horsepigcow

A couple of months ago, a mentor of mine pulled me aside and gently made an observation…

“Tara…you are a great presenter. You are passionate and can make any story or idea sound interesting. I’d want you to sell anything that I was trying to get out into the world…HOWEVER…when you talk about yourself or your company, you sound uncertain and nervous. You lose that passion. I just wanted you to know how you come across.”

It’s true. And it is the craziest thing. I DO believe passionately in what we are doing with Buyosphere. I’m excited and energized with how awesome the site is progressing and I know in my heart that we are solving a real problem with what is being launched in a few weeks. I’m so excited, I’m up at night feeling giddy and have great ideas on how to grow and monetize and build a really strong, amazing business.

So why the hell do I get sheepish when I talk about it to others?

Because braggarts are irritating and I can’t de-couple myself from my startup. The answer lies in how I tell the story. This is how I’ve been telling it since the beginning:

1. I’ve been dreaming about solving the purchasing experience online since 2007 (I have)
2. My co-founders and I are a tight-knit family who have grown together a LOT over the past 18 months (we have)
3. The broken purchase experience relates to a story from 2007 – a search for a black skirt online that took me 3.5 hours and going to 13 websites (it did)

But none of these things matter. Yes, they matter to ME. This IS where my passion lies. But all three of these things make my business WAY too personal for me. So when I pitch my company, I’m essentially telling a potential investor, “Invest in me and my dream.” Not a good sell. And, when that potential investor passes, he or she is passing on my dream, not my company, so it feels much more personal.

Buyosphere is my precious. And rejection of Buyosphere feels like a personal rejection.

I now understand that this is nuts. And I don’t know if it’s a ‘woman’ thing or what, but it’s definitely a ME thing that I need to un-learn. Yes, investors say they ‘invest in people’, but they aren’t investing in people’s dreams. They invest in people they trust to build a business, sell that business, grow that business and, ultimately, make them a lot of money. These are not charities. They could give a flying snake that I’ve grown or what my shopping woes are. They want to know the big picture and how we get there. No preciousness. I’m starting to understand what some (who are very helpful mentors) have referred to as ‘fluff’.

Someday when I write the chapter on ‘how to speak VC’, this will be the very first lesson (I have yet to know what the next lessons are). Very analogous to how the ring drove Smigel crazy and turned him into a paranoid Gollum, being too coupled with your idea will lead to heartbreak over time. Every rejection will become a personal wound. After a while, you will feel alone and hyper protective. It’s a selfish thing. I have two co-founders whose ideas, input and implementation are just as formative (if not more) than my own. Investors become partners who also bring ideas and input into the mix. It is not ‘my precious’, it is a company. A company that I believe in and I’m excited about and that I will work hard to help succeed and be a great tool that will help people.

I wanted to share this revelation because I don’t think I’m the only one who is stuck in this paradigm. I’ve heard others talk about their companies in the same way. And when you are so close to the idea, it closes you to input and growth. Knowing, instead, that this is your job (not your dream) and your job is to make your company wildly successful opens you up to more ideas and helps you see where you need to let go of others.

I’m working on shifting this paradigm now, but it won’t be easy. I’m seeking outside help from people who can take me through the withdrawal steps:

1. Reframing the pitch – de-coupling it from my ‘dream’ and speaking to the business opportunity
2. Rethinking my relationship with Buyosphere – if it’s not an extension of my identity, what is it? And really, who am I?
3. Becoming the biggest advocate for Buyosphere I can be

It won’t be simple, but it’s highly necessary. And it will release me of the pressure I feel when I talk about Buyosphere. I hope.

Jolie O’Dell, who is one of my favorite people in the world tweeted something yesterday that got the women of the tech world (and many men) up in arms:

It also ignited quite a lively backchannel conversation amongst the various women in tech groups I’m part of. The reactions (including mine) ranged from “I can see her point, but ‘embarrassment’ is a harsh way to put it,” to “OMFG &*#(&#)@#*@!” Mine was somewhere in between, but the biggest thing that struck me was how familiar it sounded.

And it isn’t a familiar because I’m a woman founding a fashion/shopping site, it’s familiar because in every single profession where the population of women starts growing, the same thing happens and the same sentiments get voiced.

As the number of women doctors grew, there was (and still is) an outcry because female physicians outnumber male physicians in pediatrics and female residents outnumber male residents in family medicine, obstetrics and gynecology, pathology, and psychiatry.

I’ve heard the same said about women lawyers: they pick ‘softer’ forms of law to pursue such as non-profit, family, government and general practices. Women are less likely to run a firm or become partners at a firm and more likely to be in-house council.

But this isn’t the issue. Nature or nurture or interests or whatever, if more women choose to practice medicine, law or do startups around the stuff we are familiar with, I’m not too concerned. I figure as time goes on and our entrance into professions becomes more common, things will even out. What I’m concerned about is the sentiment around the decision to pursue more feminized versions of these professions. The feminine itself is negatively valued.

Feminine = Soft/Bad/Stupid/Shallow/Underachieving/Embarrassing ??

Think about how we assign value to certain things like: logical vs. emotional. Or independent vs. dependent. Or analytical vs. intuitive. I’ll bet when you read the words, you instantly understood what ‘gender’ was assigned to each (and when I say gender, I don’t mean men vs women. I mean masculine vs. feminine.). Neither is better or worse, but depending on the context, there is a differential in how they are valued. And in the tech industry, being emotional, dependent and intuitive is a death sentence…unless you are a man who has a ‘proven’ record (proven being the uber masculine differentiator).

