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The 22 Contradictions of an Entrepreneur

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The following is an excerpt from Jack Delosa’s ‘Founder’s Address’ at the inaugural Australian Startup Awards from 2013. This outlines the qualities that Jack considers essential for becoming a great entrepreneur – a timely reminder in the lead up to this year’s Australian Startup Awards which will be held on Saturday, the 2nd of August.

When I started in business, I wanted to succeed gloriously but when my first business failed quietly it gave me the intelligence and resilience to since build some businesses that have succeeded humbly.

But business is a funny game. The reason I personally love business so much is it demands that we ‘be more’ every day. It demands a flexibility that only experience can bring and a focus that only time can teach.

There are many contradictions to being an entrepreneur, most of which are only ever learnt through trial and error, and picked up after persevering through years of confusion. It is my hope that this list will shed some light on the different qualities a great entrepreneur needs in order to navigate the business world of today.

1. It demands that we think of larger visions while honing our attention to detail.

2. It demands that we work harder and smarter, while still finding time for ourselves and those around us.

3. It demands that we work on our weaknesses while recognizing our strengths.

4. It demands that we plan for the losses while we’re celebrating the wins.

5. It demands that we’re tougher on ourselves and others, while being compassionate and empathetic.

6. It demands that we give all of ourselves to the world while still ensuring that we’re taking care of ourselves.

7. It demands that we build a brand in the marketplace, conscious of image, while remembering that that’s not what is truly important.

8. It requires more of us intellectually while also demanding we grow emotionally.

9. It forces us to think long-term while managing the short term.

10. It demands that we become better at understanding people while also being rigorous with the numbers.

11. It demands that we give everything we possibly have to our team, clients and investors while also being a good daughter, son, husband or wife.

12. It demands that we be ruthless with our time management while remembering to live in the present.

13. It requires that we fail fast while holding the belief that we will succeed slow.

14. It requires that we ask the right questions while still giving those around us confidence that we have the answers.

15. It requires us to think of lofty goals, while keeping our feet firmly planted on the ground.

16. It requires us to be a spokesperson for our brand and our business, while acknowledging the most important words we say are the words we say to ourself.

17. It requires us to test, prove and more importantly disprove our assumptions while staying true to our beliefs.

18. It demands that we know exactly who we want to become in the future, while recognizing that we’re doing alright right now.

19. It requires us to have incredibly high standards for ourselves and everyone around us, while remembering we’re all doing the best we can with what we have available.

20. It gives us the hunger to seek council from those who have come before us, and the courage to ultimately listen to our own voice.

21. It requires us to take some things seriously, while remembering it’s all just a game.

22. It gives us the fire in our belly to start, and the strength in our heart to finish.

It is mastering these contradictions and qualities that will qualify you as an entrepreneur. It’s not the money, not the brand, nor the status. It’s about who you become.

About Jack Delosa


Jack Delosa is an entrepreneur and investor who is changing education. He is the founder and CEO of Australia’s largest education institution for entrepreneurs, The Entourage. He is also an investor in growth companies such as Q-Biotics, Martin Jet Pack (ASX:MJP) and eMerchants (ASX:EML), and founded The Entourage Growth Fund, which invests in upstart businesses. He is one of Australia’s leading entrepreneurs, having been listed in the BRW Young Rich List since 2014.

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