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If I… Were a First-Time Female Entrepreneur

Posted on Jun 21, 2010 in Featured, If I... |

If I… Were a First-Time Female Entrepreneur

I wish I could go back in time. Not to tell my first boyfriend that his teeth really did bug me; not to revisit the moment my children were born; not even to undo all the terrible things I did to my parents as a kid. If I could go back in time, I’d approach my work life a lot differently from the get-go. If I were a first-time female entrepreneur, I would:

1. Go to email writing bootcamp. Learning to communicate comes with the territory of learning to do business. Women in business today misinterpret friendly communication with friend communication. Your colleagues are not your pals, and even if they are, email is not meant to be the grounds for planning happy hour while asking for an .xls report.  I’m not sure how drawing hearts over an “i” or smiley faces after our names somehow translated to appropriate communication tactics for women in business, but if you are guilty of it, you need to stop.

Here are my tips for proper female email communication (a) Get rid of any exclamation points in your email. Unless Chicken Little was right and the sky is falling, you do not need exclamation points to communicate your urgency or excitement over work issues (b) Forget any icons, shorthand, webspeak. Using TTYL in a work email is not only lazy, it’s disrespectful. Same goes for smiley faces. If you want a work colleague to know you are happy :), cheeky ;) or pissed-off :(, then you need to walk over to them and let them read your body language. More on body language later… (c) Never cross business and personal communication. Although it’s really cool that your workmate’s wife is in your spin class, work email is not a place to address such things. Refrain from finishing or opening your email with “Robyn said you had a great weekend…” — not unless of course, you want your email recipient to get mixed messages on the purpose of your communication. (d) Never say “much” or “love” unless you’re emailing with your mom. Blow off the “thanks so much,”  and “I’d love the opportunity.” Never, and I mean never position yourself as weak or desperate. The next time you to go sign an email, “Thanks so much!” think of me. And then, delete.

2. Using body language will generally work — but is it what you really want? I made a huge mistake during the funding of our first company. There was an investor who had the hots for @la_gringa and, as it were, he was a likely investor, a Silicon Valley insider and hot entrepreneur. We knew he liked blondes, we knew he was married, but during a investment pitch dinner, we intentionally flanked him with the two blondes in our company, dressed hot as you can imagine and ready to do business. In the end, we got what we wanted from him — a commitment to look at our company as an investment and a promise to introduce us to others who could too. And then, he stood up from the table and led @la_gringa outside to invite her to his hotel alone for a drink. And there it was. The pickle that we caused by using our female assets to gain traction in business. It took all three of us to get her out of that nightmare and, in the end, it made an uncomfortable situation an unbearable one. The business was strong enough to be funded without trolling in high heels up Sand Hill road. In the end, we didn’t get the investment. Learn from me on this one: you can woo an investor with your body language, but chances are, it’s not what’s best for your start-up.

3. Be a Social Light, not Socialite. The work that you do outside of your business to network both online and offline can truly help make or break you in entrepreneurship. Think about a few things before you engage: what are your goals for attending? What’s your elevator pitch? Who is your buddy? What social media tools are you going to use? Are you selling yourself as a brand or your company as a brand? Are you out for a drink and to get picked up?  Don’t even lie to me, I know this one way too well. No matter how you cut it, you are being sized-up in social scenarios. I always attend the Silicon Valley Tweetups. Why? Because some of my friends are there and I want to see them. I can go have a couple glasses of wine and chat in the corner with my friends. But you, you, little Miss-Hot-To -Trot-First-Time-Entrepreneur, you can’t.

Here’s how to be a Social Light First Time Entrepreneur, in no particular order: Look good * Take a work colleague with you, preferably a man * Sip on a single drink * Practice a casual elevator pitch * Have business cards with you (NO PINK BUSINESS CARDS) * Target three people to meet during the event * Ask questions about the said target’s work * Find anyone with the letters VC in their job title and watch how they operate * Make an introduction or two, it’s good for positioning * Leave before the crowd dies down * Send follow-up emails the next morning to your new contacts, add them to your database.

Here’s what you should gain from being a Social Light: A clean, crisp communication of your business, a brand association between you and your business to others in the industry, potential contacts, some learning on other companies and — if only slightly — better understanding on how to approach VCs. Social. Light. Female.

4. Find your tribe. The truth is, female entrepreneurs doing it right are rare. It’s helpful to find others who share your value system in business. It’s also highly valuable to find male entrepreneurs who you can take a lead from too. A recent deal required me to be working in the baggage claim area of SFO. I sat on the floor madly typing, searching for WiFi, using two phones and my computer, looking like a complete freak working a deal for a client. It hit me rather suddenly: There is no man on earth that would do this. I started saying outloud to a colleague: “What would a MAN do right now?” I sent a text message saying that I’d be available in an hour. I shut my computer and I walked out. My phone rang off the hook. I ignored it. Male entrepreneurs do things differently than females — learning the subtleties and taking a cue when to apply them is key to business strategy. Find a tribe of executives like you and you’ll find the resources and learnings are endless.

I’ve noticed over the past decade that women in entrepreneurship tend to emasculate their roles, and with reason: Silicon Valley is still very much a boys club. It’s an extraordinary challenge, but one that can be navigated with grace. Managing businesses with restraint and femininity can win both clients and respect. Lest we forget, ladies: You are your brand.