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.
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Dynamic Capitalism & Building Entrepreneurial Ecosystems Anywhere w/ Seth Levine, Co-Founder of Foundry
12/17/2025
Dynamic Capitalism & Building Entrepreneurial Ecosystems Anywhere w/ Seth Levine, Co-Founder of Foundry
In this episode of Outsider Inc., host Ian Hathaway sits down with Seth Levine, co-founder and longtime partner at Foundry, to explore a two-decade journey at the center of entrepreneurship, venture capital, and ecosystem building outside traditional power centers. Levine reflects on helping build Foundry into a top-tier venture firm based in Boulder, his belief in entrepreneurship as a driver of economic mobility, and the lessons behind his new book Capital Evolution. He also discusses backing overlooked founders, the philosophy of “give first,” winding down Foundry by design, and his latest chapter launching Good Bread, a lending platform that expands access to capital for small business owners traditionally shut out of the financial system. Show Notes: (02:10) Why Entrepreneurship Fuels Job Creation and Innovation (03:25) Capital Evolution and the Case for Dynamic Capitalism (06:05) Long-Term Thinking vs. Short-Term Market Pressure (08:45) Declining Economic Dynamism and Barriers to Opportunity (12:00) Family Roots, Class Mobility, and Early Entrepreneurial Influence (15:45) Lessons from the Dot-Com Boom, Bust, and Corporate Humility (19:30) Entering Venture Capital After the Crash (23:10) Founding Foundry and Betting on Non-Coastal Startups (27:05) Backing Overlooked Founders and Scrappy Entrepreneurs (31:40) Building a National Venture Platform from Boulder (35:10) Deciding to Wind Down Foundry and Make Space for New Funds (38:30) Writing The New Builders and Reframing Entrepreneurship (41:30) Launching Good Bread to Expand Access to Small Business Capital (45:45) What Makes Startup Ecosystems Resilient Around the World (49:40) The Enduring Power of “Give First” (54:00) Beyond the Bio: Seth Levine ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Seth Levine, Co-Founder of Foundry 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.
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Pioneering Small Business Software & Empowering Entrepreneurs w/ Gail Goodman, Founder & CEO of Constant Contact
12/03/2025
Pioneering Small Business Software & Empowering Entrepreneurs w/ Gail Goodman, Founder & CEO of Constant Contact
In this episode of Outsider Inc., host Ian Hathaway interviews Gail Goodman, former CEO of Constant Contact. Goodman discusses her journey from her early entrepreneurial endeavors to leading Constant Contact from startup to IPO and ultimately to a $1.1 billion acquisition. She emphasizes the importance of execution over ideas and how a deep commitment to small businesses shaped her approach to building and scaling a SaaS company. She also reflects on the emotional transition after 17 years as CEO and her ongoing work supporting underrepresented entrepreneurs. Show Notes: (02:57) Childhood Entrepreneurial Roots (06:59) Seeing Dysfunction Up Close and Learning What Not to Do (08:03) The Leap to Leading Constant Contact (12:09) Overcoming Imposter Syndrome and Building a CEO Peer Network (18:59) Customer Research and the Art of “Following Them Home” (21:13) Cracking Conversion and Retention in Early SaaS (30:57) Preparing for an IPO and Leading Through Rapid Scale (33:40) Public Company Pressures and Cultural Shifts (36:00) The Emotional Reality of Transitioning Out of the CEO Role (38:14) Joining Boards and Rethinking Leadership from a New Seat (44:10) Being an Outsider in Tech and Venture Capital (47:30) “People Gut” and the Art of Hiring Well (51:55) Supporting Underrepresented Entrepreneurs Through EforAll (54:00) Beyond the Bio: Gail Goodman ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Gail Goodman, Founder & CEO of Constant Contact 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.
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Leading with Love, Staying Mission Focused, and Building a Multi-Billion-Dollar Business in Atlanta w/ Kyle Porter, Founder & fmr CEO of Salesloft
11/12/2025
Leading with Love, Staying Mission Focused, and Building a Multi-Billion-Dollar Business in Atlanta w/ Kyle Porter, Founder & fmr CEO of Salesloft
In this episode of Outsider Inc., host Ian Hathaway interviews Kyle Porter, founder and longtime CEO of SalesLoft. Kyle shares his remarkable journey from nearly failing in the first year of SalesLoft to scaling the company to unicorn status with a $2.3 billion valuation. He discusses the core principles of leadership, such as leading with love, staying mission-driven, and valuing corporate culture. Kyle also reveals personal challenges, including childhood health issues and a transformative college experience, and how these shaped his entrepreneurial path. Finally, Kyle talks about his current life on a tangerine farm and supporting his wife's business endeavors, emphasizing the importance of family and personal fulfillment. Show Notes: (02:12) Leading with Love: A CEO's Perspective (02:55) Kyle's College Turning Point (04:55) Childhood Hustles: The Seeds of Sales Passion (06:52) Overcoming Childhood Health Challenges (12:57) Early Professional Experiences and Lessons Learned (15:51) The Birth and Rebirth of SalesLoft (26:49) Navigating the Pandemic: Challenges and Growth (30:41) Life Changes During the Pandemic (31:31) The Vista Equity Acquisition (34:31) Transitioning from CEO to Executive Chairman (37:16) Supporting Each Other's Dreams (44:04) Building SalesLoft in Atlanta (51:08) Beyond the Bio with Kyle Porter ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Kyle Porter, Founder & fmr CEO of SendGrid 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.
