Brittleness comes from “One Thing”

We’re tired of hearing how small software companies usually fails.

The data show that the two most common causes are (1) the product just isn’t useful to enough people and (2) problems with the team.

But what about the cohort that dies even though it did sell some copies of software to a few people, and where the founding team isn’t dysfunctional?

I don’t have data for that cohort (tell me if you do!), but informally I see things like the following, which is useful to list because there’s a pattern common to each of them, which furthermore is possible to counteract

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Brittleness comes from “One Thing”

We’re tired of hearing how small software companies usually fails.

The data show that the two most common causes are (1) the product just isn’t useful to enough people and (2) problems with the team.

But what about the cohort that dies even though it did sell some copies of software to a few people, and where the founding team isn’t dysfunctional?

I don’t have data for that cohort (tell me if you do!), but informally I see things like the following, which is useful to list because there’s a pattern common to each of them, which furthermore is possible to counteract

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You can have two Big Things, but not three

No you can’t “have it all.” You can have two things, but not three.

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The fundamental lesson of the forces governing scaling startups

Idealistic founders believe they will break the mold when they scale, and not turn into a “typical big company.” By which they mean: Without stupid rules that assume employees are dumb or evil, without everything taking ten times longer than it should, without wall-to-wall meetings, without resorting to hiring anything less than the top 1% of the talent pool, and so on.

Why do they never succeed? What are the fundamental forces that transform organizations at scale?

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Strategic Activities for a Company Retreat

I happened to be sitting on the tarmac, delayed, when a tweet came in asking for some ideas for what to do on a company retreat that would be strategic.

In the confines of six square feet of personal space, I sent a few answers.

These are useful exercises any time!

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Change: Damned if you do, damned more if you don’t

Though inevitable, change is uncomfortable and exhausting. Even we who relish change, who love bragging that “it’s hard but every day is different,” reach a breaking point after years of adaptation and fake-gleefully exclaiming that “failure is how you learn!” Yeah, but all this learning is fricking tiring.

How do you manage change?

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I hate MVPs. So do your customers. Make it SLC instead.

Product teams have been repeating the MVP (Minimum Viable Product) mantra for a decade now, without re-evaluating whether it’s the right way to maximize learning while pleasing the customer.

Well, it’s not the best system. It’s selfish and it hurts customers. We don’t build MVPs at WP Engine.

This is the right way.

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Should you invent a new UX?

Using common metaphors makes your product UI identical to all the others. There’s no personality, no brand, solidifying the notion that this product is “just another tool” rather than a new way of interacting with a computer. Surely technology can be better than that.

But this is an egocentric view. Your customers don’t want to figure out some newfangled damn thing just to navigate a dialog box.

Which way is the right way?

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Finding the right advice

For every clear example that proves “X is right,” there’s another equally compelling story of success where the mantra was “X is wrong.”

So the question is: Which advice is right for me?

Let’s answer that question.

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Satisficing vs Maximizing

“Maximizing” means expending time and effort to ensure you’ve solved something as best as possible. It typically needs lots of exploration and analysis to ensure “the best” option hasn’t been overlooked, and that we have confidence in our evaluation of all options.

“Satisficing” means picking the first option that satisfies some given criteria. It’s less time exploring & analyzing, more time acting. It’s not getting paralyzed by the pursuit of “perfect,” but it often doesn’t result in finding the very best.

In software and startups we can choose when we maximize, and when we satisfice. It might seem like maximizing is best especially when you have teams of smart people who can do the maximizing. But not necessarily.

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Not sure?

Whenever you’re dithering, usually the correct answer is the difficult one. The reason you’re dithering isn’t that you’re unsure. It’s that you don’t like the truth, so your emotions are trying to justify the easier path.

But your job is to do the difficult thing.

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Avoiding the trap of low-knowledge, high-confidence theories

There’s an underlying mechanism that causes us to be falsely confident in our command of knowledge and decision-making. We automatically construct narratives of comprehension, even when our command of the facts is feeble.

Defeating this requires intentional effort.

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The wrong question: Is now the right time to start a company?

The answer to that question is “yes,” but that’s why it’s the wrong question.

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