TweetItForward: Doing Good Personally and Socially

Get an envelope with $500 in cash wrapped in a social incentive to do something with it that makes a difference. Take action based on one’s own definition of “difference” and then write about it. Piece of cake, right? If only.

Nicole Mastrangelo, Neil Glassman, Cary Chessick

Under ordinary circumstances, I’m not a facile writer. I’ve gotten quite used to staring at a few disjoint sentences on my screen waiting for inspiration.

My difficulty writing this post was compounded by two factors that guaranteed I’d have writer’s block. Bad writer’s block. The first is a sense of obligation. Not that having to do something is inherently bad, but it has a way of freezing my fingers. The second is writing about writers. Though I’ve been told I write well, I have deep envy for great writers and fear they will judge my writing poorly.

Perhaps I best start at the beginning. Before the blood gushed out of my left hand. It started with an envelope with $500 in cash.

Another day, another social media conference

Carrie Kerpen and Dave Kerpen invited me to attend their Likeable University on June 6. With more than a bit of tweeting, I shared the knowledge and diversity of the speakers and participants. The formal program concluded with a keynote from Cary Chessick, CEO of

Those of us in social media hear daily about the importance of transparency and honesty. In his keynote [full video here], Cary revealed not just his life story, but the emotions and motivations that brought him to this point in his life. He shared successes and failures, as well as how helping others is a profound part of his daily activities. I’d never before met someone who shared so deeply with a room full of strangers.

Then came a surprise finish. From the press release: CEO Cary Chessick gave away $20,000 in cash to 40 random attendees at a social media conference. Chessick’s celebration, called TweetItForward, was unveiled during Internet Week New York at the inaugural Likeable U: The Social Media Movement, attended by thought leaders and industry experts. He shared his experiences about the value in the gift of giving before each randomly chosen guest was presented with $500.

The concept of “pay it forward” is rooted in the idea of helping others without expectation of anything in return, and Chessick’s celebration is the social media version. He and his wife donated personal money for the giving effort.

“I’ve been fortunate to experience the gift of giving,” said Chessick. “It’s my belief that a simple act of giving can change a life, alter a person’s path and create new social connections. It can bring together friends and family in a way that is unique, and ultimately increase happiness in both the giver and the gift recipient.”

Chessick passed out envelopes to 40 unsuspecting attendees at the conference. The envelopes contained one $100 bill, four $50 bills, five $20 bills and ten $10 bills for a total of $500 per attendee.

Chessick’s surprise $20,000 gift to 40 people was without any ground rules or restrictions. His message to the conference attendees dealt only with achieving happiness and impacting the lives of others in a positive way. The fortunate 40 were thrilled with the unexpected gift and all the possibilities.

“I was just shell-shocked. I was holding the envelope and then I put it down on my desk at home,” said Neil Glassman, a marketing strategist. “I don’t know if I should operate impulsively or just give it some thought for a few days about how I want to pass that goodness along.”

Yeah, the press release continues with other quotes, but mine was first. And I was in the recap video.


Random acts of kindness towards strangers.

How cool is that?

After a few days, I tossed ideas around in my head as the envelope of cash stared at me from its place on my desk. Then I got a phone call from my friend, Cynthia Heimel.

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