Entrepreneurs

Daymond John tells shy airline passenger: You should have talked to me on the plane

Daymond John on CNBC's "Mad Money."
Scott Mlyn | CNBC
Daymond John on CNBC's "Mad Money."

There's nothing worse than a missed opportunity.

Daymond John will the first to tell you that.

On January 22, the entrepreneur and star of ABC's "Shark Tank," did an "Ask me Anything" question-and-answer session via Reddit, during which user Supersix4our recalled a situation where he or she could have said hello to John, and opted not to.

"I sat next to you on a flight from LAX to BOS last year. I didn't want to bother you because typically celebrities hate being bothered all the time. I had so many questions that day, but left you alone," Supersix4our wrote. "Should I have just talked to you, or do you prefer privacy when traveling?"

John, who goes by the username TheSharkDaymond, says it would have been fine with him to have been approached.

"Thank you, but I remember that flight and was feeling talkative. You miss 100 percent of the shots you don't take," John responds.

"Figures, lol. Thanks for the response, I'll be sure to say something next time. You've been a big inspiration to me for many years," Supersix4our says.

John is the not the only shark who knows the value of opportunities like this. Consider his co-star Mark Cuban. The tech billionaire has more than once invested in entrepreneurs who cold-emailed him.

Blue Origin engineer Tim Ellis and SpaceX engineer Jordan Noone snagged a half-million-dollar investment from Cuban doing just that.

"We actually raised our seed round from Mark Cuban — which was a cold email — a week after we said we are starting the company," says Ellis, speaking at the CB Insights A-ha Conference in December. "Yeah, we cold-emailed Mark Cuban with the email tagline, 'Space is sexy: 3D printing an entire rocket,'" says Ellis — Relativity Space, the company he and Noone were pitching, 3D prints rocket parts. "It was two months of due diligence after, but he gave us half a million dollars," says Ellis.

And when high school dropout Adam Lyons cold emailed Cuban about his insurance rate comparison start-up, The Zebra, the then-25-year-old got an answer 20 minutes later. Lyons didn't even know Cuban's email address when he decided to reach out to his dream investor — he guessed.

Cuban and Lyons emailed back and forth for the next several weeks and eventually Cuban made an investment (for an undisclosed amount).

Lyons says the keys to getting a response from Cuban were to keep his email short, be himself, be excited, come to the table with work already done and don't try to close the deal on the first go. At a certain point, though, reaching out to a celebrity will always involve a moment of "going for it."

"Then you just have to do it," says Lyons, speaking to CNBC. "You can't be afraid. You don't want to overthink it."

See also:

Mark Cuban says that his best life hack is saying yes to email and no to meetings

How a 25-year-old high-school dropout cold-emailed Mark Cuban and got an investment

5 tips for writing a great cold email from a guy who got Mark Cuban to reply in 20 minutes

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Disclosure: CNBC owns the exclusive off-network cable rights to "Shark Tank."