HeyJaredHidden Value with David Sherry
Find what’s unseen, undervalued, or underdeveloped in people, ideas, and systems and turn it into leverage.
- Indexed issues, last 90 days
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- Sep 15, 2026
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- Jul 7, 2026
Latest issues
How to Trust Your Next Chapter Before It Makes Sense (opens the original)
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I recorded something personal this week about the different seasons of my work, from building Death to Stock to becoming an advisor and now feeling pulled toward another chapter. It’s about that strange moment when the old thing still works, but you can feel it no longer fits in the same way. I’m still finding the simplest way to talk about it so I’d genuinely love your honest reaction: what resonated, or where you wanted me to go deeper on?xx David
Five Small Rules for Having Better Conversations (opens the original)
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I’ve noticed that I’m very comfortable in a conversation when I’m the one asking the questions. I know how to follow my curiosity, keep the other person talking, and help them reach something fresh. Then they turn the question back to me:“What about you?”Suddenly, I feel caught off guard. I stumble over my answer, become more aware of myself, and sometimes feel a little embarrassed.You’d think that at age 36 I would be an effective communicator.I’ve studied Gestalt Therapy. I’ve been a <a href="
Two Stories About Absolute Focus (opens the original)
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In my recent interview with Will Mannon, he shared the Carl Jung quote:“Every day the world will ask you who you are, and if you don’t tell them, they will tell you.”Every day the world provides us with more options. The crowd, enhanced by likes, metrics and algorithms tell you want you should care about, which is really what they want you to care about… I’ve been thinking lately about self-definition. If we were to invert this
One Size Fits None: Why Most Advice Fails (opens the original)
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Years ago, a mentor of mine, an old European VC, told me a story about the CEO of a major Korean public company.Once a year, the executives would fly out to meet him. He would gather everyone in a circle and walk around the room, speaking to each person individually.With the first executive, he spoke softly and slowly while shaking his hand.Then he moved to the next person and started yelling at him and berating him.With the next person, he was laughing and patting him on the back.He kept moving
How Founders Over-Optimize and Miss Their Real Problems (opens the original)
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Hey, I’m David. I help founders find the hidden value beneath the obvious problem.I was listening to a conversation with Diana Chapman recently. She regularly comments on something you’re might familiar with if you’ve spent any time in personal development circles: the drama triangle. If you haven’t checked it out, it’s worth the time.The drama triangle has three roles: Persecutor, Victim, Rescuer. For example, the Victim would say “My co-founder let
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