There’s a heightened romanticism around entrepreneurship that often impacts our sense of reality in the early days of starting a business. The ‘hollywoodised’ version of startups would have us believe that’s it’s all about building an app, making millions overnight and then sitting back on a beach to enjoy it.

However the reality of building and running a business is a far cry from the fantasy that exists around it. In fact entrepreneurship is more like being in a relationship. Like any strong relationship, it takes time to build. It takes commitment. It takes passion. And it takes hard work.

It’s not always perfect – most of the time you love it, occasionally you hate, but ultimately if you’re in it for the right reasons then the hard work is all worth it in the end.

In the spirit of Valentine’s Day, we spoke to some of Australia’s most successful entrepreneurs about their love-hate relationship with entrepreneurship:



Justin Dry, Co-founder & Joint CEO of Vinomofo

LOVE: The freedom to turn my ideas and dreams into reality.

HATE: Having to make the really tough calls around people you care deeply about. Businesses and people often outgrow each other and it’s the best to deal with it as early as possible but it can really hurt.



Taryn Williams, Founder & CEO of

LOVE: I love solving problems, and running a business is solving problems every day in different ways! I love finding the right combination of people, skills, resources, technology to make things happen and seeing a solution come to life. It never gets old for me!

HATE: The guilt that comes with never having enough time for everything. Never having enough time to mentor each person on your team, spend quality time with your partner, post those Christmas cards, clean my desk. I am sure at any moment I am feeling constantly guilty about something!



Peter Bradd, Co-founder & CEO of The Entourage Beanstalk Factory

LOVE: I love dreaming big and sharing my vision with others and then having them help me make it a reality. I love creating an organisation to carry out my mission, working it out together with my team of great people who believe in me and my mission and exceeding the catalytic change we set out to achieve.

HATE: I hate when people choose the safe and well-worn part over something that deep down they believe in, but is a little more unknown. I hate those times people choose to blame others over taking responsibility themselves for an outcome. I hate data entry and keeping my operational models up to date!



Peter Moriarty, Founder & Managing Director of itGenius

LOVE: Lots of travel keeps things interesting… using our tools I’m lucky enough to be able to work from any location and I often do. I like to tack on a few days of personal travel with work trips and that allows me to see the world and be inspired by other cultures and markets.

HATE: The biggest challenge would probably be maintaining a balance of connectedness and community support for our customers, while making sure I have adequate personal and family time.


Lorraine Murphy, Founder & Managing Director of The Remarkables Group

LOVE: The freedom to create whatever the hell I want.

HATEI don’t think I could pinpoint one specific thing, however I’ve found that there seem to be phases where multiple areas (team, clients, cash flow, failed ventures) are problematic at the same time, and it’s tough to haul myself out of that funk and get back into an upswing again.



Simon Griffiths, Co-Founder & Head Honcho of Who Gives a Crap

LOVE: We started Who Gives A Crap when we learnt that 2.5 billion people (now 2.3 billion!) didn’t have access to a toilet.  We saw an opportunity to use a product that everyone needs to help people in need.  The impact that we have is definitely my first and biggest love when it comes to running the business.  My second love is the feeling of building something, and knowing that I’m personally growing and learning more every single day.

HATE: One of the hardest parts of running a business is finding the time to disconnect and switch off. Usually the first week of my holidays are filled with last minute requests and questions, and then I get bombarded just before I return to work. As a result I often try to take long breaks so that I know I’ll get at least a few days in the middle where I can completely switch off!



Dorry Kordahi, Co- founder & Managing Director of DKM Blue

LOVE: The diversity and challenges that being at the helm of a multi-market company brings on a daily basis. My company has numerous subsidiaries in the products and services space, that provides huge scope for challenge and fulfilment.

HATEWhen something that, at first, seems trivial to me interrupts an important task I have at hand. But I know in my heart it is equally important to the smooth running of the company. Because as I say in my book, Power to Act: “A chain is only as strong as its weakest link.” Taking on these things ultimately keeps me fresh and stimulated.


Jane Lu

Jane Lu, Founder & CEO of Showpo

LOVE: It’s really fulfilling and fun – I actually look forward to going to work. As we get bigger, we can hire more specialists and I get to delegate out work that I don’t enjoyed doing or am not good at, and can focus more on the stuff that I love!

HATECan’t chuck sickies.

Jack Delosa, Founder & CEO of The Entourage

LOVE: The most important part of business for me has always been challenging and enabling my team and our students to do their life’s best work and accomplish what even they once thought impossible. Nothing makes me happier than seeing our community exemplifying the impact of this mission.

HATEBeing overly involved in the details and day-to-day administration of the business. We have built a strong team who are really clear on our business objectives, and we have measures and reports in place that allow them to plan and execute day-to-day with guidance from leaders and myself.

Not being involved in the executing the day-to-day operations, doesn’t mean distancing yourself from it altogether. As entrepreneurs we need to be across everything, but that doesn’t equate to doing everything.




Daniel Flynn, Co-founder & Managing Director of Thankyou

LOVE: I love chasing an impossibly bold vision with a bunch of like minded people crazy enough to volunteer for it. I say “volunteer” because even though staff are paid the fact is they could work anywhere they want in the world and they voluntarily choose to work at Thankyou, that’s a big deal.

HATEI see the good in everyone, so I don’t love the tough calls that I have to make that relate to people I know or have built a relationship with, like ending partnerships or supplier relationships. Over the years I’ve learned the importance of making the right calls to protect Thankyou’s vision and goal vs the ones that keep everyone happy (and maybe be more liked by people).  A mentor challenged me one day to not be so shaken by the tough calls. His point was that if the mission we are on at Thankyou is more important than me then what does people liking me or not have to do with it. Fair point.