🌁 Silicon Valley n00bs
In October 2018 my Co-Founder Gillian & I came up with the idea for Cherry. We moved to San Francisco to go through Y Combinator in early 2019 and raised a $700k+ angel round which we used to build & launch our V1. Our product solved the engagement problem with employee perks/benefits (historically a 7% engagement rate was ~90% on Cherry). Now, after an unsuccessful attempt to raise a Seed round we’re closing down & sharing our learnings.
This article is part 2 in a 5 part series.
Leading up to our big move from New York to San Francisco I spent every spare moment enthusiastically binging on startup content to prepare for YC.
I approached deciding on a place to live in SF with similar enthusiasm. I curated a list of relevant spots: restaurants, groceries, gyms, bike shares, etc. in Google Maps to survey the neighborhoods & selected The Castro as the ideal spot to set up Cherry HQ. I researched apartments (as a “scrappy” startup our office would also be our home), weighing the pros and cons of each option and using Google Street View to “walk” the surrounding neighborhood before selecting our new place. Finally, I booked our flight for New Year’s Eve — a “brilliant” choice to save money.
Despite my obsessive planning efforts, I had inadvertently rented an apartment next to a “well-known crackhouse,” a fact that became pretty obvious when we rolled up to our new place in the middle of the night & witnessed how our neighbors were ringing in the new year. The next day we found a new, dingy apartment in SOMA under the 101 that had us taking turns sleeping on what we called the “real bed.” It was an early lesson in rolling with the punches.
Early Cherry HQ - Yoga block desks & one-time-use whiteboards:
The next three months we put every piece of advice & startup theory to the test. Our strategy going through YC was simple — to launch as early as possible & get paid customers to validate our idea (letting employees choose their own perks). We decided to quickly build Cherry as a lightweight Slackbot. Employees would use “/cherry” commands to view our perk marketplace directly in Slack, check their account balance, and access gift codes for their perk selections. If we could sell this, we’d know we were successfully following the YC ethos: “build something people want.”
Following Paul Graham’s advice to “do things that don’t scale” our order fulfillment process was partially manual. Hearing that the Stripe brothers gave early customers their personal phone number, we too posted ours online (leading to hockey-stick like growth for… spam calls). We even built an alert system that played our favorite Ariana Grande song every time an order was placed (quickly turning it into our least favorite song).
Our n00bish missteps showed we were book smart & street dumb — blindly following those who’d come before us. Thankfully, we found that perfection isn’t necessary for progress & our flawed efforts were the start we needed.
In 3 months, we built our MVP, got our first 200 paid users & gained invaluable first-hand experience.
➡️ Next: How Not To Fundraise
