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Part 4 - Uber for Dogs

9 minute read

Pssssst…If you haven’t read Part 1, 2, or 3, start here


My mind was still racing. The second interview was going about ten thousand times worse than the first. After the first bombshell (that they hated our idea but liked the team), we tried an impassioned defense of maintenance planning software. It fell on deaf ears.

“Ok well, you did share some other ideas with us. Let’s look at those…”

Oh shit. I’d forgotten about that part of the application. There was a box where they asked:

If you had any other ideas you considered applying with, please list them. One may be something we’ve been waiting for. Often when we fund people it’s to do something they list here and not in the main application.

It was one of the last questions on the application. We literally spent less than a minute on it (David wanted to go to bed). There was a decent chance those 60 seconds were about to decide whether or not we’d be handed 150 grand. LOL.

And then I remembered. Oh god. Oh Jesus, Mary, and Joseph. Why the hell did we think it was a good idea to put in a joke…


“Ok, so I actually think there’s a chance we might get in…”

We were sitting in a fairly shabby Sushi restaurant in Mountain View, a 20 minute walk away from YC headquarters. Mountain View is one of the two centers of modern Silicon Valley, the other being Palo Alto and the Stanford campus. In the late 2000s, cool new startups started moving up to San Francisco, but much of the Venture Capital world and many bigger companies still gravitate towards this part of the bay. Sand Hill Road, a place of nightmares for many aspiring founders, is the epicenter of the VC world. It has the most expensive real estate prices in California, a fact that VCs love to mention.

We had nearly 3 hours until our second interview. And we were shattered. Given that we had been in California for less than 24 hours, we were 100% still working off our home time-zone. Our first interview had been at 8:30 PM Irish time. Not the end of the world. Interview 2 was scheduled for 4 PM PST, AKA midnight… I had slept for about 5 hours the night before, and maybe 3 on the flight over. I felt like I was participating in some sort of sleep deprivation experiment. Should you take part in potentially life-changing activities while deliriously tired? Probably not.

“Romy, you absolutely bossed that. You just have to do it again” I said, trying to make it sound like the easiest thing in the world. She didn’t look convinced.

“I wonder why they are asking us to do another one?”


We made it back to YC with about an hour and a half to go. At this stage, I was chugging Red Bulls. Once again, we were getting very giddy. We spent some time practicing questions, then decided we needed to chill for a bit. We had a little photoshoot with David’s iPhone:

Me gigglingRomy smiling
David looking cute
Us with the YC sign

Then we played a game where we tried to think of ways that each of us could get YC to definitely not pick us. Only rule was that it couldn’t be too obvious that we were trying to throw the interview.

David’s method was just not talking for the entire interview.

Mine was to cut across Romy whenever she tried to speak. Clearly that would have gone down really well.

Romy’s was to keep asking me and David for permission to speak. Another very positive team dynamic.

The room was full when we arrived back but as we inched closer to 4 PM, it started to empty. We assumed that we were being extra careful and that the second interview cohort would arrive soon. But after another while, we realized that we were the last ones left. What the hell was going on?

I have a tiny bladder, and when I get nervous I need to visit the bathroom about every 10 minutes. I was getting a weird look from the batch director as I walked back past her desk for the 6th time after visiting the restroom.

“Sorry for the slight delay, they’ll be ready for you in 3 minutes”

Ah holy moley this was it. I scurried back over to David and Romy. I could see them both yawning as I approached.

“We’re on in 3 guys, let’s do a shakeout!”

We’d taken up the practice of doing one of my college drama society warm-ups before the different pitch meetings. And by taken up, I mean that David and Romy were participating entirely against their own will.

We stood in a corner of the room that we thought was out of sight and got started. The shakeout involves shaking each limb for 8 seconds:

“1,2,3,4,5,6,7,8”

And then for 4 seconds, then 2, then 1. It ends with a jump and a shout of some chosen word. In this case, “MONARU”.

We finished with a flourish and turned around to see the batch director staring at us.

“They’re ready for you now…”


David was making a pretty good case for his “Better version of Blackboard” idea, which was good news for two reasons; 1, I was completely blank so someone else talking was great. 2, it was the only idea left on our application above the one we didn’t want them to ask us about.

Uber for dogs.

If you had any other ideas you considered applying with, please list them.

GANS for endless Audio Content

A Better version of Blackboard

Uber for Dogs

We wrote this on our application. To YC. In hindsight, I can’t really explain why. We took the rest of the application seriously. We wrote some pretty interesting points about the details of the manufacturing maintenance planning software market. It was a thorough, forensic, and grown-up examination of a fairly boring topic. So much so that there was a strong danger that the joke was not going to be obvious to anyone reading it.


David was finishing up his pitch. The ice was starting to fill my veins again. I needed to think of something, anything, to convince them we were worth taking a bet on.

