horsepigcow

I just got home from a 12-day roadtrip to Boston and NYC. The first thing I did was to pour myself a shot of tequila. Then I put on Bonnie Tyler’s Total Eclipse of the Heart. On repeat.

I read Mark Suster’s amazing post on TechCrunch tonight as I crossed the border from the US to Canada (yay! I got data back!). Like many of his posts, it struck a chord with me. It talks about the rollercoaster that is being a startup entrepreneur. It spoke to those really high moments when you have an amazing team and you are gelling and pushing from dev to production and everybody is excited. And the other highs when you come out of a great meeting with a potential funder who seems really gung-ho about you. And the other highs when you get press on TechCrunch or Mashable or even in the New York Times. And when you get amazing customers who are using your product even though you know you have a long way to go to make it usable. But it also talks about the lows. And those lows are heartbreaking. And, well, I’ve experienced many of those, too. When you have to tell those same amazing team members that you can’t pay them (or yourself). And when those same gung-ho funders turn cold a day or two later with an email that goes something like, “We discussed this and we’re going to pass.” And when the amazing customers don’t come back because you aren’t pushing enough fixes or improvements because, well, you can’t pay your employees because, well, the gung-ho funders are passing.

And you know the potential. If only they could see the amazing energy in your team. And how dedicated they are (the many who are working even though they aren’t being paid). And your roadmap answers the needs of your users, but it’s slowed to a snail’s pace because development takes money. That golden ring is just a couple of dollars away.

But you start to feel the squeeze yourself. You have $2.99 in the bank. You are calling your landlord asking for a rent extension. You are ignoring calls from numbers you know are your credit cards wanting to be paid. But you still believe and, dammit…you just need one person. Someone to believe in you like you believe in you. Someone with money to invest in that belief.

I’m the most fortunate person in the world. I stayed with a good friend in Boston and got to stay with two good friends in New York. And I have hundreds of good friends who will buy me a meal, a drink and who have even put Friends and Family money into my dream because they believe in me.

Yes. We know the market is getting crowded. Yes. We know that they holy grail of consumer data is a long shot. Yes. We know that Facebook or Google or Amazon or Microsoft or American Express or MasterCard or Visa or any other giant with huge resources and big teams and marketshare and blah blah blah could flip a switch at any moment and challenge anything we are doing. We think about this daily. We understand the risk. We get that this is a crapshoot. And no. We can’t guarantee the future. But we believe. We believe in our team. In our dream. In the vision.

I would have stuck with my cushy speaking/author career if I didn’t believe. Cassandra would have stuck with her cushy VP job with a hot mobile development company if she didn’t believe. Jerome would have stuck with his cushy development firm with a constant influx of clients and cash if he didn’t believe. Jesus, he has a baby due any day. His amazing wife, Kim, wouldn’t even dream of letting him pursue this dream if she didn’t believe. William would have stuck with his cushy growing design consulting (and holy crap he is talented) if he didn’t believe. Robin, who I rely on constantly as the most amazing eye on the market, would have taken that cushy job offering her the moon if she didn’t believe. We all took on this very personal risk…and we know the risks…because we believe. We’re not masochists that want to struggle. We truly do believe.

Egad, where am I going with this?

The other day after a heart-to-heart, I told Cass that I find it therapeutic to work my thoughts/frustrations/ideas out on my blog and on Twitter. I’ve tried to keep a journal, but it becomes a spiraling mess of nonsense because I don’t think about the audience. I’ve tried to have one-on-one’s, but that just doesn’t bring in enough outside perspective. And, really, I believe strongly in the message of Jeff Jarvis‘ book in progress, which I believe to be that being open and transparent with your experiences brings more good than bad to one’s life. So I bear my heart on my sleeve for the world to consume so that everyone can a) learn from it and b) offer me their own perspectives on it. For better and for worse.

