54 min
E7: Ryan Caldbeck on “Terrifying Growth”, Managing Mental Heath, and Radical Sharing "In The Arena"
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- Entrepreneurship
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.
RECOMMENDED PODCAST:
The HR industry is at a crossroads. What will it take to construct the next generation of incredible businesses – and where can people leaders have the most business impact? Hosts Nolan Church and Kelli Dragovich have been through it all, the highs and the lows – IPOs, layoffs, executive turnover, board meetings, culture changes, and more. With a lineup of industry vets and experts, Nolan and Kelli break down the nitty-gritty details, trade offs, and dynamics of constructing high performing companies. Through unfiltered conversations that can only happen between seasoned practitioners, Kelli and Nolan dive deep into the kind of leadership-level strategy that often happens behind closed doors. Check out the first episode with the architect of Netflix’s culture deck Patty McCord.
https://link.chtbl.com/hrheretics
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
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.
RECOMMENDED PODCAST:
The HR industry is at a crossroads. What will it take to construct the next generation of incredible businesses – and where can people leaders have the most business impact? Hosts Nolan Church and Kelli Dragovich have been through it all, the highs and the lows – IPOs, layoffs, executive turnover, board meetings, culture changes, and more. With a lineup of industry vets and experts, Nolan and Kelli break down the nitty-gritty details, trade offs, and dynamics of constructing high performing companies. Through unfiltered conversations that can only happen between seasoned practitioners, Kelli and Nolan dive deep into the kind of leadership-level strategy that often happens behind closed doors. Check out the first episode with the architect of Netflix’s culture deck Patty McCord.
https://link.chtbl.com/hrheretics
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
54 min