A Dog in Silicon Valley

A Dog in Silicon Valley

I came to San Francisco with three pitches in my pocket. I called the first one Blimey, an audio app for your iPhone. Open it over dinner and wham! – you and your date now sound a little Irish. You might not think a couple of blarneys! or arseways! will loosen up the vibes, but don’t take my word for it: Mike M., one of our alpha testers, says that “Blimey’s the difference between tongue-wrestling your Bumble match, or crying into a box of Wendy’s spicy chicken nuggets.”

Blimey might save your night, but my second idea could change the world. The third was so revolutionary that Dan thought the VCs might seed it with a million bucks at ten, post-money.

So now I waited, sucking a cold brew in the corner of Mazarine’s Coffee, watching the door for Dan. He’d stroll right in – wearing that goofy grin and the ten thousand dollar suit he bought the second time he got crypto rich – and help me pregame for the morning’s big meeting. Our target was Lightbreaker Ventures, a fund so hot it left scorch marks on your cap table. Professional unicorn chasers invested in the modern paradox: harnessing entrepreneurial creativity without destroying the world in the process.

If Lightbreaker came in as a lead, then I’d be all set. My future shimmered like a slice of perfect strawberry shortcake.

The door opened and a sharp breeze blew in a pile of people. San Francisco was not like Montreal, where the January wind tore at your throat like a pitbull. I pulled my jacket tight around my chest. My right ear suddenly sealed, like the wind had stuffed it up with cotton. Before I knew it, my phone blurred, and the troop of people tilted sideways.

Nausea overwhelmed me. My right hand slapped the table. I struggled not to slide off and smack the ground. I started breathing, one-two-three, deep breaths. My right ear was completely clogged and no matter what I did to fix it – shake, whack, wiggle – the wall of silence stayed. The only sound I could hear was a faint ringing, like a tin gong struck by a miniature monk.

The world shook violently and I thought for a moment I must be dying. A sudden aneurysm, one of those random deaths that everyone reads about on Twitter. You feel shocked in a distant way, imagining yourself crushed by the very same elevator that ended young Mario Balducci and his dream of a billion-dollar valuation. But then you click through some great ad and next thing you know, you’re buying a Roomba.

Then the wave subsided and the world righted itself. I tapped my foot on the tile to confirm. Solid! A feeling of gratitude like I experience after the hottest yoga classes washed over me and almost made me weep. The sounds of the cafe whooshed back with the vigor of a thousand software engineers. I had three pitches in my pocket! Surely I could sell one!

But which?

Deep in thought, a moment passed before I noticed that Dan had texted. Apparently he’d shown up, looked for me, and left. Had he missed me when I was flattened on the ground? Did the depth of my meditations leave me blind to his arrival? Either way, opportunity had taken its cappuccino to go. Like a waiter scraping crumbs from the table, I packed up my phone, novel, and keys and headed down the street to see Takashi Maeda in the Mission.


I strode into WeWork’s elevator and hit the button for the 33rd floor. A short blonde girl fidgeted beside me in an expensive looking set of heels. “Cool shoes,” I offered, that age old trick of trying to lift my own spirits by raising someone else’s.

She sized me up for a moment, as if she was an appraiser inspecting a fake watch. “So, like, what are you building?”

I froze, suddenly a nervous wreck. Was she an investor, and those heels were Manolo Blahniks she’d bought to celebrate her latest IPO? If so, I couldn’t let the opportunity slip away. “Are you a VC?” I stammered, my armpits starting to leak.

“Oh no,” she laughed. “I’m a founder. I just assumed you were too. You know, all that anxiety.”

I felt a rush of relief, immediately squashed by the telltale scent of danger. An entrepreneur who wanted to know what I was building? What if she stole my idea? The next thing you know she’d be celebrating her seed round on the front page of TechCrunch!

What a pickle, and the speed of the elevator wasn’t helping. It moved past floors like a fat man scaling a skyscraper. I needed to say something, but which pitch could I ditch?

“It’s called Homey,” I began, consigning pitch number two to an early grave. “It’s Tinder for the homeless. Basically, homeless people need love too, and we’re solving that by giving them a meaningful way to seek out more fulfilling relationships–”

“That’s cool,” she interrupted. “So it’s like a crypto play.”

