Finding an Entrepreneurial Valentine

(Please note, this was written for V-Day LAST year on an old blog.  But I am trying to collect all my writings in one place.)

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. I’d love to catch up more later, ideally somewhere quieter. Do you have a card?  Mind I ping/call you soon?” If she says no, give her yours, but make it clear you are honestly interested in social, not business.


  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 someone 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. 🙂

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