horsepigcow

Specific design decisions are important to achieve specific outcomes. The one that iss most poignant to me is the decision to build quantity or quality content.

If you want big numbers and lots of content, make it super simple to join/post/etc. “Of course we want big numbers, Tara!” you are thinking. But it’s not entirely desireable. The downside to simple signup/posting/etc is that it attracts low-brow content. Sure, there are lots of users, but the content can become terribly uninteresting and sometimes spammy.

If you want quality content and users, you make sign up a little more arduous and content a little harder to post. Not impossible or even difficult, but your design requires the user to sign up with a little more information and posts to require a little more thought.

But it seems that today, all people seem to care about is quantity. Big numbers. Fast. This leads to ‘hyped up startups of the week’ where everyone talks about how freakin awesome and huge a startup is for 2 seconds, then moves onto the next one and rarely (if ever) discusses that startup again. When the in crowd moves on, all that’s left is drivel content. That’s not a sustainable business or something that I ever want to build (but it seems to be what any angels or vcs want us to build).

“Allow anonymous posting!”
“Take out steps to adding content!”
“RE-tweet/share/post/tumble/pin/poke/blah!”

I think there is a happy balance of creating an app where there is an ease of use and quick posting while requiring real people that have something significant to say to have a voice.

Facebook used to be that place. You needed to sign up with your real name. If you were going to post, you’d have to come up with something fairly original and semi-interesting to say before you hit post. Not all content was interesting to everyone. But it was original and it said something about the person posting it. There were rants, personal photos, bad days, breakups, new relationships, inspirations, arguments, embarrassing drunken confessions, more embarrassing tagged photos of others in compromising moments, commentary, food porn….the list goes on and on and on. Whether or not you found something interesting in your feed was completely subjective. I, for one, love the mundane. I’m deeply interested in the bits and bobs of people’s lives.

And that content still exists, but it is starting to give way to something else: RE-posting.

The other day I thought to myself, “Egad, Facebook has turned into Tumblr!” I think Tumblr is lovely. It’s easy to use and well-designed, but I find the content on Tumblr shite. It seems to be all about following as many people as you can, then finding the best, most inspiring, funniest, prettiest, craziest stuff and hitting a little button to post it to your own Tumblr. It’s the image equivalent to retweeting and I wouldn’t mind it so much, but it creates a whole lot of noise without any originality.

Take, for instance, the screenshot I took today. Yes. I think the post is interesting and very poignant…the first time I see it. And I may even appreciate how others share it because it shows me who is aligned with this line of thought in my stream. But after 20+ shares (or REposts), I start to roll my eyes. And believe me, I’m JUST as guilty of this as anyone here. It’s a rush to REpost something poignant and have a whole bunch of people REpost it from you. “Look at all the people I influenced! I’m special!” But I’m not. I was most likely the 2,345,896th person to REpost this on Facebook. I just happened to get a jump on a few dozen others.

I hate to wax poetically about the good ole days (though I have been more and more lately), but back when I started blogging, people became popular by producing amazing original content and thoughts. And if you were going to discuss someone else’s idea, you would ADD to the conversation by coming up with some of your own thoughts and then link back to the original blogger’s post. And we got smarter and were made to think about why something resonated with us and how we could improve on the original rather than just add noise.

Maybe there is no such thing as original thought anymore? Or maybe we’ve just got too busy to form our own ideas and articulate them. Or maybe it’s just unpopular to do so. Who knows. But when every platform becomes a REposting platform, I start to get really bored of the “social web” and long for a small community of original thinkers who don’t care about popularity or REposts, but instead care about learning and growing and making something worth archiving.

Tumblr is great and it exists to REpost stuff ad nauseum and somehow it works for the communities it serves. Google+ attempted to do it, too (but when you start with poor content, the hype wears off fast – lesson?). If Facebook wants to go in that direction, then I’m worried about its future. Maybe we’ll go back to blogging. Maybe something else will come along to fill that void.

But popular or not, I’m going to continue to try to produce content that isn’t about hype and is about adding to the conversation instead of just adding noise. At least as much as I can.

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…

On day 1 of the Google+ launch, I joined as I was invited by a bunch of friends. I was pretty busy on that particular day and saw everyone buzzing about it, but didn’t have time to spend more than about 10 minutes setting things up.