The same goes for types of startups. Business tools = good. Analytics = good. Content aggregators = good. Productivity apps = good. Shopping = bad. Fashion = bad. Babies = bad. UNLESS…you are a man. Diapers.com was founded by two men. They are super rich now. Zappos.com was founded by men. They’ve done pretty well. Amazon, Bluefly, Kaboodle, Shopstyle, Stylefeeder, eBay…the list goes on. One could argue all of the founders behind these have done pretty well for themselves and even the sites that aren’t super popular were acquired for good money and had good exits. I don’t know…sounds like a shopping (baby and fashion) startup is a pretty solid, awesome, smart, hardcore, good, kickass type of startup to have.

So why is it so embarrassing to have so many women entering the startup world through such a lucrative entry point?

Because, well, it’s embarrassing because we are so few and there is so much hope pinned on our performance. We’ve been begging and screaming to get included and then we show up in high heels talking about designer snugglies and nailpolish. Damn these women being all womeny talking about women stuff! Who invited these ones to the party? Where are the serious female entrepreneurs?

Right here. In high heels. Wearing great nailpolish (I swear by this stuff…it’ll extend your manicure for…nevermind). I’m emotionally and intuitively navigating through this. And I’m dependent on more people than I feel comfortable with: my customers, my users, my co-founders, my advisors, my boyfriend, other startups, my friends, the weather, the economy…you name it.

When I moved to San Francisco in 2005, it took me about 6 months to deny myself my femininity. It wasn’t fashionable to be fashionable. I moved to SF with a closet full of designer dresses, suits and shoes and within 6 months all I was wearing were jeans and t-shirts. I am ecstatic to see photos of events filled with women in dress clothes and high heels. My only embarrassment lies in that I didn’t have the *erm* balls to be the woman I am back then.

Instead of embarrassed that there are so many women doing startups involving fashion/shopping/babies, I’m proud. I’m proud of a truly inclusive tech scene where women can women, men can men, women can men, men can women and all sorts of other genderific combinations thereof. And I, for one, welcome the pink ghettoization of the tech startup scene – at least for the time being – because it means women are making a grand entrance. And what an entrance it is!

Honesty, as it seems, isn’t always the best policy. Or at least it seems that honesty CAN be a best policy if it has the right PR spin.

Years ago I learned a HUGE lesson: ‘fake it until you make it’ has a cost and, if the gamble doesn’t pay off, you’ll be saddled with more than you can handle afterwards. It was my first business and everyone advised me to look more experienced and more established than I was. Since I didn’t have an official office, I needed to pretend that I do. And since I was new, I needed to come on the scene with a bang. So I spent a whole bunch of money I didn’t have up front and didn’t tell anyone that I was going in debt for it. Long story short, it seemed to work for a while, but when the market fell out beneath me, I was saddled with more debt than I could bring in income. I had to get a real job in order to pay for my previous ‘faking it’.

Lucky for me, the social web rose up and radical transparency became all the rage. Now everybody was talking about how they worked from home and coffee shops, how they don’t always know what they are doing and bootstrapping became an honorable way to start a business. Where I once needed a rent-an-office space, brochures, fancy website, answering service and other expensive collateral, I could now merely have a blog, a laptop and a bunch of Moo Cards. This no longer seemed amateur because everyone was amateur and amateur was the new professional.

But something has shifted back over the past 5 years or so since then and there seems to be a resurgence of the ‘Fake it til you make it’ battle cry. I’m not sure if it’s because we could get away with our scrappy little amateur web businesses when we were still on the bleeding edge and now we are part of a serious money-making industry or whether it’s just a natural pendulum swing to counteract the ‘We Live in Public‘ viewpoints of the world that were hyperbolically transparent (and even shocking to an open advocate like myself).

Either way, Faking it is the new transparency and I don’t think its resurgence is a good one. Why not?

1. By faking it, we fail to share our struggles – I know that’s kind of the point of faking it and all, but if nobody shares they are struggling, nobody will know anybody else is struggling. That results in a whole bunch of people feeling quite isolated and scared and thinking that they must be big, fat losers because they are the only ones in the whole wide world that struggle. Funny thing…I shared my struggle at TEDxConcordia (6,000 views) and at NXNE Interactive (167,000 views) and both were passed around like wildfire. I’ve never received so many thank you emails. This struck a nerve. People were thankful I shared because they no longer felt alone.
2. By faking it, we fail to learn what it takes to REALLY make it – the amount of advice posts written by failing startups that other startups followed and promptly failed by is astonishing. Same with speakers at conferences who delve out advice for ‘how to do it right’ when they know full well that their community is crumbling, they are running out of money and their days are numbered. This is just wrong. People wanting to do startups look up to people doing them. And they aspire to be them. Let’s not pass along our mistakes, only our lessons.
3. By faking it, we ignore reality. I recently read 10 Facts About the Condition of American Families that Will Blow Your Mind at Business Insider. Wow. I think it’s time for America to stop faking success (“Look at how Wall Street is recovering! Look at how much money is being invested! People are working/buying again!”) and start facing reality. There is something fundamentally broken here. Admit it, grow some humility and fix it so we can achieve REAL successs. Because the longer you lie to the world, the more you will believe it yourself and the longer you will struggle. You only increase your chances of success when you admit your reality.
4. By faking it, we perpetuate a culture of lies. It’s the viciousest of vicious cycles, really. If we all just admitted we struggle, nobody would feel like admitting it would make people think they were a big loser. By ‘staying in the closet’ about our fears, doubts and stumbles, we keep that closet closed for future generations.
5. By faking it, we are just plain lying. If it was my money on the line, I’d want to know what was going on with the companies I invested in. 100%. I wouldn’t want to be surprised at a board meeting that the company I see as doing amazing things is about to close down because of legal battles, especially if those legal battles had been going on for ages and I could have helped. I’ve heard this story and many others from advisors, investors and employees who had no idea the company they worked for was in trouble. Yes, yes…revealing every little thing isn’t good either. You need to help people feel like you can handle the small stuff. But when you are running out of money or being sued or discover you were on the wrong path or whatever is a bigger deal, it’s time to reach out and get help.

