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

RECOMMENDED PODCAST:

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

Catch up on host Jesse Genet’s own crucible moments in her entrepreneurial story in Episode 6:

Spotify: https://open.spotify.com/episode/3HQKu4vbaIuAvhgKLBuyYk?si=UYb2aGlJTxynO_B8UzMkUQ

Apple: https://podcasts.apple.com/us/podcast/e6-host-jesse-genet-on-selling-her-startup-lumi-while/id1691530886?i=1000622369978

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

(37:30) A real leader never quits

(42:33) Dark side of VC

(46:00) Ryan's feedback email to one of his investors

LINKS REFERENCED:

Ryan Caldbeck's writing https://ryancaldbeck.co/

Ryan Caldbeck's Pivoting CircleUp thread: https://twitter.com/ryan_caldbeck/status/1118288136918847488?lang=en

Hard Things About Hard Things: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205/ref=tmm_hrd_swatch_0?_encoding=UTF8&qid=1690962629&sr=1-1

X: 

@ryan_caldbeck (Ryan)

@jessegenet (Jesse)

@eriktorenberg (Erik)

@inthearena_pod