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Let’s talk: Coulda, woulda, shoulda



Featured | Leadership | Let's Talk

By Loren Webb

This week we asked business leaders what they’ve learned throughout their career; the highs and the lows, and importantly the lessons they have learnt from the journey. 

Sharing with you their first-hand stories on what has worked for them, we provide you with over fifteen expert commentaries on what you should do the first time round with your business so you can avoid the pitfalls.

What are your ‘coulda, woulda, shoulda’ moments?


Stephen Barnes, Principal of Byronvale advisors and author of Run Your Business Better

Most businesses start where the founder is a great practitioner with skills learned or acquired through experience.  When they meet someone and are asked what they do say the practitioner skill – I’m a hairdresser, I’m a driving instructor etc.  More often than not they do not say they are a business owner.  When you start a business, you become a business owner first and foremost. Where most business struggle though is that they lack one area of expertise – practical business skills – in marketing, planning, accounting, sales etc.  Tasks in these areas are either ignored or not given enough attention.  You need to work on your business and not in your business.  I haven’t heard of too many hairdressers, driving instructors etc. going out of business because they are bad hairdressers, driving instructors etc. – rather because they did not become skilled at running a business.

Heath Fitzpatrick, COO at ebroker 

Over time, I’ve learnt it’s crucial to get the right people around you when starting a business. If you don’t have the right people, everything you try to do to motivate and drive them won’t be successful. If you have a business partner, understand their strengths and weaknesses early on. Listen don’t just hear; actively listen when people speak. Take the time to evaluate, take it all in and create the headspace to sift through what’s of value to you. Don’t get caught up in the running of your start up without stepping back. Don’t be scared to change direction. Time after time I see small business owners being stubborn, digging in their heels and not adapting along their path. That’s always a mistake. All businesses – especially small and new businesses – must always be nimble.

Steve Traplin, CEO APAC, Groupon

In my career I’ve worked with many small business owners who are passionate and work extremely hard, often 24/7, to get their business off the ground. But the best business in the world isn’t any good if no-one knows about it and you have zero customers. When you begin in business, it can be a confusing process finding the best avenue to market to your target customer — paid advertising is costly, while old-fashioned, offline methods like leaflet drops are not only time-consuming but they also offer limited insights into how successful your promotional campaign has been.

We are very much operating in a digital, mobile first world and Australians are increasingly shopping and being marketed to online – so it makes sense for businesses to be where their customers are and also to ensure their website is mobile optimised. Online marketing can make your business boom, but can be a minefield to navigate, so platforms like Groupon offer real solutions that allow business owners to successfully market in the digital space with minimal risk but lots of reward. What new business owner wouldn’t want increased brand awareness and profitable marketing with no upfront cost?

Ilter Dumduz, CEO & Founder, Blys

Look after yourself! As a founder, you are the main driver and most valuable asset of your business in the early days, so it is absolutely crucial that you treat yourself as such.

Your wellbeing is directly correlated with your performance, which ultimately correlates to the performance of your team and the success of your business.
Especially in the first few years, it’s important to remember that your business journey is a marathon, not a sprint. You need to preserve energy (both mental and physical) for the long road ahead – and create opportunities to recharge and refocus.

Andrew Laurie, entrepreneur, CEO and elite business coach

A common mistake of new business owners is a lack of effective activity. Many business owners focus too much on perfecting business cards or websites rather than generating business. Cash flow is essential and, without it, the business will fail.

Successful business owners must clearly articulate exactly what problems they solve and why they’re different. Just starting a business based on industry-specific skills isn’t enough for success. Business owners starting a skills-based business must recognise that they also need to learn how to run a business in terms of financial management, sales, marketing, and more. These skills aren’t usually taught in vocational training but are essential for a successful, sustainable business.

Effective financial management is also crucial from the beginning, even if it’s just through a free downloadable system at first. Then, as soon as possible, business owners should recruit or outsource to get as much low-value work off their plate as possible.

Pamela Jabbour, CEO of Total Image Group

Patience, Perseverance and Persistence! Starting a new business is never easy and it takes time. As women we are our own biggest critics and more often than not, I hear women sharing stories of self-doubt, guilt and an overall lack of confidence – particularly in the early days of business when it’s really tough to get a win. If you go into it knowing that it will probably take 12months to start getting any big traction in the business it really sets the tone and gives you the confidence to just keep chipping away at it, as tough or frustrating as it may be!

Peter Bowen, co-founder and managing partner of deliberate practice

Starting a successful business is fun, tough and humbling. Along the way I have learnt:

Have a purpose and goal for both the business and for yourself – this will put into perspective all the things that you do that you may not have considered were part of startup life! Including taking out the rubbish and vacuuming!