Now, this being said there IS such thing as TOO MUCH INFORMATION. I would never name names (even thinly veiled), give specific details in a legal or financial case, talk ill of anyone who wronged me (not naming names – but you can talk about lessons learned…how to avoid situation X) or personally attack anyone. You have to use your judgement. The way I approach transparency is: “This is how I am struggling. This is what I’ve learnt. This is what I’ve done wrong. This is what I did right. This is how things are broken. Please keep in mind this is my perspective. Anyone else want to add/share?” Sometimes I wait until this can be told in retrospect, sometimes I talk about lessons as I’ve learned them.

Of course, this is also changing for me as time goes on. I find myself clamming up more and being less involved in discussions that are heated in this area. I’m aware that my own behavior reflects on my company, which means the other people who work with me have to bear the brunt of my sometimes misguided opinons. So I stay away unless I have something personal to share that I think will help others. Mostly I speak of my own mistakes now.

And I’ve had friends in the industry advise me to keep quieter in general, but as I said above, this won’t help anyone (even though I know their intention is to protect me). And I don’t think it will help me (or anyone else) in the long run. I’m not stupid or reckless (mostly!) and I’m more than happy to admit it if I make a mistake. Feel free to tell me when I’ve crossed the transparency/TMI line.

I know that we had a special luxury in the early days of the rise of the social web business when we were the scrappy revolutionaries and now that we are starting to make bigger impacts and affect real lives, we need to think about how our behavior touches other people. It’s no longer about a revolution (was it ever?), it is now about changing the world to be a better place. But I do believe that transparency can grow up with us, too. It doesn’t get left behind, it just evolves to be central to the way we interact. It’s a better way and it’s definitely better than faking it.

I love shopping. I do. It’s no secret to the people around me. And it’s pretty much killing me right now to be a broke startup entrepreneur who looks at amazing, gorgeous new objects of desire every single day on Buyosphere that I cannot afford. So, of course, saving money on the stuff I want and need is a highly desirable thing.

Then why do the plethora of shopping discount, daily deal and coupon sites leave me so darn cold?

I think it’s because, instead of helping me afford the stuff that I need and want, there seems to be an endless stream of messages tempting me to spend my money on stuff that is shiny and lovely, but that I never knew I desired before they appeared in my inbox. In fact, by spending my money on these lovely objects of distraction, I’m getting further away from being able to afford the stuff I really want/need.

Another issue could be that there are just too many shopping deal sites all at once. Or maybe the coupons/deals/offers aren’t what we need as consumers after all. Perhaps it turns out that I don’t need a new pair of cheap shoes or new accessories every month. Maybe I just need to be able to afford one or two pairs of really good shoes per season, or that amazingly unique accessory by that hard to find local jeweler that makes me look European in every outfit…even jeans and t-shirts. Or maybe I need a better way to find my way to these items.

Hmmmm…if only someone could come around to help us shop SMARTER instead of just MORE. Okay, that is a bit self-serving (as that is one of the core objectives of Buyosphere – egad, I can’t wait to unveil our next phase which I think will really help make this a reality), but it’s true and it is exactly the issue that all of these hot new startups are going to face.

At the end of the day, we don’t need anything that encourages consumption. We’ve done just fine on that level for years. What we need is a better/faster route to finding that perfect thing for me, which requires the sellers who have that perfect thing for me to figure out how to find me in that exact moment and the sellers that don’t to get out of my way. THAT will be the killer social shopping site.

note: stay tuned…

It’s a simple statement, but not a simple thing to do. Product/market fit is truly the ONLY thing that matters and achieving it before you run out of money is the key to winning. It’s why companies raise a whole bunch of money:

MORE MONEY = MORE TIME = MORE LIKELY TO WIN

…or not. Sometimes more money equals more waste, too. And we are seeing this a great deal right now. Sometimes more time is not the best thing to give an entrepreneur. Finding that balance of time and money will help us be hungry and creative enough to find the best product/market fit.

