My Weirdest Work Experiences

If you count a college summer job (for which I worked on, no joke, a non-porn site called Pork Central), I’ve been working professionally on the web and web-adjacent stuff for 25 years now. 💀

As you might imagine, I’ve seen some things in my tour of duty, so I thought I’d round up a few of the most surreal highlights:

  • Meeting up with a bigshot in New York only to have him force me to sit in silence while he re-arranged the icons on his desktop for an excruciating amount of time before allowing the conversation to begin.

  • Recording a video interview with the great Michael McKean, only to watch in horror as the camera ate the tape and rendered the whole thing useless (while he was still standing in front of me).

  • Getting on a private jet (my first and only time doing so) with our company co-founders for a last-minute meeting with 50 Cent’s inner circle.

  • Interviewing at a company that I wasn’t fully sold on, but having them end the interview by taking my corporate headshots and including me in their latest team photos. I did not take the job.

  • Watching Richard Branson “fly” a fake jetpack through a Virgin Megastore. See above.

  • Giving a test iOS device to a co-founder’s brother, only to get it back with the camera roll jam-packed with photos of him shirtless.

  • Being summoned to an all-hands in which the CEO (famous for wearing a pink pocket square) announced new corporate branding by dramatically switching to a black pocket square.

  • Waiting for my flight up north to meet with our small-ish company’s CEO, then seeing her on the cover of Fast Company magazine while browsing around at the airport bookstore.

  • Watching Blazing Saddles at a (now) billionaire’s house.

  • Meeting and discussing website concepts with Cindy Crawford.

  • Sneaking onto a reality show set in an attempt to obtain exclusive website footage by awkwardly hiding a camcorder in my jacket sleeve.

  • Following the announcement and launch of the iPad from Punky Brewster’s house.

  • Looking up from my desk to see Jeff Bezos walk by (right around the time that the Lauren Sanchez news broke).

  • Having to watch a group of engineers do a team building exercise that involved writing goals on paper airplanes and throwing them from a balcony.

  • Working with a great guy on our customer advocacy team that left to pursue his dream of becoming a standup comedian. Mission accomplished, Hasan.

FOX Reality of My Youth

Back in another life, I worked on the websites for various primetime FOX offerings. While I got to work on some still-beloved classics like The X-Files, Firefly and Greg The Bunny, I also spent a good deal of time on some absolutely mind-melting reality shows and specials.

Since I think we could all use a bit of a distraction right now, here’s a roundup of a few of the “best” selections, may they never fade from our collective memories:

Joe Millionaire

He walked through the office once, and it was quite the event. My favorite part is that everyone wildly speculated about how they’d trick people again for the second season, and the answer was “yeah, we’ll just do it in Europe.”

Man vs. Beast

To this day, I still bring up the hot dog-eating bear to new co-workers. It’s honestly pretty central to my core identity at this point.

Mr. Personality

A true pioneer in the “make them wear masks before agreeing to bang” genre. Hosted by Monica Lewinsky, who I unfortunately did not get to meet when I visited the sweet mansion in Malibu. Sadly, I also think that this (surely invaluable) Cheat Sheet is lost to time:

My Big Fat Obnoxious Fiance

Let’s be real for a sec, our belt buckle-centric landing page was groundbreaking stuff:

Celebrity Boxing

Interviewing Joey Buttafuoco and Vanilla Ice on the same day remains a “highlight” of my career.

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The Tens

A decade ago I wrote up a short recap of some major events that’d happened to me over the previous ten years. Let’s do it again!

Some notable things that’ve happened to me since January 1, 2010:

  • Amazingly, didn’t have any more kids (went a wee bit overboard in the previous decade)

  • Left Ning for a job at Moonfrye

  • Left Camera IQ for a job at Ring

  • Proudly watched my wife go back to (and thrive at) teaching

  • Said goodbye to our first family dog, then went out and got the one owned by Charlotte from Sex and the City

  • Became a battle-hardened veteran of the parental controls/gaming device setup wars

  • Became much more open about my faith (and the ongoing struggles I’ve had over the past several years)

  • Watched my music and movie collection turn from files on a hard drive to files on various cloud services

  • Took some big steps in my longtime mental health journey (perhaps a topic I’ll address more publicly over the next ten years)