Jon Evans, Chief Customer Officer at System1 and Host of The Uncensored CMO podcast, shares how failure has led to his biggest successes and how being tasked with doing something that was never done before was one of the most frightening things in his life.

We Cover:

05:05 – The lonely and risky leap into entrepreneurship

06:55 – How Adam Morgan’s book "Eat Big Fish" helped Jon embrace challenges

11:13 – Turning failures into the biggest career breakthroughs

12:56 – Battling corporate focus on Image vs. Reality

16:14 – Thriving under pressure: How confidence grows from failure

20:53 – Making hard decisions

22:36 – The challenge of saying no and asking for help

28:36 – Why VCs value failure as part of feeling confident to invest in you

29:48 – The importance of bouncing back from failure

34:32 – Navigating uncertainty and constant pressure in freelance work

35:36 – How building a CMO network led to a full-time role

40:51 – How success exposes you to criticism and negativity

44:47 – Supporting senior marketing executives through isolation

48:11 – Jon’s biggest regret: Why you should pursue your goals earlier

52:11 – How trust alone can lead to six-figure investments

54:22 – Building relationships that pay off, like compound interest

56:23 – The support system that ensures consistent success

Don’t miss out on this thought-provoking episode.

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On Target: What Am I Supposed To Do With My Life?