Five Lessons From A Sydney Entrepreneur On How To Take The Right Risks

Photos by Boaz

Sally Hill is Founding Director of Wildwon, the meaningful experience agency, and a World Economic Forum Global Shaper.

Approx 9 minute reading time

In business and life, it pays to challenge the status-quo and follow your passion. Around the world we’re seeing new brands, businesses and markets emerge as a result of collective risk taking. Even in our own backyard, our city is full of disruptive innovators.

At a recent event – Idea Bombing Sydney at Paramount House – I was one of an all female line up of entrepreneurs asked to contribute ideas for our city which answered the question: ‘how can we make Sydney better by taking more risks?’ but also took into account the difference between good risk and bad.

Here are five lessons I’ve learned about the right kind of risk while starting my business, Wildwon, which are also valuable considerations for the shaping of our cities.

1. The goals must be bold.

As a business, we have very bold goals.

When we started Wildwon we set out to:
a) completely disrupt the events industry by applying totally new approaches to it. That is, taking our skills from the worlds of digital communications, user experience design and web development – and applying them to the design of real world events and experiences; and
b) run a business that is purpose-led. By this, we mean that our purpose – to create meaningful experiences that galvanise the communities we care about to achieve their common goals – is the primary factor in decisions that shape our business. Sure, profit might follow, but never comes first.

Sure, profit might follow, but never comes first.

Two years down the track from starting up, and in our day-to-day work, we still find we work best when we create huge goals for ourselves and take enormous leaps out of our comfort zone. We have the most fun, and the most intense periods of learning, when we’ve taken a huge jump forward and learned while we’re in the air.

When it comes to the design of and vision for our cities, we’re working on huge horizons – 20, 50, maybe 100 years. So the goals need to be almost outrageously bold, and the comfort with risk even greater than in startup business, in order to keep our cities clever, relevant and future-proof.

2. Where there are lemons, there’s lemonade

Entrepreneurs know that where there’s a rub, where there’s friction in a process, where there’s a gap where a product should be, but doesn’t exist yet, there’s usually a huge business opportunity. If you’re angry about something, there’s a very good chance that other people are too.

At the start of my career, I didn’t identify as an entrepreneur. The rub, for me, was the way companies were treating people and the deep ecological hole we were digging ourselves. So I gravitated toward activism and worked as an environmental and social justice campaigner for a few years.

Then I decided I wasn’t having enough impact doing this, and I wanted to be where the action was: working inside these companies in Corporate Social Responsibility (CSR). It wasn’t long before I realised that the corporate sector, even in (or especially in) a sustainability role, was not the place to be for someone who valued risk-taking and values-led leadership.

I realised that the kind of company I wanted to work for and wanted to see in the world didn’t exist yet. So this early frustration became the start of a journey toward creating my own purpose-driven and B Corp certified business.

Now, think of the issues that create the most anger in our city: congestion, poor public transport, lock-outs, the fact that you can’t top up your opal card in a train station, the fact that there are people sleeping on the street at night in one of the wealthiest countries in the world – or whatever it is for you. These are the areas ready to be disrupted by breakthrough ideas, and the areas which provide the greatest opportunities to make leaps and bounds in the way we organise ourselves in cities.

3. We need visionaries, not profiteers

One of the most important lessons I’ve learned in our unconventional but successful style of doing business is that if you have a strong vision and strong purpose, the profit, or the prosperity, follows. But you can’t start there.

As I’ve mentioned, we’re part of a growing movement of purpose-led companies who are finding out that when you have purpose you have great customer loyalty, a secure supply chain, a well-loved brand and a compelling story to tell – today’s fastest growing companies have nailed this.

Now, cities are not companies, so there’s even more reason why they should be purpose-led rather than profit-led. But we have seen them fall victim to the same short-term, profit-driven thinking that causes companies and cities a like to fall into patterns of irresponsible and short-sighted decision-making.

Imagine, for a moment, that a visionary was responsible for designing a city like Sydney. They might come up with a city of tree-lined streets, beautiful parks, smart buildings, happy and healthy people, cycling infrastructure so good that that traffic and petrol fumes were a bad memory, entrepreneurial hubs with new businesses, hell, whole new industries flourishing in them. All of the things I’ve mentioned would reward the city in all sorts of lovely intangible ways, but they would also reward the city economically in terms of liveability, tourism and the flourishing of industry.

