The “Operators Mindset”: How I Make Better Decisions by Loving the Chaos

We think our mind is so big and bold and beautiful… but it has so many limitations and one of the things it likes to do is lower our expectations to keep us safe.

That is great if you are avoiding a bear!!

Terrible if you are trying to build a business!

There are three big decisions that have changed the course of Portland Leather and they have all felt borderline stupid.

But that is why I have learned to love the chaos.

Our first, big, chaotic decision

Before Portland Leather turned into a 100M company, it was just me and my partner in a one-car garage.

We were making leather journals, going to art festivals every weekend and loving life! Then we went off to hire our first employee… and that garage started to feel small.

I knew we needed to move into a new space but I was scared out of my mind!! I did not know what to do. So we did what most people do when they are scared and played it safe.

We started looking for places that were up to 4 times larger than what we had at the moment…. And something magical happened.

The morning we were supposed to sign a lease, my girlfriend was running late, so I refreshed the listing page one more time and… BOOM! A new spot popped up a few blocks from our place and we went to go see it.

That place was waaay too big for us.

It was a 2,000 square foot pole dancing studio… for three people!!

Mirrors everywhere. Purple walls. No logic!!

But we took it anyway.

Knocked down some walls… and before we knew it, there were 40, 50 people working under that roof.

Now this is what I want you to understand:

If you want to scale, you have to live in the future. If we had gone on to sign the lease in the first stop that was 4 times bigger, we would’ve stayed small!!

We had no idea what we were doing.

But you know what??

We figured it out.

Spend more time where you are going, than where you are at

Most of you know my CMO, MacCoy Merkley.

Back in our Etsy days, we hired him as a photographer. We didn’t give him much direction… so he started working on our website. Then he kept saying something that sounded insane at the time: “We need to shut Etsy down!!” He also said that if we did not focus on shopify, we were never going to grow.

At that moment, I had no idea that being on Esty was killing us! Sales were coming and people were happy.

But everything had to be personalized so it was slow and exhausting and had zero room to scale. Then, I realized that if we did not shut it down, we would have never taken the time we needed in order to grow shopify!!

So we did..

Every employee said we were stupid.

6M later… brilliant frickin idea!!

If you want to do something special, spend more time where you are going than where you are right now. Our lives will be filled with business and we pretend that it is important, but that is not going to get you where you want… it does not scale!!

You do not take action when you have everything ready!!

You make the move, then… get your ass kicked a little for 6 months.

Next thing you know.. Wow! You have grown!!

Books will be written about people who were afraid and got bold

Then, Covid hit. We were so screwed.

We had little product left and no one could come in to make our bags. So Maverick says this great line, “Books will be written about people who were afraid and got bold”.

2 weeks later, I got on a plane and flew down to León, Guanajuato in Mexico and set up shop.

Fast forward to today:

- We are the largest leather bag manufacturing company in North America

- Employ over 1400 people

- Multiple retail stores opening across the US

What the heck!!

Embrace the Chaos

Being afraid is natural… your body wants to keep you comfortable and safe.

Warm and fuzzy!

But warm and fuzzy ain’t gonna get you to where you want to go!

The people that are really killing it in this world are not the ones avoiding chaos. They are riding it. They get on a ride, see where it goes, and figure it out on the way today.

You cannot grow if nothing changes.

And for things to change, you have to live in that chaos first.

Learn to love it!

That is how real growth happens.

Curtis Matsko - CEO & Founder of Portland Leather Goods