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…

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Tyler Donahue

Writer @TheHustle @thriveglobal | Founder @th3kindproject @essentialblankets