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.
Episodes
In this episode of Outsider Inc., host Ian Hathaway speaks with Shegun Otulana, co-founder and CEO of TheraNest and Harmony Venture Labs. Shegun shares his journey from arriving in Alabama from Lagos, Nigeria at 18, to bootstrapping his first consulting firm, and eventually scaling TheraNest into a national leader in mental health software. The conversation c...
In this episode of Outsider Inc., host Ian Hathaway interviews Dug Song, co-founder of Duo Security, which sold to Cisco for $2.35B in 2018. Dug shares his unconventional journey from latchkey kid and hacker to leading one of Michigan’s biggest tech exits — and building a culture-first cybersecurity company grounded in empathy, usability, and trust. He reflec...
In this episode of Outsider Inc., host Ian Hathaway interviews Brad Feld, a prominent figure in venture capital and entrepreneurship. The conversation explores Feld's 'Give First' philosophy, which centers on helping others without expecting immediate returns, thereby fostering stronger communities and relationships. Feld discusses the importance of mentorshi...
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 commer...
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 throug...
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 globa...
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. H...
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 probl...
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 laun...
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...
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