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Travelogue - The Pluralsight IPO

Wednesday, May 22, 2019

I have a difficult time stating that I left London early to reach New York City in time for a pre-IPO party without laughing at the gaudiness of it all. However, that’s what I did just over one year ago.

My Pluralsight story begins at a Visual Studio Live! Conference in 2007 when I met Fritz Onion in a speaker’s prep room. Fritz knew me from writing and blogging, and, eventually, our first meeting led me doing a "test teach" for Pluralsight.

A "test teach" is a short tryout involving real students, but it was more than just a check on my speaking ability. I believe the "test teach" evaluated several soft attributes. Could I build a rapport with the students? Do I handle questions well? Can I socialize at lunchtime? Can I successfully arrange and coordinate travel on my own to reach the customer? It’s one thing to plan a trip to visit a tourist attraction where signs and strangers would help you along the way. Planning a trip to arrive at a nondescript office building in a generic business park of Jersey City at a very specific time requires more expertise [1].

The test teach went well, and now I'm on a plane into Newark. Over the last 10 years I've taught dozens and dozens of classes all around the world for Pluralsight. I've made over 50 video courses for Pluralsight.com. The company is ready to go public, and I've been invited to the opening bell ceremony!

The Arrival

I’ve never been on a car ride into the city. I’ve always arrived on a plane, or underground on a train. But on this trip, I arranged for a driver to take me from Newark Airport to the W hotel in Times Square. It was my first time in a car through the Holland tunnel, and with all the traffic into the city at 7 pm, I had plenty of time to study the tunnel. The night was dark, wet, and foggy. New York had put on its Gotham city look, and I was waiting for the Batmobile to zoom past using an invisible traffic lane.

Arriving in Gotham

The pre-IPO dinner party was at Estiatorio Milos, a Greek seafood restaurant on 55th street. Milo’s food was okay. The place had the feel of an upscale restaurant designed to extract as much coin as possible from patrons while giving those same patrons the ability to brag to everyone about eating fish flown in fresh from the Mediterranean. Form over function. The company and festive atmosphere were better than the food. I joined late but found a seat among other authors, including Joe Eames, Deborah Kurata, and John Sonmez. Although there was talk of an after-party involving an ultimate milkshake, being on UK time, I needed sleep before the big morning.

Milo's Food Offering


Times Square in New York is an astounding place. Bright lights, tall buildings, and a mass of humanity moving through the streets. The ads are so intense they lead to sensory overload. There are animated ads for movies, which want to take your money in exchange for laughs. A four-story jewelry ad wants you to trade money for diamonds. Underwear, outerwear, phones, hotels, and banks all project images in a quest for branding and customers.

Times Square from a Distance

There was a time when I would have dismissed the square as being too artificial. But, after reading A Splendid Exchange, I’m seeing Times Square as a primal center of trade, and a natural expression of what humans have been doing for centuries. It is the place where humans come to make exchanges.

The Peak of Civilization

When we leave the hotel the morning of the IPO, the exchange we are looking for is the NASDAQ exchange on 4 Times Square. The NASDAQ is hard to miss thanks to the 7-story curved LED display outside. In fact, this NASDAQ location is really more of a media center than an exchange. The place has television studios inside, and rooms with hundreds of cameras where companies doing an IPO can ring the opening bell and look like they are on the trading floor surrounded by “traders” working diligently in front of computer monitors. The physical NASDAQ trading market exists only in silicon and fiber optics.

I’m one of only six or so authors who’ve been invited to be present for the IPO. There is also 50 or more Pluralsight employees, board members, and investors. A few of the people I’ve known for years and grown fond of. But with Pluralsight’s rapid growth, the majority are strangers to me. Nevertheless, we are bonding together like molecules in a high-energy physics experiment. I’m barely through the security entrance when Gene Simmons walks out of a TV studiio. He saunters over to 4 of us gawkers and in a Gene voice says, "So ... what are you gentlemen here to sell today?"

Me and Gene Simmons

You’ve never felt like a true nerd until you tell Gene Simmons about your training videos covering software development. It is impossible to perform this task without sounding like the D&D dungeon master at the corner table of a comic book store.

It Happens Quickly

During an IPO, there are two significant moments. The first moment is the opening bell ceremony. Not every company will choose to participate in the ceremony, but I'm glad Pluralsight did. For this ceremony, everyone gathers on the stage in a circular room. In the room there are dozens of electronic displays hanging from the wall, and even more cameras. The cameras cover every possible vantage point on the stage. There’s a podium on the stage, and NASDAQ people walking around wearing headsets, carrying clipboards, and giving orders with all the authority of a television producer. In the moments leading up to the 9:30 am market opening, they are giving us pep talks and telling us the more we clap and yell, the better we'll look on TV. I'm a bit worried that if we manage to add more energy to the room, we will start a chemical reaction that lays waste to the entire building.

The NASDAQ Media Room

At 9:30 am, the person at the podium (Aaron, in this case), takes a cue, pushes a button, and the bell rings. Confetti begins to fall. There’s yelling, clapping, and arm raising. I think of my parents. I wish they were still alive to see this moment. I’m one parental memory away from losing it and crying all over the stage. I can’t ever remember euphoria and sadness being mixed like this.

After the opening, there is professional picture taking, both inside the building, and outside in Times Square. There's also champagne, and singing and laughing, and selfies. Lots of selfies.

Ring the Bell!

The next big moment on IPO day comes when the first share of stock is publicly traded. I don’t remember the precise moment when this happened, but I think it was about an hour or 90 minutes later. There’s a roar when the price of the first trade execution hits the screens. There’s hugging, handshakes, and back-slapping. More selfies, lots of selfies.

First Trade Executed!

And then ... dispersion.

We leave the studios and head back to the hotel. Most Pluralsight employees are flying out in the afternoon to be back in Utah the same day. I’m beginning to think that if my driver can come early, I’ll get through the tunnel before rush hour hits and catch an earlier flight home. Flights between D.C. and Newark go once an hour when the schedules are working. If I can't catch an earlier flight, maybe I'll take the train. Either way, it’s not even lunchtime and I’m exhausted.

In the end, I did catch an early flight. However, before I left, I had a quiet celebration with a meal worthy of a billion-dollar IPO. I had a $5 hot pastrami sandwich from a street vendor two blocks from Times Square.

Function over form.

[1] Years ago, a renowned training company approached me about teaching a Web API class at Microsoft. For my first class, I was given a location on the Microsoft campus and told a Microsoft employee would be there to let me in the classroom. I arrived 30 minutes early and began waiting for my Microsoft escort to arrive. With 15 minutes left before the class started, I started emailing and trying to reach people at the training company to let them know my escort wasn't arriving. The classroom was in a locked down section of the building, and I wasn't getting past the entrance without my escort.

Finally, as my escort arrived 2 minutes before the class began, I entered the room in a state of panic. As I was setting up, I noticed that one of the well known instructors from the training company was sitting in the front row of the class. He was directly in front of my podium, and I heard him say, into his phone, "looks like he finally made it." I didn’t have time to think much of the statement at the time, as I only wanted to get plugged in and take a couple of deep breaths before launching into an all-day technical workshop for 70 MS engineers.

Later, when I replayed the opening events in my mind, I was furious. Why didn’t someone let me know he’d be there? Why did no one respond to my calls? Why couldn’t he provide me with an escort? After that experience, I think I finished one or two more classes for this training company that we had already arranged, and then I let the relationship expire quietly.

I tell this story because Pluralsight has always treated me with respect, and that's one reason I've been loyal and stuck with them.