Scott McNealy on breaking the rules

Sun Microsystem co-founder and chairman shares his life and business lessons

Back in the 80's, Scott McNealy and Vinod Khosla founded a company called The Data Dump, which Scott told me was a "huge disaster." But as one idea failed, another took off. That other was Sun Microsystems. Together with Vinod, Andy Bechtolsheim, and Bil Joy, the foursome raised about $200,000 to start Sun Microsystems. Scott served as CEO from 1984 to 2006, and brought Sun public in 1986.

In this "Lessons learned" segment, Scott advises entrepreneurs to "hang out with really smart, innovative, super bright, off-the-charts people and stay at the party as late as they do and become their best friends." Apparently, it worked for Scott, who spent late nights with Vinod at many parties.

Besides hanging with the right crowd, Scott also advises entrepreneurs to "break the rules of business."

Look for ideas that are "off the beaten path of conventional wisdom," and not "intuitively obvious." 

The more people it's not obvious to, he said, the better chance you have. 

At the same time, Scott says don't "cut corners on legal and moral issues." 

"Break the rules of business," he said. "but not the rules of the land." 

Additionally, Scott said not to worry too much about raising capital. "Bill Joy says there's never been a successful well-funded startup. If you're well-funded, you'll do it the old way.  If you don't have a lot of money, you'll find a new and efficient way... Don't look too hard for too much money - it'll force you to do things the wrong way."

Finally, Scott suggests that entrepreneurs wait to get married. Scott got married at 39 years old. He also talks about why your decision about a spouse is far more important than any business decision you'll ever make.

[Note: For more on Scott's advice, check out his Vator profile and the video I shot of him giving the keynote at  The Plug and Play Expo last week.]