The Best Hello Operator Posts from 2025
What investor-backed executives like you read, liked, and shared the most this year
It’s here.
The week between Christmas and New Year’s.
Or, as I like to call it, the haze.
The normal rules of time and nutrition do not apply in the haze. Nobody knows for certain what day it is. Lunch is a combination plate of leftovers from three different meals, supplemented with leftover cookies from a holiday gift basket that sits on your kitchen counter for. An unbroken stream of bowl games and Christmas movies plays on the living room TV. Work feels like a distant fever-dream. And we all oscillate between thinking deeply about the year ahead and wondering if anyone has eaten that last piece of pie in the fridge yet.
For me, that deep thinking includes looking back at my writing and analyzing what performed the best. So this week, I pulled my Substack stats and looked at what you read, liked, and shared most in 2025.
Here are the articles that rose to the top of that list, how I feel about them, and why they might be worth another read (even if you caught them the first time around).
Thanks for reading, and happy holidays.
Most Liked: What My Dad Taught Me About Work
We all have role models in our life. And if all we did was actually use the lessons they taught us, we’d probably be better off than we are with any framework, playbook, or modern-day tip we picked up from some self-proclaimed expert we’ve never met. I’m lucky to have a great role model in my Dad. And his approach to his work and career has deeply shaped how I think about my own. This article took me the longest to write of anything I’ve ever published. It’s also the one I’m most proud of. If you only read one thing from this annual recap, make it this one.
—> Read it here
Most Shared: How To Make ChatGPT Sound Like You
This was my practical guide showing people how I’ve trained AI to write in my voice.
I think one of the biggest barriers to people using AI more frequently is they get frustrated that it doesn’t sound like them. But with a little structural setup, you can solve this problem in about 20 minutes. Not only does it make any AI tool more satisfying to use, it also opens your eyes to all the possibilities for applying AI in your work and everyday life. It’s my tactical, step-by-step guide for removing one of the most important frictions to putting AI to work.
—> Read it here
Most Read: AI, SEO, and How To Simplify Your Content Strategy
I wrote this when everybody was panicking about the impact of AI-generated content flooding search results.
I think people wanted a bit of a technical explanation re: how SEO works, how AI is changing the SEO game, and some pointers for how to use AI to enrich their content strategy. I wanted to cover all three in this article, and that’s why I think it landed. It also includes some of my philosophy on “what you need to know first” before getting going with a new content marketing strategy (hint: focus on the questions your customers are already asking you in sales calls).
—> Read it here
Honorable Mention: How To Hire A Simplifier
This was the only post that showed up in the top three across all three metrics: likes, shares, and views. It’s about the most important quality that all A-players share: They’re simplifiers, not complicators.
Every time I hire an executive into one of our portfolio companies, this is the most important quality I assess for. This article covers not only why being a simplifier is so valuable, but also the specific questions you can ask in your next interview to uncover whether someone can help you simplify your business.
—> Read it here
Thanks for reading and subscribing. If you have questions or topics you’d like me to cover in 2026, reply to this email and let me know. I’m building my content calendar for next year as we speak, and I’d love to hear from you.
Hell of a year! Enjoy the liminal space of this week!