Wednesday, May 13, 2026

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

Netflix Deepens Its NFL Ties With Expanded Five-Game Package

The streaming giant significantly increased its presence with the league.
opinion

NFL Should Release Audio on Crucial Replay Decisions

The ACC let viewers in the replay booth last fall.
TNT Sports

WBD Leans Further Into Sports With Paramount Deal Looming

The TNT Sports parent company pushes ahead with its own programming plans.
Apex, NC - February 15, 2026: Portrait of the Super Bowl LXI 61 Football.

ESPN Wants Its First Super Bowl to Be the Most-Watched Ever

Fox’s broadcast of Super Bowl LIX holds the current record.

Featured Today

How Sports Graphic Designers Are Grappling With the Rise of AI Art

The release of ChatGPT 2.0 Images sparked a conversation among sports designers.
May 12, 2026

Collectible Cups Are Sending Sports Fans Into a Frenzy

The drink is secondary to the wild vessel it comes in.
Matt Palumb
May 8, 2026

Pro Lacrosse’s Top Ref Is As Famous As the Players

The last celebrity referee is in the Premier Lacrosse League.
May 2, 2026; Atlanta, Georgia, USA; Atlanta United midfielder Saba Lobjanidze (11) reacts to his goal against the CF Montréal in the first half at Mercedes-Benz Stadium. Mandatory Credit
May 7, 2026

How Atlanta Unexpectedly Became the Epicenter of U.S. Soccer

U.S. Soccer is opening a new national HQ in Georgia.

NBA Player Brandon Clarke Dies at 29

Clarke died on Monday in Southern California, authorities say.
Aug 2, 2024; Nanterre, France; Benjamin Proud (Great Britain), Cameron McEvoy (Australia) and Florent Manaudou (France) in the men’s 50-meter freestyle medal ceremony during the Paris 2024 Olympic Summer Games at Paris La Défense Arena.
May 11, 2026

The Enhanced Games Want to Be More Than a Steroid Olympics

“There’s a benefit for anyone to live enhanced.”
May 12, 2026

Another Summer of LeBron Is Here

James is not under contract for next season.
Sponsored

What Is It Like to Run the Knicks?

Dave Checketts on his time running the Knicks & Jazz, Jordan war stories, and his investment strategy across major sports leagues.
Trick Williams Front Office Sports
May 9, 2026

WWE’s Next Big Star Could Be Ex-NFL Hopeful Trick Williams

The former South Carolina wideout is now WWE’s U.S. champion.
May 6, 2026

Napheesa Collier Admits Engelbert Rant Was For CBA Leverage

The WNBA and WNBPA agreed to a new labor deal in March.
May 6, 2026

U.S. Open Falls Behind Masters in Prize Money: ‘It’s Not a Race’

The Masters increased its purse to $22.5 million this year.
Mar 28, 2026; Miami Gardens, FL, USA; Aryna Sabalenka of Belarus reacts during her match against Coco Gauff of the United States in the final of the women’s singles at the Hard Rock Stadium.
May 5, 2026

Sabalenka, Gauff Suggest Grand Slam Boycott Over Prize Money Share

“Without us there wouldn’t be a tournament,” Sabalenka said.