Caffeine with David

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...

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 ...

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 tha...

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...

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...

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...

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 ...

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...

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...

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...

“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 ...

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...

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...