What it’s Like to Date the CEO of a Tech Startup

Let me start by saying that being the CEO of a tech startup is similar to being the parent of a child. As the CEO, your job is to nurture your baby, make sure it has everything it needs to grow, and help it succeed overall. This means that your mind is always thinking about your child and everything that it needs on a daily basis. I may not have a child, but my co-founder has an eight-year-old son, and I have a nine-year-old Shih Tzu, so I do know what the responsibility is like. This can be anything from development (whether Web, iPhone, Android, etc.), marketing, content distribution, business, financial, analytics, management, interns, and the list goes on.

Even though this is our job, it is also our livelihoods. Unlike most people who just have a job, the CEO of a tech startup has to succeed in order to survive. Once you can wrap your head around that, you will be able to start to form a relationship with this person. One of the smartest things you can do in order to date one of us, is to understand this fully. Start by asking yourself (and answering) these questions:

• What triggers our stress?
• What triggers our happiness?
• What are our short-term and long-term goals?
• What challenges do we face every day?
• What do we need help with?
• Which are our busiest and slowest days?
• What do we like to do in our spare time?
• What kinds of food, music, and movies do we like?

If you can answer some of these questions, it will help you be on the same level as us. I know it sounds a little one sided, but trust me it’s not. Here’s why. We are strange animals. Not so much an elephant or a tiger, more like a Komodo dragon. Once you understand our species and learn how to tame us, we will be your best friend. Our time is very valuable to us, and we look at it differently than most humans do. Throughout history, time has been looked at as a commodity that you can’t buy more of. And eventually time runs out and you die. This maybe the case, but we entrepreneurs view time differently.

How much time will it take to launch our product? How much time until we are revenue positive? How much time until we gain critical mass? How much time until we are potentially acquired? These are some of the things we think about along with smaller details on a daily basis. Once things are looking good, the rest of your days on Earth will be exceptionally Utopian. You will have the most fulfilling moments in your life if you decide to take the plunge and share your life with this person.

It’s not that we are narcissistic, because we aren’t, we are just taking care of our child, and to share our life with you (our time), is almost painstakingly difficult because we feel as though we are letting our child become neglected. You’ll find that we are quite quirky people, silly even, but also serious and passionate. You may even enjoy the startup culture and find out that you share the same vision that we do. You will learn a ton, more so than any other job you’ll ever have in your life. Get ready for information overload, but also fun events, conventions, meetups, and trips to places you’ve never been to.

Also keep in mind when you date an entrepreneur, their schedules are quite flexible. This means they will be available for a lot of things that you may ask them to do with you. That being said, don’t get upset if they answer an email or phone call, or have to make a pit stop for a quick meeting. Supporting your partner in all aspects of their company and their life, is what they need right now in order to succeed. If you don’t believe you can do this temporarily while they are growing their company, then look for somebody who has a 9-to-5 job.

So while dating the CEO of a tech startup might be a daunting thought, intimidating, and challenging, it can also be one of the most rewarding relationships you will ever have in your life. Once we see that you are in it for the long haul, and that you truly care about us and what we are doing, we will treat you better than anyone has before. We want to be happy, we want to have a relationship, but we won’t settle for second best. Obviously we didn’t settle for a regular 9-5 job, so why would we settle for a regular person? We seek someone unique, someone who understands that life is more than TV and sports. Show us how fascinating you are and we will praise you for it. Show us how tolerant you are, and we will give you our hearts. Show us how much you support what we do, and we will give you our love.

So fasten your seat belts, be lucky enough to meet the entrepreneur of your dreams, and enjoy the ride!

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Jason Sherman

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