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.