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

January 29, 2020, 3:06 PM UTC

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 million.

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.

JOIN FORTUNE AT BRAINSTORM HEALTH: Two questions: 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 polina.marinova@fortune.com. 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 more.

Polina Marinova
Twitter: @polina_marinova
Email: polina.marinova@fortune.com 

VENTURE DEALS

- Justworks, a New York-based HR technology company, raised $50 million in Series E funding. Union Square Ventures and FirstMark Capital led the round, and was joined by investors including Bain Capital Ventures, Index Ventures, Redpoint Ventures, Spark Capital, and Thrive Capital.

- Advano, a New Orleans-based company focused on lithium-ion battery technology, raised $18.5 million in Series A funding. Mitsui Kinzoku SBI Material Innovation Fund, Tony Fadell’s Future Shape, and People Fund co-led the round. 

- Roambee, a Santa Clara, Calif.-based on-demand shipment and asset monitoring platform company, raised $15.2 million in Series B funding. Anchor Group led the round, and was joined by investors including Intuitive Ventures, Jebsen & Jessen, Telkomsel and Anant Singhania. 

- Bond, a New York-based startup that offers ecommerce companies delivery and distribution center services, raised $15 million in funding. Investors include Lightspeed Venture Partners, MizMaa Ventures, and TLV Partners.

- Pecan.ai, an Israel-based deep learning platform, raised $11 million in Series A funding. Dell Technologies Capital and S Capital co-led the round. 

- Nuweba, a provider of application aware serverless security services, raised $10.2 million in seed funding. Blumberg Capital led the round, and was joined by investors including Magma Partners and Target Global. 

- Concentric, a San Jose, Calif.-based AI-powered enterprise data management platform to secure unstructured business-critical data, raised $7.5 million. Investors include Clear Ventures, Engineering Capital, Homebrew and Core Ventures. 

- Lynq Technologies, Inc., a New York-based deep-tech startup that connects people and devices across miles without infrastructure, raised $6 million in seed funding. Investors include ff Venture Capital, Sony Innovation Fund, Chetrit Ventures, and Plus Eight Equity Partners. 

- AmazeVR, a Sunnyvale, Calif.-based cloud-based platform for VR content production and distribution, raised $2.5 million in Series A funding. Investors include Partners Investment and YG Investment

- 1Huddle, a Newark-based workforce tech company that trains and motivates employees through mobile games, raised $5 million in Series A funding. Tribeca Venture Partners led the round, and was joined by investors including Humbition, NRD Capital and Newark Venture Partners.

- Encantos, a Corte Madera, Calif.-based creator of direct-to-consumer family entertainment education brands, raised $2 million in seed funding. Kapor Capital led the round, and was joined by investors including Boston Meridian Partners, Chingona Ventures, Human Ventures, and MathCapital. 

- Crown Affair, a New York-based beauty brand, raised $1.7 million in funding from Brand Foundry, Amplifyher Ventures, Thirdlove’s Heidi Zak, Create & Cultivate’s Jaclyn Johnson, Brian Spaly of Bonobos and TrunkClub, and Shiza Shahid of Malala Fund and OurPlace.

PRIVATE EQUITY DEALS

- Marlin Equity Partners acquired RevenueWell, a Chicago-based provider of cloud-based dental software. Financial terms weren't disclosed. .

- Gryphon Investors made a majority investment in PestRoutes, a McKinney, Texas-based provider of software for pest control companies. Mainsail Partners will retain a minority stake. 

- Northgate Capital and Alta Growth Capital acquired a majority equity interest in USK Urresko Holding S.A.P.I. de C.V., a manufacturer serving the North American heavy truck industry. Financial terms weren't disclosed. 

IPOs

- Calisen Group, a London-based smart meters supplier, plans to raise 408 million pounds ($536.28 million) in an IPO in the U.K., valuing the firm at as much as $1.87 billion. KKR backs the firm. Reuters.

PEOPLE

- Baum Capital Partners promoted Jon Biggs and Brian Coleman to principal, Sam Barton to vice president, and Samantha Carter to associate.

- Evan Cohen is joining Human Ventures as a venture partner.