Venture portfolios tend to lose money on a large share of their bets and make it back on a few. Alejandro Betancourt López, who runs the O’Hara Administration family office, describes his own book in exactly those terms. He puts the ratio at two out of 10.

“When you have a portfolio of 10 investments and they’re all very, very high stakes, big return or nothing, if two of them goes well, they pay for the eight and make you a good profit for everything else,” he said in a conversation about his family office.

Alejandro Betancourt López’s O’Hara Filter

Asked to describe the philosophy behind O’Hara, he kept it short. “Anything that is sexy and makes money and that gets you a good challenge. We like challenging environments. We like to innovate and be first,” Alejandro Betancourt said.

Alejandro Betancourt López applies that filter through O’Hara Administration, the holding group his résumé lists for stakes in consumer, transport, sports software and banking companies. “I consider myself a very high risk taker, a massive risk taker,” he said.

A portfolio built that way accepts that most positions will disappoint. The few that work have to be large enough to cover the rest.

What Venture Data Says About the Ratio

Correlation Ventures, which keeps a database of venture financings and their outcomes, reported in July 2023 that nearly half of financings lost money for investors over the previous decade. Thirty-seven percent of exits returned less than the capital put in.

Less than 4% of the capital invested in venture-backed companies generated a return of 10 times or more, the firm found. A fund that misses that slice has little room to recover. One that catches it can absorb a long list of losses.

Uber bought 30% of Auro, the license company Alejandro Betancourt López co-founded according to his résumé, for €220 million in February 2025.

Positions that go wrong often stay in the portfolio for years. Some of them, held long enough, “come back at par,” in his words, and return the money that went in. He keeps working on those too. “I never leave them alone. So I try to support them all the way,” he said. Running a book like that, he said, is “a matter of getting a good sense how well positioned you are in the different things that you’re doing.”

Would You Lose Your House? Alejandro Betancourt López’s Test

A blunt question from a friend shaped how Alejandro Betancourt López sizes his bets. Before committing to a deal, he pictures the worst outcome and asks whether he would still be on his feet if everything went wrong.

“Are you gonna lose your house over an investment? No. Okay. Then you build on that,” he said in 2023 when asked how he decides how much risk a deal can carry.

Starting From the Failure Rate

“90% of projects that are started fail,” Alejandro Betancourt said. “And that’s something you gotta live with.” Alejandro Betancourt López made the point while explaining why founders need a plan for losing before they start.

Federal figures show how common failure is even for ordinary companies. Of U.S. private-sector establishments born in March 2013, 79.6% were still operating a year later and 50.6% after five years, according to the Bureau of Labor Statistics. Nearly one in five closed within the first year. That was the steepest annual drop in the decade the agency tracked. The data covers every kind of new business, from restaurants to accounting firms.

Alejandro Betancourt López’s Homework Before the Leap

Accepting that most projects fail does not mean jumping blind, in his telling. “You have to take risks, but you need to do your due diligence. You need to do your homework,” he said in an October 2020 interview about Auro, the ride-hailing license business he helped start according to his résumé.

A good risk taker, he said, is “completely aware of the risk you’re taking” and knows where they will end up if it goes bad. Someone who works that way can take a loss “and be the next day, ready to the next challenge.” A bad one thinks, “I’m going to jump down the base, and see what happens. Maybe somebody will catch me, and take me to the moon.”

“Nothing risked, nothing conquered,” he said, calling it a popular saying. Then he added a second rule. “Expect the best, but prepare for the worst.”

Sizing a position so that its failure would not cost the family home keeps one loss from ending the next attempt. Alejandro Betancourt López applied the same thinking to Auro’s early license purchases. He has called them a high-risk bet, made before Uber and Cabify needed permits at scale. “We were confident, but were not certain that this will happen,” he said.