15 Things You Should Know Before Dating an Entrepreneur

Dating an entrepreneur can be either the most exhilarating thing in your life or it can drive you absolutely insane if you don’t know how entrepreneurs are wired.

In this episode I address the concerns of the following two types of people:

#1: First, this is for entrepreneurs.

An entrepreneur messaged me and asked if I knew of any resources that explain how entrepreneurs are wired. The purpose of this video is to have something your significant other can watch so they can better understand you.

#2: Second, this is for those who are dating entrepreneurs.

If up to this point you’ve only dated people in traditional 9 to 5 jobs, you may be at a loss when it comes to the mindset and habits of your new love. Perhaps you wonder if they even have mental problems! If you’re experiencing that kind of confusion, this video will give you some clarity about why they’re wired the way they are.

15 Things You Should Know Before Dating an Entrepreneur

#1: Entrepreneurs are Very, Very Weird

Let’s face it; entrepreneurs have strange personalities. You can talk to them one moment and they’ll be amazingly happy. An hour later, in spite of the fact that nothing has happened, they’re an emotional wreck and break out into tears. The next thing you know, they’re ticked off, and you’re left wondering what happened.

Entrepreneurs are often more sensitive because they take things more literally than everyone else. They think deeply, and feel what happened rather than just processing things intellectually.

You may even feel like you’re dating three different people at the same time, due to the different personalities. This doesn’t mean that they’re bipolar, but reading books like The Hypomanic Edge and A First-Rate Madness will help you understand how entrepreneurs are wired.

The main thing to be aware of is that something can happen at any time that causes the person you’re dating to shift their thinking.

Now keep this in mind; this tendency may be more exaggerated when someone is in their early twenties, and they’ll likely settle down by the time they’re in their thirties. As your significant other matures, you’ll find they learn how to better control their emotions.

#2: You’ll Either Make it or Bust

When dating entrepreneurs, it’s either bust or all in, rarely something in the middle. I dated several girls that from a logical perspective, probably made the best decision to not date me, because I was absolutely broke. I didn’t have money to pay for gas, movies . . . nothing. On Friday night’s we had to stay home because I couldn’t afford to go to a movie, so instead we went to Blockbuster and rented a movie or watched the same movie 50 times, over and over again. Because of this, I had to sell them on why they should spend more time with me.

The important thing to understand when dating an entrepreneur is that there is a certain level of delayed gratification. Instead of seeing the potential, we often judge people on where they are today rather than on where they’re headed. If someone is broke today, you may think they’ll be broke forever, but that’s not the case.

There’s a three to five-year period where there’s a lot of pain financially, until all of a sudden victory starts showing up. If you can get through the challenging phase, the entrepreneur you date will have an indescribable level of loyalty to you because of the role you played in their success. They’ll appreciate the fact that you had their back when they had nothing.

#3: They Need Solitude at Times

Sometimes entrepreneurs need solitude. And I’m not talking about prayer or meditation in the morning. Sometimes they just want to be away from everyone for a day, or a few hours. Their mind is constantly going and they’re always processing information and adjusting to changes, so sometimes they just need a break.

When they go off alone, you may wonder if they’re seeing someone. No – they just need some time alone so they can regain their sanity.

Some entrepreneurs may sleep 10 or 12 hours on a Sunday because they didn’t get much sleep the rest of the week, and they use Sunday to refuel. Or, they may want to go to the gym or do yoga or go to a quiet place. In those times they may not want to talk to anybody.

If you’re a jealous or insecure person you may be offended, or really struggle with this. It’s important to know that it has nothing to do with you; they just need to some alone time.

#4: They Don’t Live by a 9 to 5 Schedule

If you’re accustomed to dating a 9 to 5-er, you’re not going to get that with an entrepreneur. If he or she stops working at 5:00 pm, they’re not an entrepreneur; they’re someone who just says they’re an entrepreneur, but they’re not.  Entrepreneurs go, go, go, non-stop. So don’t expect them to come home at 5:00 pm and watch some shows with you.

However, there are various levels of entrepreneurs. Some may get to the place where their business is making 200K a year and they’re content with that. If that’s their goal, they may be able to come home by 5:00 pm. That’s totally fine.

But for the true entrepreneur, the outcome has nothing to do with dollar signs. The outcome they’re looking for is that they absolutely must create for the rest of their lives. It doesn’t mean they don’t love you; they’re just always on the hunt. That’s how they’re wired.

So what’s the solution? Entrepreneurs like schedules. Add your dates to a calendar and then give them reminders. If they have an assistant, stay very close to the assistant and have the assistant also remind them.

#5: They Usually Never Clock Out

Perhaps you’ve experienced something like this. You’re out to dinner in a restaurant and all of a sudden, your significant other becomes distracted. The wheels in his mind are turning, but he’s definitely not thinking about you. In this state of deep thought, he starts writing down ideas. He may even be so focused on what he’s doing that he doesn’t even respond to you when you try to get his attention.

You may feel very frustrated when he doesn’t hear or respond to you in the way that you’d like. In your mind, he’s neglecting you, but in his mind, he’s sitting right there with you.

It’s possible that something he saw in the restaurant triggered an idea for something to do in his own business or to discuss with one of his executives, and in split second, he’s completely “gone.”

When this happens, it’s easy to take it as, “He never pays any attention to me” but that’s not true. Know that it’s just how he’s wired, and it has nothing to do with you.

