How I’ve Focused My Time and Energy While Scaling A Company

As a company grows in size, the job of the CEO changes completely. That sounds obvious in the abstract—the job of CEO for a 5 person company is vastly different from 10 people, 20 people, and so on—but it’s actually a much more difficult thing to do in practice. 

It’s important that leaders recognize this and lead in a way that’s appropriate to your company’s stage. Bad leaders want to make themselves irreplaceable. Good leaders replace themselves with those more capable. Growing as a CEO means leaning into this. It means understanding that the CEO job is effectively an anti-job: to continually put oneself out of work to gain compounding leverage. 

This doesn’t just apply to CEOs. I’ve seen all great leaders adopt this mentality: They push for delegated greatness. They don’t take pride in what they themselves accomplish. Instead, they take pride in what their team accomplishes. 

When companies are tiny, a CEO usually has key areas where they’re tactical. For instance, when Bolt was tiny, I was its first engineer. Soon, we hired exceptional engineers who did not need me. I managed the engineering team until we hit 10 people, and then I transitioned away from engineering and into sales. 

Scaling from 1 to 50 people followed that familiar pattern:

1. Get hands-on to solve a company problem
2. Hire great people to take the reins
3. Let them take the reins and go solve the next problem

When Bolt was ~50 people, I stopped step 1 of this cycle and moved into pure management. Up until that point, the culture took root more naturally. As the CEO, I was in the trenches with the team. But once we reached a certain scale, it was hard to keep a pulse on the day-to-day—to both execute effectively and manage capably. Recently, I moved to Executive Chairman—in part as a way of further moving out of the trenches and into a position in which I could think about the big transitions and horizons for the business.

Making Culture Conscious

Those shifts are why institutionalizing culture becomes paramount. At Bolt, we wrote a culture playbook when we reached 10 people, and we kept making incremental changes to the playbook as we grew. Then we hit a snag: The culture started to lose coherence at around 50 people, and we needed a full revamp. 

That’s when the CEO job changed. After 50 people, the CEO becomes less of a Doer and more of a Thinker. It’s at this stage that a CEO can really lean into vision. The team has enough momentum and resources to accomplish big things, and so at this point, you can start dreaming big. 

Inner work

Then another challenge comes up: After 100 people, it becomes hard to remember everyone’s name at the company. Until that point, I knew people intimately—I knew everyone! This is when you need to start thinking deeply about your influence, because it becomes less direct and more abstract. What values do you convey? What statements do you make? How do you come across? 

If I’m being honest, it’s at this point that a leader’s flaws will really start to flare, and I know mine did. It’s easier to cover them up with fewer people depending on you. You now have seasoned executives, teammates, and investors who hold you to a high bar. It becomes clear when you’re disappointing them. 

As Bolt surpassed 200 people, I started to recognize the need for inner work. Seasoned executives want to work with someone they can trust, and given that I was in my mid-20s at the time, I had to mature quickly, but to do so without losing my edge and my personality. This inner work has continued to this day, and I spend a good chunk of my time on it. It includes yoga, meditation, therapy, and writing. These tools are critical, and when I’m not working, this is typically what I spend my time on. 

The critical lesson

The most important lesson I’ve learned through this all: Follow your gut. It has all the answers. It also has all the problems: if it’s telling you something is wrong somewhere in the business, don’t ignore it. 

The second most important lesson: Have fun and keep it playful. If you don’t, things will get really weird. It’s easy to become so serious in business that you forget about fun—but it’s vital not just for you but for your team. A CEO that is dour will build a team that becomes dour. 

And that’s it! Your job as a leader isn’t fixed; it’s fluid. Be the best leader for your company at its current time and place. And be ready to adapt as things inevitably change.