Hidden Value with David Sherry

David Sherry
  • 4.5 (22)
  • BUSINESS
  • UPDATED BIWEEKLY

Step inside real founder conversations: raw, unrehearsed, and honest. No playbook. No polish. Just ambitious entrepreneurs uncovering the answers that were there all along. Because every business hides something valuable trapped under the weight of success and chaos of growth. The Hidden Value podcast is hosted by David Sherry. David works with early-stage founders to grow professionally and personally. He founded, sold, and advises Death to Stock – a media company and newsletter that serves brands like Unfold, Figma, and Spotify.

  1. NOV 13

    “Do I grow this business, or will that cost me my freedom?”

    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 upside, and if so, what does that cost him? In this conversation, we uncover the tension beneath that question: the pull toward growth and challenge on one side, and the desire to protect freedom, flexibility, and a life he actually enjoys on the other. Together, we explore how to move beyond rigid either/or thinking and into reversible experiments that generate real information instead of endless planning. Because whether you’re a founder, consultant, or creator, most big business decisions don’t get solved by more thinking. They get solved by taking the next small step, seeing how it feels, and letting that experience guide what comes next.

    27 min

  2. NOV 6

    "I help founders tell their story, so why am I struggling to tell my own?"

    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 that question: the difference between marketing a company and marketing the founder behind it. Together, they explore how the recognition and visibility comes from the story only you can tell. Because whether you’re a founder, creator, or consultant, the hardest story to tell is often your own. But that’s where your unique value lives.

    27 min

  3. OCT 30

    "I helped build products at scale, so why does smaller suddenly feel bigger?"

    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 relational impact and Main Street business ventures. We uncover how Cris is leveraging her experiences to build a legacy that truly resonates with her values.

    23 min

  4. OCT 23

    "My education program is ready to launch, so why can't I tell people about it?"

    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 meaningful conversations. The discussion covers personal experiences, strategies for validating ideas, monetization, and overcoming the fear of rejection when presenting a new concept. Join us as we dive deep into creating impactful learning experiences and the entrepreneurial steps involved in making a significant societal contribution. Chapters 00:00 Introduction and Setting the Stage 00:17 Reflecting on Personal and Educational Journey 01:14 Transitioning from Personal to Professional Goals 01:52 Exploring Business Opportunities and Challenges 02:32 Strategies for Engaging Potential Clients 03:42 Understanding the Market and Client Needs 04:54 Overcoming Personal Barriers to Business Conversations 06:45 Developing a Business Model and Pricing Strategy 09:03 Executing the Plan and Seeking Feedback 19:00 Final Thoughts and Encouragement

    20 min

  5. OCT 16

    Scaling a Hybrid Community: From Coworking Growth to Digital Leverage | Hidden Value

    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 unpack how sequencing, delegation, and education can unlock new levels of scale—without taking on unnecessary risk. Charlie shares how he’s reframing growth from “open another space” to “build digital leverage”, and why his sweet spot lies in teaching founders how to find and validate ideas through smart market research. Key Takeaways • A hybrid model can leverage the best of online and offline communities. • Scaling a physical business requires different strategies than scaling digital. • Educational content creates scalable, de-risked growth opportunities. • Market research should come before user research when validating ideas. • Finding your “sweet spot” means aligning business potential, customer need, and personal excitement.

    19 min

  6. OCT 9

    Finding Alignment: The Journey from Corporate to Personal Fulfillment | Hidden Value

    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 double-edged sword — it can both empower and intimidate.Aligning inner values with outer expression builds authentic leadership.Transitioning from corporate to personal work takes courage and experimentation.Being seen and being perceived are not the same thing.Redefining success on your own terms leads to fulfillment.Chapters 00:00 – Exploring Visibility and Authenticity 01:56 – Transitioning from Corporate to Personal Paths 05:04 – Balancing Public and Private Selves 07:04 – Aligning Internal and External Values 09:10 – Embracing Authenticity in Professional Spaces 11:51 – Redefining Success on Personal Terms 13:57 – The Power of Being Seen 17:12 – Navigating Professional Growth 19:39 – The Journey to Personal Fulfillment 26:53 – The Courage to Be Seen Credits & Links Host: David Sherry Guest: Saara Lampwalla

    32 min

  7. JUN 5

    The CEO ‘Clean Your Desk’ Method to Unblock Your Energy

    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 live. They can’t decide if they should quit their job or leave a relationship. They seem to be caught oscillating between these decisions, never moving forward. The good news is that if you can start to make progress in one area, you can start to make progress in many. All it takes is a little momentum, and suddenly the damn will burst. If you aren’t feeling like you’re making progress, the good news is the worse it gets, the more likely that it will get painful enough to break the tension. Tension is what you feel when you get pulled forward and backward or left and right with no progress. The trick that’s being played on you is that you think it’s about deciding. Being so focused on a decision, such as “Should I quit my job or not?” Or “Should we break up or not?” Is actually the wrong focus. It’s not the decision that is the problem, it’s something deeper which is preventing you from trusting yourself and hearing yourself enough to make natural decisions that move your life forward without so much effort, thinking, overplaying, and pain. What we’re really talking about here is our energy, and whether or not it is flowing or whether or not it is trapped and stagnant. We stop our own energy from flowing, and that keeps us stuck. The trick to breaking the damn is to get your energy flowing again, and that involves trust. Trust is needed to move forward, because decisions we feel are important require us to take a leap into something unknown. No matter how much you want to predict your future, or how much you think you can even project the future, you can’t. Ultimately it takes a leap of faith to move forward. The good news is you can start small. You can domino small decisions into larger ones. What’s one thing that has been put off due to your inability to decide or take action? What’s one small thing you can clear from your backlog? A client of mine, a CEO of a $30M+ company, he realized that he was prone to letting his metaphorical “Desk” get messy. It was so messy with so many problems and decisions and moments of not saying how he truly felt that it was covered with so much it was hard to work. The trick was to start clearing his desk. One thing at a time until he finally started to get some space again. Then, in the future, it was about being proactive enough to clear things before they became a problem for him. Your energy unlocks when you let tiny decisions compound into bigger ones, and when you let your energy flow instead of stopping it by trying to predict and protect yourself from the unknown.

    7 min

  8. JUN 5

    When Fear Hijacks Your Intuition: Making the Right Decisions for Your Business

    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 successful entrepreneurs, including a real-life example of a challenging executive hire decision. Watch now to gain clarity on making the right choices for personal and business growth.

    6 min
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4.5
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22 Ratings

About

Step inside real founder conversations: raw, unrehearsed, and honest. No playbook. No polish. Just ambitious entrepreneurs uncovering the answers that were there all along. Because every business hides something valuable trapped under the weight of success and chaos of growth. The Hidden Value podcast is hosted by David Sherry. David works with early-stage founders to grow professionally and personally. He founded, sold, and advises Death to Stock – a media company and newsletter that serves brands like Unfold, Figma, and Spotify.

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