Date An Entrepreneur, Female Edition – A Reprise

Jan28

On August 19th, 2011, I wrote a blog post that easily became the most widely-read thing I’ve ever written. It was a surpise to me – I wrote the thing really quickly, late at night, as a reaction to a blog post I came across called “Date an Entrepreneur” (which was based on another post called “Date a Girl Who Reads“). You can check out my post from August 19th here.

The thing that’s funny is that I wasn’t yet an entrepreneur when I wrote that post.  I was working at a startup, and we’d hosted our first Ladies Learning Code workshop, but I hadn’t yet taken the leap.

Now, of course, that’s all changed. Today, I’m definitely an entrepreneur – I make a living by working for organizations that I’ve founded. I’m responsible for paying salaries, carrying a commercial lease and remitting taxes, not to mention all of the fun stuff like making sure people love being HackerYou or Ladies Learning Code customers, defining and executing strategies,  and working with my team. I’ve learned a lot since August 2011, and certainly matured as a person, a woman and an entrepreneur. Looking over my updated post below, and comparing it to the one from 2011, it’s pretty interesting to see what’s changed. And what’s stayed the same.

So, here it is. A reprise of my post about dating an entrepreneur from about a year and a half ago. Would love your thoughts.

Date an Entrepreneur, Female Edition – A Reprise

(An update to my post from August 2011 that was based on “Date an Entrepreneur” by Bridget Porowski and “Date a Girl Who Reads” by Rosemarie Urquico)

Date an entrepreneur. Date a woman who spends her money on programming courses and productivity tools  instead of trips to the mall. A woman who doesn’t mind being told that her idea isn’t going to catch on. One who can scan the landscape and identify opportunities that other people just can’t or won’t see.

Find an entrepreneur. You’ll know she is one because of all the tabs she has open in her browser. She’s the one skimming industry blogs, the one who can’t stop thinking about how she could do more, be better. Yes, things with her business move quickly and yes, she has more ideas than any one person can reasonably handle. But that’s what makes her great. You see a woman writing thoughtfully on an empty page in her notebook, with a Google spreadsheet open and her iPhone out? That’s the entrepreneur. She can never resist exploring a new opportunity, but she’s learned by now that not every idea is ultimately worth pursuing.

She’s the woman wearing jeans while meeting with investors. Or customers. Or anyone, really. (Suits and blazers have seen nothing but the inside of her closet for years.) 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 running a business and changing the world is really hard work. Sit down and chat. (She’ll give you a look because she’s working on some kind of deadline, as always.) Say something that will catch her attention (good luck), and if she seems engaged, ask her about what she’s working on. Let her talk about education, technology, and what she’s got coming down the pipeline. If you dare to interrupt her without a good reason, she’ll give you a look – but that’s just because most people don’t like being 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 if you need it – she’ll always help if she can. But she’s learned by now that she’ll be better able to help others if she helps herself first.

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 likes calculus and video games and is learning Ruby on Rails at HackerYou 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’d rather invest in people, like Katherine Hague, or in her own businesses. She’s obsessed with generating revenue and profit and does a great job of saving her piece of it. She knows that, in this day in age, 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 and stock up on household staples when they’re on sale.

It’s easy to date an entrepreneur. Give her Adafruit gift cards – and jewelry – for Christmas and her birthday. Enable her creative side while also making her feel special about being exactly who she is. Understand that, on your anniversary, she might be in New York speaking at a conference or in Halifax launching a new Ladies Learning Code chapter – and forgive her for it. She might be in San Francisco on the 14th, so don’t be shocked if she asks to celebrate Valentine’s Day a day later so you can be together. Let her know that you love the passion she has for what she does. Understand and trust that she knows the difference between the present and the future, but she’s going to change the world to make it reflect her vision for the future. Don’t try to stop her – there’s no point.

She has to give it a shot somehow.

Don’t lie to her. Honesty has never been more important. Don’t be one of those people who just tells her what she wants to hear.

She’ll fail sometimes, and that’s okay. 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 that there are lots of ways to create value. 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.

Don’t worry about whatever you feel 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 woman who creates, keep her near. When you find her up at 2 AM wrestling with a bug on her websites that she’s already been working on for hours, make her a cup of tea and grab your laptop or a book and sit with her. You may lose her for a couple of hours but she will always come back to you. And when she does, she’ll either be absolutely frustrated, finally giving in to her sleepy eyes, or she’ll be on cloud nine because she did it. Either way, in the morning, she’ll be back to normal, so be sure to appreciate those precious moments of emotion.

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. (It’ll have a website, and probably an app.) 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 woman 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 post is dedicated to Shawn Konopinsky, the best partner I could ever dream of. So happy that we both found entrepreneurs to fall in love with.

