Founder’s Field Guide

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.16

The Secret Fintech Giant

Oliver Hughes is the CEO of Tinkoff. We cover how Tinkoff used direct mailshots to become the largest online bank in Russia, how they build profitability into all their business lines, and why they own the largest door-to-door logistics operation in Russia.

01.14.2021

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Founder’s Field Guide

Ep.15

Lessons from the Amazon Ecosystem

Carlos Cashman is the co-founder and co-CEO of Thrasio, an acquirer of third-party Amazon sellers. We cover how the third-party Amazon seller ecosystem works, the future of e-commerce, and lessons that he's learned building Thrasio into a $1B company.

01.07.2021

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Founder’s Field Guide

Ep.14

The Growing Importance of Design

Dylan Field 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

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Founder’s Field Guide

Ep.13

The Future of Financial Services

Zach Perret is the co-founder and CEO of Plaid. We discuss Zach's philosophy on building products, how the financial system works today, and the trends Zach is seeing from the next wave of FinTech companies launching on Plaid.

12.24.2020

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Founder’s Field Guide

Ep.12

Lessons from Building Media Empires

Bob Pittman has a storied career that includes running MTV, AOL, Six Flags, and is now the CEO of iHeartMedia. We cover his philosophy on the consumer, the lessons he learned while creating MTV, and the future of the media landscape with the abundance of user-generated content.

12.17.2020

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Founder’s Field Guide

Ep.11

Protecting the Internet

Michelle Zatlyn is the co-founder and COO of Cloudflare, a now $25 billion dollar business which she helped take public last year. We cover the catalyst for starting CloudFlare, the future of distributed storage and computing power, and the importance of great co-founders and partners.

12.10.2020

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Founder’s Field Guide

Ep.10

How Government Works

Zac Bookman is the Founder and CEO of OpenGov a budgeting and financial management software for local governments. We discuss how local governments are structured, how to build an enterprise sales machine, and the role capital efficiency plays in building great companies.

12.03.2020

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Founder’s Field Guide

Ep.9

The New Language of the Internet

Emmett Shear is the co-founder and CEO of Twitch. We dive into how emotes are evolving into the new "language" for the internet, how Twitch's most successful products have come from watching users, and why founders should focus on "winning" a narrow niche of customers before expanding.

11.26.2020

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Founder’s Field Guide

Ep.8

Know What You Are Selling

Nick Kokonas is the CEO of Tock and co-owner of some of the world’s best restaurants & bars: Alinea, Next, and The Aviary. We cover misconceptions of starting a restaurant, improving the profitability of any business, and the importance of understanding what you really sell.

11.19.2020

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Founder’s Field Guide

Ep.7

Creating and Defining a New Market Category

Todd McKinnon is the co-founder and CEO of Okta. We cover why Todd felt the 2008 Crisis was a good time to start Okta, how he pivoted into identity management, and the lessons he’s learned from scaling Okta into a public company.

11.12.2020

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