Outsider Inc.

Shegun Otulana, co-founder and CEO of TheraNest, shares his remarkable journey from Lagos to Alabama. He discusses the challenges and triumphs of bootstrapping a consulting firm and scaling TheraNest into a leader in mental health software. Shegun emphasizes innovative pricing strategies and the importance of building a remote-first culture. He also introduces Harmony Venture Labs, aimed at nurturing Birmingham's startup ecosystem, while reflecting on the influence of faith and family in his entrepreneurial path.

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 reflects on the lessons of skateboarding, the art of abating risk, and why sharing the stoke matters more than chasing hype. Dug also dives into his post-exit mission: fueling Michigan’s startup flywheel and building community wealth through the Song Foundation.   Show Notes:   (02:31) Dug Song's Early Life and Skateboarding Passion (06:09) Dug's Introduction to Computers and Early Tech Experiences (08:34) The w00w00 Collective and Early Hacking Days (15:04) Founding Duo Security: The Vision and Challenges (21:30) Scaling Duo Security: Success Factors and Michigan's Role (33:41) Building Community and Cultivating Talent (35:36) Song Foundation's Mission and Vision (40:16) Advice for Aspiring Entrepreneurs (43:29) Beyond the Bio with Dug Song   ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Dug Song, Co-Founder & former CEO, Duo Security   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 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 mentorship in startup ecosystems, sharing insights from the foundation of Techstars and its impact on global entrepreneurship. They also delve into personal challenges, including mental health and maintaining work-life balance, highlighting Feld’s open approach to discussing his own struggles and lessons learned.   Show Notes:   (03:52) The Origin of 'They Can't Kill You and They Can't Eat You' (08:22) The Power of Mentorship (15:24) Give First Philosophy (24:44) Writing 'Give First' (32:51) Brad's Move to Boulder (39:16) VC Transparency and Frustrations (42:36) The Blogging Journey (55:49) Mental Health and Entrepreneurship (01:02:40) Intentional Relationships and Personal Life (01:06:50) Beyond the Bio with Brad Feld     ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Brad Feld - Co-Founder of Foundry & 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.

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.

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.

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.