Episode description

Experimenting with a new format with my pal Alex Hillinger. We’re planning to do a few of these so you can hear a format where there is more banter and storytelling. A little sneak behind how the sausage is made. Let us know what you think. 

A great idea is transformative by nature and what comes next either supports making it or breaking it. When a good or even great idea presents itself, it’s not enough on its own. We need certain boundaries and constraints that drive the idea forward and we probably need some luck too.

When you’re getting an idea off the ground it’s common to spend a lot of time preparing for it. I’ve had ideas where I spent way too much time in the planning stages. I call this insecurity work. My friend Alex blatantly describes it as procrastination. Alex Hillinger is known as an unconventional strategist, he says there’s more to it when it comes to launching a great idea and having it work out. You need a great idea, and you need to take action on it, and you also need constraints and boundaries to do that effectively.

Alex knows what he’s talking about. He works with the most innovative entrepreneurs, artists, and athletes in the world. Through his work, he’s pioneered new business models, grown great brands, and collaborated on projects that changed the world. He’s an advisor to Google’s Crisis Response team and CreativeLive’s executive team. Alex has a lot to share with us. His experience in helping people generate game-changing strategies and growing engaged communities lends to the conversation we have. We explore both the strategic side and the emotional side of our creative pursuits.

Highlights from our conversation:

• Get to know Alex Hillinger, who he is, and how we know each other. We go way back multiple decades, so we’ve got a lot of stories working and spending time together. 10:33
• 10% Planning, 90% Doing. The dominant mode for most people is that they way over-index on all of the planning and the insecurity work instead of just acting. 35:21
  Constraints are Required. Freedom and creativity do need boundaries to help them be successful. 37:21 
• Everything is a Remix. 54:09
• Success is a low bar. We should really be shooting for fulfillment. 01:11:44

Enjoy!