Part 5 - The First Week

11 minute read

Pssssst…If you haven’t read all about how we made it this far, start here

My hands are shaking. I try to sip some water. 2 more pitches to go. And then us. I look across to the other wing of the backstage area. Romy and David wave and smile nervously. I try not to vomit.

“…if you’re interested in this space, come find us. Thanks.” The booming, amplified voice of one of the other YC founders echoes around the conference hall. Three thousand investors, founders, and members of the Silicon Valley royalty, clap politely. Within 6 seconds, the next pitch starts.

One more to go. And then us.

I try to go through the spiel for our Demo Day pitch one more time but my mind is completely blank. I shiver a little as the adrenaline thumps around my body. I can taste the panic rising in my throat. My tongue feels like sandpaper. I have a minor lisp but it becomes extremely prominent when my mouth dries up. I made the mistake of not having water with me on the day of the practice run and gave an uncanny impression of Daffy Duck. I’m terrified it’s going to happen again today. So I take another massive mouthful of water and swirl for as long as I can.

There’s a tap on my shoulder. It’s our YC Partner.

“You’re gonna do great. Just remember to speak slowly and look at the audience. Break a leg.”

I feel my chest swell with confidence for a brief second. And then I hear the applause.

No more pitches to go. It’s us.

The curtain parts and a hand ushers me forward and through. I walk out onto the stage. I’m hit with the glare of thousands of faces staring back at me.

I open my mouth.

Nothing comes out.

I looked over at David and fought back the urge to throttle him. He was quibbling with the guy behind the counter about what exactly the difference was between the Malt and the Milkshake. Could he not just order food like a normal human for once?

It was the 8th of June, 73 days until Demo Day, and about a week after the rush of our YC interview. We were in a burger restaurant in Cupertino; trying to kill time until our Airbnb was ready. We were exhausted (tuirseach traochta is what comes to mind) and starting to get on each other’s nerves.

The last 10 days had been emotionally and physically draining. After the initial excitement faded, the reality of it all sank in. Doing YC meant saying goodbye to our lives in Dublin. And I really liked my life in Dublin. As we boarded the flight home, I was conflicted. This was my Dream™️ but I was suddenly filled with doubt. Up until we got the final call from YC, it all felt like an impossibility. Now it was very real.

I hadn’t really prepared for how hard leaving my job was going to be. It was the first 9 - 5 job I’d ever had. I didn’t realize how close I’d become with my office pals. I took this snap of my desk on my last day. I feel very nostalgic, sitting here 10 months later, looking back on it.

My old desk

Before all this kicked off, I was honestly really content. I loved my team at work. I was finally thinking of moving out of my parents’ home and gaining some degree of independence. I’ve had bouts of anxiety and some rough times before so I really didn’t take this period of relative calm for granted. Was I throwing away a good thing for a pipe-dream?

And what exactly were we going to be doing for the summer anyway? Romy had met with one of the YC partners the day after we got in and pitched another couple of possible ideas. One of them was a side project I’d worked on nearly a year before - an app to help you keep up with close friends and family.

He liked that one the most - or maybe more accurately, he disliked it the least.

The more I thought about the idea, the more excited I was. I built the original MVP during a rough period when all of my close friends from school had just emigrated. I realized then that I hadn’t kept in touch with my college pals in the 2 years since I graduated. For a number of weekends in a row, I had literally no one to talk to.

The core premise was “What if you could make something that helped you remember to keep up with friends and family?”

If you’re reading this and thinking “Classic, a naive software engineer thinks his poor social skills can be fixed with a few lines of code”, you’d be depressingly close to the mark.

It was obviously a very fuzzy idea (there was a reason I never finished the MVP). It was made even fuzzier by the fact that our YC Partner had sort of re-imagined it differently. We were working off that re-imagined version, which looked a little like a personal assistant, but for relationships. Something that would run errands for you to help you connect with your close friends and family. If all of this is sounding very vague then I’m accurately conveying exactly how mixed up we were about it.

I tried to make sense of all of these swirling thoughts as I grumpily demolished my burger. Pretty soon we would be able to check in to our Airbnb, get a good nights sleep, and work it all out.

I hoped.

Within an hour of getting accepted to YC, we started looking for accommodation. YC strongly recommends that you stay within a 15 minute Uber of Mountain View. The only problem is that Mountain View is a leafy suburb without a whole lot of housing stock to spare. And there’s a housing crisis in the Bay area. And whatever sparse housing that was available was snapped up by all the other teams who had been accepted some weeks (or months) before us.