I believe in what we are doing. Some days I don’t even grasp what that means. And I know that doesn’t make perfect sense. Shwowp isn’t about showing off purchases. It’s not about daily deals, either. It’s not about posting pretty things for people to aspire to. It’s about working towards that holy grail…people owning their own consumer data. Vendor neutral. And highly personal. We leave a thumbprint on the world through the ways we express ourselves. Through what who we hang out with. Through where we go. Through what we read. Through what we listen to. And YES, through what we buy. And this world is filled with endless choice, but the choices we make are personal to US. From the clothes we buy to the brand of dishwasher detergent we use. It has a story. It’s the story of who we are. And that story has power. I see that story ending the nonsense that is tracking software and cookies. Because we (you and I as people who, yes, consume) should be able to use that taste data to filter through the noise.

And dammit…the compelling part of this story for investors is that, once you help us unlock that power, there is a huge revenue upside. And I can’t freakin believe I just typed the words revenue upside.

Someone is going to see this. Someone is going to understand that we are not only the team to build this, but the team to deliver this powerful message and to make it hella amazing. And we are going to do this. I don’t do anything that doesn’t have a ‘change the world for the better’ bent. And through this heartbreaking process, I feel it slipping. I hear myself saying things like ‘revenue upside’ and ‘go to market strategy’ and I chase the witches broom just so that someone…anyone…will help us get there. Cass and Jerome and I will lead us there.

As Mark said in that fateful post (I swear that guy reads my mind), “Maybe even tequila. And the next morning – water off a duck’s back. We’ll find a way. Startups weren’t mean to be easy. Back to work.” We’re going to keep working at this. I look around my apartment and know I can part with everything here if I have to. And looking back, we will have the most EPIC FUCKING startup story to tell ever.

Heh. Actually, I do believe this is not really the most epic startup story ever. It’s a startup story. It’s what we all go through. Because truly groundbreaking startups all go through this. They are all crazy enough to believe in something that is difficult to ‘elevator pitch’. They see the world in a different way.

The key is getting in front of someone…anyone…that believes in that same damned crazy, risky, unknown different worldview and believes in you to achieve it. We’ll find it. We will.

You know that state you are in when you are a child and pretty much everything is possible? Someone asks you what you want to be when you grow up and, because the sky seems like it’s the limit, you pick the best possible, most awesome thing in the whole world? Like astronaut or cowboy or princess or movie star…or in my case…pirate (post-Disneyland, I thought pirates lives seemed like the most awesome thing in the world). You could do anything, achieve anything, BE anything, accomplish anything.

Then people start telling you that you are unrealistic. I don’t know the exact age, but it happens slowly at first. People will smile sweetly at the crazy whims of a small child, but then at some point, they feel they really must let you know about reality. Reality is harsh. Reality means that sky isn’t really the limit, that there is a much lower rung on the ladder that you could reasonably expect to reach. Only 0.1% of people become astronauts or something like that. There are tests and years of school and more tests and, well, you probably won’t be the one to get to ride in that space ship to the moon, so maybe you should stop and think about doing something a little more practical.

I think that happens at a similar time to being told that Santa Claus is a bunch of hooey made up by retailers to sell more stuff.

Well, like pretty much everyone else in the world, I had a whole lot of years of having the ‘skys the limit’ ideas hammered out of me and I gave up that dream of being a pirate. That was, until I lived in San Francisco. San Francisco is crawling with pirates. Pirates of all types. And for the first time in my post-Santa Claus believing life, I started to see the sky again in my limits. It took my career from sputtering along to taking flight. I could do anything. And I achieved a great deal. I did impossible things all of the time and lived an impossible life. I became an author. I started movements that spread all over the world. I became an in-demand public speaker. I became a thought-leader. A country girl from rural Alberta who was told to be realistic unlocked her innermost unrealistic child again…but being unrealistic was the best thing that ever happened to me.

Years ago I read Tom Kelly’s The Ten Faces of Innovation (totally loved it) where he talks about the Devil’s Advocates as not being a desirable part of any organization. In fact, Kelly see’s the so-called Devil’s Advocate characters as being the biggest potential innovation killers in any organization:

(A) devil’s advocate encourages idea wreckers to assume the most negative possible perspective, one that sees only the downside, the problems, the disasters-in-waiting. Once those floodgates open, they can drown a new initiative in negativity.

