Starting Up Air Tailor: From Concept To Beta

About six months back, I voiced a pretty intimidating concern to my mentor that my small necktie alteration business wasn’t quite growing the way I had hoped. He (Matt Rizzo, one incredible Warby Parker Technical Product Manager) encouraged me to think outside of the box. He asked if I would consider altering other garments, like shirts and pants. I pretended to be open to the idea, but I knew nothing about altering shirts and pants and it scared the shit out of me.

As frightened as I was, I took the following weekend to really think about what it would take to make it happen. I always try to approach problems with questions. In this case, I asked myself why altering clothing scared me so much, and why online alterations have never been done before. I dug deeper until the inside of my closet door was covered in papers outlining the concept. I felt like James Bond with a secret stash of important documents proving to myself that the mission was indeed possible. I continued dabbling, and bouncing ideas around to refine the concept. The overarching vision was to make clothing alterations more accessible through convenience and affordability. Air Tailor would revolutionize the way clothes fit.

My closet door while conceptualizing Air Tailor, June 2015

Because using “SKINNYFATTIES” just wasn’t appropriate outside of tie-land, my on-demand clothing alteration company needed a name. I came up with “Air Tailor” and designed the logo and brand style. By mid-August, theairtailor.com landing page went live. It captured emails from folks that were interested, and it served as a nice home on the web while I reached out to local tailors and messengers about working with us on the concept.

Air Tailor Landing Page, August 2015

I realized something sort of problematic. Sure, I had a cool concept, a killer brand, and interested people, but I still had no idea if we could tailor without in-person fittings. That’s kind of a big deal since that’s the big issue we were supposedly tackeling. I spoke with a few tailors asking if we could bring them customer measurements to tailor off of — they tossed me to the side like yesterday’s trash — there was too much room for customers to mess up their own fittings. Despite the rejection, I continued to bombard my network of tailors with stupid idiotic questions until I got answers. It took a while of research and testing, but I eventually found just how to tailor without in-person fittings.

I wanted Air Tailor to be huge, not just some small amateur hour sewing business. I wanted funding to make this concept soar, but I knew I couldn’t bring on investors until I had a rock solid team. I started searching for technical co-founders that could compliment my business development and marketing chops. I met with a few potential candidates, one of which I discovered had assisted in developing one of Russia’s largest online fraud scams — um, no thanks, buddy. Then, I met a promising soon-to-be Columbia masters grad, but eventually he admitted to being too busy to take Air Tailor on — I understood completely.

I decided to take a step back from the exhausting co-founder and funding search to focus on making a business development plan. That’s when I was able to start researching the platforms in which Air Tailor would be served on. Instead of a mobile app or website, I decided to start building Air Tailor as an SMS texting application. It quickly guides users through the process, while answering questions along the way.

Tailor by text SMS app in beta, September 2015

The Air Tailor Beta officially launched today and is already featured on the front page of Product Hunt. I have big plans for Air Tailor, so stay tuned as I build the world’s tailor.

This article also appears on Medium and is published here with the permission of the author