Long story short, we were scraping the bottom of the barrel. Add the fact that we had no credit rating to the mix (who’s this fella Fico we keep hearing about?), and our only real option was Airbnb. An initial search revealed one house for $14.5 a month (yikes), one for $19k (holy shit), and one for comparatively good value at \$7.5k.

NB: People tell you that the Bay area is expensive but you need to see it to believe it.

The \$7.5k per month house had mixed reviews. They spoke of a somewhat erratic owner (let’s call her Alice) who would arrive unannounced and “check-in to make sure everything was ok”. There were also a few complaints about the general cleanliness, but to be honest we chalked these down to overly picky guests. All things considered, we didn’t have much of a choice. There was a pretty massive sweetener too - the place had a pool 😂. Life imitates art, and my life was certainly following closely to the plot of Silicon Valley S1. We just needed a Tiki Hut to complete the picture.

The Airbnb listing

2 days before we left Dublin, I got a message from Alice. The english was hard to comprehend but the general gist of the message was that the house was for sale. If we wanted to stay, we would have to leave for a couple of hours on Saturdays and Sundays for showings. If we weren’t ok with that, she politely requested that we cancel the booking. Christ. We had no option but to accept.

If I had known then what I was really signing up for 🤦‍♂️

We finally got access to the Airbnb about 4 hours after the agreed time. It was not as advertised. I really can’t articulate how much of an understatement that is. It reminded me of the episode of Catfish where the guy thinks he’s talking to Katy Perry but it turns out it’s his second cousin Frank.

The house was for sale. This was very much true. What Alice failed to mention was that it was set up as a show house, and filled with fake furniture. Faux-metal fake cutlery (not to be used). A fake office chair (the seat wobbled and crunched when you tried to sit down) in front of a fake desk (the drawers weren’t screwed in), topped off with a mock laptop made of plastic. 2 of the 3 bedrooms had tiny kids beds in them.

And the couches. The feckin’ couches…

They were rented from a showroom. We were left strict instructions not to even think about sitting on them. The only solution was to cover them with bedsheets and hope for the best.

David napping on a covered couch

The external photos also craftily showed the whole house, but 2 side rooms were being rented out as separate Airbnbs. One of them had a door into our area that could only be locked from the other side. Creepy AF.

What did in fact exist was the swimming pool out the back, which more than made up for everything else being out of whack. We quickly claimed a room each, threw on our togs, and jumped in.

Chilling in the pool

Part of me was a little delighted that it was all a bit topsy turvy. It made for a much better story. That night, I was so tired that I could have slept on a rock. Which was lucky because the tiny mattress I was on may as well have been stuffed with gravel.

My first day of Secondary school is seared into my brain. Showing up early and standing by myself. Hoping that someone friendly would come talk to me. Trying to look cool and smart and a little aloof. Trying to hide the fact that I desperately wanted everyone else to think I was cool and smart and worth befriending.

This was that.

David, Romy, and I stood in the corner of the hall. We were early for our first batch dinner. It was only 10 days since the last time we were there, nervous and giddy at the prospect of pitching to the YC partners. Now we were nervous and giddy at the prospect of meeting new friends.

But most of all, we were terrified of being found out as the frauds that we were. Some of our so-called “peers” had 5 digits of monthly recurring revenue. We still had to decide what our name was going to be (we were flirting with the idea of rebranding our month-old company as LetKit - short for Let’s keep in touch).

The fact that we were a week late added to the sense of isolation. We’d missed the first few days of orientation and introductions. From our corner spot, we could see people greeting each other and catching up. It looked like small cliques had already formed.

“We’re gonna have to talk to someone eventually.”

“Oh, are we?”, Romy quipped back at me, her voice laced with sarcasm.

It felt like my social skills had withered a bit after college. I used to be good at this! But now I was tongue-tied and awkward. And also apprehensive. What if they asked us hard questions about our product? Or our acquisition strategy? Or one of a hundred other little things that we hadn’t figured out yet.

After some significant humming and hawing, I finally bit the bullet and walked over to a small group chatting beside a few couches. 2 of them would end up being our best friends in the batch.

“Hey, how you gettin’ on? I’m Patrick.”

I managed to get through that without my voice cracking or anything embarrassing happening. We were off to a great start.

They all introduced themselves and we exchanged some quick pleasantries. Within 30 seconds we were into the meat of any initial conversation in YC.

“What are you guys working on?”

One of the most striking things about Y Combinator is the way in which the social hierarchy is formed. Love it or hate it, your status is determined by how successful, cool, or interesting your startup is. No one really cares if you worked at Google. Or if you went to Harvard.

