How Did Dave Portnoy Make His Money? The Raw Truth Behind His $100M Empire

Dave Portnoy's path to wealth is quite remarkable. He built Barstool Sports from scratch and sold it to Penn Entertainment for $551 million through two separate deals. Then came an unexpected twist - he bought it back for just $1 a few years later. This bold business move shows Portnoy's unique approach to building his fortune.

Recent estimates put Dave Portnoy's net worth at $150 million as of early January 2025. The deal with Penn Entertainment started when he sold a 36% stake in Barstool Sports for $163 million in 2020. This included $135 million in cash and $28 million in Penn non-voting convertible preferred stock. 

Penn bought the rest of the company for $388 million in February 2023. The story took another turn when Portnoy bought Barstool back for just one dollar in August 2023. He now says he can make $5 million in a single week.

This piece will take you through Portnoy's rise to his $150 million empire. We'll look at everything from Barstool's early days to his multiple revenue streams and the controversial moments that shaped his success.

How Dave Portnoy Made His First Millions

Dave Portnoy's path to millions started with a gutsy decision to quit his job. "I hated my job and I wanted to find something I liked doing, and I gambled," Portnoy explained. This gamble would pay off beyond anyone's wildest dreams.

Starting Barstool Sports in Boston

Offshore casinos turned down Portnoy's marketing job application but suggested he could sell ad space if he started a newspaper. This sparked an idea, and in 2003, he launched Barstool Sports as a basic black-and-white newspaper in Boston. The paper started small - just four pages of sports content that focused on gambling ads and fantasy sports predictions.

Distribution was as basic as it gets. Portnoy handed out papers himself at subway stations and Boston street corners. He even got creative and hired local homeless people to help distribute near Boston T stations.

Turning a newsletter into a media brand

The paper struggled until 2004 when Portnoy made a smart move. He added photos of women in bikinis to the front page. This change caught readers' attention, and by 2007, Barstool launched its first website.

The brand grew as Portnoy developed his online character "El Presidente." His direct, no-nonsense style appealed to young male readers. A big step came in 2009 when he hired Kevin Clancy and created Barstool New York, the first expansion beyond Boston.

Barstool's success showed in the numbers. By December 2013, the site pulled in more than four million unique monthly visitors and racked up over 80 million page views. The company kept growing and spread to five cities by 2013, including Philadelphia and Chicago.

Early revenue from gambling and ads

Barstool's money-making strategy evolved naturally from its roots. PartyPoker, an online card room operating illegally in the US, became one of the first big advertisers. Portnoy's approach was straightforward: "As we've continued to grow, we've always been very upfront with the advertising side of it".

Everything changed in January 2016 when The Chernin Group bought a majority stake in Barstool Sports, valuing the company between $10-15 million. This was just the start - by 2019, Barstool pulled in between $90-100 million yearly, mostly from podcasts, merchandise sales, and gambling deals.

Portnoy's story shows how authentic content and loyal fans can build a media empire. He went from handing out papers at Boston subway stations to creating a multi-million dollar business that keeps growing rapidly.

The Barstool Sports Empire and Its Sale

Dave Portnoy made his biggest money moves by selling Barstool Sports twice through some clever business deals that boosted his wealth by a lot.

Chernin Group's original investment

A major breakthrough happened in January 2016 when The Chernin Group bought a 51% majority stake in Barstool Sports. The deal valued the company between $10-15 million. This partnership helped Barstool grow from a regional brand into a national media powerhouse. 

The company moved its headquarters from Boston to New York City after the investment. Portnoy managed to keep complete creative control as Chief of Content.

The Chernin Group believed strongly in the company. They invested another $15 million in 2018, which brought their total investment to $25 million. This extra funding pushed Barstool's value above $100 million. The Chernin Group owned about 60% during this time.

Penn Entertainment's $551M acquisition

Penn National Gaming stepped in as Barstool's next big investor in January 2020. They bought a 36% stake for $163 million ($135 million in cash and $28 million in non-voting convertible preferred stock). This original deal valued Barstool at $450 million.

Penn finished the acquisition in February 2023 by buying the remaining interest for about $388 million. Their total investment reached $551 million. This huge sale added significantly to Portnoy's personal wealth.

Reacquiring Barstool for $1

The business world saw an amazing twist when Portnoy bought back Barstool from Penn Entertainment for just $1 in August 2023. This incredibly good deal came after Penn locked in a 10-year, $2 billion agreement with ESPN. They agreed to rename the Barstool Sportsbook as 'ESPN Bet'.

Penn reported a "pre-tax non-cash loss" between $800-850 million despite this cheap buyback. The agreement had one catch: Penn would get 50% of any money if Portnoy sells Barstool again. In spite of that, Portnoy has clearly stated he'll "hold it 'til I die".

Portnoy explained why they split: "We got denied licenses because of me... the regulated industry probably not the best place for Barstool Sports".

Other Income Streams That Built His Net Worth

Dave Portnoy has expanded his wealth through multiple revenue streams that demonstrate his business savvy, going well beyond Barstool Sports.

Davey Day Trader and stock market plays

The COVID-19 pandemic in 2020 led Portnoy to venture into stock trading when sports leagues shut down. He launched his "Davey Day Trader" persona in March 2020 and happened to start at the market's absolute low point. 

