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Friends,

DraftKings is one of the most valuable companies in sports. The daily fantasy sports and sports gambling company was founded in 2012 in Boston, Massachusetts.

The three co-founders — Jason Robins, Paul Liberman, and Matt Kalish — were all working for Boston-based Vistaprint at the time. But they loved playing fantasy sports, entering 200+ leagues each year and were frustrated with the idea that you had to wait until the end of the season to receive your payout as a winner.

So they started DraftKings, offering users the ability to play daily fantasy sports (DFS) competitions. The company then received an investment from Major League Baseball (MLB) in 2013, and DraftKings was handing out $50 million in prizes within two years.

Of course, the company has changed a lot over the last decade. When the US Supreme Court ruled PASPA unconstitutional in 2018, paving the way for individual states to legalize sports betting, DraftKings transformed itself into a sports gambling company.

DraftKings (High-Level) Timeline

• 2012: The company is founded by Jason Robins, Matt Kalish & Paul Liberman

• 2013: DraftKings receives investment from Major League Baseball

• 2014: The company reaches 50k active daily users & 1M registered players

• 2016: DraftKings & FanDeul agree to merch but later terminate the agreement

• 2018: DraftKings launches its first legal online sportsbook in New Jersey

• 2020: DraftKings becomes a public company at a $3.3 billion valuation

DraftKings is now live in 21 states and offers mobile sports betting to more than 40% of the US population. The company ended 2022 with $2.24 billion in revenue, which was a billion more than the previous year, and its market cap currently sits at $8.35 billion — up 150% from IPO but down 75% from December 2020 ($31 billion).

So for this week’s podcast, I flew to Boston and sat down with DraftKings co-founder and CEO Jason Robins. We talked about the expansion of mobile sports betting, how DraftKings intends to steal market share from its rivals, their long-term plan to lower customer acquisition costs, the future of micro-betting, and much more.

I really enjoyed this conversation with Jason and hope you do too. The podcast is available on Apple, Spotify, or YouTube. Enjoy!

I hope everyone has a great weekend. We’ll talk on Monday.

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Huddle Up is a 3x weekly newsletter that breaks down the business and money behind sports. If you are not already a subscriber, sign up and join 94,000+ others who receive it directly in their inbox each week.