The first thing that bothered me about joining was that it forced me to use my old gmail address that I retired because it was taken over by mailing lists and social network pings. Rather than just proclaiming email bankruptcy…even that would have been too much work…I just put a permanent out of office greeting on it that says, “I’ve laid this email address to rest. If you are a human being, email me over there instead”. Over ‘there’ is my Buyosphere email address. We use Google Apps, etc. to host it, but Google limits these PAID FOR accounts to anything social because…um…I think corporate stuff is supposed to be anti-social. Either way, I had to log into my festering gmail account to make the G+ leap.

I have to say…the interface is nice and clean and the javascript is way nifty. It was fun adding a few folks to circles for that 10 minutes. Their little round avatars looked like smiling bullets in a chamber. Zip! Zip! In all seriousness, though, the UI is awesome.

But then I went away and did some work type of stuff and kept getting messages that 18 people added me to circles here and 26 people added me to circles there. Next thing I know, I log back in a few days later and I have a mile-long suggested list of friends to put into circles. 2,500+ of them! Now, I’ve met most people who are suggested. I’ve had conversations and hung out with many of them. I would even consider most friends. But to put 2,500 of them in intelligible circles?! I have no clue where to begin!

I started with cities: Montreal, New York, San Francisco, Austin, Paris, Los Angeles, Vancouver, Sydney….then I started to get a little fuzzy on where some of my contacts live. Many of them I’ve met at conferences and hung out in places neither of us live. It’s quite difficult to keep track of the home addresses of 2,500+ people at the end of the day.

Okay…so I moved onto topics: technology, entrepreneurship, karaoke, fashion, social media…once again I hit a wall. I know people from certain conversations that probably have little or nothing to do with the topics they cover day to day. In fact, those that are Facebook friends talk about great personal stuff like families and their favorite restaurants. I actually enjoy getting to know them on that level.

Right. So default back into Friend/Acquaintance/Follow…but those are pretty broad categories. And I don’t know about you, but social networking has changed my definition of friend. I know more about many of my FB/Twitter “friends” than I do some people I grew up with!

And then I started getting a little fuzzy on why I was putting people in these circles anyway. I have no idea how I want to filter thoughts or feeds. The ‘sparks’ feature (where you can follow topics) is much easier for me to gr0k. If only I could mash the two up a bit. Or something. Something bigger. Better.

Oh wait.

YEAH! Google has all this information about me, right? They have been collecting it for EONS. They collect it when I search, when I email people, when I create documents, make meetings, shop on Google Products, use my mobile phone, etc. etc. They serve up incredibly relevant ads for me daily in all of my Google-y type applications. Sometimes so relevant I get a little scared. They seem to know my next move before I do. Google tells me who to add to cc’s on emails. They understand who are in my groups I’ve moderated for years and know what we talk about. You told me through Latitude that you know where I work versus where I live based on the hours I spend in these places. Google knows more about me than I know about me.

SO WHY THE FRACK CAN’T THEY MAKE MY CIRCLES FOR ME?!!

Sorry G+, but adding 2,500+ people to cute little circles when you have more data than GOD seems wrong to me. At least give it a whirl. Take a shot in the dark on who should go where. You could DEFINITELY figure out city for me…see that I’m creating City named circles and say, “Hey! I see you are putting your friends into locations! Let me help you with that!” Suggest topic circles based on people’s sparks. Or their descriptions. Or what other people group them as. You should definitely know who I work with. You probably can infer what a personal versus professional email sounds like.

I know people will be a little freaked out…but that is what makes for magical technology. And you have it. You have miles and miles worth of humming data farms worth of it. Stop holding out and making me feel like a GoogleMinus. Don’t make me work for another social network. Make your social network work for me.

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.

Just recently, I was tasked with finding women to attend a prestigious event that would put them on a deep social level with venture capitalists, angels and fellow startup entrepreneurs. As I pay close attention to the presence of other women in my field (startup founders), I felt this would be a simple task. It is not.

The issue is as follows: the core limitation of the invitation is that the startup founder cannot also be working as a consultant. That person has to be ‘all in’ (as I discussed in my TEDx talk recently, doing your startup alongside consulting/working means you aren’t all in). Because of the lack of funding/underfunding for women-led startups, many female startup founders have had to resort to doing some bitwork on the side. I know from personal experience (not yet getting any funding save bits and pieces of F&F money), I’ve been tempted to do some consulting in order to pay my bills. I’ve only refrained because of time issues. I’m still broke.

The second part of the issue is: though this event is reasonable as compared to events like TED, Davos and The Summit Series, it still costs more than $1,000, which, for anyone who is bootstrapped, is not only tough to swing, but pretty much impossible.

