Date An Entrepreneur -- The Female Edition

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By Heather Payne (Head of Sales and Marketing, Pinpoint Social) (Based on “Date an Entrepreneur” by Bridget Porowski and “Date a Girl Who Reads” by Rosemarie Urquico)

Date an entrepreneur. Date a girl who spends her money on iPads and web apps instead of trips to the mall. A girl who doesn’t mind being told that her idea isn’t going to catch on. One who’s kept a running list of things she’s wanted to change since she was a kid.

Find an entrepreneur. You’ll know that she is one because she will always have her smart phone out. She’s the one skimming TechCrunch and Women 2.0, the one who can’t stop talking when she finds the idea she wants. Yes, she has a new idea to tell you about every week and yes, most of them will end up in her desktop Recycle Bin. But that’s what makes her great. You see a strange girl scribbling madly on an empty page in her notebook? That’s the entrepreneur. She can never resist a new opportunity, especially when it’s risky.

She’s the girl wearing jeans and a casual but stylish blazer while meeting with investors. She’s on her laptop at the coffee shop down the street. Her coffee is cold because she’s kind of mentally occupied. Lost in a world where anything’s possible and each no gets you one step closer to a yes. Sit down and chat. (She’ll give you a look because people are always sitting down to chat with her.) Ask her about her idea, product or service. Let her talk about product-market fit, angel investors, and IPO’s. If you dare to interrupt her she’ll give you a look, as most girls who create do not like to be interrupted. Try giving her a problem to fix, but only if you really want it fixed and fixed right. Ask her for her help or advice.

She’ll tastefully give it, while somehow making it seem like it was your idea all along. Funny how she manages that, isn’t it?

Let her know what you really think of [insert newsworthy startup story here]. Ask her for her honest opinion. Understand that if she says she understands calculus and teaches Python to #ladieslearningcode she’s telling the truth -– women don’t tend to exaggerate those things too much. Her economic predictions aren’t spot-on – but these days, whose are? It doesn’t matter, though, because she’s obsessed with generating revenue & profit and does a great job of saving her piece of it. She knows that she has to take care of herself. She’ll rub off on you, and before you know it you too will carefully compare grocery store prices by the ounce.

It’s easy to date an entrepreneur. Give her amazon gift cards –- and jewelry -– for Christmas and her birthday. Give her the gift of ideas while also making her feel special about being exactly who she is. Understand that, on your anniversary, she might be in New York doing a demo or in San Francisco talking to potential investors –- and forgive her for it. Her team might need her to finish their new build on the 14th, so don’t be shocked if she asks to celebrate Valentine’s Day a day later so you can be together (and take advantage of half-price chocolate). Let her know that you understand that ideas are love. Understand that she knows the difference between the present and the future, but she’s going to try to make life a little more like her vision for the future. Don’t try to stop her –- there’s no point.

She has to give it a shot somehow.

Lie to her. Like all self-assured people, she’ll understand your need to lie. Behind words are other things: incentives, motivation, meaning, implication…it will not be the end of the world.

Fail her. Because an entrepreneur knows how to create opportunity from failure. Because an entrepreneur understands that nothing truly comes to an end. That you can always create something from nothing. That you can recreate again and again and still be the heroine. That life is meant to have a challenge or two. Besides, it’s a good reminder that she has to focus on being the best she can be –- for herself first.

Why be frightened of everything that you lack? Entrepreneurs understand that people, like companies, grow. She will help you realize your potential. She will study you more than anyone. She’ll figure you out. That’s when you’re really in trouble.

You’ll want to propose to her long before she’s ready. She’s got a world to change, she’s always saying, and she’s in no rush. You’ll try to very casually slip it in dozens of times, always somehow losing your nerve at the last minute. Eventually, it will happen –- via Skype. When you least expect it to. And the seconds before she says yes will feel like hours. But if you’re lucky, she’ll say yes.

If you find a girl who creates, keep her near. When you find her up at 2 AM wrestling over her latest idea, make her a cup of tea and don’t be afraid to sit in silence. You may lose her for a couple of hours but she will always come back to you. She’ll talk as if the projections in her head and her Google Spreadsheets are reality, because someday, they will be.

You will smile so hard you will wonder why your heart doesn’t burst. Together you will create the vision for your lives. You might even have kids together. If you do, they’ll have strange ideas and even stranger imaginations. They’ll have the best lemonade stand in the city. She will introduce your children to Lego and math and consideration and beauty and generosity and building robots and cooking and JavaScript, maybe in the same day. You will love her more than anything and your relationship will always feel new and fresh, because ideas never get old. Because she’ll mess with your computer, but never your heart.

Date an entrepreneur because you deserve it. You deserve a girl who can give you the most vibrant life imaginable. Share your dreams with her, let her show you better ways of doing things and let her know you love her for who she is. If you want the world and the universe beyond it, date an entrepreneur.

This interview was originally posted at Heather Payne's blog.

Editor's note: Got a question for our guest blogger? Leave a message in the comments below. About the guest blogger: Heather Payne leads sales & marketing at Pinpoint Social, at a Toronto-based three-person startup. Pinpoint Social is the simple and effective way to run polished and professional-looking promotions on Facebook. She is also the founder of the #ladieslearningcode, a collective of women working to empower everyone to feel comfortable learning basic, beginner-friendly technical skills in a social, collaborative way. She blogs at heatherpayne.ca. Follow her on Twitter at @heatherpayne, or email heather [at] heatherpayne [dot ca]. Note the .ca!