The Epic Dinner

I stayed at my first job out of college for nine years. About seven years in, I moved to a different position; I became a developer in a startup-like new project within the company (I referred to the project here as Project Bob). Things were…different…there.

The leader of the project had held the title of chief technical officer, though he stepped down from that role in order to lead the project. He was “merely” an executive vice president. Despite this voluntary demotion, the man was loaded. He wasn’t one to flaunt his wealth around the office, but he also didn’t hide it either. He was one of the first people I knew to buy a Tesla Model S when it came out. Of course, he got the P85 model, which was at the time the nicest and most expensive. His name is Brian.

One evening when I was in the California office, my team lead, Britt, asked if I wanted to go out for sushi dinner with him and Brian. I love sushi, so of course I said yes. He also recruited Jeff, a senior technical director. (I realize I have a lot of stories with Britt that involve eating, even eating sushi. What can I say; it’s a shared interest.)

We were to meet Brian at a wine shop he likes. We would hang out with him and do a wine tasting, then adjourn to the sushi restaurant. I was honestly feeling a little nervous; I’m not necessarily cowed by impressive titles, but these were all incredibly smart and well-connected people. I would not only be the lowest-ranking employee there, I might also be the least intelligent. I also don’t drink alcohol, and I was worried that this would offend Brian somehow.

Arriving at the wine store, Brian was already several glasses in. My nervousness, at least on the second part, was mostly set at ease: Brian assured me that I didn’t have to do anything I wasn’t comfortable with. He was true to his word, telling me that I’m free to drink anything I want but then never even suggesting I take a drink of anything but water the rest of the night. Much respect for that.

Brian found a couple of wines he liked, so he went to go buy some bottles. I later learned from Britt, who was snooping, that he bought about two thousand dollars of wine that evening. He purchased three bottles, so this wine is likely nicer than anything I’ve ever tasted. I stuck with water though.

After the transaction was complete, we did a sobriety check. Jeff and Brian had both been drinking heavily, and deemed themselves unfit to drive. Britt had only sipped a few wines, so he got behind the wheel of Jeff’s rental car.

Brian handed me the key to his Tesla (this was before your smartphone acted as your key) and told me I was driving him home.

So I’m going to be alone with my boss’s boss’s boss’s boss, behind the wheel of his $120,000 car, driving him to his home. The evening is already shaping up to be more than I bargained for.

If you’ve never driven an electric car set to full regenerative braking, it will throw many of your driving reflexes out the window. Brian patiently explained to me what I would experience driving his car, and then seemed extremely relaxed as he navigated me to his home. We chatted the whole way; he’s an excellent conversationalist. As we neared his house, he pointed off to the side (I was keeping my eyes on the road) and said “down there is where Mark Zuckerberg lives.” Well alrighty then.

Arriving at his house, he went inside to freshen up a bit, and then we all piled into Jeff’s rental car (Britt driving this time) and headed out to one of the small cities in the South Bay — I want to say San Mateo, but let’s be honest, I never really learned my way around out there — to go to this sushi restaurant Brian knew.

I’ve eaten sushi for years. I’ve eaten good sushi, I’ve eaten too much sushi, I’ve even eaten some fairly expensive sushi. I think I paid $70 for a plate once at South Miami Beach (and it was worth it!). But I’ve never been to a place like this. This was one of those places where they make you a piece of sushi, you eat it, they ask you how you liked it, then they make you another one based on your response. I’m sure they had plenty of normal toppings, but we were having stuff like flying fish roe and tuna belly and who knows what else.

Britt told me later that Brian asked him privately, “Do you think Nathan is comfortable with all this? I don’t want him to feel like he has to eat something he doesn’t want to so he doesn’t offend me.” Britt assured him that I will eat any sushi put in front of me, but it does warm my heart somewhat to know that Brian was well aware of what his money and power can do to people and wanted to make sure I was at ease. I then went on to prove I was at ease by eating more sushi than anyone else there, asking the chef to keep making me crazier and crazier rolls and cuts of sashimi. It was amazing.

Brian covered the bill at the end, which was kind of him because the four of us ate about seven hundred dollars’ worth of sushi. If I had known it was that expensive, I’d have stopped several rolls ago. But then Brian escorted us next door to the sake bar which was attached to the restaurant. He proceeded to order approximately five hundred dollars’ worth of sake.

We stayed a bit longer, chatting and (for the three of them) drinking. Then we decided it was time for us to go. Brian told us to go ahead; he’d catch an Uber back to his house. I drove Jeff’s car back to the hotel that Britt and I were staying in. Jeff slept in the passenger seat. When we arrived at the hotel I offered to drive Jeff home, but he insisted he’d sobered up enough on the ride back that he was good to drive. I’m not the best judge of sobriety, but he seemed fully lucid and after the wine tasting hadn’t been partaking too heavily, so I gave him his keys and told him to be safe. I saw him at work the next day, so fortunately he had been.

Returning to my hotel room, I tried to process all that had happened. The excellent sushi, driving Brian’s Tesla to his house, and the fact that on this random Tuesday night Brian had spent more on food and drink than I would spend all month. More than many people make in a month.

I decided that the lifestyle of the rich and famous was not for me. If possible, my respect for Brian grew even greater that night; not only was he brilliant and talented and rich, he was also generous, and cared about people like me and wanted me to be at ease while hanging out with him. But while Brian seemed invigorated and energized by the evening, I felt drained.

I looked Brian up just now; apparently he’s a CTO again, at another company out in Sunnyvale. I wish him all the best. And I’ll forever be grateful to him for that crazy night and the great story it gave me.

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