Tuesday, August 25, 2026
The FOS App Launches September 1 Pre-save on the App Store Today

GOATs With Business Vision

  • After Tom Brady’s seventh Super Bowl win, many fans are debating whether he or Serena Williams is the greatest athlete of all time.
  • Both Brady and Williams are quite active as investors and entrepreneurs.
Derick E. Hingle/Robert Deutsch-USA Today Sports

After his seventh Super Bowl win, Tom Brady is widely viewed as the best player the NFL has ever seen. With that settled, Brady has drawn comparisons to greats across other sports.

One debate is especially prominent: is Brady or Serena Williams the greatest athlete of all time? Williams is currently seeking her 24th Grand Slam title at the Australian Open, an event she once won while pregnant.

What’s less debated is their respective business acumen, but you could spark an argument there as well. Both are quite active as investors and entrepreneurs.

  • Brady has founded two media companies, Religion of Sports and 199 Productions, which launched in 2020. He also started TB12, a packaged meal company geared toward athletes, and invested in the Series B round for watchmaker Hodinkee.
  • Serena’s personal investments include Impossible Foods, Bumble, and carbon offset market Pachama. She is also the Chief Sports Officer for Aston Martin, and a board member of three companies including SurveyMonkey.
  • Williams’ investment firm, Serena Ventures, has made at least ten investments since mid-2018, many in companies focused on women’s products and services.

In an interview with the New York Times, Williams agreed with Brady’s sentiment that his favorite title is the next one. “That would absolutely be my answer. Because otherwise you’re living off of what you’ve already did.”

When Brady and Williams decide to live off what they’ve already done, they’ll have plenty to work with.

Williams has netted over $92 million in tournament winnings. That, along with endorsements from the likes of Nike, Gatorade, Beats, Chase and more, have helped bring her net worth up to $225 million.

Brady, meanwhile, has raked in over $263 million in contracts from the Patriots and Bucs, and at least $140 million from endorsements.

This field is for validation purposes and should be left unchanged.

Sign up for
The Memo Newsletter

Get the biggest stories and best analysis on the business of sports delivered to your inbox twice every weekday and twice on weekends.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

First at FOS

NFL Will Continue Strict Taunting Crackdown in 2026

Taunting and celebrations will again be points of emphasis.
Dec 20, 2025; Oxford, MS, USA; Mississippi Rebels tight end Dae'Quan Wright (8) runs after a catch as Tulane Green Wave linebacker Sam Howard (15) makes the tackle during the third quarter at Vaught-Hemingway Stadium

Big Ten, SEC Ban NFL Players From Returning

Other power conferences and the American are considering the same move.
Jan 8, 2026; Glendale, AZ, USA; Mississippi Rebels tight end Dae'quan Wright (8) makes a touchdown catch against the Miami Hurricanes in the second half during the 2026 Fiesta Bowl and semifinal game of the College Football Playoff at State Farm Stadium.

More NFL Players Considering College Returns

Dae’Quan Wright can return to college thanks to a lawsuit he filed.
podcast thumbnail mobile
Front Office Sports Today

A Conversation with Joy Taylor on WNBA Culture War, NFL Season, Her Next Chapter & More

0:00

Featured Today

Dan Snyder ‘Invisible’ in NFL Three Years After Commanders Sale

Snyder has had little to no contact with former NFL associates.
Soccer Football - Premier League - Arsenal v Burnley - Emirates Stadium, London, Britain - May 18, 2026 Arsenal's Kai Havertz scores their first goal past Burnley's Max Weiss
August 21, 2026

Why the Premier League’s Star-Power Shortage Doesn’t Matter

The world’s richest soccer league doesn’t rely on big stars to dominate.
August 12, 2026

Trendy Golf Hat Divide Is More Than a Fashion Fight

As golf has gotten trendier, so has the sport’s style.
Joey Spallina of the Maryland Whipsnakes
August 6, 2026

How Eye Black Became ‘War Paint’ on the Field

“You’re going into battle, doing something you only do on game days.”
August 6, 2026

Tom Brady Explains His Aggressive Push Into Trading Cards

Brady talked to FOS about his eponymous card company.

Top Players Eliminated Early in Revamped US Open Mixed Doubles

Three pairs of doubles specialists lost on Tuesday.
August 22, 2026

How Cincy’s $260M Facelift Overhauled the ‘Worst’ Stop in Tennis

The tournament was nearly relocated to Charlotte.
August 24, 2026

Browns Name Watson Starter in Final Season of $230M Deal

Watson called Cleveland fans “disrespectful” for booing him.
Sponsored

Kerri Walsh Jennings’s Playbook for the Future of Volleyball

The former gold medalist talks NCAA, the Olympics, & investing in volleyball.
Sep 7, 2025; Flushing, NY, USA; Jannik Sinner (ITA) reacts against Carlos Alcaraz (ESP) (not pictured) during the final of mens singles at Billie Jean King National Tennis Center.
August 21, 2026

Jannik Sinner Announces He Will Miss the US Open

Carlos Alcaraz announced Thursday that he will return at the US Open.
August 20, 2026

Carlos Alcaraz to Return at US Open After Four-Month Absence

It’s not yet clear if Jannik Sinner will join him.
August 19, 2026

Ogwumike to Play in Project B Despite WNBA Retirement

She will still play for Project B, the new global basketball league.
August 18, 2026

LeBron Quickly Ascending Golf Content-Creator Ranks

The NBA star started playing golf only last year.