I was twenty-five years old and had never really managed anyone, never built a team. Now I was one of the CTOs in a massive company of almost 300,000 people. I’d experienced plenty of failure, but this was truly a new and exciting set of experiences to fail at. The rush of imposter syndrome was almost overwhelming.

Then they told me that anyone who joined the team would have to be drug tested.

Because in the beginning you’re not going to have HR to help you find and hire a world-class team. You won’t even have a recruiter. For the first twenty-five or so employees it’ll all come down to you and your cofounder—your vision, your network, your ability to convince people that you know what you’re doing. You can lean on your mentors and board (and hopefully early investors), you can put them to work to prop up your reputation, but ultimately you’re selling yourself and your vision for success.

You need a story people can get behind. [See also: Chapter 3.2: Why Storytelling.] People you respect. People who will help you create something great. Your team is your company. And your first hires are crucial—they’ll help you architect what your business and culture will become.

The best way to share and embed cultural DNA is person to person. When you’re growing fast, the new people you just hired most likely have some responsibility to hire as well, so a week of orientation isn’t going to cut it.

If you have fifty people who understand your culture and add a hundred who don’t, you will lose that culture. It’s just math.

So when bringing in new employees—especially execs—you shouldn’t just throw them in the deep end, hand them a branded company notebook, and think you’re done. The first month or two are crucial and should be a period of positive micromanagement. Don’t worry about getting too in the weeds or not giving them enough freedom. Not at first. A brand-new person needs all the help they can get to become really well integrated. Explain how you do things in detail so they don’t make mistakes and alienate the rest of the team right off the bat. Talk to them about what’s working and what isn’t, what you would do in their position, what’s encouraged and what’s verboten, who to ask for help and who to treat with kid gloves.

That’s the best way to immerse someone in the culture, style, and processes of a team. Give them the push they need to start running with the pack rather than leaving them standing on the starting line, reading some docs, hoping they’ll catch up.

Always remember that it’s scary joining a new team. Not knowing anyone. Not knowing if you’ll fit in. Not knowing if you’ll succeed.

That’s why I started doing brown-bag lunches with the CEO. Matt did them too. Every two to four weeks, we’d gather a crew of 15–25 new hires and existing employees and have an informal lunch. We tried to cross-pollinate different people from different groups, a good mix from around the company. No managers, no executives, no keynote presentations. Just an

opportunity for them to get to know the bogeyman at the top and for me to get to know them. They asked me about our products, our policies, about me and Matt and our history at Apple. About why we didn’t allow massages, about why we had so many code names. [See also: Chapter 6.4: Fuck Massages.] And I asked about what they were excited about, what they were working on, why they joined.

It was my chance to highlight why their role was important, to talk about how their team’s goals powered our company goals, about our culture and our products and new projects and what was going right and what wasn’t. New employees had the chance to come directly to me with their questions as well as meet existing employees who were already steeped in our culture, who could help them and lead by example.

Any employee could come to five lunches a year. And each lunch was a cultural inoculation, a vaccine against indifference and apathy, against thinking that what you do doesn’t matter and that nobody at the top knows who you are.

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.

So the dating phase of any potential acquisition is crucial. You have to check the sink for dirty dishes. You have to spot the toenail on the dining table. Look at the reporting structure and the way they hire and fire employees. Dig into what perks everyone gets. Talk about management philosophy. Make concrete plans for exactly what’s going to happen postsale.

Are you going to integrate or keep your cultures separate? What will you do about overlap? Where will this team go? Who will work on this product?

But always know that you won’t be able to predict the future. Things will change—maybe in your favor, maybe not. And so, eventually, you just have to do it. Sign on the dotted line. Trust that it’ll work out.

My advice is to always be cautiously optimistic. Trust, but verify.

Assume people have the best intentions, then make sure they’re following through on them. And take the risk. Leap. Buy the company. Sell the company. Or do neither. Just follow your gut and don’t be scared (or, rather, be scared but make the decision anyway).