One Hard Lesson Away From Serving at the Highest Level
Fri Dec 12 2025
On this episode of The One Away Show, we sit down with Andrew Sherman — attorney, educator, and author of 26 books — who has spent nearly four decades advising entrepreneurs with rare empathy, strategic clarity, and calm. Andrew shares the early hardships that shaped him, the first venture that taught him what founders carry, and the inflection point that changed his path: choosing to support entrepreneurs rather than become one. We talk about the long-game mindset, why purpose is something you owe to yourself and the people you love, and how "mutuality" is the foundation of every meaningful relationship. Andrew also reflects on writing his first book at 26, the discipline of consistency, and the moments — like testifying before Congress or helping unlock hidden enterprise value — that reminded him he was on the right road. This is a conversation about perspective, resilience, and the kind of wisdom that only comes from time.
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On this episode of The One Away Show, we sit down with Andrew Sherman — attorney, educator, and author of 26 books — who has spent nearly four decades advising entrepreneurs with rare empathy, strategic clarity, and calm. Andrew shares the early hardships that shaped him, the first venture that taught him what founders carry, and the inflection point that changed his path: choosing to support entrepreneurs rather than become one. We talk about the long-game mindset, why purpose is something you owe to yourself and the people you love, and how "mutuality" is the foundation of every meaningful relationship. Andrew also reflects on writing his first book at 26, the discipline of consistency, and the moments — like testifying before Congress or helping unlock hidden enterprise value — that reminded him he was on the right road. This is a conversation about perspective, resilience, and the kind of wisdom that only comes from time.