CircleUp's Ryan Caldbeck on stepping down as CEO, mental & physical toll of being a founder | E1141

In this episode, Jason Calacanis chats with Ryan Caldbeck about CircleUp, the consumer goods fundraising marketplace. They discuss CircleUp's evolution, from a marketplace to a fund-raising Series C company, and Caldbeck's decision to step down as CEO due to health struggles. The episode also touches on the importance of addressing founder mental health.

Speakers

AI Chat

Unidentified

Jason Calacanis

Host • 52%

Ryan Caldbeck

Guest • 45%

Unidentified

Partners

Chapters

0:00	Start
1:03	Jason intros Ryan Caldbeck & addresses the infamous board member email
6:18	What is CircleUp? Plus their incredible cap table & perfect timing
11:04	MainStreet - Startups: you’re owed over $50,000 by the IRS, get it back
12:33	Filling the supply & demand side of their consumer goods fundraising marketplace
21:56	Squarespace - Go to for a free trial, and use code TWIST for 10% off
23:29	Why the quality of companies did not correlate with their ability to fundraise, how Halo Top ice cream confused investors
27:21	Pivoting from a marketplace to raising a fund as a Series C company
31:34	Early issues with syndicates: lack of diversification, how CircleUp was able to classify consumer goods companies accurately
35:30	Odoo - Get your first app free & $1000 off your first implementation pack
36:59	Why Ryan stepped down as CEO - mental & physical health struggles, difficulty of pivoting a post-Series C company
48:29	Detailing his struggles to help founders feel less lonely
51:50	Ryan's advice: Early-stage firms & business schools should talk about founder mental health
56:17	How consumer goods founders can contact CircleUp

Transcript

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