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 Kevin O’Connor, co-founder of DoubleClick, former CEO of Graphiq, and Founder and General Partner at ScOp Venture Capital. Kevin shares insights from his remarkable career, starting from his early curiosity in electronics to forego a career as a research scientist and instead spearhead the commercial internet. He discusses the meteoric rise of DoubleClick, the birth of Silicon Alley, and his transition into startup investing and mentoring. Kevin also delves into his experience with Graphiq, his views on entrepreneurial resilience, and his current focus on helping early-stage software companies scale. His journey highlights the importance of identifying early opportunities, cultivating non-traditional talent, and navigating the evolving tech landscape beyond traditional hubs
Show Notes:
(02:55) Kevin’s Early Life and First Venture
(06:12) The Birth of DoubleClick
(08:29) Navigating the Dot-Com Boom
(11:20) Challenges and Growth in New York
(18:09) The Dot-Com Bubble Burst
(23:02) The Legacy of DoubleClick in New York’s Tech Scene
(24:01) Moving to Santa Barbara: A New Chapter
(27:05) The Birth of Graphiq and the Knowledge Graph
(29:42) Selling to Amazon and Lessons Learned
(31:04) Investing in Non-Consensus Founders
(39:56) Beyond the Bio with Kevin O’Connor
✅ Host: Ian Hathway – Co-Founder & Managing Partner, FOVC
✅ Guest: Kevin O’Connor – Co-Founder of DoubleClick, fmr CEO of Graphiq, and Founder & General Partner at ScOp Venture Capital
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.
Disclaimer
This podcast’s information is provided for general reference and was obtained from publicly accessible sources. The Podcast Collaborative neither produces nor verifies the content, accuracy, or suitability of this podcast. Views and opinions belong solely to the podcast creators and guests.
For a complete disclaimer, please see our Full Disclaimer on the archive page. The Podcast Collaborative bears no responsibility for the podcast’s themes, language, or overall content. Listener discretion is advised. Read our Terms of Use and Privacy Policy for more details.