Allison Pickens - Investor & Former COO at Gainsight

Allison Pickens - Investor & Former COO at Gainsight

We chat with Allison about her path from writing and consulting to leading in the SaaS and AI investment world. She shares how writing has shaped her career, how her view of time has evolved, and what AI means for modern business. We also dive into team dynamics, redefining success, and her personal take on efficiency and balance.

Jair Clarke - Advisor & Former Global CTO at Microsoft

We talk with Jair Clarke about his journey from the streets of Miami to successful entrepreneurship—and the lessons he's learned about time, money, and purpose. Jair shares how authenticity, intentional time management, and AI are reshaping the way leaders think about work. We explore storytelling inside organizations, the value of qualitative data, and how to navigate AI transformation with clarity and focus.

Dave Heath - Founder & CEO at Bombas

We sit down with Dave Heath, founder and CEO of Bombas, to explore his evolving relationship between time, work, and leadership. From his early days selling Cutco knives to building a nine-figure business rooted in impact, Dave shares how time became his most valuable resource. We talk about intentional time management, the role of AI in reshaping workflows, and why obsessing over small details can drive big impact. It's a deep, honest look at what it means to lead with purpose—and how to make every hour count.