Hathaway Field Notes — Signals

Measuring the wrong company

2026-06-13T23:02:00.000Z

Companies are taking a hard look at their AI spending and deciding the numbers don't add up. Uber blew through its entire 2026 AI budget in four months — on a coding tool its engineers couldn't stop using. Another company spent half a billion dollars before anyone thought to set a limit. Forrester now expects enterprises to postpone about a quarter of their planned AI investment into 2027 because the returns haven't shown up.

I've heard this argument before. It's the same one people made about the cloud in the early 2010s.

Back then the case against moving to AWS went like this: we already run our own data centers, we run them well, and we run them for less than Amazon would charge us. So why move? On the spreadsheet, the skeptics were often right. A company that had already sunk the capital into its racks and knew how to keep them humming could beat cloud pricing on raw unit cost for years.

They were answering the wrong question.

The cloud was never about running the same workloads for less money. It was about what you no longer had to think about. Moving to AWS turned infrastructure from a capital expense into an operating expense, from a thing you bought, racked, and depreciated into a thing you rented by the hour and stopped paying for the moment you stopped using it.

I lived this one. In my early days as CTO of Mailprotector, our real weakness wasn't the software — it was everything underneath it: buying, racking, and babysitting the hardware our products ran on. Before AWS was anywhere close to ready to replace a data center, I wrote “AWS as a data center?” in a notebook and circled it. A year or two later we started migrating — and not to save money; the spreadsheet didn't make that case yet. We did it to stop spending our attention on machines and put it where we could actually differentiate: the software. A couple of years after that, we turned the lights off on our last data center and never looked back. In hindsight it's hard to separate that one decision from the company's success — maybe even its survival.

Most companies never framed it that way. They measured the cloud against their own data centers, saw a higher unit cost, and stopped there — and because they already had data centers, the shift didn't help them. It helped the company that didn't exist yet. A startup in 2012 could spin up infrastructure that would have required millions in upfront capital a few years earlier, and pay for it out of revenue as it grew. Whole categories of companies got built that couldn't have raised the money to build themselves the old way.

That generalizes well past the cloud. A general-purpose technology rarely just lowers the cost of what you already do; what it offers is a different cost structure, and different cost structures get used by different companies.

When an established company asks whether AI is worth what it's spending, the buried question is whether AI makes the current operation cheaper. Often the honest answer is: not by enough to matter. Bolting a model onto a process that was designed around people rarely pays for itself. A lot of the spending getting scrutinized right now genuinely is waste. The scrutiny isn't wrong.

But "our AI spending isn't paying off" and "AI doesn't pay off" are very different conclusions, and the distance between them is exactly where the data-center operators got caught. They weren't wrong about the numbers. They were measuring the wrong company.

The company that mattered was being built on rented infrastructure, with a cost structure they could never reach by trimming their own. It's being built again now, with AI in the foundation instead of bolted to the side. That's the spend worth watching, and it isn't yours.

How secure is an email message?

2016-03-08T00:00:00.000Z

Email is a communication medium that is used by nearly everyone on the Internet. It's one of the few protocols so widely used, second only to maybe HTTP. That is the power of email. Everyone has it and uses it.

But the security of email is a topic that is often misunderstood. This is largely because there is no single answer to the question, "how secure is an email message?" As a general rule of thumb, by default it should be treated as a very insecure medium of communication. There are ways to secure your email but let's start out with a discussion of the different pieces at play.

How secure is the email message content?

When discussing the security of an email message, you need to break it up into two pieces. First comes the content of the email message itself.

The most insecure parts of an email message are the sender, recipient, and subject of the message. This information is extremely insecure and visible to anyone who touches the message. Think of it like the names and addresses on the outside of a mail envelope. So you should treat these parts carefully because even if you are using encryption on the email message itself, which we'll discuss later, these components will not be protected.

This is the virtual envelope with your content on the inside. If you were to come across a letter, how easy would it be to view what's inside? Not that hard, right? You simply open the envelope. Email messages, by default, are no different. While in transit and once they get to their destination, email messages are like envelopes that anyone with access can open and view the contents.

How secure are email transmissions?

The second aspect of email message security is the transmission of messages from the sender to the recipient. This area is very misunderstood. By default, you have very little control over how a message is handled in transit. Sure, you can make sure your email client is using SSL or TLS when connecting to send the message, and you should, but once you hand it off to the first email server, you are also handing over control on how that message is handled from that point on. Depending on who you are sending the message to it may or may not be transmitted using encrypted connections from hop to hop. This essentially means that the contents of your message could be openly transmitted over the Internet by a bad email provider or ISP. And when this happens, an unencrypted message could be viewed by telcos, ISPs, or government organizations.

