My Startup Story: Leading Up To Launch

You may have read my post from early October called Starting Up Air Tailor: From Concept To Beta. I talked about how I conceptualized the most convenient way to perfect fitting clothes and introduced our first beta, which ended up being featured on Product Hunt and Entrepreneur. It’s been two months since that beta was released and I wanted to give an update and introduce Air Tailor Beta 2.0.

Many people aren’t exactly sure what “beta” even means. To be honest, we got the question a lot and I think it scared some people away when I would respond. Beta is all about testing, feedback, and good ol’ trial and error before a startup goes mainstream. We had around 200 signups for Beta 1.0. My mentor Matt Rizzo (one incredible Warby Parker Technical Product Manager) stressed that I interview as many of these sign-ups as possible so that I could really understand what they’re looking for in an on-demand tailor. The rest of this post highlights some pivots that were made from the feedback that I received from talking to about 30 people from different walks of life.

First and foremost, our texting order process used to be completely automated. There was no room for customers to arrange special requests, it didn’t feel warm, and it gave us virtually no insight into how the customers were feeling. We ditched the robots and set out to form real relationships with our customers through real conversations. We want to innovate the alteration industry through technology, but the conversation between customer and tailor still must exist.

I began the search for clothing alteration experts to work as part of the Air Tailor founding team. While interviewing the potential candidates, I made sure to convey that we are a startup aiming to innovate by eliminating in-person fittings, so they would need to have confidence in altering clothes without in-person fittings. It was a challenge not everyone who applied felt comfortable with. Then Emmanuel walked in. He served in the military, then went on to study fashion design and alterations. I evaluated the samples he brought, and felt a strong connection with his work ethic and quality standards. Air Tailor made its first hire.

Emmanuel has been a pivotal addition to the Air Tailor founding team. In addition to doing the alterations, he’s helped me come up with fitting and alteration protocol. Before Emmanuel, we were asking customers to mail in their well-fitting clothes so that we could study and replicate the fit onto another garment. This didn’t totally work because fabrics vary in how they lay, drape and stretch on the body. Now, we walk customers through what we call “Guided Fittings”, where they place safety pins on their garment. Basically, you pin your garment like it’s on a mannequin.

Our new system was working and we got our first few orders! One of the customers received their order back and was so pleased, they offered to give us a quote and before/after image for our marketing:

“The customer service was superb – I loved being guided through the whole process via text message. The sleeves of my denim jacket now fit perfectly.”

I have to be honest, it took a few orders with positive results for me to feel fully confident in what I was building. As a founder, I can’t convey how much of a rollercoaster the startup experience is. Will this work? Even if it does, how will the world respond? Thankfully, our hard work was paying off and Air Tailor began generating more orders and positive buzz. I hung a sign outside our office and created a snazzy phone greeting, take a listen:


I redesigned a bulk of airtailor.com to reflect all of the new exciting changes. Now, when you sign up, we’ll mail you an Air Tailor Welcome Kit full of goodies: safety pins (to pin your garment), collar stays, a measuring tape, a handwritten note from your tailor, and packaging to send us your first garment.

I couldn’t be more excited about the release of Air Tailor Beta 2.0. The world can officially experience better fitting clothes easier than ever before.

If you are interested in learning more about me and my journey in creating Air Tailor, take a listen to an interview I recently did on Episode 8 of Hustle Sold Separately.