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.