I wholeheartedly agree with Kelly. Devil’s Advocates, or those people who like to talk about the downsides and think small, do only harm. Sure, sure. We don’t want to live unrealistically and haphazardly! That would be downright foolish! Or would it? The truth is what a Devil’s Advocate or anyone who tells you that you cannot be an astronaut or pirate or princess or that there is an age to stop believing in Santa Claus is doing is adding an artificial barrier to what you can possibly achieve.

The truth is, reality happens. But it happens very differently than the naysayer thinks it will. The minute I stopped putting false ceilings on my growth, I grew. If you somehow erroneously think you can make a billion dollars in the next year and nobody tells you it is impossible or silly, you will probably make it a good deal further along that road and -hell- maybe even achieve it because you missed that barrier! And if you don’t, you learn. Experience is very different than a naysayer. It gives you lessons…really personal lessons to understand how to do better. Devil’s Advocates are merely projecting their own fears onto you (ask a Devil’s Advocate about their experience in any area they are telling you that you can’t achieve what you want to and I’ll bet 9 times out of 10 that experience will be nil). Nobody that gives you the ‘realistic side’ of things does you any favors. I learnt that way too late in life.

It’s still a struggle for me. I still have plenty of Devil’s Advocates in my life, even when I try to limit it. Hell, I have one that lives inside of my head that I have to keep at bay 24/7. But my mantra is and will always be, “Why not?” because at the end of the day, nobody (who really knows) told me it’s impossible to be an author/speaker/ceo of a successful startup/marathon runner/pirate.

I didn’t believe there *was* such a thing. Or rather, I believed there was, but I was never going to be one of those people that experienced such a feeling.

I hated running. With a passion. Besides chin-ups, running was my most hated activity growing up. I could do sprints, but I stuck to under 200m distances. I couldn’t fathom my body moving in that fashion for any longer distances. There were these fitness tests they did in school that included the 12 minute run. I walked for 1/2 of it. It wasn’t that I was in bad shape. I’ve always been athletic. I played volleyball, badminton, basketball, figure skated (for 10 years – I even taught it), I weight-trained, I could do 200 sit-ups without stopping (at one point I held the county record), karate, I was on the swim team (was a jr life guard), etc. growing up. But running was my nemesis.

That was until just after my 37th birthday this year. Maybe it was the training I was doing leading up to my birthday that included a good amount of cardio (I usually stuck to the stairmaster, HIIT on the treadmill and cross-fit challenges that got my cardio up). Or maybe it was my state of mind. But one day, my good friend and now marathon training partner, Eric, decided he wanted to start working out with me and suggested we run on the treadmill. I reluctantly agreed, but did it. And it was fine. I think I ran for 30 minutes our first session. At about 20 minutes, I stopped feeling the pain and started feeling the high.

I’ve been hooked ever since.

Today I ran 9 miles (or 14.5km). This is significant. That is 1/3rd of a full marathon length! For those of you who have run all of your lives, you may be thinking, “Meh.” But for me, that is a HUGE victory. I ran it and it felt good. I had several runners high-gasms. And I definitely could have kept going. My knees where a little achy and, on the treadmill, it gets a bit tedious, but I picked up speed at the end and could have kept going. Next Sunday I do 10 miles. 10 miles!

In the past 6 months or so, my body has fundamentally changed. Running has not only changed my physical shape (my hips are actually narrower than my shoulders for the first time in my life), but has changed my overall stamina all around. As I run, I can feel my muscles lengthen. I visualize how each one is connected from toes to the top of my head. I’m more aware of my body than I’ve ever been in my life.

Mentally, running prepares me for anything. Not only do I become incredibly zen while running, but it has carried into my everyday world. When I don’t run regularly, I start to get less patient, less calm and more anxious. When I’m running regularly, I handle everything in stride (so to speak). Running has helped me become an adult about things in the best possible way.

