Executive Mode: Inside the AI Playbook of Founder & Operator Adam Pleasant
Welcome to Episode 3 of Executive Mode, the series where we sit down with executives and founders across industries to talk about how they are actually using the latest technology in their day to day, and then have them show us live.
This episode, we are joined by Adam Pleasant, Founder & CEO of The Outcome Company, an AI-native platform delivering 100 fixed-scope outcomes across health, financial, legal, and other verticals. Adam also serves as Head of Strategic Initiatives & Ventures at Truffle Pig, a Chicago single-family office, and as AI Chief at Decennial Group, a private equity firm spanning data centers, controlled environment agriculture, and multi-family housing.
We get into how Adam thinks about building AI-native businesses, and how he is applying AI across multiple industries. Then, we move from theory to practice and have him show us how this thinking comes to life.
Our hosts🎤
Gus Spathis
Founder & CEO, Xogito
Gus’ career spans over 30 years, managing businesses and award-winning teams and technology. He has focused on realizing entrepreneur’s visions by solving difficult problems efficiently and creating breakthrough solutions.
As an entrepreneur himself he has participated in founding over a dozen different companies. He is a sought-after advisor by venture capitalists, angel investors, and private equity firms.
Adam Pleasant
CEO of The Outcome Company
Adam Pleasant is the founder and CEO of The Outcome Company, an AI-native platform delivering 100 fixed-scope outcomes across health, financial, legal, and other verticals. He concurrently serves as Head of Strategic Initiatives & Ventures at Truffle Pig, a Chicago single-family office, and as AI Chief at Decennial Group, a private equity firm spanning data centers, controlled environment agriculture, and multi-family housing.
About Xogito
Xogito partners with startups and enterprises to design and deliver scalable, high-performance systems using modern engineering and AI-driven practices. With over 20 years of experience, Xogito helps teams launch new products, rebuild fragile MVPs, modernize infrastructure, and implement intelligent workflows that scale with the business.