Part 3 - The Free Holiday

8 minute read

Pssssst…If you haven’t read Part 1 or 2, start here

We landed in San Francisco after the longest flight of my life. Any time I started to relax I would remember why we were traveling and then get hit by a wave of nerves. Holy shit. It was really happening.

On the plane over, we made peace with our impending embarrassment. This was going to be rough, and we were probably going to feel a little humiliated. They would realize very quickly that they had made a mistake and we would be drowning our sorrows on the Thursday night.

Free holiday to San Francisco though!

Sidenote; I kind of assumed that San Francisco and Silicon Valley were synonyms. They are not. Silicon Valley is a good hour drive south of the city, and in traffic it can be much longer.

We arrived at our AirBnB late on the Wednesday evening. It was a fairly drab apartment just off a massive highway. The development was so homogenous that it took us nearly 30 minutes to find the place. When we finally got into our apartment, we were shattered. We tried to practice a few more questions but gave up. The rest of the evening was devoted to eating pizza and watching weird TV News shows. There was some big Trump story that everyone was going crazy about.

Us eating pizza

When we went to bed, I stared at the ceiling for an hour or two before drifting off. The last time I’d felt this nervous was the night before my Leaving Cert.

For the morning of the interview we arranged a tour of a frozen baked goods factory across the bay from YC. We mainly thought that this would show hustle, or something else that would be equally impressive. If you’re getting the impression that we were aggressively clutching at straws here, you would be dead right.

We were up at about 6AM, a mixture of jet lag and nerves. We got an Uber to a café near the factory and ate an assortment of bizarre pastries. David had a strange sausage-muffin-croissant hybrid. When the time came, we decided to try and walk the 25 minutes to the nearby baked goods behemoth. Pro-tip; never walk anywhere in America. We ended up shuffling along the hard shoulder of a highway for half of it after the sidewalk petered out.

We eventually made it to the factory. It was around the corner from the Tesla plant, but it was immediately obvious that it wasn’t that sort of place. There were recruitment posters in the waiting area covered in a diverse set of beaming faces, holding various different pastries and breads. STAFF URGENTLY NEEDED. The posters were faded. The seats were clean but worn out. The staff looked tired. We later learned that they couldn’t keep employees because Tesla and Amazon paid a dollar more an hour. Who needs bread when you can get your new phone cover delivered in under a day, amirite?

After a long wait, we were ushered into a waiting room and told to don a set of protective clothing. The hat didn’t fit my head, as per usual. We went through the safety procedures and washed our hands with some pretty potent sanitizer. Then we crossed through the thick doors and onto the factory floor.

Us at the bakery

It was like a sort of dystopian Wonka factory. The machines were ancient and looked like they had survived a bombing. They were making brownies while we were there. Vast amounts of chocolate mixture were injected into huge steel trays and shoved into gigantic ovens. The whole place had a “Soviet union meets Cadburys” feel to it.

“How old is this line?”, I asked, referring to the brownie birthing room.

“About 30 years old, and we’re hoping it will last for another 15”.

Wow. We quickly learned that they couldn’t really afford the maintenance that was clearly necessary already. One section of the brownie icing machine had broken a while ago. Too much icing was squirted onto the cooked tray of brownies. Obvious solution is to fix the machine, yeah?


The chosen solution was to hire someone to scrape the excess icing off the end of each and every tray that left the oven. Yikes. Not a whole lot of use to software that tells you when something is going to break if you cant afford to fix it.

The Cloud SaaS model was also going to be a hard sell. All of the computers were running either Windows XP or Vista. And by all of the computers, I mean the 2 on the line and the other 3/4 in the back office.

This trip was supposed to build up our confidence, but it was quickly becoming clear that they would never use what we had envisioned our product to be. They were supposed to be our exact target customer. If they were never going to use it, would anyone?

As a small consolation, we were given a few bags of scones that were cooked that morning. The bags were stamped with aggressive warnings; EXCESS PRODUCE - NOT FOR RESALE. Possibly on the suspicion that we might hawk them to the highest bidder. At this stage, it almost felt like a viable alternative to our current business plan.

With our spirits dampened, we left and ordered an Uber. When the car arrived, there was someone in the passenger seat. Neither the driver or the guest really spoke English, but from some intense hand gestures and a few choice words (“learning”, “teacher”, “first”), we figured out that this was our drivers first day on the job. So we all reluctantly piled into the back seat for the 30 minute journey. Next stop, YC HQ.

The most influential startup accelerator in the world is located in a fairly boring industrial park. It’s surrounded by low, 1 story buildings filled with robotics labs, research groups, and faceless “tech” companies.

We walked into the YC building and the first thought that hit me was “jaysus it could do with a lick of paint”. The whole place is kept intentionally drab - no marble and gold finishes here. The entrance area has a grey carpet, grey couches and cream walls covered in memorabilia. Photos of gangly, beaming founders hang next to newspaper clippings from the early days - “College Students start companies during the summer holidays”. Nevertheless, I was intimidated. The building was packed and the startup founders milling about exuded a quiet confidence.

They just knew they were going to get in.

We just knew we didn’t have a hope.

YC corridor with photos

We were about half an hour early, and when we checked in we found out things were running late.

“Sorry guys, we’re about half an hour behind schedule.”

“No problem”, I said, enthusiastically, as if this was good news.

Shit, another hour of feeling like I was going to vomit. We made our way through to the main area. A massive room that must have been a warehouse or assembly line in a previous life. It was now filled rows and rows of tables. The only decoration was a Cruise self driving car parked in the corner. I felt like it was taunting me.