My training schedule is pretty rigorous over the next while. I’m running the distances, but I need to increase my speed over time. I also need to do more stairs (I still get out of breath!). The marathon we’ve chosen is quite a marathon: The Great Wall of China! There are 5164 steps. The top female runner completed it last year in just under 4 hours. I’m not aiming to beat that – just finishing it will be a victory – but it’s a nice goal to shoot for. Eric bought me the book 4 Months to a 4-Hour Marathon. The thing is…I know if I keep training hard enough, I feel I can complete this one, steps and all, in at least under 5 hours.

Just think. In just 10 months of training, I will go from not being able to run 12 minutes to completing an über challenging marathon in a good time. Crikey. I can’t wait to see what my next challenge will be! We aren’t finished putting together the pieces yet, but we plan to raise money for a school in Nairobi as part of our goal. Eric is even more ambitious than I am.

Thank you to everyone who has encouraged me, trained me, advised me and just generally followed me along this journey. I promise to keep challenging myself!

Anyone who knows me well, knows the following bits about me:

• I work hard, I play hard and I live hard
• I am incredibly serious, but rarely somber
• I lead through laughter, not law

Mid-last week, I had a meeting with someone who indicated that he was concerned that I wasn’t serious enough about my leadership role at Shwowp. It was a statement that floored me. I eat, sleep, live, breathe and otherwise obsess about my company. I go to bed consumed by thoughts of it and wake up consumed by thoughts of it – and when I dream in between, I am dreaming about it. There are just about 3 Gazillion balls in the air at any given time with the company and I’m blessed to have two co-founders who co-juggle alongside me. It doesn’t mean that the work is lessened. We can just cover more ground together.

So I asked out of curiosity how I was giving that impression (because it wasn’t the first time someone hinted at it). The answer was that it came down to my tweets and posts and generally casual disposition. “You just don’t come across as very serious,” he explained.

My first thought was, “Dude! I’m the most serious bidness person I know!” but I stepped back and realized this may be a moment to be somber in my reply. I think I used a few big words and furled my brow to look really serious. I’m not sure how convincing I was.

But I threw in, “Do I need to be somber to be serious? Because that isn’t my style.” And it isn’t. My signature is smart, but fun. Inspiring, but light-hearted. Even when I’ve delivered the most serious subjects while giving a talk at a conference, I’ve aimed to make people laugh their way to having the idea stick.

It took me years to actually approach the world (and especially business) in a way that feels right and genuine to me. I struggled with trying to emulate stereotypes in the most awkward way through my 20′s. I studied the ‘greats’ and tried to be just like them. It never worked very well. Then one day I decided I would just be myself and, somehow, it worked. It worked wonders and everything changed. I gained confidence. People were more receptive to me. Ideas flowed. And I felt like I really hit my stride. But every now and then I encounter a situation where my approach is misinterpreted. My thoughts when it happens? “Meh. I’m breaking the mould.”

So let me assure you if you didn’t already gather it…I am VERY serious about my role at Shwowp. I don’t talk about it incessantly because it’s not my style to be pitchy (except when I’m expected to pitch). Everything I tweet and blog and post everywhere is tangentially connected to my immersion in Shwowp, but aimed to keep people’s interests, too. My running has everything to do with Shwowp. It keeps me grounded and sane and able to handle what has been the most financial uncertainty I’ve ever faced. I turn down most speaking gigs, but those ones I accept are because I think it will benefit my company (I actually have a speaking caveat that I only talk about things related to Shwowp now – no more book stuff). All travel is related to Shwowp. Every event I go to is about Shwowp (whether it’s for recruiting, learning or networking). Everything I buy is because I want to post it to Shwowp. Everyone I meet with is related to Shwowp. I really don’t have a life outside of it and I’m seriously okay with that. I love what we are doing. I love the startup life. I love my co-founders and co-workers.

