Wednesday, August 5, 2026
  • -
    days
  • -
    hours
  • -
    minutes
  • -
    seconds

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

Former Pittsburgh Panther and retired NFL defensive tackle Aaron Donald speaks live as a special guest during the ESPN GameDay broadcast on the sidelines at Acrisure Stadium in Pittsburgh, PA prior to the start of the Pittsburgh Panthers vs Notre Dame Fighting Irish game on November 15, 2025.
Exclusive

Aaron Donald Exploring Media Future Amid Potential Rams Return

Donald retired following the 2023 season.
Dec 28, 2025; Cleveland, Ohio, USA; Pittsburgh Steelers quarterback Aaron Rodgers (8) looks on after the game against the Cleveland Browns at Huntington Bank Field. Mandatory Credit: Scott Galvin-Imagn Images

Aaron Rodgers Torches ESPN, Fauci, Others on ‘McAfee’

Rodgers didn’t hold back during his half-hour interview.
Jan 21, 2023; Kansas City, Missouri, USA; CBS Sports sideline announcer Mike Florio on field prior to an AFC divisional round game between the Kansas City Chiefs and Jacksonville Jaguars at GEHA Field at Arrowhead Stadium. Mandatory Credit: Denny Medley-USA TODAY Sports

Mike Florio Talks NBC, ‘PFT Live’ Shifts, 49ers Criticism

The “ProFootballTalk” founder returns as a “Football Night in America” analyst.
Huddle in the Hamptons

Why Investors Want to Bring Athletes Into Ownership Groups

LeBron James and Tom Brady have ownership stakes in multiple sports teams.
podcast thumbnail mobile
Front Office Sports Today

8/5/26 – UFC Freedom 250’s $30M Loss, Bijan’s Record Deal, Infantino Losing Support

0:00

Featured Today

FILE PHOTO: Cricket - Indian Premier League - IPL - Mumbai Indians v Chennai Super Kings - Wankhede Stadium, Mumbai, India - April 23, 2026 Mumbai Indians' Suryakumar Yadav in action

India Is Stealing Cricket’s Throne From England and Australia

India’s insatiable appetite for cricket has shifted the traditional locus of power.
WPBL
July 30, 2026

Who’s Playing Women’s Professional Baseball?

Sixty players from 11 countries are descending on Illinois for six weeks.
Tom's Watch Bar
July 17, 2026

Sports Bars Are Cashing In From Summer of Soccer

The World Cup has brought a windfall to America’s biggest sports bars.
Jun 16, 2026; East Rutherford, New Jersey, USA; France forward Michael Olise (11) controls the ball against Senegal during a Group I match of the 2026 FIFA World Cup at New York New Jersey Stadium
July 16, 2026

Where World Cup Stars Go to Customize Their Cleats

The world’s best players turn to a Scottish craftsman for perfect cleats.
July 10, 2026

What the World Cup Means to Erling Haaland’s Tiny Hometown

The tournament’s breakout star is from a rural Norwegian town.
Dec 28, 2017; Portland, OR, USA; Portland Trail Blazers guard CJ McCollum (3) dribbles the ball past Philadelphia 76ers forward JJ Redick (17) and guard Ben Simmons (25) during the fourth quarter at the Moda Center. The Blazers won 114-110. Mandatory Credit:

Why Pro Athletes Are Saying Their Big Contracts Weren’t So Big

“I think people should listen, because they’re telling the truth,” Chris Bosh told FOS.
Aug 31, 2023; Flushing, NY, USA; John Isner of the United States is interviewed on court after his second round match against Michael Mmoh of the United States on day four of the 2023 U.S. Open tennis tournament at the USTA Billie Jean King National Tennis Center.
July 31, 2026

Former Tennis Pro on Influencers at Big Events: ‘Done a Lot for the Sport’

John Isner says there’s upside to content creators’ presence at Grand Slams.
Jul 12, 2026; London, United Kingdom; Jannik Sinner (ITA) serves against Alexander Zverev (GER) (not pictured) in the gentlemen's singles final of The Championships Wimbledon 2026 at All England Lawn Tennis and Croquet Club.
August 3, 2026

Star Withdrawals Test the Value of Tennis’s Masters Events

The Canadian Open is missing tennis’s biggest stars once again.
Sponsored

Saints Great Turns to Ownership

Marques Colston discusses his Champions Fund launch and finding success after football.
July 30, 2026

LeBron Could Make Sixers’ Expiring Jersey Patch a Premium Asset

Philly’s deal with Crypto.com expires in 2027. 
Marques Colston
July 30, 2026

Marques Colston: Why Everyone Is Buying Into Soccer Clubs

Colston’s The Champion Fund invested in Ipswich Town.
Jan 7, 2026; Los Angeles, California, USA; San Jose Sharks center Macklin Celebrini (71) celebrates his goal scored against the Los Angeles Kings during the third period at Crypto.com Arena
July 29, 2026

Macklin Celebrini Contract Extension Sets New NHL Salary Mark

The Sharks locked up their young phenom at a record AAV.
July 28, 2026

John Isner Backs Tennis Players’ Push for More Pay

Stars conducted a 15-minute media boycott at the French Open.