How I Did It: Need Supply Co.’s CEO Spent Two Months on Wall Street, Then Started a Millennial Fashion Cult

(In its series “How I Did It,” FN profiles successful footwear and fashion players — from entrepreneurs to designers to top executives at major brands — and reveals how they carved their path into the industry.)

When Chris Bossola put $1,500 worth of vintage Levi’s on his credit card in 1996 to open a 200-square-foot boutique in Richmond, Va., there was a lot riding on it.

His wife was making her way through law school, and Bossola had recently walked away from a short-lived career in corporate finance.

“I was a trader on the Nasdaq for literally a couple months,” the now-retail maven said of his earlier career ambitions. “I hated it. I always had an entrepreneurial spirit.”

Now, more than two decades since he started Need Supply Co., the single store in Richmond has grown to include two robust e-commerce platforms — Needsupply.com and Totokaelo.com — as well as physical outposts in Seattle, Japan and New York under the Need Supply Co. and Totokaelo banners. It currently boasts a presence in 75 countries and employs around 150 people worldwide. (Need Supply Co. merged with luxury retailer Totokaelo in 2017.)

To boot, the company, known for its high curation, buzzy sneaker drops and elevated brand storytelling, is widely considered a fashion and culture authority for millennials and Gen Z.

Here’s how Bossola did it.

Need Supply Co founder Chris bossola
Chris Bossola, founder and CEO of Need Supply Co.
CREDIT: Courtesy

How did you become interested in fashion and retail after you left finance?

“When I was [growing up], I wanted to be an investment banker, but I didn’t have the grades, so I became a trader, and I hated it. I think I ultimately wanted to be an entrepreneur — I just didn’t realize it. After I left [Wall Street], I started a couple of other small businesses that ran their course or were deal-oriented. I didn’t see that they had sustainability in the sense that they could grow and evolve into a larger business. [When I started Need Supply Co.], I got the feeling was that I no longer had a job but I was doing something I was interested in, enjoyed and had fun with.”

What was the biggest sacrifice you made during the early days?

“The difference [between] having a job versus running your own business is, you don’t have time off — especially in the beginning. There’s always more that can be done; it can always be pushed further. It’s a sacrifice of your attention and focus — but well worth it. It’s 100 percent when you have your own business.”

When did you realize Need Supply had grown outside of its hometown in a major way?

“We had a customer walk through the front door of the Richmond store and say to me, ‘I’m from New York and just moved to Richmond, and I didn’t realize there was a Need Supply Co. here.’ [Meanwhile], this is our flagship headquarters.”

need supply co
A campaign image for Need Supply Co.
CREDIT: Courtesy

How did you gain the confidence to forge new deals and expand Need Supply Co.?

“I always keep my eyes open for opportunities. I get excited about potential deals and opportunities that are a win-win. [For example], our partnership in Japan started because someone — a Japanese publisher — emailed us and said that they wanted to print our Need Supply Co. journal we created in-house in Japanese and distribute it around Japan. I said, ‘Let me see that email!’ That turned into a longer partnership, which then turned into retail stores. Each of the different things we’ve done have come about that way — by leaving ourselves open.”

Describe your biggest disappointment.

“We had a store in Athens, Ga., that opened in 1999 and closed in 2001. It was a disappointment. but it taught us that we could have a setback like that and recover and move forward. The secret to business is not thriving during the good times but surviving the tough times. It’s a matter of grit and maybe a little bit of crazy optimism.”

What’s one thing you do every day to be successful?

“Prioritize. That’s a skill I developed running a company. Whether it’s money, product or people — the resources are always limited. So you have to, as [Facebook COO] Sheryl Sandberg says, ‘ruthlessly prioritize’ to be successful and continue to leverage the right resources for the right things.”

What is your best advice for entrepreneurs looking to get into retail?

“It’s probably the same [for any industry]: The best thing to do is jump off the proverbial bridge. There are those who don’t — but those who do, figure out how to swim when they hit the water.”

need supply clothing shoes
A campaign image for Need Supply Co.
CREDIT: Courtesy

The next big thing in retail is …?

“I don’t know exactly what it will be, but the merging of physical and digital is going to change the face of retail. Obviously, it’s already happening, but we’re just at the beginning of it.”

What’s next for Need Supply Co.?

“One of the big initiatives for us is to grow our private brands — we have six. But this year we’re launching shoes — a summer ’19 capsule collection.”

Want More?

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How I Did It: An Entrepreneur Who Turned Her Home Into a Shoe Warehouse to Build Her Brand

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