In this episode of Outsider Inc., host Ian Hathaway interviews Isaac Saldana, the co-founder and former CEO of SendGrid, and current CEO of Joy Labs. Isaac discusses the interplay of humility and confidence in leadership and shares his unconventional path to success. From being a non-English-speaking teenager who managed a family and two jobs at 19, to raising significant capital and guiding SendGrid to an IPO and a $2 billion acquisition by Twilio, Isaac reflects on the pivotal moments and decisions that shaped his career. He highlights the importance of grit, mentorship, and a values-driven approach to leadership. Isaac also touches on his current venture, Laneful, and the future of email communication infrastructure powered by AI.

Show Notes:

(10:42) The Entrepreneurial Spark: Rich Dad, Poor Dad

(14:21) The Birth of SendGrid: Solving Email Deliverability

(19:21) Navigating Early Success and Challenges

(23:33) A Pivotal Decision: Replacing Himself as CEO

(27:10) Scaling SendGrid to IPO

(30:41) Post-SendGrid: The Birth of Joy Labs

(32:40) Lane Four: Revolutionizing Email with AI

(35:34) Leadership and Values in Entrepreneurship

(42:42) Balancing Family and Ambition

(47:20) Beyond the Bio with Isaac Saldana

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guest: Isaac Saldana, Co-Founder & fmr CEO of SendGrid

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

From Introvert to IPO: Culture, Control, and Building SendGrid into a Category Leader w/ Isaac Saldana, Co-Founder & fmr CEO, SendGrid