Illustration by Rogie King

There’s a difference between being smart and being wise. Do you do things professionally and according to convention? Do you think ahead? Do you mostly make sound decisions? Can you synthesize information quickly and integrate it? If so, that’s great. You are probably smart.

You need to be smart to be a scientist but you need to be wise (probably weird too) to make a breakthrough.

You need to be smart to write an impressive poem or paint something majestic, but you need to be wise (probably weird too) to bring tears or make life-changing art.

Being yourself is inherently weird because you’re unique. It’s precisely this quality that we find appealing in exceptional companies.

Do you possess weird? Or do you follow the rules and treat business like a science?

Do you possess weird? Or do you inform your processes mostly by how others do/scale/fundraise/hire?

Does your startup possess weird? Or are your advisors mostly conventional thinkers?

Are you weird enough to be wise and wise enough to be weird? If yes, let the whacky, unconventional, zesty and courageous side of you have a space in your business and you’ll be all the better for it.


Illustration by Ryan Putnam

Your product isn’t what you think it is

A green, flowering garden is pretty. It can also take a good amount of effort to maintain. The best gardens provide beauty, fragrance—even stuff to eat—and need minimal effort to maintain.

The good stuff — the output — of the best gardens, is set up to emerge naturally. By positioning plants that make use of one another’s byproducts in proximity to one another, the gardener gets time off.

The other factor is, of course, healthy soil.

Now, the output, which can be a commodity, merchandise, some sort of desirable outcome or effect — like shade — is what is ultimately desired by us people. In a smart garden, work is done to shape the ground to catch rainwater and we invest in great soil quality. The plants don’t need us quite so much when they have a healthy system that understands them. They’ll just do their thing and grow.

In a business, our desired outcome may be a quality product, sales growth, and a team whose productivity and happiness does not depend on individualized nurture. Behind it, you need good work. No matter what your output is, the good work is the core, and the output should be set up to emerge…

… as a byproduct of the good work.

By placing your focus on the work — the real product — a desirable commercial and cultural result can emerge with greater authenticity. By viewing your business’s output as its byproduct and by putting your energies into the work, the opportunities to achieve more, more easily, will increase immeasurably.

Don’t be clever.

Illustration by the exceptional Vic Bell

A startup’s guide to making promises

Just make a human promise, and keep it. This is a sentiment Seth Godin shared with me in an email correspondence.

If you can’t keep a promise, it really doesn’t matter how cool you are or how clever you are, your idea will be detached from an authentic purpose.

A promise is the bottom-line of a product. It’s the essence, the soul of the product. It infuses the product with meaning and value.

Mistaking product for promise creates (among others) two sticky problems:

  1. Regarding your product as your promise numbs you to the essential purpose of the product. In other words, you’d be trading in a clear, company-wide view of the problem you set out to fix — your promise — for a hit-or-miss approach of trying to figure out what customers expect of the product. This is designlessness.
  2. You also may resort to a one upmanship product-design model: designing your product by mostly looking at how your competitors are designing theirs. This can dull inspiration, innovation and creativity because you’re not actually connecting to your promise. You’re connecting to someone else’s. Your promise has now shifted to “we do what our competitors do.”

I was surprised to see how easily I myself fell into this trap.

Don’t (only) be clever. Make a human promise, and keep it. Stay true to your original idea, your promise. Staying true to this adage will protect you from a confused and arbitrary creative process, and from one upmanship. Bring joy and simplicity to your customer: don’t be clever, make a human promise and keep it.

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Price for less, for less.

Doodle by david_rollyn (Instagram)

Pricing should never get you stuck, and though there are many approaches to pricing your business, I find the approach of less for less to be easier than others. At the end of the day, your support or sales staff needs to be able to sell the product and justify its virtue.

When pricing Mad Mimi, I needed to provide a compelling alternative to the dominant companies offering email marketing (Constant Contact, MailChimp, ExactTarget). This strategy of less for less not only succeeded in capturing a material segment of the email marketing space, but allowed my (at the time, small and scrappy) business to thrive with the bootstrapped resources I had available.

Here are a few general approaches to pricing:

Charging more and providing less

This approach can work if the product has a strong culture or a super-sticky design, but this is a branding and messaging tactic. It’s powerful but if not done right, this approach can expose sales staff to a troublesome sales lyrics and lack of conviction in your (high) price vs. (lesser) value vs. (lower-priced) competitors.

Charging less and providing more

I’m always suspicious that a compromise in quality for feature-richness is unavoidable with this model. Also, I don’t even know if I want more. I may just want easier or more elegant or more approachable. You don’t need to provide more and charge less to woo me. You can provide more and charge more, or provide less and charge less, but I don’t see the value in charging less and providing more unless you’re a utility company.

