How to Be More Transparent in Hindsight

CNN's John Sutter challenges CEOs to be more transparent in hindsight. He asks, do you really know if in hindsight, you should have been more transparent? "I think that the genuine answer is yes, but I don't know exactly when, how, where I would have done it," he says.

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Ryan Caldbeck is a tech founder, investor, and former CEO of CircleUp, which raised over $50M in venture capital during his tenure. Ryan is especially well known for his personal writings in the form of thought-provoking twitter threads where he chronicles his struggles with mental health, extreme leadership pressures, and sheds light on conflicts with investors. We dive into all this and more, including his experiences replacing himself as CEO while battling cancer.

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In The Arena is a part of the Turpentine podcast network. Learn more: www.turpentine.co

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TIMESTAMPS:

(01:00) Episode Preview

(04:00) The inflection point when Ryan decided to pivot

(08:59) “Terrifying growth”

(11:35) Vulnerability with the board vs vulnerability with the executive team

(16:00) How transparent should a leader be?

(20:50) Ryan’s hindsight about vulnerability

(26:55) 2019: Ryan starts to post publicly on Twitter

(28:25) How to deal with feeling bad about yourself