Omri Casspi has leveled up. The 38-year-old was once a first-round NBA Draft pick after being selected by the Sacramento Kings with the 23rd overall pick in 2009. Casspi (R) went from playing in the NBA to becoming an extremely successful businessmanGettyMaking history by becoming the first Israeli player to ever play in the NBA, Casspi went on to spend 10 seasons playing in The Association, five of which were spent with the Kings over two stints. After being traded in 2011 to the Cleveland Cavaliers, the 6-foot-9 small forward/power forward became somewhat of a journeyman, suiting up for Houston Rockets, New Orleans Pelicans, Minnesota Timberwolves, Golden State Warriors, and Memphis Grizzlies. He was awarded an NBA championship ring by the Warriors after playing 53 games for the team before being waived ahead of the playoffs to create a roster space for Quinn Cook during the 2017-18 season.Of course, that season Golden State, along with their plethora of superstars including Stephen Curry, Kevin Durant, Klay Thompson, and Draymond Green, would go on to sweep the Cavaliers in the Finals. After he was waived by the Grizzlies in 2019, Casspi returned to Maccabi Tel Aviv, where his professional basketball career started, for his third stint with the ball club before officially announcing his retirement from basketball in 2021. Casspi averaged 7.9 points per game, 4.0 rebounds and 1.1 assists in 20.3 minutes of action across 588 games played. Casspi utilized his time with the WarriorsHaving retired aged 33 and making $18 million in career earnings from playing basketball, per Spotrac, Casspi utilized his time being in the league, and the contacts he made, in pursuit of becoming a tech investor. He revealed in a recent interview with Forbes that he first started thinking about life after basketball when he was living in the Bay Area playing for the Warriors. “When I got to the league in 2009, it was very different locker room talk,” Casspi said. “By the time I got to the Warriors later in my career, suddenly it was different. “Steph, Draymond, KD, Andre [Iguodala], folks were talking about investing, ownership, building legacy off the court, and we were getting pitched constantly, being in the Bay Area.It was during his time in Golden State where Casspi really started thinking about his career after basketballGettyCasspi was given a championship ring for his in-season efforts with the Warriors in 2017-18Getty“That’s kind of like where I took the step and made this kind of my life mission after basketball. I wanted to do that when I grow out of the game. “Golden State Warriors was a masterclass of an organization,” he added. “I saw a dynasty from the inside out, what a winning mentality is, the culture, the system, the depth, and essentially that’s kind of what I want to build with Swish.”Entering the tech worldCasspi would go on to found Swish Ventures in 2024 – a venture capital firm that focused on early-stage startups in cybersecurity and Artificial Intelligence (AI). His business philosophy centers around backing founders who enter their respective industries with an unfair advantage when compared to their competition. One of the first investments he made with Swish was with a company called Cognition, which at the time, was valued at $150 million. In 2026, it is now considered one of the world’s fastest-growing AI start-ups, which is reported to be nearing a $1 billion funding round which could see its valuation grow to as much as $47 billion. Michael Jordan is the NBA’s biggest success story when it comes to making money after playing careerGettyLeBron James is one of four NBA players to have achieved billionaire statusGettyBut that’s just one of 20 companies that sits under Swish Ventures’ portfolio, with Casspi usually opting to invest $20 million per company, seen as some by a risky move due to the investment sum being larger than average. “I know $20 million is a large check for the early stages of a company’s life, but I want to find the best opportunities that exist, and in the companies I invest in, I usually put in more money than average,” Casspi explained. “This is a small group of exceptional entrepreneurs.”Swish Ventures currently has eight billion-dollar businesses – also known as unicorn status – under its umbrella, including Upwind Security, which Casspi invested in when it was valued at $65 million. Now, it is valued at $3 billion. “We are at the top of the world in terms of returns on our funds, and after the fundraising at Cognition, where I have been investing almost since the company was founded, the aggregate value of the companies will reach almost $100 billion,” he added. As of 2026, Casspi has transformed the $18 million he made playing in the NBA into assets under management in the range of $800 million, and he doesn’t look to be slowing down any time soon. Fast approaching billionaire status, Casspi will soon join an elite club of just four other NBA players who have achieved the same feat: Michael Jordan, Magic Johnson, the late Junior Bridgemen, and LeBron James. Some list.