THE LEAFLET

September 11 2025

what to say when in doubt, the hidden cost of maintenance, housebuilding vs house party

WHAT TO SAY WHEN IN DOUBT

When you lead smart accomplished people, you can reasonably worry that you’re going to waste their time if you take the mic or the stage too much. You might set a very high bar for what you communicate. You’ll tell yourself it needs to be super smart or brand new or deeply inspiring.

Those high standards may leave you at a loss on a given Tuesday afternoon or before your next weekly / monthly all hands. It’s not bad or wrong to yield your time, now and again, and let people get back to the business at hand. But it’s a mistake, in my opinion, to withhold your voice and your take until you have an exceptional message.

When in doubt, remind your team what you’re doing, why you’re doing it, and how it’s going. More scientifically: what’s the current hypothesis you’re testing, why are you testing it, and what is the data saying so far?

Smart, agentic people will make up their own highly diverse answers to these questions when you don’t answer them consistently. (Some of them may still, even when you do answer them consistently). Under-communicating on these fronts is less efficient and less humane. People will spend unnecessary time wondering and storytelling (even just to themselves). And ambiguity usually feels bad. No need for the misallocation or the mishegas.

-eric 

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THE HIDDEN COST OF MAINTENANCE

Kevin Kelly has a great bit of advice about estimating cost. When you look at the price of an item, you should revise the sticker price up, maybe as much as 2x. This doubling accounts for the cost of maintaining, repairing, and disposing of the item. 

I’ve applied this wisdom here and there for personal, consumer purchases. I’m also finding it’s a good heuristic for operational outlays in projects.

A recent example: I’m producing a podcast and we recently recorded an episode with a professional Director of Photography (DP) using his high-end equipment - a way nicer rig than we had access to for earlier episodes.

We were excited about the quality of the footage we would get. And it does, indeed, look super nice: depth, color, crispness all sing through each frame.

What I didn’t account for was the huge size of the video files that this high-end equipment would create. It took way longer to move those files and then to package and proxy them for editing. Any mistake made in those steps took hours to correct instead of minutes. Ultimately, my collaborator and I realized we would need new cables, computers and hard drives, with more storage and faster processing, to work with footage like this. 

We made the mistake of assuming the narrow cost to acquire this valuable stuff was the total cost. We ignored the large costs to manipulate and maintain. This was a big underestimate.

Places this might show up for you, in your own venture:

• a high-priced consultant (typically, you’re paying for their advice. That doesn’t cover the implementation.) 

• enterprise software (eventually orgs have to let go of a lovingly edited google sheet for a “real” CRM, eg, but doing this too soon makes everyone’s life worse. You have to learn how to use the software, pay for a license to it, migrate your data into it, potentially hire people who specialize in it. Each of those comes at a cost, too)

• branding and marketing services (Cracker Barrel and the city of Austin will be quick to tell you that achieving your goals here takes much more than getting a pretty .pdf from your designers)

I’m not saying it’s wrong to spend on these sorts of things, or even to spend a lot on them. I am saying clarity about what it actually costs to make use of them is important before you buy.

-eric

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HOUSEBUILDING VS HOUSE PARTY

Homebuilding calls for clear specs and standardization, with tight coordination among your different specialists. In a literal sense, you have to ensure that the floor is level and free of holes. In a figurative sense, you set a floor of performance — a baseline degree of safety and code compliance that make the house viable. As the leader, you set the specific terms of creation.

With a house party, you’re bringing together a group of people to achieve something that may be far less sharply defined. You want a vibe or an experience or a memory to precipitate from this gathering. Each of those might be more satisfying to you, as host, and to your guests, if it emerges as a surprise rather than an engineered output. As the host, you set the conditions for serendipitous magic to occur.

Excellent work can occur in either mode. Different teams default to one or the other for good reasons. And exceptional teams can take on the alternate mode when the situation calls for it. Your team of engineers might literally be planning a party to celebrate a colleague or recent accomplishment. Your loosely bound team of creatives may need to snap into tight sync for response to a crisis.

In both modes, the leader-host looks into the future, sees an excellent outcome and intervenes now to set the team on the path to that outcome.

-eric

Read the rest here.

COMPELLING QUOTES

Economist Tyler Cowen on choosing endeavors based on your equanimity:

The people who hate losing should do things that are youth-weighted, and the people who have equanimity should do things that are maturity and age-weighted with compounding returns.

Former French horn player Arthur Brooks on investing yourself:

I decided to write down the three things I want for each of the people I love most and then ask: Am I investing in those things in their lives? Am I putting my time, energy, affection, expertise, and money toward the development of these assets and qualities? Am I modeling them with my own behavior? Do I need a new investment strategy?

Novelist Kurt Vonnegut on what generations want from each other:

What is it the slightly older people want from the slightly younger people? They want credit for having survived so long, and often imaginatively, under difficult conditions. Slightly younger people are intolerably stingy about giving them credit for that.

What is it the slightly younger people want from the slightly older people? More than anything, I think, they want acknowledgement, and without further ado, that they are without question women and men now. Slightly older people are intolerably stingy about making any such acknowledgement.

Keep going, keep growing,

Ben & Eric