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"I like the scrap, the feeling of success against the odds."

By
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 long winded explanation that leaves the other person wondering why they asked. 

Like many people I had no clear vocation or obvious passion to follow, I was passably good at a broad set of things so I always looked for routes 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. As a bit of an introvert, I never saw myself as a bombastic 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. 

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 tough. 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 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 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 - 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 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 over 1000; a plucky start-up to a success story, with offices across the world, really significant revenues and a big valuation. My role and environment changed every three months. I became one of a small set of people 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 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 small group of leaders in the business and lived the experience of exponential growth and all its joys and challenges. My day job very much 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 that 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 do thrive when I’m collaborating with others and 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 fairly good at it - it’s an incredible tonic for self doubt. That was important to me as, like many people, I have always had a touch of 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 forward. 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

If I have one regret it’s that I stayed a bit too long. I had an amazing run, but following a return to London from New York, I felt the company had grown to the point that it no longer held that special magic for me. I’m tremendously proud of the role I played in growing that business, but I wish I’d tapped out before the emotional connection diminished for me.

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.

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