When Starting Up, 'Ask Tons of Questions' and Figure Everything Out Along the Way For the founders of clothing company Vineyard Vines, the early business strategy was to wing it.

Sometimes, too much planning isn't a good thing. Take it from Shep and Ian Murray, co-founders of lifestyle and apparel brand Vineyard Vines.

In the late 1990s, the brothers from Connecticut both commuted to Manhattan each day to cut their teeth on entry-level jobs at challenging finance companies. Like many entrepreneurs, the brothers eventually tired of the commute and the 9-to-5 set to follow their dreams of starting something on their own.

And so Vineyard Vines was born. Initially selling ties with prints that reminded the brothers of "the good life" on Martha's Vineyard in Massachusetts, the company has grown to more than 70 retail stores across the U.S.. While, in the beginning, the Murray brothers didn't know much about starting a clothing business, they pushed ahead, learning everything as they went along.

To see how the Murrays managed to build a clothing empire by "asking tons of questions," check out the video above.

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