“Well, no. The thesis is backed up by research from Dr. Zanya Oren, a University of Texas sociology Ph.D.” This idea wasn’t blockchain, and the fact that she thought it was drove my defense of its potential. But to my chagrin, she’d already grown disinterested. Her face was in her phone.

Soon enough, the button marked thirty-three lit up, the doors slid open, and she limped away at lightning speed. I made my way to the front desk, where I scanned my ID and waited until a short man with the nose of a cocker spaniel appeared. “Good morning. Mr. Maeda will see you now. Follow me.”

He sniffed his way to a glass-walled room with a long oak table. Takashi Maeda, a thin man with a head full of silver hair, greeted me warmly. Cocker Spaniel shut the door behind us and we found ourselves in a soundless vacuum.

Takashi gestured to an open seat. The wheels of our chairs squeaked awkwardly as we took our places in a timeless dance, investor and entrepreneur. Cocker Spaniel sat beside Takashi, carefully opened a notebook, then readied a silver pen embossed with the Lightbreaker Ventures logo. They both looked at me attentively, and Takashi gave an encouraging nod. “So, what are you building?”

I inhaled sharply, studying the creases in his forehead, the well-drawn lines at the corners of his eyes. A stray thought floated in like a paper airplane on a kamikaze run, and I gave a silent prayer to Steve Jobs that my morning’s vertigo would not return.

“I call her Kamiko, and she’s the only co-founder you’ll ever need. She’s a robot assistant that collects your startup ideas and analyzes them based on probability of success. Then, she executes on all the most promising opportunities, simultaneously, thanks to a 5G Internet-powered neural network.” As I spoke, I showed them my crude airplane sketches – a little bit R2-D2, a smidge of WALL-E, a pinch of Baymax – while assuring that as soon as we closed our round, our first hire would be an award-winning concept artist. “Kamiko is a Japanese name that means little goddess. She allows any entrepreneur to truly scale themselves for the first time in human history, by allowing them to create and manage not just one, but hundreds of startups, all at the same time.”

The whole hour I pitched they listened intently, sometimes leaning their heads right or left, as if their thoughts were rubber balls passing from hand to hand. Takashi never interrupted or asked questions, only pausing to take small sips of water. Cocker Spaniel leaned forward and screwed his eyes toward his notebook, hand clenched on the pen like he was writing our collective billion-dollar destiny.

When I finished speaking, Takashi asked, “How much are you raising?” I swallowed before answering, “One million dollars at ten million post.” The assistant stopped writing and gave Takashi a momentary look. Takashi leaned back, stroking his chin. We sat there in total silence. I honestly had no idea what was going to happen next. Anything would have made perfect sense: sign a check, kick me out, pull a pistol from beneath the seat and shoot me dead on the spot.

Takashi finally gave a sharp upward nod to his assistant. The assistant smiled at me and excused himself, leaving the two of us to take each other’s temperatures. Takashi cleared his throat. “Your vision is bold, audacious even. It fits perfectly with our core thesis. It’s the kind of startup the world needs.”

With every passing word I leaned closer, trying to keep a poker face. I hadn’t known how much I truly wanted to build Kamiko until someone I’d never met before told me it was important, and now I wanted it to happen more than anything I’d ever wanted in my life.

Takashi seemed to be thinking hard. “We make three investments per quarter in this sector.” He looked at me, really looked me over, then took a long swig of his water. “Excuse me,” he said. He stood up, strolled to the window, clasped his hands behind him, and stretched his back until the joints popped.

Cocker Spaniel returned, carrying a large brown envelope. He took Takashi’s seat and placed the envelope down in front of us. With great care, he opened it and withdrew a single sheet of paper. On the paper was a handwritten address. “We’d like you to run an errand. There’s a standard poodle of some renown down in Portola Valley and this is the last place it was seen. Find it and return it to us. All expenses will be reimbursable.”

“Excuse me?” I replied. This was not at all what I expected. “Am I hearing you correctly? You want me to look for a dog?”

