In this episode of Outsider Inc., host Ian Hathaway sits down with Colorado Governor Jared Polis, a serial entrepreneur and Techstars co-founder who has spent his career blending founder instincts with public service. Jared shares how he built and exited multiple tech companies early, including BlueMountain and ProFlowers, and what those years taught him about capital, timing, and learning by doing. They also unpack how a founder mindset translates inside government, why Congress felt more like entrepreneurship than executive leadership, and how Jared approached policy like a builder. Along the way, Jared discusses accredited investor reform, why wealth is a poor proxy for competence, and the practical systems thinking behind Colorado's biggest moves, from universal preschool and insulin price caps to Bitcoin tax payments and criminal justice reform. The conversation is a rare look at what happens when a repeat founder brings startup operating principles into politics, and what outsiders can learn from it.

Show Notes:

(03:00) Early work ethic, risk tolerance, and learning in the deep end

(07:00) Three exits before 30 and the pattern behind them

(10:00) Co-founding Techstars and the early days of backing founders

(14:00) Building and scaling ProFlowers and disintermediating the supply chain

(16:00) Running for Congress and stepping into public service

(20:00) Why Congress felt like entrepreneurship, not CEO leadership

(22:00) Founder mindset in policy and the push to rethink "qualified investors"

(23:00) Outcomes as governor, universal preschool, insulin caps, pardons, and more

(19:00) Bitcoin for taxes and treating government like a system you can improve

(32:00) Advice for first-time founders and why every new founder is an outsider

(34:00) Beyond the Bio: Jared Polis

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

✅ Guest: Jared Polis, Governor of Colorado; AIS; Blue Mountain; Proflowers; Techstars

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.

In this episode of Outsider Inc., host Ian Hathaway sits down with Chris Schroeder, entrepreneur, investor, Co-Founder of Next Billion Ventures, and author of Startup Rising, to explore what American entrepreneurs and investors miss when they overlook the rest of the world. Chris reflects on a career spanning politics, media, venture-backed startups, and global investing, and shares how a 2010 trip to Dubai reshaped his thinking about entrepreneurship, emerging markets, and the future of innovation. They discuss the power of asking better questions, why humility matters more than certainty, what Silicon Valley often gets wrong about founders in other regions, and how time spent on the ground in places like the Middle East, Southeast Asia, Latin America, and China reveals patterns most people never see. Chris also shares lessons from building and selling HealthCentral, writing Startup Rising, investing through Next Billion Ventures, and why the best founders stay focused on real problems, not prestige.

Show Notes:

(03:00) Why asking better questions matters more than having all the answers

(05:00) The wonder of being wrong and learning through humility

(09:00) Family history, immigration, and the entrepreneurial mindset

(14:20) Politics, transactional relationships, and the long game of trust

(20:10) Building inside the Washington Post during digital disruption

(27:45) The HealthCentral thesis and why community can save lives

(33:10) The Dubai trip that changed Chris Schroeder's life

(38:00) Writing Startup Rising and seeing what others missed in the Middle East

(41:30) Why global founders need to be understood on their own terms

(50:45) What Chris learns by getting on the ground in China

(55:20) The questions American entrepreneurs and investors should be asking now

(58:45) The danger of "third cappuccino syndrome" and losing focus on what matters

(1:00:00) Beyond the Bio: Chris Schroeder

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

✅ Guest: Chris Schroeder, Next Billion Ventures; Author of Startup Rising; former CEO, HealthCentral

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.

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.

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

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.

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.

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.

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.