Outsider Inc.

In a fascinating conversation, Jason Seats, Co-Founder of Slicehost and former CIO of Techstars, shares his entrepreneurial journey and the essence of simplicity in product design. He reflects on the unexpected acquisition by Rackspace and the challenges of integrating into a larger company. Jason emphasizes the importance of trust and partnership in startups, and the shift in the venture capital landscape over time. His insights into mentoring the next generation of entrepreneurs highlight the value of community and resilience in their journeys.

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

In this episode of Outsider Inc., host Ian Hathaway sits down with Wade Foster, co-founder and CEO of Zapier, an automation platform valued at $5 billion. Wade discusses his unique path to success, starting from a typical middle-class environment in Missouri, leveraging lessons from early marketing roles, and winning a local hackathon with his initial idea. He shares insights into his journey through Y Combinator, the intentional choices behind Zapier's remote workforce, the importance of solving urgent problems, and a cautious approach to raising capital. Wade’s story offers powerful takeaways on resilience, staying focused, and holding tight to your values—especially when building a culture for a remote workforce.   Show Notes:   (02:07) Wade's Early Career and Startup Experience (07:00) The Birth of Zapier (11:32) Early Challenges and Breakthroughs (16:27) Joining Y Combinator (23:04) Building a Remote Workforce (28:03) Building Team Comradery Remotely (30:00) Principles for Hiring in a Remote Setup (32:08) Zapier's Unique Approach to Funding (37:02) Advice for Early-Stage Founders (42:23) Reflections on Silicon Valley and Outsider Geographies (44:58) Beyond the Bio: Personal Insights   ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Wade Foster - Co-Founder & CEO, Zapier 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.

In this episode of Outsider Inc., host Ian Hathaway interviews Michael Prager, co-founder and CEO of AvidXchange. Michael shares his entrepreneurial journey from founding early ventures to building AvidXchange into a leader in FinTech, processing $200 billion in annual payments. He discusses the importance of starting small, focusing on solving specific problems, and the evolution of AvidXchange's business model. Additionally, Michael highlights the advantages of building a tech company in Charlotte, North Carolina, and his commitment to bridging the digital divide through the AvidXchange Foundation. The conversation emphasizes practical advice for entrepreneurs, the importance of evolving leadership to match company growth, and the substantial impact AvidXchange has had on the Charlotte tech ecosystem.   Show Notes:   (02:53) Michael's Early Ventures and Entrepreneurial Lessons (05:36) The Birth of AvidXchange (06:32) Scaling AvidXchange: From Startup to Public Company (12:20) Challenges and Lessons in Building a Tech Company (20:18) The Evolution of the Avid Pay Network (24:27) Raising Capital and Partnering with Bain (26:58) The IPO Journey and Reflections (28:48) Building a Tech Company in Charlotte (34:05) Leadership and Personal Growth (38:22) The Impact of AvidXchange on Charlotte (40:20) Beyond the Bio: Personal Insights and Advice   ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Michael Praeger - Co-Founder, Chairman & CEO, AvidXchange   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.

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.

Introducing Outsider Inc., the podcast that dives into the untold stories of visionary leaders from unexpected places and backgrounds who broke the mold of tech entrepreneurship to build generation-defining companies. In each episode, host Ian Hathaway facilitates a conversation that reveals how founders turned early setbacks into stepping stones, built resilient teams without a prototypical playbook, and transformed entire communities that today produce a lasting impact.  Get a preview of what’s ahead with highlights from guests like: ✅ Scott Dorsey – His $2.5 billion acquisition of ExactTarget by Salesforce helped birth a thriving tech ecosystem in Indianapolis ✅ Linda Rottenberg – Her non-profit, Endeavor, supports entrepreneurs in over 40 countries worldwide, transforming emerging markets into dynamic startup ecosystems ✅ Wade Foster – Co-founded Zapier, which was hatched in a Central Missouri hackathon and scaled to a more than $5 billion valuation through a fully remote and capital-efficient approach ✅ Michael Praeger – Left Boston to launch and scale AvidXchange, a B2B payments fintech in Charlotte, to a more than $5 billion valuation at IPO ✅ Jason Seats – Bootstrapped an influential startup to an improbable exit from a small office in St Louis before overseeing the investment in thousands of companies as CIO of Techstars Subscribe now and join us as we prove that great entrepreneurs can come from anywhere. Listen wherever you get your podcasts or at outsiderinc.substack.com.