About this episode

Jascha Kaykas-Wolff discusses leadership, AI in hospitality, and the importance of relationships in tech.

Jascha Kaykas-Wolff is the CEO of Visiting Media and a longtime tech leader who has helped shape digital marketing at companies like Yahoo, Microsoft, BitTorrent, and Mozilla. Raised in a socialist collective outside Eugene, Oregon, by a pioneering rock concert promoter, he grew up thinking deeply about systems, autonomy, and how teams work together. Susan and Jascha talk about AI acceleration, authentic leadership, and agile innovation. What You'll Learn • Breaking into hospitality tech by showing up, meeting operators, and building real relationships • How growing up in a collective shaped a leadership philosophy of autonomy and accountability • The difference between meritocracy and psychological safety in organizations • How data and conviction helped pitch Bill Gates and Steve Ballmer • The surprising leadership lesson hidden in a mustard stain • Why curiosity—not credentials—is the most valuable career skill today • Practical ways hospitality professionals can start experimenting with AI immediately • Using AI to research guests, build microsites, and automate everyday work • How Visiting Media uses real-world capture plus AI to power hospitality sales • The importance of…

People in this episode

Host: Susan Barry

Guest: Jascha Kaykas-Wolff

Mentioned in this episode

Organizations: Visiting Media, Yahoo, Microsoft, BitTorrent, Mozilla

Places: Eugene, Oregon

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