Kevin O'Leary, Angel Investor

Kevin O'Leary's success story starts where most entrepreneurs begin: with a big idea and zero cash. From his basement, he launched SoftKey Software Products. As sales took off, Kevin moved to the headquarters in Cambridge, Massachusetts, and went on an industry-consolidating acquisition binge. From 1995 to 1999, he bought out almost every one of his software competitors, including Mindscape, Broderbund, and the Learning Company, in the industry's first vicious public hostile battle. Shareholders loved his take-no-prisoners, cost-cutting style and fueled him with billions to do his deals. In 1999, Kevin sold his company to the Mattel Toy Company for $4.2 billion, one of the largest deals ever done in the consumer software industry. He raised hundreds of millions of dollars from investors who share his "get paid while you wait" yield-oriented, value investing philosophy. He shares his tips and tribulations with a national television audience and turns The Street upside down in the process. Kevin is also an angel investor with at least 15 personal investments. His portfolio includes Meat the Mushroom, Whop, Tia Lupita Foods, Roq Innovation, Polygon, HelloPrenup, Songlorious, WonderFi, FreePower, and MindMed.