In this episode of Breaking Through the Mayhem, host Ben Lambert sits down with Steve Wolf, Head of Integrated Media at Scale Marketing, to trace his two-decade journey across the media industry—from his first break at MediaVest to leading integrated planning at an independent agency.

Steve shares how pivotal career moments shaped him: from cutting his teeth on Continental Airlines and Capital One, to learning hard lessons under tough mentors at GroupM, to managing Super Bowl negotiations for AB InBev, and later embracing entrepreneurial risk at Canvas and Horizon. Throughout, he reflects on how failure, risk-taking, and mentorship played defining roles in building his leadership style.

The conversation dives deep into:

• Failure as fuel: Why the hardest lessons and biggest setbacks often teach more than success.


• Breaking down silos: How he bridges traditional and digital media thinking to reflect how consumers actually experience content.


• CTV’s rise: Why connected TV offers the best of both linear reach and digital targeting, and how brands can use it effectively.


• AI in media planning: Why AI is powerful for speed and efficiency, but real differentiation comes from human “taste” and perspective.


• Team and culture: Why collaboration, soft skills, and curiosity often matter more than being the “smartest person in the room.”
  
  
  
  

Steve also shares personal reflections on his move from St. Louis to New York to Chicago, his love for sports and how it shapes his perspective on leadership and teamwork, and even his passion for Indiana Hoosiers football.

This episode is a masterclass in blending career grit, evolving with the industry, and leading with both strategy and humanity.