About
Founder's Field Guide is a series of conversations with founders, CEOs, and operators who are building great businesses.
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.
Featured
Founder’s Field Guide
Ep.24
Building the Modern Restaurant
Jonathan Neman is the co-founder and CEO of Sweetgreen. We cover the origins of Sweetgreen and how it builds a direct relationship with its customers, how Jonathan thinks restaurants should work with marketplaces, and the economics of operating restaurants.
03.11.2021
Founder’s Field Guide
Ep.14
The Growing Importance of Design
Dylan is the co-founder and CEO of Figma, a collaborative online design tool. We cover the principles that Figma is built upon, the growing importance of design as the world moves from consumption to creation, and what it takes to recruit effectively.
12.31.2020
Founder’s Field Guide
Ep.38
Building the New Standard in Security
Christina Cacioppo is the founder of Vanta, a security and compliance software business founded in 2017. We cover the experiences that led her to launch Vanta, the strategy she took to build, price, and distribute the product, and we touch on her lessons from running a growing organization.
06.17.2021
Collections
Most Popular
Founder’s Field Guide
Ep.6
Pattern Matching, Playbooks, and Winning Product Categories
John was the CEO of Cisco from 1995 to 2015. We cover how to capitalize on market transitions enabled by new technologies, the key learnings from acquiring over 180 companies with Cisco, and leadership lessons from Jack Welch and Shimon Peres.
11.05.2020
Founder’s Field Guide
Ep.5
When Digital and Physical Worlds Converge
Laura Behrens Wu is the co-founder and CEO of Shippo. We cover the early days of Shippo finding its first customers, how Shippo's strategy has evolved over the years, and the complexity involved when digital and physical worlds collide.
10.29.2020
Founder’s Field Guide
Ep.4
Building the Third Place
Jason is the founder and CEO of Discord, a communications network with over 100 million monthly users and communities for every topic you could imagine. We cover the evolving business model for video games, Discord's early distribution methods, and Discord's hiring philosophy.
10.22.2020
Founder’s Field Guide
Ep.3
Creating and Selling Superpowers
Leore is the co-founder and CEO of Lob and Alt. We cover how APIs enable developers to create superpowers, pricing strategy for businesses, and collectibles as financial assets.
10.15.2020
Founder’s Field Guide
Ep.2
How Regulation Unlocks Opportunity
Justin Singer is the founder and CEO of Caliper Foods and Stillwater Brands. We cover how regulation creates or destroys business and investing opportunities, the path of marijuana legalization, and the ins and outs of the cannabis industry.
10.08.2020
Founder’s Field Guide
Ep.1
Using Emotion to Design Great Products
Rahul is the Founder & CEO of Superhuman, the fastest email experience ever made. We cover the idea of using game design & emotion in building products, the framework for achieving product market fit, and Rahul's philosophy when it comes to investing in other startups.
10.01.2020