Rejected from YCombinator

and how I’m using their feedback to change my approach

If you’re new to this Substack, I’m building a Slack alternative.

Last month I applied to YCombinator’s S22 batch. I had two interviews with them but unfortunately they decided not to fund me this batch. Although I was upset not be accepted, the overall experience was positive. They asked good questions and provided detailed feedback.

In this post I write about the YC application experience, the feedback they provided and how I’m using it to change my approach to build a better Slack. As always, I’d love to hear your thoughts too so please do share them with me.

Timeline of Events

• March 24: YC application deadline (although they mention May 19 as the date you'll know by if they’ll be inviting you for an interview)

• May 15: I submitted my YC application

• May 20: I receive an email inviting me for an interview

• May 23:

  • 7pm UK time: Interview with YC partner and associate

  • Midnight: I receive an email for a “Reinterview” (as opposed to a “follow up” interview).

• May 24

  • 10pm UK time: Second interview with a different YC partner and associate

  • Midnight: I receive an email that YC have decided not to fund me this batch.

  So overall the turnaround time between events was very quick. I especially appreciated the same-day responses after my interviews.

The interviews

The interviews were both only 10 minutes each (which is quite crazy to think about seeing as this is a $500k decision they’re making!). Naturally, they were both very fast paced and the time was up before I’d even realized it.

Here’s what they asked me during the first interview:

• What are you building?

• Why doesn’t slack scale?

• Go to market strategy?

• Why doesn’t slack build a news feed? (see previous post for context)

• Would this be a replacement for slack or work in addition to it?

• You’re a solo founder. How are you thinking about a cofounder?

• What profile are you thinking about for a cofounder?

• What will you do if this idea doesn’t work out?

In reflecting back on this interview, I don’t think I was clear enough on what I was building. My interpretation of this was that I didn’t understand it well enough myself. This prompted me to write down my thoughts so that I could clarify it to myself, and this is actually what led me to writing my previous post.

Here’s what they asked me during my second interview:

• What are you building?

• Do you have any prototypes or designs? What progress have you made?

• Why is it different?

• How will you acquire users?

• Have you worked on a growth team before? What did you learn from that?

A big chunk of this interview was spent in digging into how I was going to acquire customers. I didn’t have a good answer to this — in fact I even said in the interview “I don’t have a good answer to this”. When I received my interview feedback it confirmed that this is their biggest concern:

Hi Lior,

Unfortunately, we've decided not to fund Kudu this batch. We appreciate you coming back to interview again and we enjoyed talking with you both times. You're clearly a talented engineer and building with a deep passion for improving on Slack.

However we worry that Slack is now so deeply embedded into every company, it’s incredibly hard to get users to pay attention to a new tool. We’ve no doubt it will happen eventually but we suspect it will require a product that creates a completely new paradigm and no one saw coming. Similar to how Facebook eventually became the biggest threat to Google’s ad business. So while we think you have a great set of ideas to make incremental improvements to Slack's product, we worry that won't be enough for you to get customers and scale this.

We know we’re often wrong when trying to predict the future like this and we’d love to hear from you again in the future as you continue building the company. Thanks for taking the time to interview with us.

Finding My Customers

A line which particularly stood out to me in their feedback was:

it’s incredibly hard to get users to pay attention to a new tool

I initially agreed with this feedback, but after pondering on it I don’t think it’s entirely true. My thinking is that if a product is solving a big enough of a pain point for a user/company, then it will be easier to get them to pay attention.

I have so far been identifying individuals within companies that are experiencing pains with Slack and hence building an experience for them first (see my previous post for more details). However, after thinking more about YC’s question on how I will acquire customers, I feel I should instead be focusing on identifying companies that are experiencing these pains with Slack. Whilst I have a vague idea of who these companies are, I haven’t been specific enough in defining exactly who they are and hence why I was not able to answer the question of how I will acquire customers. I then had a chat with Cameron MacKenzie who mentioned that one way to go about this is to find the companies who will be my first 10 adopters, identify what their problems are and build a solution for them. Hence this is what I’ve been focusing on for the last month.

Finding My First 10 Customers

So how do I find my first 10 customers? I know from my research that the Slack experience becomes worse as the number of messages sent increases. Factors that affect this are the number of employees in a company, whether they are remote-first or work in-person, and the number of timezones the team is based across. Hence I’ve been focusing on companies that are remote-first and have between 20-100 employees. The hypothesis for this is that these companies are feeling the pains of Slack whilst still being small enough to change relatively easily.

With this in mind, I’ve been searching for these companies and sending cold reach-outs to their CEO/CTO/Cofounders (the idea being that these are the people in the company with the social capital to drive the change from Slack to a new app). My reach-out is something along the lines of “I’m frustrated by Slack and building an alternative for remote teams. If this resonates with you, I’d love to hear more about what problems you’re facing. It would be very helpful for me in determining what I should build for teams like yours.”

So far the progress has been okay. I have about 5 companies that I feel would be my early adopters. It’s a slog, though. My response rate is about 5-10%, and not all those that respond would be good first adopters. It’s a numbers game and so I’m spending large chunks of my day tediously sending cold reach-outs. Sometimes the lack of response can make me doubt myself or validity of the idea. However, just when I begin to feel discouraged during this grind, a response of "I’m very interested!” is all it takes to energize me again and keep me going!

And so the next month for me is going to be more of the same to find a few more early adopters. If you have any thoughts on my approach or advice I should take into consideration, I’d love to hear it! I also plan to finish an early prototype soon, so let me know if you’d be interested in having a look at it.