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Crazy Wisdom

Jul 22, 2019

Such a great, candid interview with down-to-earth Ryan Caldbeck, CEO of CircleUp, on some of the rarely-discussed, yet crucial aspects of entrepreneurship, its effects on mental health and how leaders can improve their lifestyle to boost their company's performance. Ryan was very open and receptive towards sharing some of the most intimate issues that he's faced on his journey as a founder. 

Check out Ryan's tweetstorm here:

Timeline of the conversation:

(3:18) - What is the #1 lesson that building CircleUp has taught Ryan?

(6:26) - What is the job of a CEO?

(8:35) - Ryan's spiritual backdrop

(11:43) - Ryan's advice for inexperienced entrepreneurs 

(15:49) - Distinguishing between what is Important, what is Urgent, or what is both

(23:30) - Business context: Work vs. Non-work

(26:20) - Why you should be wary of going to conferences

(28:15) - Ryan's experience with series-C investment

(34:22) - The role of authenticity in the grand scheme of business

(48:44) - Related reading and closing thoughts

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