Reflecting on my notes from YC Startup School 2014

Throughout college and for a few years after graduating, I made it my mission to put daily effort into my online presence. I was inspired by those who acknowledged the importance of writing and blogging, like Paul Graham and Joel Spolsky.

Over the years I've failed at putting any effort into maintaining this presence and didn't write for almost two years. I've let many of my older websites and apps die. I didn't engage on Twitter, and my participation on any platforms was rare outside of random one-off comments. In the later half of 2019 and after six years of working experience, I started to become more serious about honing my writing skills, so I began taking steps toward change. One step was getting a basic personal website back up and running, while also making efforts to blog more. That's how and came to be.

One interesting bit of data that came out of my new website was that I noticed a decent amount of traffic to older URLs that are no longer available. The one receiving the most traffic was /startup-school-notes. This was a basic list of notes that I took live at YC Startup School 2014, back when it was more of an in-person conference.

This morning I scrubbed some old hard drives and found the content for that page. I've resurrected those notes here →

In the remainder of this post I will review a few gems that have aged well over the last 6 years.

One feels the need but they both build or work on the idea

Ron Conway, SV Angel


Work on interesting problems with other people (PG)

Paul Graham, YC

There's this prevailing wisdom in the valley that it's one brilliant CEO that comes up with the idea. Or even if it's not the idea, that CEO typically is seen as the genius. There are countless examples - from Elon Musk and Jeff Bezos, to lesser known but equally respected founders, like Justin Kan and Patrick Collison.

The fact is that it takes a founding team to build a company, and founders typically aren't given the respect or notoriety they deserve (as a team). Often it's the CEO (regardless of if they are a co-founder) that is given the attention and recognition. Regardless if this is good or bad, it's important to remember that when starting a company it's nearly impossible to do by yourself. Build a team with smart, reliable people. Take time to build those relationships.

Traction is the only way to tell if a product is working

Ron Conway, SV Angel

How do you know you're building the right product? How much traction is enough traction? Do I have product market fit? What are the metrics I need to prove that it has traction or not? It's all a dark art. Like many dark arts, the response you feel is greater than the numbers on the page. When you have traction, you know it. In enterprise that may mean hitting $10m in revenue. In the consumer space it may mean 100k monthly users. Whatever it is, it must be felt.

Be intentional with your culture (because it's always happening)

Danae Ringelmann, Indiegogo

Building the right culture and hiring the right people go hand in hand. Focusing on intentional culture is one of the most important aspects of building a company. Too often founders ignore culture. The problem with failing to be intentional is that culture is built regardless of if you focus on it or not. When you don't do it intentionally you end up with horrendous company culture.

Take the idea of a 'perfect' next move and throw it out the window

Kevin Systrom, Instagram

This statement not only applies to building startups, but building a career in general. Setting yourself up for future success doesn't mean plotting out every move. Some of the best opportunities I've had have come from unplanned next moves. Always be open to new and exciting opportunities, even if it means taking a big risk.

Be relentless. Everyone will tell you your idea sucks

Kevin Systrom, Instagram

This is perhaps my favorite quote of the day. The only way to build a massively successful startup is to be absolutely relentless. Be undeniable. Hundreds of VCs will tell you no (or worse yet, ignore you completely). Even more random internet users will tell you that your idea is terrible.

The only thing you need to worry about is what your users are telling you. What's working, what's not working. Forget about your idea. Ideas are only as good as their execution. If you have conviction and the ability to execute, then fuck everyone else. Just do it.

The myths of SV entrepreneurship: you need the most amount of capital (raise more than you think to get to a milestone, 20 million means raise 25-30...not 50). Money is not the time. The market is the time

Reid Hoffman, LinkedIn

Some of the most financially successful startups in the last five years have applied this principle (Zoom, Notion, etc.); while other startups that have raised insane amounts of money don't appear to be doing all that well (MagicLeap, WeWork, etc.). If you're raising money, then be deliberate about the amount. More importantly, understand the market timing. A poorly timed market will kill the best product, with the best team, and the most amount of money.

Investing: if 100% of people think it's good there are problems you aren't seeing

Reid Hoffman, LinkedIn

Novel ideas often look dumb on the surface. I still have a hard time believing AirBnB is a legitimate business. Hotels are far superior in terms of amenities and service, and are often cheaper. But AirBnB is a true unicorn worth billions. When you're vetting startup ideas there needs to be something so futuristic about it that people will say it's dumb. If it makes sense to everyone and doesn't exist, there are likely big reasons why that's the case.

