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Jason Calacanis, CEO of Mahalo.com

Jason Calacas, CEO of Mahalo.com and the host of “This Week in Start-Ups,” discusses his strategies on how innovators and entrepreneurs can keep their competitive edge in a world that will constantly challenge them. 
Citing his own successes as coming from, how he, “Pick[s] new technology and apply it to old products,” he admits that entrepreneurs must be ready to fail when the try to make their ideas into reality. He recommends hard work as the only way an entrepreneur can weigh the deck in their own favor: “If you work hard, you’re going to win more than you lose.”

Why an entrepreneur?

Calacas talks about the ways in which he finds rewards in his challenging career path. The connections and teams that he builds, and the social bonds those engender, are parts of the day-to-day of his job that he loves. Of course, he cites fundraising successes and the sale of a previous company as highlights in his career.

Inspired by risktakers

Calacas’ career describes someone who values those who can accurately access risk – and then take those risks that offer the possibility of a big pay-off. He talks about how Lenny Bruce and Bob Dylan, both artists who he considers risk takers, tried something different from what the mainstream understood. Even when entrepreneurs fail, Calacas says, they should continue to learn about how to work through iterations of their ideas; eventually they may discover the missing piece that enables them to make an idea a success.

“As you become older it becomes not about winning, but more about the effort you put into it…I focus on trying to do a little bit better every day.”

Being realistic about your chances

While his belief in taking risk is well-established, it’s Calacas’ call for realism from prospective entrepreneurs that acolytes should attend to. With no guarantee of success, the need for strategy and good execution fall on the head of the entrepreneur trying to sell his or her product. While the market will sometimes present insurmountable obstacles to success, working hard and having a good strategy can minimize those risks.


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