For the last nine months, Deeming has been spending time in the U.K. where he's working with a team of seven to launch Jetsetter's first international site. He expects to stay at Jetsetter U.K. until he gets the business off the ground before turning it over to a senior manager.

Deeming is also working on several top-secret projects and re-launches of existing sites which will be announced in 2012.

"It's exciting to always be working on news things, but it's also challenging to build a business and then leave it to someone else to run," he said. "It feels like letting go of a baby."

Growing too Fast?

While Deeming said he feels confident Gilt isn't stretching itself too thin through aggressive expansion, the company has scaled back launching new businesses this past year to ensure it can dedicate enough resources to its different sites.

"Growing fast is always a concern but not growing fast is a concern too," CEO Ryan said. "There are lots of things we haven't done -- we haven't expanded into 20 countries and we're not in 100 different categories."

And as retailers are becoming smarter about cutting back on ordering excess goods that Gilt relies on to supply its inventory, the company will continue to break into other areas to sustain its growth, said Gene Alvarez, an analyst with Gartner.

"Gilt needs to look at new opportunities when you see the core business seemingly maturing," added Forrester analyst Sucharita Mulpuru. "Growing into these other businesses can mitigate the negative affect of not having as much inventory there."

For Deeming, he sees Gilt continuing to push new businesses forward, one of which he hopes to build from the ground up and then run full-time eventually.

"I'm not ready to give up the fast paced build-it life yet," he said.

-- Written by Olivia Oran in New York.

>To follow the writer on Twitter, go to

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