Outsider Inc.

In this episode of Outsider Inc., host Ian Hathaway interviews Guillaume de Zwirek, founder and CEO of Artera. Guillaume's journey from a classical guitarist and world-class Ironman triathlete to a successful health tech entrepreneur is anything but conventional. Inspired by his personal frustrations as a healthcare patient, Gui founded Artera, a platform that unifies patient communication. Through his story of quitting a comfortable job, securing funds from friends, and unwavering determination, Gui illustrates the concept of 'burning the ships' with no retreat. The interview delves into his experiences at Google and data platform Graphiq, the decision to move Artera to Santa Barbara, and the challenges faced during the COVID-19 pandemic. Gui also shares his views on leadership, the impact of AI on healthcare, and future goals for Artera.    Show Notes:   (02:20) From Ironman to Healthcare Innovator (06:40) Early Life and Entrepreneurial Spirit (11:28) The Google Experience (16:23) Joining Graphic and the Santa Barbara Move (28:15) Choosing the Right Business Partners (29:50) The Joy of Building and Learning (30:37) A Bold Move to Santa Barbara (35:43) Embracing AI and Future Challenges (40:32) Leadership and Personal Growth (48:10) Final Reflections and Advice (49:30 Beyond the Bio with Guillaume de Zwirek   ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Guillaume de Zwirek, Founder & CEO, Artera   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.

Jon Lensing, co-founder and CEO of OpenLoop, talks about transforming healthcare access through telehealth from Iowa. He shares his unconventional journey from aspiring surgeon to startup founder, highlighting the scrappy beginnings of OpenLoop in a grocery café. The discussion dives into how capital constraints fostered creativity and efficiency, the challenges of a late-term sheet reversal, and lessons learned about investor alignment. Jon emphasizes the importance of mentorship in building local ecosystems and encourages aspiring founders to take action on their ideas.

In this episode of Outsider Inc., host Ian Hathaway speaks with Jimena Pardo, co-founder of Carrot, Mexico’s first car-sharing platform, and now Co-Founder & Managing Partner at Hi Ventures. Jimena opens up about the rollercoaster of building Carrot, the lessons of operating in a tough market, and how she transitioned from founder to investor. She shares candid reflections on founder identity, resilience after burnout, and her vision for Latin America as a launchpad for globally recognized startups. From raising capital in an emerging market to shaping Hi Ventures into a firm that champions bold, outsider entrepreneurs, Jimena’s journey is a masterclass in grit, adaptation, and long-term vision.   Show Notes:   (03:18) Early ambitions, education, and what drew Jimena into entrepreneurship (07:42) Founding Carrot and tackling mobility challenges in Mexico (15:33) Lessons from scaling Carrot and navigating the exit (22:06) The personal toll of entrepreneurship and founder burnout (29:47) Transitioning from founder to investor and joining Meta (36:21) The importance of founder identity beyond the startup (43:18) Launching Hi Ventures and its mission to back bold entrepreneurs (52:04) Breaking capital barriers in Latin America and building global companies (1:01:19) Why transparency, humility, and mentorship matter in entrepreneurship (1:09:33) Jimena’s vision for the next generation of founders in Latin America (1:16:55) Beyond the Bio with Jimena Pardo   ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Jimena Pardo, Co-Founder of Carrot & Co-Founder and Managing Parter at Hi Ventures 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 chats with Melodie van der Baan, co-founder and CEO of Max Retail. Melodie shares her unconventional journey from skipping college to diving into real estate, losing everything in the housing crash, and then transforming into a mobile designer clothes distributor. Her challenges and experiences eventually led her to start Max Retail, a platform for converting unsold inventory into revenue, which now serves over 2,000 retailers across the U.S. The discussion highlights her perseverance, customer focus, and innovative approach to the retail industry.   Show Notes:   (02:41) Skipping college and diving into real estate as a teen (05:22) Losing everything in the housing crash (08:14) Life on the road: selling designer clothes from a Sprinter van (12:49) Launching a retail shop and confronting the inventory problem (18:56) Starting Max Retail during the pandemic (25:03) Breaking into Techstars after multiple attempts (32:17) Scaling to 2,000+ retailers and raising $20M+ (41:09) Lessons on persistence, resilience, and customer focus (47:56) Beyond the Bio with Melodie van der Baan   ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Melodie van der Baan, Co-Founder & CEO of Max Retail   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 Jewel Burke Solomon, a founder, investor, and community leader based in Atlanta. Jewel shares her experiences of co-founding PartPic, a startup designed to identify and replace industrial parts through visual search technology, which was later acquired by Amazon. She discusses her challenges in raising capital as a black female founder and how those experiences inspired her to become an investor. Jewel highlights her work at Google for Startups, where she helped launch the Black Founders Fund and Latino Founders Fund. She also talks about co-founding Collab Capital, a venture fund focused on building long-term wealth and trust in underserved communities. This is a story of turning hard-earned lessons into purposeful action and reimagining who gets backed in venture.   Show Notes:   (01:17) Jewel’s Journey with PartPic (06:27) Navigating Identity and Overcoming Bias (10:16) Early Influences and Entrepreneurial Roots (15:00) From Google to McMaster Car (20:25) The Birth of PartPic (27:28) The Decision to Sell to Amazon (30:26) Handling Post-Sale Depression (36:55) Founding Collab Capital (38:37) The Atlanta Startup Ecosystem (40:23) Mental Health Initiatives at Collab (42:10) Reflections on DEI and Future Goals (48:15) Beyond the Bio with Jewel Burks Solomon   ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Jewel Burks Solomon, Co-Founder of Partpic & Managing Partner, Collab 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.

This episode of Outsider Inc. features Sean O’Sullivan, Co-Founder of MapInfo & Managing General Partner of SOSV. Host Ian Hathaway leads the conversation with the digital mapping pioneer, deep tech investor, and humanitarian, as he shares his extraordinary journey from co-founding MapInfo, a revolutionary digital street mapping system, to his role in creating the term 'cloud computing' with Net Centric and beyond. Sean's path includes a stint as a freelance war journalist in Iraq and the founding of Jumpstart International, a humanitarian organization. He later launched SOSV, the most active deep tech venture capital firm focusing on climate and human health. The discussion covers the importance of mission-oriented leadership, resilience, reinvention, and the significance of purpose in driving meaningful impact.    Show Notes:   (03:26) Early Life and Resilience (07:58) The Birth of MapInfo (15:01) NetCentric: Pioneering Cloud Computing (23:15) From Tech to Humanitarianism in Iraq (27:11) Tragic Losses and Leadership Lessons on Purpose and Service (32:32) Transitioning Back to Tech and Investment (40:07) Building a Global Startup Ecosystem (42:51) Beyond the Bio with Sean O’Sullivan   ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Sean O’Sullivan, Co-Founder of MapInfo & Managing General Partner of SOSV   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.

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.