20 Things I’ve Learned as a Startup CEO

Why Give a Damn:

In 2011, Unreasonable Institute Founder Daniel Epstein asked me to step up as CEO of Unreasonable Institute. I assumed it would be easy. I was wrong. This post outlines 20 things I’ve learned in the two years I’ve been CEO.

The author of this post, Teju Ravilochan, is co-founder and CEO of the Unreasonable Institute.

In the fall of 2011, I assumed the coveted title of CEO. “Oh boy!” I thought. “What a remarkable chance to shape the direction of something that I believe in so much!” And it has been that. It has also been the most humbling, overwhelming, and remarkable challenge I have ever taken on. The post below, addressed mostly to myself as a reminder, is a summary of some of the lessons I’ve taken to heart in my brief experience as CEO.

1. This is really hard. When you read stories of great startup founders, you think it looks easy. That’s because you don’t know the whole story. This isn’t easy. This is damn hard.
2. Your job is do three things, and three things only, really well. Unreasonable Fellow Daniel Rosen told me that these are the three core responsibilities of a startup CEO. 1) You’ve got to lay out the vision, 2) build a team more capable than you of getting you there, and 3) wrap as many people and resources as you can around that team to support them (e.g. salaries, healthcare, coaching, emotional support, etc.)
3. “There are no maps.” Fellow Unreasonable.is Scribe and Unreasonable Mentor Pascal Finette told us this very clearly. Being a CEO is like anything else (being a parent, chef, artist, writer…). Other people can tell you what’s worked for them and it’s okay for you to listen. But at the end of the day, you’ve got to figure out your own style. You’re not Steve Jobs. That doesn’t mean you’re not as capable as him. It just means that he was a different human being. He had to be the kind of leader that he had to be. You’ve got to be the kind of leader that you’ve got to be.
4. It’s okay to have doubts. The story you hear is that you’ve got to be the number one believer in your venture and in yourself. I think that’s true. But that doesn’t mean you’re not allowed to have doubts about both. Martin Luther King, Jr. was full of self-doubts and fears that the movement he was spearheading wouldn’t succeed. . Unreasonable Mentor and .is Scribe Chris Yeh writes that everyone feels like an impostor. Only one kind of person has zero doubts: people who are lying, most likely to themselves.
5. “Strive not to be a man of success, but rather try to become a man of value.” –Albert Einstein. Unreasonable Mentor Rafe Furst, a World Series of Poker Champion, once taught us his principles to playing Texas Hold ‘Em. One of the things he told us is, “A lot of people think that poker is a game of luck. They’re right. You can’t control the cards you’re dealt or the cards anyone else gets. But the best players win 80% of the time. Why? Because they make the right decision for the right reasons. They know when to fold, when to call, when to raise.” I’ve taken this lesson to heart. We can’t control whether or not the world changes because of us, but we can work, day in and day out, to live our values. We can know when a situation demands honesty, when it demands forgiveness, when it demands loyalty. And the pursuit of living values in those small moments, in my opinion, is what culminates more consistently in success.
6. Forgive yourself for failing to live your values. . It’s easier said than done to live my values. And I’ve failed to live them many times. I’ve hurt my teammates. I’ve had people leave this team because I didn’t live our first value of “treating them like the Messiah.” I may not have forgiven myself for some of these mistakes. But my teammate Banks Benitez reminded me that, “Values are about posture, not position.” You fail to live them sometimes. But the real test is what happens when you realize that you’ve failed at them.
7. If you achieve anything, it will be because you have a great team. Stories glorify the lone entrepreneur, out there defying failure, confident in spite of skepticism, relying on their will and wits alone to get past impossible odds. But in reality, no great human achievement has come to be without teams. The most important, and hardest, role of a CEO is to build a phenomenal team, keep that team, and recognize they are the reason you achieve any progress..
8. Expect pushback, especially if you build a culture where others have voice. You want people on your team to have a voice? You want to have transparent conversations? Then expect a lot of pushback. Your teammates have their own opinions and they certainly don’t line up with yours a lot of the time.
9. Assume positive intent. Know that when your teammates do push back, they are coming from a place of wanting to make the organization better. Assume that. Try to understand why they think this is the best way to make the organization better.
