Outsider Inc.

Ian Hathaway
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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.

  1. Turning Struggle into Strategy w/ Willy Schlacks, Co-Founder & President, EquipmentShare

    1 APR

    Turning Struggle into Strategy w/ Willy Schlacks, Co-Founder & President, EquipmentShare

    In this episode of Outsider Inc., host Ian Hathaway sits down with Willy Schlacks, Co-Founder and President of EquipmentShare, to explore what it really looks like to build a category-defining company outside Silicon Valley. Willy shares how EquipmentShare grew from operator pain in the field into a vertically integrated construction tech platform spanning technology, equipment, and services, and why embracing constraint can be a strategic advantage, not a limitation. They dig into the chaos of jobsite operations, the early decision to take a platform approach, what Willy learned from time inside Y Combinator, and how building from Missouri forced the company to master scale early. Willy also reflects on taking EquipmentShare public at a $7B valuation, building the startup ecosystem through Redbud VC, and what he looks for in founders when the hard part is still ahead.   Show Notes:   (03:00) Why struggle and friction can be an advantage (10:00) Curiosity, questions, and what "creation" really means (16:10) Reframing mistakes and failure as fuel (19:05) The operator pain behind EquipmentShare (23:00) The jobsite moment that forced the idea into motion (27:00) Inside Y Combinator and what Willy learned from the Silicon Valley bubble (29:05) Building from Missouri and the meaning of "home" (32:45) Constraint as a forcing function for scale, systems, and resilience (35:25) Going public and what founders misunderstand about the shift (38:10) Redbud VC and building an ecosystem close to home (41:10) What Willy looks for in founders when success is still unproven (46:05) Legacy, ritual, and the long game of creation (48:00) Beyond the Bio: Willy Schlacks     ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Willy Schlacks, Co-Founder & President, EquipmentShare   Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.   Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

    56 min
  2. Building Better, Not Bigger: Mentorship, Networks, and Startup Communities w/ David Cohen, Co-Founder & CEO, Techstars

    18 MAR

    Building Better, Not Bigger: Mentorship, Networks, and Startup Communities w/ David Cohen, Co-Founder & CEO, Techstars

    n this episode of Outsider Inc., host Ian Hathaway sits down with David Cohen, Co-Founder and CEO of Techstars, to unpack how a community-first mindset helped reshape what founder support can look like far beyond Silicon Valley. David traces his path from early founder wins and failures to building Techstars out of a small Boulder experiment rooted in mentorship and Give First. They discuss why networks and trust matter as much as capital, the hard tradeoffs that come with scale, and why David returned to the CEO seat with a renewed focus on quality, founder outcomes, and long-term community strength. Along the way, David breaks down his founder evaluation mantra, why teams beat ideas, what he believes most investors overvalue, and how to sustain a founder journey without losing yourself to it.   Show Notes:   (03:10) Community as the through line from the beginning (08:25) Early computing and the power of networks (12:40) First startup lessons and "unsucking" real problems (16:35) Why Boulder and how place shaped the journey (22:15) The moment networks became the unlock (26:30) Building Techstars with mentorship and Give First (31:50) Culture, scale, and why "better is better" (37:05) How David evaluates founders: Team, team, team (42:20) What most people overvalue in startups (46:15) Founder mode, identity, and work life harmony (52:30) Outsiders, underestimated founders, and why the model works (57:10) Beyond the Bio: David Cohen   ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: David Cohen, Co-Founder & CEO, 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

    54 min
  3. Founder, Operator, Investor: Building Latin America's Tech Ecosystem from Scratch w/ Hernan Kazah, Co-Founder, Mercado Libre & Managing Partner, Kaszek

    4 MAR

    Founder, Operator, Investor: Building Latin America's Tech Ecosystem from Scratch w/ Hernan Kazah, Co-Founder, Mercado Libre & Managing Partner, Kaszek

    In this episode of Outsider Inc., host Ian Hathaway sits down with Hernán Kazah, co-founder of Mercado Libre and Managing Partner at Kaszek, to trace the outsider journey that helped put Latin America on the global tech map. Hernan reflects on growing up in Buenos Aires, the early lessons that shaped his resilience, and how his time at Procter & Gamble sharpened his appreciation for process and execution. After arriving at Stanford as an English learner, he caught the wave of the internet boom, met Marcos Galperin, and helped launch Mercado Libre in 1999. A moment when internet adoption in the region was near zero, capital was scarce, and there was no startup ecosystem to lean on.   Hernan walks through raising money in the dot-com window, surviving the crash by cutting marketing, doubling down on product and organic growth, reaching profitability in 2006, and ultimately taking Mercado Libre public in 2007. He then shares why he stepped away in 2011 to co-found Kaszek with a clear mission: bring early, high-conviction capital and real operator support to the next generation of Latin American founders. Along the way, he breaks down what he looks for in entrepreneurs and why building in emerging ecosystems often requires solving more than one problem at a time. We also dig into Kaszek's track record backing category-defining companies like Nubank, Creditas, QuintoAndar, and Kavak, and why Hernan remains bullish on the region's potential. His guiding principle is simple: move with conviction … or don't move at all.   Show Notes:   (06:55) P&G Lessons On Process (11:10) Stanford Culture Shock (16:34) Saying Yes To Mercado Libre (20:08) Building In A No-Ecosystem Market (23:55) Dotcom Crash And Capital Discipline (29:05) IPO Validation And Profitability (32:40) Leaving Mercado Libre (33:47) Founding Kaszek (42:07) What Kaszek Looks For (46:18) Outsider Playbook in LatAm (54:43) Legacy and Ecosystem Hopes (57:21) Beyond the Bio with Hernan Kazah   ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guest: Hernan Kazah, Co-Founder, Mercado Libre & Managing Partner, Kaszek   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.

    1hr 5min
  4. Dynamic Capitalism & Building Entrepreneurial Ecosystems Anywhere w/ Seth Levine, Co-Founder of Foundry

    17/12/2025

    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.

    56 min
  5. Pioneering Small Business Software & Empowering Entrepreneurs w/ Gail Goodman, Founder & CEO of Constant Contact

    03/12/2025

    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.

    59 min
  6. Leading with Love, Staying Mission Focused, and Building a Multibillion-Dollar Business in Atlanta w/ Kyle Porter, Founder & fmr CEO of Salesloft

    12/11/2025

    Leading with Love, Staying Mission Focused, and Building a Multibillion-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.

    58 min
  7. From Introvert to IPO: Culture, Control, and Building SendGrid into a Category Leader w/ Isaac Saldana, Co-Founder & fmr CEO, SendGrid

    29/10/2025

    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.

    54 min
  8. From Midwest Outsider to Movement-Leading Industrialist: Choosing the Uphill Challenges and Rebuilding American Manufacturing w/ Aaron Slodov, Remesh & Atomic Industries

    15/10/2025

    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.

    47 min
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About

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.

Information

  • Creator
    Ian Hathaway
  • Years Active
    2025 - 2026
  • Episodes
    24
  • Rating
    Explicit
  • Copyright
    © 2025
  • Show Website
    Outsider Inc.

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