![](\"https:\/\/fortune.com\/img-assets\/wp-content\/uploads\/2025\/07\/GettyImages-2212123752-e1751556647508.jpg?w=2048\")
<\/p>\n<\/p>\n
Although Kevin O\u2019Leary 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.<\/p>\n
\u201cI get asked all the time, do you remember the moment that you became a millionaire? I do,\u201d the Shark Tank star known as Mr. Wonderful said in a video posted to his LinkedIn in July. \u201cBut have to admit, it was very anticlimatic.\u201d<\/p>\n
How Kevin O’Leary built his fortune<\/p>\n
O\u2019Leary founded Softkey in 1986, and throughout the 1990s his company acquired its biggest competitors like Compton\u2019s New Media, the Learning Co., and Minnesota Educational Computer Co. as well as Creative Wonders, Mindscape, and Broderbund. <\/p>\n
This helped Softkey to become the world\u2019s leader in educational, reference, and home productivity software and the second-largest consumer software company in the world at the time with more than $800 million in annual sales, 2,000 employees, and subsidiaries in 15 countries.<\/p>\n
While O\u2019Leary\u2019s accomplishment in selling Softkey to Mattel and becoming a millionaire may seem like a major deal, he said it didn\u2019t feel that way. <\/p>\n
\u201cBoom, you wake up one day and you say, \u2018Wow, this is interesting, but it doesn’t change anything,\u2019\u201d O\u2019Leary said in the LinkedIn video. \u201cThat’s the crazy thing. And every millionaire [or] billionaire I talk to says, \u2018Yeah, it’s not that big a deal.\u2019\u201d<\/p>\n
But that may be O\u2019Leary reflecting on the entirety of his career. In 2003, he became co-investor and director in Storage Now and a founding SPAC investor and director of Stream Global Services in 2007. <\/p>\n
He now holds investments in more than 30 private-venture companies, and is the chairman of O\u2019Shares ETF Investments and automated internet-based investment advisory service company Beanstox. And, most famously, he\u2019s been an investor on Shark Tank since the show\u2019s premiere in 2009. O\u2019Leary also owns several companies he founded, including O\u2019Leary Fine Wines and O\u2019Leary Ventures, his private venture-capital investment company.<\/p>\n
Why the first million is the hardest<\/p>\n
While becoming a millionaire feels like a blip on O\u2019Leary\u2019s radar at this point, he also said in a 2023 video on his YouTube channel that it can feel impossible to make your first million\u2014but meeting a $5 million milestone feels much easier.<\/p>\n
\u201cYou work your ass off. It\u2019s so hard. What it really takes to do is have the discipline of not buying s*** you don\u2019t need,\u201d O\u2019Leary said in the YouTube video. \u201cTo make that first mil is you\u2019ve got to invest it. Market\u2019s going to make you 8%. And then I thought, well my sights are on five [million]. It\u2019s going to be impossible. It wasn\u2019t as hard to get to five [million] as it was to one [million].\u201d<\/p>\n
And even though O\u2019Leary has an estimated net worth of about $400 million and pushes pitchers on Shark Tank to really know their numbers and prove their valuation, he insists it\u2019s not about the money to him.<\/p>\n
\u201cIf you’re very passionate about what you’re doing [you\u2019ll] wake up one morning successful,\u201d O\u2019Leary said in the LinkedIn video. \u201c[The] key is the passion. It\u2019s not the pursuit of greed or money. That doesn\u2019t work. You’re so in love with what you’re doing in business, and you get rewarded for it, particularly if you’re solving a big problem.\u201d<\/p>\n
More on Kevin O’Leary:<\/p>\n
Shark Tank\u2019s Kevin O\u2019Leary says if he were 25 today, he\u2019d chase these two booming opportunities in the world of AI<\/p>\n
Shark Tank\u2019s Kevin O\u2019Leary doesn\u2019t care if you work from your basement. He just wants to know if you can \u2018execute\u2019<\/p>\n
\u2018What a waste of money\u2019: Shark Tank star Kevin O\u2019Leary urges couples to ditch the extravagant wedding and do this instead<\/p>\n
This story was originally featured on Fortune.com<\/p>\n
#Kevin #OLeary #millionaire #billion #dealbut #anticlimactic<\/p>\n","protected":false},"excerpt":{"rendered":"
Although Kevin O\u2019Leary became a millionaire more than 25 years ago after selling his software…<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":[],"categories":[245],"tags":[4836,552,4835,640,92,1584,4834,2566,1629,583],"_links":{"self":[{"href":"https:\/\/stock999.top\/index.php?rest_route=\/wp\/v2\/posts\/2049"}],"collection":[{"href":"https:\/\/stock999.top\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/stock999.top\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/stock999.top\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/stock999.top\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=2049"}],"version-history":[{"count":0,"href":"https:\/\/stock999.top\/index.php?rest_route=\/wp\/v2\/posts\/2049\/revisions"}],"wp:attachment":[{"href":"https:\/\/stock999.top\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=2049"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/stock999.top\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=2049"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/stock999.top\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=2049"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}