“Wow David, you have me convinced anyway”, I blurted out.

I glanced up at the other side of the table and the YC team looked confused. Then I realized what I’d said and let out one big laugh. I had just made it obvious that this was the first I was hearing of David’s genius idea to revolutionize Third Level education.

This was not going well.

I tried to think of something, anything, to say to plead our case. Before I could start my speech, one of the YC partners cut in. Let’s call him Finbar (obviously not his real name).

“Ok, that’s the end of the interview. This is an unusual situation. We like you guys but we don’t think any of these ideas are all that great. Why don’t you send me an email at finbar@ycombinator.com with any more ideas you might have and we’ll go from there.”

Silence.

What the hell does that mean? YC is very clear on how the interview process works. You do one 10 minute interview in the morning. If you’re in, they call you after 6PM. If not, you get an email before 10PM with some thoughts on why they didn’t pick you. Simple and straightforward.

After our rambling 30 minute interview numero 2, we were well off the beaten track here. And now this curveball. I decided that I should try and clarify what he meant.

“Sorry, not sure if I fully understand. Are we still being considered for this batch?”, I asked very tentatively, as if I felt neutral about the potential answer.

“Just email me at finbar@ycombinator.com and we’ll go from there.”

The batch started in less than 72 hours. We all still had jobs in Dublin. If we got in, we would have to go home, pack up our lives, and then come back to California for 3 months. Time was somewhat of the essence.

I nodded, as if that cryptic answer was sufficient, and started to stand up out of my chair. Romy is much more assertive than me in these situations, and she tried to get a more solid answer.

“Sorry that wasn’t clear at all, are we in or not?”

“Just email me, finbar@ycombinator.com…”


About 30 minutes later, we were riding the CalTrain to San Francisco. The CalTrain is a bizarre piece of public transport. The train cars are massive and imposing, two stories of corrugated metal. The interiors are solid but faded. It looks and feels like jumbo version of a rural train connecting two remote cities, sort of like the old CIE diesel trains that would take you from Castlebar to Longford (two small towns in Ireland).

But in the center of the tech capital of the world, it couldn’t be more out of place. Somewhere you’d expect to see a TGV style bullet train, or a Japanese Maglev, you get a rickety and slow-moving beast that would look ancient by rural Irish transport standards. America is weird.

We were still somewhat shell shocked by what had just happened. We went into the morning thinking that, worst-case scenario, we could have a big night out and drown our sorrows in San Fran. This uncertainty felt 100 times worse.

We started to speculate on what might be going on. Maybe they were going to offer us a space in the next batch in 6 Months time? Maybe they would actually change their mind and let us in on one of the ideas we had already pitched? Or maybe…

“Guys, this is another test…”

A bolt of energy shot down my spine and my ears tingled. I could feel the excitement rising - we still had a chance. They started to contact successful teams at 6PM. It was 5:22PM. We still had a brief window. We just had to send them a few good ideas before then and we were sorted. Or at least that reasoning made complete sense to my sleep deprived brain.

We started drafting the most important email of our lives. Our one final shot at moving the needle. We just had to come up with, and then succinctly pitch, a few \$1B ideas. In less than 48 minutes. EASY.

I’m reading back the email we drafted now, some 11 months later, and honestly it’s a work of art. It has the sort of slightly deranged, yet perfectly logical tone you’d imagine the letters a serial killer sends to the police might have. Completely reasonable, totally insane.

Here it is, in full.

My personal fav one was NicePolitics. LOL. I’m not saying we called Clubhouse but 🤷‍♂️ Also:

Thank you so much for the feedback today. The experience was extremely validating for us and we have never felt closer as a team.

🤮

We then spent about 30 minutes trying to send it. There’s no WiFi on the Caltrain, so we had to hotspot off my phone and use my roaming data. Within seconds I maxed out my limit (all 40Mbs) and we didn’t even get the email sent.

Trying to get the email sent

We sat in frustrated silence until the train arrived into SF. Romy sprinted ahead with her laptop and dove into the nearest Starbucks. Within a couple of minutes the email was sent. Time - 6:22PM. We had missed our imaginary deadline.


The rest of the evening was surreal. We met up for dinner with our Irish friends / mentors who were in the S18 batch and told them about what had happened. They were flabbergasted.

“Hold on, you gave them scones at the end?!” They went white. This was obviously not allowed. When I told them about how I congratulated David on his idea during the interview, they grimaced. Another faux-pas.

“Well they’ll definitely remember you…” they offered eventually, as a sort of consolation.

It was well passed the time that successful groups were supposed to be contacted. We were now waiting for the axe to fall. I was aggressively refreshing my email to get the final confirmation of our failure.

But it never came.

At Midnight the restaurant closed and we shuffled back to our Airbnb. We’d planned a mad night out that involved a Karaoke bar (either to celebrate our success or soften our disappointment), but we were so shattered that we just went home to bed.


