I often encourage my CEO clients to be bored in order to build a billion-dollar company.
Most founders think that's absurd. But there's a single highest-leverage move that makes this possible, and most founders don't fully commit to it.
Get it right, and you can spend real time with friends and family, keep up with your hobbies, work no more than forty to fifty hours a week, take vacations, and still watch your company continue to grow.
Get it wrong, and you're getting Slacked around the clock, working nights and weekends, feeling like the whole thing stops the moment you step away.
And it doesn't come down to intelligence or how hard you're working. Two founders can have both in equal measure and still end up in completely different places.
So what actually makes the difference?
It comes down to one decision that most founders under-invest in, and deprioritize when the pressure is on: building a truly exceptional leadership team, one that can essentially run the company without you.
Most founders know this intellectually. They'll tell you it's a priority. They'll nod when you bring it up. But when you look at what's actually there, it's usually a good team. A very good team, even. Just not a team that runs the company without them.
And the reason isn't that they can't attract the talent. It's that holding a genuinely high bar, and letting go of the people already on the team who don't meet it, turns out to be much harder than it sounds.
You want to hire leaders you genuinely believe would do the job as well as or better than you could. That's the bar I hold clients to. When you do this, you barely have to think about them. All you have to do is set the vision, create clarity around goals, and then they mostly run without you.
Bill Gates famously spent hours each day just reading. That kind of thinking time only becomes available when you have a team you fully trust to handle the day-to-day. Once that team is in place, the CEO's job shifts entirely toward vision, strategy, and the work only you can do.
Most founders don't realize how much it costs them to settle for less than that.
During the 2008 financial crisis, Netflix laid off somewhere between thirty and forty percent of their team. Absolute company performance improved. Not per person. Total. Reed Hastings was shocked.
What they eventually figured out is that talent density is the key to performance. Lower performers aren't just underperforming in their own lane. They're dragging everyone around them. Business school research backs this up: when researchers placed an actor playing a disengaged, low-effort team member into group projects, the whole group's performance fell to match. Consciously or not, people notice what gets tolerated.
Every day you keep someone who doesn't meet the bar, you're paying a cost that doesn't show up on any spreadsheet.
When all the candidates are still candidates, you can compare them clearly. Then you hire someone and your attachment spikes. They're your person now. And there's a tremendous amount of resistance to letting them go. Part of it is that it might signal you didn't do a good job hiring. Part of it is the disruption it would cause. And part of it is genuine empathy for the person.
Over time, a lot of founders start to feel like their team is a family. And when it feels like a family, letting someone go starts to feel like a betrayal. You don't fire family members.
The better frame is a coach and their team. The best coaches in the world genuinely love their players. And they still trade them when the team needs it. That's because the purpose of a family is the family. The purpose of a team is a mission. Your job as a leader is the greater good of the company, which sometimes means making hard choices for individual people. You can love someone and still recognize they belong somewhere else.
Even so, when the moment actually comes, most founders still find a way not to do it. Holding onto someone you should let go is a hero move. You're taking more than your share of responsibility. You're trying to rescue them from setbacks and deny them the growth that comes from facing what's real.
But can you see them as a powerful human capable of being with those feelings, rather than as a victim you need to protect from them? In the short term, yes, it's a hit. They might feel sad, disappointed, scared. Those feelings are real and worth honoring. And they're capable of being with them.
Ask yourself this: if someone offered to go back in your life and remove all your setbacks, all your failures, would you let them? I've asked that question to hundreds of founders. Nobody says yes. Those setbacks shaped you. When you hold on to protect someone from being let go, you may be rescuing them from exactly what they need.
And consider this: if they were truly thriving in the role, you wouldn't be thinking about letting them go. They already know on some level they're not in the right place. Keeping them isn't protecting them.
As I often say to clients: a leader's responsibility is to believe in the greatness of their people. And if you can't, let them go find a leader who can.
Start by going through your leadership team one by one. For each person, ask honestly: do I genuinely believe they'd do this job as well as or better than I could? If you're hedging on someone, that's information worth sitting with.
From there, run what's known as the Netflix Keeper Test, which Reed Hastings writes about in No Rules Rules. The question is simple: if this person told you they were leaving, would you fight hard to keep them? Not would you be inconvenienced. Not would it create a gap. Would you genuinely fight to keep them because they're that good?
When I've asked clients to honestly reflect on that for the folks on their team, often the answer is no for one or two people or more. And they've been rationalizing it.
The distinction that matters here, and this is worth slowing down on, is whether your answer is about the person or the situation. Wanting to keep someone because you'd have a gap, because the search would be painful, because you'd have to carry their work temporarily, those are fear-based reasons. Wanting to keep them because they're truly extraordinary is the real test. If the honest answer is no, you already have your answer.
When you feel resistance to letting someone go, name the fear story underneath it. From my experience, fear makes bad predictions. The three most common ones I hear are:
Often the opposite happens. People step up in surprising ways. Morale holds or even improves because the team already knew the person wasn't performing.
And if the people who might leave were hired by the person you're letting go, remember: A players hire A players, B players hire C players. Sometimes that departure is addition by subtraction.
Building a truly exceptional leadership team is harder upfront. The search takes longer. It's scary when it's taking a while to find the right people. But consider the alternative.
I've seen this movie play out again and again. Leaders build a very good team, but not a truly world-class one, and then spend the next years dealing with the implications. The drama. The constant need to motivate. The feeling that the company only moves when you push it. When you settle for a good team instead of a truly exceptional one, you end up spending your time managing, motivating, and putting out fires.
Eric Ries, who wrote The Lean Startup, sent me an early copy of his new book, Incorruptible. He puts it simply: choose your hard. The hard of holding out for a truly exceptional, mission-aligned team is real. So is the hard of not holding out. I understand the compulsion to settle. But don't.
With love,
Dave Kashen