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:

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…

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?

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…

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?

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