TOP CEO

Ben Kaplan positions TOP CEO as a "business school case study in audio form," and that framing actually holds up across the show's 38 episodes. Each conversation zeroes in on the toughest decisions a CEO has faced — the strategic pivots that almost killed the company, the moments when conventional wisdom was dead wrong, and the daring moves that either paid off spectacularly or became expensive lessons. Guests range from scrappy startup founders to Fortune 500 executives, covering industries from fitness and food to biotech and SaaS. Kaplan's interviewing style pushes guests past their rehearsed talking points toward the messier, more interesting truths. Recent episodes have covered crisis management during public failures, brand transformation after acquisitions, mentorship platforms, and the emotional weight of family business succession. The show was putting out episodes twice a week at its peak but appears to have paused after January 2025, so the current status is uncertain. No ratings on Apple Podcasts yet. Despite the hiatus, the back catalog is worth working through — the case-study format means episodes don't age out the way news-driven content does. If you want to understand how real CEOs made real decisions under real pressure, without the sanitized version they give at conferences, this show delivers that consistently.