So yes. I’m very serious, but I’ll never be somber. This is just too much awesome to be a downer. And besides, it’s my “job” to set the tone for my company…which will always be about never taking ourselves too…um…seriously.

Okay…that may be a *bit* of a stretch, but let me tell you, this shit is about to get real. Real exciting, that is.

Someday I will tell the whole story and give all sorts of tips and words of wisdom to other people following the path of launching their startup and building a dream, but for now I’m in the middle of it, so I’ll just tell you where I’m at. Raising money to grow a startup is different than anything I’ve ever done…and probably different than anything most people have ever done. It requires mustering a skill I’ve never mustered before: asking for stuff.

That’s pretty much it. I’ve heard that in sales, you have to hear 99 no’s before you get to a yes. That, to me, sounded like the most painful process in the universe and something I mentally noted that I wouldn’t attempt in a million years. I’ve heard folklore about people who are actually *good* at this sort of thing: people that are good at asking and getting rejected (repeatedly), then persisting without blinking an eye. I thought they were made up or some sorts of emotionless freaks of nature I’d never want to encounter. If ever I imagined myself being forced to play this role, I’d instantly go into anxiety attack mode. Even the thought of it drove me to drink. I imagined that repeatedly gouging my eyeballs with a fork would be more fun.

But a funny thing happened when it was my dream and vision that was/is at stake. I mustered. I rallied. I stopped worrying about being rejected and I started thinking about learning from every rejection…or even to stop thinking of them as rejections at all, but instead, poor fits or great opportunities for feedback. Instead of rocking my foundation and calling my ideas into doubt, these rejections made my conviction even stronger. Not to mention that, just like anything, it gets easier. The first ‘no’s sting. They do. But then you learn to take them in stride. Next thing you know, you get better at realizing when to walk away and when to go deeper. I can tell early on now when the investor/entrepreneur relationship won’t work. I’ve actually closed my laptop mid-presentation, thanked the person and walked away. Sure, it’s practice, but I’d rather be spending that energy on convincing the right investor than practicing on the wrong one.

So here we are in a tight spot. Bills outstanding. Employees who will need to be paid. My own bank account teetering on double digits. But there is a light at the end of the tunnel! As I stated in previous posts, I’ve knocked on a few doors over the past months and, for a while, was feeling a bit frustrated. But it only takes one door to open and several others will follow. And, darnit, that door is opening (and what an exciting, awesome door it is…the Angel we are talking with is someone I admire a great deal…a dream!)!

But it’s not over until the fat lady sings…or…erm…the fat check is deposited! And, well, there is still loads of work to do, people to talk with, terms to negotiate, improvements to make to the product, etc. And at any moment, things could fall apart into a heap of bits that I’ll need to sweep up and deposit into my ‘Lessons Learned’ basket, shake myself off and try again. But no matter what happens, I will. If I have to sell everything I own, move in with my cofounder (Hey Cass!), spend evenings and weekends talking dirty on a 1-800 number…I’ll do it. I need to. I believe in this so fundamentally, it’s nuts.

And in the meantime, we have done a temporary restructuring of our Friends and Family convertible debt round from mid-2010 and are opening up a last minute offer to Friends wanting to get in last minute. Juss sayin’

I can’t wait to do the post-mortem on this round. I can’t wait for the day that I exhale a bit. It won’t be the last challenge and it certainly won’t be the biggest challenge, but I know I’ll relish in the victorious end of this leg of Shwowp’s journey and the incredible amount of personal growth I’ve experienced as part of it.

Thank you so much for continuing to support me…in every way, shape and form! This *is* actually hella fun.

It’s very Buddhist of the real-time social networks to design our experiences in the now. What are you doing? What are you reading? What are you seeing? Where are you at? Who are you with? What are you wearing? All of these are questions we can easily answer. I can tell you that I’m working from my home office, writing a post on the real-time, wearing my skinny grey jeans and my favorite sweater and I’m sitting alone, although I just finished a podcast with the awesome Heathervescent. That’s easy. But ask me about what I was wearing/doing/seeing/etc three weeks ago? Not so easy. There is a whole lot of page scrolling involved in that task.

