There is something about a new year... This year I'm traveling to New York for New Years, partially for work and partially to catch up with my friends there. I really look forward to just hanging out in one of my favourite cities for an entire week with no real agenda. It seems like a perfect thing to do to reflect on everything.

And reflect I will. The photoshopped image attached to this post is how I've been feeling for most of 2010. Constant pressure. "Nearly almost verging on just about approaching bordering on *egad* just a little more and I'll have that ring!" is my first and last thought of the day. Don't get me wrong. I've achieved quite a bit. And grown even more! But as I was telling someone the other day, this is the first really hard thing I've ever done. I've done hard things. I've been through loads of challenges. Doing a startup takes the cake.

And let me qualify that even more. Building a product is challenging, but not the really hard part. It takes time and it's never quite right. You make a million mistakes. And the stuff you think will be awesome actually isn't. But I've done this within organizations. I've worked directly on product. I've tweaked and tested and planned and launched before. I've worked on everything from wireframes to design to UX. I've got it right and wrong. It's the fun part of a startup. And I've worked on the community building/marketing end of things, too. That, too, is a challenge. People are busy and don't care about your messaging, etc. But I'm good at bridging building something with meaning to match people's desires. And I've gained an amazing group of supporters over the years who are really patient when I screw up.

So, yeah. Building a product and selling a product is challenging, but well within my abilities. The Frodo-photo was imagined in the past month or so as we look for funding. I've built businesses before. Small but profitable, sustainable businesses. I've never had to seek outside funding (other than a line of credit). Building a startup usually requires outside capital. And, well, we are no exception to this rule. We've spent the year, all of our savings and some generous loans from friends and family bootstrapping Shwowp. We held out as long as we could from pounding on those doors. There is a good reason why. This shit is heartbreaking. I used to think there was nothing more frustrating than dating. I was wrong.

Let me set the scene:

You make a connection, prepare a pitch and demo, have a great meeting filled with amazing ideas, you shake hands and they utter the words, "Next steps." You leave with butterflies in your stomache. You liked them a LOT. They GOT it. You dream of not only being able to pay your rent next month, but how they would be great additions to your board with their experience and connections. You send an upbeat follow up email.

And then they don't call. They don't write. And your heart sinks into your stomache.

So you cheerfully type another follow up: "Let's explore those next steps you talked about!" And the airwaves are silent.

Then comes the part where you start beating yourself up. "Is it ME? Did I say something wrong? Did I come across incompetent? Not realistic enough? Should have I worn the blue dress instead? Maybe it was a tweet? Or maybe I tweet too much and they think I'm not committed? Maybe I should write an email explaining that my tweets are part of the overall marketing. Staying on top of things. Maybe I should stop tweeting. Could it be the product? Yeah, it's pretty early on and we're super beta. But they realized that. They *said* it looked like a great start. They understand that we can iterate quickly...especially if we can hire another developer. They understand we've built quite a bit on very little. Right?"

And so on. Instead of focusing on the product and the community, you are sitting there fretting over how a promising meeting turned into radio silence. Or worse...the soft rejection, which I'm sure is a standard gmail template for VCs and Angels, "Great team, great product, but we are passing due to where we are at and where you are at right now. But keep in touch as you progress. We'd like to talk more in the future."

Facepalm. What happened?!

You give yourself pep talks. Read blog posts from other CEO's that tell you they talked to hundreds of potential investors before they got to a yes. Hundreds?! The dozen or so you are talking to are already shortening your lifespan.

Yeah. So that's kind of my every day right now. Yes. It sounds a lot like dating. But at least I can AVOID dating!

Don't get me wrong. I will go through this pain as long as I need to in order to build my dream. I don't give up easy and I love the people I'm working with and how the product is evolving. I'm so excited about how fast we are progressing (launched in 6 months and improving significantly every week). I got giggly tonight on Tummelvision.tv talking about an upcoming bookmarklet we will be releasing. I've never been known to throw in the towel when it comes to hard work.

Dammit. 2011 is the year I grab that motherf&*)ng ring. I'll get to put the focus back on building an amazing product and user base. It'll still be hard work and there will be many trying days, but I *will* level up and breath a little bit easier than I have for the past few months.

It's going to be a fantastic year. A year of building and growing and learning and reaping...I will make it to Mordor and destroy that ring and be ready to meet my next big challenge with renewed strength.

What are you shooting for in 2011?

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