A letter from Dad and a Hotmail account changed my life.

Jason Bennett
4 min readSep 10, 2022
Khobar Tower, Khobar, Saudia Arabia after June 25th, 1996 Terrorist Attack

It’s funny how an event, seemingly of little consequence at the time, can have a lasting impact on our lives. Here’s a quick note on how I started my journey in technology and found success in business and life after receiving a letter from Dad and opening a Hotmail account.

On June 25th, 1996 a petrol (gas) truck pulled up and parked in front of the Khobar Towers, an 8-story barracks for US Air Force enlisted personnel in Al Khobar, Saudi Arabia, and promptly exploded due to the upward shape charge underneath the fuel tanks. The blast tore the front of that building off and killed 19 US soldiers.

36 hours later, I was standing in front of that broken building in Al Khobar with my squad assessing the massive hole in the ground left by the explosion and the mountains of rubble. We were an Army special operations unit out of Ft. Lewis, WA.

Somewhere between six months chewing sand and chasing bad guys across endless deserts in the Middle East and another four months attached to a SEAL team doing the same, I got a letter from Dad.

The Letter

Dad was a former intelligence officer in the Air Force and was working with computers long before 99% of us knew what computers were. And, Dad was on the leadership team that built the Arpanet… the precursor to the internet.

“ask the desk clerk to show you how to get on the “internet” and how to open a “Hotmail” account”

I don’t have the letter, it was lost in transition, but I remember it clearly. Went something like,

“Son, haven’t heard from you in….”

Fast forward to the juicy bit where he wrote,

“…every Air Force base in the world has a computer lab. Go on base and find it. When you get there, ask the desk clerk to show you how to get on the “internet” and how to open a “Hotmail” account. When you do, send a note to “<Dad’s email address>”. (Never will forget the “” lol).

So, I did just that.

The Hotmail Experience

Sent an email.

2 minutes later got an email back.

And, viola. I was hooked.

It wasn’t the internet, Hotmail, or the bulky computer that hooked me. I wanted to know what made that happen.

How did I just communicate with Dad from 18K miles away in just seconds?

What technologies, infrastructure, manpower, etc. made that happen?

And, how would this transform business and our lives?

I just had to know.

The Journey Begins

Nine months later I was enrolled in the University of Arizona’s MIS program within the Eller School of Management.

A semester later, US News & World Report ranked our MIS program “#3 Best MIS program in the US”.

A year later I started my own computer networking business targeting small to medium doctor’s offices in Tucson, AZ.

Another year later I signed a contract with IBM.

And a year after that I graduated and started leading a team at Big Blue.

Five years after that, for a Washington DC VAR, I drove the initiative to be an early adopter of Amazon Web Services (AWS) as I was leading a team that would transform a commoditized business model to that of high-margin #SaaS and services (which ultimately got us bought).

And the story continues….

Dad doesn’t remember sending that letter but I’ll never forget it. For how it inspired me. For how it helped me think different, think big, and try something new.

Thank you, Dad

My Dad (the Colonel), Son, and I

I’m Jason Bennett, a RevOps genius, product-led growth strategist, and Fractional Chief Growth Officer positioning enterprise SaaS companies for A-Round.

My mission is to help 000’s of founders find their lane to sustainable growth.

And, I love to write about SaaS 4.0, the founder’s journey, and self-improvement.

Find out more on brllntly.com

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Jason Bennett

I’m an entrepreneur, advisor, and VR fitness nut who writes about SaaS growth tactics, the founder’s journey, and lifehacking.