During the late 1990s, Jesse Itzler was just like any other newbie entrepreneur — he had little cash but big dreams.
Then he made a risky deal that paid off, and it taught him to invest in himself.
At 24, Itzler got an offer that he couldn't refuse: the opportunity to buy four front-row season tickets to the New York Yankees for around $320,000.
Though he had to go into debt to buy the tickets, a then cash-strapped Itzler did it without hesitation — and he says it paid off big time.
Itzler, now 51 and a successful entrepreneur worth millions (even before he married billionaire Sara Blakely in 2008), said taking that risk during his early days helped set him up for success.
He reminisced about the once in a lifetime opportunity on Instagram to encourage young people to bet on themselves.
"When I started Alphabet City Records I was 24 years old. I was creating theme songs for pro sports teams and my partner and I went to pitch the NY Yankees," Itzler wrote on Instagram on April 7.
When the meeting was over and Itzler said he got the offer of a lifetime.
"As we were leaving the meeting the [Yankee's chief marketing officer] said 'Hey, we have four tickets for sale that just opened up in the front row. Want to buy them?'"
The Yankee executive went on to explain that the seats were "specially made" for elite guests and there were only eight of them in the entire stadium.
What's more, the seats were "built directly onto the field for the World Series."
"How much?" Itzler said he asked.
"I don't recall the exact amount but I believe he said they were $320,000 for the season," Itzler wrote.
While blown away by the cost and despite having less than $10,000 to his name and only $45,000 in his business bank account, Itzler immediately agreed to buy them.
"[M]y total net worth was probably less then $10k. NO, it was DEFINITELY less then 10k! However, I said 'we'll take them,'" Itzler wrote.
He and his business partner fought about Itzler's rash decision for hours, he said.
But he said there was a method behind his madness.
"Anyone could take a client to a good restaurant in New York, but there are only 32 of these seats in the world. I knew we'd make our money back 10x by giving these to clients and entertaining...it was like beach front real estate," Itzler wrote.
Itzler also knew those seats would "NEVER be available again," he said.
So Itzler and his business partner borrowed money from a friend for the down payment and took out a loan for the rest.
One year after buying the seats, Itzler and his partner closed the sale of their first company in those seats, he said.
"The buyer went to every game of the World Series that year," Itzler wrote.
And according to Itzler, years later he took Shawn "Jay-Z" Carter and his business partner to a playoff game ahead of the 2007 World Series, and continued to split the seats with the pair for years. Itzler also said that after he co-founded private jet leasing company Marquis Jets, Jay-Z booked the company to a provide a plane for one of his world tours. (Carter did not immediately respond to CNBC Make It's request for comment.)
In the end, Itzler estimated that those four seats resulted "in a 50x return on investment."
While he is happy that he took the risk early on his career, he is not suggesting to other entrepreneurs to "go into debit over tickets." But there is a lesson in the story: It's crucial to "bet on yourself," he said.
Correction: This story has been corrected to reflect that Itzler took Carter to a playoff game ahead of the 2007 World Series.