- Kevin O’Leary became a millionaire after selling his software company Softkey to Mattel for $4.2 billion in 1999, but says the moment felt anticlimactic. Despite his massive success—including roles as an investor on Shark Tank—he emphasizes that true success comes from passion and discipline, not chasing money. O’Leary reflects that earning his first million was the hardest milestone, but once achieved, larger financial goals became easier.
Although Kevin O’Leary became a millionaire more than 25 years ago after selling his software company Softkey Products to Mattel for $4.2 billion in 1999, he said he still remembers the exact moment he made it big.
