A woman dating an entrepreneur, eating breakfast and having a good time whilst at a cafe

Last week I covered how much you should be spending on dating. One of my business partners saw the article and asked if I could do an article about what you should know when you are dating an entrepreneur. So, what are the things that people should know when dating an entrepreneur?

18. They are the center of attention all the time

When you are dating an entrepreneur, it is quite often that they will get all the attention. This can be from the media, friends, family or all three!

Entrepreneurs work incredibly hard in order for their work to get recognized, so when it recognized by the media, they are quite proud of it. But they never forget to (at least) try to redirect the spotlight to their significant other.

The same can be said for family occasions. Your mom, or your brother, or another relative will always ask how the business is going at the moment. This can be quite frustrating, as you too have a career of your own, which often gets neglected in favor of your significant other’s.

Whilst they will try to deflect some of the attention to you, as you play an important role in your significant other’s success. It is perfectly normal for the attention to go straight to the entrepreneur.

17. Entrepreneurs are really, really, really strange

Entrepreneurs can at times (heck, most of the time) come across as quite strange people. Entrepreneurs tend to live quite strangely- one moment they can be the happiest person alive. The next, they are an inferno, cursing the high heavens. And the next, they are crying and weeping as though someone has died (even when no one has died).

Despite the fact, literally nothing has happened to them.

They’re not exactly bipolar, but they’re not exactly ‘normal’ people.

As a general rule, entrepreneurs take everything, way more literally than everyone else does.

You will need to comfort them, no matter what they are feeling.

16. Mind what you say when you start dating an entrepreneur

Entrepreneurs generally have firm beliefs, and they’ll generally expect you to respect (or even share!) those opinions. They are also sizing you up, as they would an investor, business associate, or even if their mom will approve!

With entrepreneurs, they’re always looking for the analytical aspect of you. They need to know how you’re wired, to see if you’ll put up with them.

By this, I don’t mean be completely silent on the first date. But, think about what you are saying before you do.

15. They’re always away from home

Entrepreneurs live for their business- their business is them, and they are their business.

They will go wherever their business takes them. End of story.

When you initially start dating them, you’ll probably be a bit upset, and wonder if they’re cheating on you. They are not.

If their business has a problem with a vendor in another state, or on the other side of the country, that they can’t resolve by phone, they will go to see that vendor in person. The same can be said for business partners, clients and investors!

Most of these tend to come last minute, which makes it hard for them to invite you to come along with them. Normally, you’ll have your own job and career to worry about.

You will need to be OK with the notion of being on your own.

14. They rarely stick to a 9 to 5 schedule

For most people, they get up, go to work at 9, and finish at 5, day done. They come home, eat dinner, watch some TV, and go to bed. Rinse and repeat.

Entrepreneurs rarely come home at 5pm.

Yes, occasionally, they might, but as a general rule, you could see them working until 10pm!

Entrepreneurs don’t care about the money. It’s all about creating. Creating a legacy. And never slowing down.

This doesn’t mean that they don’t love you. They almost certainly do love you. It’s just that they are always on the hunt, it’s simply how they are wired.

13. They never really clock out

Just because they’ve come home, or they’re on a date with you, it doesn’t mean they’ve stopped. On the contrary, they have merely slowed from a run to a sprint.

You may be sat in a restaurant ordering a meal, on a date with an entrepreneur. All of a sudden, they reach into their pocket, and pull out a pen and paper, and start writing down something- usually something you are unable to work out the meaning of.

You may get angry, and believe they are writing ill of you. They are not. A pen and paper is an entrepreneur’s best friend. Normally, you’ve just said something that has reminded them, that they need to talk with an executive about something.

Or even better- you’ve just given them a great business idea, and you didn’t even know it!

12. They will never, ever slow down

For most people, the sweet smell of retirement is the main reason they get up in a morning- not for entrepreneurs. Most entrepreneurs don’t work because they have to, they work because they want to. As Warren Buffett once said:

I will die with my boots on.

Most entrepreneurs have the same mindset.

If you are looking for a guy/girl who you can retire and settle down with once you’re 65, you are mistaken. When dating an entrepreneur, know that they will still be working long past their 90th birthday in some cases.

11. They will miss events

This is a key thing to keep in mind when you are dating an entrepreneur. They will miss special occasions: birthdays, anniversaries etc.

This isn’t because they don’t love you, it’s just that their business is the #1 priority.

If they had a choice, they’d always choose to be with you.

The best thing for you do when you are dating an entrepreneur, is to ask them what the most important holidays are. The flat out ask them if they’d be willing to miss them. They usually won’t break this.

10. Your friends and family will either love them, or hate them to pieces

Only 14% of workers in the US are entrepreneurs. This means that 86% of workers aren’t entrepreneurs. It’s highly likely that most of your friends and family have married regular 9 to 5ers.

They won’t get why you put up with your significant other all the time.

When your significant other misses a birthday party for your kid, or some other celebration, you’ll get told that they aren’t the person for you.

