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 of 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)
- 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 $$).
- 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)
- 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.
- 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.
- 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.
- 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.
- 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?
- 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 en entrepreneur.
- 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.
- 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.
- Are you optimistic, positive and generally not prone to worry? Bingo. You’re the entrepreneur’s version of a rock star.
- 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.
The PITFALLS!
- 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.
- 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).
- 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.”
- 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.
49 Comments
January 1, 2009 at 7:25 am
Great advice in general (saw this from news.ycombinator.com) with the exception of the “side job” thing.
It’s pretty common, especially in the early stages, for an entrepreneur to have a “day job” and a “side job”, with the side job being the actually entrepreneurial venture.
Sometimes it’s not as visible — a consulting company (short term cashflow) which also develops products (long term strategy).
There are a lot of disadvantages to this kind of thing (split focus, and especially sacrificing the long-term to deal with short term), but I’ve found it’s better than the “try to raise money, then do a company” route. The best way is of course to somehow scrape by working 120h/week on the “real, long-term” thing AND have revenue from it as quickly as possible, but that’s not always possible.
The “efficient communications” thing probably applies to all “geeks”, but is especially important for entrepreneurial people.
January 1, 2009 at 10:39 am
Some point are a bit extreme (like the cost/benefit analysis for improving the relationship) but overall this is a pretty good description of the issues of which to be aware.
One thing to keep in mind is that if someone is so focused on work that they consistently require ROI explanations of everyday situations, then it’s likely they’re not in a healthy frame of mind to be in a relationship.
January 1, 2009 at 10:45 am
Eric,
I know! I was trying to write this and think, how do I explain this most succinctly and when I really started thinking about it, I realized that a lot of entrepreneurs really aren’t in the best place to be in a relationship but many of us are, even when in the trenches of start-up land. And some are already married and starting this whole self-employed thing for the first time. I think it takes some practice to learn how to balance it and in the beginning… the dice can land on ROI more often than not in an effort to stay afloat on all fronts. Obviously, healthy and balanced is ideal and I’m all for seeking that place. But I’m also all about how to make it work even when not perfectly healthy or balanced or put together since all of us have moments/days/months/years of that in our lives until we learn how to embrace what balance means in this new stage of life/experience.
Thanks for your comment and I’d love to know more about what you think about how to effectively communicate with someone in a entrepreneurial type situation… any tips would be appreciated for the frustrated spouses and significant others out there!
Kelli
January 1, 2009 at 12:03 pm
Patricia and Ryan, I agree with you for the beginning stages, I should have clarified that its when the business starts taking off the side jobs disappear because of the general time suck and lack of desire to split your heart and mind in two directions. I put this one in there as well though as a warning sign because a LOT of people claim to be self-employed and are more like under-employed and so many men and women now think “oh, self-employed or contractor means that person doesn’t really have a job” which does the rest of the hard working entrepreneurs such a disservice. I was raised in the school of either bootstrap it or have the capital handy because if you borrow, you are really working for someone else… it’s probably colored the way I look at start-up stages as well.
January 1, 2009 at 11:46 am
Great article, though I don’t agree having a second job to supplement your income as an entrepreneur is a sign of anything. A relative in my family did so, and the company he founded during that time is now a large, highly successful manufacturing facility that has been in business for more than twenty years. I did the same with my first start-up, and it enabled me to fund it myself. I sold it last year.
January 1, 2009 at 2:01 pm
The part of communicating with an entrepreneur who is on the clock is spot-on. Funny and accurate write-up!
January 2, 2009 at 2:57 am
Will,
I’ll admit to learning the hard way on this point. I used to fluff and soften and finally realized that I was wasting everyone’s time. My dad and dates since then have been in great relief that I finally learned how to speak their language. The funny thing is that I never realized I was the same way until a room mate got mad at me for not listening to her (admittedly long winded) stories when I came home after a really long day of work. I tried to explain to her that more talk was the last thing on my mind but she was just offended. NOW, I know why!
January 1, 2009 at 4:25 pm
Wow! Great conversation started and thanks! I’m traveling all day, but will come back on tomorrow and reply to your comments… Thanks everyone
January 1, 2009 at 5:38 pm
Thank you for writing this.
