I spent nine years at Apple. It’s the place where I finally grew up. I wasn’t just managing a team anymore. I was leading hundreds, thousands of people. It was a profound shift in my career and in who I was. After a decade of failure, I finally made something—actually two things—that people actually wanted. I finally got it right.

But it didn’t feel like success at first. Or even in the end. It was still work, every step of the way.

I’ve seen way too many people come out of the corporate world, decide to start a company, and be completely unprepared for what it takes. If they’ve never been on a small team starting from scratch, they’re often a fish out of water. They spend too much money too fast. Hire too many people. Don’t put in the time, don’t have the startup mentality, can’t make hard decisions, are buried by consensus thinking. They end up making mediocre products or

nothing at all.

Don’t let that be your story. If you want to start a company, if you want to start anything, to create something new, then you need to be ready to push for greatness. And greatness doesn’t come from nothing. You have to prepare. You have to know where you’re headed and remember where you came from. You have to make hard decisions and be the mission-driven “asshole.” [See also: Chapter 2.3: Assholes: Mission-driven “assholes.”]

So do the work. Know what you’re getting into. Trust your gut.

And when the time comes, you’ll be ready.

Even when we accepted a candidate, there was always an awareness that nobody is perfect. There were always critiques, challenges. So it was the hiring manager’s job to understand potential issues from the outset, talk them through with leadership and the candidate, and commit to coaching their new team member through those challenges.

There was no mystery, no black box. Everything was on the record. Everyone knew what to expect.

Then we committed. We hired them. And despite any concerns, any potential areas for improvement, everyone started with 100 percent trust. Once you assess someone thoroughly, check references, and decide to hire them—you also have to decide to trust them. You can’t start with zero trust and expect someone to prove themselves to you.

But more often the real shock of growth is that over time you’ll bring on people who are just okay. Relative to the amazing people you brought in early, they’ll seem unimpressive. Mostly fine, good team players, get the job done.

And that’s not the end of the world. As the company expands, you need all kinds of people at all kinds of levels.

You can’t wait for the perfect A+ candidate to appear for every single empty slot. You need to hire. The best of the best don’t always want to join a big team, or they’re tied up in another job, or you can’t afford them or give them the titles or responsibilities they want.

And sometimes the people you don’t expect to be amazing—the ones you thought were Bs and B+s—turn out to completely rock your world. They hold your team together by being dependable and flexible and great mentors and teammates. They’re modest and kind and just quietly do good work. They’re a different type of “rock star.”

By far the hardest part of growth is finding the best people—in all their different incarnations—trusting your team to hire them, then making sure they’re happy and thriving.

I was also told that a brand-new CEO shouldn’t be trying to make huge acquisitions. I was “crazy,” as one of our investment bankers put it, because the numbers would never work out and this was an impossible “sale” to the street.

The banker had a point. It’s true that on paper the deal didn’t make obvious sense. But I felt certain that this level of ingenuity was worth more than any of us understood or could calculate at the time. It’s perhaps not the most responsible advice in a book like this to say that leaders should just go out there and trust their gut, because it might be interpreted as endorsing impulsivity over thoughtfulness, gambling rather than careful study. As with everything, the key is awareness, taking it all in and weighing every factor—your own motivations, what the people you trust are saying, what careful study and analysis tell you, and then what analysis can’t tell you. You carefully consider all of these factors, understanding that no two circumstances are alike, and then, if you’re in charge, it still ultimately comes down to instinct. Is this right or isn’t it? Nothing is a sure thing, but you need at the very least to be willing to take big risks. You can’t have big wins without them.