong for you; you have to trust your judgement.

I graduated from university in 2002 - bang into the middle of a recession - so I felt pretty lucky to get a consulting job, albeit it in a pretty niche firm. I was drawn to management consulting because it would expose me to a wide range of businesses and functions, and I found myself working on interesting projects and visiting interesting places. But I couldn’t settle.

Ignoring the conventional path

I wasn’t quite ready to go it alone, I flirted with the idea of doing an MBA or banking a few years in a bigger, branded strategy consulting firm; I even had offers on the table. That would definitely have been the conventional path for me, but instead I was tempted by the idea of a start-up where I’d be able to get more hands-on experience of building a business. So I found myself in a damp South London basement interviewing for a poorly defined, slightly nebulous role in a new tech company that was looking to disrupt the music industry.

I took the job and ended up staying for over ten years. In that time the company grew from a handful of people to almost 1000; a plucky start-up to a success story, with offices across the globe, really significant revenues and a big valuation. My role and environment changed every three months. I became one of a handful of decision makers that drove that growth progressing through to C-Suite roles in strategy, innovation, operations, commercial and product, and spent five years working in New York City. It was an incredible ride.

It wasn’t all great though; my first year was tough. Because the company was so small, I had to do some pretty underwhelming and repetitive things. But I really liked the founders - they felt like the kind of people I aspired to be - so I stayed. 

I had a few side hustles where I was exploring ideas of my own for potential businesses. This helped. It gave me an outlet to push the boundaries of my skill set and balance some of the monotony of the early responsibilities I had at work. 

None of my hustles went anywhere, but what did change from taking them on was me. They built my confidence. I started being honest and open about my opinions at my day job. I argued for new strategies and approaches, I took on tasks that I wasn’t qualified for on paper. After that everything changed. I became firmly established as one of a very small group of leaders in the business and lived the experience of exponential growth and all its joys and challenges. My day job became my passion.

I’m really proud of what we all achieved over the time I was there. It’s incredibly rewarding to be able to look back and pinpoint the contributions you made to something material. But I’m equally proud of balancing this success and growth story with my own values and integrity. High growth companies are often seen as being aggressive or competitive, but that wasn’t my experience. The founders had really high moral integrity, that rubbed off on the culture and fitted my authentic self well. I can very honestly say I made progress without ever being an a***hole or consciously stepping on someone else. I am very proud of that.

Learning to believe in myself

I thrive when I’m collaborating with others trying to solve hard problems as a team; I love being surrounded by smart people who bring interesting and diverse perspectives. I think that’s why the start-up space is so compelling for me; you have a group of people all trying to do the best they can with limited resources, making big choices based on often imperfect information. 

You just have to hope you get things right more often than you get them wrong. And once you realise that everyone’s playing that game - and that you are pretty good at it - it’s an incredible tonic for self doubt. That was important to me as I have always suffered from imposter syndrome. The voices in your head that tell you that you're not good enough or don’t know as much as the person next to you. They can be loud. But this start-up tonic soothed my demons and I started to believe in myself more and more.

There’s an insane sense of camaraderie when you’re all trying to put a rocket into space and you have no idea where to start. But when you work together to break the challenge down into small, achievable steps and trust that your intuitions are on average more right than wrong, you slowly and incrementally build a path forward.

I was lucky to have people on my side at each stage of this journey. There are three people I can specifically point to, I hope they know who they are. They all played a different role; from encouraging me to share my opinions, to challenging my thinking and advising me on where to focus next. They were pivotal in making me see myself differently and pushing me to achieve something significant. It’s easy to underestimate the power of having someone on your side, or to think you’d have got there anyway, but in reality it’s transformative. 

Knowing when to leave the party

I’m a start-up guy. I love the scrap, the feeling of success against the odds. I also love championing people, making sure they feel motivated and valued, leading with empathy and vision. It’s vital in small, growing companies but, in my experience, it gets harder as they scale. You need more process and rigour; there are policies and formalities, and while your impact can be multiplied by having a larger team, the day-to-day of the job is as much around marshalling collective, consistent progress in the team as it is about being in the thick of solving knotty problems. I can do all that stuff, but I realised over time that it isn't where I get my energy from. That's why big companies hold little real appeal for me.

So if I have one regret it’s that I stayed too long. I had an amazing run, but following a return to London from New York a few years ago, I felt the company had grown to the point that it no longer held that special magic for me. It was no longer about working at the absolute limits of your knowledge and experience to make things happen; instead it was an established and respected organisation that others wanted to disrupt. I’m tremendously proud of the role I played in getting it there, but I wish I’d tapped out before the emotional connection diminished for me.

What's next?

We’re living in a strange world at the moment, but the confluence of the end of my run and the onset of a global pandemic has actually given me time to reflect and focus on what I really want to do next. And that’s co-founding and building my own company, focusing on one of the areas I feel most passionate about: people. I want to use my breadth of experience and love of the scrap to build something that can really help people take control of their careers and be their best. 

My priorities are different now, I have responsibilities - children, mortgages etc - that I didn't have when I sat in that dingy South London basement; but my focus on finding exciting challenges and opportunities that allow me to solve problems and make a positive impact on the world hasn’t changed. I still have that fire in me and I am excited to get back into the scrap.

I generally sleep well at night but on the occasions that I do find myself awake, worrying about whether we’ll succeed, I embrace those fears and remind myself that I’m at my best when I’m in over my head, about how I love being the underdog and solving unsolvable problems, about how on average my commercial instincts are good. I then have a cup of tea and watch the sun come up.

Advice to my 20 year old self

  • Trust your instincts, they are much better than you think
  • The majority of people are making it up, don’t be intimidated by confidence
  • It is hard to notice when you are gradually becoming disengaged at work. Build a repeated, scheduled habit of testing your happiness. When you notice sustained change, act on it.
  • Be proud of your fundamental self and your values. They are non-negotiable. If they do not fit with your work environment, make a change. Never contemplate trying to be something you are not.

Stay in touch

Subscribe to our newsletter to  find out more about harnessing  the power of peers to build a connected, inclusive learning culture in the new world of work.