How to Be a Top 1% Startup CEO
Learnings from Ben Horowitz, Matt Mochary, and more
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For this week’s post, I researched what makes up top startup CEOs and identified 12 traits.
Below you’ll find what they are, and how you can embody them 👇️
Read time: 5 minutes
📖 What I’ve Been Reading
There’s a lot of noise out there about AI right now. Everywhere you look on Twitter, someone’s posting ChatGPT threads or claiming that it passed the bar exam.
Alex does a great job distilling the noise around AI into insightful weekly pieces. He’s also a founder, and he writes with a founder’s perspective.
I’ve been enjoying his newsletter for a few months now, and so have over 20,000 other readers:
How to Be a Top 1% Startup CEO
Set (and Complete) a Top Goal Each Day
Since CEOs have context across the entire business, it’s incredibly easy to get caught up fighting a long list of small fires rather than making progress against the highest leverage tasks that only a CEO can do.
Don’t let this happen to you.
CEO coach Matt Mochary recommends blocking 2 hours on your calendar in the morning every single day and devoting that time exclusively to your single most important goal for the day.
Keep track of how many days you successfully do this and hold yourself accountable.
Run Towards What Scares You
Every startup has problems, and most CEOs know where the problems at their startup are.
Bad CEOs ignore them and hope they get drowned out by the other, good things going on at the company.
Good CEOs run right at the highest impact problems as soon as they notice them, to avoid allowing them to grow over time.
The problems that scare you are the ones you need to spend time on, even if they delay other progress or derail plans.
Sometimes things don’t go according to plan.
Maybe you failed at raising the amount of capital you were hoping to bring in, or closing a big partner.
Maybe you’re going through something serious in your personal life that’s slowing you down.
It’s important that you humanize yourself to those around you and be transparent with your struggles and failures.
What’s more important than being perceived as an infallible leader is for your team to be able to understand your decisions and behavior. Without context, that’s impossible.
If you want team members to stick around, and investors to have your back, there’s no other way.
Know What to Do (Or How to Figure it Out)
CEOs don’t need to have all the answers. Regardless of whether a startup is growing fast or struggling, they probably won’t.
But great CEOs are relentlessly resourceful, as Paul Graham would say.
If you don’t know how to do or fix something, your first instinct should be to find the most efficient path to the answer (rather than frustrated or embarrassed that you don’t know it yourself).
a16z says this is the first thing they look for in CEOs they fund.
Be Hyper Organized
Startups are chaotic. In the early stages CEOs often deal with more chaos than anyone else, but everyone on the team is feeling it.
Where a CEO can uniquely add value is by having a good understanding of the business at any given time.
You should know how things work, be on top of current issues the team and business are facing are, what you’re doing to solve them, and more.
Also — you should always be available to respond quickly.
Build a system that lets you be at inbox zero consistently. I recommend Mailman as a starting point. It lets you set dedicated times for emails to be delivered (and whitelist certain addresses).
Over time your team will notice and their faith in you as a leader will grow.
Do What You Say You Will
Related to the last point, it’s incredibly easy for the CEO of an early stage, fast moving startup to forget to email someone back or write up a doc that was mentioned in passing by a certain time because they got pulled into something else.
However, letting this become a habit will severely impact the trust you have with core stakeholders.
Resist the urge to overcommit your time, or paint too rosy of a picture of what’s on the horizon. This is true for your communications with your team, investors, partners, and users.
A good reputation leads to trust which leads to a healthy team and business.
You can’t coast along as a CEO.
You need to drive your startup forward. You need to lead. Otherwise, no one will.
In practice, this means being someone that inspires your team.
It’s true that leadership can manifest itself in different ways. I’m not saying you need to be Tony Robbins, but sitting back and hoping your team is inspired isn’t going to cut it.
Early stage CEOs should know everything about their business but they can’t do everything themselves.
Set clear areas of ownership with your team, and make sure their plates are full of important work. Delegate what you can, when you can.
To do this effectively, it starts by hiring people you can trust. And, then, trusting them (micromanagement defeats the point of delegating).
I know this can be tough, but it’s important. There’s no other path that doesn’t lead to your own burnout.
Consistently and Actively Manage Your Own Psychology
Being a CEO is lonely. Being a CEO of a startup is even lonelier. And the only true way to learn how to do it is to do it.
The worst part? When things go wrong it’s your fault.
I could do an entire post on this topic alone, but the takeaway I’ll leave you with this time is something Ben Horowitz wrote about:
When you’re learning to drive a racecar around a corner, you’re told to look at the track — not the wall. If you look at the wall, you’ll drive right into it.
Don’t drive into the wall. Whatever you need to do to keep your eyes on the track, do it.
Startups need to move fast; it’s their only true advantage over incumbents in most cases.
You’re not always going to have all the data you need to make a decision, but getting 70% of your decisions correct quickly is typically a net positive for a startup relative to getting 80-90% correct but slowly.
This is counterintuitive. It’s been one of my biggest learnings as a founder, personally.
Elon Musk is a great example here. He said Twitter will do "lots of dumb things” in the first few months of his takeover. As long as you’re working from first principles then you’re doing alright.
Just make sure you don’t make big, one-way door decisions impulsively.
This may seem obvious, but let me be clear with why this is still worth mentioning.
As a CEO, you set the pace. Your team will respond to your habits and behaviors. You work harder, they’ll work harder.
It’s not just about your own output — having your team see your passion and dedication will be a multiplier across the entire output of the business.
So, yeah, work hard. I don’t know a single successful CEO who doesn’t. That’s what you signed up for.
Startups have 4 key stakeholders (in no particular order):
Users / Customers
The CEO is solely responsible for creating and maintaining strong relationships with all 4, and balancing their own and their team’s time appropriately.
Good startup CEOs understand that good relationships with all 4 are required for a startup to operate efficiently, and genuinely invest time and care into each.
You can ask me any question here that you’d like me to cover in a future newsletter issue by replying to this email.
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