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Should an Entrepreneur Date?

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should an entrepreneur date

Should an Entrepreneur Date?

Love is one of the strongest emotions a human can experience. It’ll have one feeling on top of the world at one moment and down in the dumps the very next. It had us thinking, would a boyfriend/girlfriend help an entrepreneur in their journey? The short answer is yes. The long answer is no.

Why Dating Would Help

Young love is amazing. You find the first love of your life, go to college with them, explore the world and share experiences you’ll remember forever. You don’t think anything can possibly go wrong as you’re madly in love with someone and enjoy every minute of their presence.

When you need some time off from working, you call up your boyfriend or girlfriend and catch a movie or just vent to them about your problems. They’re there for you at the touch of an iPhone.

On the flip side, they’ll keep you grounded and won’t allow you to do anything stupid. Instead of going out that Friday night and forgetting to use a rubber resulting in a You Jr., you would have stayed home and opted for a game night.

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Having someone that you can rely on like this should help you focus on what’s important and allow you to be your best at all times. However, that’s not always the case.

Why Dating Won’t Help

While there are certainly some benefits to being in a relationship as an entrepreneur, we’re convinced that the cons outweigh the pros.

Your significant other may not have as much on their plate as you, so they’ll need you more than you need them. If they’re not an entrepreneur, they won’t understand the 24/7 work schedule you live and will want you to allocate a lot of time with them every week or even day. You end up spending your extra time posted up on the couch instead of working on that idea you have and ultimately don’t become as successful as you could’ve.

Another factor is that relationships are expensive, especially for the guy. Being the gentlemen that we are, we pay for meals, activities, etc.without complaint but it adds up real quick especially in a place like New York City. How are you expected to put money towards a startup or your new business if you’re eating out every weekend and splurging on gifts?

Picture this nightmare scenario: you devote five years of your life to another person and after five years, you find out they’ve been cheating on you for months. What now?

All the time, energy and money you dedicated to this person no longer matters as there’s not a feasible chance the relationship recovers. Julie Deane built a $65 million satchel business in five years. We’re not going to sit here and tell you that if you’re not in a relationship, you can build a $65 million business in five years but we will tell you that you’ll have more resources to do so.


No two situations are the same. An empowering relationship can lift even the most independent entrepreneur if he embraces it. This would be a partner who gives you your space, helps you be your best via encouragement and helps you grow as a person. An even better partner for an entrepreneur would be one who helps with the business in some way, shape or form as well, but now we’re just being greedy.

If you can’t find someone to date like that and are serious about your dreams, it may be better to stay single until you’ve laid a stable groundwork for the rest of your life.

You’ve heard what we thought, now we want to hear what you think. Comment below your belief on if entrepreneurs can be successful even if in a relationship!


The Owner of Proprietor Lifestyle, Steven is an entrepreneur from New York. He's in an abusive relationship with the New York Knicks and is always looking to connect with other like-minded millennials.

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