Or picture this scenario. On a Sunday afternoon you may be sitting there watching a movie, and your girlfriend all of a sudden thinks of something she needs to work on so gets up and is gone for 30 minutes. Or she may wake up at 2:00 a.m. and get out of bed and type away at something for an hour.

These are signs of true entrepreneurs. And these things happen because their minds never turn off. If you try to change them, you’ll cut the life right out of them, which of course you don’t want to do.

#6: They Don’t Do Well with Ultimatums

Pat, I’m dating this girl and I’m at a point where I feel like I need to settle down. But she told me that it’s either me or the business, because she can’t stand the fact that I’m working the way that I am. What should I do?

When my friend asked me this question, I couldn’t tell him what to do, so instead asked him how he’s wired. He came to the conclusion that he couldn’t accept the terms of the ultimatum because it meant being asked to change who he is.

When someone says, “It’s either me or the business,” — here’s how an entrepreneur sees that: It’s like saying, “It’s either your arm or me. What’s more important?” Even if you really love someone, you’re not going to cut your arm off for them, right? In the same way, it’s not realistic for you to expect someone to be a whole different person, just to be with you.

Now this doesn’t mean that they won’t change or improve over time, but you can’t ask them to stop being who they are.

The last thing you want is to date someone who ends up being filled with resentment 10 or 20 years later because you asked them to be someone different than who they truly are. Putting someone in that position is like a dating or marrying a ticking time bomb who can end up becoming your biggest enemy because you tried to change them.

#7: They Will Miss Events

In the book Total Recall,  Arnold Schwarzenegger tells the story of what happened when he came to America to compete in Mr. Olympia. His father passed away right before the event. His mother was very disappointed that he wasn’t going back to Austria for the funeral.

Arnold knew that if his father was alive, he’d tell him to go after his dreams, but his family didn’t understand that.

Some people may feel that Arnold was cold-hearted, and that he shouldn’t be used as an good example. If you’re thinking that, you need remember all that he’s overcome and accomplished. He maxed out his life in business, health, entertainment, and politics.

Here’s a solution to this challenge: Ask your significant other, “What are the events you’re not willing to compromise on me being there?” It could be things such as big holidays such as Christmas and Thanksgiving. The key is to determine those ahead of time and communicate about them, and come to an understanding about the things that really matter. Just don’t expect them to make every party, or to show up on time for every event.

#8: They Are Frequent Travelers

Entrepreneurs will be away from home a lot. You may wonder why they’re always on the road, but they need to meet with vendors, clients, business partners, investors and so on.

You need to figure out a way to entertain yourself and be OK with a lot of alone time.

This is especially true if they’re building a national business.

#9: They will Talk to Strangers Quite Regularly

This may be very awkward for someone that is dating an entrepreneur for the first time. When you go to a restaurant, they may start a conversation with a perfect stranger. You may see that as flirting, but they’ll just see it as talking.

Entrepreneurs are curious people. They want to learn from everyone. Everything to them is an opportunity. This isn’t true for 100% of entrepreneurs, but entrepreneurs are generally curious people and want to talk with a lot of different people.

#10: They Ask a Lot of Questions

You know how it is when you have a three or four-year-old kid that just won’t stop asking questions? That’s what it’s like to date an entrepreneur. Entrepreneurs are always curious and asking questions.

#11: They Usually Attract the Spotlight

Many, many times, the fact that the entrepreneur gets all the attention causes problems.

It’s true that the entrepreneur needs to make an effort to shine the spotlight on his significant other on a regular basis, because that person plays a very important role in the success of an entrepreneur, but it’s natural for a lot of attention to be on the entrepreneur.

#12: Your Friends & Family Will Either Love them Or Hate Them

14% of American workers are entrepreneurs. That means that 86% of the people don’t know what it’s like to be married to an entrepreneur. Because of that, the advice that your friends or family may give you comes from a place of someone who has married a 9 to 5-er. So their feedback is from that perspective, and they can’t really relate. They may measure the entrepreneur based on what they know from having family members who worked from 9 to 5. It’s not a fair assessment.

Don’t take advice from someone that’s dating or married to a 9 to 5-er when it comes to your relationship with an entrepreneur. Instead, be sure to get counsel from people who have experience in the area where you are seeking counsel.

#13: They Have Strong Opinions

Entrepreneurs may have strong opinions about everything ranging from politics, finance, health and many other things. The reason they have strong opinions is that no one gives their all to something unless there is a strong conviction to put their time and energy into it.
Not every entrepreneur has strong opinions, but many entrepreneurs do. You don’t necessarily have to agree with all of their opinions, but it’s important to be prepared for the fact that they do indeed have strong opinions.

#14: They Despise Lazy People

Entrepreneurs don’t just dislike lazy people; they despise them. If they date someone that is lazy at heart, an entrepreneur can usually read through the BS, and it will be a very short-lived relationship.

They also want the person they’re dating or married to be in the hunt for something, because they want to learn from you as well.

#15: They Get Bored Very Quickly

Entrepreneurs get bored very easily. They are constantly learning and they want to be with someone that is also hungry, growing, and learning.

Your Turn

I’d love to hear comments from you. Whether you’re an entrepreneur or someone dating an entrepreneur, what would you add to this list? Or if you have questions, be sure to leave them below.

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