I do actually spend most of my time in the present – some of it planning for the future – but more and more frequently, I’m becoming quite irritated with the inability to see my past. Even my recent past. When people tell me that Facebook and Twitter is all we need (they cover the present quite nicely), I have to disagree. They are platforms for the now and, even if it’s a less frequent need, I find myself needing to access the history quite often.

For instance:

• What was the name/location of that awesome place I lunched with Emma Persky at again? Oh yeah, Pecan. Foursquare is pretty good at history.
• Did I introduce Ethan and Umair like I meant to? Yep. Hashable has me covered.
• What did I make my awesome friend Bryan Thatcher when I stayed with him in NYC? Oh yeah, French Toast. Foodspotting keeps that record.
• When did I travel to Phoenix last? End of October, 2010. Thanks Tripit!

And these may seem trite and unimportant, but there are many practical reasons why I need to remember. Number one, I’m getting old and the memory isn’t *quite* what it used to be. Besides, I travel quite a bit, meet quite a few people and switch gears many times over just a matter of weeks. My real-time life necessitates a temporary erasure of my near-time history in order to just know where I am and what I’m doing today! And yes, I am a bit of an exception to the rule, but it just means I need my history a bit more frequently than most.

But more practically, remembering who I met when and where we were is incredibly useful information. So is what I bought when and for what purposes. Where I traveled, which event I attended, what I read and when, even what I wore (for purposes of not duplicating that same outfit too many times in the same company)…all useful. Practically speaking, I’ve used some of this information for tax purposes. I’ve used some of this information for giving advice to others (where to eat, what to eat) and for planning my own upcoming trips and outings. I’ve dug back into many pages of history to recall when I met someone and how I met someone so that I could properly pick up our conversation.

And the biggest advantage of having an easy-to-access history is the ability to visualize it and get a sense of the Taste Trail I’m leaving behind. WhereDoYouGo is an awesome mashup of Foursquare checkins and Google Maps that can give me a snapshot of the areas of whichever city I have hung out in. In Montreal, I stick close to home. In New York, I stick South of Central Park and have only hit Williamsburg and Park Slope in Brooklyn. In Paris, I get around quite a bit. I find this fascinating. It tells me a bit about who I am, but also where I need to go to get out of my comfort zones. I think it would also be fascinating for, say, a Realtor who I approach to find me a place to live, or for businesses looking to open a location to serve people like me. I’d share it if it enhanced my life, too.

Lots of people talk about the impact of the real-time web and how it benefits businesses as well as serendipity – and it does! – but history is also chock full of relevant and powerful information. The power of the new breed of startups that are emerging right now isn’t just that they are niche (food, shopping, location, connections), but that they are also aware of the impact of historical data and how that will drive future decisions, connections and experiences. I think we are just scratching the surface on how this data will work to enhance our lives as individuals and businesses.

In order for all of this to work, though, it needs to work together. Although Twitter and Facebook connect allow for this data to move in and out of their platforms, our Taste Trails are still fragmented. Some companies, like Hashable and Runkeeper, are doing a good job of tying in other verticals (Foursquare, for instance), but rather than pushing each one of these companies to work with a myriad of APIs, shouldn’t we be thinking of how we could make the data flow more easily? Thor Muller, years ago, talked about the future of ScrAPIs in relation to the web. Why not have data marked up properly so that it can travel in an easily standardized way? This is definitely the call of Microformats. A couple of years ago, while working with the now pivoted Strands, Chris Messina and I came up with the idea of hTaste – a microformat for marking up preference data that could travel between sites, snowballing into a really fantastic overall measure of our Taste DNA. I think it was just ahead of it’s time.

I’m no technologist (man, I wish I were), but this stuff really gets me going. Living in the present is necessary and awesome, but as I’m doing so, I’m creating a rich history that could help unlock an even richer, personalized future. I’m looking forward to being part of creating that outcome.