January 2, 2009 at 12:24 am
This ought 2 b called ‘another way to trap a man’ Jeez. This is all about the WALLET. How crass
January 2, 2009 at 2:49 am
For those of you who passed this along or said thank you… thank you for commenting and I hope it helps someone understand those of us business starters a little bit better. Of course, we aren’t all the same, but some things travel across for most people. *grin*
Blackbolt1 — Hummm… either someone didn’t read the post or I wasn’t clear enuf about NOT living life large and NOT being a big spender. But in case I wasn’t as clear as I needed to be… For all the Gold Diggers out there — women AND men… dating/marrying an entrepreneur is NOT the way to strike gold. There is a LOT of risk attached to what we do and for every one business that succeeds for the average entrepreneur — 7 (on average) fail. Added to that, for the most part, the self-employed of the world are not big spenders since every extra penny gets funneled back into the business or to pay all those pesky taxes. This isn’t to say that entrepreneurs are cheap or all about the money — we are just all about the business and in the beginning stages, that takes money to keep it going.
January 2, 2009 at 2:29 am
Amazing. I just sent this to my girlfriend.
January 2, 2009 at 2:41 am
John — I wrote it in hopes that the guys and gals out there dating the entrepreneurial types would find some hints on how to make it less stressful when those of us who are self-employed get in the trenches and forget to come out and breathe at times.
Glad you liked it and I hope she does as well.
January 2, 2009 at 4:12 am
My girlfriend just forwarded this to me….she finally knows that she is not alone and there are other inflicted souls like her who are in a relationship with an entrepreneur.
January 2, 2009 at 4:15 am
LOL
January 2, 2009 at 11:57 am
I find that many people think they can handle the free fall and non security that comes with the territory, but once they are in the den,(watch out). Safety and long term security is the words of the day for most. You touch a lot of hot buttons, keep it up.
January 2, 2009 at 12:05 pm
Alactract — Boy do I hear you. I’ve seen three of my friends go into marriages with people who *thought* they were ok with the risk taking and lack of week to week “paycheck.” I would say its the number one reason they argue and one couple is splitting after less than a year together. Its not easy for anyone, but I think it’s something most entrep. learn to not only live with, but see as fruits of their labor when the big payoffs start to make up for the lean years.
Trickyguy — I agree about being a priority, in fact, I think it’s vital to being able to stick it out with someone in the business trenches. I guess I, personally, look at it more as — I know that when he does have time, he wants to spend it with me and thinks of me even when things get really busy. But most start-ups simply eat up time for at least the first 2 years and I think its something that you have to be ok with going into it all. That comment is more to let the girls/guys who are used to the 9-5 demands and being the absolute every waking thought person that dating en entrep. may not be the best plan for them.
Ricardo — let me know if there are any other topics that would tickle your fancy and thanks for the kudos!
January 2, 2009 at 12:01 pm
Thanks for a well-written and interesting post. I did have a comment on one part in particular.
One can be an independent person, yet still want to a real priority (you called it “center of attention”) to the other person.
That’s neither wrong nor mutually exclusive with dating an entrepreneur. It’s part of the respect we should show someone we care about.
Businesspeople often find that their relationships are strained or even fail when they lose a healthy work-life balance.
Sure, sometimes when a critical project is due, crunch time dictates long nights, take out food, and little to no time for personal relationships.
But, what keeps those folks going is that, over the long haul, they find ways to make each other priorities in their lives.
January 2, 2009 at 12:02 pm
lovely and useful I could married your-blog so from now on is on my favorit list!
very good job kelli.
January 2, 2009 at 12:10 pm
Perfect and spot on. The second job reference is brilliant. Ignore the comments, you are totally right. Those with a plan B (second job) aren’t true entrepreneurs. Your dad raised you well. Keep up the great work!
January 2, 2009 at 12:11 pm
I got this link frm my girlfrnd……….n she is saying me to learn something …….
January 2, 2009 at 12:24 pm
Excellent post. I can relate to this first hand. Unfortunately this insight came a little to late as my relationship ended last summer. But it was nice to finally understand what really does go through the minds of entrepreneurs
January 2, 2009 at 12:35 pm
Thanks for this article. It is a great summation. However, it seems to overlook the situation where both parties are entrepreneurs, as are my wife and I. It’s the absolute best thing!
January 2, 2009 at 3:52 pm
Renn — thank you… I’ll let my dad know that he’s getting kudos as well. LOL
Lucky — is she the entrepreneur or are you?
Viewsfromthenorth — Thanks for the comment and sorry to hear about your relationship demise. Was it related to the ups and downs of self-employment or just one of those that weren’t meant to work out?
Matt — you are the luckiest of them all. *grin*
January 3, 2009 at 2:36 pm
Thx for the insight (“I’ve noticed a communication and time breakdown…”). It’s *exactly* how I’d like to have a convo about this subject.
If I had found a woman like this, I’d prolly be married. Gonna Tweet it out to my followers.
Dean…
January 6, 2009 at 5:09 pm
So Dean… you’re saying you’re single?
January 3, 2009 at 5:01 pm
Wow, great post! I am married, but always interested in anything pertaining to entrepreneurship…I plan to link to this post on my blog. Thanks!