We might have more projects like The High Line – a truly visionary project in New York where a disused train line was converted into a public thoroughfare and “park in the sky”, which is paying off economically again and again. For example, there is NO crime on the highline. I repeat, there has not been a single incidence of crime on this particular corridor of New York’s landscape. There is green-star rated, architecturally designed residential developments cropping up next to and overlooking the High Line, to match its green, progressive and community-oriented design.

Imagine, for another moment, that a profiteer, or profiteers, were calling the shots. We might see community and public space turned into private space, property prices in inner-city suburbs destroying diversity, developers close down cultural venues, we’d see exciting projects like toll roads and casinos put forward for us to get excited about. This is where we are now.

4. Play & prototyping

In business today, the companies leading the pack are the ones who are skilled at rapid prototyping, experimentation, getting new features and products tested quickly, gathering feedback early, and subsequently refining and releasing fantastic products and features, without wasting time and money on average ones.

Successful cities are doing the same thing.

One example comes, again, from New York. Janette Sadiq-Khan is the commissioner of the New York Department of Transport and her mantra is: “Do bold experiments that are cheap to try out”. Her nimble style of tactical-urbanism has been key to her success. One of her most famous projects is Times Square, where she wanted to introduce out car-free zones. To do this, she used temporary paint to mark out new pedestrian zones, bike lanes, green space and space for people to sit and relax, and then watched to see how people responded before rolling it out for real. Of course, people loved it, and there are now car-free zones in Times Square.

Another great example comes from Dallas, Texas. The pair who created the successful ‘Better Block’ project started out with a slightly different guerrilla-style project. They wanted to bring back the ‘streetcar’ (similar to a tram or light rail) that ran from Downtown Dallas to Oak Cliff so they started a faux website for the ‘OCTA’ or the Oak Cliff Transport Authority and announced on this website the return of the Oak Cliff street car. It looked so legitimate (there was even a 3D render of the trolley travelling through the streets) and attracted so much support and local news attention that the real transport authority had to do bring it back. The Oak Cliff streetcar began service again this year.

5. Culture must be intentional, not left to chance.

One of our biggest goals as a business is cultivating a great culture. And key to this, we think, is creating an entrepreneurial culture in our employees – or entre-employees if you will. This sounds counter-intuitive because we’ve traditionally recognised founders and owners as those with big dreams and plans, and employees as those doing the grunt work. Well, we recognise that everyone who works with us is an individual with their own goals, aspirations and ideas. If we expect them to help us make our dreams a reality, we ought to support them get up their own ideas, inside our business as internal projects and experiments, and outside of our business as side projects.

Just as the founder and entrepreneur mindset infused through every layer of the organisation is a positive thing, I would say the same for having a councillor, leader and fixer mindset infused throughout every resident of a city. Imagine if a council’s attitude was that the care-taking, stewardship and shaping of the city didn’t just rest with them, but rested with every one of the people who live there, and supported people to do take on this role. Cities and neighbourhoods are always creating and recreating themselves anyway, so a culture that turbocharges this creativity and neighbourhood improvement could be actively shaped. If we were to encourage an entrepreneurial culture on top of this – where people fixed problems themselves with innovation – hacking our way to beautiful and functional cities – we would have an incredibly diverse, interesting and economically resilient city. So if cities want a similar culture of leadership, self-organised citizens, urban improvement and good risk taking, this has to be fostered. In return they’ll harness an army of entrepreneurial risk-takers and problem-solvers. City of Sydney is off to a great start with their grants program – with the catchy tagline ‘less grunt, more grant’.

If we were to encourage an entrepreneurial culture on top of this – where people fixed problems themselves with innovation – hacking our way to beautiful and functional cities – we would have an incredibly diverse, interesting and economically resilient city.

And finally – because it’s topical – risk and experimentation is not possible when you live pay-check to pay-check and work your butt off just to pay rent. We need affordable space to live that lets people breathe, we need affordable space for artists and students who make our cities buzz, we need space and time for people to tinker and create and live and learn.. not just space to work. The biggest risk we face is of Sydney becoming the most boring city in the world because only the rich can afford to live here.