124: Jon Evans: How to Thrive When the Odds Are Against You

The Courageous Leaders Club

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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