Part 2 - Prep and Carrot Cake

7 minute read

“I’m sorry love, this is final call, I have to close the gate”

I’m sweating buckets. Romy and I are standing next the flight attendant, waiting to board our flight for San Francisco. When we last saw David, he was crumbling like a dry biscuit under questioning from a stern border security guard. They brought him into secondary. That was nearly an hour ago. I make a mental note to strangle him in the near future.

“Do you want to go on without him?”

It’s Wednesday evening, 5 days until our flight from Dublin to SFO. We’re on a video call with 2 founder friends from the S18 YC batch. Our first mock interview is about to begin. How hard could it be?

“Ok let’s get started, what are you guys working on?” I start to ramble but I’m cut off.

“How many users do you have?”

“We’re still working on our prototype”, I answer sheepishly. This is technically true. David ran rails new monaru the day before.

“Who is your first customer going to be?” Romy tries to answer, but she’s cut off.

“Where is the rocket science here?” I look at David and Romy. They stare back at me. There’s about 10 seconds of silence.

Shit. This is going to be harder than I thought.

After 9 more painful minutes, the timer goes off. We ask for feedback. It’s not pretty.

“You have a lot of work to do. We were going easy on you, their questions will be much harder…”

“…and Patrick, stop smiling. You need to look more serious. They need to be scared of you.”

I make a mental note to change my entire personality.

At first, I thought about our interview as just another test, and the three of us have never really struggled with exams. Romy and David both had academic scholarships through college. I was a “pull it out of the bag at the last minute” sort of student, but I still managed to get solid marks.

Unfortunately, this wasn’t really an exam. It was more like an interrogation, where every right answer led to a dizzying array of connected questions. And every wrong answer led to a crushed dream. No pressure.

There was also the minor issue of having no product, users, or real plan to speak of. I’m used to flying by the seat of my pants, but this was taking the piss. Our preparation was made even more difficult by the fact that we were all working 9-5 and David was still over in London. Monday to Friday of that week was a blur of working at my day job until 6 and then on Monaru until I could no longer keep my eyes open.

After the first few days of mild panic, we started warming to our idea a bit more. Maybe manufacturing plants really did need new maintenance planning software. We built out a plausible, if slightly contrived, pitch. We lined up visits to factories in Dublin. We spoke with about 10 different maintenance engineers.

By the time the weekend rolled around, we were feeling a bit more confident. A VC friend in Dublin gave us access to a room in his office for Saturday and Sunday. David was flying in from London and we were all set for two days of heavy preparation. That was loads of time, right?

Wrong. lol.

We arrived at 9:30 in the morning, and for some inexplicable reason we spent about 2 hours ruminating over what our company values should be. With half the morning gone, we settled on some assortment of “be nice” and “work hard”. Time well spent eh?

One side-note; the proliferation of start up culture has lead to a Cambrian explosion of resources that are supposedly written to help people start their own companies. A significant amount of these articles, videos, listicles etc. are actually just content marketing for [startup].io . It’s super easy to be lead astray by a random Medium post that tells you to plan your first VP hire (should it be VP of Sales or VP of People?!?!!) before you know who your customer might be. While this is obviously bad advice, it’s still easy to get sucked in and lose valuable time worrying about the wrong stuff.

There is also this crazy compulsion to replace a hard problem (build a profitable business) with an easy problem (decide what you want your corporate motto to be). Don’t do it. Or at least try not to. Try really hard because you will inevitably spend a significant % of your time on random shite. Part of me thinks that doing a startup is one big game of avoid things that are obviously a waste of your time.

We asked a family friend who has some experience in investing to give us a dummy interview in the afternoon. With 4 hours to go, I felt like we had more than enough time to prepare. We started into some practice questions when my phone rang.

“Hey I’m outside, does now suit?“. He was 4 hours early.

“Sure thing, now is great!” I lied.

“Ok, so I’ll be honest, I’d never invest in this”. Just the kind of encouragement every budding entrepreneur dreams of. We stumbled through 10 minutes of humming and hawing. Turns out we had made less progress than we thought.

“David is it? David, I don’t think you said a single word.” He hadn’t.

“Romy, you need to be more confident - you looked like you weren’t sure about your answers.” This was the most worrying part. Romy froze up when answering the kind of questions that she should have nailed. She is an expert in machine maintenance ( she hates it when I use that word but she really is ). The questions that came up were softballs but she still struggled.

