Lessons Learned in Leadership

Our generation is starting to embrace startups and we love the idea of being a boss. Most of the people I know are working on something on the side, or hustling full time for their business. I bet if you’re between 25 and 35, you can easily name 5 people who fit into this bucket. As my former boss puts it, “startups are the new smart person’s lottery”.

If you are one of those pursuing the entrepreneurial path, you will have probably heard the phrase “it’s not about the idea, it’s about execution”. Before starting my business, I thought that statement couldn’t be correct. It is so hard coming up with a good idea. You want something profitable, probable and aligned with your passions. It was only once I found the idea I liked, that I realized how much harder the execution part of it was.

When you think of execution, you usually think about building a team, creating the physical product, and selling. While those are all correct, the biggest understatement is leading. Executing means leading the team down a path they have never travelled before. This is where being an inventor, and being a founder/CEO are very different. Over the past few months, I wrote down some of my more important leadership lessons to date.

I am CEO, Bitch

In a startup, the position of CEO is usually given to someone who has thought of the idea and put the team together. That may temporarily earn them the CEO title, but it does not grant them this position daily. Every single day a CEO has to earn his right to lead. Every single day a CEO must prove why he is in command of this business. Every single day a CEO must be the best employee in the company. That is the choice you make if you choose to lead. I am sure the same rules apply in larger companies if you’re a manager, boss, vice president, etc.

The reason this is an earned title on a daily basis is because of trust. Employees, customers, investors, partners, and cofounders all trust the CEO to know what they are doing. In most cases, they are blindly following the CEO into the dark. If at any moment there is doubt about the personality, work ethic, or motivation of the person in charge, people will leave. These people may not physically leave, but they may check out, or may be less motivated.

You Can Put the Blame on Me

Part of earning the CEO title is accepting responsibility. Many times the hiring, the product and marketing decisions, and the overall strategy come from the CEO. If there are bad decisions made in that process, there is no one to blame but the CEO. For example, if you are the CEO and you end up hiring a bad software developer and the website doesn’t work. Is it the software engineer’s fault? Probably yes right? This is true of corporations, where if someone makes a mistake, it is their fault. In a small startup team, that is not the case. I’d argue it is actually the CEO’s fault, not just for hiring the wrong employee, but also for a list of other reasons. Some of these reasons include; not checking the website after launch, creating unclear metrics and incentives for the employee, and setting a poor standard of quality work. As the CEO, it is your fault.

This example is magnified through a customer’s perspective. If your product doesn’t work or looks terrible, they won’t look up the developer or designer. They will say you, the CEO, made a terrible product.

Like Father, Like Son. Like CEO, Like Company.

CEOs build the environment for their company to thrive. As a CEO, how you work, when you work, and what you do for fun, are all reflected back on your team. The entire culture of the company stems from the CEO, just like the entire culture of the family stems from the parents. Employees and cofounders always look up to you to see how you function and what your flaws are. If you don’t give it 100%, the team won’t. If you’re late to work a few days, the team will not respect coming on time either. All eyes are on you as the CEO, all the time.

Many people are okay with setting this culture and being tested constantly. They have been older siblings, or held leadership positions in the past. For people that have not experienced this before, the task can be really challenging. It takes maturity and lots of thought to decide what kind of culture and environment you want to set. I’d argue 25% of your time should be spent on this as your team grows past 2–3 people. If executed poorly, culture can be the downfall of a company, and in larger businesses, usually leads to a change in management.

Your Time is Not More Important

CEOs of large companies always have secretaries managing every minute of their time. I recall my former bosses having 15 min slots booked so they would be as productive as possible. As a startup CEO, you know more about the business than any of your team members, so your time is likely worth more. It also makes sense that the more time you put towards executing your business, the more it will grow right? Not necessarily.

Team building takes time. Brainstorming takes time. Reflecting takes time. Team members take time. Each of these things takes more and more of your time when all you want to do is sell or code or build the business. Ironically, time spent doing these other activities might be the most beneficial. Team building helps people know you care about them, as much as you care about the vision. No one wants to work for someone that doesn’t care about them, and caring takes time. People jump to startups because in these small teams they can form bonds and feel respected. Why else would anyone take a salary cut and work longer hours?

Reflecting also takes time and it is what many top CEOs do often. Reflecting means reading and studying the business. It also means thinking about what to say, how to present yourself, and how to constantly evaluate your business. Carving out time to reflect is very important, and sometimes the results can be blogs like this to help others relate.

There are also time wasters like endless meetings or poorly designed brainstorming sessions. Time wasters tend to not only hurt your productivity but can also de-motivate the team. The best way to reduce time wasters is planning ahead, reflecting on similar scenarios, and stopping as soon as possible.

Gratitude is my Attitude

CEO’s feel the extremes of all sorts of emotions. I have felt tons of joy and dealt with lots of loneliness. Small experiences like what your friends and family say, to big moments like being featured on the news; create lots of moments of reflection. The only thing you can control in dealing with these scenarios is your attitude. Sometimes you want to be arrogant and bashful, other times you are terrified and stressed. You find yourself asking lots of questions and constantly pushing forward.

Whatever your state of mind is during these moments, it is important to remember to be grateful. It takes great courage to lead, and building something is a lot of work. Entrepreneurship and ideas are still not praised as they should be, and our society continues to look at failure as a bad thing. Even if the image is changing, progress is slow. If you constantly appreciate the mini miracles you have experienced growing your business, I think it will give you strength to press on.

It’s not about the obvious people, like parents, friends, mentors, employees, customers and such. It’s also about the daily moments, the people holding doors for you, or offering you a late night snack. It’s the customer who calls to give you feedback, but also the stranger who inspires an idea. It’s the combination of all these things that helps you help the world move forward. We forget that sometimes in our daily routines and stressful moments. We forget that we are part of something much larger than us, and any dent we create, is so small and so insignificant, that we’d be foolish not to appreciate how lucky we really are.

Special thanks to Etan, Shub, Justin and the whole MealSurfers team for helping me learn these lessons. This is dedicated to you. Special thanks also to Parth, Sameer, Mina and countless others for sharing your lessons with me. Thanks to Jeremy, Ari, and AK for being great former bosses.