You just can't compare him to Gates who got where he is today through a combination of luck at birth and supremely hard work (and some questionable business tactics).
$1.1 billion to $4.08 billion [1].
His primary business holding, the Dallas Mavericks, has increased in value from $285 million to $1.9 billion [2] (per the latest Forbes estimate). For that investment, he has seen a rate of value increase of about 11% per year. That investment stomps the S&P 500 massively (which was at ~1400 when the acquisition closed).
[1] https://www.bloomberg.com/billionaires/profiles/mark-cuban/
[2] https://www.forbes.com/sites/kurtbadenhausen/2018/02/07/nba-...
Very few money managers that are accessible to people with less than 10^8 USD can beat the S&P after fees.
Bridgewater, (Ray Dalio's fund mentioned above) regularly gets 12.5% annual returns and they are most notable for being consistent, not high. Pre-2008 some investment banks were getting up to 20%.
A billionaire making 7.5% annually is fairly unimpressive if their goal was to make money (which it might not have been for Cuban).
From that article: "After the IPO, the company was worth $1 billion, Mark Cuban was worth $300 million" (obviously a little more than the $100m I thought)
Cuban's position was worth more on paper at its peak before the Yahoo acquisition. Broadcast.com was acquired for $130 per share, the high that year before the acquisition, was $144 per share.
Prior to the acquisition, the stock was trading at $118. Yahoo only paid a 10% premium. Cuban was worth over a billion dollars before the acquisition.
https://www.cnet.com/news/yahoo-broadcast-com-sizzle-after-d...
The S&P 500 was 1300 when he sold to Yahoo. He received $1.4 billion of Yahoo (14.6m shares at $95/each). He had to pay taxes on clearing out that position as well, so you can safely assume his after tax position was more like ~$1.1 billion. He very solidly beat the S&P 500.
He's worth $4.08 billion today according to Bloomberg (ranked #500 on their global rich list). He has increased his net worth by nearly 4x.
The S&P 500 is at 2747. It has just over doubled since April 1999. He'd be missing a billion dollars if he had gone with the S&P 500, including any dividends.
He was better off with what he did, he beat the S&P 500 index fund. Not only did he make more money his way, he got to do what he wanted to with his money, such as buying the Mavericks.
He's overexposed too. There's something about people like Gates who don't make a lot of public pronouncements. When they speak, you tend to think it's because they have something of value to say (and they generally do).
Probably doesn't hurt that they also let their work do most of the talking for them (e.g. Bill and Melinda Gates Foundation).
I take the advice of anyone with a huge grain of salt.