Fit your oxygen mask first – It’s not a solo endeavour when you start a business, and those close to you (but not in the business) also come for the ride. Recognising this responsibility to others is important, but this doesn’t mean that you should forget about your own needs. Maintaining balance by way of exercise, healthy choices and outside activities will ensure your presence, personality persistence and performance will remain optimal for the long term.

Focus – You need to be a leader in your field to survive, so focus and ensure everyone can pinpoint exactly what it is that you are good at.

Be thankful – Be overt and genuine in your recognition and appreciation to the opportunity, to others who have been involved and to the community and society we are part of.

Alan Manly, CEO of Group Colleges Australia and author of The Unlikely Entrepreneur

Three lessons spring to mind when thinking about starting up a business. Firstly, take a really good idea.  Secondly, find a customer who is prepared to pay the price you need to be viable. Thirdly, treasure the cash generated and use that cash to find more customers thereby creating a cash flow. As an entrepreneur you are responsible to scale up the operation into profit. That means revisiting number one and following through to number three, never losing focus of the customer who pays your bills.  Each time you get to the last point go back to point one and repeat, remembering that when starting up a business you need experience. As Oscar Wilde said “Experience is the hardest kind of teacher. It gives you the test first and the lesson afterward.”

Bo Kitty, business and life coach – founder of Reality Check Coaching

Starting a business is the easy part – keeping it going is the real challenge and having a positive mindset is so important. ‘Failure’ is merely a product of your perspective. It’s astonishing the amount of clients who contact me because of fear of failure – one of the biggest setbacks in business. Mindset is a powerful thing and training your mind to be optimistic is a real art. Two of the main problems I see associated with a failing business or failing process within a business are these:

  • Excuses. Stop making them for why you can’t, won’t or don’t achieve something.
  • Undervaluing. Look at your service or product from an outsider’s point of view. We are our own worst critics, state your worth and don’t waver.

Start by shifting your mindset towards gratitude and optimism. Optimism and gratitude trigger positivity. How you channel that positivity is persistence. Successful business owners and entrepreneurs are special because their optimism never dies. They are fuelled by perceived failures instead, by reframing them as learning experiences.

Danny Lessem, Co-Founder and Chief Executive Officer, ELMO Software:

Two of the most important lessons I’ve learnt involve resilience and actively listening – both to customers and employees. Modern businesses must be solutions-focused and respond quickly to customer needs, adopting a fully customer-centric, agile approach. Through customer feedback, ELMO has crafted a unique product market fit and is constantly enhancing the value we deliver to help our customers grow. Instead of offering a bandaid solution, we are working with our customers and investing in products that meet their needs now and into the future.

Employees are also our strongest business asset and the key to long-term growth. Employees are as valued as our customers; the benefits of investing in our employees and workplace culture are tenfold. Talent recruitment is a challenge in Australia but by focusing on our employee value proposition, ELMO has achieved sustainable growth through attracting, hiring and retaining the best possible people for the job. After all, your people are your brand… and your biggest brand advocates.

Nick Humphreys, co-founder and Creative Director at Linktree

If I could go back and give myself any advice before launching Linktree, it would be around scaling responsibly and knowing when to hire.

I don’t think any of us could have anticipated how quickly Linktree would take off — it’s grown to over three million users within three years — which meant that in the early days our small team was under an incredible amount of pressure to meet demand.

The ability to hire generally comes down to cost and affordability. We quickly learned, however, that an initial reluctance to hire resources, can lead to hiring under pressure further down the line. Bringing people on to run the daily admin tasks like invoicing, office management or HR, frees you up to focus on what you are good at, and the business grows exponentially as a result.

As the old saying goes, hindsight’s a beautiful thing.

Dipra Ray, CEO and managing director of mPort

I’ve learnt a huge amount from being able to start and grow businesses over time. Firstly, everything takes a lot longer and costs a lot more than you’ll ever imagine. It’s an old cliche but it is so true. Secondly, focus on cash revenue and working capital more than anything else. The days of being able to funded while running constant losses are far and few (and not something you want to risk to chance). Thirdly, culture beats everything else. The people truly make the business – even if you have a great product, if your team isn’t great, the end outcome will always be the same. Therefore, if there’s a toxic person in the team, the best thing to do is to remove them as soon as possible.

