4. Mark Cuban – Box
Mark Cuban is worth billions, so chance are he isn’t really sweating any missed opportunities, because they’re not going to make or break him. However, there’s one company in particular that could have made him a bundle.
Box, an enterprise cloud company, was started by college student Aaron Levie. Levie pitched Cuban, who initially gave him a $350,000 seed investment for his company. However, Cuban didn’t quite agree with the young tech company’s business model, and after some disagreements, Levie managed to raise enough to buy the billionaire out. Cuban stands by his decision, continuing to comment that he doesn’t agree with Box’s business model, but the company’s success without him proves he may have been able to pocket a nice chunk of change had he stayed.
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