By Sue Kim (Founder, Dress Me Sue)

I was a happy cog for 10 years — plugging away in my little corner of the old school Chicagoland e-commerce and digital scene. I had begun my IT career late (age 28), but managed to work my way up successfully. I was an overachiever, a manager’s dream. The harder I worked though, the more I knew there was something amiss.

One day I started to explore blogs and stumbled across notice of a Women 2.0 Startup Weekend in San Francisco. I registered and immediately bought my plane ticket. I was locked in. So I went.

Friday pitch night at Startup Weekend tops my list of most scariest experiences ever.

My self confidence was so low that I abandoned my idea immediately after pitching and just walked around gabbing (with secret plans to ditch the weekend). By some grace unknown, my team was formed around my idea — and in the end we had a great time.

Dress Me Sue is the Etsy of personal styling. We help busy people solve the headache and hassle of figuring out what to wear by putting them in touch with their local style hero. Our advice platform delivers on service and experience by integrating the best of web, mobile, email, and text. This is an opportunity to break new ground in experiential shopping.

I am not exaggerating when I say that I was beyond green.

EVERYTHING felt new and not in a good way. I was not familiar with modern day product management and user experience methodologies, let alone lean startup. I remember the distinct feeling of bewildered insecurity watching Cindy Alvarez‘s team walk around for A/B feedback on some simple yet sophisticated sketches. “How did they do that? I can’t do this.” It sure would have felt good to hightail it back to my one-room schoolhouse where I could get straight A’s forever.

I remember once my teammate mentioned checking the code in as open source — I immediately asked him to make it private and thought “What the hell? Why would we want to share our code base right now?” I recall his slight pause of surprised unfamiliarity, as he probably wondered what kind of rock I had crawled out from under. I was heavily habituated in waterfall development, new to Twitter, never heard of GitHub.. the list goes on.

It’s been 1.75 years since I stammered through that first pitch for Dress Me Sue.

Notice I say 1.75, because it sounds better than 2 years, which is like an eternity for a startup — and the equivalent of 10 regular human years. I have wandered around the forest many times before reaching the sublime place I’m at now. And what place is that? Let’s see. I’m out of a paying job, out of cash, and out of credit. Yet strangely for the first time I feel truly alive.

Finally stepping into the role of founder — a role I’ve been fearing, deluding myself away from, and misinterpreting altogether. I’m at the next beginning — built a prototype, talked to customers, pivoted, revamped the interface, and got agile technical advisers. I have a paying customer waiting for the next iteration.

I need a CTO or enough cash to build it and see how many more paying customers there are. What I really need most is to get rigorous and honest with my lean startup measures.

If you ask me, 1.75 years is pretty damn good given where I came from. I had to unlearn everything — then learn everything.

My evolution as a founder has been a lot like the very process of validating a startup idea.

In the end, all you have is your instincts, persistence, and learning. Your ability to make it has everything to do with your relationship to learning, and your skill at distinguishing true instinct from all the extraneous bullshit your brain produces.

I am now a full time founder — not because I can afford it, but because the role I’ve stepped into is incompatible with the way I used to work. Believe me I’ve tried. I’m under a 2-month negotiation with my husband to make something happen by end of July or “move on with our lives.”

I have no idea what will happen in 2 months but I can’t worry about it. I just have to manage the constraints while following my vision to its natural conclusion. The vision now has a life of its own, and I’m the human being who’s finally agreed to lead it.

About the guest blogger: Sue Kim is founder of Dress Me Sue, a self-help app disguised as a fashion app. She blogs about her first-time startup experiences at Tumblr ( and welcomes any technical and copy-writing contributions to her crusade to dress the world and eliminate wardrobe pain forever. Sue lives with her husband Todd and silly greyhound Skeeter in northern Illinois. Go ahead and tweet her @suesunmi and her startup at @dressmesue.