And the ultimate issue is: this becomes a chicken or the egg scenario where an unfunded entrepreneur needs to create those social bonds with people in positions of power and wealth in order to get funded, but because she doesn’t have the funding, she cannot actually attend.

I did something pretty cool a couple of weeks ago. I went running with Rob Hayes, a partner at First Round Capital. We met for about an hour, then we put on our sneakers and went for a 45 minute run. I already knew that First Round had a conflict and couldn’t fund us, but it didn’t hurt to bond anyway. Rob thought it was an interesting way to get his attention and commented, “I think people should conduct all pitches this way.” We ended up talking about everything but my startup and, at the end, he made oodles of valuable introductions for me. It’s a meeting I’ll never forget and probably one he won’t either.

This is sort of akin to the idea that the deals take place on the golf course. It’s true. Social connections and feelings of camaraderie will give anyone the leg up to getting funding and making deals. This is why the ‘old boys networks’ are so powerful. Those relationships are the key to making things happen. And herein lies the rub.

People love to hate on Affirmative Action: the policies that are meant to give equal opportunity to minorities by setting a minimum hiring threshold for women, people of color and otherwise non-Caucasian able-bodied males. I won’t go into a debate about this as there are, of course, issues with the implementation of such policies, but I will say that a ‘leg up’ is something that comes quite naturally to certain groups: ones that can afford to socialize with those with money and the power to help.

No, I don’t want to be funded because I have boobs. But sometimes I feel like I’m NOT being funded because I have boobs. As I’ve been at this for a while now (things haven’t changed since I gave that TEDx talk), I’ve observed patterns emerging in the barriers to raising money:

• I’ve heard repeatedly, “This is not a market that I’m familiar with and I’m not comfortable investing where I don’t understand the market,” in response to the fact that Buyosphere’s main audience is women who make the majority of the household purchases.
• The second most heard excuse, “We have a conflict,” which roughly translates to “I don’t understand the market and the future of this market and get that there are multiple ways to approach the democratization of commerce, and haven’t figured out that I need to diversify my portfolio in this area.”
• The third reason for passing, “We have too many deals going on right now,” which is true. There is a frenzy of investing happening at the moment. Apparently in men (according to the WSJ as well as talking to other women like me who are struggling). I’d kill to be a teensy part of that frenzy. We’re looking for a much smaller number than is being thrown around in these deals.

I have a private Google Group for female entrepreneurs where we discuss these issues. There are about 100 members. We try to keep it strategic so as not to get bogged down in the frustration, but it’s not easy when we hear news day after day of this company raising multiple millions off of a pitch deck and that company raising millions within weeks of coming up with an idea with no clear revenue model after most of us have launched, have users, have a revenue model and long-term visions that appeal to THE BIGGEST MARKET online: women.

And it’s not that anyone is overtly sexist or trying to block us from advancing. It’s not malicious at all. It’s just that those with the money don’t understand our markets. I can share the charts and statistics and big, fantastic numbers showing the growth and the potential, but it doesn’t really register. They don’t understand the phenomenon behind Haul Vlogging and Makeup Tutorial obsessions (yes, that does say over 27 Million views). They certainly don’t understand Swishing. And yes, there are women in VC roles, but not very many. They are also highly in demand and we cannot paint them all with a ‘you’re a woman, so you’ll get it’ brush. Quite often they’ve survived tech finance because they can think like a dude.

Running with Rob didn’t cost me anything, so I was quite proud of my creativity in that one. But there are oodles of events that are going on that are enabling the bonds between the money people and budding entrepreneurs that DO cost money. And the fact that I’m having a helluva time finding women who can afford to attend just one event (one that is pretty damned cool if you ask me) is a bit troublesome. And Women 2.0 and Women in Tech events are awesome, but don’t quite bring the same advantage as mixed prestigious events. Perhaps an effort to get more women to these events (scholarships? comped first time passes? just freakin funding us and making the effort to learn more about our market?) would help increase the rate of women attending and break the cycle of the same types of people getting funded and encourage more activity from female entrepreneurs.

Like I said, I don’t want to be funded because I have boobs, but I also don’t want to run into barriers because I have boobs. Speaking of which, I have to figure out some new ways to bond with the movers and shakers. Anyone into mani/pedis?

“I’ll tell you everything, and you tell me everything, and maybe we can get through all the piss and shit and lies that kill other people.”

