Jamais Vu

When people learn I worked at Microsoft for over 20 years, retiring as a Director¹, they want to know if I ever met Bill Gates and yeah, I did. I also met Steve Balmer who succeeded him as CEO, as well as Satya Nadella, Microsoft’s current CEO.

All side eye’s on you Steve

I joined Microsoft and attended my first company meeting in 2001. After a full day of sessions and pep talks from company leaders including Bill, I had my first run-in with him on the beach that night. Sounds romantic but no, I was roaming the fringes of the after party with beers and work teammates when we spotted Bill off walking by himself!

We got so excited, whispering and pointing like we were back in elementary school. “Lookit! Is that really BillG!?”

Dropping our voices and straightening our backs, we subtly switched course to intercept him for a greeting that would surely and immediately elevate our career trajectories. Bill nodded at us with a smile more like a grimace, while looking vaguely off at a point well above our heads, not missing a step. Dude is a hard core introvert.

Also an asshole. Stories abound at Microsoft about how fiercely competitive and confrontational Bill is in internal meetings. Although Bill passed the CEO hat to Steve Ballmer in 2000, he remained the public face of the company as Chairman and Chief Software Architect. While Bill began to focus more on his foundation especially after Satya Nadella took over in 2014, even in 2021, when I left, BillG reviews were frequent, high profile, urgent events that shaped company direction.

At one point, I worked as an architect for early adopter programs (testing and validation of pre-release software) and in that role I sponsored a number of companies. Part of that gig was escorting these company CEOs around at our launch events. BillG did the keynote for one of these and stuck around to spend 1-on-1 time with each CEO. My job was to usher my buddy CEO over to Bill at the appointed time for a warm handoff.

This was interesting, because while he was a dismissive jerk to me (and his exec admin shadow), he had to immediately pivot, smile and talk nice to the CEO I brought as offering. Two faces. These guys have their public persona and image, but make no mistake, in private they all have a big chip and a sharp edge.

Steve, I met in passing. He was in San Francisco for some meetings/PR and he gave me an effusive greeting and an enthusiastic hand shake. I was worried he was going to hug me. My most vivid memory of Steve is sprinting out onto the big stage with a little bear-shaped honey container in his ham hands that he squeezed down his gullet between rants, so his voice wouldn’t give out while he screamed and ran around high-fiving the crowd².

I met with Satya before he was promoted to CEO. He was much more level and thoughtful, with perhaps the least variance between his public and private personas. However, late in my career I would regularly get inserted into an email thread with Satya, who was now Microsoft’s CEO. It was always a problem forwarded from a disgruntled customer and you could tell he had the same combative, get-it-done-whatever-it-takes-just-tell-me-when-it’s-fixed characteristics that Bill and Steve were known for.

It’s odd meeting public people in real life, and CEOs, especially Bill Gates caliber, are celebrities. Same with our current evil triad of tech bros: Elon Musk, Jeff Bezos and Mark Zuckerberg.

As a kid growing up in Hollywood, I got familiar with celebrity run-ins from an early age. I saw Fonzie (Henry Winkler) eating Chinese food by himself at our neighborhood hole-in-the wall place.

I whispered (loudly) to my sister “Fonzie likes Chinese Food?!” She said ‘Ayeeeeee 👍’

Later I’d serve Mr-T popcorn (I pity the fool!), watch Slash thrash around playing guitar in the quad at Fairfax High (GnR🤘), and ask Mario Van Peebles, sitting a couple tables over, for an autograph for my girlfriend.

I reached the pinnacle of celebrity rubbing elbows when Eddie Murphy came into Swensens and I made him the best Mint-Chip milkshake he’d ever had.

Generally celebrities fall far short of what we imagine. But once in college, we ran into one of Cal’s basketball players rafting down the Sacramento River. Seeing a 7 foot tall guy up close and personal is a whole ‘nother kind of jamais vu. There would be no high-fiving Sean.³

I hit peak executive connection three years before I left Microsoft. I left my old position to build a new team and I gave no fucks. I had grown out of my prior role and was going to make a change regardless, even if it meant leaving Microsoft.

For about a year, I was only four levels from Satya.⁴ One of the smartest guys in the company—a BillG vintage exec—led up our group and he was so volatile, no one dared sit near him during reviews. He was a big guy and he always sat in the same spot in his exec conference room, often chomping on a fried egg sandwich, and he would go off unexpectedly, talking loud and fast, gesticulating wildly, jumping up to scribble on the whiteboard behind him, every time he spotted a flaw in math or logic or designs that were not to his liking.

He could yell and dress you down in front of everyone in a morning design review and then pat you on the back in the afternoon at the coffee machine. It wasn’t personal. Was he psycho or a master of compartmentalization? Never knew; never picked up either skill.

I don’t need to meet any more celebrities or tech bros—certainly not Elon, Jeff or Mark—but there is one guy I wouldn’t mind shooting the shit with, and that’s Sam Altman, CEO of OpenAI, the company that put AI into public discourse with ChatGPT and that has been the center of controversy ever since.

I watched Sam work this podcast the other day⁵ and I got the same vibes from working with BillG and other exceptionally smart, blunt, tech leaders.

Often the company that makes the market (in this case AI) doesn’t win it, but as long as SamA is leading OpenAI, they are going to be interesting to watch.

1. I’m using this term as a manager of managers or in MSFT parlance an M2, and I left because I was soooooo burnt out.

2. Even at internal events, fanboys would get there an hour early to score the front row seats hoping for a sweaty high-five from Steve.

3. That’d be Sean Marks from New Zealand, aka The Kiwi. Sean went on to play in the NBA and is currently GM of the Brooklyn Nets

4. For context, early in my career when I worked in the Field versus Product I typically was 10 or so levels away from the CEO. Microsoft is a big company.

5. If your curious, but don’t want to bother with the whole thing, this bit, where SamA mocks Mark Zuckerberg’s intelligence, is worth it.