Jan: Worked for Yahoo for 9 years

Jan Koum, WhatsApp

This wasn't really a quote, but a fact worth repeating. Another silicon valley fallacy is that you need to be 22 years old and a college dropout to build a billion dollar business (or something like that). The truth is that the founder profile is rather varied, and many don't strike success until they are well into their 30s and 40s.

Jan: at 150 million users they finally hired customer support staff

Jan Koum, WhatsApp

This stands out to me as a core principle for WhatsApp. Everything about that company shows efficiency. From how they never really needed external funding, to their small employee count, to the fact that they had 150 million users before they hired support staff. That type of growth and efficiency is rarely seen from startups today.

Jim: WhatsApp has no marketing or finance department

Jim Goetz, Sequoia

Similar to the point above, this shows again the efficiency of WhatsApp at managing their business. It also points to the value of their product. They didn't need to market. They timed the market so remarkably well that they completely eliminated the need for an entire department previously thought to be table stakes.

The first version of Groupon was a WordPress (site)

Andrew Mason, Detour/Groupon

No code/low code is even easier today than it was in 2007. The fact that Groupon started as a WordPress site should give you some idea on how relatively low the tech bar is for starting a company. Certainly if you're building a consumer, mobile-first application it's a bit harder. There aren't many options to no-code an iOS app. But if you're building a consumer brand or even a low-tech SaaS product, there are ways to do it without having to be an engineer.

If you have to ask what each co-founder is going to do, then you may have the wrong co-founder

Michelle Zatlyn or Matthew Prince, CloudFlare (I don't remember who said this one)

This is a very important point for founders. Titles are titles. You can figure those out. But it's imperative that there's an understanding of each founder's responsibilities. If there's any ambiguity it's going to end badly. This is why I always suggest founding a company with someone you've worked with previously. You go into the engagement already knowing each others' strengths.

They still talk to every candidate that they hire (the founders)

Michelle Zatlyn or Matthew Prince, CloudFlare

Another point that should be noted by founders. If you're not talking to everyone you hire then you're doing it wrong. I would say this is the case even up to 500 employees (and beyond if you can pull it off). That may seem like a logistical nightmare, but people and culture will make and break a company. I've seen the aftermath of bad hiring and it will cost you a lot of time, money, and trust from your team.

You don't want people to be bored. Ever.

Michelle Zatlyn or Matthew Prince, CloudFlare

This is a bit nuanced. It doesn't say anything about being busy. It specifically states boredom. When employees are bored they start to look for other jobs. The employees that will stick around when they are bored aren't the ones you want around.

Early on its a roller coaster and it's no different 5 years later

Michelle Zatlyn or Matthew Prince, CloudFlare

Another point that can't be understated. Every. Single. Startup. is a dumpster fire. Each one has its own version, but they are all on fire all the time. If you find a company with a super hot product then their culture might be shit. Or a company with a stellar culture and a stellar product might be hemoraging money.

I personally love fires. I love existential threats. It keeps it interesting. The last thing I'd want to do is sit around at a mega corp working on some minute detail of some minute product. If that's your thing, then great. Do that. You can make a great living. Everyone at a startup is taking a risk including employees. If you're risk averse then don't join a startup.

Thanks for reading! I’m still growing this blog, and if you feel that someone you know might benefit from this article, I encourage you to share. You can also subscribe to all updates by clicking the button below. Cheers!


How I Use Notion

Notion is all the rage, and rightfully so.

Before switching to Notion, I struggled to pull together a set of reliable productivity tools over the years. Generally I'd find a new note taking app or a new todo app every 6-9 months, never sticking with anything beyond a year.

It's hard to put to words what exactly I didn't like about any one tool I used. What I suspect was going on was that subconsciously I wasn't happy, for whatever reason, and my mind was on this artificial timeline. So when six months rolled around, I'd feel the urge to go googling for whatever was being billed as the next great tool.

In this article I'll briefly cover how I started using Notion, and then give a more in depth overview of how I use Notion today.

Notion ca. 2015 - source:

I first remember Notion from when I attempted to use it in late 2015. I didn't really know what it was at the time. Someone had initially floated it to me as an alternative to Confluence, but I knew my company wasn't ready to move away from Confluence yet. Even for personal use I didn't see the draw. I had Google docs, I had Things for tracking tasks and I had Evernote for taking notes.