~ Claudia Wilson Gator in Magnolia (1999)

This is one of my favourite movie quotes of all time. I remember watching this scene over and over again. Claudia was a complete mess. Actually, all of the characters in this movie were. But she was the most honest character about her messiness. She was willing to splatter her messiness all over the place just to get to a real conversation that may lead to a real connection.

Just over a week ago, I posted my own splattered messiness all over the internet in the form of a TEDx talk. When I gave that talk in February, it took everything I had to hold it together on the stage. When I wrote the script for that talk, I was bawling like a baby. It wasn’t manufactured or hyperbolized. In fact, I edited the final talk quite a bit to remove the bits that were sure to make me lose my shit on the stage.

I was scared to give it. I’m still scared every time I send it to someone. I’m not talking about my success or all of the awesome things I’ve accomplished in that talk. I’m talking about struggling, failing, not knowing where I’m going, being delusional, stumbling, breaking down and generally being a mess. Sure, I give a little upbeat Apple Ad bit at the end of the talk so I can end it on a hopeful note. It’s the same upbeat talk I give myself at the end of every single day.

But like Claudia, I just want to get to a real conversation that could, hopefully, lead to some very real connections at the end of the day.

And connect I have. I’ve received close to one hundred emails from people – mostly strangers – who thank me for giving that talk. They thank me because they are either experiencing the same struggles or they have experienced those struggles in the past. And in most of their recollections, nobody else came forward and told them they were in good company.

Instead what DO we hear? We hear about multi-million dollar valuations, twenty-something overnight billionaires, napkin sketches that get millions in funding, gabillions of downloads overnight and that crazy idea that went from zero to turning down a multi-billion dollar acquisition within a year. That’s a whole lot of millions, gabillions and billions to take in when you are sweating over whether you are going to make your payroll at the end of the month. It’s enough to make you think you just may be chasing a pipe dream after all.

Here is my counter-intuitive thought: the constant proliferation of success stories is actually discouraging to the right kinds of entrepreneurs that could be fixing a good amount of the world’s problems.

The majority of the email I’ve received is from women. Yes, it’s probably because I *am* a woman and they could identify, but it’s also more likely that they think if they talk about their struggles, they will show that they are weak and can’t hold up to the brazen entrepreneurship of the winning men. The truth is that everybody crumbles. Even men. Those stories just don’t make the covers of Fast Company. They silently slip away. Or they are told POST-success: “I had many failures until I achieved this success.”

And, yes, we all pay lip-service to success being in the eye of the beholder. But let’s get real here. There is only one kind of success that counts when it counts – when you are raising money or making the headlines or being invited to headline the big conferences – and it’s the payday.

So what if we could, as Claudia puts it, get through all the piss and shit and lies that kill other people? What if, when we stumbled, we understood that it was just part of the natural process of navigating the unclear path? I tell myself everyday I stumble that “this is just part of the startup story.” Every misstep, every rejection, every time I hit the big frickin wall, I say, “it’s the journey and if it were easy, I wouldn’t be growing and going somewhere I need to be.”

I used to be afraid of talking about my failures. But the more I do, the more people I uncover who want to talk about theirs, too. A couple of years back I was at FOO Camp and I encouraged a group of successful entrepreneurs to hold a session on failing. Let me tell you…the session was a fail in itself. Nobody could even talk about real failure there. It was all about how they hired the wrong person or chose the wrong programming language. There was very little honesty in that room. I decided not to talk at all because my failures seemed so epic compared to theirs. No wonder they were successful and I wasn’t!

I regret that now. I wonder what would have happened if I had piped in and talked about one of my very real failures. Losing a business to bad financial planning and ruining my credit. Losing a best friend over making a really selfish decision that ended up stinging me. THESE are things I learnt from. They were undoable. I pay for those failures to this day.

Years ago, I chose to live my life with the kind of transparency that would create real connections to real people and ever since then my life became fantastically uncommonly amazing. Yes, it leaves me incredibly vulnerable, but it also creates an amazing amount of safety for me. Having real connections with people means that I have an enormous group of people who would take a bullet for me. The only regret I have is that I didn’t do it sooner.

The lies ARE killing people. They are killing real progress. Real solutions to real world problems. If we took away the inflation of a few and really took a look at the landscape we would see that the majority of us are stumbling towards doing something meaningful.

Speaking of which, a big bonus…Hugh MacLeod‘s amazing cartoon that says it all:

“You’re not crazy. You’re not a failure. You’re just trying to do something that matters.”

Keep doing it. You aren’t alone.