Finding that Product/Market Fit

There is no silver bullet here and I’ve found it incredibly enlightening to be on the product side of this one (not the pundit or consultant side). However, I’ve come across some really great resources that will help streamline the process of finding product/market fit:

1. SOLVE THE RIGHT PROBLEM – If this seems obvious, you are fooling yourself. One of my favourite stories of all time, retold by Aza Raskin, is that of Henry Kremer’s search for a human-powered flying machine. Read it. Turns out the problem wasn’t that they needed to solve human-powered flight. The problem was that the prototypes took to long to test. Fail fast and iterate often.
2. LIMIT YOUR MARKET – finding product/market fit for EVERYONE is like finding a pair of pants that fits everyone. It doesn’t exist. Seriously. Narrow your market. And not to 18-35 year old males. Figure out who that ONE person is. Not a profile or a fictional person, either. If you can’t find a single living being that is that person, you don’t have a market. Hell, solve it for yourself if you have to, but be careful because you are seriously biased.
3. EAT YOUR OWN DOGFOOD AND REALLY TASTE IT – do you really think what you’ve built is amazing? Seriously? I’m the first to admit that though Buyosphere is coming along nicely, it’s quite a ways away from being useful to anyone but someone who likes to keep track of the stuff they buy…and even then it is clunky as all heck. I can admit that. And I’ll continue to be my biggest critic and breaking my own product until I can honestly say, “This is freakin rad”. I won’t be happy until that day.
4. RESEARCH RESEARCH RESEARCH – Talk to your customers and potential customers. This one is hard because you have to know what information to filter and what to use. But I love the story of AirBnB’s early days of flying to New York every weekend and knocking on doors. Not only did they use their own service, figuring out what sucked and what worked, but they talked to potential customers, hosts and travelers to find out more information. This is where limiting your market can also come in very handy!
5. LOOK TO OTHER MARKETS FOR CLUES – I love reading outside of my field. Innovation can be found in other markets and examples unrelated to yours. Connect the dots. Hell, much of the innovation of the media industry has come from the porn industry. They solved the distribution of media to viewers before the rest of the industry realized there would be a demand. Who is capturing an audience that you can beg, borrow and steal ideas from?
6. UPDATE OLD IDEAS WITH NEW TWISTS – Groupon is just a new way to present coupons. That’s it. There is nothing seriously innovative about it. Except that it IS innovative in that it gives HUGE discounts and not just a $0.05 here and there. Oh…and the way it’s described as sexy instead of cheap to use a Groupon.
7. UNDERSTAND AND USE INTRINSIC MOTIVATORS – a company hitting the market with lots of buzz and activity does not necessarily mean there is a product/market fit. In fact, initial buzz and growth may be coming from extrinsic motivators (the ever-popular ‘gamification’ of today – as Kathy Sierra calls it “the high fructose corn syrup of engagement”). Motivators like badges and coupons and deals are temporary solutions and actually lead to demotivating your customer base as they diminish in value. Instead, think INTRINSIC motivations such as Challenge, Curiosity, Control and Competition. Motivation has loads of research on it now (I’m currently reading Dan Pink’s DRIVE, which summarizes much of the research). The key here is to match the RIGHT intrinsic motivators to your market.

Doing all of the above will not guarantee product/market fit. You still have to experiment and be agile…and be willing to persevere through until you nail it. The issue may be as simple as timing…or technology…or messaging…or being in the right place at the right time. But you increase your chances of hitting the sweet spot by being out there and agile.

The only guarantee of ‘winning’ is to find that product/market fit before you run out of money…or even after you run out of money to find a way to keep tweaking it. We’re still working on it ourselves and I’ll let you know the moment we nail it.

Welcome to one of my regularly scheduled attacks of futility. It happens about once a month if I’m lucky and once per week if it’s a really hard month. It starts with something small that triggers it. A comment from someone. A post. An announcement. The post or announcement usually surrounds some frothy statement like, “Look at all of the money being thrown around! Wa-hoo!” or something not quite as hyperbole, but points to the same thing. I read the headline and then look at my own experience and think:

“Geez. I must be doing something incredibly wrong if it is this easy to raise money and I’m not. I suck.”

This thought has a tendency to spiral into, “What business do *I* have being a CEO? I’m terrible at this!” Eventually, though, I kick myself out of my pity party and get creative and work harder. To date, I’ve pulled through each and every attack with new ideas and a renewed sense of purpose.

I just gave a talk on being a startup entrepreneur in the midst of looking for funding at NXNE Interactive called, “So you wanna do a startup, eh?” The gist of it is that all of this frothiness isn’t so good for startups that want to build something that means a damn. The advice is awful. The frenzy makes for poor short-term thinking. And the urgency caused by all of it means that everyone is making bad decisions based on no evidence. VCs/Angels are following the herd when most of them are smart men and women who didn’t get to where they are because of herd mentality. Entrepreneurs are pivoting away from the ideas that put them on their path in the first place and following trends that don’t really mean a damn (gamification or daily deals anyone?)

If we ARE in a bubble, and many people think we are, then the cash grab myopic activities will merely accelerate the bursting of that bubble. And sure, there are people who make money during these frenzies, but it’s a small number and you probably aren’t one of them. You’d need lower scruples.

But I think the biggest travesty of this time period is ideas. As Mark Suster said in his awesome presentation (which was misinterpreted by TechCrunch as a cash-grab statement), “Some good companies simply don’t get funded.” Those companies are usually the trailblazers. Think Pandora. Think AirBnB. Think Zappos (who struggled with funding during the first bubble). Think just about every startup who didn’t follow the pack.

Ideas are crazy hard to bank on. They are crystal clear for the idea-thinker, but are incredibly difficult to gr0k for the idea-listener. An idea doesn’t come out of a single eureka moment. It comes out of years of thinking about a problem and having small bursts of inspiration here and there pummel your brain until you are able to piece them together one day into a cogent thought. Without taking the listener on that long journey, he/she won’t be able to understand how x solves y.

