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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🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics.

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

YouTube: https://www.youtube.com/@ThisWontLastpodcast

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

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Turpentine VC: Delve deep into the art and science of building successful venture firms through conversations with the world’s best investors and operators. Subscribe wherever you get your podcasts: https://link.chtbl.com/TurpentineVC