At 24, I was precocious and completely unpredictable.
It was a happy mix of smooth talking and right-place-right-time that landed me at the helm of Sailor Jerry Rum for William Grant & Sons. I was the youngest person anyone had heard of in a role like that––which isn’t likely to change, given what my experience looked like.
I helped our parent company get out of the team’s way, developing our best thinkers to drive marketing ideas that would help the brand to close in on 1 million cases worldwide. But it was my soft skills––or rather, the lack there of––that really stuck in people’s minds.
I learned a lot in those days, but the most important lesson I took with me was the importance of not being an asshole. There is no justifying it, no matter the circumstances. And I especially encourage you to not make matters worse by excusing your behavior with an “I’m sorry, I’m really stressed out/I have so much on my plate.” Because what you’re now telling the world is, “I’m an asshole who can’t figure out how to prioritize, delegate or manage time effectively.”
That was me. I was that asshole. And, if you’re reading this, it’s probably because you’re a founder or an aspiring entrepreneur, so there are going to be times when it will be so easy for you to fall into that trap, too. But if you set yourself up for success by creating enough fail-safes, you can avoid the traps altogether.
So, this is a list of my best habits, resources and practices for keeping ahead of the game. Effectively, this is my handy guide for How to Not Be an Asshole Who Can’t Figure Out How to Prioritize, Delegate or Manage Time Effectively. It’s about how to have an edge, rather than live on one.
1. Hire a team you would kill for, and then inspire them to want to kill for you. Build the cult––create camaraderie AND competition. At Matchbook, we have three “Guiding Light Principles:”
Show up early
Have each others backs
Own your shit
These principles are about competition and performance, teamwork and accountability. When you can foster a team that keeps those values front and center, fewer things will go wrong––but when they do, your team will be there to work through problems with productive energy.
2. Record your best thinking––prioritize––never drop the ball. I use OmniFoucs for this. It provides a place to capture all of your ideas, notes, to-do’s for you to process later––it’s called the “Inbox.” All of the emails I get that require action get forwarded here as well. Every day I try to spend thirty minutes processing my inbox into “projects.” Projects are any big to-do’s that have multiple steps. I review my projects every Sunday evening or Monday morning to make sure I’m focusing on the right activities to hit my larger goals. It’s a killer system, and although it does require a lot of work, it keeps me focused and acts as my fail-safe for my terribly flawed memory and ADD brain. Curious? Check it out here: https://www.omnigroup.com/omnifocus/
3. Eat. Move. Sleep.: If you need more information, Tom Rath has you covered. Read his book. Yes, we all know we need to do these things, but sometimes, it helps to just be told. I’m starting his 30-Day Plan just to re-up — download it here for free.
4. Be good to people and make sure you have high Emotional Intelligence (EQ). Here’s another book for you––this one totally saved my career. Emotional Intelligence 2.0.
There is a lot of work ahead. Sometimes, it’s going to hurt. And when it does, well, thank the heavens for motivational YouTube videos. Here is one of my new favorites: Contenders By: Mateusz M