Take AirBnB for instance. The founders had a need: paying their rent. There was a conference coming up that created an opportunity: people looking for cheap places to stay. They pulled ideas from their own experiences: sleeping on an air mattress is a good, inexpensive way to travel and couchsurfing has made it safer to open up one’s home to strangers. They added a sparkle of business acumen to solve their original problem and address the opportunity: what if we charged a nominal fee for conference goers to sleep in our apartment on air mattresses? And then, when the experiment was a success, they had their big idea: let’s create a tool to match people like us with travelers? Brilliant, right? Well, we know that now, but not many people thought so. In fact, they were practically laughed out of VC and Angel offices when they pitched the idea. They understood the brilliance of the idea because they lived it and experienced it unfolding. But it was a radical way to approach things and not so easy to wrap a brain around by someone who had never been there.

So instead of wacky new ideas like this getting funded, ideas that look like other ideas get funded quickly. Of course, once the model is demonstrated/proven, it makes it much easier to gr0k. That’s why the ‘high level pitch’ is so popular. “We are Mint.com for Products.” “We are Foursquare for relationships.” Etc. It’s essentially:

“We are -insert company that is wildly popular here so there is no question as to the business model- for -insert slight variation of market/product/vertical-.”

But the issue here is that we start to see a market glut of products that are x for y instead of thinking about creating products and services that actually mean a damn. Not saying that x for y doesn’t ever mean a damn, but by and large it becomes a bit of a cash grab. Just add the frothy money slinging market we are seeing right now and it gets even worse.

Bring on the feelings of futility.

Why would anyone want to enter a frothy market that has an idea that comes from a real place of “let’s make stuff work better for people AND make money?” It’s heartbreaking. And no, I don’t want to pivot and grab onto cash cows. It’s distracting and dishonest and will lead to another crash. And that isn’t good for anyone.

That’s why I find it necessary to keep talking frankly about reality. It’s probably not popular or doing me any favors in my journey to raise money to fund Buyosphere‘s ability to build something that helps make stuff (in this case, commerce) better for people (and make money). But I’d really like to open up the conversation on how we can take a step back from the frothy frenziness of today’s startups and talk about real solutions for real entrepreneurs with real passion for their ideas who want to serve real people’s needs.

I’ve embedded my deck below. I’d love your feedback and your own stories. I’d like fewer journeys into the pits of futility and more into conversations about solutions.

Photo taken by Carlos Pacheco (aka. the very patient man who keeps me strong through this) while we were out looking for a good coffee at NXNE Interactive.

I am in love with Sheryl Sandberg.

Not a romantic love (though she is pretty attractive as well as inspirational), but the female equivalent of Man Crush (is there a name for this?). I gobble up any videos of her on the web. I read and highlight every second quote by her. I find myself dreaming about meeting her someday and giving her a big hug and gushing about how grateful I am that she is in the world and how incredibly brave she is for speaking up from her position.

She is a woman who has ‘made it’ who isn’t afraid to say that it was a struggle to get there. She’s honest enough to talk about the times when people tried damaging her reputation, targeting her in large because she is a woman:

Do I believe I was judged more harshly because of my double-Xs? Yes. Do I think this will happen to me again in my career? Sure. I told myself that next time I’m not going to let it bother me, I won’t cry. I’m not sure that’s true. But I know I’ll get through it. I know that the truth comes out in the end, and I know how to keep my head down and just keep working. READ MORE

The comments on the article are telling of the underlying biases and attitudes that hold back women. And the same arguments against Sheryl’s honest telling of her trail to success are railed against many other women who are telling the story as it happens: “You are imagining things.” “Stop blaming everyone else for your failures.”

In fact, I watched a kickass woman I admire (and ALSO have a girl-equivalent Man Crush on), Sarah Prevette, experience the same type of comments after being featured in the Globe & Mail by Amber MacArthur. One commenter called Sarah a woman “looking for excuses.” Is this the same Sarah Prevette I know who is the LAST person on the planet who looks for excuses?

I know the struggles. I feel them. I started a Google Group to discuss how we can combat the subtle sexism that Sarah talks about because I’ve had the same conversation with every kickass woman CEO, founder, executive and entrepreneur I know. It goes like, “They don’t say it, but I *know* they treat me differently. They aren’t taking me seriously because I don’t act like a man and when I act like a man, they call me difficult.”

How many VC meetings have I been in where the VC turns to me and says, “Yeah. I just don’t get it. Maybe I’ll show it to my wife.” BURN! Really? Would he say that to a man pitching him the same concept?

Hell, even the VCs (or angel Paige Craig in this case) are talking about how the subtle sexism works and getting shut down. And I look at the companies getting funded…UBER funded…versus those NOT getting funded (or those getting underfunded) and I see lots of women in the underfunding/non-funded category while the same damned ideas are getting money thrown at them when they are led by men.

I had a candid conversation with a prominent tech reporter who told me s/he pitched an undercover story on exposing the VC bias toward young male founders (planting the same idea with a different gendered CEO in front of the same VC firms) who was told it would never happen because it would be too scandalous and the media company would get blacklisted.

But I get the messages from people saying, “Stop talking about this stuff. You’ll only get blacklisted yourself.” and I think about Gaslight, the 1944 Classic Movie with Ingrid Bergman (one of my faves of all time). From the description:

Years after her aunt was murdered in her home, a young woman moves back into the house with her new husband. However, he has a secret which he will do anything to protect, even if that means driving his wife insane.

