Omri Casspi still remembers the date—January 27, 2024—when he hosted Cognition AI cofounders Scott Wu and Steven Hao at Chase Center in San Francisco for a game featuring his former Golden State Warriors teammates. That night, star point guard Stephen Curry put up 46 points in a double-overtime loss, but Casspi was captivated by the show taking place in his suite: Wu’s startup pitch for an AI coding agent that would allow other companies’ engineering teams to write code much faster.
“I grew up doing competitions as well,” Wu, who won three gold medals at the International Olympiad in Informatics as a teenage programming prodigy and was introduced to Casspi by mutual friends as the former NBA role player was establishing himself as a venture capitalist, says, somewhat tongue-in-cheek. “My whole thing was competitive math and programming—maybe a bit lesser known than the competitions that Omri was involved in. But you can really feel it from him that he just hates losing.”
Luckily for the 38-year-old Casspi, he has been on quite the winning streak. A stroll through Palo Alto with Wu the next morning led him to participate in Cognition’s seed round in early 2024, which valued the startup at $150 million. Today, it is one of the world’s fastest-growing AI startups, reportedly nearing a $1 billion funding round that would peg its valuation at $47 billion—and it is just one of eight billion-dollar businesses among the 20 companies in the portfolio of Casspi’s Swish Ventures, an impressive hit rate for a VC firm focused on early-stage startups.
On Thursday, Swish is announcing its latest big win: The Tel Aviv-based firm, which Casspi launched in 2024 after it absorbed his earlier fund Sheva, has raised its third and largest fund to date, drawing $250 million from backers including Sequoia Capital and several large U.S. pension funds and endowments. The fresh capital will push Swish’s total assets under management to about $800 million, with its investments primarily in the AI infrastructure and cybersecurity industries.
Casspi, who spent a decade in the NBA and retired from pro basketball in 2021, sees his experience with Wu as emblematic of his approach to investing. “He can build whatever he wants—I just wanted to be in business with Scott,” he says. “We want to invest in ‘spiky’ people, folks that have an unfair advantage to a certain extent in their industries and have a cutthroat mentality.”
But while Casspi refers to Wu as “one of one,” others have had the same impression of the 6-foot-9 Israeli-born former forward.
“I’ve known a lot of people that were very elite in one thing, and then when they try to go into investing, it’s like a retirement job for them,” says Shaun Maguire, a partner at Sequoia who met Casspi in 2023. “Omri is one of the first people I’ve ever met who was world class in one thing and then went into venture capital and took it as seriously as he took the first thing.”
That dedication was evident early. After growing up in Yavne, a small town about 20 miles south of Tel Aviv, Casspi made his professional debut for the Israeli Basketball Super League’s Maccabi Tel Aviv at age 17 in 2005. Four years later, he became the first player from Israel to reach the NBA after the Sacramento Kings selected him with the 23rd overall pick in the draft.
Casspi, who averaged 7.9 points per game across his NBA career, played for seven teams in ten years in the league, but none made as much of an impact on his plans for life after basketball as his one season with the Warriors, in 2017-18. Teammates like Curry, Kevin Durant and Andre Iguodala traded ideas in the locker room about their investment portfolios and the pre-IPO startups they were being pitched. Silicon Valley entrepreneurs and venture capitalists regularly sat courtside and schmoozed with players.
For Casspi, picking winners and investing in these entrepreneurs seemed like the second-best job in the world, after playing basketball.
Golden Opportunity: Casspi spent just one season with the Warriors, but it was formative, connecting him with Silicon Valley entrepreneurs. These days, he often gets a suite for games to host business contacts.
Nhat V. Meyer/MediaNews Group/Bay Area News/Getty Images
“There are so many similarities between being an athlete and being an entrepreneur,” says Casspi, who was waived by the Warriors that April amid a roster crunch but still received a championship ring after Golden State went on to sweep the Cleveland Cavaliers in the NBA finals. “There are disputes and arguments, and it’s sort of like a locker room. At the end of the day, you put your hands in and go out and have to win together.”
Casspi earned $18 million in salary as an NBA player, finishing his career in 2019 with the Memphis Grizzlies before playing two more years back in Israel, and he had access to a lot more than that through his connections with team owners and Bay Area entrepreneurs, pooling together enough capital to raise his initial $36 million fund, called Sheva, in 2022. His first investment was in Upwind Security, founded that year by Amiram Shachar, whom Casspi had befriended years earlier at an informal meet-and-greet with Israeli entrepreneurs after a Warriors game. At the time, Shachar had been running a cloud management startup called Spot, which he sold to NetApp in 2020 for $450 million.
Upwind, an AI security platform to detect and combat cyberattacks in real time, was valued at $65 million in its 2022 seed round and has grown to unicorn status, with a $1.5 billion valuation in its Series B round in January. Now, it’s reportedly closing in on a $300 million investment that would lift its valuation to $3.8 billion. Other billion-dollar startups in Swish’s portfolio include Eon, a cloud-backup startup valued at $4 billion in December, and Applied Compute, founded just last year by former OpenAI staffers and valued at $1.3 billion in a funding round in April.
In 2024, Casspi brought in Ori Streichman as a partner, and they launched their first fund under the Swish Ventures name that year, raising $63 million and writing their first check for Wu’s Cognition. Streichman, 27, stood out to Casspi for his achievements as a world-ranked chess player on Israel’s national youth team, followed by five years of service in a prestigious intelligence unit in the Israel Defense Forces.
Swish raised a second $100 million fund at the end of last year and will now move forward with investing out of its new $250 million fund, targeting seed and Series A investments in around 12 companies to average about $20 million per investment. Those will be larger checks than Casspi has dished out for previous funds, but he expects his process to stay the same—identifying and supporting founders who share his competitive spirit.
About half of Swish’s portfolio is based in Israel or has significant operations there, and Casspi predicts a company worth $100 billion will emerge from the startup community in Tel Aviv in the next decade. He also travels to the U.S. almost every month, staying for about a week per visit to meet with founders and investors in New York or Silicon Valley.
Sequoia’s Maguire marvels at the Swish founder’s ability to introduce startups to customers, with Casspi often getting a suite at a Warriors game or hosting dinners to connect a group of founders with chief information officers at major companies. Wu also says Casspi is an effective recruitment tool for Cognition, always willing to get on the phone to close the deal with job candidates if they happen to be basketball fans.
“I was very fortunate to play alongside first-ballot Hall of Famers, and when you see elite success up close, you recognize a pattern where essentially you want to recognize the same pattern in the founders,” Casspi says. “For us, the founders are our stars, and we’re there to support them. It’s their show, obviously, and our job is to set screens and show up in moments that matter.”
Leave a comment