Eventually You’re Going to Notice the Cannons.

My Wife and I Have Different Ideas About Transparency

My wife and business partner freaked out a little when she read my last article.

It was too transparent.

It could spook the horses.

It made us look weak.

I understood what she was worried about. I had written openly about debt, pressure, risk and what it feels like to own a business when some of the pitches coming at you matter quite a lot.

So I showed her the article again.

I hadn’t written that the company was in trouble. I had written about what pressure feels like when you’re the person carrying it. In fact, I thought the whole thing was rather optimistic.

But underneath her reaction was a question we’ve been wrestling with for years.

What if people see us for what we really are?

And my answer is increasingly:

Good.

They should.

For years I’ve pushed against the instinct to make Thinking Cap look like everybody else. Look bigger. Look more corporate. Sand off the eccentricities. Make the website reassuringly beige. Use the same language as every other enterprise software company so nobody gets nervous.

The problem is that it doesn’t actually make us look like Loblaws.

It makes us look like Longo’s trying to look like Loblaws.

And why would we want to do that?

Nobody walks into a farmers’ market because they were fooled into thinking it was a supermarket.

They go precisely because it isn’t.

They want the person who grew the tomato. They want the strange cheese they can’t get anywhere else. They want somebody behind the counter who knows why this particular olive oil is worth buying. They accept that there aren’t forty brands of toilet paper because that isn’t what they came for.

That’s much closer to what we are.

We’re the farmers’ market.

We’re the European specialty shop.

We’re the retailer who sells truffles.

And if you put me in charge of Walmart, I would probably drive it into the sea.

I don’t have that skill set.

I don’t want aisle after aisle of interchangeable things efficiently stacked to the ceiling. There are people who are exceptionally good at building and operating organizations like that. I’m not one of them.

Give me the truffles.

Give me something peculiar and difficult that requires taste and judgment. Give me a customer who cares enough to understand the difference.

That’s a game I know how to play.

The same thing happens when small technology companies try to reassure customers who really want to buy IBM.

We can make ourselves look more corporate. We can carefully avoid saying anything that reveals an actual human being runs the company. We can fill the website with stock photography and enterprise language and reassuring statements about solutions and transformation.

But we’re not going to become IBM.

At best, we attract people who really want IBM but can’t afford IBM.

That’s not particularly interesting to me.

I want the customer who doesn’t want IBM.

I want the customer who looks at a giant vendor and thinks: I don’t want to be customer number 47,291. I want somebody who actually cares whether this works.

Those customers deserve to know what they’re buying.

We’ve been around for more than twenty years. We have longstanding customers. We have recurring revenue. We have a product that does complicated things extremely well. We’re stable.

But if your procurement criteria require a vendor with twenty million dollars sitting in the bank, it ain’t us.

If what makes you comfortable is knowing the entire senior management team could disappear tomorrow and the machine would continue operating exactly as before, that’s not us either.

We’re not disappearing.

And there is another side to having the people who run the company this close to the product.

We care.

A lot.

Probably an unreasonable amount.

The people making decisions about what Thinking Cap becomes aren’t seven organizational layers away from the customer. We’re right here. We know the product. We know the customers. We argue about it. We invent things. We change our minds. We take risks. Sometimes we get things wrong and fix them.

That’s not the weakness we’re supposed to hide.

That’s the product.

There is certainly a market for enormous, predictable organizations where no individual person matters very much. Scale provides real advantages. So does redundancy. So does having enough cash that almost nothing can frighten you.

But those advantages have costs too.

Big organizations have gravity.

They have processes designed to prevent mistakes, which also prevent movement. They have people whose job is to protect the existing business from the strange new idea that might disrupt it. They have enormous resources, but those resources don’t always translate into curiosity, urgency or courage.

We have different advantages.

So maybe we should stop disguising them.

This is something I’ve come to believe more strongly as AI changes our industry. For the first time in a long time, some of the advantages that belonged almost exclusively to enormous companies are getting cheaper. A small team can suddenly have capabilities that recently required a much larger one.

That doesn’t make us Walmart.

It makes the specialty shop more dangerous.

And perhaps being more honest about who we are gives us the chance to become more of it.

Maybe the website should tell the truth.

We’re a pirate ship.

We’ve been at sea for more than twenty years, so apparently we’re reasonably good sailors. The ship is sound. The crew knows what they’re doing. We’ve survived storms. We’ve picked up some treasure along the way.

But we’re still a pirate ship.

If what you want is a cruise liner, I shouldn’t convince you otherwise. Eventually you’re going to notice the cannons.

I’d rather you see the flag before you come aboard.

Because there are customers out there who aren’t frightened by it.

They’re looking for it.

So yes, I’m going to keep being more transparent. I’m going to talk about what it’s actually like to build this company. I’m going to admit when something is hard. I’m going to talk about what excites me and what scares me. I’m going to let customers see some of the people behind the product instead of pretending Thinking Cap was extruded from a sufficiently large corporate machine.

Some people won’t like that.

Good.

Knowing who shouldn’t buy from you is almost as valuable as knowing who should.

After more than twenty years, I don’t think our next stage comes from becoming a more convincing imitation of somebody else.

It comes from becoming much more obviously ourselves.

So yes, we’re going to fly the flag.

It might scare off a few people who are never going to enjoy the voyage anyway.

And that’s okay.

Because we’re a ship, and we have responsibilities. We’ll maintain our SOC, we’ll have a disaster recovery plan, and we’ll do penetration testing. This ship needs to float... reliably, safely, and with discipline... but let’s be clear, it’s still not a luxury yacht.

And it might finally let the right ones see the ship.

So I am sorry wife but it is what it is; I am every inch Captain Jack Sparrow and Thinking Cap is the Black Pearl, and I wouldn't have it any other way.

Drink up me hearties, yo ho ho…

A pirate’s life for me.