Advice for my kids after 20 years of startup life.

by | Jan 2023 | Updates

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After a profitable but unfulfilling career start in IT sales and then recruitment, I took a year out to travel the world. From Argentina I worked my way up through mid-South America, then flew to Mexico City before criss-crossing down Central America to Honduras.

One year soon turned into two. I went on to spend 6 months in New Zealand, where I tried every adrenaline sport Queenstown had to offer, learned to fly hang gliders, and even worked as a commentator on an amphibious “duck”. Finally, to top it all off, I spent a year working around Australia, doing everything from building and test-flying hang gliders to pouring my first ever cocktails (unbelievably poorly), painting a yacht, and “pearl farming” in Broome.

Since then, with only two exceptions, I’ve worked for myself.

After trying many diverse kinds of work and meeting people from all different backgrounds, locations and careers, I realised that what’s ideal for one person is anathema to another. I met doctors who wanted to be lawyers, lawyers who wanted to be doctors, teachers who wanted to be in television, and media people who yearned for anything that would keep them out of the spotlight!

When I look at my children, who are now 7 and 3 (turning 4 tomorrow!), I wonder, with so many differing opinions, how I can help them prepare to make good decisions. Not only that, but what can I teach them that will still be relevant in a world that inevitably will be so different from mine? As I write this, almost every other headline mentions OpenAI and its “ChatGPT” chatbot, which appears to be disrupting industries left, right and centre.

Advice that stands the test of time

The advice below comes from my 20 years in business, travelling, investing and working with entrepreneurs. Some points are lessons learned from my own mistakes and business failures; others have been garnered over two decades of working with intelligent, successful people; the rest I’ve saved over the years as things I felt my children, one day, may benefit from hearing.

If you can help improve this collection please let me know! Here’s the list:


  • Put integrity and kindness above all things.
  • Be brave but not reckless.
  • Be humble, polite and respectful.
  • Be loyal, reliable and helpful.
  • Be open about weaknesses and fears.
  • Be accountable and own your mistakes.
  • Do the right thing.


  • Take the risk to walk your own path.
  • Do what you enjoy and find easy that others dislike and find hard.
  • Don’t let life happen by accident. Allocate your time to what matters.
  • Try to say yes but have the strength to say no.
  • Become the world’s best at whatever it is you’re passionate about.
  • Build positive habits and create friction around negative ones.
  • Forgive quickly; love slowly.


  • Treat others as you want others to treat you.
  • Embrace criticism but ignore hate.
  • Surround yourself with smart, kind, honest, energetic people.
  • Work with the best, even if you have to work for free.
  • Don’t compare or complain, offer fixes to whatever is broken.
  • Prioritise giving over receiving, especially credit for success.
  • Be the person people come to when they need something done.


  • Ask the stupid question and learn how to listen.
  • Seek advice, responsibility and experience to find what you love.
  • Work hard. If you can’t be #1 for results, be #1 for effort.
  • Keep learning – at the very least it will make you more interesting.
  • Take care of your body and mind with sleep, diet and exercise.
  • Dedicate time to pursue hobbies that bring you joy.
  • Spend quality time in the natural world.


  • Treat life as a journey to enjoy, not a destination to reach.
  • Learn how reputation, work and wealth can compound.
  • Learn to leverage capital, software, media, or all three.
  • Choose wealth over income.
  • Aim to own undervalued assets that are likely to appreciate.
  • Invest in what you know well and believe in.
  • Codify what works to create effective systems, not outcomes.


  • Be fair but realise life is not.
  • Raise your voice only in encouragement, not in anger.
  • Success won’t make you happy, healthy, or loved.
  • …Being happy, healthy and loved is success.
  • Realise life’s greatest experiences may lie beyond your fear.
  • Always give a second chance, but never a third.
  • Pick your battles then let the rest wash over you.

What did I miss?

Image credit

– Featured image by James Lee.

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