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This article was published on February 27, 2020

If you want to win everything, you have to be prepared to lose everything

Find your own 'pizza phone number'


If you want to win everything, you have to be prepared to lose everything

Boris is the wise ol’ CEO of TNW who writes a weekly column on everything about being an entrepreneur in tech — from managing stress to embracing awkwardness. You can get his musings straight to your inbox by signing up for his newsletter!

At a dinner I hosted this week I had a discussion about preparing food. I enjoy hosting dinners and regularly cook for a dozen people at a time at my house, and I’ve even at other occasions cooked for groups of up to 150 people. Someone asked me what my trick is and I repeated what I’ve said often, to guests or even my children: The most important ingredient in the kitchen, is the number of the pizza delivery service.

What I mean is: I cook like I have nothing to lose. If half the potatoes burn, I’ll assume the other half taste even better. If everything burns, I’ll order pizza. Nothing lost. This mindset allows me to experience freely and fearlessly.

And this mindset goes way beyond the kitchen. A woman who sat next to me explained how she was successful at her job at a big company. She told me: “I’ve been freelancing for 12 years before I took this job, so whenever I receive pushback to a decision I make — that I believe is good for the company — I simply think: I’m just going to do it and if they don’t like it they can fire me.”

That was her version of the pizza delivery number. Knowing she’d been successful at freelancing allowed her to focus on what was right for the company, versus what she needed to do to keep her job.

There’s a famous story about Apple engineers hiding a Sony engineer in a closet from Steve Jobs, which I can highly recommend you read. Long story short, Steve Jobs wanted to build his own disk drive. His team advised against it, but he was stubborn. So they went along with his plan, but behind his back they worked on an alternative plan. 

When Steve’s plan fell through they told him about their alternative plan, he swallowed his pride and it all ended well. What I absolutely love about this story is that these people cared so much about their mission that they risked losing their jobs over it.

I try to tell this to everybody who works at TNW too. If I’m full of shit, I sure hope people will feel safe enough to simply tell me. That’s not a comfortable place to be in, but it’s best for everybody. It also ensures that you limit office politics and it signals that you truly only care about the mission of the company. It’s what I consider real empowerment.

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