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Brad Wason and Drew Osberg attended Startup Weekend Delaware on November 15th and pitched Ugly Outfitters, an online business that sells used and hideously chic Christmas sweaters for $35 each.

A little over a month later, the guys are expanding Ugly and finding success. They have added free shipping, every order is a surprise (yep, you have no idea what kind of Ugly you will get), and if you return your Ugly within 45 days…you get $20 back! How cool is that?

I spoke with Brad and Drew to find out what Ugly really means and how these two entrepreneurs will corner the market of Ugly.


Via The News Journal (Pictured: Drew Osberg, co-Founder & Brandford Wason, co-Founder)

What made you both attend Startup Weekend? 

Brad and Andrew: Our Ugly team was made up of Startup Weekend veterans, and a couple of us were actually present as coaches for all the teams. Fifty-four hours is a lot of time to fill however, and sometimes you have to take a break from coaching and crank out your own idea. The energy at a Startup Weekend is infectious. Hence why we all returned, and we were literally the first people to sign up for Global Startup Battle in Delaware.

How did this idea come about?

Ugly was born on Saturday afternoon of the weekend, while drinking a few beers in the back room of a very small italian restaurant. It turns out that copious amounts of pasta, a few craft beers and four friends make the perfect combination for creating a business centered around Ugly. Our team had already finished the idea we pitched on Friday, and figured we had an entire day left, so we might as well use those hours to our advantage.


 Via The News Journal (Pitcured: Steve Roettger, co-Founder, Sara Fabryka, Drew Osberg, co-Founder, Tim McIntosh, co-Founder and Amanda Curry)

How does your company define Ugly?

Ugly is awesome. Look, Ugly has been getting a bad rap since the word was born. Brands today seem to want to judge consumers and tell you what you shouldn’t wear, or that being blue, black, white, straight or gay are either good or bad things. To us, our brand believes in people. And we think people look awesome in whatever they wear. So, at Ugly we promise that whatever we send you, you’ll make it look awesome and can wear it with pride. Who knew confidence was ugly.


What made your realize that Ugly was in?

Ugly has always been in. But really we first noticed it when we started to do a little customer validation and research around our brand competitors. A lot of people claim to sell Ugly, and some do. But we’re positive if there’s a market for Ugly, we’re going to corner it.

Is Ugly the new black?

Well, Ugly does love black. And Ugly looks great in black.

Who is your target audience?

Our primary audience is women 24 to 39, based on response. So far, women make up 72% of our social audience and 68% of our customer base.

Why go to Ugly Outfitters instead of Goodwill or your grandma’s closet?

You shouldn’t have to spend time trying to find Ugly. We know ugly, because we practically invented it. So spend your time sippin’ lattes and less time driving across town looking for that perfect piece of Ugly. Just tell us your size and we’ll ship it to you. Fast. Our Ugly may be a little snug around your midsection or it may float like the Titanic, but it’s definitely Ugly. Oh… and if you return a sweater within 45 days, we’ll give you $20 back and an extra hanger in your closet.

Is there any other holidays that are or could become Ugly?

Well, we see Ugly as an everyday lifestyle brand. We’re in the process of creating limited edition, American Made (and Delaware printed) shirts for St. Patrick’s Day. Because, even Ugly Gets Lucky.


We also are looking to launch a 4-pack subscription of limited-edition Ugly shirts for other upcoming holidays, seasons or just because. Everything will be numbered, and made with love by the Ugly team. Try buying that at your big box conglomerate, you won’t find it.

And keeping with our unique twist, everything you buy is blind. Trust us, it’s going to be awesome, so just send us your details and size. We’ll even let you know when it ships, so you can wait at your doorstep glowing with anticipation.

How do you spread your Ugly message? Any specific marketing plans?

We’ve spread the message of Ugly primarily by word of mouth, some very specific targeted social media buys, and the good will of press. We watch our metrics like hawks, and through the powers of the internet leverage smart marketing, carefully crafted messages with advanced targeting. As an example, we have an unusually high following from Buna, TX. Which has inspired one of our upcoming shirts, by their Polka Dot House. Look it up, it’s amazing.




What celebrity (ies) embody the Ugly brand? 

We haven’t given this a ton of thought, however would like to personally high-five Jennifer Lawrence for coming out and saying that calling people fat should be a crime. And while we’re at it, probably Ellen too. Talk about two, powerful and super talented ladies, both taking a super positive stand for telling people they look awesome as they are, and who they are today. We suppose, an internet high-five will have to do for now.

If you had to send Barack Obama one sweater from your arsenal, what would it be? 

As for Barack and Joe (since we’re about 1-degree of separation from the Veep… it’s a Delaware thing) we would be more than overjoyed to ship them Ugly. We would tell you which one, but that would crush the surprise. We believe surprise is the spice of life, and everyone enjoys one now and again. Even if it that means you don’t know what piece of totally awesome clothing is about to arrive on your doorstep.

What is next for you guys?

Since we broke even and actually are going to see a very slim profit going into 2014 (not too shabby for four weeks, right?), we have big plans. Like we mentioned, we plan to make Ugly an everyday brand, and hopefully build a cult-following of customers coast to coast. Everything we make will be sourced and produced right here in the good ole’ USA, because let’s be honest, we need jobs in this country. We could produce Ugly at far greater margins out of the country, but we think putting friends, and small businesses to work to sell our little pieces of internet gold and slices of awesome is far more rewarding.

We’re looking forward to the launch of our first newly made shirts for St. Patrick’s day, and are working at a fast hustle to lock-up  unique partnerships for the new year. We’re also looking into buying a truck and creating an Ugly store on wheels so we can visit all of our new friends from Twitter, Facebook and the internet at large. We hope to expand our brand by traditional channels, events, festivals, local concerts, spending time on the beach, and through partnerships.

The Ugly brand is looking to partner with companies, celebrities, and people like us all over the World in spreading a message of acceptance, awesome and pride, one person at a time.

Connect with Ugly Outfitters on Facebook

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