Any decent email hosting company will use encrypted connections when receiving and sending email to other email hosts. At Mailprotector, we always default to using TLS encryption for all email message transmissions. Unfortunately many other email hosting companies still don't support encrypted connections, so whenever you send a message, you have to consider the possibility that it isn't going to be transmitted securely.

How to make your email more secure

So now we know why email is, by default, a very insecure communication method. But there are ways to make it more secure.

Check your email client settings

Start by checking your email client settings to make sure you are using SSL or TLS in your inbound (receiving) and outbound (sending) connections. Any competent email provider offers this option and if yours doesn't, switch to one that does immediately. Setting your client to use a secure connection is especially important when using public networks or wifi (like you find at Starbucks) or when on an airplane. Take this recent story by Steven Petrow, a reporter who had his emails hacked mid-air while writing an Apple-FBI story…now that's irony.

"I hacked your email on the plane and read everything you sent and received. I did it to most people on the flight." He had verbatim detail of a long email that he repeated back to me essentially word for word.

The victim in this example wasn't using a virtual private network (VPN) or even SSL/TLS connections when sending and receiving his emails. If you were in a similar situation, anyone on the same network as you could use software to capture the data being transmitted and view it since the data isn't encrypted. Using SSL/TLS options for sending and receiving email is the bare minimum protection you should have on public networks. Ideally, you should also be using a VPN to protect any data you are transmitting while on public networks.

Look into full encryption options

If the security of your email is a high enough priority, you should also consider encrypting the content of the email messages you send. These technologies protect the actual content inside the message. Based on the mail analogy cited earlier, if someone were to get a hold of your encrypted email message, they wouldn't be able to view or understand the content. It would be like opening a letter written in code.

A couple of methods for encrypting email content are S/MIME and PGP. However, there is a downside to both of these technologies. Each requires the sender and recipient to exchange encryption keys prior to sending an encrypted message. So there is a barrier to using these technologies and managing the keys can become frustrating. There are better options available.

At Mailprotector, for instance, we offer a way to make email encryption much easier with our Bracket Encrypted Email service. Not everyone needs this level of security, but some people do. Bracket lets you securely send encrypted email containing corporate and financial data, personal info, legal docs, medical records, but it's much easier for people to use.

Summary: 3 steps to improve email privacy

Check your email client settings to make sure you're sending and receiving email over encrypted connections
Ask your email provider if they encrypt all email in and out of their networks, and if they don't find one who does (hint, hint)
Look into the possibility of utilizing full email encryption options

So while email remains one of the most popular and useful communication mediums, it can be quite insecure by default. That said, you do have options when improving the security of your email.

Your goal needs a system

2016-03-08T00:00:00.000Z

The goal is your destination. The system is your vehicle.

The key to accomplishing something significant is not in the large success but in the small successes. These small successes are based on the habits that will continually move you towards accomplishing your goal.

Most people think the secret of goals is to simply set a big goal and then everything else will just magically happen. They aim high and then never take the first step because it seems too big. They view accomplishing the goal as one giant step. This is where most goals fizzle out.

There is an important piece missing here. It's not enough to just aim for something. Creating a system is the key.

I think there is a place for both goals and systems. However, they work better together than they do separately. You need to set goals to know where you want to go. But setting goals is not enough. You need to have a system that will get you there. The goal is your destination. The system is your vehicle.

The system should be actionable steps that you can consistently perform to move you toward your goal. These consistent steps will form habits. Those habits are the foundation for your system. Once you have a goal, work backwards to determine the habits that will are required to take you to your goal.

Systems people succeed every time they apply their systems, not only when they hit their ultimate goal. These small successes create momentum. And momentum is a powerful thing.

Apple iPhone: simplicity at its best

2007-01-11T00:00:00.000Z

When I read the initial news about the Apple iPhone, I was excited to see what Apple had come up with.

I had no idea that I would be as impressed as I was after watching all of the iPhone demo videos.

Once again Apple has made all other related devices look like a complicated mess with their simple approach to user interfaces.

Apple has set a new bar for cell phone technology that all other companies are going to have to match. Even the most elegant of cell phones like the LG Chocolate series of phones looks obsolete next to the iPhone.

