The Easiest Issue of the Year (That Somehow Took the Longest)
Entrepreneur Office Hours - Issue #312
One of the underrated perks of writing a weekly newsletter like Entrepreneur Office Hours is that, once a year, you get to write an end-of-year retrospective. It’s the easiest issue of the year! No new ideas required. No fresh anecdotes. No clever framing devices. You just look back at everything you wrote, pick a few favorites, link to them, and call it a day. It’s the content equivalent of leftovers — and I mean that in the best possible way.
Or rather… that’s the theory…
In practice, this issue somehow always takes longer than a normal one, and I’m not entirely sure why. I’m guessing it’s because the moment I start looking back, I see more than just links — I see context. I remember what was happening when I wrote each piece. Which ones came from class conversations, which ones came from student emails, which ones were born out of frustration, excitement, curiosity, or exhaustion.
Suddenly, what was supposed to be a quick “greatest hits” becomes an exercise in reflection. And reflection, as it turns out, takes time.
So yes, I didn’t have to come up with a brand-new idea for this issue. But I did end up re-reading lots of what I wrote this year, thinking about what resonated, what didn’t, and how my own thinking about entrepreneurship has continued to evolve. Which feels… appropriate, actually. After all, that’s what this newsletter has always been for me. I realize, functionally, it’s a place to share advice for all of you, but, for me, it’s a running record of ideas tested in classrooms, office hours, conversations, and real entrepreneurial work. Looking back on it all at once is a reminder of how much can happen in a single year, even when you’re just showing up week after week and writing one email at a time.
Below, you’ll find a handful of my favorite articles from the past year. If you missed them the first time around, I hope you enjoy them now. And if you’ve been reading all along, consider this a chance to revisit the ones that stuck with me the most.
Heads up… this will be the final issue of Entrepreneur Office Hours for the year. And that means I need to end with a huge thank you. Thank you for reading, replying, sharing, disagreeing, and sticking around. I genuinely don’t take that lightly.
I hope you have a restful, joyful holiday season and a happy new year. And when we’re back in 2026, we’ll be rolling into it with some big, exciting updates for EOH that I can’t wait to share.
See you on the other side.
— Aaron
This week’s new articles…
If Your Startup Is Interesting You’re Doing It Wrong
The things that excite you most as a founder are also the most likely things to destroy your company.
I’m Still Surprised Founders Keep Making the Same Mistake
After 10 years teaching entrepreneurship, I can’t believe I’m giving the same advice to every founder I meet.
Top 5 Most Popular Articles of 2025
#5) The Slide You Need to Remove From Your Pitch Deck Immediately
The moment investors see it is the moment they stop listening.
#4) The Most Important Startup Skill Nobody Talks About
It’s an important life skill, too!
#3) Why Most Startups Fail Before They Ever Make a Sale
Inexperienced founders are always making the same mistake.
#2) The Best Entrepreneurs Are Smart Enough to Not Build Startups
What if you could be a great entrepreneur without ever have to deal with the challenge of launching your own company?
#1) The One Lesson About Startups No Business School Can Teach You
You’ll learn a lot in business school about building and running companies, but there’s one thing that’ll never happen.
Yeah this is the trap when “leftovers” turns into “context overload.” When I review my own ops notes, I’m not skimming.. I’m reliving every decision behind the line. Takes time, but it’s clean work.