What is it like to work for a Silicon Valley startup?
The Interview
An unsmiling software engineer answered the door.
“Is this the headquarters of …” I blanked. I’d literally forgotten the name of the company. We both looked at each other. Finally, it came back to me, “…Curated!”
“I thought you were a Bible salesman,” the engineer mused, stepping aside.
I saw the CEO talking to someone in the kitchen behind a counter piled with snacks. I felt relieved to see a familiar face, absolving me from having to explain my arrival. I’d met the CEO and Head of Product in a first-round conversation a week earlier. “Hi Valentine,” he waved.
I entered the Silicon Valley hacker house. There were two rows of four computer monitors with engineers typing away. A couple of people chatted in adjoining rooms. I followed the CEO into the backyard. I saw a brown stuffed animal rabbit at the far end of the yard in the dirt.
I entered a nearby bunker with a boardroom table and a TV on the wall, and pulled out my flash drive. “Oh, I don’t think we have a place for that,” the CEO indicated. I looked around puzzled and realized everyone had new Macs, which don’t have USB ports. I felt like a dinosaur. Like someone who’d brought a floppy disk to a meeting. Luckily, I’d saved my presentation to Dropbox as well. However, no one had PowerPoint to open it. I was resigning myself to the subpar aesthetics of using another program when the designer miraculously found PowerPoint on his computer at the last second.
I presented to the CEO, Head of Product, Product Manager, Designer, and Head of Marketing. After Q&A and a discussion, the CEO walked me out. I asked what makes someone a good cultural fit here. He said someone enjoyable to work with, as you end up seeing them more than your family.
I asked how they prioritize what needs to get done, and he said it’s about what fire is burning the strongest, that’s where they focus next. It’s like building a plane while you’re flying it.
Later that day he called to offer me the job.
I thought National Geographic was small — about 2,000 employees. Now I was heading to a company of 35 people. The team comes mostly from LinkedIn, as well as Google, McKinsey, and Facebook. The company raised $22 million in Series A in a round led by Forerunner Ventures (Warby Parker, Glossier, Away, Jet.com). The CEO had successfully sold two companies in the past, the second one to LinkedIn. I felt I would learn a lot from him.
After hearing stories in the job search about toxic startup environments, I wasn’t sure how to vet Curated’s culture. Ultimately, you take a gamble, but two things helped ease my worry on this front. The first was my phone calls with three Curated experts for my presentation — they were incredibly kind, and I felt energized by their contagious passion for skiing, golf, and cycling.
The second was the CEO’s flexibility and the tenure of Curated employees. I asked when ideally I’d start, and he said “tomorrow.” But he mentioned that he doesn’t believe in exploding offers and said I could get back to him on the job offer whenever, even after I completed an on-site interview with IDEO. He said he takes every hire seriously and wants to make sure I feel it’s a right fit for me. Longevity is important to them; they’d only ever had one person leave the company in the two years of its existence — and it was for graduate school. I felt that a toxic culture couldn’t possibly have such a low turnover.
I accepted the job. The CEO gave me a warm welcome, and warned me that the job will be like drinking out of a firehose. He said if by week 3 I’m not thinking “what is going on????” then I’m not pushing myself hard enough.
The First Week
Walking down a spaceship hall of green lights, I arrived at the door of Curated’s headquarters — a two-story apartment above the Walgreens next to the Caltrain station in San Francisco.
I thought it’d be weird to knock, so I tried the door knob and it turned without hesitation. Wow, anyone can walk in. No security desk, no signing in or anything. Not even any security badges. I shared my surprise with an engineer (I think the one who had thought I was a Bible salesman).
“The day we get security badges, is the day I quit,” he remarked.
“How come?” I asked.
“Because that would mean we don’t know each other anymore.”
A brand new MacBook Pro was waiting for me in a bag on my chair. I savored the unboxing of a new computer. I asked my neighbor what login I should use. He said he just uses his own Apple ID. I logged in with my own Apple ID in great disbelief, remembering all the high security at past companies.
“We are a real company I promise,” Matt from Business Development proactively assured me in our introductory phone call.
Dogs roam around, their claws click-clacking on the wood floor. At lunch everyone descends on the food delivery and are super social, and then twenty minutes later people are back at their desks like worker bees.
I made a suggestion in a design review with the Product team and felt excited to see it implemented onscreen for the next rollout of a web page. Gone is any semblance of bureaucracy or hierarchy — the idea-to-implementation turnaround is hyper-speed here.
