My Takeaways: YCombinator’s Startup School

A few weeks back I have signed up to Hacking Health – UC Berkeley’s Hackathon focused on Digital Health. Having an interest in that area of technology, I was looking forward to attending and competing. However, shortly after signing up and paying a $50 fee (refundable for those who attend) I found out that I got accepted into this years Startup School. The two events are going on at the same time. What I am to do?

The hackathon starts on Friday afternoon, in Berkley, with some speakers and proposal pitches. The bulk of coding takes place on Saturday and final presentations and winner announcements happen on Sunday. Startup School is an all day Saturday event in Cupertino. The distance between the two, the time it takes to go between them via public transport and the BART strike this weekend makes this a logistical nightmare. Perhaps I should skip out on one? It would either mean losing the $50 or missing out on some amazing speakers.

That didn’t seem very entrepreneurial so I decided to attend both. Startup School in full and the Hacking Health for pitches and demos (that way I would get to see what people were proposing and what they actually managed to come up with – and I get my money back).

I have said in one of my first posts that I will use this blog as a tool for reflection. Having gone through Startup School I feel that I need to summarize my takeaways in a format that I can later return to. Hopefully you will find this useful also!

Phil Libin – Founder, Evernote

IMG_4810Perhaps this is because I am a huge fan of Evernote, but Phil is one of those speakers this is in a category of his own. His messages always strike home through the connection that he builds with the audience. For anyone looking to start a company or, more specifically, build a product I highly recommend this talk he gave at Founders Institute. I really liked his opening speech yesterday. The main takeaways for me were:

  • Find something to build that is sufficiently epic. Make it your life’s work.
  • Make something for yourself, something that you love. If you make it for yourself you will be able to judge whether its great – whether you have achieved greatness.
  • Don’t make friends with people who you can’t see yourself starting a company with.

Dan Siroker – Founder, Optimizely

Dan message was incredibly focused. He gave some background as to how Optimizley came to be. It wasn’t his first company, but as he pointed out is was the one that had the shortest time to the first paying customer from the first line of code. Throughout his different ventures he always used customer feedback as input for what to build next. He listened closely to his audience. It was also interesting to see that each of the companies that he started have roots in the frustrations of the previous one.

Ron Conway – Partner, SV Angel

IMG_4812Ron was interviewed by Jessica Livingston and as such spoke about may different things. However, what really resonated with me was when he spoke about traits of great entrepreneurs:

  • 100% focused on the product and giving users a great experience.
  • Being decisive.
  • Hire fast, but also fire fast to keep the momentum.
  • Team builder. When evaluating whether to invest in a company Ron asks him self a question of the founder: Could this person lead a team of 1000 people?


Balaji Srinivasan – Founder, Counsyl

Balaji’s talk was rather politically oriented, taking a stab at the government vs Silicon Valley. It fostered an us vs them attitude in the room. Personally I am not too concerned with politics at the moment so more than anything I found that part entertaining. However, there was an underlying message of Exit vs Voice (based on this book). The basic idea is that anyone working for a company has two choices when they disagree with something going on / want to see it done better. That person can either voice their opinions and lobby for change or they can say ‘Right, I’m going to opt out of this, quit and do it myself’.

His online programming course for startups might be of interest.


Chase Adam – Founder, Watsi

Even though Chase started off by pointing out that his presentation will be neither informational or motivational it definitively ended being inspirational. I suspect for founder of a non profit organization it is fitting that he would be modest.  A few takeaways:

  • He would think about Watsi for 10-15 hours a day about all the problems that could come up and he would try to come up with solutions.
  • When you give people something for free they end up not giving you bad feedback fearing that you will stop giving it to them
  • In the beginning focus on 1 key metric.
  • During  fund raising they took 136 meetings over 3 months in 5 states – this puts hard work into perspective!

Jack Dorsey – Founder, Twitter, Square


This was a rather unconventional talk. Jack took to stage and began reading from The Art Spirit, giving his input occasionally. He then read from The Score Takes Care of Itself. If that wasn’t unconventional enough he then asked everyone to listen to one of his favorite songs, and for 3 minutes everyone just listened.

He spoke about the importance of the work (turning ideas into action) and finding your own path. He said that it can be easy to copy others in hope of success. To do this we have to start building what we want to see in this world. That way we can let our passion shine through and others will become enticed.

Mark Zuckerberg – Founder, Facebook


Mark was interviewed by Paul Graham and it was everything you could imagine if you have heard him speak before.  Mark was charismatic and insightful in the way he spoke, without seeming like he was trying to be.  There were a couple of points he made that caught my ear:

  • After he launched Facebook (Facemash at the time) for the Harvard campus, Mark was having a conversation with his friend about how someone should build an equivalent version for the whole world to use. He did not realize at the time that it would be him.
  • A year later Mark came out to Silicon Valley and was driving though Mountain View, looking at the buildings of all the big companies, and he was thinking to himself that one day he would like to build a company like that. Again, he didn’t consider that Facebook would be it.
  • On hieing: would you be happy to work for that person?

Nathan Blecharczyk – Founder, Airbnb

The biggest takeaway from Nathan’s talk was from their story of meeting their users. At the time they had a small amount of users in New York but not very many bookings. This was during their YCombinator stage when they were based out of Mountain View. On Paul Grahams advice they took a trip to the East Coast and met with every single one of their users there. It allowed them to make  a personal connection with them and in turn they were able to influence their listings. For example they made creative modifications to the descriptions, put up nicer pictures and lowered the price. They ended up with a handful of cherry picked properties and the bookings started flowing in!


All of the talks have made me think about why do people start companies. It is obvious that it is the hardest path and carries the most risk. In Phil’s eyes working for someone else it does not produce lasting results. Its not something that you could call your life’s work. On the other hand Chase said that when he was starting Watsi, his friends were happily working for other companies (like normal people do) building products that helped to solve problems they cared about. But ultimately I think it has a lot to do with simply building what you want to see in the world, like Jack encouraged us to do.

If anything, attending Startup School has reassured me in that I do want to start my own company. It also opened my eyes to applying for an accelerator, perhaps even YCombinator but that will require some further research.

One final practical tip for attending events in the future: Look up attendees before the event and connect. I had people reach out to me through Facebook but didn’t see it because it was in the other inbox. Its a very smart move and can save you time meeting the wrong people.

The crazy weekend of events may be over but Monday is a fresh start and  few of us SVIP’s are going to FailCon, followed by #techdrinkup blowup party presented by Spotify and ZenDesk.

If you are going to any events in the Bay Area, do drop me a line.

See you around!


One thought on “My Takeaways: YCombinator’s Startup School

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s