Founder’s Field Guide

Founder's Field Guide is a series of conversations with founders, CEOs, and operators who are building great businesses.

Patrick O'Shaughnessy Host Patrick O'Shaughnessy

Patrick is the Founder and CEO of Positive Sum. He founded Colossus in 2020 to build on the success of Invest Like the Best.

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Founder’s Field Guide

Ep.36

Innovation in Static Industries

Assaf Wand is the CEO and co-founder of Hippo, a homeowner insurance startup founded in 2015. We cover how Hippo approached innovation in the highly regulated insurance industry, unique strategies for building brand trust, and how direct relationships with homeowners have opened up Hippo's business model to a wide range of opportunities.

06.03.2021

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Founder’s Field Guide

Ep.35

Building the Financial Center of Gravity

Henrique Dubugras is the co-founder and CEO of Brex. We cover Brex’s transition from a credit card for start-ups to the central account for businesses, why building that central account was orders of magnitude more difficult than expected, and the difference between building a business in Brazil and the US.

05.26.2021

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Founder’s Field Guide

Ep.34

Learning How to Sell

Peter Reinhardt is the co-founder and CEO of Segment, a market-leading customer data platform. We cover the lessons Peter has learned throughout his journey running Segment, why revenue operations is an underrated aspect of any business, and the current data use trends.

05.20.2021

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Founder’s Field Guide

Ep.33

Manufacturer to Customer

Jeremy Cai is the founder and CEO of Italic, a subscription marketplace for consumer goods that works directly with manufacturers. We cover Italic's business model, the evolving role of manufacturers in supply chains, and the concept of building the next “everything store.”

05.13.2021

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Founder’s Field Guide

Ep.32

Lessons in Process Power

James Reinhart is the founder and CEO of thredUP an online thrift marketplace. We cover the competitive advantages of building processing plants from the ground up, how thredUP went from negative gross margins to strong unit economics, and the future of retail.

05.06.2021

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Founder’s Field Guide

Ep.31

Supply, Demand, and the Outdoors

Alyssa Ravasio is the co-founder and CEO of Hipcamp. We cover how Alyssa bootstrapped demand in the early days, the importance of creating magical experiences for your customers, and the evolution of Hipcamp's business model

04.29.2021

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Founder’s Field Guide

Ep.30

New Physics of Business

Thomas Tull is the founder of Tulco. We cover the movie industry's value chain, how Legendary Entertainment pioneered the use of data analytics to improve their odds of success, and Thomas’ concept of the new physics of business

04.22.2021

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Founder’s Field Guide

Ep.29

Building Web 3.0

Trevor McFedries is the founder of technology startup Brud and the creator of virtual pop star Miquela, a Gen Z icon with millions of fans worldwide. We cover the music-industrial complex, the creation of Miquela, and what Web 3.0 will mean for creators and builders.

04.15.2021

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Founder’s Field Guide

Ep.28

A Human and Math Problem

Tony Xu is the co-founder and CEO of DoorDash. We cover the origins of DoorDash, how to approach and solve difficult problems, and the leadership lessons he's learned from running DoorDash.

04.08.2021

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Founder’s Field Guide

Ep.27

A Primer on Performance Marketing

Jesse Pujji is the Founder & CEO of Gateway X. We cover how revenue mechanics affect ad campaigns, why long sales funnels often offer the greatest opportunities for differentiation, and the various channels and strategies available for performance marketing

04.01.2021

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