Crazy Wisdom

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: https://bit.ly/2O7vhmY 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 Please subscribe to Crazy Wisdom wherever you listen to podcasts, and leave us a rating and review in Apple Podcasts.      

Show Notes

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: https://bit.ly/2O7vhmY

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

Please subscribe to Crazy Wisdom wherever you listen to podcasts, and leave us a rating and review in Apple Podcasts.

 

 

 

What is Crazy Wisdom?

In his series "Crazy Wisdom," Stewart Alsop explores cutting-edge topics, particularly in the realm of technology, such as Urbit and artificial intelligence. Alsop embarks on a quest for meaning, engaging with others to expand his own understanding of reality and that of his audience. The topics covered in "Crazy Wisdom" are diverse, ranging from emerging technologies to spirituality, philosophy, and general life experiences. Alsop's unique approach aims to make connections between seemingly unrelated subjects, tying together ideas in unconventional ways.