Crazy Wisdom
Ryan Caldbeck - The Other Side of Entrepreneurship
- Money & Sovereignty
- Entrepreneurship & Startups
- entrepreneurship
- startup funding
- mental health
- leadership
- venture capital
- stress management
- series c pivot
About this episode
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
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Episode transcript
I think first and foremost, to kind of center on why you want to do it. I worry a lot that many, many people are looking to start companies because entrepreneurship is glorified, because they see slack going public today because of extrinsic rewards, and the journey is just flat out too hard for that.
Welcome to the Crazy Wisdom Podcast. My guest today was ryan Kaldbeck, the CEO of CircleUp. I reached out to Ryan because he wrote this amazing tweet, tweet storm, actually, about how stressful it was for him to pivot at the Series C stage. And he just kind of really provides so much value in this episode for founders who are struggling with stress and want to understand how to intelligently work with that stress in order to create what they want to create, you know, and you're doing this for a reason. And Ryan has a lot of valuable wisdom here to share. Really hope you enjoy it. I want to let you guys know about an online course I'm going to offer with anders Jones, the CEO of Facet wealth, who raised $40 million to start a financial services company in Baltimore and is now building a remote team based off of his initial success in taking on the financial services and really excited to offer this online course for you guys. Basically, it's going to be a live training where I interview, I interview Anders about how to raise a Series A and then build a remote team around it. So we're going to offer a lot of value as to how to raise money and also how to build a remote team. And what I love doing is extracting wisdom from people who are too busy to extract it themselves and providing it.
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