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From Introvert to IPO: Culture, Control, and Building SendGrid into a Category Leader w/ Isaac Saldana, Co-Founder & fmr CEO, SendGrid
10/29/2025
From Introvert to IPO: Culture, Control, and Building SendGrid into a Category Leader w/ Isaac Saldana, Co-Founder & fmr CEO, SendGrid
In this episode of Outsider Inc., host Ian Hathaway interviews Isaac Saldana, the co-founder and former CEO of SendGrid, and current CEO of Joy Labs. Isaac discusses the interplay of humility and confidence in leadership and shares his unconventional path to success. From being a non-English-speaking teenager who managed a family and two jobs at 19, to raising significant capital and guiding SendGrid to an IPO and a $2 billion acquisition by Twilio, Isaac reflects on the pivotal moments and decisions that shaped his career. He highlights the importance of grit, mentorship, and a values-driven approach to leadership. Isaac also touches on his current venture, Laneful, and the future of email communication infrastructure powered by AI. Show Notes: (10:42) The Entrepreneurial Spark: Rich Dad, Poor Dad (14:21) The Birth of SendGrid: Solving Email Deliverability (19:21) Navigating Early Success and Challenges (23:33) A Pivotal Decision: Replacing Himself as CEO (27:10) Scaling SendGrid to IPO (30:41) Post-SendGrid: The Birth of Joy Labs (32:40) Lane Four: Revolutionizing Email with AI (35:34) Leadership and Values in Entrepreneurship (42:42) Balancing Family and Ambition (47:20) Beyond the Bio with Isaac Saldana ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Isaac Saldana, Co-Founder & fmr CEO of SendGrid 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.
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From Midwest Outsider to Movement-Leading Industrialist: Choosing the Uphill Challenges and Rebuilding American Manufacturing w/ Aaron Slodov, Remesh & Atomic Industries
10/15/2025
From Midwest Outsider to Movement-Leading Industrialist: Choosing the Uphill Challenges and Rebuilding American Manufacturing w/ Aaron Slodov, Remesh & Atomic Industries
In this episode of Outsider Inc., our guest is Aaron Slodov, co-founder of Remesh and co-founder and CEO of Atomic Industries. Aaron shares insights from his unique journey from a child tinkering in Cleveland to working at Google X, and founding a series of innovative companies. The discussion delves into the challenges and opportunities in American manufacturing, the impact of globalization, and the role of software and AI in modern industrial systems. Aaron also touches on his vision of re-industrializing America, his belief in tackling complex problems, and his leadership in fostering a new movement through the Re-Industrialize Summit and the New American Industrial Alliance. Show Notes: (04:34) The Formative Years: From Cleveland to Google (11:23) The Birth of Remesh: A Social Experiment (15:09) Challenges and Lessons from Remesh (18:00) A New Beginning: The Genesis of Atomic Industries (20:36) The Flaws in Global Manufacturing (24:10) Building a Testbed Factory in Detroit (26:21) Merging Software with Physical Production (30:23) Scaling a Movement: Reindustrialize (33:26) Encouraging Talent in Hard Tech (36:00) Personal Insights and Reflections (40:01) Beyond the Bio with Aaron Slodov ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Aaron Slodov, Co-Founder & CEO, Atomic Industries 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.
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From Ironman Collapse to Healthcare Category Leader: Burning the Ships w/ Guillaume de Zwirek, Founder & CEO, Artera
10/01/2025
From Ironman Collapse to Healthcare Category Leader: Burning the Ships w/ Guillaume de Zwirek, Founder & CEO, Artera
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.
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Capital-Constrained & Mission-Obsessed: How Pressure Forged a Healthcare Unicorn in Iowa w/ Jon Lensing, Co-Founder & CEO, OpenLoop
09/17/2025
Capital-Constrained & Mission-Obsessed: How Pressure Forged a Healthcare Unicorn in Iowa w/ Jon Lensing, Co-Founder & CEO, OpenLoop
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.
