How to Date an Entrepreneur

culled from:wikihow.com

If you’ve ever dated, married or been interested in an entrepreneur, you know that they think, act and relate differently than the average person.^[1] Sometimes that can be a challenge for the non-entrepreneur — especially one who doesn’t realize that they aren’t crazy, they just need to think...sideways...to get through to their sweetie.

Given that, it might be useful to know how to spot the TRULY self-employed (not the one who just says they do xyz but have no numbers to back it up), how to figure out if you are suited to date one, how to communicate with one and how to survive the ups and downs that happen in EVERY entrepreneur’s life.

Steps

1

Know if you're dating an entrepreneur. This is based on the typical entrepreneur. At times a newly successful business owner might shoot the curve by going bling or an old schooler may decide to take a break. But if you look carefully, these attitudes will still be there.

• Careful about money. If you are planning to date a business owner, be prepared to be picked up in a practical and non-flashy car, go to dinner at places with good food but not over the top, eat in as much as you eat out (if not more) and live in a reasonably sized house in a good part of town (likely with fixer-upper projects needing completion). Any successful business owner keeps an eye on the bottom line and always calculates the cost analysis. Don’t be surprised if you get in a fight and s/he flings a number out at you about how much you have cost them (in terms of money earning time or actual $$).
  
• Careful about time. Entrepreneurs tend to get up early and stay up late. You’ll likely see a comfy couch in their office — short naps are the backbone of most of the successfully self-employed. They squeeze in emails, calls and deals in between bites of dinner and trips to the bathroom. If they see it as a “waste of time,” they’ll be grumpy if not allowed to cut free and move onto something deemed productive. It can become a balance issue, and likely ends most relationships before they ever get off the ground. But if you can talk to your entrepreneur and strike a bargain, you’ll come out a winner on all fronts. (See the section on communication below.)
  
• Competitive risk takers. Your honey will seem (to you) to be blase about risk. They aren’t. The risks are always calculated and analyzed (for the successful entrepreneur) but for someone who isn’t used to free falling, it can be scary. They are also extremely competitive. Family game time can get a bit hairy and most will use the rare free time competing in their favorite venue, be it sports, gaming, gambling, whatever.
  
• Loners. You might have a hard time getting your honey out of the house once they get home for time to relax. Some do a good job putting on a social face, especially if it means networking, but know that your entrepreneur will not be someone who follows the pack. If the rest of the world thinks one way, your honey will likely think exactly the opposite or between the lines or even off into the future to see some eventual possibility most could never imagine.
  
• Business minded to the point of scanning every environment you are in for business ideas or drifting off after you tell them something random and swimming back into the conversation after turning your random comment into a business application. They are also problem solvers in the extreme and will simply not understand you wanting to talk through something without coming to a solution. If you need them to stop problem solving for you, be direct and tell them so. It may take some getting used to, but when they begin to see that you solve your own problems in your own time frame, they will generally lay off and let you do your own thing.
  
• Tend to be honest and direct. Many are people that are trusted with handshake deals. If your entrepreneur is at all community minded, you’ll find them attracting and collecting people a lot like them.
  

1. 
   2
   Become comfortable with risk. If you are risk-adverse, you’re going to either have to get over it or learn how to support someone who lives and breathes risk. After all, it's part of their genius and if an entrepreneur was afraid to take risks, they wouldn’t be able to start and grow a successful business. Being more Zen about the ups and downs of life will help you more than just about anything in living with an entrepreneur.
2. 
   3
   Be independent and ready to fill your own time. If you need to be the center of your honey’s attention, you may really struggle with what will seem to you to be an inordinate amount of time spent at the computer/office/in meetings/on the phone.
   • How to Stop Being Needy
   • How to Avoid Being an Obsessive Girlfriend
3. 
   4
   Understand the value of money and don't be a big spender. You will be the apple of an entrepreneur’s eye! By not expecting them to spend money on the “frivolous,” you will be head and shoulders above the pack in their estimation.
4. 
   5
   Be optimistic, positive and generally not prone to worry. Bingo. You’re the entrepreneur’s version of a rock star.
5. 
   6
   Be flexible with time, expectations and plans. You guessed it; most entrepreneurs don’t know the meaning of “weekend,” “evening,” or “vacation.” Here are some examples:
   • You might be shocked to find that your entrepreneurial love interest expects to continue working - via phone - even on their honeymoon and the entrepreneur will be surprised if you get upset about it.
     