“Patrick - you really don’t seem interested in any of this. You’re talking quickly but you look bored.” Ouch. This stung. I spent the whole mock interview trying not to smile. And I succeeded. But it sounds like I lost my mojo along with my smile.

“The thing that stood out the most was that you three didn’t know who should answer what. You talked over each other the whole time.”

Shit. YC explicitly calls out clear team roles as something they’re screening for. Not only were we bad individually - we also looked lost as a team. We had a lot of work to do.

We threw our plan out the window and spent the rest of the afternoon grilling each other using the YC question generator. At about 7 PM, Romy remembered that is was her brothers birthday - she wanted to run out and get a box of chocolates before the shops closed. After she left, David said offhand that he has the same birthday as her brother…

David hadn’t mentioned once that it was his feckin’ birthday. He’s one of those weirdos who takes it off Facebook, creating a sort of cruel How well do you really know me test. At this stage I obviously didn’t know him very well at all. I ran out and grabbed a cake and some of David’s favorite beers (Desperados) from the centra next door. We had the most miserable birthday celebration:

David stayed with me on Saturday night and we watched the first few episodes of the HBO mini series Chernobyl. They definitely could have done with some maintenance planning software.

Sunday was more of the same interview practice, with small breaks for David and I to try and glue together a mock up of our imaginary software. At this stage, I’m close to tears trying not to smile while answering questions. It might seem like a simple change but I always smile when I’m getting excited or feeling high energy. It feels like I’m imitating someone else.

We decide that we should codify who answers what. Romy would answer any questions related to the factory. David would answer anything to do with the product. I would be in charge of the opportunity - how big this could be.

I also act in a kind of sweeper role for any curveball questions that came up. We make up a game where we read out one of the practice questions from the generator, close our eyes, and raise a hand if the we think the question is for us. For the first half hour of this, every question is either all hands in the air or none. Brilliant.

We eventually got in the swing of things and by the early afternoon we were a well oiled machine.

“What are you working on?” - Zinger from Romy.

“How does the product work in detail?” - Nerd talk from David.

“How big an opportunity is this?” - Hand waiving from me.

We had one final Mock interview with our VC friend in the early evening. At this point, I’m tired out and can barely concentrate. It felt like altitude training - if we could pitch in this state we could pitch anytime, anywhere. I hoped.

I made one small change this time. I didn’t have the mental energy to stop smiling. So I sat there grinning through the whole interview. And I felt way more relaxed.

I thought this one went pretty well. Romy still got a bit flustered but we powered through. David even answered a few questions (that was a first). The most important thing was that we were no longer talking over each other. Even if one of us butchered a question, we all nodded along and stayed positive.

I could tell my VC friend was a tad impressed. Then curveball number 2 hit us in the face.

“I’ve been chatting with some of the team here, and we’d like to give you some support to keep working on this, even if YC say no.”

Wow. Shit just got real. This caught me completely off guard. Part of me felt like we were going to head over to California, meet some startup celebs, and then return to our normal lives. That definitely wasn’t going to happen now. And I got hit by a wall of self doubt. Were we ready? Was I ready? We were about to find out.

Mr Big VC friend brought us to Thai restaurant around the corner to celebrate the weekend of frantic preparation. My head was still spinning but we were feeling pumped and ready to rock. We had some sturdy answers for most of the hardest questions. David and Romy, who had only met a few times before the Saturday morning, were getting on like a house on fire.

We were still objectively goosed though. Our MVP consisted of an essentially un-styled Vanilla Rails app (praise our lord and savior DHH, maker of generator commands and slayer of VC twitter influencers). We had no customers. Or potential customers. Or distribution strategy. Or pricing model. Or plan.

Whatever. Three more sleeps until I was going to be in a room with some of my heroes. It was possibly the most exciting week of my life.

Just as Romy and I made the decision that we were leaving without David, I saw a goofy figure bob up and down in our direction.

“Run you feckin’ eijit, they’re closing the gate.”

“Oh shit, that was close. Were ya gonna go on without me?”

“No way”, I lied.

A few minutes later I settled in and took my seat. The engines started to roar. The journey that was about to alter the course of my life had begun. I took a look at what was on the in-flight entertainment system.

Silicon Valley Season 1.