I was happy to get three work priorities from the CEO early on, but then I got looped into several other things and this convo and that Facebook Live event, and here’s another company to look at, and so many Slack channels and they are all blowing up, and I can’t tell what’s useful right now and what isn’t. May I have your feedback on our Instagram strategy? I thought my head was going to explode trying to understand everything. I felt the urgency of getting up to speed fast. I absorbed everything as a listener and took notes like some furious Middle Ages scribe. I felt like an archeologist excavating all the institutional knowledge for answers.
People tend to work from 9am–6pm, and often sign back on at home after dinner. Honestly, I always looked forward to leaving work, walking down the hallway of green lights to the elevator. No more new information. I could finally just think and work in peace at home. I wished I could take a sabbatical. To press pause and read through every document and arrange everything I was working on in a neat row.
I asked a designer how he balances his big-picture work with all the daily requests. He said he keeps a Jira board (project management tool) of everything that comes at him in the short term and the things he wants to think about every night for three months. He mused that sometimes it happens that something is flagged to him as a monster priority in the morning, and he does a ton of work on it, and then by the end of the day it’s like the lowest priority or forgotten.
Meetings? They are like the flowing waves of an ocean. No sense of punctual start and end, they just flow one into the next, half an hour late here, hour late there, no problem. There is no grumble or frown. Just patience, understanding, and the communal sense that we are all in this together.
The office has three meeting spaces: a room upstairs with a door, the dining table downstairs, and a three-person couch next to my desk. One day, Matt asked me to take the lead on a phone call with a golf company. I scrambled around and was dismayed to see every meeting space occupied. “Just take it from the laundry room,” Matt suggested. I laughed at his joke.
But then I realized he wasn’t joking. I found the laundry room — the office’s fourth meeting space — a 10ft x 4ft closet complete with a washer and dryer. With the Head of Marketing next to me, I drove the meeting with the multibillion-dollar golf company in there, my computer on the washer and my phone on the dryer. It was amazing.
The toughest thing to get used to is the condensed timelines. I told Matt that what is being squeezed into a week would normally take two months in the real world. “In two months we could be selling stuffed water buffalo heads for all we know,” he joked. I mentioned to the COO how I hope everything won’t be so last minute like this and he chuckled, “we’re a startup man!” I guess it’s my new reality. I think I’ll end up having to manage myself in the face of chaos.
I remember on my first day, I asked a General Manager where he likes to travel. He said that when he worked at a large company he constantly looked forward to heading out on vacation, plotting the next as soon as he was back from the last. But since he’d joined Curated, he hadn’t felt that travel bug. “Working here feels like an adventure with friends in itself.”
A colleague came over to my desk and fist bumped me on her way out. Five minutes later, another co-worker came by for a fist bump. “Happy first week of work!” he exclaimed. Ultimately, what I value most about this place is how outrageously friendly everyone is. I couldn’t have ever imagined how a company could possibly nail the cultural fit piece so well.
A week had passed but it felt like I was already a month in. What is it like to work at a startup? Exhilarating. Many needs arise where you have to launch something completely from ground zero. For a scrappy innovator who loves learning, experimenting, and building things, this is amazing. There’s no structure. There’s no playbook. When you arrive on day one, there’s no one there to tell you what to do. You don’t work in one corner of an office on one specific niche every day. You’re an explorer. You embrace the discomfort of constant novelty, of getting pulled into conversations left and right. You crave the alone time to focus on one thing, but you enjoy the collaborative creativity of straddling multiple domains.
I ended up working from the apartment for only two weeks. After the holidays, we moved into a real office a block away. I wish I had had a chance to be there in that unit for longer. It felt like the quintessential startup experience: the laundry room phone calls, all-hands gatherings around the dining room table, the CEO opening the window of the upstairs meeting room to call down to an engineer below, looking for a pair of scissors by opening every drawer in the kitchen (in fact, there were like no office supplies anywhere), avoiding boxes of mountain bikes and skis in the entryway, laughing that someone actually used the shower in the bathroom, bumping into people pacing in the hallway outside on the phone. Habituated to more traditional office environments, I savored the daily cognitive clash of productive-workplace-in-homey-apartment life.
Would you have advice on going into a startup? I’d love to hear your tips in the comments below.
Valentine Quadrat is a Product Strategist at Curated (curated.com).
