How To Date an Entrepreneur And Pitfalls to Avoid


If you’ve ever dated, married or been interested in an entrepreneur, you know that they think, act and relate differently than the average Joe (or Joette.) 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 partner.

Having been raised by an entrepreneur, having been an entrepreneur, having dated entrepreneurs and looking at what’s happening in our economy… I thought it might be helpful to write a post about 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.

How to Spot Em (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)

  1. Careful about money. Yup, 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 $$).
  2. 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 section on communication)
  3. Competitive risk takers. Your date/spouse 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.
  4. Loners. Yup. You might have a hard time getting your entrepreneur 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 partner 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.
  5. Business minded to the point of scanning every environment for business ideas. They are also problem solvers in the extreme and will simply not understand you wanting to talk thru 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.
  6. 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.
  7. If you are trying to figure out if s/he’s the real deal ask yourself one question… do they have a “side job” that contributes a good part of their income? Most of my entrepreneur friends will tell you that no true business owner/starter has the time or inclination for splitting their heart between two jobs. Their business is their baby and everything goes into that. For those who don’t have handy start-up funds, they may squeeze in a side gig or two to raise the dough needed, but will likely never mention it or identify themselves by their side job.
Ok, so you now know how to profile a successful entrepreneur, are you well suited to date one?
  1. Are you risk adverse? Well, you’re going to either have to get over it or learn how to support someone who lives and breathes risk. After all, its part of their genius and if an entrepreneur was afraid to take risk, 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. Are you independent and used to filling your own time for the most part? Perfect. If you need to be the center of your mate’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.
  3. Do you tend to understand the value of money and NOT be a big spender? You would 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. Are you optimistic, positive and generally not prone to worry? Bingo. You’re the entrepreneur’s version of a rock star.
  5. Are you flexible with time, expectations and plans? You guessed it… most entrepreneurs don’t know the meaning of “weekend,” “evening,” or “vacation.” My mom was shocked to find that my dad expected to continue working – via phone – even on their honeymoon. My dad was surprised when she got upset about it. My most recent vacay was with a entrepreneur and we had to negotiate phone and laptop time. When I owned my own business, I was well known for asking a date if they were ok with me taking care of “this little bit of business” in between dinner and later plans since my clients required me to be on the clock around 8:30-9:30pm. Some dates were cool with it, some were not. The ones I adored were the ones who either offered to help me or were relieved to take care of some of their own work while I was busy.
Down to the brass tacks: How to communicate with the “all business” guy/girl vs. “off the clock” guy/girl.

On the Clock or all business: 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. 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 week ago — the friend of yours who owns a Mustang. You know, the party where you had that one wine you really enjoyed? Ok, 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?”

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 partner likes backup information) Since I care about you very much, I want to make sure we are both meeting each others 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?”

Its a simple and direct problem analysis. One that s/he could easily hear in a boardroom or client meeting.

Off the Clock: 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.


  1. You HAVE to communicate! Even if they don’t seem to have time (they never will), ask them to schedule you in to discuss the important things.
  2. 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).
  3. Expecting them to have a “normal” 9-5 schedule. It just won’t happen. If you can’t accept that, then move along. Also, a real entrepreneurial type will likely never retire. If they say they will, don’t believe it or ask them what they mean by “retire.”
  4. Forgetting 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.