Week 4: Famous people who would not have made it on their own... without a challenge

From Mike Tyson to Martin Luther King.

Welcome to Week 4. We’re unpacking the eleven things you need to support you working on something bigger than yourself.

👉 we are inundated with myths about success and social contribution — the most important factors are not tangible, and so, we often get lost. This newsletter, for the time being, is very committed to making those footnotes easier to understand and unpack.

Let’s unpack a few people you might know, and deconstruct the importance for them of someone who was willing to challenge them.

‘Tell them about the dream Martin’

Martin Luther King was torn over how to deliver his famous speech at the March on Washington. At a decisive moment, he decided to go off script.

Mahalia Jackson, a musical legend, shouted out from behind King “tell them about the dream, Martin! Tell them about the dream!”

  • King’s I Have a Dream speech is one of, if not the most famous speech of all time. It came at the peak at the USA’s Civil Rights Movement, and set the precedent for other civil rights activism throughout the world.

  • It has given a world permission to follow their dreams.

  • It might never have happened. It wasn’t in the teleprompter (so-to-speak).

Sugar Ray Leonard

Almost didn’t become a boxer. Within seconds of a fight at the No.2 Boys Club outside of Palmer Park he was pounded in the face and lost.

Six years later, his brother urged him to try boxing again.

  • Leonard was the first boxer to earn over $100 million dollars in prizes.

  • From 1978 to 1990, Leonard was a commentator for HBO.

  • From 2001 to 2004, Leonard had a promotional company, SRL Boxing. The company had a deal to promote fights on the first Friday of every month on ESPN II. In addition to promoting the shows, Leonard provided special guest commentary during the broadcasts.

  • Leonard became the host of the boxing reality series The Contender in 2004.

  • The Big Fight: My Life In and Out of the Ring, Leonard's autobiography, was published on June 6, 2011. It became a New York Times bestseller.

The man who saved Mike Tyson

Not sure what the focus is on boxers, but let’s run with it… because Mike Tyson does not think he would have made it had it not been for a coach named Cus D-Amato.

Mike Tyson met him when he was locked up in juvenile detention. Cus would go on to become Tyson’s legal guardian when his mother died.

“If he called me – ‘Mike, I need to talk to you’ – I didn’t feel good going over to him. That’s when he’d start giving me his detailed criticisms of my fights. People see the public celebrations of my sensational knockouts but they don’t hear Cus talking to me alone after the fight.”

  • Tyson, who had an incredible boxing record, credits D’Amato as having turned his life around.


  • Jennifer Doudna thought going to Harvard was a pie-in-the-sky idea. Her Dad said to her something to the effect of, ‘you can’t get in if you don’t apply’. She has pioneered work into CRISPIR gene editing.

  • Steve Jobs says that he would have ended up in gaol had it not been for Imogen Hill, his 4th grade teacher, who looked after him when he was a rebel at school.

  • Jobs was also influenced by Ron Wayne, someone we never hear about. Jobs and Wayne worked together at Atari, and Wayne was unique for one reason — he’d had a hand at running his own business. In the 1970’s, when this wasn’t nearly as common, it gave Jobs permission to think he might be able to do the same.

  • Grant Hackett, Michael Phelps and Ian Thorpe. Elite swimmers, who were competitors… yet, they challenged each other immensely. Thorpe famously goaded Phelps just to get more out of him… billed as competitors, yet, they were friends.

Thoughts! 💡

  1. The Steve Jobs-Ron Wayne story shows the power of an implicit challenge — Wayne never said anything to Jobs, but, he had an impact on him without realising it. It shows the importance of putting yourself in the best possible environment, so you can be indirectly influenced.

How do you know if you’re being ‘challenged’ enough?

Test it this way… when this the last time someone told you to aim higher and level up, from a position of total love?

People don’t do that…

🚫 They do. You need to fix this.

A tip from a pro… choose the right environment

Famous tech investor Naval Ravikant moved to Silicon Valley in 1996 (or thereabouts) to jumpstart his career… if you put yourself in the right place, things can happen.
☝ I would argue that now you can leverage the virtual world to put yourself in an environment that is Silicon-Valley-esque.

We’re actively welcoming ideas on this at Constant Student — the world needs more of these environments, and the power of the virtual world makes it more accessible.

If you’re not in the Room of elites, who is going to send you the signal to level up?

Place yourself in the right environment, and watch things happen.

Find your Scott’s!!

I always challenge people to ‘Find their Scott’s’ — after my high school friend, turned one of many ‘work/life soulmates’. It makes all the difference. Some things Scott and I have worked on together over the years include:

  • Nonprofit work in Nepal

  • Education initiatives in Australian universities

  • Our book, 18 & Lost? So Were We

  • The Constant Student Community

  • Investing in a exciting new company together

But more than a ‘colleague’, Scott is, as my closest friend the person who has challenged me on other areas of life, directly or indirectly, such as:

  • Health

  • Romance

  • Balance

  • Leisure

  • Rest

  • At least 25% of my reading recommendations (initially 90+% of my reading and podcast recommendations, invaluable!)

Scott takes on big and audacious challenges (e.g. espresso), which forces me to take on and think bigger as a result.

Scott’s hunt in packs

As a result of collaborating and doing life alongside people like Scott, I breed more of these ‘Scott’-like relationships (note, there is only one true Scott McKeon, and thank god for that 😉).

Other tight knit collaborators at the moment include people like Andrew Riis, Byron Dempsey, Liam Hounsell, Robby Wade, Jordan Jensen and a ton more I could mention (don’t be offended guys).

So, go and do likewise. Find. Your. Scott’s.

Reading 📚

  • Bezonomics by Brian Dumane (interesting!)

  • The Untethered Soul by Michael Singer — nice and calming, a great deconstruction of big philosophical and spiritual ideas

  • Tribes: We need you to lead us by Seth Godin — loved this one. Blitzed through it. Great for leaders and marketers.

  • Beyond the Skin by my friend Nistha Dube — Wow. This was incredible, beautifully done journey of heartbreak and rediscovery through a touching poetic form.

  • Codebreaker by Walter Isaacson — I’ve put this down for now, but so interesting what is happening with CRISPIR and genetic research.

Remember, my notes and reading recommendations are available here for Constant Student members.