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.

Most Popular

Founder’s Field Guide

Ep.46

Breaking Language Barriers

Sameer Shariff is the co-founder and CEO of Cambly. We cover the origin story of the business, what Sameer views as the core functions of a two-sided marketplace, and how the team approached scaling a product that was international from day one.

08.12.2021

Play

Founder’s Field Guide

Ep.45

Disrupting the Auto Buying Experience

Ernie Garcia is the co-founder and CEO of online used car platform, Carvana. We cover effective decision-making, what it means to be a long-term thinker, and what Ernie sees as the defining features of attractive markets.

08.05.2021

Play

Founder’s Field Guide

Ep.44

Mastering On-Demand Convenience

Sebastian Mejia is the co-founder and president of Rappi. We cover the ways in which Rappi has balanced growth and unit economics, how fungibility is a key characteristic of any rewards program, and Sebastian's views of the value of brands in an increasingly app-based world.

07.29.2021

Play

Founder’s Field Guide

Ep.43

We Don’t Sell Saddles Here

Stewart is the founder and CEO of Slack. We cover the concept of owner’s delusion, how to frame the boundaries between product and market, and the challenge of changing people’s mental models.

07.22.2021

Play

Founder’s Field Guide

Ep.42

Challenging Big Ideas

Spenser Skates is the CEO and co-founder of Amplitude Analytics. We cover how Spenser’s long history in programming ties into his work at Amplitude today, the nuances of equity compensation, and his desire to see more direct listings vs. IPOs.

07.15.2021

Play

Founder’s Field Guide

Ep.41

Building the Branchless Bank

David Vélez is the founder and CEO of Nubank, the world’s largest digital bank with over 40 million customers. We cover his venture capital background at Sequoia, the pros and cons of building a digitally native business, and what gets him most excited about innovation and technology in emerging markets.

07.08.2021

Play

Founder’s Field Guide

Ep.40

Business Boss Battles

Michael is the founder and CEO of Bottomless. We cover the problems founders face when building something unique, how to avoid solving bottlenecks that don’t yet exist, and how to iterate through issues before scaling.

07.01.2021

Play

Founder’s Field Guide

Ep.39

Optimizing Human Performance

Will Ahmed is the founder of fitness wearable company, WHOOP. We cover how his own backstory ties into the founding of WHOOP, the key design decisions they made in the ultra-competitive wearables market, and how the company grew slowly before inflecting in recent years.

06.23.2021

Play

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

Play

Founder’s Field Guide

Ep.37

Everything Will Be Bought Online

Florian Hagenbuch and Mate Pencz are the co-founders of Loft, a platform designed to bring Latin American real estate into the e-commerce age. We cover the market opportunity in Brazilian real estate, the value proposition for iBuying across the US and Latin American ecosystems, and touch on the potential for Loft to expand from real estate into adjacent services.

06.09.2021

Play

Contact

Get in touch at help@joincollossus.com