Table of Contents

• Essay: Some Things You Should Know About Pricing

  • 🪙Pricing Is Not Always About Cost

  • 💲Pricing Is About Psychology

  • 🕜Charging Hourly Is Full of Problems

• 🔮Reflections On AI

  • Vibe Coding

  • 🔥HOT TAKE: People Will Forget How To Read Books

• Fin

Hi Folks, lots going on behind the scenes. Was traveling on the east coast for a bit and happy to be back. Been heads down building and playing with things.

Some updates:

• The Live Fractional CISO Success Course will now start on Monday 7/21.

  • It will run daily that week at 12pm Pacific and include 3 months access to the group coaching afterwards.

  • I will be sharing everything I’ve learned about Fractional CISO, including the failures and gotchas.

  • Lots of war stories!

  • Templates included.

  • Enroll here

• I will be rebranding this newsletter to The Security Cafe and moving it to a different platform. More to come on why later.

• I have a new section in the newsletter called Reflections on AI. Includes a bit of rant at the end there. 😅

Essay: Some Things You Should Know About Pricing

I shared some thoughts earlier this week on LinkedIn about pricing your service. The short of it, pricing is part art, part science, and part luck.

Even SaaS founders sometimes don’t know how much to charge. While I have a whole day in my course dedicated to pricing and Sales, I want to share some truths regarding pricing.

🪙Pricing Is Not Always About Cost

I saw a recent video by Johnny Harris on why food is so expensive, and spoiler alert, it wasn’t about cost.

Ok, assuming you are not a monopoly, then what determines pricing?

Well, let me ask you, why does McKenzie charge $300 - 800/hr?

Because they can.

They have built a brand name. Not only that, they (assumingly) deliver quality service or at very least make you think you are getting quality service.

Along with their name, comes a guarantee that the work can or will get done.

Of course this is a nuanced topic, better discussed over some coffee.

This is why Marketing is such a major component of pricing. It’s all related.

💲Pricing Is About Psychology

If you’re a behavioral economics fan, then you already know what I’m going to say. 

There are few psychological factors that can influence pricing and more importantly, acceptance of that pricing.

• Value - That you are getting the same or more of a value from the service / product provided

• Quality - Similar to Value, but are you going to get the same quality as the next thing

• Urgency - How much time do you want to spend shopping around for a lower price?

• Scarcity - If you’ve shopped around already, and everyone (including your friends) are telling you the same thing, then you don’t have much choice.

There are whole books written on this topic. For example, in the classic book Predictable Irrational, the author talks about how people will go across town to save a few dollars on items priced under $10 or $20 dollars, but will add-on “undercoating” for hundreds or thousands of dollars on a new car during the purchasing process.

Think about this, diamonds weren’t worth anything 200 years ago.

Can you think of anything else that has perceived value, but can’t be explained with science?

🕜Charging Hourly Is Full of Problems

This is also another subject that requires a lot of time to discuss. I will simply leave you with a comic by Jonathan Stark, who is the authority on the subject. He has a podcast called Ditching Hourly where I recommend you start from Episode 001.

Hopefully this post got you thinking a little on how you approach pricing your product or service. It isn’t just about one thing. There are a lot of components involved with coming up, selling, delivering, and even scaling a service.

Of course, I discuss these topics in depth in my Fractional CISO Success Course.

🔮Reflections On AI

I think I will have a permanent section on my reflections on AI and society. I was going to call this Society and Tech, but let’s see how this goes. I’ve shared plenty of thoughts previously on the Enterprise Security Weekly podcast with Adrian Sanabria.

Vibe Coding

So I did some vibe coding this weekend and wow, it was amazing! I’ve been itching for so long to do it, and now that I tasted it I don’t want to stop! (I lost quite a bit of sleep this weekend)

One of my favorite parts is the auto debugging. I love scripting and building things, but the downside is debugging errors and issues. Of course, it’s helpful sometimes to keep an eye and help it go in the right direction, otherwise it can sit there forever in an endless loop.

Here are some videos for inspiration:

• Cursor Replaces Your Entire Business Stack (Full Demo)

• Claude Code Replaced Cursor for Me… Here’s Why

Some of the projects I started vibe coding are:

• Building a VA assistant to build, edit, and update landing pages using LLM powered browsers

• Google Workspace Drive Audit tool

If you’re already doing some vibe coding, lmk would love to have a co-working session.

🔥HOT TAKE: People Will Forget How To Read Books

How many people know how to drive a manual car?

How many people still go up a mountain without electric assist?

One of the filters I have when out there in the dating world is whether she reads or not.

Reading and written communication have been among the most impactful forces driving societal progress throughout history.

• Reading and writing have been foundational to societal development. They enable the preservation and transmission of knowledge, laws, history, science, and culture across generations and distances.

• Written communication amplifies learning, coordination, and innovation, all of which are key drivers of societal progress.

A close second is trade and oral communication. We are a social species after all.

Something I’ve noticed now a few times from those who are deep in the AI space, is they don’t read books anymore.

Instead they will upload the book to the AI and ask it questions and summarize.

I’ve seen this with other content such as YT videos.

I get it, some books have some fluff. YT videos can be played at 1.7x.

However, just as working IRL in an office is VASTLY different than working remotely, the same applies to consuming first hand knowledge.

I get it, new sources, light discussions, and other material can be compressed and transcribed, but for some content the nuances from an author will get lost in translation. Literally.

Especially if the author has a style of communication they want to get across. 

Let alone any italics, emphasis, or footnotes.

All that is lost in translation.

I’ve learned so much from YouTube, it’s been a Godsend. Bees, Electrical wiring, Car Mechanics, Boating, and so much more. Yes, AI is awesomesauce, but it doesn't replace our communication styles.

Side Note: Rock Climbing is the only thing I’ve had a hard time learning with YouTube.

My point here is that reading a book will be a lost art. Just like driving a manual or gas powered car in the future. 🏎️

Fin

Are you going to be at Blackhat / Defcon? Lmk!