It’s an amazing metaphor for how many women in technology are feeling today. We are sure we see the signs that discrimination still exists, but then they are explained away or we are told “you are being crazy/blaming/whiny/etc.” and we start believing that we must be imagining it. It doesn’t stop us from moving forward, but it takes its toll emotionally and physically. It wreaks havoc on the personal lives that help re-vitalize us. It isolates us. It pits women against one another. Soon we believe our own insanity.

The problem is that it isn’t obvious. It’s, as Sarah pointed out, SUBTLE. There isn’t a glowing example to point at and say, “See? Look at that? I was right!” It happens in whispers. In comments. In unchecked biases. In rules that favor certain types. It displays itself in absence.

I don’t know how to name it, fight it, overcome it or even really expose it. But like Sheryl, the best I (or any other woman I know) can do is to keep our heads down and work hard and push through it so more of us get into power positions like Sheryl and even out the deck. On the way we are going to think we’re crazy and feel isolated and understand we need to work 5x harder to prove that we are worthy of our successes. We need to toot our own horns and ignore those who call us ‘self-promoters’ (I’ve heard this insult countless times). We need to seek out amazing men who get it and who will help us through their power to get there. We need to stop apologizing, using passive language (I do this too much) and just say, “I know what I’m doing. I’m awesome.” We need to come together and support one another – name it, but then change it.

Thank you, Sheryl. Thank you, Sarah. Thank you, Nilofer. Thank you, Cindy. Thank you every single woman who is on the Google Group, who has stood up, who continues to fight and who is paving the way. I’m in love with all of you.
___________________

Cool! My post has been picked up by:

• Ben Rooney at WSJ – The Subtle Sexism in the Tech Industry
• Alyson Shontell at Business Insider – Hey VC’s! Stop Saying This to Female Entrepreneurs!
• Rachel Sklar at Change The Ratio

There are multiple schools of thought on raising money. And no, I’m no authority on it (as I am still yet to be successful), but I have spoken with many startup founders and observed many others. But the two major ends of the spectrum of raising early money is:

• Raise the basics of what you need to get to your next goal (usually 12-18 months)
• Raise as much as you bloody well can

After witnessing some extreme examples of the latter (Color and Blippy are two that come to mind) get hyped and then fizzle, while watching companies like AirBnB and Sonar get really creative with smaller amounts, I have a tendancy to favor leaning more towards the former.

There really is not a rule to anything — and I’m not a fan of that type of thinking — but I heard a story the other day that made me pause and wonder how much it applies to startups. Basically, it goes like this:

A guru gives a young boy a butterfly forming in a cocoon and tells him not to help it, no matter how much he wants to but the boy does it anyway and the butterfly dies. The guru tells the boy:

“You don’t understand. You didn’t understand what you were doing. When the butterfly comes out of the cocoon, the only way he can strengthen it’s wings is by beating them against the cocoon. It beats against the cocoon so it’s muscles will grow strong. When you helped it, you prevented it from developing the muscles it would need to survive.”

It may or may not be a true story, but I like the sentiment. With every struggle we’ve been through, with every set back and with every challenge I am learning something about myself, building a business and I am growing. I’ve made mistakes, but learnt to fail fast, learn and move forward. I’ve learned to be agile and to ask for direction. I’ve sought out mentors to guide me. I’ve learned that I am stronger than I thought I was. I’ve learned what I didn’t think I’d ever need to learn. I’ve discovered I can sacrifice and the depths of my commitment to Buyosphere and my team.

And, sure, I may be justifying all of my struggle to make myself feel better, but I truly believe this is all part of the startup story. I fell in love with AirBnB because of theirs (the campaign cereal). And as I feel like I’m getting closer to the ability to hit the road running, I’ve learned some fundamental lessons on how to run so that we run faster, smarter and more efficiently. In the shadow of the Goliath funding round we just found out a potential competitor (that came out of nowhere) raised, I feel our team is well-equipped to face the future battle.

None of this would have been possible if someone dumped a boatload of money on us from the beginning. And when we finally do raise the money we’ve been looking for (which is enough for the next 12-18 months), I’ll really appreciate it.

My muscles are strong. It’s time to fly.

Four and a half years ago, I started talking about how the currency in online communities is social capital…or Whuffie…and subsequently wrote a book on the subject. I had gained enough social capital in the online community space to be blessed by a book publisher to write a book as a thought leader on the subject. I didn’t even need to knock on any doors.

The social capital I gained that gave me leverage was, largely, through connections. Sure, I knew what I was talking about. I was living it. Studying it. Creating it. I was fairly knowledgeable on the subject (although the subject was -and still is- still a fuzzy area, so nobody can really gain expertise in it). But the biggest reason I gained enough leverage to get a book deal was because of my connections. I could get quotes from Michael Arrington, Jimmy Wales, Biz Stone and other movers/shakers in the biz. Others blogged about my posts or sent them around to others (through my stats, I could see more of my posts were being passed around by email than any other method – and usually within organizations).

And, yes, I worked hard. And, yes, I was early enough to stand out. And all of that. But I’d say I had unique access to networks because:

• I’m a white, middle-class, educated woman
• I’m attractive
• I had a whole lot of years of opened doors behind me that came from me being the above

So when I read Jon Bischke’s post “What Really keeps Poor People Poor” I cheered out loud for his cogent statements like:

“(P)eople from lower-income families aren’t able to gain access to the same networks that higher-income families have access to.”

and

“Poverty is not deprivation. It is isolation.”

