Bernardo Ainza Leapt from Finance to Law

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Bernardo Ainza doesn’t mind admitting that he had some serious doubters. At thirty-six, he was getting ready for his first year of law school. Ainza had spent nearly seven years in banking in the early 2000s—brutal years for the industry. His stint at Lehman Brothers coincided perfectly with the commencement of the organization’s legendary implosion. He arrived at B. Riley & Co. and, later, Bank of America just in time for massive layoffs. Last one in, first one out. Some might have ridden out the tumult, but Ainza thought the world might be trying to tell him something.

“I became disenchanted with the banking industry and decided it was time to take a step back and see what else was on the table,” Ainza recalls. “I had two classmates from business school at USC who had gone the law route and seemed to be flourishing. Frankly, some other colleagues from business school told me going to law school in my mid-thirties was a terrible idea.”

Ainza, current senior legal counsel for PayPal Ventures, the global corporate venture arm of PayPal, seems to have made the right call. After graduating from the University of Chicago Law School, he built his venture capital, M&A, and corporate law expertise at the global law firm Orrick, Herrington & Sutcliffe before moving on to Twentieth Century Fox. In Century City, Ainza worked on one of the biggest deals in entertainment history: the sale of certain Fox assets to Disney for $71 billion. The deal had such public implications that it made it into a joke in Deadpool & Wolverine five years after the sale went through.

After a role with the boutique law firm, Prospera Law, LLP, and another in-house role with Laserfiche, Ainza came to well-known digital payments company PayPal in 2023. A little over a year in, the lawyer has gotten deep into the company’s global startup investments.

“More than 50 percent of the companies we invest in—fintech or fintech adjacent—are outside the US,” Ainza explains. “When you look to burgeoning markets like South America, you’re finding fintech startups seeking to redefine their own markets like PayPal did here in the US.”

The lawyer points to countries like Brazil, whose state-owned instant payment system, Pix, has thus far been adopted by 145 million consumers in Brazil who made more than 36 billion transactions in 2023. That’s almost two-thirds of the country’s population.

The attorney says Central and South American countries are just starting their digital currency journeys. That means entrepreneurs and startups can be part of a massive change aimed at making the transfer of money easier for people from all walks of life.

Working globally has required developing a new set of muscles for Ainza, who says he worked on only a handful of international venture capital investment transactions prior to joining PayPal. In the last year alone, he’s topped that number with transactions in Israel, the UK, Singapore, Germany, India, Uruguay, and Brazil.

With strong reviews, trust built across internal partners, and encouraging feedback from his internal clients, Ainza feels like he’s on the right path. One review sticks with him: “Nothing much to improve on, to be honest.” The comment affirms that Ainza is adding value to PayPal and forging relationships across both company and international lines.

That kind of feedback is “so motivating and pushes me to continue working hard,” the attorney says. “As long as I know I’m helping others and making their roles more efficient—and maybe more tolerable,” he says with a laugh, “that’s enough for me. It helps that I regularly get presented with new opportunities and projects that let me know I’m on the right path.”

What Ainza’s story most clearly highlights is the value of a serious (albeit a well-thought-out) risk. The attorney offers some advice to others who are considering a switch to law, having found themselves in an industry or on a career path that just doesn’t feel right.

“I would definitely advise you to speak to any friends or colleagues who are attorneys,” Ainza says. “It’s valuable to understand what you’re prospectively changing your whole life to do. Understand you’re going to leave school with a hefty amount of debt, so you need to understand how you’re going to finance school and how you’re going to pay off that debt.”

Now well established in his legal career, Ainza dedicates some time to pro bono work that he says PayPal has been incredibly supportive of. He has provided free services to clients at Bay Area Legal Aid and Legal Aid Foundation of Los Angeles. And even with an ACL repair on each of his knees, Ainza still makes an hour’s drive every Sunday to play on his South Bay Peninsula Soccer League team, South Bay FC.

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