“All expenses will be reimbursable,” the assistant repeated. I glanced at Takashi, but he was still gazing out the window. “We know this is an unusual request, but today Mr. Maeda will discuss the possibility of investing in your startup with the other partners. While he does, it is imperative you locate this dog. We will have a decision for you by the time you return.”

I took the paper from him and stared at the address. 8100 Los Tranquilos Road. This was definitely the strangest investor meeting I’d ever attended. I considered the dynamics of the situation. If I refused the errand, I might not get the investment. And I had to admit, I was intrigued. A fetch quest for a dog I’d never met was my kind of crazy test. “What’s the dog’s name?” I asked.

Takashi’s assistant flinched as if he had been struck. “It’s on the back of the paper.”

I turned the paper over and looked into the bright, inquisitive eyes of a large brown poodle. Beneath the photo was its name: Paul Graham.


It was a breezy ride down the 101 and I shut my eyes for most of it. Ever since I did time in Los Angeles, where every Uber driver tries to sell you their TV show, I’d kept a policy of never talking in car rides. Don Paolo ‒ whose mustache could launch another chia pet craze ‒ gave a San Francisco twist by pitching startup ideas instead of screenplays. By the time we wound up the cliffside into Portola Valley, I’d become an expert on the market for mind-controlled prosthetic limbs.

I got out in front of a red mailbox with 8100 on the side in bold gold strokes. The sun gleamed off the numerals as if they were jewels set into stained glass.

The only people I saw were a few guys crowding a water sprinkler at the far end of the block. Ask for directions? There was something off about the scene. For one, they were frolicking like kids at a waterpark. For another, they weren’t wearing any clothes. Lastly, they each had long, shaggy hair and beards, like the teachers I’d met at the silent meditation retreat that turned out to be an initiation to the Rainbow of Honored Citizens cult.

The sound of people drew me down a winding driveway in the other direction. I considered the dog’s name: Paul Graham, the same as the founder of Y Combinator, a great writer and influential thinker on startups. Takashi needed the dog, and even though we barely knew each other, he trusted me to track it down. Surely he’d fund my company if I proved myself by retrieving a dog of such importance! My spirits rose. The check might as well already be in the bank. Dogs loved me! And I loved dogs! Takashi and my startup were a match made in heaven.

The driveway opened up to a grand lawn, backed by a picturesque hillside setting. Mountains, trees, flowers, you name it. Even bunny rabbits were hopping to and fro. I couldn’t help but smile at this natural bounty, but what really made me break out beaming was the giant house at the back of the lawn.

To call its three sprawling stories a mansion would have done injustice to its beautiful design. Powerful sheets of stone formed themselves into rectangular majesty, while walls of gleaming glass reflected the light of god. Wicker chairs gleamed whitely in verdure-hidden walks, disappearing beneath trails of water that streamed from the mouths of obsidian fountains. Whoever owned this house was rich and powerful enough to leave the boasting to the architecture.

I felt something at my elbow, and I turned to find a Chihuahua offering me a beer.

Now chihuahuas are generally small dogs, maybe six inches to a foot high, standing somewhere above your ankle and below your knee. But this Chihuahua was nearly five feet tall, with a thin mustache and posture like a hockey stick. “Hey bud, IPA?” he asked.

I resisted the urge to say “good boy” and scratch behind his ears, and took the can of craft beer from his outstretched paw. I was so stunned by the sudden appearance of a five foot tall, talking Chihuahua that it took a moment for me to realize we were in the middle of a party in full swing. Music, dancing, steaks sizzling on the barbecue, tables loaded with round, juicy watermelons, the works.

Everyone at the party was also a dog.

Tanned golden retrievers and skinny greyhounds milled about on balconies, nursing drinks and gazing at each other with bright-eyed intensity. A few bulldogs at the barbecue were speaking intensely in gruff voices about non-fungible tokens. A French poodle with purple hair held court around a picnic table, surrounded by an attentive herd of tail-wagging border collies. All of the dogs ‒ dozens and dozens of them, standing on two legs and behaving like humans ‒ weren’t wearing any clothing.

I pulled Paul Graham’s picture from my pocket and stared at it in shock. If all the people at this party were pups, how the hell would I find the one I’d been sent to fetch?

