Shaquille O’Neal‘s “Big Aristotle” brain rarely glitches in business. He invested in Google years before it became a giant. But big fella missed two massive opportunities sitting right in his recording studio at his Orlando house. Both Backstreet Boys and NSYNC recorded their first album at Shaq’s house when he was still with the Magic, but he didn’t think they would quickly break records.

Somehow, AJ McLean, the founding member of BSB, formed in 1993, believes that it was the right decision for the band not to sign with the Magic legend.

“I don’t know what would have happened if we went that route,” McLean said. “No disrespect to Shaq, because I love him to death, but don’t think we’d be where we are today necessarily.”

“I think we might have made the right decision,” he added.

“It was one of my worst music career mistakes ever,” he told Sean Evans on “Hot Ones.” “I could’ve signed them and Backstreet Boys. I think I let them record in my studio for $1, but I just didn’t understand their music. My biggest mistakes [are] not investing in Starbucks, not signing NSYNC and Backstreet Boys.”

Interestingly, Lance Bass, the bass singer for NSYNC, told TMZ a few years ago that it would have been great had Shaq signed them. So far, Backstreet Boys have sold over 100 million records, and NSYNC has sold over 70 million. No wonder Shaq continues to regret the opportunity that was right in front of him at his home.

But a few missed opportunities didn’t derail Shaq’s plan to build a financial empire. He is no slouch in the business world, sitting on a total worth of almost $500 million, and he is still building.

AJ McLean reveals how Shaquille O’Neal helped him feel comfortable in picking a new style

Orlando Shaquille O’Neal was a scary beast on the basketball court. Shaq was the ultimate combination of raw athleticism and power that was too much to handle for opponents. Away from the basketball court, he was also a talented artist. His debut album, Shaq Diesel, went on to get the platinum certification.

It is not unfathomable to imagine what impression a man of Shaq’s stature would have had on those young Backstreet Boys. But giving someone the confidence to paint toenails isn’t something that comes to mind first. McLean gave a bit of an anecdote about how Shaq gave him the confidence to paint his nail. He recalled looking at Shaq in his flip flops and toenails painted red at his Orlando home.

“Maybe that’s what started for me. I don’t know,” he told TMZ. “Now that I think about it, maybe that was the catalyst for me to feel strong enough in his manlihood to paint my nails.”

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Perhaps McLean didn’t know why Shaq paints his nails. “I paint because it’s ugly and I want to look pretty,” he admitted on his “Big Podcast” last year. Last year, he told Jimmy Fallon that he started painting his nails because he had some paint left from the day his mother painted his toe after an injury.