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.

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.

5.6. Death of a Sales Culture

“There is a different model that aligns short-term business goals without neglecting long-term

customer relationships. It’s based on vested commissions.

Rather than focusing on rewarding salespeople immediately after a transaction, vest the commission over time so your sales team is incentivized to not only bring in new customers, but also work with existing customers to ensure they’re happy and stay happy. Build a culture based on relationships rather than transactions.

Here’s how to set it up at your company:

1. If you’re starting a new sales organization, do not offer traditional monthly cash commissions. It’s best to have everyone in your company compensated in the same way—so offer salespeople a competitive salary and sales performance bonuses of additional stock options that vest over time. Stock provides a built-in incentive to stick around and invest in long-term customers who are good for the business.

1. If you’re trying to transition to a relationship-driven culture, you may not be able to kill traditional commissions right away. In that case, any stock or cash (stock is still preferable) that you give as a commission should vest over time. Pay 10–15 percent of the commission at first, then another tranche in a few months, then another a few months after that, etc. If the customer leaves, the salesperson loses the remainder of their commission.

1. Every sale should be a team sale. So if you have a customer success team (the team that

actually delivers, sets up, and maintains whatever is sold to the customer), then it should sign off on every deal. Sales and customer success should be under one leader, in the same silo, being compensated in the same way. In this setup, sales can’t just throw a customer over the fence and never think about them again. If there’s no customer success team, then sales should work very closely with customer support, operations, or manufacturing—create a board of people to approve each commitment.

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.

An identity crisis knocks a company’s compass off kilter. It clouds its people’s ability to make clear decisions, to choose which route to take, and to allocate the proper resources. How can you hire the right people if you don’t know what you’re hiring them to do? How do you know which projects and products to support if you don’t know how they will ultimately fit into the whole?

Almost every leader will say that their lodestar is defining their business focus, which comes down to what you can do to build long-term value. “If anything, what the last few years have taught us is that building long-term value is critical for any company,” says Dave Peterschmidt. “If the company is going to be in there for the long haul, it has to understand the core value it brings to the market and the reason for its existence in a crowded marketplace. Then you can do an assessment to get the company tracking toward long-term values.”

Think of that assessment as conducting a reality check of the operating environment. If you want to get the company tracking toward long-term value, consider what conditions pertain that will help or hinder you. The answers will shape your short-term agenda.