Thursday, October 1, 2009

Top Five Thursday: Most Likely to Succeed


I'm not exactly successful by conventional standards. I mean, I earn less money now than I did three years ago... is taking a pay cut to sate your idealist nature one of the Seven Habits of Highly Effective People? I can't imagine it is! But, by my own standards, I consider myself a success. I've been played on the radio. I've been published. I found love. I live by the ocean! These were all on the Master List. And if you had told me in college that one day I'd refuse offers of hundreds of dollars to play on St. Patrick's Day? I'd have flipped out.

However, I have some truly amazing friends — inspiring people who are successful not just by my standards, but by the rest of the world's, too. There are many more that deserve mention, but for now, here are my...

Top Five Most Successful Friends:

5. Andrea Tompkins
Not long ago, Andrea was just like you or me, working away at a nonprofit in Boston. Then she went to law school in D.C., whence she landed a crazy-ass internship at a firm in London — that paid more than my last two jobs combined (yep, internship). Said firm not only hired her on full-time this year, but paid for her to move to London, paid for a temporary flat, and of course took care of all her visa stuff. And while studying for the bar exam this summer, she also managed to, y'know, travel to Southeast Asia and Japan and attend a wedding in Prague. That, my friends, is success!

4. Sarah Kucserka
Sarah went to Syracuse with us, but hated all of our sports teams (and graduated early, I think just to spite the Orange!). After graduation, she made a name for herself in L.A., eventually landing a gig writing for ABC's Ugly Betty. How awesome is that? Now she's distorting impressionable young minds, writing for the racy, Gossip Girl-esque web series Private, based on the best-selling teen novels. I'll confess, I haven't actually watched it yet (mostly because I'm not a 13-year-old girl).

3. Meredith Goldstein
A longtime arts and entertainment writer for the Boston Globe, Meredith has interviewed just about every movie star who's passed through Boston. Then, last year she got tapped to write Love Letters, a Boston.com blog that takes the old daily advice column into the 21st century... and it blew up big-time. What's more, she gives really good advice!

2. Will Dailey
My good friend Will is one of the finest songwriters I've ever met or, frankly, heard. He worked his butt off for years — now he's finally getting national attention, playing music for a living — even getting free guitars, amps, and other gear just for being him. He's performed on CSI:NY, the Early Show, and (below) the Late Late Show with Craig Ferguson:



He's yet to make the jump to lightspeed, so to speak. But who knows, he could potentially even eclipse our #1 (in fact he already tops this list in Googlefight).

1. Dennis Crowley
Still, there's a fair chance that my friend Dens might one day run Google. Our senior year roommate was always the smart, ambitious type. He transformed our (eventually-condemned) party house into a Saturday night money machine. He created a social networking site that incorporated mobile phones — years before Twitter — and sold it to Google. His latest creation, the iPhone app Foursquare, is quickly catching on. Every now and then, I randomly find a story about him in the New York Times; he even has his own tag on Gawker. It runs in the family, too: last year the Crowleys spent three days reigning Family Feud. In short, Dens is the most outrageously successful person I know!

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