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7 Steps To Surviving Your Entrepreneurial Journey

My trusty Converse trainers have been taking me places ever since I was a student.

Whether I’m racing from the school gate to the office in the mornings, running up and down stairs at Unruly HQ or racking up the air miles travelling between Unruly’s offices in Asia, America and Europe, my All Stars have been with me on the journey every step of the way.

But what have they taught me about surviving the entrepreneurial journey?


1.Don’t be afraid to break the rules and do be prepared to look stupid as you start up, especially when you’re out there sharing your untested, unproven idea.

I appreciate that writing an article about a pair of beaten-up Converse trainers may seem a bit odd, but you have to admit it’s memorable! Don’t be afraid to do something different, to try something that will get you noticed.


2. Be lean. Reduce, re-use, re-cycle wherever you can as you grow your business. I wear my Converse until the soles are worn through and the tongues hang off – they don’t always look the smartest but they do the job! And this is the key message – if there’s a simpler, cheaper, faster way to do something, do that to begin with while you’re market-testing your idea.

I wish I’d known what a brake on growth perfectionism can be! Release the minimum viable product (MVP) and get market feedback before building out the bells and whistles on your product.

And never blame a lack of funds for holding back growth – social media, cloud-hosting, remote productivity tools all make it cheaper than ever before to start and grow a business. And at the end of the day – imagination trumps  big budgets!


3. Be Agile.  As a mode of transport, these sneakers are perhaps the most humble – they may not be a racing bike, they may not be a 737, but you can pop them on and just get going, you can move around unseen and you can go places a 737 cannot.

Being nimble is key as you build out the product and seek feedback; be prepared to pivot if you see a bigger problem you could solve. You need to move quickly – I’ve seen so many entrepreneurs hold ideas close to their chest, paralysed by fear of being copied, only to see someone else have the same idea and execute it super fast.


4. Pace yourself – scaling up is a marathon not a sprint. Think about managing fast and slow, strategising fast and slow and balancing short-term battles with winning the bigger war.

At Unruly, we’ve got much better at this over the years, as we’ve rolled out Agile methodologies across the business, and supplemented this rapid-delivery approach with a second organizational framework – Patrick Lencioni’s Strategic Playbook approach – to give a longer term lens.


5. Think in pairs. Great individuals don’t build successful companies; great teams build successful companies. In other words, one shoe is not going to get you very far!!!

At Unruly, we practise XP (eXtreme Programming), where developers code in pairs and we have built out this methodology to apply to other teams across the business – configuring campaigns in pairs, writing press releases in pairs. The power of two – as we saw with Noah’s Ark – is procreative and creative, can be a multiplier effect and a power-up – both for the individuals and for the company. It’s also a great way to turbo boost the career progress and professional development of talented, younger team members.


6. One tongue, ten eyes…Just as each sneaker has one tongue and ten eyes, it’s important for entrepreneurs to take the time to look around the market, watch competitors and watch what’s going on with consumer behaviour.

It’s easy to get wrapped up in the day-to-day running of your business, but think of mechanisms for guarding against this. At Unruly we have a pioneer programme where Unrulies who are passionate about a subject area work in pairs to keep the rest of the company up to speed on their topic.  It’s not just about facts and data. To scale your business, you’ll need to build empathy – with your staff, your customers and your investors. And to do this, you need to understand their journey too.

Listening and learning from your peers at other start-ups can be invaluable source of information and support. What are their challenges and how have they solved them? Most helpful to me during the early days of Unruly was the Tech COO group where I met amazing founders and start-up execs such as Pete Smith (Songkick, Silicon Milk Roundabout), Divinia Knowles and I could learn from their wisdom!


7. Be yourself – everybody else is already taken. Trust Oscar Wilde to say it best! These shoes – or their parents and grandparents –  have been with me for decades. You might be a stiletto or an Ugg boot or a pair of Nike trainers, but these shoes remind me of who I am today, where I’ve come from and where I’m going.  No matter that they’re leaky. They keep me grounded. And when you’re hanging on for dear life as you ride the entrepreneurial roller coaster, a little bit of groundedness goes a long way.

If you’re up for a chat about entrepreneurship, then come and say hello on blab.im, where I host The StartUp Show. It’ll be fun 🙂