January 6, 2009 at 5:08 pm
Thanks Davina! I hope the post rolled over to help the spouses too… after all, entrepreneurs don’t tend to change their stripes just b/c they got hitched. (as much as the spouses sometimes wish they would *grin*)
January 15, 2009 at 7:19 am
Interesting, as we list entreprenuers.. or at least we will be , its only been a few days
February 2, 2009 at 7:57 am
a great read… just sent this to my girlfriend
February 2, 2009 at 10:42 pm
I’m an entrepreneur and my friend (also an entrepreneur) just sent this to me.
You literally just spelled out the EXACT reason I can’t keep relationships and the EXACT dream girl I envision all the time.
I rarely leave comments on blogs, but you hit it so PERFECTLY I had to just say – Kudos to you.
I fit everything up there EXCEPT I do spend frivously, a little too much.
February 2, 2009 at 11:10 pm
It can be a challenge to understand the entrepreneurial mindset if you’ve never been there… but I was hoping to shine the light on a few of the more baffling things for the folks dating us. Glad it hit the nail on the head for you guys and good luck…
February 4, 2009 at 11:16 pm
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February 7, 2009 at 2:57 am
Bravo! You hit the nails right in the heads!
February 24, 2009 at 1:55 am
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March 9, 2009 at 6:19 pm
I’m so glad I found your blog just now. This article is fantastic, you have described the entrepreneurial mind very accurately. I tend to have the opposite problem – guys not understanding my lifestyle and mindset as an entrepreneur – so if you could just tell me where to find the like-minded entrepreneur guy that I’m looking for…
March 10, 2009 at 5:20 pm
Jen!
Welcome and thanks for your comment. I HEAR you loud and clear… until I sat down to write this article, I didn’t realize how many of these traits I exhibit when I am in the process of starting a new project or writing and editing or even when I ran my own business. I won’t say its the healthiest all the time (hello workaholics-r-us), but its a good thing to know about yourself.
I tell every entrepreneur I know to REALLY really ask and examine how their significant other handles risk and independence… some people just aren’t cut out to swim in the self employed pool and will drag both people down when they feel like they are out of their depth and drowning in the risk.
As for where to find em… how about we make a pact that whoever finds the land of entrepreneurial hotties — emails the other person ASAP!
March 11, 2009 at 7:39 pm
Your comment really made me laugh! It definitely isn’t a healthy lifestyle but I have given up trying to change the way I am and just get on with life. Can’t please everyone and I love what I do and how I do it.
]
“The land of entrepreneurial hotties” – it’s like the proverbial pot of gold at the end of the rainbow… will definitely give you a shout if I discover it. Will need female support anyway, once I get there! [Maybe this is a question to ask on Twitter: "Single, male, hot entrepreneurs - where do you hang out?" - it's less than 140 characters but it might just look desperate
March 18, 2009 at 1:14 pm
Pish — who cares about desperate. I prefer to term it “transparent” or “winningly vulnerable.” LOL
April 27, 2009 at 1:16 pm
Hello Kelli,
I couldn’t have written this article any better myself. I was recently feeling very disheartened about dating. I didn’t think I could ever find a woman who understood me, thought like me, and who wasn’t simply interested in me for my money. I never once considered dating another entrepreneur like myself…
Now that I know women like you really do exist, I will be on the lookout. Thank you for opening my eyes, and re-aligning my dating perspective.
April 28, 2009 at 4:51 pm
Hi Jonathan,
Yes, we do exist but since we all tend to work so hard, it can be a bit tricky to meet in a natural habitat. *grin*
Sometimes networking groups for entrepreneurs or small business types can be a good way to not only meet new biz contacts but new dates as well.
Good Luck!
May 21, 2009 at 10:14 am
I operate my own business, and I make it very clear to guys I date that my business is just that. Mine. Dating is entirely separate from what I do for a living. I’m not looking for a business partner. Basically, if anybody wants “numbers to back it up,” I just tell them to “fuck off.” End of story.
October 2, 2009 at 11:26 am
You’ve just described myself in your post. Eerie.
October 2, 2009 at 2:47 pm
LOL… it likely comes from not only being one myself but also being raised by one
October 6, 2009 at 2:52 pm
[...] kfox 12:49 pm on October 6, 2009 | 0 Permalink | Log in to leave a Comment 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 of 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 sweetie. via klawless.wordpress.com [...]
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October 14, 2009 at 12:07 am
Hi,
Thanks for this article. Really reflect on us. So true.
By the way I am an entrepreneur from Singapore.
October 18, 2009 at 10:14 am
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November 7, 2009 at 9:07 am
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