Now I’m Really an Entrepreneur

Jun06

I’ve wanted to be an entrepreneur for a long time. Not when I was in university (back then, I wanted to be CEO of a Fortune 500 company), but sometime between graduating and landing my first real job, I realized that I just wasn’t going to be able to make a career out of working for the man. Even after that realization, it’s taken me a long time to get here. As of today, though, I’m really an entrepreneur. And I’m effing excited about it.

(Want to skip to my new venture? It’s called HackerYou. Click here to visit the site, click here to read our press release, and click here to follow us on Twitter.)

When I moved to Toronto in May of 2010 (you know, after living in China for 15 months and then dropping out of grad school), I wanted to join a startup. But, of course, I didn’t know a single person in Toronto’s tech or startup communities, and as a recent grad, I didn’t exactly have people clamouring to hire me…to do anything. I was lucky to land a job through Laura Plant (yes, the one from Ladies Learning Code) and I worked for a year at a big company. And that was enough of that.

Just before I left BigCorp Inc. to join a startup as employee #2, I was in LA for work. And if you’ve heard of Ladies Learning Code, you know the story. I stumbled upon an event via Women 2.0. Run by the PyLadies, it was a workshop designed for women who were beginners to Python but ready to learn, which described me perfectly. It was their first workshop ever, and it was great, and I returned to Toronto and tweeted about how we should have a similar group here. Almost immediately, I started receiving emails from people who were interested in the idea, and when I’d received about a dozen, I planned this event. 85 people registered, there was a great turnout, and as a group we decided to run our first workshop exactly a month later. About 20 people were involved in pulling that first event off – it sold out in a day, and was definitely a success! I was surprised, and really excited.

We started planning workshops every month, and they started selling out faster and faster – like, sell-out-in-five-minutes fast. By the end of 2011, my team (by now, four of us) made the decision to start offering two workshops a month. Now, almost 2000 women (and men) have participated in a Ladies Learning Code workshop. Over 400 developers and designers have signed up to volunteer their time. We run a March Break and summer camp for 9 to 13 year old girls. And just yesterday, we announced that we’re going to be offering a couple workshops in Vancouver this summer.

But although I definitely accept the compliments offered to myself and my team for the job we’ve done in starting and growing Ladies Learning Code, and although I truly appreciate being considered an entrepreneur, I haven’t felt like one. Not until today.

Maybe it’s because Ladies Learning Code is a not-for-profit. Maybe it’s because I got lucky, stumbled onto the idea, and just held on for dear life. Maybe it’s because the point of Ladies Learning Code was never to find a repeatable and scaleable business model (I mean, the thing has a business model, but it sure as hell doesn’t scale. Not easily, anyway.) Maybe it’s a combination of all of those things. It might even just be in my head. But I just haven’t felt like an entrepreneur yet.

Either way, it all changes today. Today is the day that I’m making a specific decision to bring something into this world that wouldn’t exist otherwise. I’m putting my money where my mouth is by making an investment in turning this idea into reality. In line with Steve Blank’s definition of a startup, my purpose now is to find a repeatable and scalable business model. And this time, I want to do something that will have a positive impact and make a profit, because I believe it’s possible to do both.

Want to see what my team and I built? Check it out: http://hackeryou.com. And be sure to follow us on Twitter – we’re @thisishackeryou.

A Note To Young Treps: Put Down The Ramen

May13

I wrote a piece for YoungEntrepreneur.com, and it was published earlier this week. Check it out:

Whether it’s long hours, late nights or surviving off just the most basic of staples — we’ve all heard the stories of startup founders working toward Ramen profitability. Although these tales are popular, and sometimes even glamorized, are they a necessity for anyone looking to start up?

I don’t think so. After all, I’m an entrepreneur. My startup is less than a year old. Yet, I live in a good-sized apartment in a nice area of Toronto. I have an iPhone, a couple of computers and an iPad. I have patio furniture and I host dinner parties. I rarely buy groceries, choosing instead to eat out or on the go. Recently, I made a five-digit investment in fellow entrepreneur Katherine Hague’s startup, ShopLocket. And despite the fact that university cost me $100,000, I’ve been financially independent (and debt-free) since I moved out at 18.

Is it luck? Partially. But most of it comes down to being financially savvy. Here are three tips to help you pursue entrepreneurship without having to resort to Ramen:

Read the rest over at YoungEntrepreneur.com…

Defining the role of a teacher

Apr02

(From Seth Godin’s “Stop Stealing Dreams“)

It used to be simple: the teacher was the cop, the lecturer, the source of answers, and the gatekeeper to resources. All rolled into one.

