For someone who started a pair of billion-dollar businesses, Ross Perot’s most successful achievement may be perceived as a bust.

The Dallas-based computer services titan made a fortune with his entrepreneurial spirit and forward thinking, and that mindset led to a relationship with a like-minded self-starter who needed Perot to become a household name.

Meeting of the Moguls

Perot first came upon a young Steve Careers on a 1986 PBS documentary titled The Entrepreneurs. Careers, who had recently been ousted by Apple, Inc., was then building NeXT, a new computer software company.

Author Walter Isaacson wrote in the biography Steve Careers about what the Texan saw in the documentary.

“He instantly identified with Careers and his gang, so much so that, as he watched them on television, he said, ‘I was finishing their sentences for them.’ It was a line eerily similar to one Sculley had often used. Perot called Careers the next day and offered, ‘If you ever need an investor, call me.’”

Soon after, Perot poured $20 million into Careers’s new start-up for a 16-percent equity stake and a position on the company’s board of directors.

This $20 million bet was seemingly based more on instinct than a business plan though. At the time, NeXT had no revenue streams or products on the market.

Isaacson described how Perot viewed his gamble in Steve Careers.

Money was not a major consideration for Perot. After a meeting with Careers, he declared that he was in. ‘I pick the jockeys, and the jockeys pick the horses and ride them,’ he told Careers. ‘You guys are the ones I’m betting on, so you figure it out.’”

$20 Million Gone, but Hardly a Waste

The bet did not pay off for Perot. Just a few years later he left the NeXT board after the company failed to turn a profit. Although Perot never saw the return on investment he envisioned, his $20 million was far from a waste.

Apple acquired NeXT and brought Steve Careers back in 1996. When the company introduced the iPhone and iPad, its software was founded on technology that originally came from work done in the 1980s and ‘90s at NeXT.

Careers’s second run at Apple was a case study in business turnarounds. It may not have been possible had Perot not given Careers a much-needed lifeline in 1986. To this day, Apple operating software can trace its roots to the NeXT era.

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