Artisanal Concatenations of Sentient Emanations

Twas the night before Christmas and everyone is drinking,

Sorrowful, or celebrating, but done with the thinking.

Whether happy or filled with existential dread,

2025 has you all seeing red.

The games industry layoffs are finally slowing.

And the effects on releases are totally showing.

“AAA” games have put one “A” for sale.

Because “AA” games are less likely to fail.

The wars around the world are still filled with hysteria,

Nobody knows what will happen in Syria.

How dark must things be for there to be an urge

For the first health insurance CEO Purge.

The renters keep renting, the owners keep owning,

The kids these days have reasons for groaning.

Our AI overlords have not yet arrived,

And Web3 and VR, none of which have thrived.

Webstores, at least, are making a dent,

In the platforms and their outrageous thirty percent.

“The next big thing?” Feels like ashes and dregs,

Nobody cares, we’re just trying to buy eggs.

So with twenty-twenty-four finally expiring,

I wish I could say something great and inspiring.

Instead hoist up your whiskey, your wine, or your beer,

And have a merry christmas and happy new year!

So here we are on the final approach to 2025. November is halfway over, people are safely strapped into their seats, and the landing gear is lowered. It has been a wild ride for many. I am thinking about my holiday poem and whether or not I can keep the politics of 2024 out of it. Is that a fool’s errand? I don’t know yet. The muse has not yet struck.

I am staring at 11 Post-it notes on my monitor, at least one of which has been there for two years. I am also four years into writing my blog and slowly concluding that I will not add more blog article topics to the list.

That’s right. My weekly writing exercise is coming to an end soon.

There are several reasons why I write my blog.

I wanted to catalog many moments in my life and document the decision points for other people on parallel journeys.

I wanted a written body of work to help demonstrate value as a future mentor for people who wanted one.

I wanted to improve my writing skills for personal and professional purposes.

I wanted to give people who are facing a major decision or career change a body of information to contemplate so they are more informed and can confidently make the wrong choice.

I wanted to have a place where I could read about something happening in the industry, smugly rant about it, and know that at least six or seven people would read it.

There may be one or two other reasons, including the ongoing Amazon Affiliate Marketing jokes. I guess maybe I am sad I never made a hunnert dollars off of stuff that nobody would click on, and I guess everyone figured out that my stealing nickels from Jeff Bezos meant they had to spend like… ten bucks, and that is like five dollars in 2021 terms, which is more than a substack subscription, so I get it.

I just wanted to give a quick “Hey, I am going to be closing the store soon” note as I download the last articles into tHe ClOuD.

This week, I wanted to talk about habits and reporting.

If you have read any books on habits, you will understand that habit forming is hard. Some percentage of good designer success results from understanding the hacks to create a new player habit. Some percentage of them have simply borrowed the patterns from craft masters without realizing it. These two groups represent most people who don’t get fired as designers.

You must develop new habits as you enter leadership and management roles. I will not try to convince you of this; it is an absolute truth. You must develop new behaviors for thinking, collaborating, and communicating.

When thinking about the communication patterns you need to develop, you should also think about the frequency of those communication patterns. What do you need to do daily? What do you need to do weekly? What do you need to do monthly? What do you need to do quarterly?

Due to repetition, daily habits solve for themselves pretty quickly. Monthly ones are easy to put into calendars. There is nothing like Clippy popping up once a month and saying, “Hey, you need to write a report. Would you like me to help you?” with his adorable little clipart eyes blinking at you.

In my opinion, the weekly habits are the hardest to create. They are not frequent enough to be habituated easily as a matter of regular activity, and they are not so infrequent that you can outsource the habit to Outlook (or some other calendar manager) to remind you to do something. I have been trying to unpack some additional difficulties in creating weekly habits. I have not gone to brain-hacking school enough to give you a chemical understanding of what is happening.

For a growing company, this is important because you want to build in some good weekly mechanisms as soon as possible. For example, creating a weekly team status report, which helps inform progress toward longer-term goals, is an excellent habit.

In an ideal world, you should have a team lead create an end-of-week status report that can be rolled up with other team lead status reports into a departmental report. A bunch of departmental reports can be synthesized into an executive report. Depending on how many layers of management exist in your organization, two (or three or four) layers of reports get merged into a collection of reports to give the One True Report at an executive level that helps senior leadership make strategic decisions.

These reports can help you spot and debug organizational problems.

