Chris Simon - From InLoop and LanternPay to NAB acquisition and Dev Cycles

My personal journey in leadership and startups.


This episode’s guest is Chris Simon. Chris is the technical co-founder of, home of Australian Fintech success stories and (Recently acquired by NAB).

Since 2021 he has been coaching startup CTOs through Dev Cycles Technology Advisory ( as well as supporting executives & boards with strategic technology advice, and engineering teams with training, mentoring and consulting.

In this episode Chris shares:

  • The hard shift leaders encounter when they never intended to become a leader
  • How leadership skills can be learnt in the most surprising places
  • The challenge of realising there is an inherent power dynamic when building trust with employees
  • How not giving employees enough direction because you want to respect them can lead to disaster
  • Learning that you may make the same mistake multiple times
  • How he deals with how his own frustrations can cause tension in the team

Key Quotes

“Be directive without being a dictator and be assertive without being an arse.”

“If you’ve not given them clarity on what’s expected then that’s not fair.”

“If something is not going right (with the team) I start by looking at what have I done?”

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