Dave Portnoy just beat the house, three-and-a-half years after selling Barstool Sports to casino operator Penn Gaming.

Driving the news: Penn yesterday announced that it sold Barstool Sports back to Portnoy for little more than a handshake and a headshake, despite having paid $551 million for the acquisition.

• The move was made in conjunction with Penn launching a betting joint venture with ESPN, marking the sports network's first major gambling deal.
• Penn will rebrand its Barstool Sportsbook to ESPN Bet, in a 10-year deal initially valued at around $2 billion.

Behind the scenes: The controversial Portnoy, who once had his own failed partnership with ESPN, will own 100% of Barstool's original media business, which includes a popular website and podcasts.

• He's subject to certain non-compete agreements, and would provide Penn with 50% of any gross proceeds were he to resell Barstool — however, Portnoy said yesterday that he'll "hold it 'til I die."
• It's unclear if ESPN insisted on the Barstool divestiture as part of its agreement, or if Penn was tired of the headaches Barstool caused (including with gaming regulators).

To recap: Portnoy gets hundreds of millions of dollars via the original Penn Gaming sale — albeit not all $551 million, since an outside investor owned 51% — and less than four years later gets back 100% control of what he sold.

• One possibility is that he rebuilds Barstool into a very cushy lifestyle business, particularly given that it'll be free of Penn-related restrictions whereby Barstool couldn't take ads from other sports betting companies.
• Another is that he does indeed sell, in which case he gets half the proceeds.
• Worst case scenario is that Barstool fails, and Portnoy is left with those hundreds of millions of dollars.
• Penn, meanwhile, paid big for a young sportsbook audience, but couldn't crack 5% market share. Now it will rebrand into a maturing sector that's about to get a well-capitalized upstart in Fanatics, with a partner in ESPN whose own corporate future is uncertain. Oh, and all of those rival sportsbooks like FanDuel and DraftKings will still be allowed to advertise on ESPN.

The bottom line: Portnoy made a big bet with Penn, and it paid off better than he could have imagined.

Go deeper: Axios Pro: Media Deals will have a lot more on Penn, ESPN and Barstool in this morning's newsletter.

WeWork (NYSE: WE) interim CEO David Tolley said on an earnings call that "substantial doubt exists about the company's ability to continue as a going concern."

Why it's the BFD: The co-working space operator is a long ways from when it was one of the world's most valuable startups, once valued by SoftBank at $47 billion, but there's a big difference between losing luster and losing everything.

The bottom line: WeWork reported a $397 million net loss for Q2 2023 on $877 million in revenue, both year-over-year improvements, but Tolley said membership declined due to economic volatility and increased competition that's being driven by excess commercial real estate supply.

• WeWork shares closed trading yesterday at just 21 cents each, and opened even lower this morning.

🚑 ADARx Pharmaceuticals, a San Diego-based developer of RNA therapeutics, raised $200m in Series C funding. Bain Capital Life Sciences and TCGX co-led, and were joined by Blackrock, Commodore Capital, Cormorant Asset Management, HB Healthcare Investments, Invus, Marshall Wace, Redmile Group, T. Rowe Price, Venrock, Vivo Capital and insiders Ascenta Capital, Lilly Asia Ventures, OrbiMed and SR One Capital Management. www.adarx.com

🚑 Alltrna, a Cambridge, Mass.-based transfer RNA startup focused on codon diseases, raised $109m in Series B funding from backers like Flagship Pioneering. https://axios.link/3KAwlup

• Weights & Biases, an SF-based ML ops platform, raised $50m. Daniel Gross and Nat Friedman co-led, and were joined by insiders Coatue, Insight Partners, Felicis, BOND and BloombergBeta. https://axios.link/3DV6kC9

🚑 Capstan Medical, a developer of robotic-assisted heart valve surgery tech, raised $31.4m in Series B funding, per Axios Pro. Eclipse Ventures led, and was joined by Intuitive Ventures, Puma Venture Capital and heart surgeon Vipul Patel also participated. https://axios.link/45lUzAx

• Deepset.ai, a German enterprise platform for building LLMs, raised $30m. Balderton Capital led, and was joined by insiders GV and Harpoon Ventures. www.deepset.ai

• Endowus, a Singaporean wealth management startup, raised $25.6m from Citi Ventures, MUFG Innovation Partners, UBS Next, Singapore's EDBI, Prosus Ventures (owned by Naspers), Lightspeed Venture Partners and Singtel Innov8. https://axios.link/3qhPMBt

• Symmetry Systems, a San Jose, Calif.-based data security posture management startup, raised $18m. OVN Capital led, and was joined by Adit Capital, TSG and existing investor Forgepoint Capital. www.symmetry-systems.com

• Sweet Security, an Israeli cloud security startup, raised $12m in seed funding. Gilot Capital Partners led, and was joined by CyberArk Ventures. https://axios.link/3ONGxlH

• Puck, a media startup, raised over $10m in Series B funding led by J Rothschild Capital Management, per Axios. https://axios.link/43ZYpy3

⚡ Treehouse, a Detroit-based home EV charging installer, raised $10m, per Axios Pro. Montage Ventures and Trucks VC co-led, and were joined by CarMax, Assurant Ventures, Acrew Capital, Gutter Capital, Detroit Venture Partners, Holman and Automotive Ventures. https://axios.link/3YI7QBz