When building a company from “zero to one, “ you often skip a lot of process and organizational work. There is organizational violence in creating new companies and products that people try not to consider. Building your weekly, monthly, and quarterly habits often gets bolted onto the company in a hurry and often with very little consideration because you do not start that process until a month or six after you need it.

You should keep this in mind when starting or scaling up a company. One of the harder things you will do is figure out the right processes to enable comfortable growth and scaling.

Start by creating weekly reports. It is hard to build the habit, and people do not immediately see the value. If you do not succeed, your business will experience very painful and chaotic growth. Over the years, I have learned that some of this pain and chaos can be avoided, and weekly reporting is one of the tools to help.

See you next week!

Over many years of standing in front of strangers and exuding noises from my food intake orifice, I have refined and polished my public speaking skills. I have also gotten good reviews from audience attendees, even from presentations where I did not give away money.

Early in my presentation career, I would get feedback that I was too excited and talked too fast. I gave presentations with too many words on the slides. I also gave presentations with no words on the slides at all.

Over time, I have gotten quite good at public speaking.

At the perceived pinnacle of my craft, there is at least one thing I should do better. I am actually doing it here.

I did not set the table nicely for the presentation.

Questions like: Why are we here? What am I presenting?

Welcome to framing.

Framing in leadership conversations is about how leaders present information, context, and perspective to influence how others understand and respond to a topic or situation. 

While I could deliver the nuts and bolts on a subject, I could have answered some early questions better to get everyone into the right mindset and help them reach necessary conclusions.

Framing can help explain the history of a situation so everyone understands how we arrived here. It can also help people make sense of their takeaways. Without good framing, a post-mortem can feel blamey or accusatory. If we frame the conversation as a learning exercise, that can help people understand that we are not looking for blame or trying to beat someone up with a shovel. The goal of the post-mortem is forward-thinking so we can learn and grow.

Framing can help people relate the subject matter of a presentation to company goals or strategy and encourage them to think beyond what immediate outcomes occurred.

Framing can help people rationally consume information that might be troubling or cause anxiety.

The next time you are putting together slides for a presentation, you should ask yourself, “What framing will make this presentation more impactful?”

Cake is a disgusting mashup of flour, sugar, and at least one reasonably edible ingredient. Pie, on the other hand, provides a framework for deploying any number of super delicious ingredients inside an edible sleeve.

I love me some pie. When I was a kid, I used to sneak off and pick wild raspberries until I had a gallon pail full, and then my mom would make me the most amazing raspberry pie. You can buy “Raspberry Pi” on the internet now, but it does not taste the same.

I am not going to follow up on this with a recipe. My mom took that recipe with her to the grave. This is not that kind of blog post anyway. I cannot bake to save my life.

It can be challenging to figure out how to split equity when starting or joining a company. You want to understand the exits and your upside during a liquidity event. Another important consideration is what you bring to the table related to the company’s age. I proposed joining several small companies early on as a first engineer for between five percent and forty percent of the company. Some of this had to do with the idea’s strength, the founders’ strength, and how much money was already raised for the business.

You want meaningful equity, and you want to know that the people you work with, known as your “first team,” have your back when it comes to taking you to a liquidity event.

The journey to a liquidity event is complicated. Most people want something magical to happen in two to four years, and you are more likely to wait seven to ten years. I was in the “two to four years” misinformed camp early in my career. I know better now.

The interesting thing about equity is that it tends to change over the life of a business. Most often, your slice of equity will get smaller. When this happens, you have to ask yourself if the business’s overall value will go up based on the change in equity. If the business value increases, then the dilution is worth it.

Sometimes, you will also find people who do not want their equity stake to evolve. This might relate to the amount of equity needed to control the company or to their perception of their own value and the relative worth of the business.

This is often boiled down to the question:

“Which is better: Bigger piece or bigger pie?”

If you have a scalable business or investors who believe you have a scalable business, you will probably fall into the “Bigger pie” camp. If you have taken venture capital, this is a pretty natural evolution. You raise some seed money, then a series A, then a series of additional rounds B through E, to either make a run to the IPO border or to be acquired somewhere in the middle of that run for a good return for the investors.

You should keep as much equity as possible if you have a small business. You will want to scrutinize the people you bring into your cap table carefully and be sure not to fall into the minority of your own company. If you want to read a tragic version of this story, Gary Gygax, one of the creators of Dungeons & Dragons, lost control of TSR, Inc. this way. You can read about that in Slaying the Dragon.