10. It’s okay to say that you don’t know. I don’t know the answer to most of the questions that my teammates ask me. Or to the questions that we need to have answers to to move forward as an organization. It’s a startup. No one knows. No one has ever done exactly what you’re doing before. That’s why you’ve got to rely on an ability to self-correct if you’re wrong, get input from experts, and experiment.
11. It’s okay to say you’re afraid. “Courage is not the absence of fear but rather the judgment that something else is more important.” –Ambrose Redmoon.
12. Your job is to have hard conversations. “I want you on my team.” “You’re exactly the kind of person we want on board as an investor.” “What would it take to convince you to join us?” “This isn’t working out.” “We’re not going to hit our milestones this quarter.” “We can’t give you a raise.” “We have 3 months of cash in the bank.” “I was wrong.” Your job is to define reality and deal with it. You don’t deal with it by painting an overly rosy picture of what’s going on. You call it what it is. And then you tell people how you feel about it. And you build a plan. And you do it. And you mess up. And you keep pressing on. But it all starts with having those hard conversations.
13. Your job is to take responsibility. When things go wrong, you’re held accountable. You can make excuses, or you can take responsibility. I sometimes fail at this, but I so admire the leaders who take responsibility, like Groupon Founder and former CEO Andrew Mason. When he was fired, he showed the kind of person he was by taking responsibility in this public letter to his entire company.
14. Admit that you need help. One person can’t shoulder all the challenges of being a leader. I’ve found that I need a lot of help. I try to meet with our Mentors, Board Members, and my leadership coach as often as I can. Without them, I wouldn’t be able to navigate the complexity and challenges of this work. As hotelier and legendary CEO Chip Conley once said, “Being a CEO is not about being superhuman. It’s about being super human.” That means being vulnerable enough to ask for help.
15. Tell the truth. Especially to yourself. If you bullshit yourself, over time, over time you lose yourself. To your team, explain why you make decisions the way that you do. You can get away without explaining your decisions, but over time, you’ll lose people. It’s a hard thing to tell the truth. But people will respect you for it. They’ll trust you for it.
16. Take care of yourself. Get enough sleep. Exercise. Spend time with loved ones. Read. This is one of the biggest mistakes I made early on. I felt like I had to work 14 hours a day to stay on top of everything. But I was doing my team a disservice. Sleep-deprived, I became impatient with their questions and irritated by their requests for help. So much of my job is about being available to support my team. And when I wasn’t taking care of myself, I couldn’t be there for them.
17. Communicate with your teammates. One-on-one. Often. One of the best things I’ve learned is to create a space to do one-on-ones with each of my teammates. It’s a chance for them to bring up concerns, offer suggestions, ask questions, discuss how they’d like to grow,and voice whatever else is on their mind. Without this space, and without it regularly, even if you’ve got an “open door” teammates won’t often come to share these things with you. VC Ben Horowitz talks about how important one-on-ones are and how to have effective one-on-ones in this post.
18. Acknowledge your limitations. Your team will respect you for letting them know your limits. I’ve learned, from Daniel Rosen, that I can’t really manage and deeply care for more than 5 people. It’s too hard otherwise. I tried to manage a team of 11 during the 2011 Summer Institute and I failed miserably. So this year, my teammates Verity Noble and Banks Benitez, stepped up to lead new summer staff, while I focused on core staff. And our summer staff had a much better experience this year than last year.
19. Your Title Doesn’t Earn You Respect, Your Actions Do. Everyday, I feel so lucky to be able to support my team and build toward our vision. I feel privileged that I have a voice that others are willing to listen to. I am grateful that people take me seriously. But at the end of the day, I’ve learned, that the “CEO” title only buys me that respect for a little while. It’s how I live my values, how I care for others, and how I serve our company that really earns that respect.
20. You have a boss. Just because you can call the shots doesn’t mean you reign supreme. You are accountable to your customers and to your team most of all. If you let them down, you won’t have your job (or perhaps your company) much longer.

Call to Action:

These are learnings from my journey, but I would love to hear and learn from what others have discovered about being a leader in the comments section. Please do share!