Terry Kawaja: 37 Years of Investment Banking, 55 Years of Comedy, and the Future of AdTech & AI

About this episode

Terry Kawaja discusses his extensive experience in investment banking and comedy, along with insights on AI in advertising and the future of AdTech.

🎙️ "I'm 100 years old, which is why I've seen this before."That's Terence Kawaja . Creator of the LUMAscape. Founder & CEO of LUMA Partners . 37 years in investment banking. 55 years of comedy. And still calling balls and strikes in AdTech & Media better than anyone.If you've ever used a LUMAscape in a presentation, you already know his work. 24 million views. Published in The Wall Street Journal. Started as an internal tool he built to understand how the ecosystem actually worked.We have over 100 mutual connections so I know many of you already know Terry. Possible's Christian Muche officially introduced us recently but it's crazy that we have crossed paths for so long (and I even started at Salomon Smith Barney right after Terry had left after the AOL Time Warner merger - my interviewers worked on that merger too!)On BOSS this week, Terry dropped some real talk on AI in advertising:💡 "Creating agents is easy. Everyone's doing it." 💡 "Efficiency is a 10% improvement. Effectiveness is a 10x delta." 💡 First wave of AI in ad tech = workflow. The real differentiator? Decisioning.We also talked about: → Why he originally refused to do an AI LUMAscape and what changed his…

People in this episode

Host: Ali Levitan

Guest: Terry Kawaja

Topics covered

• Investment Banking
• Comedy
• AdTech
• AI
• M&A Advisory
• Decisioning

Keywords

• LUMAscape
• AdTech
• AI
• Investment Banking
• Comedy
• M&A Advisory
• Decisioning

Mentioned in this episode

Organizations: LUMA Partners, The Wall Street Journal, Salomon Smith Barney, AOL Time Warner

More episodes of BOSS by Ali Levitan

• Every day feels like a shift in what's POSSIBLE - BOSS is back with Possible's Co-Founder, Christian Muche · April 7, 2026 · 13 min
• Breaking the Rules of Leadership with The Female Quotient's CEO & Founder, Shelley Zalis · March 31, 2026 · 12 min
• BOSS with Steven Wolfe Pereira, CEO Alpha | No One Wants to Look Dumb About AI · February 12, 2026 · 12 min
• BOSS with my boss, Tim Barnes, GM AWS for Advertising & Marketing · December 19, 2025 · 13 min
• AdTech, Agentic AI, and Saying What Others Won’t - BOSS with Ari Paparo · November 19, 2025 · 13 min
• BOSS with Marie Han Silloway, Gartner's Executive Partner on Risk, Reward, and AI · October 17, 2025 · 11 min