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CEO Jason Robins: "DraftKings Inc. Didn’t Come About on the First Try, or Even the Second or Third"

Written by:
Alejandro Botticelli
Published on:
Aug/11/2022

In an incredibly candid post on LinkedIn Thursday, DraftKings CEO admitted that the company took some time to come to fruition.

Jason Robins founded DraftKings nearly a decade ago as a Daily Fantasy Sports concept that quickly exploded along side its Dublin, Ireland rival FanDuel.

"I first got the entrepreneurial bug in college while studying at Duke University. It was the height of the first tech boom and there were tons of new companies at the career fair on campus. All these businesses had raised hundreds of millions of dollars — everyone was excited. 
 
"I remember talking to my father and telling him I was going to drop out of school and head to Silicon Valley to join the tech rush. Thankfully, he instilled the fear of God in me -- not six months later, the bubble burst. The next career fair? None of those companies were back."

Some time later, Gambling911 readers might recall those Vistaprint commercials that used to air incessantly a few years back.  That's where Robins got his start. Janet Holian ranked above him there but she would ultimately be lured to DraftKings and handled much of their gorilla marketing starting in 2015.

Hollan believes the DraftKings DNA can be found in Vistaprint.

“Where I see the commonalities (with DraftKings) are I think some of the values are similar,” Holian noted in explaining how DraftKings has evolved from Vistaprint business notions as part of an interview with Bostinno.  “The fact that it’s very analytically driven. And that goes back to before Vistaprint, because Jason and Matt are from Capital One. And Paul is analytical by nature.”

While at Vistaprint, Robins oversaw the company’s first broadcast campaign.  It was a major success, but Hollan never saw Robins starting his own company.

“I will say it was a miss for me.  I’ve even talked to the CEO of Vistaprint about Jason to say ‘how’d we miss him?’”

It was another Vistaprint executive, Matt Kalish, who apparently gave Robins the inspiration for DraftKings. 

"We started to get the bug again and had many sleepless nights batting ideas back and forth," Robins revealed via LinkedIn.  "We must’ve come up with hundreds of ideas, until one night after work Matt sat me down and explained the premise of what would become DraftKings.
 
"It took me all of two minutes to realize, 'This is it. This is the one'.” 

Kalish helped co-found DraftKings and now serves as its President.
 
"Everything I went through led me to exactly where I needed to be, when I needed to be there. The lessons I learned in those earlier years prepared me to lead when the time came. 
 
"You never know when the idea that will change your life might strike. But when it does – be ready for it."

This particular week will mark one of the most pivotal in DraftKings young history.  Its home state of Massachusetts finally passed legislation (signed into law by the Governor Wednesday) that will finally allow DraftKings to operate in a regulated environment there.

- Alejandro Botticelli, Gambling911.com

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