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.56

Powering Emerging Markets Payments

Sebastian Kanovich is the CEO of dLocal. We cover dLocal’s playbook for facilitating payments in emerging countries, what Sebastian has learned about great API building, and how he challenges himself to improve personally.

02.24.2022

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Founder’s Field Guide

Ep.55

Simplifying Fund Closing

Tim Flannery is the co-founder of venture fund administrator Passthrough. We discuss the biggest frictions in investing, what achieving greatness in distribution and sales looks like, and the power of identity as a feature to build products around.

02.17.2022

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Founder’s Field Guide

Ep.54

One Foot in Front of the Other

Nick Saltarelli is the co-founder of Mid-Day Squares. We cover the importance of Mid-Day Squares’ $100 million revenue target, what’s wrong with the CPG industry today, and how to keep a long-term mindset while making the most of every day.

12.23.2021

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Founder’s Field Guide

Ep.53

An Everything Store for Digital Assets

Devin Finzer is the co-founder and CEO of OpenSea. We cover OpenSea's origin story, how Devin differentiates between the spectrum of NFTs in the market, and what he sees as the major risks and opportunities in the future of the industry.

10.07.2021

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Founder’s Field Guide

Ep.52

Making Better Loans

Dave Girouard is the co-founder and CEO of Upstart. We cover the past, present, and future of lending, the differences between public and private market investors from a founder’s perspective, and the lessons Dave has learned about building speed into a habit.

09.30.2021

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Founder’s Field Guide

Ep.51

Helping Creators Build Communities

Gina Bianchini is the founder and CEO of Mighty Networks. We cover the differences between leadership and management, the lessons Gina learned building a similar business in the 2000s with Marc Andreessen, and the elements that make up a thriving community.

09.23.2021

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Founder’s Field Guide

Ep.50

The Future of Social Gaming

Justin Waldron is the co-founder and President of Playco. We cover how Justin sees the future of gaming as social platforms evolve, how gaming may be the next tool for content creation, and how Playco has approached aligning incentives for game creators and players.

09.16.2021

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Founder’s Field Guide

Ep.49

Mapping the Metaverse Economy

Gabby Dizon is the co-founder of Yield Guild Games. We cover YGG’s decentralized structure, the unit economics of its business model, and how Gabby thinks about the volatility of crypto assets when trying to build a durable, long-term business.

09.02.2021

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Founder’s Field Guide

Ep.48

A Playbook for Startups

Mike Maples, Jr. is a co-founding partner at Floodgate. We cover Mike's early insights and secrets, value hypothesis testing, and how he found himself building businesses in Silicon Valley.

08.26.2021

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Founder’s Field Guide

Ep.47

Redesigning the Home Buying Experience

Max Simkoff is the founder and CEO of Doma. We cover the history behind mortgage closings, where Title companies fall into that process, and what Max has learned from building a tech business in an antiquated industry.

08.19.2021

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