Mercury Rising

An essay on facing your fears

I folded my legs in a tight lotus pose, straining to stay afloat in one of those couches that seeks to swallow you whole. The living room was warm. Plants, snipped, grafted, misted, propagated, and poised, lined the shelves overlooking a sunny San Francisco street.

Sonali sat on the floor hunched over her phone as Dead Sea by The Lumineers played in the background.

“Okay, what time?” She asked.

I pulled up my phone and zoomed in on my birth certificate. “2 AM.”

“And the minute?”

“You really need the minute?”

“Yes.”

“Okay, 2:08 AM.”

The phone-light shone on her aquiline features as she bent over in quiet concentration. Her eyes lit up. “Yes, I knew it. Look,” she pointed the screen towards me.

It was a lattice of lines and dots. I squinted in confusion. “Okay, nice piece of abstract art.”

“No, silly. This.” She clicked on one of the dots. A small pop-up emerged. Mercury Rising. “I knew you were a Mercury.”

“I thought Mercuries had to be quick-witted.” I asked, suppressing a smile.

“Haha.” She panned across the rest of the latticework.

“Okay, so how am I gonna die?”

“That’s not what it says.”

“Well, come on, it’s gotta tell me something useful. What about this? What’s my weakness, my foible, my tragic flaw.”

She scrolled into one of the little boxes and with a single click, was assaulted with a flurry of pop-ups. “Oh my… Yeah, your work…”

My brow furrowed. My work? I know that I haven’t gotten a Pulitzer prize yet, but things have gone relatively well for me.

“Yeah, as far as I can see, this is your big downside.”

“And?!”

She continued to scroll, speaking to herself, “Oh wow.”

“Girl, you can’t just Nick Barber me like this.” My mind flitted to a high school acquaintance that would always dangle gossip too long before spilling.

“You and your obtuse references… it says here you should never work with your friends.”

* * *

I had a habit of asking friends to work with me. In college, I roped Tosin into one of my schemes. The unforgettable rise and fall of Palatine Analytics and directly after graduation, Jamie and I had dabbled in founding together. We had shared essays about overthrowing Google at its own game: building a better search using NLP. Almost like it was always meant to be.

But I had pursued Ben most of all.

We used to hang out after hours in the underbelly of the Twitter campus. On the ground floor of a large building that opened up into a patio, a putt-putt green of sorts.

We’d scour the city, searching for sugary sweets to sip, finding the nearest bubble tea place and spiking our insulin levels to hit that Ballmer peak of saccharine creativity.

We’d film these dumb absurdist skits. Doctors seemingly bloodied from surgery, sucking on their crimson fingers moments before the audience was shown the buffalo chicken they feasted upon. Stupid shit like that.

* * *

“Okay, okay. Tech companies as new dads.”

Ben and I sat off cordoned at one end of the Thanksgiving dinner table. Other friends were having quiet, serious conversations. But Ben’s eyes sparkled at the comment, “Okay, yeah.”

“So Google is the dad. Standing there waiting for the baby to be delivered, pacing back and forth. And suddenly he says, ‘let’s deprecate the baby.’ What? Yeah, went straight from beta to deprecation.”

Another friend across the table gave me a strange look. “You can’t deprecate a baby.”

Ben leaned forward. “No, no, no, here’s how it would go. He’s standing there waiting for the baby to be delivered. Phone rings. Picks it up. Yeah? Promotion? Yeah, VP New Org? Absolutely. Walks out. Thanks, bye. Baby drops on the ground.”

We cackle, rolling our heads back. “Okay, okay, Airbnb. New dad’s so expectant, wringing his hands. Baby comes out, looks at him, he’s like, ‘Uh, it’s ugly. Can we, uh...’ Tries to shove it back in.”

Ben and I are now howling. “Okay, Tesla, Tesla! This is good. Man is kneeling there waiting for the baby. Big product launch, new vehicle. Everyone’s excited. Except for the guy, the CEO. There’s one hand waiting to catch the Tesla baby, another hand waiting to catch the SpaceX baby, a foot for Neuralink, and one foot for The Boring Company.”