One thing I was tired of hearing about new cell phones on the market is how nice the built in cameras are and that being a key selling point for the phone. You will not see one mention of the built in camera in Apples demo because even though it is there, it is not the reason you should want the iPhone.

Apple has done what all other cell phone manufacturers should do and built a personal communications device instead of adding all sorts of useless features to the already over complicated devices that are out there. And especially recently with the approach of a "new" model being the same old phone in multiple colors.

The hardest part now is waiting until July when they are expected to be released. I am glad that I already am a Cingular customer. If this phone really lives up the expectations, it would be reason enough for anyone to switch to Cingular if necessary for the iPhone.

Playing to win

2007-01-02T00:00:00.000Z

I learned a valuable lesson this holiday season, and it was all done by watching college football. It was a simple lesson that I've heard many times but until I saw it in action, I did not fully understand the power of it.

Play to win

If you want to succeed at anything in life, make sure you approach it with an attitude that you are playing to win.

Expect the unexpected

Many of you may have missed it but the best college football bowl game may have been the least popular one. Boise State was not expected to be able to play with Oklahoma in the Fiesta Bowl this year. Not only did they play with them, they looked like a team that expected to win the game.

Even in the face of adversity as they were down by seven with 0:51 left in the game, they were playing like they came there to win no matter what it took. They ran some of the most impressive (and risky) plays but the most impressive move by the Boise State team didn't happen during a play, it was a decision that was most likely made a few weeks ago.

The coaches were faced with what most teams wouldn't even have considered a decision when they scored a touchdown in the first overtime. They had the choice to either kick the extra point to tie (and go to another overtime) or go for two to win.

Most teams would not have hesitated to kick the extra point and stick around to see another day. Not Boise State, they never even looked at their kicker to go on and kick the extra point. In fact, they were so quick to go for it, the other team had to call a timeout because they weren't ready.

Boise State players and coaches were on the same page that they were there to win the game not just play along with Oklahoma. And it showed on the final play. It looked as if they had this play drawn up for this exact situation all year long. They were prepared and expected to win that game and they did.

So what does this have to do with my business or life?

Everything. When I saw this happen, I thought about many situations in business and life which I went in not to lose instead of going into it to win.

It is amazing how just that simple change in attitude can completely change the result. You should have the same approach to everything you do in life. Figure out ahead of time that you are doing something not just to do it but to win at it and succeed. It will not only change they way you approach that event but how you perform and most likely the result.

Important versus necessary

2006-12-21T00:00:00.000Z

Why is it we describe the things we want to do in life as important instead of necessary?

The definition of important is "marked by or indicative of significant worth or consequence" while the definition of necessary is "of an inevitable nature" or "absolutely needed".

Instantly you can see the difference between the two words.

Look at the things that you do on a regular basis. A normal day will most likely involve you eating, going to work, and sleeping. Why is it that we do these things?

Because they are necessary.

If you decide that it isn't necessary to go to work, then you won't go. But the consequence of that decision is probably going to be losing your job.

So lets face it, what we do on a daily basis are things that are necessary.

How do you describe your dreams?

Things that you want to do are typically considered important but not necessary. That's why they never get done. Until something makes the jump from important to necessary, you will never get to it. There are simply too many other necessary things in life to get to those that are just important.

It's easy for someone to say that something is important to them. Important leaves room for it not to happen. You can always get to the important things tomorrow.

But when something becomes necessary, you will stop at nothing to make sure it happens. It must happen and it must happen now. Why? Because it is necessary.

History has shown that humans are capable of accomplishing the most amazing things. But in each circumstance, you will find one common factor, necessity. If you are having trouble getting what you want out of life, chances are, that something is only important to you, not necessary.

How can you make sure you accomplish more of your dreams?

That is simple, make your dreams and goals something that is necessary to you. Only then will it become a high enough priority in your life to do whatever it takes to make it happen.

If you can ask yourself the question "Is this something that I have to do?" and can honestly answer "Yes", then that is not only important but necessary. You have made the first step to making it happen.

Can you change the way you think?

You are where you are in life because of the priorities you have and had. In order to change your life, you must change the way you think and prioritize. So the question really should not be can you change the way you think but rather…

Will you change the way you think?

Once you have made this decision, you will think about your dreams differently. You finally put them higher on your list of priorities. They will no longer only be important to you but now they will be necessary.

"So many of our dreams at first seem impossible, then they seem improbable, and then, when we summon the will, they soon become inevitable." —Christopher Reeve

Are your dreams inevitable?