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Founder, Operator, Investor: Lessons Across Every Seat in Latin American Tech w/ Jimena Pardo, Co-Founder, Carrot; Co-Founder & Managing Partner, Hi Ventures
09/03/2025
Founder, Operator, Investor: Lessons Across Every Seat in Latin American Tech w/ Jimena Pardo, Co-Founder, Carrot; Co-Founder & Managing Partner, Hi Ventures
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.
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Betting on Yourself, Breaking Into Tech, & Refusing to Take No for an Answer w/ Melodie van der Baan, Co-Founder & CEO, Max Retail
08/20/2025
Betting on Yourself, Breaking Into Tech, & Refusing to Take No for an Answer w/ Melodie van der Baan, Co-Founder & CEO, Max Retail
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.
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From Visual Search Founder to Visionary VC w/ Jewel Burks Solomon, Co-Founder of Partpic & Managing Partner, Collab Capital
08/06/2025
From Visual Search Founder to Visionary VC w/ Jewel Burks Solomon, Co-Founder of Partpic & Managing Partner, Collab Capital
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.
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Founder, Filmmaker, Humanitarian, & VC: Reinvention through Purpose w/ Sean O'Sullivan, Co-Founder of MapInfo & Managing GP, SOSV
07/23/2025
Founder, Filmmaker, Humanitarian, & VC: Reinvention through Purpose w/ Sean O'Sullivan, Co-Founder of MapInfo & Managing GP, SOSV
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.
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From Lagos to Birmingham: Bootstrapping to Billions and Scaling Belief Systems Through Constraints w/ Shegun Otulana, Founder & CEO of TheraNest & Harmony Venture Labs
07/09/2025
From Lagos to Birmingham: Bootstrapping to Billions and Scaling Belief Systems Through Constraints w/ Shegun Otulana, Founder & CEO of TheraNest & Harmony Venture Labs
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.
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From Hacker to Security Pioneer & Community Leader in Michigan w/ Dug Song, Co-Founder & fmr CEO, Duo Security
06/25/2025
From Hacker to Security Pioneer & Community Leader in Michigan w/ Dug Song, Co-Founder & fmr CEO, Duo Security
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.
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Give First, Mentorship, and Startup Communities w/ Brad Feld, Co-Founder of Foundry & Techstars
06/11/2025
Give First, Mentorship, and Startup Communities w/ Brad Feld, Co-Founder of Foundry & Techstars
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.
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The Outsider Who Sparked New York’s Tech Ecosystem and Backed Multiple Billion Dollar Outcomes w/ Kevin O’Connor, Co-Founder of DoubleClick, fmr CEO of Graphiq, and Founder & GP at ScOp Venture Capital
05/28/2025
The Outsider Who Sparked New York’s Tech Ecosystem and Backed Multiple Billion Dollar Outcomes w/ Kevin O’Connor, Co-Founder of DoubleClick, fmr CEO of Graphiq, and Founder & GP at ScOp Venture Capital
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.
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Bootstrapping to Exit, First Principles Thinking, Product Simplicity, and Mentoring the Next Generation w/ Jason Seats, Co-Founder of Slicehost & fmr CIO of Techstars
05/14/2025
Bootstrapping to Exit, First Principles Thinking, Product Simplicity, and Mentoring the Next Generation w/ Jason Seats, Co-Founder of Slicehost & fmr CIO of Techstars
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.
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Disrupting the Status Quo & Building Global Entrepreneurial Ecosystems w/ Linda Rottenberg, Co-Founder & CEO, Endeavor
04/30/2025
Disrupting the Status Quo & Building Global Entrepreneurial Ecosystems w/ Linda Rottenberg, Co-Founder & CEO, Endeavor
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
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From Central Missouri Hackathon to $5B Automation Platform w/ Wade Foster, Co-Founder & CEO, Zapier
04/16/2025
From Central Missouri Hackathon to $5B Automation Platform w/ Wade Foster, Co-Founder & CEO, Zapier
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.
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From Startup to IPO: Building a FinTech Giant in Charlotte w/ Michael Praeger, Co-Founder, Chairman & CEO, AvidXchange
04/02/2025
From Startup to IPO: Building a FinTech Giant in Charlotte w/ Michael Praeger, Co-Founder, Chairman & CEO, AvidXchange
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.
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Scaling Companies & Leveraging Community in Indianapolis w/ Scott Dorsey, Co-Founder & CEO, ExactTarget; Managing Partner, High Alpha
03/19/2025
Scaling Companies & Leveraging Community in Indianapolis w/ Scott Dorsey, Co-Founder & CEO, ExactTarget; Managing Partner, High Alpha
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.
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Outsider Inc. Trailer
03/07/2025
Outsider Inc. Trailer
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.
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