2015 by the numbers

# of days in Chicago: 161
# of flights taken: 51
# of [air] miles travelled: 65,609
# text messages sent: 16,718
# of sets of keys I have for apartments that are not mine: 7
# of cities those apartments are in: 3
# of countries visited: 6
# of books purchased: 177
# of haircuts: 2
# of classes I “attended” at GSB: 1
# of successful Kickstarter campaigns: 1!
# of investors pitched: 2
# of pictures/media exchanged in “Cuzins” WhatsApp group: 615
# of pictures taken (and not deleted) on iPhone: 811
# of Tinder matches: 665
# Times I was called a Persian terrorist: 1
# of journals I filled up: 3

Oh, and another thing…


Picking Brains #1: 20 Minutes with a YCombinator Alum and CTO of a $100m+ Startup

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I sometimes get the chance to talk to people way smarter than I am and I will start posting mini-field reports on interesting chats in a category called “Brain Pickings” so as to share the information I gather.

Earlier this week, my partner, the brilliant Sasha Gutfraind,  for super-secret project #3 (or “the tertiary project” per one of my pals), and I decided to put our idea through the application process for YCombinator’s Fellowship program.

The application opened on July 20 and was due 1 week later, on July 27 at 8pm PT. A good friend of mine sent over the application on the Monday it was released, which was while I was on a business trip to San Francisco (my partner and I both live in Chicago) and so I didn’t know what the right strategy was.

After sitting on the application for a day and doing some research, I sent it over Sash, and we decided we were going to go ahead and complete it. I rebooked my flights to land in Chicago the next day (Wed 7/22) and we strategized on how to get the application done best given our limited knowledge of YC and the very rough idea-stage our product was in. I plan on doing a much longer, detailed debrief on the application process (regardless of whether we’re accepted or not) soon, because we learned a ton so keep an eye out for that post.

The relevant data for this post is that immediately after deciding to complete the application, I reached out to my network of super-smart, talented nerds to get some advice and a super-smart nerdy person responded and offered to introduce me to his boss, or, as he put it: “He’s not my boss. Way too high up for that. He can def. fire me though so be good haha.” While we both thought it’d be a long shot to get on his calendar in the next 72 hours, after a few reschedulings, I scored a 30-minute phone call slot with his “boss” – the CTO of a $100m+ startup, and a YCombinator (YC) alum.

Here are the 4 questions I asked and the notes I made as he answered them.

1. Keeping this YCombinator specific, how can we best position our product?

– His response was that YC really cares about the strength of the cofounding team and that they’d want to see a strong, committed team with a lot of willpower. Because the idea wasn’t 100% fleshed out, which is actually OK for the fellowship, the team needed to be stronger than the initial idea. He also suggested highlighting our domain expertise — that we were super knowledgable about the problem and the way our product could fit into the space. He brought up one of my favourite terms lately: understanding and finding your product-market fit.

2. As the non-technical co-founder of this company, what do they (YC) want to see from me?

– His thoughts were that I focus on why I’m the “right person to solve this problem” – once again speaking to my area expertise and alignment with the problem. Traditionally, YC applications ask people to discuss things they’ve “hacked” as technologists. Hacking can = being resourceful, so he suggested I talk about things I’ve hacked, even if they’re not under the traditional, technical definition of the word. Because my involvement with startups has mostly been operational, it was also about treating the company as a product and so building up a company = building up a product.

3. As a non-technical co-founder of this company, how do I recruit superstar technical talent, eg, a rockstar CTO?

– This was an interesting question to discuss because if I’m the founding member of a tech company, couldn’t the argument be made that I’m a technical person? (This kind of applied to Q#2 as well.) Nonetheless, understanding how to recruit technical talent is super important and while I’ve had some experience thanks to my trading firm days, I figured asking a member of my target demographic (rockstar CTO!) for his feedback would be helpful. He narrowed it down to two basic things: first, that there needed to be familiarity and trust built over time. I’ve learned this one through experience – Sash, definitely the more technical person in the startup, and I have known each other for several years and have built a super-strong friendship. The second thing was that we (the co-founders) needed to have complementary skillsets with respect to the company and idea: my softer qualitative and operational experience aligning well with the technician’s workhorse side. Things like product skills, design, sales, etc. would matter. Lastly, he said that for him, he’d want to see someone with belief and passion in the project and the perseverance to push it through.

My first 3 questions took up 20 minutes and I had one big ask left (Q#4): would he take a look at the answers to our application questions and alert us to any blind spots/give feedback? He agreed to do so and his feedback was absolutely invaluable in helping us refine our answers. I’ve kept multiple drafts of our application and the feedback we got on each of them. Once the idea goes public, I’ll post them on this blog as well.