Jack Dorsey's Hardest Job

Jack Dorsey has had a lot of difficult jobs. As the co-founder of Twitter, Dorsey helped build a company that has become the world's second-largest social media site. When he returned to the company as its Chairman, he faced the challenge of taking Twitter to the next level as it attempted to raise revenue. Now that Twitter is preparing for its IPO, Dorsey is bound to endure a whole host of new challenges. As the co-founder of Square, Dorsey participated in the creation of one of the fastest-growing mobile payment companies in the world. Square's product -- a small, square-shaped credit card reader -- may have instantly appealed to tech-savvy merchants who were already craving a mobile payments solution. Even so, it couldn't have been easy to gain the support of a massive coffee chain like Starbucks SBUX. But Dorsey and Square made it happen. Related: What's Twitter And Square Founder Jack Dorsey's Favorite New App? Having accomplished so much, you might think that Dorsey's hardest jobs are behind him. In reality, his most difficult job is ongoing and never-ending. "I think the hardest job [is] to add to the team constantly," Dorsey told Benzinga. "To bring the right people into the company but also part ways with ones who don't make sense -- that's probably the hardest thing for any startup to do, to let go of people." Dorsey said that bad relationships -- personal or professional -- should be ended quickly. "If a relationship is not great, you can let it linger or do the right thing and part ways," Dorsey explained. "It's better for both of us," Disclosure: At the time of this writing, Louis Bedigian had no position in the equities mentioned in this report. Louis Bedigian is the Senior Tech Analyst and Features Writer of Benzinga. You can reach him at louis(at)benzingapro(dot)com. Follow him @LouisBedigianBZ