Meeting the Dawn

The brutal, beautiful realities of working at a startup

San Francisco at dawn

My girlfriend, and the sun, are still asleep as I creep out the front door. Stepping out into the cold, busy street in downtown San Francisco, the steam of my breath is lit more by streetlamp than the dark sky.

If I didn’t have the foresight to pick up some iced coffee or — in true desperation — a Red Bull, I take the time to desperately drink the cold morning air. Cold air keeps me awake, and if I want to navigate the next hour or so of precarious traffic without falling asleep I’m going to need everything I can to stay awake. I blast loud EDM. I start trying to memorize my schedule, recite the first lines of The Aeneid in Latin — anything to stir my brain awake and keep me going until I see the dawn.

We usually meet up somewhere south of the city on 101. There’s a long stretch of highway that rims the imperial hills surrounding Brisbane and the cold San Francisco Bay. Far across the water over the eastern hills, the dawn starts to shrug off the dark of the night in a fiery play of colors.

It yawns a few purples and oranges, stretches out and turns the impenetrable black into a deep cerulean, and eventually it waves at the early morning commute with its warm lambent glow. By the time I pass SFO, both the dawn and I are fully awake, and ready to launch the day.

The dawn and I are just getting to know each other. I’m not a morning person. I never have been. Back in college this fit my “archetypal software engineer” that I embraced, and I frequently remarked that without two shots of espresso, an energy drink, or ideally both I couldn’t be up and functional before 8AM.

Even outside of college, most of the places I worked didn’t really kick off until 8:30 or 9 or so. NetApp, as a very engineering-focused organization, tried to focus its meeting times till after 10. Most of the meetings I had in VC also happened after general business hours started, though it was expected for you to be up and working past midnight given that our cross-boarder relationship with Asia meant that 11:30PM was a great time to work with our colleagues in China.

Here it’s different. With a good chunk of our engineering team in Spain, my day tends to start around 6 or 7 every morning when I’m on the West Coast. Given that I need an hour or so to be up and ready to rock, that means that most of my weekdays kick off somewhere between 5AM and 6AM.

I’ve learned to accept, even look forward to the dawn. I liked the dawn’s more party-heavy cousin, dusk, for a very long time. The twilight of dusk and the approaching night was always something that made me excited about facing the evening. There was promise there watching the sun dip into the ocean — the enticing feeling that anything could happen.

Dawn, similarly has those qualities. But dawn’s excitement isn’t so much about what show we’re going to see or the people we’re going to meet. The excitement is about what we’re going to do — what we’re going to make. Even if I know that things are going to be hard, or I’m not looking forward to what’s going to happen that day, the dawn is a reminder that nothing’s set in stone.

For me, getting to know the dawn has been synecdoche with my experience joining a startup. I’ve known startups for a long time now. I grew up around my parents’ startup, I interned at one and later ran products that competed against them when I graduated, and after 3 years of venture capital I’ve learned a lot about what helps to make them successful.

But I haven’t really known what it was like to be in a startup.

I’ve never known how hard it was to actually pull 80–100 hour weeks for months on end. While I’ve seen the startup vs. big company competition from one angle, I’ve never been on the significantly more outgunned side of the fence.

I’ve never known how it feels to be in a situation where everything is mired in a sense of uncertainty and danger, nor what it’s like to have to operate in situations where you have to be just swing first and learn from your success (or failure) ex post facto because you don’t have the time or resources to carefully execute something.

Don’t get me wrong; I’m not complaining about my job here. I love my company and what I do. But I think my experience working at a startup over the last year has made me despise how contemporary Silicon Valley culture “sells” the startup experience.

These people aren’t working.

This is the image of the modern Silicon Valley startup: a highly-paid, never ending college party. Startups in San Francisco are now quick to proclaim the variety of perks that their “hackers” get, and the coolest startups proclaim how their “work hard/play hard” culture rewards their employees with things like company ski trips and endless drinks and alcohol.

Now I get that the entire point of this marketing is to get attention. All of the above certainly gets attention. And if you’re a twenty-something software enigneer, all of the above could be very appealing.

But it’s not realistic. I don’t know anyone, at my company or at other startup that’s doing sustainably well, that works less than 10 hours a day or is going to happy hours all the time.

You’re working — frequently to a possibly unhealthy degree — your fucking ass off. Startups definitionally have to double or triple their growth year over year, and doing that with limited/no resources means their employees are constantly struggling (sometimes with a gun to the back of their heads if they company is run purely on investor money).

I wasn’t naive enough to know that this reality didn’t exist when I was a VC or an operator at bigger companies. But as someone actually working in a startup now, I feel pretty annoyed that the TechCrunch/SF mainstream image of the “constant party” experience is what we’re pushing out to the mainstream.

Succinctly put: it’s one thing to get together in a room, drink a ton of alcohol, and talk ad nauseum about “disruption” or “changing the world.” Actually doing that is really fucking hard. It’s scary. Working at a startup isn’t some huge party — it’s a dedicated, concerted sacrifice and a gamble that you’re taking with your career and your livelihood.

I wish we respected that reality, and instead shifted the positive narrative around working at startups to focus on dedication to solving a problem rather than “perks.” Beyond being more honest to the realities of working at a startup, this approach highlights the real rewards of working at a startup.

Yes, there’s the monetary reward of being able to arbitrage your shares for potentially lots of money. I think we’re all pretty familiar with this reward. But I think for the really dedicated and motivated startup founders — and those who work under them — the struggle itself is part of the reward.

Years from now when I look back on my time here at AlienVault, I’m not going to fondly talk about my vesting schedule or some SXSW party.

What I’m really going to remember are the times where my team and I stayed long into the night drawing our product’s roadmap in a sea of post its on the board. I’m going to regale stories about that time we were presenting a prototype to our investors, wondering mid-presentation in the back of our tired minds whether or not we removed the test data we wrote with less-than-kosher language.

I’m not going to remember some tech mixer or startup party. I’m going to remember how my colleagues and I struggled and we made serious personal sacrifices because we actually wanted to build something disruptive — and because we didn’t want to let each other down. And when we shipped product, in that glorious moment where we taste victory, it’ll be all that sweeter because we worked so hard and sacrificed so much.

Working at a startup is like waking up to meet the dawn. It’s hard. At times it’s uncomfortable. But after you shrug off that sleep, and watch the sun explode in color over the horizon, it’s pretty amazing.

It’s worth it.

Show your support

Clapping shows how much you appreciated Andy Manoske’s story.