“This is the calibre of what we’ve funded in the past. A company making SELF DRIVING CARS!!! Are you guys really pitching something that you’ve spent a total of 3 weeks working on?”

Yes. Yes we were.

The Cruise Car

(David wants me to make it clear that this is my overactive imagination, not a real YC quote.)

The other thing that hit me in the face was that Romy was pretty much the only woman in the room. It was packed with men who were between about 19 and 35.

We sit down and nervously practice a few more questions. After about 5 minutes, another founder walks over to us.

“Hey there, excuse me. What time is your slot?”

“It was supposed to be now but they’re running late”, I answered.

“Ah ok, thanks.” He then asked us the obligatory question you must ask all startup founders. “What are you guys working on?”

Code red. We start into our pitch. I stumble a bit but it seems a little plausible.

“That sounds cool”, he offered, somewhat reluctantly.

“What about you?” I asked.

“We’re looking at creating a facial recognition system for police. We’re based out of India and we already have 300 local police forces using our system. We have about \$30k in MRR and 20 employees and this is our third time applying. I’m really nervous.”

He was really nervous. He had a product that was in use. He had \$30K in revenue! And he was really nervous…

We were so screwed it was kind of funny at this stage. He left and we started to discuss the severity of the situation. This was going to be painful. Really painful. They were gonna find us out within the first 30 seconds. We were getting a little giddy


Holy shit. The creator of GMail was gesturing towards an open door. This was it. This was our one chance. Don’t mess it up.

“Sorry folks, is that how you say it?”

Listen lad, you can say it however the hell you want, I thought.

“Yep, spot on”, I lied.

We shuffle in and shake hands with everyone one the other side of the table. They all seemed friendly enough, in an intense sort of way. We sit down on the chairs in front of them. The second my bum touched the fabric, we got our first question.

“Ok so tell me, what are you working on?”

Everything after that is a bit of a blur, but I do remember the physical sensation. It was the same pit of the stomach rush you get off Space Mountain in Disney Land. Brief suspense, then the drop. Then more suspense. Then a bigger drop. The fact that you have no idea what’s around the corner makes it even worse.

Another thing I remember is that Romy absolutely nailed it. She was a complete BEAST in the room. Every question we had trouble with previously was batted away with ease.

And they were fixated on the bread.

“The factory I worked at made 12 tonnes of bread an hour. It was…”

“Wait, hold on, say that again. How much?… I can’t even imagine that… Whoa”

We all nodded in agreement. It really was a lot of bread.

The batch co-ordinator opened the door after 10 minutes.

“That’s time everyone”

They paid no heed. The grilling continued. We must have been in there for another 5 minutes when they ask us a final curveball.

“If we don’t like this idea, would you be open to changing it?”

Christ, this was a real conundrum. Do you say yes, and show that you’re not 100% convinced in your idea? Or do you say that this is the only thing you’re passionate about and that you’ll work on it till the day you die, even if it might be a stinker? We didn’t know what the right answer was. We didn’t know if there was a right answer. So we did a bit of a fudge.

I began an impassioned defense of maintenance planning software. “This is something that we think really should exist, and we are the team to do it.” Then I waivered. “…but we’re also open to other things too…” Wow. High conviction right there.

They looked disappointed. I think this was the only wrong answer. We all squirmed in the uncomfortable silence that followed. Romy couldn’t take it any longer and went for another shot at the same question.

“I just love working with these guys, and I want to keep going. We’re a great team, I’m a really good at detail and process and they’re… well they’re just big tech nerds to be honest.”

She smiled and kind of grabbed our knees at this point. We grin for a few seconds before remembering where we were. Oh god. Did she just call us Nerds? In the middle of the interview. Romy goes bright red. David and I start to giggle. And then the crew across the table crack and start to chuckle too. It was gas.

When the awkward laughter died down, they stood up.

“Thanks so much, that’s the end of the interview.”

They gestured towards the door. We had one more trick up our sleeves.

“The factory we visited that morning had some spare scones - would you like them?”

We produce the crumpled bags of scones from behind the couch. I wish I had a photo of the look they gave us at that exact moment. It was a mixture of horror, bemusement, and respect.

I could almost hear them thinking ”They went for the hail Mary. Nice.

We shuffled back to our seats, a little shell shocked. It was all over. The interview was finished. Our fate was sealed. We didn’t say anything for about a minute before David let out a big sigh.

“Well that’s done then”

It was a little bit anticlimactic to be honest. That was it. We’d travelled 5,000 miles for 10 minutes. And it felt more like 3.

After about another 10 minutes, I went to double check with the batch director that we were good to leave. It was a bit of a formality. We were warned that there were some cases where they wanted people to do a second interview in the afternoon, but it was apparently very rare.

“They’re still discussing your interview, might be another few minutes.”

Weird. They were supposed to make a decision in 5 minutes. A bit confused, I walked back over to Romy and David.

“I suppose that means they didn’t think we were completely shit…” David suggested hopefully.

A full 25 minutes later the door to the room finally opened. One of the interviewers murmured something inaudible to the batch director. She strolled casually towards us.

“Hey folks, they have a few more questions they’d like to ask you. Mind coming back at 4PM for another chat?”

Ah yes. Another 4 hours of dread. Sign me up…

Obligatory YC Sign Photo

PS: Part 4 will be out soon. Tell yo friends :)