I feel like I’m living proof of the advantage of the power of networks on my income every single day. I was raised in a small town in Alberta. I had never heard of the Venture Capital world. Who knew there was a rather large group of people who gave money to another group of people in exchange for a company that is worth nothing (but may be worth something someday)?

I discovered this world in the early 00′s and was fascinated by it. Now I’m in the midst of raising money for my own company in this manner. My company will be valued at a guestimated amount of money based on a guestimated future marketplace. It’s pretty wild if you ask me. Of course, this happens because those guestimated numbers and future marketplaces actually pay off…and sometimes in bigger numbers than dreamt up. So it’s worth the gamble for the investors.

But the part of this whole world that really baffles me is the access part of it. Certain people have access and certain people don’t. Not that there is some bouncer at the door that stops one group of people and allows another, but knowing someone means the difference between getting a meeting and not getting a meeting. And then there is a difference between how that meeting goes depending on the type of introduction.

Introduced by a friend of an angel/VC? Pretty good. May be more patient with you and give you good feedback. Not a slam dunk, though. Introduced by a portfolio company CEO? Pretty good. Not a slam dunk. Introduced by a portfolio company CEO with a good exit? Awesome. Depending on the level of enthusiasm from the CEO (better yet, why not bring them along), could be a HUGE slam dunk. Introduced by another angel/VC? Awesome. But only if that angel/VC says they are wanting to invest. Then it’s pretty much a slam dunk. If it’s a ‘pass off’ (“I met with them and am not investing, but you may want to”), it is not.

Y-Combinator is a slam dunk because of Paul Graham and his connections. Accelerators have been around for ages. This one is special because of the man behind it. Because of his connections. The reason why the value of many other accelerators is questionnable is because they don’t have the same prestige. And that prestige has everything to do with social capital.

Why do people go to conferences? The connections. Why do people go to university/college? The connections. Sure, you can learn stuff and grow your talent, but as Bischke’s article states, you can get access to all sorts of knowledge, talks, lectures and resources online, too. It’s not the content, it’s the connections. And when the barrier to entry is high (Conferences like TED or The Lobby – schools like Harvard), it’s a signal that you now have access to those connections, too.

Over and over again, I’m observing how valuable connections are. Social classes aren’t dead by any means. If anything, they’ve become more powerful than ever. In a world that is incredibly connected and competitive, it’s getting more and more important to separate the signals from the noise and social class is an easy way to validate a strong signal.

For the record, I’m not endorsing this. I’m merely observing it. I’ve been told repeatedly that the web creates meritocracies, but from personal experience, I’ve seen that the world that controls the web also reinforces social hierarchies. It’s a bit confusing. Doors are opening, but getting through them is easier for some than others. Knowing this makes it easier to break into ‘the club’. Unfortunately, entry to the club is easier for some than others.

You can have the world’s coolest idea, be amazingly smart and have executed perfectly, but without that ‘social proof’ (ex-Googler, former exit, introduced by the right people, etc.), you will have a tougher time getting through the noise. I sometimes wonder how many companies have failed because they ran out of money before they could get through the ranks. I’ve heard stories first hand. There are probably many more.

Hopefully programs like Angela Benton, Wayne Sutton and Toby Morning’s NewMeAccelerator will go a long way towards creating connections for those previously on the outside. And personally, I’d love to answer Bischke’s call for increasing access to networks for those on the outside. As I work my way inside, I’ll continue to share my own experience with access, then when I exit and set up my own venture firm someday, I’ll focus on finding, meeting with, working with an mentoring those with great ideas.

So I was sitting on my sofa having my nails done on a Sunday night after a lovely day filled with Spa, light shopping, stopping for an ice cream treat, going for a nice run and generally enjoying the day and I stopped and thought to myself, “Hey. Wait a minute. What’s wrong with this picture?”

Well, what was wrong with this perfect picture is that I was spending this amazing Sunday with someone I call my boyfriend. And, according to me not too terribly long ago, that was NOT going to happen.

It turns out that, with the right partner, love and greatness are not mutually exclusive. They can exist together! I’m cautious to claim that my experiment has been proven and is completely conclusive as I have yet to achieve much in the department of greatness and the love I’m enjoying is pretty new (only a couple of months in), but I thought I’d share some observations on what kinds of conditions need to exist to make this happen.

Condition #1: Listen to The Force

The Force is an incredibly geeky way to say that there is something completely uncontrollable about this. It’s that moment that cannot be forced when you meet that person and think to yourself, “Holy crap. I just saw a flash of us growing old together.” And the worst part of The Force is that it’s usually what happens to the man, not the woman. We (as women) are too busy reading dating advice columns and making lists of what we need in a man, then going on dates and assessing whether or not this specimen fits that list. But that’s okay. That’s what we do (or at least most of us). Women are by-and-large rational daters. I know it seems counter-intuitive, but we are. That’s why this quote from My Blue Valentine really struck a chord with me:

I feel like men are more romantic than women. When we get married we marry, like, one girl, ‘cause we’re resistant the whole way until we meet one girl and we think I’d be an idiot if I didn’t marry this girl she’s so great. But it seems like girls get to a place where they just kinda pick the best option… ‘Oh he’s got a good job.’ I mean they spend their whole life looking for Prince Charming and then they marry the guy who’s got a good job and is gonna stick around.

It’s kind of true. Carlos ‘knew’ minutes into our first date and he was going to fight to make me ‘know’ in spite of my protests of being “too busy for a relationship.” And he fought in the most gallant, amazing ways that really took me by surprise and made me think, “OMG. This man is crazy and awesome and makes me feel loved like I’ve never felt before. And in every other relationship I’ve been in, that has been what I cried about. How can I pass him by?” He made me want to fight for him, too.

