Business of HYPE is a weekly series brought to you by HYPEBEAST Radio and hosted by jeffstaple. It’s a show about creatives, brand-builders and entrepreneurs, and the realities behind the dreams they’ve built. On this special two-part episode, Jeff sits down with Round Two co-founder and vintage aficionado Sean Wotherspoon.

Whether you know him for his Nike Air Max 1/97 or as the owner of Round Two, it is without a doubt that Sean has made a lasting impact on today’s streetwear culture. The vintage connoisseur, designer, collaborator, entrepreneur, Youtuber, whatever it is you want to call him, does not define himself by any title as he says he “likes to do everything.” The Northern Virginia native tells us that from an early age he was obsessed with skating and sneakers. It wasn’t until his move to Richmond where his affinity for thrifting turned to a sport.

“I remember I found this vintage Polo bear shirt, and it was one of the first vintage items I found. And I loved it, because I loved the new Polo bear. But in my head I was like, ‘Holy shit!’ I pieced it together. ‘Wait this is what Polo must have looked at to re-release for the one that I got. ‘Holy shit I have an original.’ Once I calculated that there’s originals…it was all downhill.”

Sean and his co-founders, Luke Fracher and Chris Russow, opened their first store, Round Two, in 2013 in Richmond. With no supply chain to buy from, the three of them started with selling items from their personal closets. He emphasizes that he had no inclination the store would do well as it was all about “having fun.” But the audience grew and within their first weekend they had made a respectable $2,000 USD.

He attributes much of Round Two’s success to being located in a smaller city like Richmond, versus having more competition in a city like New York. When it comes to starting a business, he advises us that it “doesn’t matter where you live.” With six years under his belt, Sean and his team have expanded Round Two to eight stores with plans of going international. He remains adamant on keeping it brick-and-mortar as he loves giving people the unique experience of shopping the curation that him and his team have put together.

“We’ve created so many stories with people it’s unreal and I’m obsessed with that. Every person that leaves the store — like I said whether it’s positive or negative feedback — I  appreciated either way. I appreciate that person took the time to come by and create some kind of story with us.”

Later on, we learn that Sean doesn’t identify Round Two as a resale store. While the buy/sell/trade model can be applied to it, he emphasizes that their stores are more focused on a curation of items he deems “priceless.” These priceless goods, he explains, have no set monetary value, but rely on the idiosyncrasies of their buyers. For Sean, this is what Round Two is all about: creating an experience where you can walk in “with your eyes closed and not find something shitty.”

So listen in to part one of this extensive interview with Sean Wotherspoon as he details the early beginnings of Round Two, his passion for thrifting, and guidelines to what makes an item “priceless.” Stay tuned, as Sean discusses his collaboration with Nike and much more in part 2 next week.

This episode features references to the following:

3:54 – Eric Koston
4:13 – Early childhood
4:30 – Osiris D3
5:25 – Sean’s early style
6:00 – Rasta
6:15 – True Religion
6:47 – Diamond Supply Co., Staple, Crooks & Castles
7:02 – Burlington Coat Factory
7:18 – DC Shoes, Quicksilver, Billabong, Polo
7:54 – N64, Sony PlayStation
8:53 – Auctions & The Salvation Army
9:28 – Start to thrifting
10:37 – Vintage Polo
11:00 – ‘85 AJ1 “Chicago”
11:01 – Rumors
14:35 – Flight Club
15:41 – Round Two’s first shop
18:51 – First buying experience
21:11 – Pros to opening in Richmond
24:44 – YouTube channel
30:50 – Nike deal
32:10 – Round Two Hollywood
34:12 – Wale, DJ Clark Kent
46:37 – “Priceless” Items
49:33 – Curation over resale
52:19 – Webstore
56:29 – Amazon
58:26 – Round Two locations in U.S.
59:10 – Future expansions
1:03:35 – Hiring employees