dark side of “ready, fire, aim”

Jim Hamilton
February 20, 2025

Money loves speed.

If you want to win this game, you’ve gotta be able to move fast.

This is one of my most closely-held convictions in business.

It’s why Reid Hoffman says:

“If you’re not embarrassed by the first version of your product, you’ve launched too late.”

And it’s why legendary entrepreneur Michael Masteron wrote a book called Ready, Fire, Aim.

(if you haven’t yet read it, I highly recommend it.)

Regardless, the concept is simple:

Get your work into the hands of your customers as soon as humanly possible.

Prioritize getting results and feedback quickly…

Then iterate from there.

Don’t wait for it to be polished or perfect.

That comes later.

This is a philosophy I can attribute a lot of my success to over the years.

However:

It’s also led to a few embarrassing woopsies.

Case in point:

I decided to order some branded envelopes to mail out paperback copies of my book to friends, family, and clients.

But in my haste to move quickly…

I neglected to double-check how big the envelopes were or how many I was ordering.

So imagine my surprise when 100 of these puppies arrived at my doorstep:

As you can see…

Not only was it WAY more than I’d ever need…

They were also basically twice the size I should’ve got.

Woops 😂

I share this with you because I don’t want you to think I’ve got everything figured out.

Or that I never make mistakes.

I do.

And there was a time when my inner perfectionist would cringe at this type of stuff.

Or sending out an email with a typo…

Or launching a new offer with an ugly-looking sales page.

But guess what?

Now I just laugh at it…

Because I know all of the above is rooted in insecurity.

My fear of being judged by you.

This is not to say I never struggle with insecurity anymore…

Just that I’ve learned to set it aside.

And I’m happy to trade looking silly in front of my audience for having ads, offers, funnels, etc that work.