Outsider Inc.

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.

Bootstrapping to Exit, First Principles Thinking, Product Simplicity, and Mentoring the Next Generation w/ Jason Seats, Co-Founder of Slicehost & fmr CIO of Techstars 05/14/2025

Bootstrapping to Exit, First Principles Thinking, Product Simplicity, and Mentoring the Next Generation w/ Jason Seats, Co-Founder of Slicehost & fmr CIO of Techstars On this episode of Outsider Inc., host Ian Hathaway sits down with Jason Seats, Co-Founder of Slicehost, former Chief Investment Officer of Techstars, and a pioneer in the startup and cloud computing worlds. Jason details his journey from co-founding the game-changing cloud infrastructure company, Slicehost, to mentoring and investing in early-stage startups through Techstars. They discuss the importance of simplicity, first principles, and the value of building with trusted partners. Jason shares insights on navigating acquisitions, the challenges of integrating into a large company, and the evolution of the pre-seed and seed investment landscape. His story is a testament to succeeding as an outsider and the power of trusting relationships in entrepreneurship. Show Notes: (02:12) The Birth of Slicehost: Simplicity and Innovationt (06:32) The Importance of Partnership and Family Support (10:40) Navigating Early Challenges and Learning from First Principles (13:55) Scaling Up: Hiring and Community Building (18:31) Unexpected Acquisition: The Rackspace Story (24:50) Transition to Rackspace: New Beginnings in San Antonio (28:29) Transition to Techstars Cloud (32:25) Launching Techstars in San Antonio (35:47) Evaluating Startups and Investments (41:58) Macro View on Venture Capital (49:37) Life After Techstars (51:03) Beyond the Bio with Jason Seats ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Jason Seats - Co-Founder of Slicehost & former Chief Investment Officer of Techstars 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. /episode/index/show/1e88975b-f4a9-4d81-89e0-79dc357ed517/id/36556345

Disrupting the Status Quo & Building Global Entrepreneurial Ecosystems w/ Linda Rottenberg, Co-Founder & CEO, Endeavor 04/30/2025

Disrupting the Status Quo & Building Global Entrepreneurial Ecosystems w/ Linda Rottenberg, Co-Founder & CEO, Endeavor On this episode of Outsider Inc., host Ian Hathaway interviews Linda Rottenberg, co-founder and CEO of Endeavor, the global organization supporting high-impact entrepreneurs in emerging markets. Linda shares her unique insights on the benefits of chaos over stability for entrepreneurship, her journey from an unlikely start in Latin America to creating a global network that has redefined entrepreneurship in over 45 countries, and the impact of fostering local role models and ecosystems. They discuss key success stories, the rise of unicorns from unexpected places, and the vital role of mentorship and reinvestment in sustaining entrepreneurial ecosystems. Linda also opens up about her personal journey, navigating male-dominated industries, and balancing professional and personal life. The episode wraps up with Linda’s bold predictions for the next 30 years of global entrepreneurship and her vision for Endeavor's future. Show Notes: (00:41) Introducing Linda Rottenberg: The Unstoppable Force (04:25) Linda's Journey: From Harvard to Latin America (06:59) The Birth of Endeavor: A Vision for Global Entrepreneurship (10:04) Early Success Stories: Building Role Models (21:00) The Multiplier Effect: Creating Sustainable Ecosystems (27:32) Global Innovations: Outsiders Becoming Pioneers (36:59) Balancing Personal and Professional Life (40:18) Advice for Aspiring Entrepreneurs (44:16) Future Vision for Endeavor (48:38) Beyond The Bio with Linda Rottenberg ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Linda Rottenberg - Co-Founder & CEO, Endeavor 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 /episode/index/show/1e88975b-f4a9-4d81-89e0-79dc357ed517/id/36364425

From Central Missouri Hackathon to $5B Automation Platform w/ Wade Foster, Co-Founder & CEO, Zapier 04/16/2025

From Startup to IPO: Building a FinTech Giant in Charlotte w/ Michael Praeger, Co-Founder, Chairman & CEO, AvidXchange 04/02/2025

Scaling Companies & Leveraging Community in Indianapolis w/ Scott Dorsey, Co-Founder & CEO, ExactTarget; Managing Partner, High Alpha 03/19/2025

Scaling Companies & Leveraging Community in Indianapolis w/ Scott Dorsey, Co-Founder & CEO, ExactTarget; Managing Partner, High Alpha On this inaugural episode of Outsider Inc., host Ian Hathaway talks with Scott Dorsey, co-founder and former CEO of ExactTarget. Scott shares his journey from founding ExactTarget in 2000, through its $2.5 billion acquisition by Salesforce in 2013, to his current efforts in fostering entrepreneurship in Indianapolis via HighAlpha. Their discussion covers launching a company when the dot com bubble burst, early sales and fundraising strategies, and ExactTarget's transformative impact on Indianapolis' tech ecosystem. Scott emphasizes his philosophy of building a company and a community, revealing how leveraging local talent and fostering a strong company culture contributed to ExactTarget's success. He also discusses the importance of supportive ecosystems for tech startups and his continued mission to invest in and support local entrepreneurs. Show Notes: (03:15) Scott Dorsey's Early Career and ExactTarget's Founding (05:30) Challenges and Early Successes of ExactTarget (11:44) Raising Capital and Building a Sales Team (18:35) Transitioning to Enterprise and Securing Venture Capital (24:03) Navigating IPOs and Acquisition by Salesforce (30:23) Founding High Alpha: A New Venture Studio (32:19) High Alpha's Unique Approach and Methodology (36:06) Building a Tech Ecosystem in Indianapolis (41:49) The Orange Culture and Its Lasting Impact (47:16) Personal Insights and Leadership Philosophy (51:12) Beyond the Bio w/Scott Dorsey ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Scott Dorsey - Co-Founder & CEO, ExactTarget; Managing Partner, High Alpha 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. /episode/index/show/1e88975b-f4a9-4d81-89e0-79dc357ed517/id/35748220

Outsider Inc. Trailer 03/07/2025

Outsider Inc.

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