If your company is doing significant revenue, you’re conferred a sort of gravitas and seniority. If you’re curing cancer, or something equally as impressive (micro rockets anyone?), you’re one of the top dogs.

And if you don’t know what the hell you’re doing, you’re at the bottom of the food chain.

I pitched an abridged version of our nascent idea - a personal trainer for your personal relationships. We didn’t really have much else, other than the tagline and some examples of things we might do - essentially just help you remember birthdays and find good gifts. We were thinking big.

“Yeah, I could see that…”

Jenny (not her real name) was the CEO of her start-up. She’d studied Engineering, like almost everyone else at YC, but was the sales and business mastermind behind her company. She had a soft southern accent, a sharp sense of humour, and was brimming with the pure, unadulterated confidence that only Americans can have. She was also a Sorority girl, something we would tease her about relentlessly for the rest of the summer.

“…but what I would really love is something that would help me get tailored gifts for my customers, I’m trying to use this website but they are terrible, last week they…”

Jenny proceeded to give me about 50 different ideas for what we should do next to solve one of the different problems she was facing. This would become a running theme for the rest of the batch, and was another peculiar aspect of YC culture. A common way to bond with your fellow founders was to give them ideas for their startups. The better the idea, the more helpful you could be, the more popular you became. It became a sort of helpfulness competition.

There was an almost limitless stream of ideas, advice, and suggestions coming from all directions. This could great, but it also melted your head. A lot of the time, the different pieces of advice were directly contradictory.

“Maybe you should try doing x?”

“Whatever you do, don’t do x.”

“You should focus on y right now.”

“I’d ignore y for the moment, it’s not that important.”

The net effect was positive. Sometimes a random conversation would spark a major change or fuel a significant improvement. But the signal to noise ratio wasn’t very high so you had to actively filter stuff out to avoid your thinking becoming entirely muddled.

Romy and David joined in and pretty soon we were all deep in conversation. It seemed like no time at all before the batch director called us into the hall for the main event - the founder talk. Every Tuesday, after the batch dinner, there was a talk from a former YC founder turned Silicon Valley idol. This evening, a true member of YC royalty was back to regale us with tales of the early days.

He was an electric speaker and had the audience wrapped around his finger. The entire group laughed at his jokes. We booed when he tore apart his unscrupulous investors. We held our breath when he detailed the many near misses his company encountered. We cheered when he described his final success, against the odds.

When it was all over, and the applause died down, I was fizzing with excitement. Here he was, in the flesh. Only a few years ago, he was a hapless founder like us. And now he was up there. How he got from here to there seemed unlikely, implausible, and somewhat random. But it was possible.

Most of all, it sounded like an adventure.

“Ok, wow. You guys have lot of work to do. When can you launch?”

We were 20 minutes into our first official YC office hours session. YC styles itself after College Graduate courses and uses a lot of the same terminology you’d find in the hallowed halls of Standford, just up the road. Office hours were one example of this, named after the drop-in sessions that Ph.D. candidates have with their professors to discuss a thesis.

In this case, we were the student, our thesis was our startup idea, and the professor was one of the YC partners - who’s own qualifications included selling his startup and generating a YC record percentage return for his investors.

Needless to say, he wasn’t impressed by our lack of significant progress. Less than 24 hours before, I floated home from the dinner thinking that Impossible is Nothing™️.

Things didn’t seem all that possible at this exact moment.

I hesitated for a half second.

“Come on folks, there’s less than 3 months until Demo Day. When can you launch?”

“Eh well, it’ll probably take us another couple of weeks or so to finish our app.” I said with whatever conviction I could muster.

That would be if we took absolutely no breaks and didn’t sleep. I didn’t mention that part.

“Why do you need an App right now?”

Doesn’t everyone need an App? I really hadn’t thought about exactly why we needed one. I just took it for granted that an App would be needed. We would definitely need an App eventually, there was no disputing that. But right now?

“Hmm I guess not I suppose…but…”

“Ok so how else could you do it?” he cut across me.

“Maybe over email?” Romy offered.

“Perfect. Do some hacky stuff that won’t scale. Guess you can launch right away so.”

I guess so.

My mind was swirling a bit. Our plan for office hours was to ask for advice on quickly designing an App. Launching a “product” hadn’t really been on our radar.

“How would we do it over email?” I asked.

“Think that’s for you folks to figure out. Anything else you want to talk about?”

I shook my head. We said our goodbyes and strolled out of the office, slightly shell shocked. We were launching. Something. Over email? And if we didn’t do it in less than a week, we would have to show up again at office hours with our tail between our legs.

The clock was already ticking.

Coundown on the whiteboard