• Catch+Release, a content licensing marketplace for brands and creators, raised $8.8m in Series A funding. Accel led, and was joined by HarbourVest Partners, 35Ventures, Cervin and Stagwell. www.catchandrelease.com

• Parcha, an SF-based compliance and risk management automation startup, raised $5m. Kindred Ventures and Initialized Capital co-led, and were joined by Propel, Fin Capital, Liquid2 Ventures, Comma Capital, CapitalX and Popular Impact Fund. https://axios.link/3KyD0W6

• Dropzone AI, an autonomous alert investigation platform for security ops teams, raised $3.5m in seed funding. Decibel Partners led, and was joined by Pioneer Square Ventures. https://axios.link/3YouVsI

🚑 Family Resource, a Liberty Lake, Wash.-based portfolio company of Great Point Partners, acquired Companion Care, a Woodinville, Wash.-based home care agency. www.familyresourcehomecare.com

• KKR and bikemakers Trek and Giant are among the possible suitors for bankrupt e-bikemaker VanMoof, per the Micromobility newsletter. https://axios.link/3OIWny1

• KKR acquired a $373m portfolio of prime auto loans from Synovus Bank (NYSE: SNV). https://axios.link/450Tsqi

• Kohlberg & Co. acquired Engage PEO, a Hollywood, Fla.-based provider of HR outsourcing solutions to SMBs, from Lightyear Capital. www.engagepeo.com

• Landways, a British provider of in-building digital and power infrastructure, raised capital from Newlight Partners and insider Columbia Capital. www.landways.com

• Lone Star Funds and Platinum Equity are bidding for DuPont's resins unit, which could fetch around $2b, per Bloomberg. https://axios.link/3YrYOrX

• Novacap bought New York-based TV ad tech firm Cadent for around $600m from Lee Equity Partners. https://axios.link/3DPuRsv

• PeopleGrove, an Arlington, Va.-based portfolio company of The Riverside Company, acquired JobZology, a career SaaS for college students. www.peoplegrove.com

⚡ Synthica Energy, a Cincinnati-based developer of biogas from food waste, raised an undisclosed amount of funding from Goldman Sachs Asset Management. https://axios.link/3OuA1z5

• TA Associates and Warburg Pincus acquired Epassi Group, a provider of employee benefits in Nordic countries, from Bregal Milestone. www.epassi.com

• TPG agreed to buy Australian funeral home operator InvoCare (ASX: IVC) for A$1.8b. https://axios.link/3OM3q9h

• TricorBraun, a St. Louis-based portfolio company of Ontario Teachers' Pension Plan, acquired CanSource, a Longmont, Colo.-based provider of beverage packaging, from Broadtree Partners. www.cansource.com

• Willis & Smith Capital acquired Performance Stamping, a Carpentersville, Ill.-based provider of metal stamping to industrial customers. www.performancestamping.com

• Amazon (Nasdaq: AMZN) is in talks to be an anchor investor in the upcoming IPO for chipmaker Arm, per Reuters. https://axios.link/452uXJ8

• CVC Capital Partners is considering a 2024 IPO for German perfume maker Douglas, which could be valued at more than €7b, per Bloomberg. https://axios.link/45m9YRy

• Cinven hired BofA and Goldman Sachs to find a buyer for Partner in Pet Food, a Hungarian pet food maker that could fetch more than €2b, per Bloomberg. https://axios.link/3YshPdZ

• Rubrik, a Palo Alto, Calif.-based data management "unicorn," agreed to buy Laminar, a data security company that raised over $60m from firms like Insight Partners, SentinelOne, Salesforce Ventures, Tiger Global Management, TLV Partners and Meron Capital. No financial terms were disclosed, but TechCrunch pegs the price at $200m-$250m. https://axios.link/3OQkqeI

• JD Sports (LSE: JD), a British sportswear retailer, agreed to acquire the 40% stake it doesn't already hold in Polish retailer Marketing Investment Group. https://axios.link/3Oq7mLA

• Reinold Geiger, the billionaire controlling shareholder of Hong Kong-listed L'Occitane International, is in talks to take the Swiss skin care company private for around $6.5b, per Bloomberg. https://axios.link/3s5G6dT

• Tilray Brands (Nasdaq: TLRY), a Canadian cannabis company, agreed to buy eight beer and beverage brands from Anheuser-Busch (NYSE: BUD). https://axios.link/3KwpzpF

• Knife Capital, a South African growth equity firm, raised $50m for its third fund. https://axios.link/3KD7Oov

• Omers Ventures of Canada is pulling out of Europe, with plans to refocus all its attention on North America. https://axios.link/3YtLhQD

• Ribbit Capital raised $800m for its 10th fintech-focused VC fund, per an SEC filing.

• Anshu Agarwal, co-founder and former CEO of Nimbella (acquired by DigitalOcean), joined Converge VC as a general partner. www.converge.vc

• David Kurtz, Lazard's global head of restructuring, is joining Hilco as vice chair and chief strategic officer. https://axios.link/3OpWHjX

Alt asset firm earnings season is almost over. The basic story was that earnings fell year-over-year, although usually by less than analysts expected.