Find that Entrepreneurial Valentine.

I’ve talked about how to get and prepare for your first Investor Meeting.  With Valentine’s Day coming up, I figured some tips on getting and preparing for a first romantic date would be more helpful for the season.  (This post will be very hetero-normative, and aimed primarily at geeky/start-up men.  Here are some neat articles for those this will annoy, like it normally would me.)


Through my attendance at SF Beta, I’ve come to notice that there are a lot of single, intelligent, and interested tech boys out there, as well as women who are interested in finding them (yes men, they do exist).  Yet somehow, the meeting happens, and its all down hill from there…

So for the start-up men out there that I have come to know and love, here is some advice for chatting up that potential Valentine:


  1. Approach.  Before working on how to approach, you must first start the approach.  If you don’t have the confidence to come to me, I’m not going to waste my time going to you.  Yes, I noticed you staring at me from the door; I’m just choosing to ignore you till you get some balls.
  2. Have confidence, not ego. Approach with a smile, head held high, and a willing hand shake.  But do not approach with all of your successes and greatness on your lips.


  1. Have a conversation ready.  Do not come up to me, introduce yourself, and then expect me to fall head over heels that instant.  Be ready to talk and not stand with an awkward grin.
  2. A conversation takes two. Do not come up to me and leap into your newest start-up idea, a great technology you developed, or the tech gossip of the minute.  If my responses are fewer than 4 words, I either don’t care or you aren’t letting me speak.  I might as well just read your blog and leave you talking to the wall.
  3. Have a question ready. This falls in line with #1 and 2.  (“How are you?” doesn’t count).  We have Facebook now; do some stalking, and at least pretend you have an interest in my life and want to engage in more than physical intercourse with me.
  4. Don’t push too hard. Make me want more.  If you hang around me for more than 20 minutes at a mixer, our conversation better be damned good.  Otherwise, end it BEFORE it winds down and gets dull.  “Oh, I’m sorry.  My friend just got here.  Let’s catch up later (hand me your card).”  If, up until this point, things were going well, I will get back to you.
  5. A Card is not a Call To Action. I take back the “(hand me your card)”, above.  Think back to design school: have a Call to Action.  As you are leaving, let me know “It’s been great talking to you.  Do you have a card?  I’d love to catch up more later, ideally somewhere quieter.”  If she says no, give her yours, but make it clear you are honestly interested in talking.  On the same note, if I just hand you my card, thank you, and walk away, it does not always mean I am interested.  Don’t give up, but don’t get your hopes too high.


  1. Email first. Some girls will disagree with me here, but I hate when a guy calls me out of the blue.  I may not remember who you are, where I know you, or why you are calling; and your phone call just makes it uncomfortable.  I prefer getting an email or gchat first, and then taking it to the phone.
  2. A date is NOT a business meeting. Don’t trick me; be clear so I know what I am getting into.  I HATE when men ask if we can get dinner to discuss business.  Occasionally, people DO want to meet with me to talk business (surprise, surprise).  It’s one thing to say “I’d like to take you out to dinner.  I’m interested in learning more about what you do.” – That’s clearly a pick-up, thank you.  It’s another to say “I’d love to chat with you about a business venture I have.  Free for dinner next week?” – Ambiguity sucks.
  3. Dinner is a date.  Lunch is a meeting*.  Weekends are always dates. This is good to know whenever you are asking to take a woman out.  Be honest about what you want and pick an appropriate time.  (*If you have made it clear this is NOT a meeting, than know that Lunch is casual)
  4. Don’t get let down. You will get rejected, politely turned down, snubbed, ignored, etc.  But if you stay positive, hopeful, and strong while you are single, you will get dates as well.  The worst thing is the smell of desperation, so just relax and have a good time.  🙂


13 responses to “Find that Entrepreneurial Valentine.

  1. This is just…terrible.

    Also, s/now stand/not stand/.

  2. 😛 Aww, where is your sense of fun? It also may be terrible, but is pretty true.

    Im also, to clarify, NOT advocating that women shouldn’t approach when they want to. I just notice that men seem to approach first, so here was some advice for when they do.

    And thanks for the typo catch. Fixed. 🙂

  3. In my experience, women seem to seriously pick up body language and other subtle items that completely go over your average man’s head.

    I hate the concept that a woman is like a Rubik’s Cube whose level of attraction to you needs to be worked at like a puzzle. To take a woman that isn’t particularly attracted to you and *make* her feel attracted based on a long series of dates (that WE have to pay for) is way too much work. Besides, attraction isn’t really a choice you can make. It’s generally pretty instant.

