Hi. I’m John Lilley
I’ve been writing the Second Story newsletter since 2025. Yup, that’s right. I just started. 🙂
I’ve worked in technology for almost 25 years, focused on digital and marketing technology, first as a developer and a project manager before moving into an executive role. We won a Webby Award at Vail Resorts back in 2012. Lately, I’ve been the Chief Information Officer at Aspen for almost twelve years. I love my job.
I’m also an Amazon bestselling fiction author under the name Jack Arbor, where I have seven published novels and one on the way. Always a new one on the way.
You can find me elsewhere on LinkedIn and at JackArbor.com
Chief Information Officer at Aspen.
Creator of the Second Story newsletter
Fiction author @ JackArbor.com
What Is The Second Story Newsletter?
Technology can be simultaneously enthralling, vexing, problematic, and exciting. Social media, as an example, embodies all those traits, and more.
Artificial Intelligence (AI) is either the most transformative and impactful technology since the internet, or it’s over-hyped and steeped in problems that will prevent people from using it. We don’t know yet.
Human Powered is a place to explore that conundrum.
Human Powered is a place where I publish deep dives, analysis, and curated content on AI’s impact on the human condition. The focus is on practical impact and AI’s ability to be useful.
Why I Write
I write to explore ideas.
For example, should I continue writing fiction in an age of generative AI? I honestly don’t know.
And, I write to make sense of the world.
For example, what happens if I use AI to try to write a book about AI?
I believe technology exists to serve the human condition. Technology is useless unless it helps humans. AI has been around as a concept since 1956. It wasn’t until OpenAI slapped a user interface and natural language processing on the front of a large language model that it became useful to humans.
Whether ChatGPT is useful or not is debatable, I guess.
And so I write about technology and its intersection with humans.
I work hard to explain technology concepts in ways that are understandable and help people use technology to make their lives better.
If this sounds interesting to you, read on. And please subscribe to Human Powered.
Why I Travel
In 2001, right before 9/11, I moved to New Delhi to help run off-shore development for the consulting firm I worked for. Our flat was in Anand Niketan, where we lived for over a year, and our office was in Gurgaon. During that time, I traveled throughout Asia, including Hong Kong, Singapore, Japan, Thailand, and Vietnam. The people I met were cemented in my consciousness forever.
Now, I travel for the same reason I write: to make sense of the world and explore new ideas.
Nothing adjusts your perspective like the world view that evolves from traveling through unique cultures, meeting people different from yourself, and breaking bread with locals.
My travels influence my writing.
There’s a reason this picture is my Facebook profile picture. It was taken in Bangkok in February 2025, and it represents purposeful exploration. One of my core values.

About
Here are a few notable things about me.
I’m the Chief Information Officer for Aspen
- Head of technology for a premier ski and hotel company (aka best job ever)
- Webby Award winner for Vail Resorts’ Epic Mix technology
- I started my career in technology in 1997, the year IBM’s Deep Blue beat Garry Kasparov in a 6-game match
I’m the creator of The Second Story, a newsletter
- I write deep dives, analysis, and curated updates about AI’s impact on the human condition
- I write it for myself, to better understand AI’s impact. Maybe you’ll enjoy it too.
- New edition weekly, subscribe here
I’m the Bestselling Fiction Author, Jack Arbor
- Seven novels published in the adventure thriller genre
- My first novel became an Amazon best seller in February, 2018
- I originally used a pen name to separate my fiction life from my work life, now I don’t care
Interesting Bits and Bobs
- ”Write More” is tattooed on my arm to remind me what’s important
- I’m married to my best friend and partner in crime, Jill
- My favorite activity is to go uphill on skis and skins
- We prioritize travel; especially to Japan
- I was born on Tachikawa Air Force Base, outside Tokyo
- My team is the Detroit Tigers
The Second Story
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