Surviving Y-Combinator with Wingman Cofounder Shruti Kapoor


LISTEN TO THE PODCAST

You've seen the videos, read the blog posts, and heard all the buzz about Y-Combinator. But what's it really like to get into a YC cohort and go through the program yourself? In today's podcast I chat with Shruti Kapoor, Cofounder & CEO of Wingman who shares her firsthand experience at the hailed Silicon Valley accelerator.


READ THE BLOG POST!

The following is written by this week’s podcast guest, Wingman Cofounder Shruti Kapoor, and originally published on Medium.


My First YC Office Hour

I just stepped out of my first group office hour at YC and I am blown away. It is kind of hard to describe exactly what has blown me away and maybe I will just try to share the experience with others here.

If you are in the startup world you have probably heard of YC and stories around it. It has become so well known that in so many ways the last few weeks since we became a part of YC have been overwhelming and underwhelming both at the same time. You know so much about the program through their videos and startup school that in some many ways when you walk into the office there is a feeling of deja vu.

The program consists of 4 main things, all leading up to the Demo Day:

  1. Bootcamp — this is the 101 of everything you need to know depending on the stage of your company — sales, marketing, pricing, hiring etc.

  2. Lectures — each week Founders share their stories. It is incredibly encouraging to hear how tough each journey is because we only get to see the destinations as an outsider. It is somehow intimate even though today there are 100+ people in the room during any of these sessions

  3. Group Office Hours — each company is assigned to a group with 5–6 other companies along with 4–5 YC partners. It is time to get feedback, brainstorm and maybe even pivot

  4. Individual Office Hours — you can set up time with YC partners with a specific agenda you need help with

What I experienced today was #3 — Group Office Hours. The format for today’s discussion was:

  1. What do you do — a 1 liner pitch

  2. What progress have you made in the last 2 weeks

  3. How will you get to $100MM ARR

Ofcourse, the questions seem pretty basic but what isn’t so obvious is how could someone really understand your business, understand whats going right or wrong and help you think about the bigger picture. I was blown away by how powerful a simple question can be if it is asked and answered honestly with the desire to learn and improve. Here are a few examples of this discussion, I will not mention names of companies or people but some examples:

Example 1: “We help companies scale ABC”

Feedback: Are companies looking to scale ABC or is there a different pain point they have?

Example 2:

Intro line: “We are an employee benefits company blah blah that helps in ABC”

Feedback: What you do is ABC, partnering with companies is only a distribution channel. You might in the future even offer ABC without this channel.

Example 3:

“How were the last 2 weeks?”

“This week is looking pretty good, we have…”

Feedback: We asked you about the last two weeks, so what happened there?

Example 4:

“We are a non-profit that does ABC”. We don’t want to charge the States because we want them to spend the savings on improving XYZ instead

The question: If States save money will they actually spend it in XYZ or will that budget just go away.

What really impressed me and I am finding it hard to convey is how in a 60 minute session with 6–7 companies the partners switch context so many times and are still able to get to the bottom of it in the first 30 seconds.

The powerful combination is — really smart Partners with a tonne of experience & perspective + humility + authority. What this means for Founders is that not only are they getting great advise but it is also being applied to their context and they are getting it from a position of authority/credibility. When doing a startup you are always second guessing the decisions you make. You often don’t have data to back decisions and eventually it is often down to your gut. YC gives you a better gut :)

Is there a way to replicate this? As I go through this experience I will think more about this and share my thoughts in a future blog post. Till then, time to hustle towards our Demo Day goals!

Find Wingman online:

www.trywingman.com

Rajiv Nathan