Mat Colbron, CEO and cofounder of Tell Me Baby

The most valuable lessons I have learnt in starting a business is to give yourself as much runway as possible. You aren’t going to have the ideal solution or model on day one. You will have to pivot and adjust to what you find is working for your customers. The longer you stick to a plan and idea, the likelihood of success increases, so give yourself as much time to succeed however possible – where it be through bootstrapping, sweat equity and capital raising. Building a business in the early days is like building the aeroplane while you are flying it.

Looking back, as a tech company it would’ve been beneficial to bring in someone with more senior experience with technology into the business sooner, considering I don’t have a tech background myself. We’ve been fine with what I could afford, but I always wonder how further along we would be now, if I had brought someone in sooner.

Also be careful of the advice you are given, as well as the people giving that advice. Double and cross check it especially in areas you aren’t an expert. In early stage funding, I should have created more options for the business and had a plan B, C and D.

And finally whatever you are planning – remember it will take twice as much money and twice as long as you expect. Build in buffers.

Rudy Crous, CEO and co-founder of Shortlyster 

One of the most valuable lessons I’ve learnt from starting Shortlyster is that as a founder you must learn to let go of control over certain aspects of the business when the time comes. At the very beginning of Shortlyster, I was required to wear many hats. I was the CEO along with everything else – customer service, technical support, business development, admin, marketing and more. Eventually, as our business scaled up, I’ve had to learn to let go of control over these things and hire people who are better suited to taking on those responsibilities. This is crucial for business success, as I need to be able to focus my energy on only the most important matters that will propel the business forward. At times this can be hard, but it’s something all business owners have to go through. It’s essential to hire people you trust to get the job done, leaving you to focus on the more important things.

Yanir Yakutiel, CEO and founder of Lumi

During Lumi’s second funding round, we secured $8 million, bringing the total investment to almost $40 million. To share our achievements is easy but it hasn’t been a walk in the park. Here are three lessons I’ve learned from starting up my businesses:

  1. Surround yourself with the right people. They’re your best asset.

We’re fortunate to have developed a dynamic team – it’s been crucial to our success. Connect with those that can get on board with your vision and mission.

  1. Be adaptable and persistent.

Things will not always work out exactly as you planned, and everything changes in time. Keep committed to your vision and focus on progress rather than perfection.

  1. Perfect is the enemy of done. Things need to be done quickly. Make sure things get done quickly as the to-do lists get longer and longer regardless of how many items you manage to tick off.

Paul Murray, COO idSafe and Wontok

Having the right team around you is critical when starting a business. You don’t have time or budget to waste, and you need people with the right skills and the right personalities to collaborate and work together. At the start, all roles are highly strategic, even your admin. Hiring the right or wrong fit for your business can make or break it: it’s important to invest in people who share the same goals, values, and vision.

“It may be that certain people are the right people at different times. Knowing when to let people go is critical: not everyone can travel all the way with you. As a business evolves, it needs different skills and approaches. But at every stage, you need the right talent for that moment in time while anticipating future needs.

Emma Lo Russo, CEO, Digivizer

Hindsight is an amazing thing that you can only apply moving forward. Key things I have learned that I wish I recognised earlier: first, focus on what drives the greatest long-term value for your company. For us it is our technology platform. It is not something that will develop without the full driving force and attention of the CEO, and the entire company understanding its vision, objectives and key success measures. It is too easy to be distracted by shorter-term opportunities.

Second, invest in the best people you can hire who are critical to your long term success. When growing, you need different skills at different stages. So for non-critical projects and shorter-term focused work, consider employees on contracts to give you maximum flexibility and leverage. Moving fast becomes a key capability you need for your business.

Roby Sharon-Zipser, CEO and Co-Founder, hipages

We started hipages in a garage on just a $5,000 credit limit. We quickly learned that you don’t need a flashy office to start a business. When you have a great idea that serves a market need, it’s all about building on that and dedicating your capital to the product and service development. Once you’ve passed your early growth phases, and looking to employ team members beyond those with a stake in the company, that’s when you start considering workplace investments.

Today we have a team of more than 250 talented, dedicated and passionate people. Over the past 15 years of hipages, I’ve learned how incredibly important it is to empower and listen to the ideas of all. Strong business ideas can come from anywhere, and it’s often those quieter team members who should in fact have the loudest voice. So make sure you give your team members the respect and spotlight they deserve, by regularly seeking their feedback on challenges or opportunities relevant to their expertise. Great companies are built by a collective of great people, after all.

I’d also say that when starting out, you want to constantly run at 100km/h. But I’ve learned how important it is to maintain control and slow it down. While you want the customer to have everything right away, you also can’t burn out your staff and it’s important they’re happy in their roles. You need equal commitment to the customer and the culture.