How to make startup life less painful
Smiling While Engulfed in Flames: A Startup Memoir
At Duke two weeks ago, a student asked me one of the best questions ever. I had just shared the Elon Musk quote that starting a company is like eating glass and staring into the abyss of death, and they asked:
Do you have any suggestions to help deal with the pressure of a startup? Any ways to make the glass more appetizing, or the void a bit brighter?
Oh, do I ever.
The first step is to realize that pain is unavoidable.
At an early-stage startup, the deck is stacked against you.
Mistakes are more common: what you’re doing is harder and less certain; nobody has ever done it before
You are more likely to be personally responsible for those mistakes: there’s no hiding at a startup, whether behind a mentor, a big team, or “that’s how we’ve always done it”
Your personal role is more important to the company: the numerator (you) is the same, the denominator (team size) is smaller
All mistakes are more deadly: any sufficiently big miss can actually cause the entire company to fail
In total, that means that you, personally, are far more likely to make a mistake that threatens to take down your entire company. That is the abyss of death staring back at you.
Here’s your first lesson: accept the pain. If you resist and aim for painlessness, you’re doomed; you’ll give up once the going gets tough, as it inevitably will.
You should only join a startup if you know it’s going to be painful and still think it’s worth it.
But, of course, you aren’t reading this because you want to be scared away from startups — so here’s how to thrive in a high-risk work environment.
👭 Pro-tip #1: Work with people you admire.
This is the simplest and most effective tip: work with people who you keep you happy and productive. I’ve seen both the presence and absence of such people in startups, so I fully appreciate their value.
When I started my first company, I did it alone. I found some “co-founders” who helped me — Ravi built our demo, and Jack helped close a customer — but none of them were all-in. (To be clear, this was my failing; I didn’t recruit them hard enough.) As a result, my founding journey was incredibly lonely. I was left to deal with massive setbacks — like losing $1,000,000 and a co-founder in a 24-hour period — all by myself. And because showing despair or weakness as a founder is a recipe for disaster, I had to take those Ls with a smile on my face. The early days at a startup are almost always filled with failure after failure, and having nobody there with you in the trenches really sucks.
Luckily for me, Astranis has amazing people — and they have made it unspeakably easier to get through the hard times. I won’t list them by name because I know it would embarrass them, but I could talk for days about how a Sporcle champion, a NASA Administrator-to-be, a world-record-holding spearfisherman, a sweet-talking Texan, the world’s humblest rocket scientist, Elon Musk’s favorite engineer, a man uncorrupted by 20+ years at a Big Company, a program manger who could be a surgeon… etc, etc, etc… have made my Astranis journey so joyful and rewarding.
I learn something new every single day; the team is unbelievably cool under pressure; and even when things suck, we can turn to each other, make “oh god, not again” faces, laugh, and lighten the mood.
It’s a night and day difference. Find great people.
🤝 Pro-tip #2: Get perspective from people you trust.
Startups can be bubbles.
Once you’ve followed my first piece of advice, you’ll find yourself in the thick of battle with a group of people that you really trust. After surviving some battles with them, you’ll inevitably feel like you all have some shared, special knowledge that nobody else has. But that’s a dangerous mindset.
No matter where you work, the vast, vast majority of the smart people in the world do not work at your company. And in a high-pressure, high-stakes arena like a startup, you’ll need to tap into external wisdom to get unbiased perspectives that’s aren’t seeped in your company’s Kool-Aid.
In practice, this means making friends with people who work at other startups (or finding mentors who used to work at startups). It’s possible to get good advice from people who haven’t worked in startups, but be very careful: many rules that work great for big businesses can be fatal for startups.
One of the most helpful things I did as a Chief of Staff was build a network of Chiefs of Staff at other venture-backed startups. Some of this came from the Y Combinator network, other times from Slack groups I joined, and other times from cold outreach. At the very least, such connections can remind you that all startups are hard. And more likely, you’ll get real tips that help you avoid some unforced errors.
😤 Pro-tip #3: Lean in.
Pain is bad. You should avoid failing. Glorifying startup pain is obviously dumb.
But pain is an inevitable possibility whenever you really, truly care about the outcome of something — so you should run towards the pain if you care about doing things that matter.
The reason why I love startups is because early-stage operating is an inherently creative act.
You’re bringing something new into the world, and to do so, you have to sign your name on your creation with permanent marker. There’s nowhere to hide. If you fail, you’ll have to admit it — you can’t hide in the hierarchy of a huge company, you can’t shirk responsibility off to a manager or direct report, you can’t pretend like you don’t care.
You do care. That’s why you’re at a startup. And although genuinely caring is supremely uncool, you do it anyways — because it’s the fastest way to learn, the ultimate test of your skills, and you believe that your work matters.
Creativity is hard in today’s post-ironic, critical, fault-finding culture, but I agree with Laura Riding:
To be nobody-but-yourself — in a world which is doing its best, night and day, to make you everybody else — means to fight the hardest battle which any human being can fight; and never stop fighting.
And Key and Peele:
Working at a startup is going to suck. There will be days when you would rather eat glass and stare into the abyss of death than tackle your to-do list.
But if you’re in the right place, startup life can be worth the pain. So, take a chance! Be creative. Don’t settle for a boring, safe job with people who don’t inspire you to be better. There is greener grass out there, as long as you’re daring enough to find it.
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