“How’s fundraising going, bud?”

The Chihuahua reminded me of my best friend Buster, my first dog. Those were the good old days, when I lived with a political science major named Brenda in New York City, and worked from home as a part-time marijuana chef. The memories of our stoned walks to the corner bakery were mingled with the sadness of Buster’s tragic passing and I looked at the Chihuahua with great sorrow, his black, glassy eyes reflecting the ephemerality of life.

“Fundraising’s going great,” I lied. I showed the Chihuahua my photo. “You haven’t seen this standard poodle, have you?”

“There’s a lot of poodles here, bud,” he replied, ogling the French poodle at the picnic table. Then he slickly passed me a business card with the logo of a law firm called Renovatrium. “Email me if you need any help with your paperwork. We do deferred financing on seed rounds, so it won’t cost you anything until you raise your Series A.”

“Free legal work? Wow.” Back in Montreal, the US dollar took you pretty far, but the idea of a lawyer who didn’t charge you was as hard to believe as a technology executive’s Congressional testimony on the importance of Internet privacy.

“Whoa, whoa, whoa, I said deferred financing. We’re betting on you, bud! Make it to a big, juicy Series A, that’s when we really sink our teeth in, you know what I mean?” He gave a series of excited barks. I was about to ask if he thought a ten million dollar valuation was too low for Kamiko, but at that very same moment a bunny hopped by, and he tore off after it.

I turned my attention to the purple-haired poodle and her audience of captivated collies. “Fundraising is a lot like poker,” I heard her say. “Investors could be your backers, your opponents, and the cards on the board all at the same time. There’s so much unknown information on both sides. It’s like you’ve only got a flush draw but need them to think you might already have a full house.”

Her thick British accent made her metaphor mesmerizing. I felt a kinship with the collies; we were all spellbound by her sparkle. She told us stories of her users and we saw our own reflected back. She mythologized her struggles and we glimpsed pathways around our greatest obstacles. She described her market opportunity with such passion that it almost made me forget Kamiko completely, in order to apply for a job.

But at the end of the day, I wasn’t a fifth employee kind of guy. So when she stopped speaking to refill the wine she’d been chugging, I made my bold approach.

“That was a really great speech,” I offered.

She looked at me curiously and said, “Are you a programmer?”

“No, I’m a founder,” I replied. “I’m building—”

“Damn. My technical co-founder just left for Sweden because of visa issues. I think he’s left the company!” She started softly crying, tears staining the fur around her eyes.

“That’s terrible, I said, awkwardly plucking at my right ear. Co-founder splits were truly the worst. If Lightbreaker funded me, then one day Kamiko would save founders like this poodle from the pain of breaking up. A hyper-intelligent robot could never be deported by US immigration… could it? Her agony endowed me with renewed conviction: I had to find Paul Graham, and I had to find him now. “Look,” I said, showing her my picture. “Have you seen this standard poodle anywhere?”

“What, you think just because I’m a poodle I know every fucking poodle at the party?”

“Please,” I begged.

“Paul won’t be any help. His advice is very pithy.”

“I’m not looking for his advice. I’m just looking for, well, him.”

She looked at me and gave a short sigh. “Fine. Paul’s over by the tennis courts. Go knock yourself out.” And she returned her attention to the border collies, who were hard at work digging holes to bury watermelon rinds.

I made my way to the northern end of the lawn. Against the green and brown countryside, pairs of doubles players smacked tennis balls across a red clay court. But there were no poodles in sight, only four golden retrievers wearing headbands and white tennis shoes. Perhaps Paul had gone to chase a frisbee, or lap at the water fountain. An older gentleman with a curve of white hair sat on a bench, watching the retrievers with a relaxed smile. He wore a black polo shirt over tan pants and brown shoes. Lines traveled his forehead and creased the corners of his eyes, like the well-worn paths of a life spent in thoughtful contemplation. I almost paid him no mind – I was still on high alert for Paul Graham the poodle – so it took me a moment to realize he was human.

And he wasn’t just any human. This man was Paul Graham.

