Ready, Fire, Aim vs. Thoughtfulness

Part of the joy of entrepreneurship is that, as an entrepreneur, you get to start fresh with each new project.

If you work for a large corporation, legacy technologies, organizational rules, middle managers, etc. will always provide the framework in which you make stuff. Whereas in a startup, if you’re a founder, you help create the framework in which stuff gets made. (And you also get to make stuff within that framework.)

In reality, during each start-up’s lifecycle, as an entrepreneur you make hundreds and thousands of “mistakes” (learning experiences). If you’re not an idiot, you will notice some patterns.

Certain pain points rear their ugly head repeatedly. Some of these pain points are unavoidable (dealing with your local governments’ regulatory and taxation agencies). Other times, the pain points are avoidable, as they are artifacts of the framework you created.

Most startups fail before they’ve ever launched. That is to say, the potential founder decides not to risk anything. He tells a friend about his big idea… and that’s the end of it. Or, the project is launched, but the founder doesn’t really invest in doing the activities that she intuitively (sometimes subconsciously) knows are a prerequisite for success.

Which is why I’ve always subscribed to the DIFN School of Web Entrepreneurship. If you’ve not ever read the Hall of Fame-worthy original DIFN article at, click here to do so now. The gist of it is this: you already know the core activities which drive the growth of your business. So get off of Facebook, and go do those core activities. Stop procrastinating.

Another favorite phrase of mine is, “The perfect is the enemy of the good.” Because perfect never arrives, “waiting for perfect” is a great excuse to procrastinate. If you remove the excuse, you can remove the procrastination. You have a great idea? Cool! Not really, though. Go push a beta live in 48 hours. Or at least finish your alpha, or demo… now I’m interested.

These maxims have generally served me well in the past. Ready, Fire, Aim! Your initial business or product plan will evolve dramatically anyway. So don’t worry about getting it perfect. To learn, you must do. To build 1M in annual revenue, you must first sell your sucky v1.0 widget to a single customer for a tiny amount of money.

My practical experience tells me that Ready Fire Aim, The Perfect Is the Enemy of the Good and DIFN are proven shorthands to launch a startup, then get it to break-even and beyond. Which means they are powerful strategies indeed; getting materially past the “try to survive stage” places you and your business in the top 10%. I’ve found these maxims are especially integral to success in years one and two of the start-up lifecycle.

Groundhog Day


This guy…

The pain points of these philosophies really emerge in year three. We need some design changes on our Web site. OK, but that change which should take 10 minutes, is going to take 2 hours, because the CSS is hard to edit. Why is the CSS hard to edit? Well, we used that WordPress theme you liked in 2011, then custom-hacked it a bit to do what we wanted. Over time, our custom-hacking and new site features have made our theme into an unmanageable Leviathan. OK, well why don’t we start fresh with a new and better WordPress theme? If we install a new theme, 90% of our site will break, because most of our custom tools are heavily integrated with the old theme. Also, we had to use a lot of in-line CSS in these one-off tools to get stuff working correctly. All that in-line CSS will break, too. Well, why didn’t we think of this two years ago? Two years ago we were trying to build revenue as fast as we could, so we could break even before we ran out of runway. You told me to make the site look good, and have the design ready to launch within 14 days. We should fire the CEO. You’re the CEO. Crap.

The above conversation is one I’ve had four different times, with four different developers, at four different start-ups. Two of those start-ups made me a lot of money. Two of them lost me a medium amount of money. The common element was me, my business philosophy, and the framework setup by myself & my partners.


Does anybody else think she resembles the H&K P30? Image source:

With age comes wisdom, and — imagine me in a Yoda robe here — I’ve learned I don’t need to embrace DIFN now as my core business philosophy anymore. It’s now so internalized, so implicit, such a part of my inner self, that there isn’t a risk I will slow down too much and never “launch”. Ready Fire Aim. Trust me, I won’t be that guy who has water left in my Super-Soaker at the end of the battle.

It’s not so much that DIFN isn’t the strategy that most budding entrepreneurs need to hear — it is. My point is, DIFN is probably a prerequisite for entrpeneurial success; but it won’t necessarily lead you to the outer edges of your abilities and talents. 

Enter Thoughtfulness

My latest and “greatest” start-up, MonetizePros, is winding down (or at least going into Limp Mode) at this point in time. I don’t have any regrets about that — I don’t live that way. It didn’t pan out. I tried my best.

At the end of the month, I’m being pitched by a past business partner regarding a new start-up opportunity, about which I’m guessing I’ll be pretty excited.

Whatever project I do next, I’ve decided to commit myself — and hopefully the team of said unknown next project — to the core value of Thoughtfulness. I know, even typing that sentence made me feel like an MBA student, puke. (Just kidding, gentle reader. Your MBA was totally worth 150GR… just kidding.)

I don’t care about a start-up’s written vision statement. When I talk about Thoughtfulness, I’m referring to seriously mission-critical decision-making stuff:

  • Rather than launch with a hacked existing WordPress theme — why don’t we build our own? So it will take two weeks instead of two days… so what? Will that trade-off be worth it, if/when we get to year three as a start-up?
  • When we launch our Premium subscription product — why don’t we limit it to one or two or three features? Yes, I know we could do seven features. But don’t the vast majority of our paying customers really just want one or two or three of these features? Let’s take these essential one or two to three features to their maximum potential of value, rather than waste any time, money, or thought cycles on the other non-essential features.
  • At our brainstorming meeting, we generated 17 hooks for new articles. Which four or five of these hooks are most valuable, scalable, and repeatable? Let’s master and scale these four or five hooks. Let’s hold off on the other 13 ideas, even though some of the them are very good. Let’s save all our mental energy for the very best, most scalable hooks, and execute them to our maximum ability.

Being a CEO is mostly about saying No. Saying No to bad ideas, but also saying No to some pretty darn good ideas. You and your team have limited time, limited cash, and limited mental energy. Direct all of these scarce resources to the very best ideas. The most essential ideas, activities, features, and products.

There is a huge power to Less. I think I’ve always been aware of this, but when I met Greg McKeown several years ago, the lesson really hit home. Greg is an inspiring speaker, especially so when he speaks about “the essential.” (In fact, that’s basically the title of his book: Essentialism: The Disciplined Pursuit of Less.)

Note, I can’t distill the lessons from his book into a short blurb here. But hopefully you can grok the basic philosophy in this excerpt from his webpage:

The Way of the Essentialist involves doing less, but better, so you can make the highest possible contribution.

The Way of the Essentialist isn’t about getting more done in less time. It’s not about getting less done. It’s about getting only the right things done. It’s about challenging the core assumption of ‘we can have it all’ and ‘I have to do everything’ and replacing it with the pursuit of ‘the right thing, in the right way, at the right time’. It’s about regaining control of our own choices about where to spend our time and energies instead of giving others implicit permission to choose for us.


The next time I co-found or jump aboard a start-up, I’m going to strive to be thoughtful.

  • To slow down.
  • To discern the essential. What are the essential features our users want? What are the essential activities to get our business where we want to be?
  • What is the path forward to enable our seven year plan and 100x scalability? No more three year plan with 10x scalability. I want to take a company public some day.

To slow down, be thoughtful, and discern the essential will go against the grain of my nature. It will challenge me. It will hopefully push me to the outer edges of my talents and abilities.

It will be awesome.

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Postscript Feb. 18, 2015: I have created an image — with inspiration from the book Essentialism — to demonstrate that I believe the path to huge value creation involves saying No to many good ideas.

Created with inspiration from the book Essentialism.

Created with inspiration from the book Essentialism.