I don’t know what came over me, but I had nerve to ask the ninety-four-years-old David Morgenthaler — one of the founding fathers of venture capitalism in America — if he entertained sleepovers with his slightly older friend Robert Wilson. The two had invited me to their private residence at a senior citizen community that was so extravagantly posh that apart from the $5 million entry fee just to get a three-bedroom apartment, visitors had the option of checking their cars in with the valet upon arrival.

In this up-scale senior home, Dave and Bob were bosom buddies by way of living in apartments next door to each other. The communal nature of it all — friends one knock away, sponsored activities like arts and crafts, and the flirtatious energy of a bunch seniors under one roof — reminded me of the college dorm life. I imagined the two seniors as born-again bachelors drinking brandy and smoking cigars, then drifting off together in the same bed, not even able to make it back to their own rooms before a drunken stupor conquered them.

Once that image got hold of me, I could not stop myself from cracking the joke: “So when it’s late and you’re all tired from drinking, do you guys ever have sleepovers with each other?”

I just about wanted to cut off my tongue, but, for some reason, Dave thought it was funny. “No, both of us thankfully can still make it back from across the hall before we pass out,” he chuckled. College dorm life indeed.

I originally met the two nonagenarians at one of those exclusive events for execs and VCs, where I was not only the youngest one (as always) but also the most awkward in trying to figure out which fork of the three was appropriate for eating shrimp salad. I had just come out of the bathroom when I saw a tired Bob sitting by himself with a big Band-aid plastered under his left eye. I had always gotten better along with older persons than kids my age, and so, thinking it a smarter move to occupy myself in the art of conversation rather than getting drunk on free wine, I plopped down on the seat next to Bob and started chatting. Dave eventually joined in the conversation after straggling in from the main dining room to look for his friend. We talked of Chinese railroad workers and Google cars, the endless line of fruit orchards that had once covered Silicon Valley. I tried my best to impress them, delivering a well-calculated joke every few minutes to make them laugh.

Not before long, the van that would take Dave and Bob back home was leaving. The two were enjoying the conversation too much, and that’s when Dave asked me to join them for lunch. Of course I said yes. They departed, but not before I shook their hands and Bob said that I was a “charming woman.” Charming woman? The thought amused me; I had never thought of myself in that light. I envisioned my alter ego as more along the lines of a middle-aged white guy with all the man-childness of Conan O’Brien and the satiric edginess of George Carlin. But I guess one should take those types of compliments when given.

Two weeks later, I was meeting the two legends, Dave and Bob, for lunch at their extravagant senior living home. To be quite honest, I actually have no clue about who Bob Wilson is or what he ever did. Type in “Bob Wilson” or “Robert Wilson” in Google search, and I’m sure you won’t be able to find anything either, even though apparently he’s supposed to be a big deal.

But Dave was a different story. Type “David Morgenthaler” in your Google search bar, and you’ll find a man of exceptional accomplishment: founder of the multi-billion dollar Morgenthaler Ventures; a key player responsible for lowering the capital gains rate during the Carter administration; philanthropist extraordinaire who spent the last few decades shelling out big cash to scholarships and foundations. With that quick Google search, that friendly, centennial redwood I had at met a dinner had become an untouchable mythos, a titan god, someone who made mere mortals like me unworthy. No, he was no longer Dave. He was the respectable Mr. David Morgenthaler.

So, upon the day of our lunch, the thought of meeting such an extraordinary individual threw me into a frantic fit. I researched Morgenthaler for hours, printed out notes and tried to memorize them. On the drive over, I talked to phantoms of Morgenthaler in the car, rehearsing how elegant I could be for the big lunch.

Soon after I arrived, however, whatever mythos I had created around the god-like David Morgenthaler was swiftly destroyed. As the two seniors came to greet me, their fragility as humans became beautifully exposed: shuffling feet, clouded corneas, a shaky hand that tried its best to be firm. The two gave me the tour. A gym for working out, a communal pool, the activity center for arts and crafts. As we passed a class going on for making family picture frames, the image of the David Morgenthaler gluing popsticks together for some kiddy art project got stuck in my head. So I asked him if he ever made any arts and crafts. He replied that he made a wreath once, but it didn’t turn out too well. The respectable Mr. David Morgenthaler became Dave once again.

We ate lunch at the in-house café. Dave made sure to sit between Bob and me because his hearing, he said, was not too good. The menu was catered to maintaining a sensible senior diet; nutrition — not taste — was of prime consideration. My two companions munched on sandwiches and fruit cups. I had a salad that I barely touched, leaving me hungry. That was the trickery of these types of occasions: they’re called deceptive labels like “lunch” or “dinner”, but conversation was actually the main course.

I told Dave and Bob that I was on a life-long journey chasing some elusive idea of happiness. I was a law student but working a low-level position in business. In fact, I did not see myself as an attorney. I had just turned down a high-paying job opportunity that would have sealed my fate as a practitioner of the law and sent me down the road to upper-middle class status. Dave and Bob found it hard to fathom the idea of someone so young turning down so much money. They could still recall their young-adult selves, fresh out of school, scraping by on minimum wage at just a few cents an hour. I was to them the paragon of the wasted generation.

But then I told them of the depressive moods I’d get in law school, my back hunched over books, shutting out friends and family for just a couple worthless points on a test. I recalled the time when I had not left the house for five straight days studying for finals, walking out only once on the fourth day onto the curb of the sidewalk so my friend could drop me off a carton of Korean barbecue.

“I knew my passions lay elsewhere,” I said.

Passion was a strange word to the two. Follow your passions — it was a funny phrase that neither of them had grown up with. That whole notion of dream-chasing had come a couple generations later for them in the form of Generation Y. Yes, Generation Y — that dissatisfied bunch of whining hypochondriacs who had grown up during the upswing of the American economy, sometime between the 1970s and 1990s. To them, I was just another disaffected youth, on the never-ending quest to find self-fulfillment.

I tried to find another way to relate to them. “Have you ever had a job you disliked?” I asked.

“Well, yes, of course. Haven’t we all?” Dave responded.

“Did you ever stay there?”

“No, of course not.”

“How come?”

“Wouldn’t have been happy there.”

“Yes, exactly, that’s it. That’s passion.”

Just like that, Dave understood. Bob understood. They were successful precisely because they had done what they loved doing. Call that passion or any other word, but at the end of the day, their immense success had reflected a refusal to settle for a second-rate life.

Often people are astounded when they hear that David Morgenthaler invited me to hang out at his home with his bosom buddy Bob. How did this young upstart Asian girl get a meeting like that? That’s a question I sometimes ask myself too. Then I start doubting myself, becoming paralyzed by whatever inadequacies I can conjure up in my head. That’s the moment when I let my inner Chinatown hoodlum slap me awake and say: don’t let those silly images you create about people get to you. You start treating someone different just because you find out his pedigree, and that ease with which you carried on your conversations just completely dissipates into awkwardness. That person’s been the same all along; you’re the one who changed.

Once I let go of the image of the respectable Mr. David Morgenthaler, the scene became just me and my two senior citizen buds — Dave and Bob.