I held Lightbreaker’s photo in my shaking hand, gazing at it in disbelief while I tried to recall the conversation with Takashi’s assistant. I was absolutely certain they’d sent me here to find a dog named Paul Graham, not Paul Graham himself. Wasn’t I? But here the man was, sitting there in plain sight.

“Excuse me,” I asked him.


“This is going to sound a little crazy,” I said, coming closer. “But have you seen this standard poodle anywhere?” I showed him my picture and watched him scrutinize it thoughtfully.

“No sir, I haven’t seen that dog.”

My face fell, and maybe he could tell I was crestfallen because then he asked, “Would you like to go for a walk?”

I hesitated. The sun had begun to set and if I didn’t get serious about completing my mission, I’d return to the city empty-handed. Takashi would be disappointed, and Kamiko would be rejected. Then again, Paul Graham started Y Combinator while walking home from dinner with his partner Jessica. Urban legend said that he often gave advice to startups by going for a walk with them. Could I really turn down this chance?

“What would you do,” I asked Paul, as he rose from the bench and we began to walk beside each other, “if an investor sent you on an impossible errand, the completion of which would determine whether or not his fund invested in your startup?”

“Nothing is impossible for the determined founder,” he replied. “That’s what makes founders different from everyone else.”

“But what if the investor told you to look for something that doesn’t actually exist?”

“Investors are like seashells,” Paul said. “If you need money, don’t look in a forest. Go to the beach.”

I could see what the poodle had meant by Paul not being any help. I looked for an escape. A small but growing group of dogs had withdrawn from the party to follow us at a respectful distance.

“What are you building? Maybe I can help.”

I told him about Kamiko. After I’d finished my pitch, he gave a loud snort. “Preposterous,” I heard Paul Graham say. “The technology required to build a company like that is at least ten years out. Minimum. It’s impossible.”

“Nothing is impossible for the determined founder,” I said, repeating his words, but then he said, “I hate your idea.”

My blood began to boil; I’d never thought him capable of such a dirty surprise attack! Here I was, spilling my guts on my dream, and there he was, sentencing me for a capital crime. We sparred over Kamiko until I exploded. “What do you know about anything? You had a co-founder. You don’t need funding. This is a waste of my time! I didn’t come here to find you, I came here to find a dog, so I can get back to fundraising!”

I started to feel sick. The scenery around us softened, the shrubbery and grass melting into a Dali painting. My head spun; I saw the Chihuahua making tiny circles in his mustache with the tip of his right paw. He looked like he was stirring a milkshake, ensuring the straw wouldn’t clog before taking a sip. I felt the return of a distant ringing in my right ear. I spotted nausea too, from the corner of my eye, preparing its leaden blanket–

Maybe I was dying. Was that what startups were? Like dying stars. All of them, even our Sun, will one day collapse. But we constantly dream them up anyway, because the light feeds our chances to bend the world’s path.

Was Kamiko really the right product? What about Blimey? Homey? All the other unborn stars I’d yet to name?

I knew then, the cause of the strange spells of vertigo that had plagued me all trip.


The last thing I heard before I fainted was Paul Graham saying, “Alright, fuck it. I’m in for fifty k.”


“That’s an incredible story!” said Dan, and I could almost hear his goofy grin across the phone line. “Did you take the money?”

Unlike San Francisco, Montreal was a frozen block of ice. Snow powdered the park in white blankets and I shivered in my parka, gloves, and hat.

“That’s the crazy thing. When I woke up, everyone was gone. The dogs, Paul Graham, all the food and drink. There were only a bunch of maids in uniform, bagging garbage and sweeping trash. And when I got back to the city, Lightbreaker didn’t answer any of my calls or emails. Not even to reimburse me for the Uber!”

“Ghosted,” he said, and I could tell he understood what had happened. “Sucks, but that’s pretty standard. They don’t want to say yes, but they won’t say no in case you end up getting shitloads of traction and become the next Airbnb. So what do you do now?”

“Well,” I said, bending down to scoop up a piece of dog shit on the snow, “I decided to pivot my startup. Go back into the lab, maybe build something on my own and bootstrap it.”

“Epic,” said Dan. “Let’s stay close on this one.”

“Sure thing,” I replied, leaning over to rub Paul Graham behind his furry brown ears. “Good boy.”