A year after buying 36% of Barstool Sports for $163 million, Penn National Gaming is joining the S&P 500. The index of 500 large companies also welcomed Caesars in a reshuffle that signals a belief in the growing prominence of gambling.

Penn and Caesars join Las Vegas Sands, MGM Resorts International, and Wynn Resorts on the oft-cited stock index.

Barstool launched its sportsbook in Illinois earlier this month ahead of March Madness and is also live in Michigan and Pennsylvania. Penn CEO Jay Snowden said he hopes to be in every legally viable state by the end of 2021.

Penn’s stock has risen astronomically in the last year, growing 17-fold from where it was last March, lifted by the steady string of states that have legalized sports betting.

Caesars stock is similarly bullish, up 1,300% from where it was a year ago. The company recorded $1.5 billion in revenue during Q4 2020, compared to $592.12 million in Q4 revenue the year prior.

Both Penn, which also owns race tracks and casinos, and Caesars got a stock boost on Friday after the S&P’s announcement, which will take effect on March 22.

For each company, the listing represents a tremendous comeback after taking a major revenue hit a year ago when casinos, restaurants, and other core businesses shut down amid the pandemic.

RumbleOn, an e-commerce platform where motorcycles are bought, sold, and traded, has acquired RideNow Powersports, the nation’s largest powersports retailer, per Bloomberg. 

RumbleOn agreed to a purchase price of $400.5 million in cash and $175 million in Class B common stock. The deal will form powersports’ first omni-channel customer experience in North America. Revenue for the two entities is expected to reach a combined $1.5 billion in 2021.

“RideNow’s significant physical retail platform provides the missing piece of a ‘bricks and clicks’ strategy for RumbleOn, enabling us to reach consumers wherever they want to shop, whether online, offline, or both,” said RumbleOn CEO Marshall Chesrown.

As a result of the acquisition, Oaktree Capital, an investment management firm, will provide RumbleOn with $250 million, with the opportunity for that number to increase to $280 million.

The move comes as RumbleOn works to recover significant losses due to the pandemic. Total revenue for e-commerce platform reached $416.4 million in 2020, a steep drop from $840.6 million in 2019. 

On Monday, RumbleOn’s market cap reached $128 million, as shares jumped from $48.87 at market open to $57.50. The acquisition is set to bring the enterprise value of RumbleOn to around $850 million.

Despite limitations on in-person gatherings, Dungeons & Dragons had a monster 2020.

D&D, the tabletop board game published by Wizards of the Coast, a subsidiary of Hasbro, saw sales jump 33% last year, marking the biggest year ever for the game and six consecutive years of growth, per CNBC. 

Hasbro acquired Wizards in 1999 for $325 million in stock. Wizards reported revenue of $816 million in 2020, a 24% increase from 2019. Hasbro saw revenue of $5.47 billion for the year.

D&D’s growth continued as players gravitated toward online platforms to play a game that has been part of popular culture since 1974. 

“It’s the perfect time right now for role playing, people have more time on their hands, and if you want to relax and see your friends the best way is through virtual gaming,” Satine Phoenix, former Wizards community manager, told The Wall Street Journal. 

Wizards hopes to sustain D&D’s momentum in 2021 by attracting new players. D&D saw record sales for its starter products in 2020. Now, Wizards plans to launch two D&D video games and increase its publishing rate of new books and box sets.

Last year, U.S. toy sales reached more than $25 billion, a 16% boost from the year before, according to The NDP Group.

Elon Musk’s SpaceX was knocked off the top of the most valuable startup list. In its place? A company you’ve probably used to shop online.

Online payment processor Stripe raised $600 million in its latest funding round, nearly tripling its valuation to $95 billion. It was valued at $36 billion last April.

Stripe’s software accepts payments and other transactions for millions of businesses, including sports-based ones like OpenSports and LeagueApps — online platforms that organize community sports groups and events.

• OpenSports lists over 250,000 orders per year.
• LeagueApps hit $15 million in revenue in 2020.

“I view this as a bit more opportunistic,” Chief Financial Officer Dhivya Suryadevara said about Stripe’s additional funding. The company “is highly capital efficient.”

PayPal is still the sector’s leader with a $359 billion valuation. It’s been public since 2002 and is integrated with most sports betting services. Square has also seen an uptick in use with sports organizations and has deals with stadiums like Nationals Park and the Chase Center.

Board member Mike Moritz considers the $600 million a “rainy day” fund. “It pays to have a little more insurance,” he said.

Stripe plans to use the latest round of funding to invest in its European operations as global payments and e-commerce continue to grow.