Justifying less for less

You may have convinced yourself: but my customers be unhappy with less features than competitors. I know how important a “search” feature is, and without that search feature, customers won’t be able to… search. Here’s the litmus-test for this concern: if the customer has that function accessible somewhere — anywhere — through a different service or context even if it’s painful, then that’s what they’ll do. They may request that feature and you may want to respond later, but they’ll like you for your minimalism and simplicity. It’s a healthy tradeoff.

Why not spin it?

Spinning a scant feature-set into a winning formula is imperative. If you perceive your scant functionality as a shortcoming, you’re working against yourself. So get you your simple, only-what-you-need-nothing-you-don’t boots on and kick sand in your bulky, oversized nemesis’ eyes. Be sure to accompany your gesture with the ability to provide an impassioned and empathetic and personal experience.

Hint: big companies have a hard time being empathetic, impassioned and personal. They have a hard time with “surprise and delight” too. You may have seem less to offer, but simplicity and empathy are important to enough people to give you enough runway to build yourself up over time as you mature.

Entering a crowded market as the little guy? Offer less and you might win.

Illustrated by Shimon Angel, animated by Ofer Winter

Entering a crowded marketplace can be a little daunting — okay, a lot daunting — if you’re smaller, way smaller than the dominant players.

I get emails from time to time, mostly around this question. When I started Mad Mimi (see TechCrunch), I raised $100k — that’s it — and disrupted both MailChimp and Constant Contact to gain both materially higher NPS, robust revenues and more importantly, considerable traction. But how? By offering less.

Q: Can I beat the competition by having better design, better UX?

A: Good design and UX is always a good thing but only effective when used to ice a cake — and not to apply lipstick to a pig. So, the answer is no. This is an incomplete competitive advantage.

Q: Can I beat the competition by offering more features?

A: Most dominant technologies are already mature, which can be defined by being feature-rich. A rich feature-set is best done over a long time if you’re scrappy or in a blitz if you’re rich. Rich features though are almost always better than being feature-rich. This lets you focus on the most important customer-problems without being distracted by a broad set of features. If you’re ever managed a broad feature-set, you already know how annoying it is. Answer: probably not.

Q: Can I beat the competition by offering less features?

A: Now you’re talking! By offering less features, you give yourself two things: 1. you opt-out of the one-upping cold-war (as described by Jason Fried in Getting Real) and 2. you force yourself to offer simplicity as a value. Simplicity is one thing your big bloated competitor may have trouble with because they’re so “mature”. Maturity inevitably brings complexity. Infancy is bliss in this regard. Answer: probably.

Q: So if I offer less, how can I convince others to consider my product?

A: Less isn’t less-is-less, it’s less-is-simpler-is-better-is-liberating. This is where your good design and UX comes in. Less, combined with simple combined with killer design is the secret weapon of the scrappy startup. But there’s a final detail that will make or break everything…

You need to make a human promise, and keep it. This is from a conversation I had with Seth Godin. Superb advice.

If you’re not actually solving a problem, if you’re not actually providing value, your design, your UX, your charm and marketing, may be lipstick.

Comments welcome! Favorite this article please.

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The essential idea-companion: How to Make a Task Model

Illustration by Gemma Correl

Ideas are easy.

Execution is tricky.

You’ll know a good idea when it feels simple to articulate.

You’ll know a less-good idea when it feels complicated to articulate.

Now, to build a system, you need fine builders.

It’s easier to recruit those fine builders with an achievable plan that makes their tasks clear. Think of this as a task model.

The task model

The diagram below shows three sets of “cards.” It’s an architecture template that you can do yourself at home using nothing more than some paper — or better, cards — and a pen or marker.


The activity.

The customer performs activities. The builder performs tasks. What do your customers need your help with? What are the problems you’re solving for them? These are activities.

Being frugal when deciding your initial customer-activities is the key to good execution. Narrowing your idea is an artform. It’s neither easy or simple, and requires a lot of letting go.


The task.

An achievable task model depends on having a small number of activities. There are many tasks associated with a single activity, and the more tasks you include, the more clear the work-ahead becomes. Tasks inform the us of the size and complexity of the project.

Subtask or task details

The subtask and the details.

To properly estimate the scope, the cost and the timeline of your project, spending some quality time mapping out subtasks or details will serve you well. Subtasks and task details help avoid confusion, enable builders to make better granular decisions and better comprehend what’s required of them.

Don’t try to simplify your tasks. Throw in everything you think of in a stream-of-consciousness. Tasks are like cash — another dollar doesn’t hurt — so don’t be sparing, but do be sparing by the activities. Highly-constrained activities will result in manageable tasks. Unconstrained activities will result in unmanageable tasks.

A task model is the first step to making your any idea manifest. It’s a technique used by many of the smartest people in software and it’s drop-dead simple to do yourself.


Customer’s problems are mapped to activities. The system’s responsibilities are mapped to tasks. Subtasks help those building the system have more clarity and make better decisions.

I’ll share more on story mapping and ultra-fun card mapping in my next article.


Jeff Patton’s book User Story Mapping is indispensable if you’re serious about getting deeper into story mapping and task modeling.