My mom has never logged on to the world wide web, so it’s not fun to talk about her.

But…this scathing photo has now surfaced and I feel it’s time.

I know what you are all thinking, but NO it’s not me on the right….that’s me on the LEFT!

Ok I kid. It is me on the RIGHT and that kid next to me is Randy Rosenberg who introduced me to poker (but never called me to invest in $ZNGA) and actually married the sister of Jackie, the girl in the photo. Small world.

Back to mom. What kind of mother sends her kid out into the world like this?

I was a shy kid and I know this because that’s how I felt and remember it very strongly. If I had not attended the wimpy Jewish day school, I would have been beaten senseless every day of my young life. This picture just reminds me how much confidence I really would have needed as the clothing (I was wearing Yoga pants before anyone had heard the word $LULU) and shoes stacked the odds highly against me.

The whole thing has got me rethinking Facebook and the Timeline. I like it in a new and different way. It’s fun to be surprised by a random photo sent by an old friend completely out of left field. Now, I wish I had more. My son Max sees me in a different light and even himself.

Digital publishing, photos, smartphones, email and the social web are impossible to value now that there is momentum and scale. It is now the shortsellers and naysayers that are being beaten senseless everyday, not the insecure nerds like me.