“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.

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.

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!

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.

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…

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.

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.

“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.

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.
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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