Inventing the tweetroll

2 min readNov 5, 2015

I don’t know if Jonathan and I really did but it’s been fun. Alternatively named the tweeTroll.

It’s a fun way to poke fun at your friends on Twitter. All you have to do is efficiently dig up tweets from way back when. We’re talking years. ’08, ’09 and 2010 were fertile ground.

Keep your friends honest

Summer 2012

Not too shabby for the Gram.

Keep yourself honest

Summer 2010.

Five years later, Square is positioned to IPO.

Bring the cool kids back to a distant time

Nowadays when a successful entrepreneur, investor or [insert anyone popular] tweets, they’ve got a instantaneous flurry of RTs, favorites and replies. But! before Twitter was a thing and before they had any sort of fame or success, they too were like us tweeting out into the ether with very few listening and little to no engagement which some of us have found hilarous.

The first rule of tweetrolling is to find something older than three years old that hasn’t been touched by anyone.

Jonathan and I thought it would be fun to coordinate.

Summer 2009

Nice recommendations 6 years later.

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Cold Boston 2011 winter

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Fall of 2010

Mike needs the new apps…

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2007

Living in the past Ryan.

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2010.

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This was a good one. Stewart was between Flickr and Tiny Speck.

We know Stewart is busy running Slack but would’ve thought he’d stay up to date with the trends.

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Longtime obsession with notebooks.

Turn the tables

2009.

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Getting trolled with a tweetroll is pretty funny, thanks Zach Hamed (15x later).

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Whatever I can do to help Dave.

See you in the archives! Teaching people how to tweet since 2009 and tweetrolling since the summer of 2015. — @ryandawdjan

Be sure to explore Hear and Now —a recently launched Twitter onboarding service for business executives.

I forgot to mention

When you use the Twitter quote function, there is no timestamp displayed with the original tweet so this makes using old ones pretty interesting.