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.

In this episode of Outsider Inc., host Ian Hathaway speaks with Jon Lensing, co-founder and CEO of OpenLoop, a telehealth infrastructure platform headquartered in Des Moines, Iowa. From growing up in rural Iowa to training as a surgeon, Jon's path took an unconventional turn when he left medicine to build a company addressing healthcare access. Since its founding in 2020, OpenLoop has scaled to more than 2 million patients annually, raised over $120 million, and reached unicorn status while staying rooted in Iowa. Jon shares how constraint breeds creativity, the scrappy early days writing letters to doctors in a grocery store café, and the near-collapse when a term sheet fell through the night before payroll. He also reflects on co-founder dynamics, the lessons of a major pandemic pivot, building a fire-eating culture, and why success stories in outsider places fuel the next generation of founders.

Show Notes:

(07:42) Medical school, entrepreneurial sparks, and building side businesses

(12:06) The decision to forgo residency and launch OpenLoop

(14:03) Scrappy early days: handwritten letters, Hy-Vee café, and Techstars Iowa

(18:00) Capital constraints, rejections, and why scarcity fueled efficiency

(20:01) Meeting co-founder Christian Williams and complementary dynamics

(22:16) Making a high-stakes pandemic pivot into telehealth infrastructure

(28:14) A pulled term sheet, payroll crisis, and lessons on choosing investors

(33:02) Building a "fire-eating" culture and hiring for high-output operators

(38:12) Why Jon chose to build in Iowa and the advantages of staying close to customers

(45:55) Beyond the Bio with Jon Lensing

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guest: Jon Lensing, Co-Founder & CEO, OpenLoop

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 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.

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 covers his unique approach to pricing, building a remote team, and the importance of eagerness and passion in serving customers. Shegun also discusses his transition from the CEO role, the creation of Harmony Venture Labs to support the next generation of entrepreneurs in Birmingham, and the influence of his faith and family in his career. Throughout, Shegun emphasizes the impact of creating intentionally and staying aligned with one's values.

Show Notes:

(05:09) Shegun's Transition to the US and Early Impressions

(08:28) Founding Zertis Technologies and the Entrepreneurial Drive

(11:26) Identifying the Right Problem and Market

(13:18) Building TheraNest and the Mental Health Focus

(18:45) Differentiation and Pricing Strategy

(21:59) Remote Work and Team Building

(26:06) The Challenges and Benefits of Being a One-Man Band

(29:50) The Founder Mentality: Building a Culture of High Performance

(33:30) Scaling Up: From TheraNest to Therapy Brands

(40:33) Transitioning Out: From CEO to Board Member

(43:26) Harmony Venture Labs: Building a System for Startups

(46:55) The Importance of Family and Partnership

(50:43) Faith and Leadership: Guiding Principles

(53:14) Beyond the Bio with Shegun Otulana

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guest: Shegun Otulana, Founder & CEO, TheraNest & Harmony Venture Labs

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 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.