016: Habits To Make When You've Hit Rock Bottom with Oliver Jackson

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From growing up in a circus, to building a multi million dollar property portfolio, some jail time and now training for an ultramarathon. Today’s interview with Oliver Jackson is the stuff of movies. 

With more than two-thirds of ex-felons getting rearrested within the first two years of being free,  the probability of an ex-con becoming a successful entrepreneur? Well, not high. When the going got tough, Oliver got focused on what he did want. Society has been known to frown upon ex-offenders with the assumption that they haven’t been rehabilitated enough. With limited options, they are left with only two choices, either go back to crime or become entrepreneurs.

What’s clear is that traditional employment channels aren’t always an option. Survival of the fittest means being mentally fit. Survival depends on them being entrepreneurial enough to generate legitimate income streams for themselves. 

Yes, you can come from somewhere, and yes, you can have a not so pretty past, but that doesn’t have to define where you are going. That was certainly the case for Oliver Jackson, an ex-con who spent two years in prison but managed to change his life for the better. 


  • Getting to know Oliver Jackson (0:40)

  • How it was growing up in a circus (0:50)

  • Oliver’s transition into what he is today (2:31)

  • It’s never too late to learn how to read (4:38)

  • Living the party life (4:55)

  • Prison as a reality check (5:20)

  • The first step towards change (6:23)

  • Life after prison (8:03)

  • Trying to prove to people that he can rebuild himself (9:18)

  • Structure and routine (10:26)

  • Getting things done before people wake up (11:38)

  • Oliver’s current business (12:00)

  • The entrepreneurial spirit (12:40)

  • Building resilience (14:34)

  • How 2020 became his best year despite the pandemic (16:40)

  • Cutting down on junk food (19:16)

  • Switching to a plant-based diet (20:35)

  • The power-down routine (21:20)

  • Top 5 most impactful books (23:50)

  • The best piece of advice to the listeners (25:40)





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Oliver Jackson is the CEO and Founder of Living Property, Living property is a buyers agent who focus on value add investment properties Australia wide, whether that’s through renovation, subdivision of development. 


Oliver started this business after spending a decade in the construction industry and building his own multi million dollar portfolio using this strategy. Living property was organically created out of hard work, love and passion for property.

Outside of work, Oliver is a father to 4yo twins, he’s a plant based athlete who trains a lot, and possibly too much. He’s currently training for an Ironman, ultramarathon and does lots of yoga and meditations to keep his body and mind in alignment. 

Oh, and Oliver also grew up in a Circus