Hidden Value with David Sherry

How to move toward what feels alive without burning down what already works.

In this episode, I talk about working like a lion as a better productivity model for an ADD-style brain. Instead of trying to graze all day, the idea is to rest deeply, work in intense bursts, use habits and rules to carry the work, and shorten the distance between idea and execution. This is a practical way to think about focus, momentum, scheduling, and founder energy.

Trade Up Your Media: Stop Infotainment & Read for Real Change The speaker discusses feeling unsatisfied by scrolling and "infotainment," which blurs information and entertainment and scatters attention with addictive but unfulfilling content. They propose a "trading up" process: choosing higher-quality media and, when possible, moving from digital to physical formats (e.g.,...

AI, Change, and Opportunity: How to Adapt Without Doing It Alone David discusses how constant change in the world creates new opportunities, even when it feels scary and demands adaptation. He notes that every day brings new businesses, books, apps, and tools, and that technological advancement often drives deflation-making once-expensive products smaller, cheaper, and more powerful-while also dis...

David Sherry explains why goal-setting often fails for entrepreneurs and how to fix it. He argues that many people set "fake" goals based on what they think they should want or what others are doing, which leads to low commitment and stalled progress; he recommends getting honest about what you truly want so you have sustainable energy to pursue it. He also warns that big, vague goals (l...

This video explains why entrepreneurship often feels like an emotional roller coaster, with highs and lows driven not just by business problems but by how founders relate to them. As businesses grow, more people and more problems appear, much of which is outside the entrepreneur's control, and fear about potential issues can amplify the stress. The core issue is tying personal identity entirel...

What many people call burnout is often deeper misalignment: as you change over time, your current job, relationship, hobby, or identity may stop feeling resonant, leading to boredom, masking your true feelings, and a growing tension between how you feel and the story you've held about yourself. The speaker describes this as a metamorphosis process where withdrawing, coasting, and conserving en...

Many founders wrongly chase "freedom," entrepreneurship can reduce freedom as success grows and that a life with no responsibilities can lead to depression; instead, real freedom is choosing which responsibilities to take on. To build alignment, they recommend reflect on meetings and activities, tracking how they felt, and using the past to plan the future by pursuing what consistently b...

In this Hidden Value session, Tanya Moushi and I explore the themes of creativity, freedom, and the complexities of personal and professional responsibilities. Tanya shares her struggles with creative paralysis and the desire to compose music, while I encourage her to prioritize her desires and define what freedom means to her. We discuss the importance of intentional planning, the weight of famil...

Andrew Fink left a stable career in management consulting to build a solo writing practice helping founders turn their ideas into newsletters, LinkedIn content, and now even books. His business is working. He makes a good living, has freedom to travel, train for races, and design his days. But lately, he’s been wrestling with a big question: should he grow this into an agency for more financial up...

Mohammad Khan helps deep tech founders make their complex ideas understandable and compelling. But lately, he’s been facing the same challenge he solves for others: how to articulate the unique value of his own work. When AI can write copy and marketing teams can polish messaging, where does his kind of storytelling fit? In this conversation, Mohammad and David uncover the real tension beneath tha...

In this episode, I sit down with Cris Valerio, a former journalist turned tech innovator, as she shares her career journey from the newsrooms of New York City to the tech scene of Silicon Valley. Cris opens up about her midlife transition into entrepreneurship, driven by a desire to create meaningful impact beyond the corporate ladder. We explore how she's redefining success by focusing on relatio...

In this Hidden Value session, David sits down with Latham to explore his journey from engaging in the education of his child through homeschooling to aspiring to turn his insights and experiences into a community-centric business. Latham shares his passion for education, the challenges of transitioning his ideas into a business, and the importance of understanding his potential market through mean...

When Charlie Ward built Ramen Club (an online community for SaaS founders) and Ramen Space (a physical coworking hub in London), he found himself running two thriving but different businesses—one online, one offline. In this Hidden Value conversation, David Sherry and Charlie explore what it takes to scale a hybrid business model, balancing physical operations with digital growth. Together, they u...

When Saara Lampwalla left her corporate role to build something of her own, she entered a season defined by visibility, vulnerability, and the courage to be seen in a new light. In this episode, David and Saara explore what it means to align your inner values with how you show up in the world — and how that alignment shapes both your fulfillment and your freedom. Key Takeaways Visibility is a doub...

I spoke with someone recently who was *really* stuck. I’ll call him Joe. Joe was not just stuck professionally, but with his relationship (on again off again) and with his work (not sure if he should change careers or Not just professionally. When some people get stuck.. they get really… really… stuck. They find that multiple areas of their life start to feel stagnant. They can’t choose where to l...

Join David Sherry in this episode of Founder Therapy as he discusses the crucial distinction between intuition and fear in decision-making. Learn how to recognize whether your decisions are driven by genuine intuition or by underlying fear, and discover strategies to navigate discomfort when stepping into unknown territories. David shares practical insights from his experience working with success...

One of our earliest photographers at Death to Stock was Patrick Chin . Patrick had built a business in the luxury hotel and fine dining space. This meant that Patrick had to fly around to take photos at beautiful beachside hotels, or snap images of Michelin star Chef’s beautiful creations…getting to taste the dishes afterwards.  Poor Patrick. Patrick showed me that who you choose as your customers...

One of the compliments I receive most often in my work is something along the lines of: “You ask such great questions.” This probably comes after I ask someone some questions that I’m curious about. You get better at asking questions when you begin seeing them as a tool to have better and more valuable conversations. Questions set the frame of the discussion, and so leading someone is often about...

“ What are the levers that I can pull that are going to help me create more value?” Say you want to charge more, be more known, get better testimonials, get more respect from others… the simplest pathway is to expand the value you create for others. Value creation is often thought of as a skillset, but what if how you think about value shifts your potential for creating more of it?  Here are some...

Creating Streaks Streaks have always been helpful to me, building a chain of habits that help you see your own progress. For entrepreneurs, they are especially important because it’s so easy to feel like you aren’t making progress. Many entrepreneurs tell me,  “I get to the end of the day and it feels like the scoreboard is reset to zero.”  Yikes . Jerry Seinfeld was always a big proponent of this...

Time to “Buckle Down” I was talking to a client today, and we discussed the opportunity to resolve a major problem in their business that needed attention.  The tone of the team and the discussion centered around the idea that now was the time for them to “Buckle down, get to work, roll up their sleeves, and make sacrifices for a little while to resolve the issue.” I questioned the idea that this...

When I talk with clients, there’s always a dance – where is this conversation most exciting for them? Where is my excitement? What is productive? Where are we going? I notice the subtle ways in which my body opens up, or closes down, how certain topics create constriction in me or the other person.  This type of awareness can itself be draining; rather than being fully relaxed in a conversation, I...

People launch businesses for wildly different reasons… Escape the corporate life Make a lot of money Create a meaningful product or service Have flexibility in daily life Build relationships and be seen They’re chasing something that they believe that business, as a vehicle, can give them. But once you're in the midst of creating the business or doing the new type of work, you realize it might not...

What opportunities do you have for creating more connection in your life? A big theme of mine this year is exploring connection – how we connect with others, how we open up to connection, and what forms of communication lead to connection. I became more seriously interested in this area of my life after spending a week in Costa Rica with a group of people with the highest quality communication ski...