Silicon Valley lives off leader lore. Whether truth or myth, the lore forms and perpetuates an image of the leader.

Stories abound how Steve Jobs acted in a particular situation.

The designing of iPhone was not the first time that Steve Jobs put his foot down about this kind of Simplicity. A former director of product marketing at Apple, Mike Evangelist, has told the story of one of his first meetings with Steve Jobs, a meeting that took place in 2000 inside the Apple boardroom.

Mike’s team had been charged with developing a simple way to turn a home movie into a DVD, an app that would later show up as iDVD (one of the iLife apps). He and a partner worked hard to develop their ideas for an interface that would be user-friendly enough for Steve, and prepared to share their work with him by creating all kinds of sample screens and verbal explanations.

Mike was shocked when Steve Jobs walked into the room, ignored their work, and walked right up to the whiteboard. “Here’s the new application,” he said. “It’s got one window. You drag your video into the window. Then you click the button that says ‘Burn.’ That’s it. That’s what we’re going to make.”

Ken Segall, Insanely Simple

While Steve Jobs focused on radical simplicity, Bill Gates was said to test the depth of your knowledge to determine if he could trust your recommendations. In meetings he’d relentlessly ask probing questions, a technique known as dip-sticking. Eventually he’d bottom out your knowledge and either be satisfied or not. If you won his trust, you were free to proceed and gained his esteem.

Here I contribute a few pieces of lore to the canon. The stories are second-hand. Minor details may differ from reality (e.g., it was 20 hours, not 24 hours). Regardless, the lore supports the reputation.

I interviewed a candidate who worked at Tesla. At one point the Tesla build process was taking over 24 hours to complete, delaying development. A group of engineers was selected to improve the situation. Elon dropped in on their project kick off. His ultimatum was that the build must take less than 5 minutes. He’d be checking in daily on the team’s progress. They were incredulous it could be done. They got it down to 30 minutes. Good enough. Elon moved on.

Another time I worked at a company that built internal IT software. We were working to sell Tesla. Elon didn’t like an aspect of the user interface. The sales team joined a call with Elon and our CEO. We weren’t willing to change our roadmap for a CSS customization. We moved on.

Both stories are congruent with Elon’s self-acknowledged nano-managerial style.

Speaking again of build systems, let’s talk about Sergey Brin. Sergey took a different tact from the ruthless grilling of Gates. His humor was a weapon to cajole performance and make a point. A coworker and ex-Googler relayed a story when he was in a meeting with Sergey. One team was reporting out that their build was taking over 30 hours to complete (apparently a common theme across these companies). Sergey remarked,

30 hours? Really?! I can crawl the world in 30 hours.

Tails between their legs, the team fixed their build lest Google crawl the web faster than their team’s build.

Here’s one more as we round third and head for home. Google is famous for the criteria that something must be a $1B idea to even be considered. An ex-Googler shared that Sergey was reviewing the Google Earth Enterprise growth charts with revenue sitting in the low 8-figures. He squinted at the chart and gestured with his finger drawing a line,

Yeah, if I extrapolate way out, we might hit one billion. Though, I’m not sure if I’ll retire before that happens.

Google Earth Enterprise was retired in 2015.