Hidden Value with David Sherry

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.

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.

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

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.

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

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.

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.

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 matters. And that if you’re going to choose someone to serve, choose someone great.

I had another friend who was a photographer for new startup retail businesses. They had very little money, fast turnaround times, and often burned through the images quickly. This other friend was constantly struggling with business and was frustrated. 

Given that you can choose your customers, who are the best customers worth choosing?

One of the compliments I receive most often in my work is something along the lines of:

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 questions rather than making statements. Questions can be used for a variety of different purposes. Today I wanted to outline 5-levels of value oriented by particular questions that people ask of me and ask themselves. 

If you want to create/expand value, ask questions higher up the ladder.

The Value Ladder: 5-Levels of Questions for Leaders

1. “What do I do?”

When you are working in a new role you’ve never been in before, you get tripped up on the question “What do I do next?” When you don’t know what to do, you don’t act. And so you wait or search for someone or something that can tell you what to do. Most often, this is a way of procrastination. You can’t act until you clearly see a specific, short-term step and action you can take. What do I do is the lowest leverage and least valuable question to ask of yourself or others. But it is often the place we start.

2. “How do I do it?”

Many people take similar actions, but not all get the same results. Why? When you don’t understand the “why” behind how something works, you lack proper form. Form is “how” you do something. “How” is a question about form. 

How helps get you to feel/experience the action rather than intellectually understanding it. How is for practitioners seeking to learn how to apply something they’ve learned. How is for doers… in an organization, team, community, or political structure. “How” is, relatively low value. Often, to succeed with how, you sell something at lower price points and therefore must have a large audience.

This is why “how” is the most prevalent form of content on Youtube, for example. “How” is also the easiest question to waste your time on. “How” is a great game of telephone. You read someone else’s “how” and translate it poorly to your own situation and then get frustrated by not getting the right results.

3. “Who?”

When you wake up to the limits of your own “doing” you begin to see the benefit of collaboration, hiring, delegation and managing and leading a team.

Who is the first leadership question outside of self-leadership. Who is the shift from Founder-Doer to CEO-Manager, from actor to recruiter. Who marks the beginning of systems-level questions. Before you get to “who” you focus on your input into the system.

When CEO’s come to me with struggles for their personal productivity, I often take them out of “how” questions and into “who” questions. I’m less interested in them and more in the teams and systems that support them.

4. “Where should we go?”

Systems need direction. “Where?” charts the course. “Where” is about the future, whereas the previous questions are more about the present. Where questions are about owning the responsibility of taking people into the unkown. If organizations don’t know where they are going, then everyone is working out of sync and unison. Where is one of the greatest possible filter questions because it completely changes the course of a company or team. 

Change the where, change everything. A where question for Kodak Cameras was: “Double down on Film, or Enter the Digital Camera Space?” A question for NASA is: “Moon or Mars next?” As you can see, asking “Where” is risky. This is why “Where” is the CEO's question. With “Where?” there are consequences, or regret. Aligns a system to a destination, puts resources on the line, and creates definitive direction.

The trick of understanding organizations, communities, and political parties is that they crave direction. They ask, “Where are we going…together?”

5. “What does it mean?”

The final level of value is in meaning questions. When you’re so distracted by the doing of things, you try to ignore lives deeper questions around meaning or meaninglessness.

The good news is that we are meaning-making machines. Meaning making is about how we interpret the events around us, and how we contextualize every other question listed above. The highest levels are about context.

In meaning questions, you are playing with the container, not the contained. You start playing with the rules, the stadium, the field, not the game or players on the field. You start working on the museum rather than the art sitting in it. Meaning is about creating context, and context is how we come to understand ourselves and the world. Context creators, meaning makers are storytellers. This is why Steve Jobs didn’t say, “The most powerful person in the world is the doer, the creator.” 

He said,

“The most powerful person in the world is the storyteller.”

Stories write and create invisible scripts and lines of action. Leaders working at this deeper level are playing a more invisible game of power and creation that comes from generating systems without being stuck inside of them. These leaders allow, encourage, and generate the success of others without being seen or heard.

“A leader is best when people barely know he exists, when his work is done, his aim fulfilled, they will say: we did it ourselves.” Lao Tzu

These inventors challenge our current frame of reality. They see outside of the container. If Tom’s Shoes invents “Buy one pair of shoes, donate one pair of shoes” as a way of making our consumption, and then other companies follow suit, eventually forgetting the original creator of such an idea or protocol. Tom created new meaning.

Climb the Ladder of Your Own Questions

The next time you feel stuck, I want to offer a little challenge:
Don’t immediately look for a better answer.

Ask:

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 ways I think about creating more value…

1. Make Their Vision Bigger

When I meet with a client for the first time, my gut reaction is often to ask, 

“Are they thinking too small?”

They might say they want to launch in one market, and I’ll ask, 

“What would it look like to launch in five markets this year?”

Thinking bigger increases excitement for projects. You want to increase excitement only to the point of slight impossibility so that the discomfort isn’t too strong. 

We’re not here to merely make happen what is expected, we’re here to help make the unexpected occur. In teams, 2+2 = 4, or 6 or beyond. That is the beauty of working with others.

Each person adds new capability, new insight, or possibility. Even if you’re an employee, thinking this way can expand the value you bring to whoever you work with. You’re not always going to follow through on every huge idea you propose, but at least you’re expanding the potential reality you can help create.

You want to move beyond assumed value or possibility for how well things can go, and contribute your part to create a greater whole. 

2. Multiply Value by Overdelivering

People say, “Charge what you’re worth.” 

I say: “Overdeliver on the project significantly beyond what you charge.”

Whenever possible, you want to add to the “multiple” of value someone receives when working with you. In an ideal world, customers should get 2x-5x+ of the value that they’ve paid. Skewing value in the favor of your customer creates an abundance loop. 

Ask yourself, “How can I overdeliver on this project?”

 It might be sending your clients extra resources or even something as simple as remembering birthdays and sending a quick message. 

Some examples…

• Send monthly progress recaps, highlight new opportunities that weren’t previously seen. 
• Offer bonus calls to brainstorm and problem-solve.
• Connect your customer to people you know who can also help them. 
• Share mini “toolkits” of templates, how-to guides, etc. with clients.

3. Stay Focused on Transformative Change

Great products create transformative change. They transcend beyond what someone “wants” and explore and expand into what someone needs, dreams of, and has never considered before. 

If you do only what your customer wants you to do, you are creating products based on a view of the world with limited knowledge. The benefit of expertise and mastery is your ability to see significantly more than others in a particular area or subject. 

It’s hard to say “no” to someone. Doing so, though, create the ability to guide and lead someone through a process that they might not have been able to previously imagine or understand. 

When you hire a travel agent, you don’t want to just tell them what to do and have them book it for you. You want them to think of what you never thought of, make decisions you might not immediately understand, and recommend what you would never find yourself. 

Steve Jobs knew, simply, that people wanted to buy the latest CD player, and yet he said no so that he could create something much greater with his iPod.

Creating more value isn’t about just having the skills to do so – it’s often understanding what’s possible, having and building confidence to deliver, and being willing to explore unknown territories that may feel uncomfortable at first but help you expand what’s possible for yourself and others.

What mindset helps you stay focused on creating more value for others? Or what have you done as a habit that has helped you?