Jamie Pride – A Survivor’s Guide To Being An Entrepreneur

This is the episode every entrepreneur needs to hear. Jamie Pride, the former CEO of RealEstate.com.au, author and founder of 6 tech start-ups, most notably ‘REFIND’, once a listed $200m business that came crashing down, gives his guide to founder-fitness. This is both a personal story of triumph and a tactical playbook for a longer happier career as an entrepreneur. 

Jamie Pride

What I Learned

  • Entrepreneurs, particularly in Australia, are burning out and becoming depressed because:
    • Entrepreneurs self-identify with their business. They sacrifice so much of themselves for the business that when the business is a success, they feel like a success, and when the business is a failure, they feel like a failure. There’s too much linkage between self-worth and business outcome.
    • In Australia, there’s a stigma around failing, unlike in the US where it’s a right of passage.
    • Entrepreneurs are surrounded by curated social media where everybody is ‘crushing it’ – so when they do fail, they feel like the only ones failing.
  • How to build longevity as an entrepreneur:
    • Reframe your thinking about your business and career from a sprint to a marathon. You need to build for sustainability.
    • Don’t think about your business as your only shot and that it has to be a success.
    • Make sure your business is aligned to your values and your purpose. The purpose is more sustainable than passion, especially when the chips are down in tough periods, it’ll make you more willing to weather the storm.
    • Build capacity – and then build a business on top of that.
      • Physical capacity: if you’re not well, you won’t be able to deal with the stress
      • Mental capacity: your ability to manage your day, your productivity habits and how long you can hold your attention for
      • Emotional capacity: how do you create headspace? How well do you question your bias, beliefs & bullshit?
    • Once a founder has focused on the three areas of capacity, they typically exhibit these three key traits which contribute to a better founder and an improved chance of success:
      • They become more self-aware: which makes them more investible, more coachable and they can build better relationships
      • They’re going to be more adaptable: able to change with the different conditions and circumstances
      • They’re going to be more resistant: they’ll have the ability to get back up and get back up faster.
    • The goal should be to enjoy what you do every day – rather than constantly looking to escape. Escapism is a burnout effect that many corporate executives and entrepreneurs face. Working in stints of time with a view to ‘take a break’ in the horizon. If you’re enjoying what you’re doing, and you feel nourished by it – there’s no need to seek the escape from it.
    • To implement these foundations you need rituals and routines. For example, what you do in the morning will set the routine for the rest of your day (tip: set a digital sunrise – no email or social until 2hrs after you wake up).
  • The three most common issues founder seek help with are co-founder relationships, investor relationships and managing team relationships.
  • The real fear for entrepreneurs is not the failure or losing money, it’s disappointing other people, especially people who made sacrifices for them. It’s important to have open conversations with these people from the beginning, especially your family – because you can’t succeed if your fighting about your business at home.
  • All good entrepreneurs have three core characteristics; empathy, curiosity and dissatisfaction.

Show Notes


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