28 Lessons I’ve Learned from Jason Calacanis
A list of lessons I’ve experienced while working for Jason over 5 years.
I woke up this morning to write in my gratitude journal, and flowed into reflecting on some lessons I’ve learned working for Jason for over five years.
Also, a new year goal of mine is to write more, in any form. Journaling thoughts, sharing ideas/lessons, exploring interests, etc… so here goes!
28 lessons I’ve learned about work & life from Jason
This list is in no specific order.
Follow-up, always.
Simple is better.
Be clear and concise when speaking and writing.
Have a bias for action (if it can be done right away, do it right away).
Share your ideas with the world.
Be the host, be the friend.
Careers are built on the weekends.
Document what you work on (EOD, EOW).
Hang around people smarter than you.
Focus on one job/task at a time.
Be candid and express your truth.
Writing is clarity of thought. It makes you sharper.
Always be iterating. Ask yourself “can I make this 1% better?”
When you have an idea, get all the IP for it. You never know what that idea might turn into.
When you get a text about work, act on it immediately. It’s probably more important than a slack or email.
To move the needle, everyone on your team needs to be aligned.
Study the restaurant menu and order family-style.
Learn new skills consistently. Get to 50-80% proficiency in that skill.
Increase your intellectual endurance and curiosity by reading, and talking about what you read.
Loyalty gets rewarded.
Tell stories with a comical flair. People will remember it, and there’s no better feeling than bringing joy to someone.
Delegate tasks that don’t energize you (while knowing you will still have to do tasks that don’t energize you)
Always have a strong internet connection and proper audio (wired headset with stick microphone)
Always play the long game, and enjoy the journey.
Use Grammarly and Hemingway app to simplify your writing.
Review your calendar daily and ask “is this the best use of my time today to reach our mission of X”
When you have an idea, write it down, and take one action toward that idea (can be as simple as creating a Notion page for the idea)
Take notes on paper, be fully present in meetings & conversation.
I’ll revisit this list again sometime in the future to update it (last updated 1.17.23)
Grateful for these lessons.
The end.

As someone who has personally benefitted from Presh's conscientiousness at AIS MIA, it is obvious that @jason is a #1 Mentor. Perhaps after "Angel 2" he ought to write "Mentor".
Congrats Presh on 5 great years.