Several years went by. I found myself standing in the hallway of the Computer History Museum in Mountain View, California. Entrepreneurs were darting about, occasionally stopping to chat as they moved in and out of the auditorium. I was at Y Combinator's practice demo day and had just finished delivering my two-minute pitch to an audience of YC alumni. My mentor, Matt, happened to be in Canada that week. He'd flown to Silicon Valley to say hello and watch me pitch.
It was funny how I ended up in Silicon Valley, actually. Nine months earlier, I'd been crying on my bedroom floor over all the issues I was having with 99dresses. I'd started the business with so much momentum and growth, but I suddenly found myself drowning in problems. I felt exhausted and alone and didn't want to get out of bed. I was running the startup as a solo founder while also attending university part-time to maintain my scholarship, which paid for my living expenses. I'd barely attended class that semester.
Oh, and I'd also just 'broken up' (if you could even call it that) with a guy I'd been seeing for the past year after suddenly discovering that he'd found himself a newer, shinier model to replace me. It was fun being disposed of like that, right as the sunshine faded and the storm hit. I'd felt abandoned by a lot of friends in my life, so it didn't really come as a surprise. I knew he treated me poorly, but I refused to acknowledge the full extent of his shit personality until that moment.
A contact from Microsoft emailed me a week after my rock-bottom stint, saying they'd nominated 99dresses for an innovation award. I'd need to fly interstate from Sydney to Melbourne for the finals. The last thing I wanted to do was receive an award while a fire raged in my business. It just seemed so wrong. But, as luck would have it, Zac wanted to fly down to Melbourne, and I needed to get out of my rut. He and I embarked on a two-day adventure.
I was seated next to the managing director of Microsoft Australia at the awards ceremony. We talked for hours. She raved about 99dresses and how it was such a great concept. I tried my best to sound excited as I clutched my trophy (I'd won my category), but inside my stomach was churning. My rational mind didn't want to be there, but for some reason, I'd ended up in that room.
Slowly, as the night went on, and the wine slid down my throat, I began to feel more enthused about my situation. After giving my table-companion a detailed first-principles analysis of why the Australian postal system was the root cause of all my problems, she suggested I move 99dresses to the US.
Suddenly my mind was on fire. The US. Fuck yeah! That seemed like a fun idea. I'll just go to the US, I thought. Their postal system had APIs, and their population density made the cost of shipping individual items more suited to my business model.
The next night, while still in Melbourne, I caught the end of a conference that my friend was running. The headline speaker was Matt — a tall, somewhat-intimidating man in his late thirties. Matt was the founder of a successful global online marketplace with many millions of users. I needed the help of someone like him.
Matt was mobbed by the audience as soon as he left the stage. When the crowd cleared, I strode up to him, introduced myself, chatted for a bit, and asked if I could buy him a drink sometime to get his feedback on some challenges I was having with my marketplace. He brushed me off.
A few days later, I was walking around my local area in Sydney when I ran into Matt. I'd lived there for years, and so had he — yet we'd never run into each other before. Trust me — I would have noticed. I'd watched Matt speak several times. He had a powerful presence that was difficult to ignore or forget.
A day later, I ran into Matt in the supermarket as we both approached the same shelf. Very strange.
Two days later, I was sitting at the bus stop as Matt strolled by.
"Seriously?! Are you stalking me?" he laughed.
"I swear to God, this is pure coincidence," I said, hand on heart. "I'm just innocently waiting for my bus. But since we keep running into each other, we may as well go for a drink sometime. Or lunch. Or dinner. Or coffee. Or whatever is convenient for you."
"You're going to get crushed in the US," Matt said two nights later, between bites of pizza. "You have no money, no local knowledge, no connections over there. Actually, you should apply for Y Combinator. At least that would give you an on-ramp."
"What's Y Combinator?" I asked.
"It's the most prestigious startup accelerator in the world. It's run by a husband and wife team — Paul Graham and Jessica Livingston. There are two batches every year. Thousands of startups apply for each batch, and YC invests in a tiny fraction of them. During the program, you spend three months in Silicon Valley, working with the YC partners. They bring in founders from the big billion-dollar tech companies to talk to the batch. The whole thing culminates in demo day, where you pitch in front of hundreds of investors. I think YC is your best bet for getting to the US."
"Okay. I'm going to get into YC," I said.
Matt and I became good friends after that first dinner. He was my Yoda — so generous with his time, and full of great advice. He was also brutally honest. My sister and I invited Matt and his girlfriend over for dinner one time (we were all friends by this point), and Matt had no problem calling my cooking "the most incredible pile of shit I've ever tasted" (he wasn't wrong). I liked that he didn't spare my feelings. When he said something nice, I knew he meant it.
In fact, I always felt like he saw some kind of potential in me that I couldn't quite see in myself. When I decided to shut down 99dresses several years after our first dinner, I emailed Matt from my New York apartment telling him so. He emailed back five minutes later, sending his condolences. Another email arrived two minutes later, offering me a job.
