Lessons from my first failed startup: The Clueless Closet App ;)

Tyler Donahue
3 min readAug 6, 2020

It was mid-2015 and I was anxious to start something that exercised more creativity than selling houses (I was a realtor at the time).

So my friends and I decided to start a company. We started with some simple questions that most ask when thinking about starting a company. What problems do I have? What do I do often that could be improved upon?

Jackie: “I shop for clothes online but matching outfits is hard because you can’t really see what the items look like together”

Kenny (software developer friend): “I bet I can make an app for that”

Me: “Alright let’s do it, what do you need Kenny?”

And we were off. None of us had built an app before but we were confident that shopping for clothing online could be improved drastically. Also, ThredUp had just raised 81 million from Goldman Sachs so we were pretty darn excited as kids in our early 20's.

After a month of brainstorming and storyboarding we had a plan.

We were going to build a mobile app built to help boutique clothing retailers improve their online sales and user experience via a reinvented interface for mixing and matching clothes to build outfits (think Clueless). The app displayed clothing as outfits on a wheel so the user could mix and match different items to build an outfit.

The app had 2 main functionalities:

1) Storefronts that contained clothing from 1 retailer. As a user, you could enter a store’s account and see all their items on the wheel we built (scroll down to see our teaser). The store would have individual items like a traditional online apparel store but they could also pre-load outfits.

2) A feed containing clothing from several retailers. The feed would be non-traditional. All the items would be displayed on the wheel (the teaser below helps articulate this a bit if you haven’t watched it yet) The goal was to unbundle the large e-commerce clothing businesses on Amazon with an improved user experience and marketing tools for the clothing retailer.

We had 2 main monetization strategies. The first was a small transaction fee on items sold through the app. The second was ad revenue from…



Tyler Donahue

Writer @TheHustle @thriveglobal | Founder @th3kindproject @essentialblankets