Possibility vs. Probability

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Jackie Summers talks about entrepreneur’s own special blend of risk tolerance that creates the unpredictable, terrifying and euphoric environment of a start-up.

Be Prepared

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“Luck,” says Jackie Summers, “must be courted.”

The Agency Review

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If accounts can go up for review, why can’t our relationships?

You’ve Got to Be Carefully Taught

Racist Eggs

Jackie Summers suggests we “teach the teachable” when it comes to equality.

The Passion

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Jackie Summers looks at the intersection of passion, timing and luck, from his view on the front lines of entrepreneurship.

The 911 Call: Screams for Help, Gunshots. Is This Justice?

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Zimmerman’s response, as he ignores law enforcement: “these assholes always get away.”

Bryan Stevenson On The Power of Identity

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Jackie Summers shares a moving TED video by the founder of the Equal Justice Initiative, who wants us to know that we can help change the world by building a healthy, strong identity and reconciling with our past.

The Disconnect

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Jackie Summers argues that when you’re a CEO, reality is never what other people believe it is.

Shoot First, Ask Later? Unarmed Boy Shot By Neighborhood Watch

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Jackie Summers decries the death of an unarmed teenager at the hands of a neighborhood watch captain who still walks free.

Surmountable

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Jackie Summers is starting a business from scratch. Here’s how he views the very large, daunting, and quite possibly impossible task ahead.

The Case Against Settling

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Jackie Summers would rather be alone than with someone who is not right for him. Still, he wonders.

Solitude: the Successful Black Man

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There’s a plethora of educated, successful, hard-working family men who happen to be black, writes Jackie Summers. So why is it that no one sees them?

Black Boy in a White Land

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Jackie Summers realized he was black, he found an elephant in the room wherever he went.

The Fakir

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Jackie Summers offers inspiring Valentine’s Day advice for would-be Cupids.

The ‘Check Please’ Moment

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He may be a dating expert, but on one first date, Jackie Summers discovered that there is only so much sh*t he can take.

Gender Bender: My Day as a Woman

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“If you wake up at a different time, in a different place, could you wake up as a different person?” — Tyler Durden, Fight Club