In this episode of Outsider Inc., host Ian Hathaway interviews Kyle Porter, founder and longtime CEO of SalesLoft. Kyle shares his remarkable journey from nearly failing in the first year of SalesLoft to scaling the company to unicorn status with a $2.3 billion valuation. He discusses the core principles of leadership, such as leading with love, staying mission-driven, and valuing corporate culture. Kyle also reveals personal challenges, including childhood health issues and a transformative college experience, and how these shaped his entrepreneurial path. Finally, Kyle talks about his current life on a tangerine farm and supporting his wife's business endeavors, emphasizing the importance of family and personal fulfillment.

Show Notes:

(02:12) Leading with Love: A CEO's Perspective

(02:55) Kyle's College Turning Point

(04:55) Childhood Hustles: The Seeds of Sales Passion

(06:52) Overcoming Childhood Health Challenges

(12:57) Early Professional Experiences and Lessons Learned

(15:51) The Birth and Rebirth of SalesLoft

(26:49) Navigating the Pandemic: Challenges and Growth

(30:41) Life Changes During the Pandemic

(31:31) The Vista Equity Acquisition

(34:31) Transitioning from CEO to Executive Chairman

(37:16) Supporting Each Other's Dreams

(44:04) Building SalesLoft in Atlanta

(51:08) Beyond the Bio with Kyle Porter

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

✅ Guest: Kyle Porter, Founder & fmr CEO of SendGrid

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.

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