A teacher might be the person who is capable of delivering information. A teacher can be your best source of finding out how to do something or why something works.

A teacher can also serve to create a social contract or environment where people will change their posture, do their best work, and stretch in new directions. We’ve all been in environments where competition, social status, or the direct connection with another human being has changed us.

The Internet is making the role of content gatekeeper unimportant. Redundant. Even wasteful.

If there’s information that can be written down, widespread digital access now means that just about anyone can look it up. We don’t need a human being standing next to us to lecture us on how to find the square root of a number or sharpen an axe.

(Worth stopping for a second and reconsidering the revolutionary nature of that last sentence.)

What we do need is someone to persuade us that we want to learn those things, and someone to push us or encourage us or create a space where we want to learn to do them better.

If all the teacher is going to do is read her pre-written notes from a PowerPoint slide to a lecture hall of thirty or three hundred, perhaps she should stay home. Not only is this a horrible disrespect to the student, it’s a complete waste of the heart and soul of the talented teacher. Teaching is no longer about delivering facts that are unavailable in any other format.

[Note from Heather: This post from Seth Godin makes me think about what we’re doing at Ladies Learning Code. Somehow, we’ve made almost 1000 women (and men) into passionate learners – for a day, at least – about a topic they otherwise might not explore. Sure, we use slides. But there’s something about the experience that puts Ladies Learning Code workshops in a new category. This isn’t school.

I find it pretty interesting to note that most of our Lead Instructors and Mentors are in a teaching role for the first time ever when they join us at a Ladies Learning Code workshop. And no one on the Ladies Learning Code team has a background in education. The funny thing about that is that it might be why what we’re doing works.]

Non-technical? How to Join a Startup in 7 Steps

Sep05

[This post was originally published on TechVibes.com]

So, you want to join a startup?

I know how you feel. After a year in a corporate marketing role at an established international firm, I was really happy – but I also felt like something was missing. I just knew (actually, I’d known it for a while) that startup world is where I belong. In May, I decided to begin looking for my next opportunity, thinking that it would take me at least four months, or even six, to find the type of startup gig I was looking for. To my utter astonishment, my job search ended in less than three weeks when I received a great offer from Pinpoint Social. (I also had a few other opportunities in the pipeline, just in case.) I’ve thought a lot about my job search experience since then, and I think I’ve figured out the seven steps that should be followed for anyone who wants to go from corporate to startup life in less than three weeks. Here they are:

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Date an Entrepreneur – Female Edition

Aug19

(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.

So, Who Won Startup Weekend Toronto?

Jun06

(Yes, I’m going to tell you who won. But I’m not going to let it ruin this post, for those of you who haven’t heard the news yet.)

I wrote another blog post this morning (well, I aimed for morning…it actually came out in the afternoon) about Startup Weekend Toronto and the progress the teams had made by then. Check it out below!

SPOILER ALERT: Want to know who won? Click here to see who came in third place, here for second, and click here to see who won the grand prize!

Check out the post below – if you have a chance, I highly recommend visiting the websites and landing pages of the other teams that competed. Many of them will continue to work together post-Startup Weekend, so you should sign up now for beta access!

Let me know what you think of the post in the comments section below.

PROGRESS UPDATE @ Startup Weekend Toronto

Written by Heather Payne (@heatherpayne)

Hey everyone! It’s about 1 pm on the third and final day of Startup Weekend Toronto – and the energy here is awesome!

Didn’t make it out to Startup Weekend Toronto? Curious about the progress of our teams after reading this post? Or, maybe you’re at Startup Weekend but are drowning in code and haven’t had the time to take a look around and see what everyone else is up to. Not a problem – we’ve compiled a #SWToronto Progress Update! Check it out below.

In no particular order…

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Report from Startup Weekend Toronto

Jun05

It’s 10:19 pm. I’ve been hanging out in the Burroughes Building (the Startup Weekend Toronto venue) since 9 am. And it’s not like we’ve been taking it easy, either – we’ve been building stuff.

Want to see what I’m working on? Check out www.epicrise.com. Let me know what you think! (Either with a comment below or tweeting me at @heatherpayne.)

We aren’t the only team doing cool stuff this weekend though. This morning, I (co-)wrote a blog post summarizing the 20 ideas that made it through yesterday’s voting process – over 70 ideas were pitched. (Sadly, only 3 of the Top 20 pitches were presented by women…we’ll have to improve that ratio next year!) Although we originally posted the summary on the EpicRise blog, I want to share it with you here. See below!

Startup Weekend Toronto 2011’s 20 Winning Pitches

By Heather Payne and Melissa Crnic

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