Why Fund-Raising Proved Difficult for Jack Dorsey's Start-Up

When Jack Dorsey hit the fund-raising trail last year for his most recent start-up, Square Inc., he had no trouble finding venture capitalists to take him to lunch.

After all, he co-founded one of the most buzzed-about Web start-ups, Twitter Inc., so investors wanted in on Dorsey’s next idea.

That sounds great to most entrepreneurs, but Dorsey said that made things difficult. As he took investor meetings in both Silicon Valley and New York–25 in a two week period–he kept walking away with the same question.

“Were they interested in [my] background or the business?” Dorsey said Wednesday at the TechCrunch Disrupt conference in New York.

Perhaps differing from some of the other young companies out raising capital, Dorsey said he welcomed a negative response.

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