David and I were flying home at 4PM the next day. Romy was sticking around until the Sunday to spend some time with a friend from college. We spent the morning trying to enjoy some touristy things, but we couldn’t help but speculate on what our fate would be. We still didn’t know if we were going to be leaving our old lives behind and high tailing it to Silicon Valley for 3 months. Or if this would all evaporate like a fever dream and we would be back at our desks on Monday morning, as if nothing had happened.

At 2PM we had lunch with our Irish friends and and then said our goodbyes. Still no word from YC. Romy, David and I did one last shakeout and then we ordered an Uber. What happened next was possibly the weirdest part of the whole story. When I opened the door, staring back at me through giant, gleaming eyes was…

A dog.

In our Uber.

It was an Uber with a Dog. Close enough.

Uber for dogsUber for dogs

David and I arrive at the airport and walk towards the check-in desk. We’re engrossed in the conversation du jour; WTF was going to happen next?

“Sir, please place your bag on the belt”

I bend down to pick up my bag when my phone starts to vibrate. I drop everything I’m holding and grab it out of my pocket.

“Orange Lima is calling you on Skype”

I had made a Skype account for one reason and one reason only. To communicate with YC.

“Its…Its…Its…them”, I stutter breathlessly at David. He grabs my stuff and I dart out of the queue.

I answer.

“Hi, Patrick speaking.”

“Hey Patrick, It’s Finbar”

My knees buckle but I manage to stay upright. “Hey how are you?”

“Good, let’s get to it.” he booms, as direct as ever.

“We had a look at your new ideas and we don’t really like any of them either.” My heart sinks. The axe was falling. The dream summer spent in Mountain View, learning all about how to Make things people want, was evaporating.

“But we like you guys, so we want to offer you a place in the batch anyway. If you agree, we’ll meet up ASAP and discuss some ideas.”

I’m dumfounded. It takes my brain a second to process what he just said. David has Romy on the phone at this stage. I mouth at him, “We’re in”.

“Is that something that would be of interest to you folks?”

I drop all pretense of being aloof or neutral here.

“100%, yes”, I almost shout at my phone. I look over at David. His eyes are welling up. I feel mine start to fill. This was going to change everything. Against some pretty hefty odds, we were in. WE WERE IN. I spend about 5 minutes answering some formal questions ( Do you agree to the terms of the YC agreement etc. ) and then arrange a time to call him back. Then I hang up the phone. And I hug David. And we jump up and down until the beefy security guard in the corner waves at us to stop.

All we had to do now was go home, quit our jobs, find somewhere to live for 3 Months in California, and then come up something that was actually a good idea. Simple.

Quick user research question:

What if I told you there was an app on the market that could get your Dog from A to B? Would you be:

Somewhat Excited or Very Excited?

Pick one…


The frantic letter from the CalTrain:

Hi Finbar,

Thank you so much for the feedback today. The experience was extremely validating for us and we have never felt closer as a team.

To be honest, we were caught a little off guard with your question - since we got the mail a week and a half ago, all we have been thinking about is factories to prepare for today. With a little time, and reflection, there are a number of other areas that we, as a team, have a collective interest in.

Distream: Distributed Amateur Sports Streaming

An application that allows spectators at amateur sports events to livestream the match from their smartphones and receive payment for it from remote viewers funded via advertising / karma points from their peers.

Patrick plays rugby at the highest amateur level in Ireland and David had no way to keep up with Patrick’s matches when he moved to London.

Romy’s family are massive Gaelic Football fans ( an entirely amateur sport that is the most popular sport in Ireland ). When they miss local club games ( none of which are televised ), the only alternative is to follow along on twitter.

While US sports are usually televised, in the rest of the world this is less common. The idea is that the long tail of sports games that aren’t televised still have a willing audience and smartphone cameras have improved so much that the picture quality would be adequate. Also if more than one spectator streams you could view the game from the best available angle etc.

Long term this could become the default sports streaming service around the world.

NicePolitics:

A constrained politics focused social media platform where users can upvote a constrained set of questions on topical issues. Registered and verified politicians can respond to the questions and converse with each other.

The main idea here is that if you constrain the ability of individual users to comment / troll politicians and force politicians to talk to each other, you could create a much higher level of political discourse on important topics.

Better Blackboard:

We spoke a bit about this in the interview. Having all gone to university we felt like there are significant opportunities to improve the experience for both students and lecturers. We talked about the scheduling aspect to allow lecturers to choose optimal due dates based on student capacity. There are also a bunch of other features including: reminders to submit assignments, ability to search content (in slides), group project organisation/sharing, revision note sharing, student engagement (who’s logging on, what content is being viewed).

Let us know what you think of these projects, we think Distream is the biggest opportunity but we look forward to your feedback,

Thanks again,

Romy, Patrick and David


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