It can’t be just something. It’s gotta be THAT ONE THING. Your life is big, girlfriend. Your love should be, too.

Condition #2: This is a Drama Free Zone

Yes. Yes. Love and relationships are all about compromise, right? Sure…when it comes to planning activities and sides of the bed. But too many compromises means that there is a blatant mis-match. And if there are compromises to your life’s dream and work, this won’t work.

Love and greatness only works together if it works together. If the love is full of drama and fighting and resentment and giving up time doing what you love to do, then it will rip you apart, cause you stress and leave you with nothing in the end.

Funny thing is, I find myself working more efficiently these days because I want to have time to cuddle up and watch a movie later on instead of working until 2am. The other advantage to meeting someone in our late 30′s is that we already have lives established before one another. Both of us have plenty of things we do independently. He has a career and buddies and activities he enjoys doing. And when we can, we invite one another cause we like being together. But there isn’t pressure to spend a certain amount of time together. Just quality time when we do.

No drama. No resentment. It’s all about supporting roles.

Condition #3: Learn to Receive

As a woman conditioned to never need anyone, this has been the hardest thing for me to get used to. Carlos is a giver. He thinks about how he can make me happy all day long. Really. I know. This is awesome, right? Only thing is it felt like an embarrassment of riches when I first started experiencing it. I didn’t know what to do with any of it. I told him to stop because I didn’t have the time or energy to give back. But he told me he didn’t care. It makes him happy to make me happy.

Why the heck was this so hard for me?

Then I decided to just let go and accept it. Accept the attention, the generosity, the amazing little things he did: creating mini-adventures, leaving notes for me to find, setting up private tumblr accounts to record ‘our private thoughts to one another’, buying stuff he’d see me post on Buyosphere as WANT!s, and continuing to formally ask me out on dates…and guess what? I started to freakin LOVE it. I became that princess I was always told I shouldn’t expect to be. And, dammit, I was ripped off before! This feels great. I used to be the one who came up with the cute ways to say “I love you”. Now someone else thinks of it for ME. And because I know how to give it back, when I have the chance, I give it back.

I’ve seen this part trip up loads of ambitious women. They’ll reject all of the men who come along and want to pamper them because they’ve been so conditioned to believe they need nobody that they can no longer accept someone who wants to make their days brighter and easier. Egad, I have someone who wants to pick me up at the airport and offers to do my errands. I needed that. And I’m not afraid to admit it.

Condition #4: Pay Attention to the Little Things

As listed in the previous condition, Carlos is the master of the gesture…big and small. And I hate to admit it, but it’s the small gestures that get me the most. The other day I was rifling through my wallet for a receipt and I found a note that told me I rock his world. It was just a small handwritten scrap ripped out of a notebook, but it made me smile bigger than I’ve ever smiled before.

I’m busy. He’s busy. Changing the world is a big time-suck. So those little gestures are perfect morsels of happy to infuse the middle of my day. They don’t take an hour of my attention and right after I enjoy the burst of joy I get from something like a note or a text message, I can re-focus on my task at hand. Even better, that little reminder that I’m adored improves my overall mood and ability to handle the road ahead.

It doesn’t have to be all big displays and full attention grabbing gestures. Those small bits are perfect bite-sized breaks that keep the stress levels low.

Condition #5: His High Conscientiousness Levels

I never thought that I would find stability SO attractive in a man. I thought I was looking for an artist or another entrepreneur…someone who faced the world with the same careless abandon that I do. Then I met Carlos and fell in love with the fact that he has an amazingly high level of conscientiousness.

Not that it’s impossible but dating fellow entrepreneurs, dreamers, artists and other equally unstable, but exciting guys, will rarely fulfill the previous 4 conditions. Their FORCE is focused on changing the world, with unstable usually comes HEAPS of drama (anxiety, depression, moodiness, aspergers, etc), no time to give or think of how to make me happy through amazing little gestures (“Hey, I have a world that needs me and you are whining about not being asked out on a date? Selfish!”).

Having one partner who is focused on making the relationship and home life exciting is essential. He needs to be conscientious. Almost like a…um…wife. I know that sounds sexist, but the metaphor is still unfortunately recognizable.

And this doesn’t mean that Carlos or any other guy that is highly conscientious is a passive weenie. Not in the least. I find doormats unattractive. That man still needs to have all of those basic qualities – strong, smart, funny, attractive, fun, fit, healthy, sexy, cultured, reliable, interesting, stylish, etc. – that are part of my ‘list’ in order to be such a big part of my life.

And yes, I know what you are thinking: That is a TALL ORDER! A freakin impossible list of conditions ON TOP of our previously freakin impossible list of qualities! There is no WAY on earth that I’ll ever find someone!

Well, I did and that is a bloody miracle. And if I can, you can.

And, for the love of god, don’t settle for less because without all of the above, love and greatness will have a tough time co-existing. Without #1, love won’t happen at all (and I know you can’t control it. Deal with it). Without #2, you’ll exhaust yourself emotionally. Without #3, you’ll lose the romance (I’ve been in that relationship and it’s heartbreaking). Without #4, you’ll feel resentment. And without #5, you’ll never see one another anyway.

Now…I need to take these same principles and adjust them for raising money…or buy a lottery ticket, because I’m feeling quite lucky!