   • A vacation with an entrepreneur might involve negotiating phone and laptop time.
     
   • Many entrepreneurs will ask a date if they are ok with them taking care of “this little bit of business” in between dinner and later plans.
     
6. 
   7
   The dates that entrepreneurs adore are the ones who either offer to help, or are relieved to take care of some of their own work while they're busy.
7. 
   8
   Know when they are "on the clock". You can recognize this state of being by the one word answers, slightly clipped replies, distracted mentality and maybe a little irritability if you interrupt a stream of thought or creativity. When they are "off the clock" on the other hand, this is likely the person you fell for. Many entrepreneurs have a great sense of humor, intellect and creativity. Some also have natural charisma and charm when they have the time to just relax with loved ones. When an entrepreneur sets his or her eyes on someone they want to get to know better, you become their latest goal and all that talent, charm, sales-ability and intellect that usually goes toward getting more business will come your way.
8. 9
   Be direct when he or she is "on the clock". Be direct, practical, non-fluffy and ask for minimal input on issues outside of the practical or easily taken care of situations. By thinking of the bottom line and then approaching all communication at that level, you can bypass some of the irritation via interruption.
   • For example, instead of, “You remember that guy we talked to at the party a few weeks ago — the friend of yours who owns a Mustang. You know, the party where you had that one wine you really enjoyed? Okay, so what was the name of the plumber that he mentioned really liking? If you have the time today, it would be great if you could get that information and contact the plumber about fixing the toilet for us. Can you do that? I’ll be home most of the afternoons this week and it would be easy for me to wait for him here.”
     
   • Try something more along the lines of “Will you please schedule that plumber that your friend Joe recommended to come fix the toilet between 2-5 any day this week?”
     
9. 
   10
   If you are having trouble getting through to your sweetie that something is really important to you, try to give them a cost/benefit analysis of the situation. It may seem harsh to you, but to your entrepreneur, it will seem natural and best of all — will make sense to them!
   • Another example: Instead of “I can’t believe you are on that damn CrackBerry all the time! You don’t love me! If you did you wouldn’t spend so much time working when we are supposed to be out! You don’t even talk to me. If you don’t get it together and treat me with at least as much attention as one of your stupid business deals, I’m leaving!!”
     
   • Try this instead: “I’ve noticed a communication and time breakdown in how we are investing in our relationship and wanted to know if you’ve noticed the same thing. (Insert a few concrete examples if your honey likes backup information) Since I care about you very much, I want to make sure we are both meeting each other's needs so our relationship can continue to grow and expand. I need _______ in order to continue growing this relationship and am wondering if you are able to meet that need or would you prefer to be with someone who doesn’t need you to meet that need?” It's a simple and direct problem analysis. One that s/he could easily hear in a boardroom or client meeting.
     
   • For more guidance, see How to Practice Nonviolent Communication.
10. 
    11
    Ask for balance and expect it. Realistically, this will be the largest hurdle for most newbie entrepreneurs. The old schoolers understand that you need balance or you will burn out, but the new ones think that they can just keep going at that rate and life as they want it will be waiting for them when they are done. If you love this person or are trying to make something work with them, approach it like the above outlined business proposal and explain what you need in terms of ROI (or return on interest/investment).
11. 
    12
    Don't forget that this person cares about you. Yes, many entrepreneurs are lost in their business, kind of like a new mom with her baby, but that doesn’t mean they don’t care about you or have lost the qualities that first attracted you. Remember that, for them, time is probably their largest sacrifice. If they are giving that to you, it should tell you quite a bit about where you are on the priority scale.