Barstool Sports is selling part of its business to a casino operator in a deal that values the company at $450 million

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Barstool Sports,
the sports media site, has agreed to sell a 36% interest stake in its business
to casino operator Penn National Gaming. That’s approximately $163 million in
cash and convertible preferred stock. The deal would value Barstool at $450

The deal would give Penn National exclusive rights to use
the Barstool brand for all of its online and retail sports betting and iCasino
products. In the fall, Barstool launched Barstool Bets, a platform that offers
free-to-play betting contests. 

“With its leading digital content, well-known brand and deep roots in sports betting, Barstool Sports is the ideal partner for Penn National and will enable us to attract a new, younger demographic, which will nicely complement our existing customer database,” said Penn National CEO Jay Snowden in a news release.

What’s interesting here is that Penn National isn’t exactly
focused on Barstool’s content. It’s looking more at monetizing a
cult-like, sports-obsessed audience. The partnership would allow Penn National
to market its products to Barstool’s audience of nearly 66 million monthly
unique visitors. According
to Vox
, Barstool generated between $90 million and $100 million in revenue
last year, with the majority coming from podcasts, merchandise sales, and
gambling deals.

I spoke with the CEOs of fantasy sports companies DraftKings
and FanDuel after the U.S. Supreme Court cleared
the way
in 2018 for states to legalize sports betting, striking down a 1992
federal law that had banned the practice in most states. FanDuel CEO Matt King
told me at the time that a market expansion like that one was bound to attract
many new competitors.

Many sports publishers, including Bleacher Report, ESPN and
Sports Illustrated, have established
content verticals
dedicated to sports betting. It’ll be interesting how
many of them begin rolling out sports betting apps a la Barstool. It’s only
just the beginning for this brave new world.

First, where do you think a small investment in health/health care (less than
$1 million) would have the greatest near-term impact? Second, where you think a
large investment in health/health care ($1 billion or more) would have the greatest
long-term impact?

Both questions were posed to me by Fortune’s Editor-in-Chief, Clifton Leaf, yesterday. The questions drive to a big, lasting issue: As Term Sheet readers know well, the healthcare industry is in the midst of a bottom-to-top disruption—one largely led by venture capital and private equity investment. Entrepreneurs are, in a sense, driving care to become more personalized, more mobile, more pinpoint, and more preventive in nature, and the changes are transforming virtually every aspect of the health care industry.

That’s why, five years ago, Fortune launched its
famed Brainstorm
Health conference
—to highlight the corporate leaders, entrepreneurs, and
investors who are building this brave new world. And in our 2020 event, on
April 21-22, at the Ritz-Carlton in Marina Del Rey, California,
we’ll get
to explore how to invest in this transformation with an unbelievable list of
experts, including:

— The CEOs of Amgen, Ancestry, AT&T Business, Baxter
International, Beyond Meat, Box, Cardinal Health, Centene, Cisco, GE
Healthcare, Levi-Strauss, Whoop, and many others;

— The leaders of Google Health, the American Heart
Association, the National Institute of Mental Health, Stanford University
School of Medicine, and Verily

— Investor-philanthropist-entrepreneur Sean Parker, CNN
Chief Medical Correspondent Dr. Sanjay Gupta, NBA Commissioner Adam Silver;

—Co-chairs Arianna Huffington and Dr. David Agus, and dozens
of other leading thinkers and builders.

If you want to join the Fortune team in Marina Del Rey this April, please shoot me a note at It’s invitation-only, but there are a few spots left.

TIME’S UP: In partnership with Time’s Up, Fortune
reached out to all the 2020 presidential candidates with a list of questions
about about their policy positions related to gender equity and working
families. Thirteen of the remaining 15 candidates—including President Trump—participated,
with many doing exclusive video interviews. Read

Polina Marinova
Twitter: @polina_marinova

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