I smiled. “I’m guessing this is Elon.”

“Well yeah, he’s got like 12 kids, doesn’t he?”

Ben and I were nearly out of our seats. The rest of the table eyed us suspiciously. As we tried to shove mouthfuls of stuffing in between bursts of laughter.

Later that night, we walked in the shrouded streets of San Francisco. The quiet, almost deserted feel.

“Why’d you end up joining that other startup Ben? I mean, it was kind of a stupid idea.”

“Well...” He brought his finger up to his mouth and looked at me. “My manager was really persistent.”

“Yeah.”

“Well, he just kept asking me, and... I guess eventually I was convinced.”

“And I guess your previous team kind of...”

“Yeah, it kinda sucked and...”

“Well, what about now?”

“Ha. Yeah, that’s true... It’s probably about time to move on too.” He looked wistfully.

“Ben. Do you wanna co-found together? I mean, I know it’s sudden. I know we’re good friends, but I’d love to build something with you.”

He looked away. Brought his hand up behind his head to scratch. “I don’t know. Right now’s maybe not the right time. But maybe for your next one. Okay?”

* * *

Maybe I remembered it wrong. Maybe not. Sometimes you only hear what you want to hear. You only remember what you want to remember.

But what I do remember is that I never understood why. I never understood why he said no. Was it something I said? Was my idea too zany? Was I not formidable enough?

The obvious reason I kept coming back to was me. Something was wrong with me.

But in the end, the reason didn’t matter. Ben did not join me, and I founded StartPlaying alone.

I never forgot that hurt.

After I left StartPlaying I wandered my post-exit landscape looking for something to do next. And I thought of Ben again. Time heals all wounds. And those bittersweet memories did eventually form fond ones.

We began to hang out, chatting, riffing, recording our inane and darkly savage humor. And my heart began again to swell.

What if this was the time? What if now, having successfully founded, exited, and raised from the best VCs on Earth, he would finally want me? I wonder how familiar these lines are in love, in work. But I’d need to ask him again.

During my time at Start Playing, I learned how to revisit past hurt.

There were four steps.

Step one was to rationalize it. What really hurt you? Rejection? Maybe. Or maybe there was a fear that I couldn’t do it on my own. A fear that I needed someone else.

Next is to practice, to test. You cannot overcome in a vacuum. You have to slowly make advances. If you’re afraid of the dark, you have to venture forth.

As a kid, I used to close my eyes and imagine the monsters dwelling in the shadows. Imagine them coming up and gobbling me whole. My heart quickened. My skin taut. Goosebumps speckled my flesh. But no monster emerged. I’d inhale and open my eyes and walk bravely into the dark.

The final step to overcoming a trauma is to repeat. To repeat the action.

To ask once again “Ben, would you want to co-found with me?”

“Maybe for your next one…”

My heart sank. I felt queasy. Once again, I felt like I wasn’t enough.

This may have slipped you by, but I said there were four steps to overcoming your fears.

Step zero is, of course, make sure that there really is nothing in the darkness.

I ended up founding my next company alone. Becoming one of the redeemed pariahs in the Valley: a solo founder. I was able to raise, hire a team, build a product. And I guess in a sense, I faced my fear. The question of could I do it alone was answered, the book closed.

And yes, it was probably what I should have done all along.

But why? Why then did my heart yearn for such kinship?

* * *

“What, no witty remark, no deeply skeptical sentiment?” Sonali looked back at me. And she stopped.

Sometimes you know when you’ve won an argument. She saw it in my eyes. My face probably shone with resignation and a wistful look.

“You know, Sonali, in my entire life, that’s one of the things I always wanted. To start something. To go on a journey with a friend. A companion forever. You know, is that too much to ask? But maybe... Maybe looking back, maybe that was the problem all along. It was the cart before the horse. Maybe that desire to do it with somebody, with a friend, a partner, was the thing that distorted my preferences. Got me into challenging relationships. My goal foiled itself before it even started…”

She smiled and shook her head. “You’re such a Mercury.” And began to read the rest of my chart.