Return Flight

6 min read by Dmitri ☕️.

Entire trip lasted around four days, half of which I spent in the air. Three different planes carried me from Chiang Mai to Bangkok, then Taipei, then San Francisco. Three more did it again in reverse order.

I crossed the Pacific twice for a ten-minute meeting.

All the photos in this essay were taken with my fourty-year-old Yashica Electro 35 camera on Ilford Pan 100 film.

A week prior, Ishtiaq called first thing in the morning with the news: Y Combinator invited us for an interview and all three co-founders had to be there.

Y Combinator is the most respected startup accelerator program on the planet. They helped Air BnB, Dropbox and Reddit (amongst hundreds of others) get to the position they are at today. Their unique way of deciding whether we were worth their investment is paying for everyone’s return flights and accommodations to meet us for exactly ten minutes.

Arjun flew from Dubai and I flew from Chiang Mai to meet Ish at our tiny San Francisco HQ.

My part of the job at the company is managing technical resources, building, and fixing things from my home in Thailand. Last time I flew to SFO I was there for nine months before making it back.

While in California, I was always busy. Surrounded by great people, though I often felt lonely, wishing I was back home with my girlfriend, Betty. This trip brought a lot of those memories back. Of course, the prospect of seeing Arjun and Ishtiaq, my very close friends and co-founders, as well as a shot at being a part of a Silicon Valley’s elite club was exhilarating. I felt as if I was being propelled to the heights of an emotional rollercoaster as I sat in the tail section of the plane, quaking from the turbulence.

An edgy stewardess sat facing me directly across the emergency exit route. She didn’t seem to stay still for one minute during the entire flight. Perhaps it was her first year at the job.

Border-crossing is everyone’s least favourite part of international travel. Even with a Canadian passport, arguably one of the best travel documents in the world, you could still get hassled.

A long line of tired passengers snaked through the hall. I sent my messages out, checked my emails and waited for my turn. Shifting one foot in front of the other, as the crowd methodically inched through the three open booths.

The invitation letter I presented to the officer seemed to have immediately put him in a good mood. He waved me in while sharing a joke with his co-worker. I drowsily stumbled across the hall, amused at the amount of grease a sheet of paper has added to the grinding process of being admitted to the USA.

Little Hollywood.

I took a short Uber ride with two other passengers before arriving at the house. Ish met me with a bear hug and we spent an hour catching up until Arjun, who flew in a little earlier, woke up and we got some dinner.

The house.

Ish and I, captured by Arjun.

The house, our HQ, seemed unchanged since the last time I was there.

It resided in San Franciso’s Little Hollywood — a fairly unknown neighbourhood that warranted a (relatively) affordable rent, a distant view of a park and close proximity to Caltrain station.

We made the garage our office with an array of sticky notes, company posters, a whiteboard and large table space that hosted laptops, spare monitors and a few home automation speakers. A few of my photographs (mostly mountains and trees) were hanging on the walls, but the piano was gone.


Next morning I got to meet Bhargav and Chandra in-person. They were both responsible for developing new features for our product throughout the past few months, though I’ve only spoken to them on the phone until now. It was all business as we were in the rush to prepare for the interview.

The interview.

It took us about an hour in an old van to get to Mountain View. Our Uber driver did not seem to be in the rush; he drove at or below the speed limit the entire time. Which made me feel uneasy as I tend to speed whenever I’m on the road, though we had more than enough time.

Y Combinator building is a refurbished mini-warehouse that’s been furnished with nicely-painted walls, chairs and sofas. A small plaque, no larger than a mailbox stood in front of it, identifying it as the place we wanted to be at.

Met a few other founders in the parking lot. A horoscope app, a social tool for events, and women’s health cycle tracker. We stood in an awkward circle, wondering if we’d ever see each other again.

There were seven or eight people in the interview room. Naturally, only a few of us spoke as the decisionmakers were trying to determine whether we were the right choice for them. We were asked just a handful of typical “investor” questions. Everything went by uncomfortably quick, leaving only a hazy recollection that felt like a hallucination.

We took a train back and waited at the house. The rejection email arrived a few hours before my scheduled departure.

Effectively nothing has changed for the trajectory of our business. There were over a thousand customers in our database that we had to satisfy and convert. A long list of products to be built, bugs to be fixed, and newly scheduled meetings to attend. Still, nobody likes to lose.

I flew home looking forward to seeing Betty and all the comforts of sleeping in my own bed.