From Street Corners to $551M: Dave Portnoy's Barstool Exit

Big Bets & Even Bigger Exits


June 8, 2023

What up, Dealpreneurs!

In the world of media & entertainment, one man defied the odds & turned his personal brand into a massive success story.

Dave Portnoy transformed Barstool Sports from a local sports newspaper into a media empire worth $551M.

But how? How did he manage to scale Barstool Sports into an exitable business, breaking the mold of personal brand limitations?

Keep reading to discover how to take his playbook & apply it to your own ventures, unlocking growth potential & paving the way for a bigger, more successful exit.

Don’t have time & would rather listen? Check out the vid here!


The Start

Dave Portnoy graduated from the University of Michigan in 1999 with a degree in education. After 4 years of working in IT market research, Portnoy quit & started Barstool Sports after realizing the gap in sports betting.

He originally distributed his print newspaper on street corners & in subway stations.

Barstool Sports quickly gained popularity for its irreverent & authentic approach to sports coverage.

Capitalizing on this notoriety, Barstool moved onto the world wide web.

The first few years marked a crucial phase in the company's evolution, setting the stage for the rapid expansion & transformation that would follow in the years to come.

The Pivot

Around 2012, recognizing the rise in social media & the potential to engage with a wide audience, Barstool sports moved to platforms like Twitter, Facebook, & Instagram. 

This allowed the company to connect with fans in real-time & ultimately cultivated a dedicated following.

Barstool Sports also underwent a shift away from being solely centered around Dave Portnoy's character & persona.

Barstool Sports strategically expanded its content offerings to include a diverse range of personalities & writers, reducing reliance on Dave Portnoy as the sole representation of the brand.

Additionally, Barstool Sports introduced a mobile app, which expanded their reach & enhanced user experience by providing convenient access to a diverse range of sports, pop culture, & entertainment content.

Lastly, Barstool Sports embraced a direct-to-consumer approach, leveraging e-commerce & merchandise sales. 

By creating branded products & engaging their audience through online sales, the company found new revenue streams & further solidified its brand identity.

The Exit

In 2016, Barstools Sports decided to seek outside investments & sold a 51% stake to The Chernin Group (TCG) priced around $10-15M & immediately moved its headquarters to New York City.

While TCG had a controlling interest in the company, Portnoy remained 100% in control of the editorial content.

Then, in 2020, Penn National Gaming (PNG) acquired a 36% stake in Barstool Sports for $163M. At this point, Dave Portnoy & other few executives owned 13% of the company.

Finally, in February 2023, PNG acquired the remainder of Barstool Sports for $388M.

The Personal Brand Playbook

(1) Identify a gap in the market & quickly achieve product-market fit.

— Portnoy saw a gap in sports betting publications & sought feedback from his target audience to tweak his content

(2) Meet the market where it is by offering a no-brainer purchase that provides value to the customer.

Leveraged social media & introduced merch, subscriptions, & events

(3) Use profits to reinvest in the business, building community & distribution away from any single person risk and diversify the distribution channels.

Reinvested in content production, hiring talented personalities, & expanding their media portfolio

(4) Dominate the niche you create & build a brand that becomes synonymous with it.

Through relentless dedication, authentic content, & a deep understanding of their target audience

(5) Sell the company to a larger player for a significant return on investment.

— $551M+ exit, enough said

Want a deep dive into Barstool’s exit?

Check out our podcast here!

I want to invest in your business

I’m looking for my 4th deal in 2023.

My most recent deal has doubled the Trailing 12 Profit in the 4 months since we’ve owned it & the owner works half as much as she used to, while focusing on the part of the business she loves.

Here’s what I buy:

  • Owner led looking for a big exit in 3-5 yrs (we buy in & help)

  • Digital Businesses (courses, newsletter personal brands, certifications)

  • Min 500k trailing 12 profit

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I rarely buy the entire business, I don’t want in if you want out, but I want to hop in the boat with you, relieve the operational burdens & quadruple the exit multiple with you.

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