So which is better? Bigger piece or bigger pie?

It is hard to give a definitive answer.

There are some times when you will want to keep a bigger slice. It is worth examining these opportunities carefully to ensure you are not falling into a scarcity mindset trap or that keeping the equity levels where they legitimately make sense.

There are other times when you will want to create a bigger pie. When you raise money, your investors will want to own more of your company as a condition of increasing investment rounds. You should also grant some equity to advisors or key staff who want to accompany you on your journey. You should be careful about the equity levels you grant and what time frame you grant them. Having advisors with high equity levels or former founders who also have high equity levels, you might risk having a confusing cap table that will inhibit future investment.

In many cases, the right answer is not clear. You might not know whether or not you made the right decision about “bigger piece or bigger pie” until it is too late.

Are you faced with this decision today?

As someone who has been through many equity-related decisions, I am happy to have a courtesy conversation with you and give you my perspective.

We are a little late this week for a plethora of reasons. A plethora. What a great word. Stand up and say it out loud: “Plethora.” Hopefully, you are somewhere where that is quite strange, and you should nod to everyone around you and tell them, “Think about it.”

One of my writing goals is to discuss the mistakes I have made in my career, even if I do not want to admit to myself that they were mistakes. 2001 to 2006 contained a lot of deep, deep learning, which is a fancy way to say, “mistakes so big, you can see them from space.” For example, many dark things occurred at Digital Chocolate, and my actions required many people to proclaim “shenanigans!” The directionality of my actions, if not the actual actions themselves, was still reasonably correct. This is a series of confession booth conversations that still need to happen. For the record, I have apologized to the CEO for the worst parts of my conduct, even if there were people between him and me that I still think deserve prison time.

I will not serve up the rest of the red meat slash hot goss from 2004 here.

Today, I want to talk about a more recent mistake and probably a less fatal one.

In recent memory, I was talking to my boss and CEO about a series of random tasks that showed up from a customer. The task seemed like a foul-smelling concoction of menial work and time-consuming meetings. The CEO said they would own this task and see it to completion.

“This is what I signed up for.” Was the magical declaration that followed a description of the banality of the task.

This is a very important statement. In leadership, you have to understand what you have signed up for. In most leadership positions, an important thing to realize is that when you have some work that is not suitable for anyone else, it is your responsibility to ensure that it gets done.

At a certain level, “this is what I signed up for” becomes “this is important, and not what anyone else signed up for, and therefore it is what I signed up for.”

For most of your career, you must ask yourself, “Is this what I signed up for?” I think that modern-day work-life balance and the need to be your authentic self at work can sometimes lead people to a hard “No.” For an entire generation of managers, this can be confusing. Most Generation X leaders, for example, grew up in a work environment best described as a “toxic meritocracy.” The importance of working hard to get things done was important regardless of the craziness of the task. Everything your boss asks is what you signed up for.

This is less true today. People value their personal time and draw hard limits on forty hours a week. People look at the companies they do business with, their values, and whether or not they align with the company. “Is this what I signed up for?” is a harder question for most people today than twenty years ago and contains much more nuance.

Everyone has a different mindset here, reflected in their answers to “Is this what I signed up for?”

My failure here is incorrectly answering this question. I was preparing for an interesting, internally focused executive task and needed to pinch-hit on another more urgent customer-facing task. I asked myself, “Is this what I signed up for?” The surface answer is that I had signed up for the internally focused executive task because that aligns with my current responsibilities. This other customer-facing task is not personally more interesting or important to me. I accepted the task and worked through it, although not without its cost. On reflection, I tended to complain about it to my peers.

When you reach the executive level, you must treat the question, “Is this what I signed up for?” differently. Very differently. The business has a different meaning to you than it did as a worker-bee or even middle manager. You have duties and obligations as leadership to fulfill in pursuit of the company mission, and it is best to follow through those with some level of grace and decorum.

In the future, when you face executive tasks that do not feel like they are in your wheelhouse, you should consider whether or not you have the luxury of saying, “I did not sign up for this.”

At a certain point in your career, “Is this what I signed up for?” becomes a non-question. Everything that needs to get done is what you signed up for.

I am adding this to my list of conversations with people on the verge of executive promotion. They need to understand that what they think they signed up for is sometimes different than what they really signed up for.

See you all next week!