Outsider Inc.
Podcast Description
Outsider Inc. is dedicated to visionary leaders breaking the mold of tech entrepreneurship. Hosted by Ian Hathaway—co-author of The Startup Community Way: Evolving an Entrepreneurial Ecosystem and co-founder of seed-stage venture capital firm FOVC—each episode delivers exclusive interviews and insider insights from exceptional founders building generation-defining companies. Join us for an in-depth exploration into the real-life stories of entrepreneurs from unexpected places and backgrounds who overcame early setbacks, built resilient teams without following the traditional Silicon Valley playbook, and created thriving ecosystems in overlooked markets. Whether you’re a first-time founder, seasoned innovator, or investor, you’ll gain actionable strategies, unconventional wisdom, and practical takeaways to help you navigate your entrepreneurial journey—no matter where you come from. Join our community today by subscribing on your favorite podcast app and dive even deeper on our newsletter at outsiderinc.substack.com.
Podcast Insights
Content Themes
The podcast centers around themes of entrepreneurship, resilience, and community impact, featuring guests from diverse backgrounds who have built successful companies outside traditional tech hubs. Episodes include discussions on building businesses amid economic challenges, fostering local talent, and creating supportive ecosystems, such as the inaugural episode with Scott Dorsey discussing the founding of ExactTarget and its implications for the Indianapolis tech landscape.
Outsider Inc. is dedicated to visionary leaders breaking the mold of tech entrepreneurship. Hosted by Ian Hathaway—co-author of The Startup Community Way: Evolving an Entrepreneurial Ecosystem and co-founder of seed-stage venture capital firm FOVC—each episode delivers exclusive interviews and insider insights from exceptional founders building generation-defining companies. Join us for an in-depth exploration into the real-life stories of entrepreneurs from unexpected places and backgrounds who overcame early setbacks, built resilient teams without following the traditional Silicon Valley playbook, and created thriving ecosystems in overlooked markets. Whether you’re a first-time founder, seasoned innovator, or investor, you’ll gain actionable strategies, unconventional wisdom, and practical takeaways to help you navigate your entrepreneurial journey—no matter where you come from. Join our community today by subscribing on your favorite podcast app and dive even deeper on our newsletter at outsiderinc.substack.com.
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
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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