Guest: Scott McNealy, former CEO and co-founder of Sun Microsystems & co-founder of Curriki

Scott McNealy never wanted to be CEO of Sun, and in his 22-year tenure before selling to Oracle, he knows there were times he failed to execute, or to rein in the once-iconic Silicon Valley firm’s worst impulses. But like his pro golfer son, Maverick, Scott doesn’t like to look back: “Golfers will always look back and blame the wind, a divot that wasn't repaired, a bad rake job, a mower cut that wasn't done properly, a gust of wind,” he explains. “If you blame yourself for all of the mistakes you make. You will hate yourself ... I look forward.”

In this episode, Scott and Joubin discuss Scott Cook, Maverick McNealy, why big companies are riskier than startups, Al Gore, Marc Andreessen, Mark Zuckerberg, Kodak, Dick Kleinhans, Harvard University, “bozo invasions,” Myers-Briggs, making an example, Motorola car phones, the Moscone Center, Elon Musk, Jeff Bezos, NVIDIA’s valuation, farewell letters, “you have no privacy,” open-source education, and toothpaste.com.

In this episode, we cover:

(01:00) - John Doerr
(02:47) - Fathers, sons, and sports
(07:29) - Living in the piñata
(10:48) - Why Scott left Sun
(13:49) - The heyday of Sun Microsystems
(18:24) - Vinod Khosla and founding Sun
(21:24) - How Scott became CEO
(27:21) - Profitable in three months
(30:02) - Inferiority complex
(32:20) - Executive exits and fun at work
(35:49) - Managers and recognition
(38:18) - “HR hero” Crawford Beveridge
(40:35) - How Carol Bartz became VP of marketing
(43:07) - Sharing in success
(45:25) - Scott’s love life & meeting Susan
(50:54) - The dotcom boom and crash
(53:45) - Unicorn CEOs and IBM’s offer
(55:49) - Competitors and hindsight
(58:20) - “The planet system”
(01:00:13) - Too many employees
(01:04:06) - Larry Ellison and selling to Oracle
(01:07:01) - Blaming yourself and looking forward
(01:10:11) - Curriki
(01:12:12) - The AI boom
(01:14:42) - “Grit” and insecurity

Links:

“I knew the one thing I should be was a writer” - Donal Ryan