Tony Caliendo

Tony Caliendo has spent over a decade coaching high-performing entrepreneurs and executive teams across hospitality, real estate, insurance, and financial services—helping leaders who look successful on paper figure out why it doesn't feel that way. His central insight: Success built on misalignment eventually collapses under its own weight, and the fix usually isn't doing more—it's identifying what to eliminate. That framework is now the subject of his new book, Less Over More, which gives high achievers a practical model for stripping away inherited goals and unconscious pressure so growth becomes sustainable instead of exhausting. Tony blends strategic clarity with psychological precision, and he's a compelling guest for any conversation about burnout, leadership, redefining success, or building a business (and life) that doesn't require sacrificing yourself to sustain it.