He invested hundreds of thousands in companies like Boeing and Alibaba, and his timing aligned perfectly with stimulus money flowing into the economy. The subsequent market rally drew attention to his trading activities, which earned him spots on CNBC.

Pizza reviews and One Bite brand

His media empire grew stronger as he established himself as the "biggest pizza influencer" online. College students everywhere began repeating his catchphrase "one bite, everybody knows the rules". 

This success paved the way for his One Bite frozen pizzas, now available in 3,500 Walmart stores at $6.48 each. Customers can choose from four varieties: pepperoni, supreme, three meat, and five cheese.

Real estate investments and luxury homes

Portnoy's real estate portfolio has grown to an impressive $95 million with properties in Massachusetts, New York, and Florida. He bought a $42 million Nantucket home in 2023, a record-breaking $27.75 million mansion in Islamorada, Florida Keys, and a $13.98 million waterfront property in Miami.

Brand deals and media partnerships

Portnoy secured a significant deal with FOX Sports. The partnership includes appearances on "Big Noon Kickoff" for college football coverage and a new Monday show on FOX Sports 1. FOX is setting up a dedicated Barstool studio in Chicago to support this expansion. His brand partnerships also include PHX, a hydration energy drink.

Controversies, Setbacks, and Philanthropy

Dave Portnoy built his wealth while dealing with the most important controversies and making a positive effect through philanthropy. These experiences challenged and shaped how his business empire grew.

Sexual misconduct allegations and lawsuits

Two women came forward in 2020 with serious allegations against Portnoy. They claimed their sexual encounters with him turned violent and humiliating. One woman said he filmed her without consent during sex, while another claimed she needed hospitalization for depression after their encounter. 

Portnoy strongly denied these accusations. He called them a "hit piece" and maintained all encounters were "100% consensual". The allegations led gambling regulators in two states to examine Barstool Sports.

Union-busting and labor board settlement

The National Labor Relations Board reached a settlement with Portnoy in 2020. He had threatened to fire employees "on the spot" if they tried to unionize. The settlement made him delete anti-union tweets and remove related content. He also had to inform employees about their right to organize. His company admitted they created a fake Twitter account to spot pro-union employees.

Raising millions for small businesses and charities

Portnoy ended up making his biggest positive effect through The Barstool Fund during COVID-19. He started with his personal $500,000 contribution. The initiative collected over $35 million and helped more than 600 struggling small businesses. The fund received one donation every three seconds during peak hours and achieved an impressive 28% conversion rate.

Conclusion

Dave Portnoy built his $150 million empire through Barstool Sports. He made his biggest profits by selling it twice to Penn Entertainment for a combined $551 million and bought it back for just $1. His remarkable business story started with a simple gambling newsletter on Boston streets that grew into a digital media powerhouse. 

He expanded his wealth with perfect timing when he launched "Davey Day Trader" at the market bottom during COVID-19. His casual pizza reviews became the successful One Bite frozen pizza brand now available in thousands of Walmart stores across the country.

Portnoy's wealth goes beyond the media. He owns a $95 million real estate portfolio across Massachusetts, Florida, and New York. His new collaboration with FOX Sports strengthens his position as a media mogul, with a dedicated Barstool studio in Chicago. His rise came with controversies - from sexual misconduct allegations to labor disputes. 

Yet he balanced these challenges with generous giving, especially through The Barstool Fund that raised over $35 million to help struggling small businesses during the pandemic.

Without doubt, Portnoy's path to wealth breaks all conventional business rules. He bounces back from setbacks that would crush other careers because he knows when to change direction while staying true to his controversial image. 

Not many entrepreneurs can say they sold a company for hundreds of millions only to buy it back for less than a coffee costs. His unique business approach combines authentic content and loyal fans with a bold attitude toward risk that paid off in spectacular fashion.

FAQs

Q1. How did Dave Portnoy start his business career? 

Dave Portnoy started his business career by launching Barstool Sports in 2003 as a free black-and-white newspaper in Boston. He initially distributed the paper himself at subway stations and street corners, focusing on gambling advertisements and fantasy sports projections.

Q2. What was the key factor in Barstool Sports' financial success? 

Barstool Sports' financial success can be attributed to its diverse revenue streams. The company generated income from podcasts, merchandise sales, gambling deals, and advertising. By 2019, Barstool was generating between $90-100 million in annual revenue.

Q3. How did Dave Portnoy manage to buy back Barstool Sports for just $1? 

Portnoy repurchased Barstool Sports for $1 in August 2023 after Penn Entertainment secured a $2 billion agreement with ESPN. This deal occurred because Penn agreed to rebrand the Barstool Sportsbook as 'ESPN Bet', allowing Portnoy to regain control of the Barstool brand.

Q4. What are some of Dave Portnoy's other significant income streams? 

Besides Barstool Sports, Portnoy has diversified his income through stock trading as "Davey Day Trader", launching the One Bite frozen pizza brand, investing in real estate, and securing media partnerships, including a recent deal with FOX Sports.

Q5. How has Dave Portnoy used his wealth for philanthropy? 

During the COVID-19 pandemic, Portnoy launched The Barstool Fund with a personal contribution of $500,000. The initiative raised over $35 million and supported more than 600 struggling small businesses, processing donations at a remarkable rate during peak hours.