This is because they have only ever been married to a 9 to 5er. They will equate the entrepreneur to their own significant other, or other members of their family.

When it comes to comparing entrepreneurs and 9 to 5ers, it is hardly a fair assessment.

9. They really despise lazy people

Entrepreneurs don’t merely dislike lazy people. They wholeheartedly despise them.

For entrepreneurs, lazy people embody everything about society that they hate. Entrepreneurs always have to be proactive, rarely reactive.

If you are a lazy person at heart, and you are dating an entrepreneur, they will see through the mask you put on. And your relationship will be extremely short-lasting.

With entrepreneurs, they’re always looking to get something from you as well as love. Usually, they’re looking to learn from you, something that they find lazy people are unable to do most of the time.

8. They will test you

This may only apply to a select few entrepreneurs. But when you are dating an entrepreneur, they will do tests on you, to see if you are capable of putting up with them.

They will try to see if they can trust you. This doesn’t mean that they didn’t trust you before, but they need to be certain.

Entrepreneurs want to make sure that you are the real deal when they are dating you.

If you fail, it’s game over. If you pass, it’s generally happy sailing from there.

7. You are their everything, even if it doesn’t seem like it

From what we’ve said about dating an entrepreneur, you can gather that their whole life revolves around their business. You may feel like you are playing second-fiddle to your significant other’s business. Trust me, you are not.

It may not seem like it, but you are the center of their universe. This is especially true if they were the one to ask you out on the first date.

They’d do anything for you, literally anything, to make you happy. Even if they have forgotten it’s your anniversary for the third year running.

6. They ask so many questions

Have you ever seen a 5 year old, who just does not stop asking questions? That’s what dating an entrepreneur is like.

It’s likely that when you are dating an entrepreneur, they have so many questions for you. Don’t be put off, they do it to basically everyone they meet.

Rich people never stop learning and trying to improve themselves. Entrepreneurs and rich people are very much the same. They know that they can never stop learning, else they’ll lose their edge.

5. They will start having a conversation with a completely random stranger

Whilst this is not always the case with entrepreneurs, it is quite common. This may often be quite strange from the perspective of someone who’s dating an entrepreneur for the first time.

Entrepreneurs might be in the weirdest of places, and just hit up a conversation with a complete stranger, and after 5 minutes, it would look like they’d been friends for years.

This can be quite frustrating for those who are dating an entrepreneur. It can sometimes appear as flirtatious, even when, to them, it is mere conversation.

This is because entrepreneurs can never stop learning. So chatting with a complete stranger can often provide the best market research, that an entrepreneur’s inner friendship circle often can’t provide.

4. They often don’t have large friendship circles

Most people have three layers/levels of friends: acquaintances, friends, and close friends. For entrepreneurs, they have acquaintances and close friends, sometimes only close friends.

This is because they only associate with people like themselves.

As it was once said:

You are the sum of the five people you spend the most time with

Usually, an entrepreneur will only associate with other business owners, entrepreneurs and executives. This is because they have similar problems and interests, and usually have encountered the same issues before.

If you are dating an entrepreneur, and expect that they will have an army of friends by their side, you are wrong. They may only have a few people in their inner friendship circle.

3. They don’t do well with ultimatums

So, you’ve been dating an entrepreneur for a while now, and you’re sick an tired of their sole devotion to their business. You are sick and tired of waiting for them. And the perceived in-affection they seem to have for you.

So you decide to give them a choice, you, or the business.

This is generally a bad move. Generally, entrepreneurs won’t accept the terms of the ultimatum, as it would force them to change everything about them. And potentially give up something they’ve been working on for years, potentially since childhood.

If you are dating an entrepreneur, and you give them this ultimatum, it like you’re saying to them “It’s your arm or me?”

They might love you, but they aren’t willing to cut their arm off for you.

It’s the same mentality as, it’s unrealistic for you to expect someone to be a whole different person, just to be with you.

2. They get bored extremely easy

If you are dating an entrepreneur, always keep them doing something, or learning something new. If not, it’s unlikely that they will stay with you for very long.

We’ve already established that entrepreneurs want to learn, and will never stop learning. They want to be with someone who embodies everything that they love.

They want to be with someone who is hungry to learn and grow as a person. But this hunger has to be a burning desire to learn, not something that is half-attempted.

If it is, they’ll get bored, and the relationship will be short-lived.

1. You are their number one fan, and they are yours

This seems quite straight-forward, but it is one of the most important things to remember when you are dating an entrepreneur.

If you can support them when they are at their lowest, and be their biggest cheerleader when something amazing happens, your relationship will be long lived and successful.

If you are dating an entrepreneur, they understand that you are there for them, whenever they are down. They too will be your best friend in your time of need, but also your biggest fan when you are riding high.

Are you dating an entrepreneur? Are you considering dating an entrepreneur? Is there anything that you would’ve added to this list on what you need to know when dating an entrepreneur? Tell me in the comments!


Thibault Kuten

Thibault Kuten is dedicated to helping you become financially free. He is an entrepreneur, businessman and investor, having done so for more than 15 years.