Don't get me wrong, he is one of my fav people. He is the only bona fide billionaire on Shark Tank. I like his approach to business. His selling of broadcast.com to Yahoo at the height of the cotcom mania was genius and the subsequent option play to protect its sales price was one of the best option trades ever. That being said, let's look up how much money he made with all those investment in the last 2 decades, shall we? He got 6 billions from Yahoo. I am not sure how much taxes he had to pay on it, I am guessing there was some tax tricks played, so maybe 20%. That gave him 4.8 Billions 20 years ago. Now let's see his current net worth: "Forbes Magazine estimates Mark Cuban's net worth to be $4.4 billion.Apr 14, 2021" Wowsie!! So after all those years and businesses he invested in, he literally made nothing. In 20 years as a well renowned business man and expert investor, his net worth is still the same. Well, at least he didn't lose a big chunk of it, that has to count for something. Still, I expected some growth there...
Venture capital is kind of like trading, you have to just put your money out there and hope your wins will be bigger than your losers But I agree 20 years and no big wins? A family friend made over 500x on a $250k angel investment
Ryan Reynolds is a better investor. He made $400 million on his tequila if I am not mistaken. Hell, he does not have to make another movie ever again. Mark Cuban got lucky when his tech savy friend created a company which they sold for hundreds of millions. He is actually, a salesman which is why he is so slick. A lot of it is connections. Who you know as opposed to what you know. Al Gore got a $500 million bonus when he joined the Apple Computer board. He got call options for just $2 each. Of course, he cashed in. Even Hillary Clinton pocketed $200,000 on cattle futures of all things. Someone connected to her, gave her that win. Even Ashton Kutcher made out like a bandit in one of his venture capitalist deals. All I remember is he made a ton of monies.
I've seen him on interviews on Fast Money and the Halftime Show on CNBC and he doesn't seem to be a real big risk taker. His investment advice is to just go long the FAANG trade. He rarely ever talks about the high growth stocks which is strange since that is what Shark Tank is all about.
I know 2 billionaires and several multi millionaires. They almost all got rich from 1 big deal. Most of them were never able to repeat that success ever again. Some of them even lost lots of money trying to. I only know one who managed to build 2 new companies after selling his first one, and to sell them from a huge amount of money. I also know about 1 famous and rich football player. He was really good in football, but he thought he was a good businessman too. He lost millions in two attempts to start some business.
Why not ask him? He is on here from time to time. https://www.elitetrader.com/et/threads/right-now-is-the-time-for-action.344482/#post-5094208
Cuban's cut on the sale to Yahoo was $1.4B. Since the Yahoo shares they received had a lock up on them, he protected it with options. https://libertythroughwealth.com/2018/08/23/mark-cuban-protected-his-fortune-with-options/ Knowing this is what he got from the sale provides a better idea of how much he has increased his net worth since then.