Bill McCloskey

Serial Entrepreneur
6 minutes reading time (1255 words)

Failure (Part 2): Dreamland

This week, Bill continues the story of his biggest failure.


“In Dreamland we trace the life of our protagonist, Chad Holloway, from birth to his apparent suicide at the wheel of a high performance sports car. Like a jigsaw puzzle, the player constructs the arc of Chad’s life: the mystery surrounding his birth, his rise to political power and his eventual tragic fall, and the source of the terrible guilt that has driven him to despair. These events unfold against the backdrop of an abandoned amusement park which is governed by a strange and enigmatic caretaker named Virgil. “

“ The events of Chad’s life, outlined below are revealed to us as fragmented memories. These memories appear in the form of video sequences, photo albums, disembodied conversations, recordings, newspaper clippings, letters, and other mnemonic devices that are discovered, via the game-play, scattered throughout the amusement park of Dreamland.”

So began the 100 page package we created for Microsoft, including a 50 page script, dozens of detailed drawings, and all the game play outlined.

The four members of Quartet rented some offices above a real estate office where we would meet each day to develop the game. Tim Gavin set up a drafting table and began producing these large, intricate drawings. Each day we could see the script we were creating take life on Tim’s table. Paul had set up a studio nearby and was creating an entire score for the game. He’d drop by with the latest musical theme for us to listen to while we played the current crop of computer games to check on the competition.

And watching Kristi was like attending a graduate course in filmmaking. When we weren’t working on the script, she would be on the phone chatting with famous producers and directors like they were her best friends, which they often were.

We flew out to Los Angeles to meet with the Microsoft team at the Digital Domain offices.  The meetings went great, Microsoft is excited, Digital Domain is excited. The lead developers at Digital Domain are telling me it is the best game script they’d ever seen. Soon, we are having lunch in Santa Monica and in restaurants with giant Jonathan Borofsky clown heads over their front door.

Somewhere we run into Scott Ross, who along with James Cameron had founded Digital Domain, and he was sporting a huge cigar. “Everyone loves Dreamland,” he tells me. We leave LA thrilled.

Back in New York, we hear through our agent that Microsoft wants to move to the next stage. They want to sign a development deal and hand us a six figure check. We are to fly out to Redmond, WA the next weekend and sign the papers.

Strike One

Sometimes you can do everything right and still fail. Sometimes there are just things that happened that could not be predicted. On October 12, 1994 Steven Spielberg, David Geffen, and Jeffrey Katzenberg formed Dreamworks. It would be months before I realized the significance of that date, but by then it would be too late.

A few days before we are to fly to Microsoft, our agent calls. The meeting has been postponed for a week. It turns out Spielberg, Geffen, and Katzenberg were flying in to meet with the Microsoft Games division and our contacts there.
“Should we be concerned?, “ I asked my agent?
“Not at all, “ was the reply.

Nobody Knows you, when you are down and out.  

We didn’t hear from our agent for a while despite our attempts to reach her. When we finally reached her, the news wasn’t good. It turned out Dreamworks was there to do a deal. Even though they did not yet have a game division, they signed a deal to have Microsoft be the sole distributor of all future Dreamworks games. But, in exchange, Microsoft had to shut down their own games division!

Our deal was dead.

Strike Two

But all was not lost, or so said our agent. Microsoft was turning all of their projects over to Dreamworks and we were to meet the Dreamworks team at the very first E3 show, which had just taken over as the premier Games Trade Show. We sent over our package and it took them a while to find it in the mail room because they weren’t expecting a games proposal to include detailed 18x24 inch architectural drawings and a full score.

And for a while, things started to look like they could get back on track. We met with Sega and other games manufacturers and things began to look up. But then the Christmas sales numbers for the computer games market came out and they were beyond abysmal. It turned out, that no game, other than the top three, made money. Right then, the computer game market died. No one was going finance a million dollar computer game. No one.

Strike Three, You’re out.

In the meantime, I still had to produce something for the VC’s I’d met who were providing me “half salary” for the last six months. The project was doomed from the start but I went in and pitched them everything I could think of. They verbally agreed to keep financing me for a few more months, but they could read the games numbers as well as anyone else.

The date was October 3rd, 1995. Every avenue I’d tried had failed. The VC’s called and said we were parting company, and by the way, they weren’t going to pay me for the last few months.

The mother of my children is a 20 year cancer survivor. She told me about her newly diagnosed condition as I was hanging up the phone from the VC’s. I had planned to use the money to pay my health insurance. I had reached the lowest level of my life. No job, no money, no heath insurance, my wife diagnosed with a potentially fatal disease, a mortgage to pay, and two children under the age of 6. I was 41 years old and a complete failure.

In a state of shock, my wife and I turned on the TV to get our minds off of our world crumbling around us. We looked up at the TV screen:

OJ Simpson had just been acquitted.


The next day, things started to turn around. I got an offer to help on a game, the VC’s had a change of heart and paid me for the two months. I was able to pay for our health insurance and slowly I pieced together various revenue streams to keep my family afloat.

It would be another 5 years before I started another company, and six years before I would do it full time again. I’ve been at it ever since.

And Dreamland is still out there: every once and while I wonder how much of our original script got “borrowed” for someone else’s project.

The aftermath of failure is that I got up the next day, I dusted myself off, and I rebuilt my life. And it turned out, as it often does, that my Failure led me to my eventual Success. I went on to try and develop games on the web using VRML, an early rich media technology. That got me involved with digital advertising and started me on my career as a full time entrepreneur.

You may not know it at the time, but your biggest failure can lead to your greatest success. You just have to learn to keep playing the game.



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Sunday, 26 June 2022