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.

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.