Notion today - source:

Fast forward a few years and I found Notion yet again. By then I had gone through several iterations of my productivity stack, having used:

Not joking, I've used literally ever single one of these apps extensively. The core problem that I was trying to solve was integration. All of these tools had components that worked great, but none of them were integrated, or connected to any other apps in meaningful ways. Taking a note in Simplenote felt meaningless when I couldn't connect it to a task in Things 3, or expand on it in a MacDown document. Yes, I could copy and manually tie all of these tools together via tagging, and organizing, but that's a nightmare.

So in January 2019 I started using Notion and I've not looked back since. It has solved every problem that I've had with any other tool. It supports markdown, complex media types, taxonomy, organization, templates, and much more.

My Notion Setup


My Notion settings


Create a custom icon. It looks better than an Emoji; or at the very least use an image for your Notion space icon. It gives your space character. You're going to be looking at this app almost everyday, you'll want to introduce character where you can.

Dark Mode

I'm a dark mode purist. I have dark mode on by default for any app that allows it, and I generally gravitate towards apps that have darker UIs. I don't know if this is a habit from using a code editor for years, but I prefer the way it looks and it's easier on the eyes.


I'm on the Notion personal plan ($4/m), which only allows one user. This has made collaboration with my wife a bit difficult at times because she doesn't use it enough to justify the $16/m it would cost me. I do wish Notion would introduce a family plan.

That's it for settings. Notion doesn't have any extensive nobs or levers to pull just yet. I am hoping they release an API in early 2020 for building integrations and even using Notion as a CMS.


My notion space is split into two working sections, Personal and Work. I use these labels as tags and generally any top level item gets tagged with either. The two exceptions are Launchpad, which is where I start the day. and Templates, which is where I store all of my templates. Everything else is either work or personal related.

My Notion navigation structure


Launchpad - where I start the day

To start my day I typically go through my emails, making todo tasks for follow ups, and organizing those tasks by priority. From there I will go through the rest of my backlog of todos and figure out what I need to work on that day. Beyond that it's a blur of meetings, slack discussions, and general startup chaos. Because of this I need a solid foundation on which to start my day. Launchpad provides that foundation. From the most important links, to internal/external documentation. My Lanchpad has everything I need to get going.


Templates in Notion can be very powerful. Once I've settled on an outline that I like, I'll save it as a template and store it in the Templates directory. From there, I can create copies of it for use within a Notion directory. If you're not familiar with Notion's template button, it allows you to quickly produce a series of page blocks either as their own separate page, or as elements on an existing page.

Wrapping Up

In the future I plan to leverage Notion's API (hopefully coming soon) to manage all of my content across personal, work and web spaces. I plan to manage website content, social media content, and even product related content, centrally with Notion. This would bring Notion closer to Airtable in terms of functionality, but with a far superior UX.

I’m still growing this blog, and if you feel that someone you know might benefit from this article, I encourage you to share using the button below. Thanks for reading!


Markets Endure

A market’s true size is determined by its proximity to the human condition.

Think of a human as the trunk to a tree. The core branches of that tree are the stuff that keep us alive — sleep, sustenance, shelter, money, health, etc. A market’s proximity to these essential branches determine the potential of capitalistic success. Spanning these branches means an even higher likelihood of success.

The further up the tree you go, the smaller the market becomes until eventually you don’t have a viable market. The trick is to not mistake your market for your niche. Starting with a small subset of a larger market is a niche. You create a product that a small number of people rely on. You make it so good they evangelize it. Then you grow to meet the needs of the larger market.

Issues arise when you conflate your niche and your market. What you may think is your niche, may end up being the entire size of your market and then you’re in trouble.

I’ve witnessed this happen first hand. You’re building a product, you’re talking to customers, you’re shipping code, you’re improving the design — it feels like you are hitting product market fit…and then the sales fall off a cliff. A year later the product has 20 customers, the same number it had a year ago. Your market, which you assumed was your niche, may in fact have been just 20 organizations. This happens with highly specific B2B software and can often kill a company that doesn’t know any better.

If you’re starting a startup it’s imperative you understand the difference between your niche and your market. Build your product and GTM for your niche, but know from the beginning how that blooms into a billion dollar opportunity.


The monsters of product, are contained within.

Welcome to Kaiju, where I write about product strategy, management, marketing and operations — with occasional articles on startups, equity, and capital management.

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