Ready, Fire, Aim by Michael Masterson
Back when I was a freshman in college, I picked up Ready, Fire, Aim by Michael Masterson (a pen name) while falling down a very specific rabbit hole — the world of 1980s South Florida hustle-culture business people. Mail order, media, direct response marketing. Not exactly the role models section of a business school syllabus. But it’s one that I picked up – and stuck with me.
But that subculture gets one thing profoundly right. And it’s the same thing that the lean startup crowd and Silicon Valley eventually repackaged for a new generation.
The Core Idea
If you’re reasonably sure about a business idea — or the whole self-employment thing in general — there is an enormous world of things you don’t know that you don’t know.
The only way to find out what those things are is to just do the thing. Get a client. Ship a product. Try to make one sale. Make the pitch.
Because here’s what happens when you do: you fail. Or at least stumble. And in that stumble, you learn something you could never have learned by planning, researching, or waiting until you felt ready.
That’s the whole book. Instead of Ready → Aim → Fire, it’s Ready → Fire → Aim. Go ahead and shoot. Miss. Now you know where to aim.
It’s a little embarrassing how long it took me to internalize this. But once you see it, you can’t unsee it. The business plans that never launched. The side projects that stayed in a Google Doc forever. All of them had one thing in common — I was still in the aiming phase, which is really just a more productive-feeling version of not starting.
The Book Itself
It’s a fast read. It’s also patently weird — which, honestly, fits the genre. Masterson writes with the energy of someone who has closed a lot of deals in a lot of rooms you probably wouldn’t want to be in. There’s a definite slicked-back hair, unlit cigar vibe throughout.
That said, the weirdness works in its favor. The book sticks with you because it’s a little odd. It’s not another polished HBS case study. It’s a guy who figured something real out and is telling you directly.
Should You Read It?
I wouldn’t call it a must-read. If you’re already deep into lean startup thinking or have read enough about iterative business-building, you’ve gotten the main idea elsewhere — probably with better examples and fewer references to 1980s direct mail.
But if you want a business book that comes from completely left field and will still be rattling around in your head six months later? Ready, Fire, Aim is worth your time. Useful and a little inspirational, in the scrappiest possible way.
Ready, Fire, Aim by Michael Masterson makes one argument and makes it well: stop planning and start doing. The only way to discover what you don't know about a business idea is to actually attempt it — fail, learn, then aim better. It's a fast, oddly memorable read with a distinct 1980s hustle-culture personality. Not a must-read, but surprisingly useful and hard to forget.
- Core idea is genuinely actionable and sticks with you
- Fast read with a distinct, memorable personality
- Connects to lean startup thinking before lean startup was a thing
- The 1980s direct-mail vibe won't appeal to everyone
- If you've read lean startup literature, the main idea isn't new
- Light on concrete examples to anchor the philosophy
