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

Read Ryan's Medium post: https://rb.gy/zep70h

Check out CircleUp: https://circleup.com

FOLLOW Ryan: https://twitter.com/ryan_caldbeck

FOLLOW Jason: https://linktr.ee/calacanis

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Show notes:

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 at https://mainstreet.us/twist

12:33 Filling the supply & demand side of their consumer goods fundraising marketplace

21:56 Squarespace - Go to https://squarespace.com/twist 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 at https://odoo.com/twist

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

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