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Sold for $550M, Bought Back for $1: The Barstool Story
Inside Dave Portnoy's Business Move
Hey TechNerds,
It's Jas from The Tech Route!
The newsletter for your weekly tech breakdowns - Decoding your favorite tech businesses and entrepreneurs in under 3 mins.
Here’s what’s on the menu today:
Business tips of the week: How to start & grow your business.
Entrepreneur of the week: Entrepreneur’s journey from broke to $550M
Question of the week: What current job role are you in? (At the bottom)
Business Tips of the Week:
Starting a Business:
14 types of businesses you can start: Link
My current business plan: Link
Weekly Motivation:
Failures are a part of your success: Link
Entrepreneur of the Week:
Dave Portnoy sold Barstool for $550M Dollars.
But, he just bought it all back for…
$1 Dollar.
Here’s how:
![](https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80/uploads/asset/file/20cfc9e5-cfea-49e3-9daf-85e315680a9d/Untitled__24_.png)
Dave, a Boston sports lover in 2003...
Launched Barstool Sports as a print publication.
By 2007, it wasn’t just about Boston.
A website, podcasts, videos, merch, and more.
Hitting the sweet spot with young male sports fans he…
![](https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80/uploads/asset/file/657dec2f-c1ff-4de0-b4d4-64d860ec3733/Untitled__26_.png)
Gained traction against sports giants like ESPN.
By 2016, The Chernin Group saw potential.
Investing $15M for a minority stake.
Two years later, upping their stake with another $25M.
Dave, still in charge of content, pocketed $40M (after taxes)…
So how did he get to 100M?
![](https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80/uploads/asset/file/471b6122-9d9b-4357-9b06-a3dbe7707fd2/Untitled__27_.png)
But Barstool? It was just getting started.
In 2020, Penn Gaming stepped in.
Paying $163M for 36% of Barstool.
By August 2022, Penn owned 100% of Barstool.
Having spent $550M in total.
But here's the twist...
Penn Gaming later struck a $2B deal with ESPN.
A deal that doesn't allow other betting partnerships.
Problem? Penn's betting brand was "Barstool Sportsbook."
Penn's solution…
![](https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80/uploads/asset/file/2ac1a092-322f-4097-816f-5df446df2efa/Untitled__28_.png)
Sell Barstool back to the only viable buyer: Dave Portnoy.
For how much? A single dollar.
Why so cheap?
Penn had one buyer, Dave.
Selling for $1 meant a huge future write-off for Penn.
And Dave?
![](https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80/uploads/asset/file/75521ef6-e8f4-41d0-aa43-0eb8944318d5/Untitled__29_.png)
He agreed to some conditions.
No badmouthing Penn or ESPN.
No licensing the Barstool name to other sportsbooks.
And giving Penn 50% of any future Barstool sale profits.
To sum it up:
Dave Portnoy, from starting a magazine in 2003.
To a $100M net worth from selling Barstool for $350M.
And now? Re-acquiring it all for just $1.
My key takeaway:
Power of Brand: Barstool's distinct voice cut through the noise in a packed market.
More than just fans, it drew big business.
Lesson?
Nail your brand, and everything else will follow.
Thank you for tuning in this week,
— Jas, The Tech Route