    There are other ways to go about this, is all I’m saying. 🙂

  4. It’s true that you can’t make a woman who isn’t attracted to you fall head over heels. But those first few conversations can make a big difference, bringing a guy up a few points from the first impression.

    Im also not giving any advice on how to decipher a woman’s level of attraction to you. Hell, I can’t even do that.

    And you are just dating the wrong people if you have to pay for all of the dates. I accept that the first date is paid for by the person who asked, but after that it should definitely alternate.

  5. I’m glad more and more women are starting to pay for dates. In Texas, where I live, women are generally old-fashioned, and…well, dumb.

    Also, I agree that the first few conversations make a big difference. Based on what I’ve learned, if a man makes a lot of female friends and understands the social behaviors that generally work, he can practice the application of those behaviors. Just like an algorithm.

    5. Call her up at 3 AM and just breathe into the phone.

  6. Nick seems to figured out all of Texas based on his personal experience. I too live in Texas, and I have found women here to be generally smart and willing to alternate paying for dinner. Perhaps what you see is a reflection of yourself, Nick?

    Outside the tech community, many (most?) women find e-mail a bit formal, and I am not a big fan of phone conversations either. I’ve found facebook messages to be a perfect middle ground.

    Good post 🙂

  7. Thanks, Arvind.

    Agreed, FB messages are also a great middle ground. I suggest texting, too. 🙂

  8. Hah! Yes, I’m generally a complete dolt and I would -never- pay for a date. Ever.

    Spot on!

  9. Frequently, at tech conferences, I witness socially awkward software programmers making advances at the perky, cheery social butterflies who work in marketing and PR. The flirtation often starts off well with glances and smiles, but falls apart during the conversation phase.

    It seems most techies (this applies to techies of both genders) resort to well-rehearsed speeches about their domains of expertise when they feel insecure. So when a charming PR girl does decide to give one of them the time of day, they seize the opportunity to impress her by launching into a monologue (quite possibly a memorized PowerPoint presentation) about cloud computing or encryption algorithms. Some of them don’t even pause to give the girl a chance to ask question (or redirect the conversation to some other topics). I don’t know if I should feel sorrier for the tech bachelors who’re doomed to repeat this mistake or the girls who must routinely endure this.

    I hope some tech boys and girls find their Valentines. They deserve romance just as must as the rest.

  10. Fixed typos, sorry abt that!

    I’m female and I pretty much disagree with this analysis. I think most of the points are specific to the tastes of the OP and of course, that’s not how the rest of us work. Guys, if you want to meet a girl at SF Beta or anywhere really there are only 3 things you should keep in mind.

    1. Look (and hopefully be) confident and comfortable in your own skin. One thing the OP got right is that girls hate desperation on guys. It’s just not manly.

    2. Have some money. Yes, this sounds shallow but to be honest most girls are concerned with dating guys who have a good, stable job that pays well. This doesn’t mean we’re all gold diggers but money is important.

    3. If she doesn’t seem interested (looks like she wants to talk to someone else, isn’t looking at you directly) please move on. The girl:guy ratio in SF largely favors the guys so you have many more options than you think.

    3.5 It helps to be tall (again with the shallowness!). I have many friends who will turn down a short dude even if he’s confident and has a good job. Girls just like tall guys – I’m talking 5′9” or taller.

  11. Hmm…doesn’t sound like you disagree with all that much. Primarily I was saying: be confident and read her responses well. I

    t does help to be tall, but I wouldn’t include that because I don’t think a guy shouldnt try because he isnt – I’m dating someone a good 4″ shorter than me right now.

    I also dont EVER ask a guy about money, personally, atleast not until we are quite serious. He can’t bum off me – I’ll notice that – he has to be self supporting in SOME way, and be motivated in his passions. But being rich because of those things is certainly not a requirement.

    Uh….when was the last beta you went to? The girl:guy ratio at SFbeta favors women by FAR! It’s about a 40:60 split. That said, most men aren’t there to pick up women, so if you are you have an advantage.

    In the end, sure, it’s all just one’s opinion and desires.

  12. hey cassie,
    i’m a life & dating coach and i LOVED this article!

    i agree, one shouldnt ask the other about their income…it’s more about the richness in his life, than their wallet.

    for me- drive, soulful and balance is far more important than a VP who crumbles inside.

    glad my friend sent me this link. i really liked how frank, succinct and it’s application to the business theme.

    keep up the awesome blog.

  13. Complex!

    Making effective business connections requires honed networking skills. Making effective dating connections requires a PhD. Way easier to work at becoming the next uber techbiz god with serious bank, that will open some doors, cover some flaws.

    In the meantime, celebrating celibacy!

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