What to Expect When You're CEO of a Successful Startup

Leading a startup is analogous to being a first-time parent. You can read books and articles, you can talk to others that have been through it, but no one can ever fully determine what it’s like until he or she experiences it first-hand. Since joining Sumo Logic as a first-time CEO in 2012, it has been quite a ride.

Boiling down the experience of my first two years as a CEO of Sumo Logic, I have found eight tenets that I want to share:

1. Few will understand your process or state of mind. Many will try, but few will succeed in understanding the investment of time, emotion and energy associated with leading a start-up company. Though it is difficult, accepting the isolated nature of being a leader is important. This acceptance will embolden you to move forward with your work rather than exert energy to seek the understanding or acceptance of others. It’s lonely. Get over it.

2. Listen to your gut. Entrepreneurs receive a landslide of advice from well-meaning colleagues, friends and family  – even total strangers offering advice in columns such as this one. But, even the best advice can prove worthless when it is heeded in the wrong situation. So while it is important to appreciate good advice, it is also critical to trust your gut. Often your first idea is the best and your first inkling is correct. Furthermore, if things go wrong – you will have no one to blame but yourself.

3. Ban the phrase “other people’s money (OPM).” Every entrepreneur should always behave as if the money they are spending is theirs. People often become lackadaisical when they internalize that they are using OPM. And a startup cannot afford to be frivolous with resources.  

4. Believe in karma. I’ve seen many people sabotage their careers with arrogance. You never know how people will enter, exit and re-enter your life. Especially in Silicon Valley, where the entry level engineer today is tomorrow the startup founder on the rise. It is important to plant your feet firmly on the ground, keep a level head and be courteous to everyone you meet. As the old saying goes, “Keep your words sweet, you may have to eat them one day.”

5. Listen more than you speak. You don’t learn too much while you’re speaking. However, I learn many things during brainstorms with my team. A good leader listens first and speaks last. This will allow you to see all sides of a situation before weighing in. Silicon Valley is home to some of the brightest people in the world. What is the point in hiring them if you do not make time to listen to their ideas?

6. People matter. Though technology is a focal point of many businesses, people are still the foundation of the business. People are still the decision-makers. So it behooves the leader of a company to find the best people and create an environment they want to come to every day. Balancing the needs of people with the needs of the business will go a long way when scaling the business.

7. Your investors are a great resource. Working with high-quality venture capitalists (VCs) can change everything for a startup company in Silicon Valley. Their access to customers, top talent and strategic partners is invaluable.

For Sumo Logic, our VC partners, Greylock, Sutter Hill Accel and Sequoia, have been instrumental in bringing us amazing talent and marquee customers. Venture capitalists make a living on identifying the right markets with the right teams with the right momentum. Markets and momentum can swing though, so be sure to secure funding when you are on the way up.

8. Belief in your mission inspires. As unoriginal as it sounds, you must believe in yourself and your company more than anyone else. If you are not passionate, your employees, investors and customers will not get passionate about your company. In many ways, enthusiasm and belief in your vision is the most important asset of any entrepreneur.

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Successful Entrepreneurs

There is a saying that there are only three types of people in the world: those who watch what happened, those who wonder what happened and those who make things happen. 

Entrepreneurs fall into the last category, of course. They are change agents, people who don’t see the world as it is but as it could be. Entrepreneurs don’t sit on the sidelines and wish for a better world. Rather they go out and create it. They don’t wait for things to be different. They are the difference.

Being forward thinkers, entrepreneurs continually push themselves to become better and do better. They are game changers. They ooze confidence and inspire greatness.

Today is a great day to become an entrepreneur because the price of admission into this elite club is free and yours for the taking.

Do you really want to succeed as an entrepreneur? Follow these five steps and you’ll be well on your way to developing the leadership qualities it takes:

1. Willingly fail and reflect. “Ever tried. Ever failed. No matter. Try again. Fail again. Fail better,” goes Samuel Beckett's line. It's not always easy, the trying again part.

Another important thing is taking time to reflect on what went wrong. In the book The Call of Solitude, Ester Schaler Buchholz says, “Others inspire us, information feeds us, practice improves our performance, but we need quiet time to figure things out.”

In his book, Fail Up, radio broadcaster Tavis Smiley recalls lessons he has learned through reflection. He sheds light on these so-called failures that were, in hindsight, his best teachers.

You’ll only learn by failing over and over again. When you do this, you’re able to grow. And in spite of life’s inevitable setbacks, you’ll come out the victor.

2. Embrace and confront your fears. According to author Brendon Burchard, fear can be categorized in three ways, which all relate to pain. The first is loss pain, which happens when you’re afraid to move ahead because you fear you’ll lose something valuable.

The second is process pain, which inevitably occurs every time you try something new. You have to go through the process of learning to deal with it.

The last is outcome pain. This involves not getting the outcome you desired.

Burchard insists that people need to overwhelm their fears. Just as an army invades its enemy from every side, a person should do the same with fear, attacking it from every side, as if going to war. 

For Shark Tank host Barbara Corcoran, public speaking was her Achilles' heel. But she overcame it by going to war. She volunteered to teach a real estate night course in front of a small group of students to overcome her fear.

3. Practice self-discipline. This is the ability to delay instant gratification and the ability to work hard now to reap benefits later. When Academy Award-winning actor Jamie Foxx was a boy, hisgrandmother routinely made him take piano lessons even though all he wanted to do was go outside to play. He had no idea that those lessons would lead to his eventual success. To this day, he continues to hone his craft and disciplines himself to practice playing the piano for two hours many a day.

No one sees the years of hard work you might put into an endeavor. They only see the outcome. If you want to reap the rewards of tomorrow, you must put in the work today.

4. Get some sleep. Shortly after the debut of her eponymous news site, Arianna Huffington collapsed from exhaustion and lack of sleep. She’d been working 18-hour days because she was so committed to growing her company. When she collapsed, she hit her head against a desk and found herself lying in a pool of blood.

In her book Thrive, Huffington details the ordeal and says it was a painful wake-up call. She knew she had neglected sleep and took steps to correct it.

When you get the sleep you need, you’ll feel more energized, charged and ready to tackle any problem entrepreneurship throws your way.

5. Give to others. In his book, Give and Take: Why Helping Others Drives Our Success,Wharton Business School professor Adam Grant teaches the idea of generosity in a professional setting. 

For centuries, people have focused on the individual drivers of success: passion, hard work and sheer will. But things have changed. Success is increasingly dependent on how we interact with others and how much we give them.

According to Grant’s research, the most successful people are those who consistently give. Grant takes this to heart so much that he not only puts in long hours as a professor, but also as many and sometimes even longer hours giving and helping others. 

That ancient book, the Bible, was right all along: Happiness comes from giving.  

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