Caffeine with David

Caffeine with David

Learn how your favorite creators are building a brand and community around who they are. This podcast is hosted David Sherry, Founder of Death to Stock and Community organizer of Jacuzzi Club.

Episodes

June 5, 2025 7 mins

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 t...

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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, includi...

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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 ...

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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 questions rather tha...

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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 ways I think about cre...

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April 29, 2025 8 mins

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 idea, saying t...

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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 time was any differen...

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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’m paying attention ...

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April 17, 2025 8 mins

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 always give you what yo...

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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 skills of anyone I’ve e...

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April 10, 2025 8 mins

What if your best creative ideas show up when you let go and disappear into your work?

I’ve been testing a new approach to writing, thanks to my work with the amazing writing coach and friend Azul Torronez.

It feels entirely different. I let the writing come through me rather than forcing myself to come up with ideas. I sit down to write with no preconceived plan, and as I write I explore what’s on my mind. When I do...

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You're always starting something new in business, or testing new waters. You did it before, you can do it again.

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What do you do when you've changed, but your business remains the same? Time to evolve..

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April 1, 2025 9 mins

“I’m always telling myself that things will be easier ‘once I get through this next phase’—but that phase never ends.”

When I ask you, “How are you doing?” I don’t mean as a founder. I mean as a person. Often, those two selves give very different answers.

The entrepreneur might say they’re making major decisions, hiring, pivoting, scaling.
The person might say they’re exhausted. That they feel like they should be ...

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March 27, 2025 8 mins

Productivity is a byproduct.

The most productive people you know aren’t focused on systems and hacks.

They are driven, energized, and enthusiastic.

They do a lot all of the time without really thinking about productivity. They make tweaks here or there to enjoy themselves more. 

Productivity hacks are what we use when we don’t have intrinsic motivation. 

Productivity is obligatory and external.

The soul’s pursuit...

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March 25, 2025 7 mins

Delegation is a challenge for many entrepreneurs. 

You either:

  • Struggle to figure out what work to hand off.
  • Have a ton of work but don’t know how to communicate what needs to get done.
  • Or (less talked about) even feel a little guilty about giving work to someone else...

Delegation, when done right, isn’t a burden—it’s an opportunity to align your team with the highest-impact work.

1. The Telescope Approach: Start big p...

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    If you’ve ever felt stuck, frustrated, or like you're spinning your wheels despite putting in effort, this might be what's happening beneath the surface….

    You might rationally know what you want—whether it’s raising your prices as a freelancer, launching a new project, or taking a big step forward.

    But despite your conscious desire, something always seems just out of reach…

    The way to recognize subconscious resistanc...

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    The idea that one day your business will be "stable" and free from uncertainty is a myth. Markets shift, customers change, and what worked yesterday won’t necessarily work tomorrow. There is no finish line where you finally “made it” and get to stop adapting.

    The real safety net? Trusting yourself to respond.

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    Instead of forcing yourself to fit into an old model, it’s time to evolve your business to fit YOU.

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    I remember having a phone call with Paul Jarvis (Author/Creator) and we were talking about his newsletter, which I was an avid reader of. I told him how much I was impressed by his consistency and quality.

    “Oh,” he said. “I just spend a few days at the beginning of the quarter writing and scheduling about 3-4 months’ worth of emails.”

    “You can do that?!” I asked.

    For Paul, his workflow meant batching and sched...

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