When Edelman was about 13, he got a C on his report card. To whip him into shape, Edelman’s father took him to see John Arrillaga, the Bay Area real estate mogul who made a fortune developing the farmland surrounding Silicon Valley into office space. 

Arrillaga gave the young Edelman a talking-to and asked him an unexpected question. 

“[W]e went into this big old office, [of] this very intimidating, large man who owns the world in the Bay Area. And he goes, ‘Do you make your bed?’” Edelman told Fortune in an exclusive interview alongside his former New England Patriots teammate Rob Gronkowski, with whom he now hosts the Dudes on Dudes podcast. 

(A former Stanford basketball player, Arrillaga stood at six foot four.)

Taken aback, Edelman looked to his father, who urged him to “tell the truth.” The young Edelman obliged. “I go, ‘My mom makes it for me sometimes.’”

That answer did little to satisfy Arrillaga, who to Edelman’s surprise began counting. 

“He counts one, two, three,” Edelman said. “He counts to 15 and he goes, ‘How long do you think it would take to make your bed?’ And I go, “‘I don’t know, maybe a minute.’” 

Here Arrillaga imparted his piece of advice to the young Edelman. 

“You wake up, you accomplish something, and you start the day right,” Edelman said Arrillaga told him. “And from that day on, I made my bed every day of my life.”

As Edelman’s football career progressed, the two stayed in touch. 

Arrillaga was “a huge mentor in my life,” Edelman said.  

When Edelman started to make millions from his NFL salary, he would turn to Arrillaga for investment advice. Arrillaga would give him “old-school” advice like to never have debt, Edelman said. 

Arrillaga made his name in the real estate world, which Edelman says is now his favorite asset class to invest in. 

Starting in the 1960s, Arrillaga, who passed away in 2022, developed much of what would become Silicon Valley by supplying the rapidly expanding tech industry with offices to house the thousands of new workers flocking to the burgeoning tech industry. Arrillaga bought up huge swaths of land in Mountain View, Calif., and San Jose and started developing corporate office parks. His developments would go on to house the offices of companies like Apple, Google, and Intel. Arrillaga would become a fixture of Silicon Valley, donating extensively to his alma mater Stanford. His daughter Laura later married the well-known venture capitalist Marc Andreessen. 

In 2006 Arrillaga and his business partner Richard Peery sold slightly less than half of their portfolio to Deutsche Bank for $1.1 billion. At the time of his death, Forbes pegged Arrilllaga’s net worth at $2.5 billion.    

Edelman said he consulted with Arrillaga when he was 25 and getting ready to make his first major investment, a commercial real estate building in Mountain View. At the time, Edelman was just coming off his rookie deal, a four-year $1.8 million contract, according to Spotrac, which he says he’d saved all of. On Arrillaga’s advice, Edelman went ahead with the deal. 

“I went in as a 25-year-old with, like, 800 grand to my name, put 600 grand down, bought this building,” Edelman said. 

Arrillaga’s advice paid off handsomely, according to Edelman. “That’s been one of my best investments,” he said. “The building’s worth four times [that] now, and that was 11 years ago. And it brings in a great cash flow.”