Host Ian Hathaway interviews Jim McKelvey, co-founder of Square and author of The Innovation Stack, about why frustration has driven some of the most important work of his career. McKelvey traces his path from writing a computer science textbook out of spite and making a living as a glassblower to building Mira, where he hired a 15-year-old Jack Dorsey and later rebuilt the company with him in secret when the rest of the team resisted change. He explains why he is more comfortable as an outsider than an insider, why he tends to build for people who have been excluded from existing systems, and how his friend Bob inspired the mission behind Square. McKelvey also shares the story of building Square's first hardware for a meeting with Steve Jobs, only to discover that an aluminum reader was picking up Jack Dorsey's heartbeat before a demo with Michael Bloomberg. He discusses what happened when Amazon tried to compete directly with Square, how that experience led him to develop the concept behind The Innovation Stack, and what Southwest Airlines founder Herb Kelleher taught him about building advantages that are difficult to copy. They also explore leadership, risk, civic work in St. Louis, why money and fame are weak motivators for McKelvey, and his belief that doing something truly new means being unqualified by definition, and doing it anyway.

Show Notes:

(02:00) Writing A Textbook Out Of Frustration
(04:00) Why Jim Is More Comfortable As An Outsider
(06:00) Making A Living As A Glassblower
(08:00) The Loss That Forced Him To Focus
(10:00) Meeting A 15-Year-Old Jack Dorsey
(11:00) Secretly Rebuilding Mira With Jack Dorsey
(14:00) Giving Leaders Real Authority
(17:00) Building Square For People The Financial System Left Out
(23:00) The Rules And Regulations That Nearly Stopped Square
(25:00) Steve Jobs, Michael Bloomberg And Jack Dorsey's Heartbeat
(31:00) What Happened When Amazon Came After Square
(33:00) The Idea Behind The Innovation Stack
(37:00) What Herb Kelleher Taught Him About Innovation
(42:00) Why Money And Powerful People Rarely Solve The Problem
(46:00) Why Frustration Is A Better Motivator Than Pride
(50:00) Beyond The Bio with Jim McKelvey

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

✅ Guest: Jim McKelvey - Co-Founder of Square

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.

Host Ian Hathaway interviews Joe Petsick, co-founder of Proxibid and co-founder and CEO of Auctic, about building technology companies from Omaha before there was much of a startup ecosystem to support them. Petsick traces his path from finance and the early dot-com era to launching online auction technology at a live sale in France, where the software had never been tested in the real world and he had never attended an auction before. After LeftBid collapsed during the dot-com downturn, he and three partners started Proxibid in 2001, building a company around empowering auctioneers rather than replacing them. Petsick shares what it was like to raise capital and scale a startup without an established local playbook, why he and his co-founders eventually hired a CEO with the authority to fire them, and how customer feedback changed the way they thought about product development. He also discusses leaving Proxibid after nearly two decades, helping strengthen Nebraska's startup ecosystem through the University of Nebraska and Open Range, and returning to entrepreneurship with Auctic. They explore the dangers of scaling too quickly, why Auctic deliberately shut down sales to prepare for growth, how Petsick evaluates early-stage founders, and why he believes the best way to win is often to make the people around you stronger.

Show Notes:

(02:00) How To Tell If You're Early Or Just Wrong
(04:00) Discovering An Entrepreneurial Mindset In Omaha
(08:00) Launching Auction Software Before Knowing If It Would Work
(12:00) What The Dot-Com Bust Taught Him About Capital
(13:00) Building Proxibid Without A Startup Ecosystem
(18:00) Why Proxibid Empowered Auctioneers Instead Of Replacing Them
(22:00) The Three Questions He Uses To Evaluate Early-Stage Startups
(29:00) Hiring A CEO Who Could Fire The Founders
(32:00) Leaving Proxibid And Returning To The University Of Nebraska
(34:00) Building A Stronger Startup Ecosystem Through Open Range
(37:00) Why He Started Auctic
(47:00) Winning By Making The People Around You Better
(48:00) Beyond The Bio with Joe Petsick

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

✅ Guest: Joe Petsick - Co-Founder of Proxibid & Auctic

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.

Host Ian Hathaway interviews Pierpaolo Barbieri, founder and CEO of Ualá and founder of early-stage venture fund 17Sigma, about leaving a successful career on Wall Street to build a new kind of financial institution in Argentina. Growing up during Argentina's 2001 financial crisis sparked Barbieri's interest in economic history and eventually took him to Harvard, Cambridge, and a career in global finance. But after seeing how many people in his home country lacked access to basic financial services, he returned to Buenos Aires to build Ualá. Barbieri discusses his reluctance to become CEO, the challenges of building a fintech company through years of economic turmoil, and why those conditions pushed Ualá to expand across products and countries. He also shares how he manages imposter syndrome, builds teams that challenge him, and works to preserve Ualá's technology-driven culture as the company grows. They explore the balance between expanding access to credit and managing risk, Barbieri's efforts to support the next generation of Latin American founders, the personal cost of entrepreneurship, and the responsibility he still feels toward the country that gave him his start.

Show Notes:

(02:00) Leaving Wall Street To Build Ualá in Argentina

(04:00) How Argentina's Financial Crisis Shaped His Path

(06:00) Debate, Harvard, And Betting On Himself

(09:30) From Economic Historian To Fintech Founder

(13:30) Becoming The CEO He Never Planned To Be

(15:30) Building For Customers Traditional Banks Overlooked

(18:30) How Argentina's Economic Turmoil Made Ualá More Resilient

(20:30) Managing Imposter Syndrome As A Founder

(23:30) Keeping Your Ego In Check And Hiring Better People

(25:30) Becoming A Bank Without Losing Your Tech DNA

(29:30) Expanding Access To Credit While Managing Risk

(31:30) Investing In The Next Generation Of Latin American Founders

(35:30) The Personal Cost Of Building A Company

(41:30) Beyond The Bio with Pierpaolo Barbieri

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

✅ Guest: Pierpaolo Barbieri - Ualá Founder & CEO

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.