The most important skill in Startup Land: Drive
Operator Skill Tree: Edition #1
When I moved to San Francisco to become a founder, I had a golden, shining vision of what startup life would be like.
I saw myself pitching a room of investors in a beautiful, sun-lit office; I heard myself saying “innovation” and “disruption” non-ironically; I imagined leading a massive team by being a little bit of a jerk but ultimately lovable; and, inevitably, amassing a generational fortune.
As soon as I got to Silicon Valley, however, I was greeted by a harsher reality:
Startup life is painful.
The odds are stacked against you, so you’ll have more failures than normal. Each failure is objectively worse, as they’re all existential when your company is finding its footing. And, adding insult to injury, everything that goes wrong is your fault and your problem to fix. Even when you do succeed, the highs fade quickly — like the time, pictured below, when I nearly won $1,000,000 in a pitch competiton, only to have my co-founder leave me the very next day.
Elon Musk famously said that running a startup is like “eating glass and staring into the abyss of death,” and he wasn’t kidding. Neither was Paul Graham, one of the founders of Y Combinator, here:
“Startups are not magic… if you want to make a million dollars, you have to endure a million dollars’ worth of pain. For example, one way to make a million dollars would be to work for the Post Office your whole life, and save every penny of your salary. Imagine the stress of working for the Post Office for fifty years. In a startup you compress all this stress into three or four years… If starting a startup were easy, everyone would do it.”
In order to brave the emotional rollercoaster of startup life, you’ll need one crucial skill:
Angela Duckworth, author of Grit, defined drive best:
(1) Do hard things.
(2) Don’t quit.
It’s that simple, and that hard; drive is way easier said than done. If you can follow those two steps consistently, you’ll be on your way to being a great startup employee — but if you can’t, startup life might not be for you.
Part One: Do Hard Things
Being ambitious is scary.
As social animals — and survivors of high school — we have internalized the Law of Conformity: individuality is scary, so it’s bad to be superlative in any way. “Safety in numbers!”
Even when we set out to “innovate,” there is a natural human tendency to reason by analogy — i.e., to imagine what we’ve seen before, but with a new coat of paint. Sam Altman, the CEO of Open AI, wrote:
…when Instagram started to get really popular, it felt like you couldn’t go a day without hearing about another photo sharing startup. That year, probably over 1,000 photo sharing startups were funded, while there were fewer than ten nuclear fusion startups in existence.
But, of course, copycatting sucks the oxygen out of a market and ensures mutual destruction; as Peter Thiel would say, competition is for losers.
The lesson: if you want to find hard problems that are worth your time and energy, run towards the pain.
Ben Horowitz, co-founder of venture capital firm Andreessen Horowitz, explained this concept vividly:
When I was CEO of Loudcloud, we were growing so fast that the Fire Marshall called to warn us that he would shut down the company if we didn’t find more space for all the people we had. I told my controller to find us some space right away, but it somehow didn’t feel right. It felt like darkness. Somewhere in my body, I knew that the end of the dot-com boom was on the horizon, but I couldn’t logically articulate it, so I delegated the decision. I ran from the fear.
We signed a new lease for what would become known as “The Maude Building” because it was located on Maude Avenue around the corner from the original building on Mathilda Avenue. It gave us room to grow for the next several years. It required $30M in restricted cash.
The dot-com crash came, we lost nearly half of our customers, and we never moved into The Maude Building. The lease we signed was for $10 per square foot per month. When we tried to rent it out, we found that post dot-com crash, the market price was $0.90 per square foot per month. But given the number of companies that had gone out of business, there were no takers even at that price. I ran away from my fear and lost $30M. Thirty million dollars that I badly needed. Yet somehow, some way, we survived—and maybe we survived because I never ran away again. To this day, every time I feel fear, I run straight at it, and the scarier it is, the faster I run.
Horowitz’s example is written for a manager, but his advice generalizes well.
You know what’s painful? Being a beginner. It’s embarrassing! I had the ambition to race a triathlon for years before I mustered up the courage to learn to swim as an adult. Even today, I can still only breathe in the water by turning my head to the right: I am procrastinating in becoming an ambi-turner because I don’t want to go back to flailing around in the water as a beginner. I’d rather just stick to “good enough,” even if it’s supboptimal.
You know what else is painful? Starting from a blank page. It’s indescribably easier to follow in someone else’s footsteps than to start something new. I also know this from experience: in college, I joined existing club and rose to leaderhip positions and didn’t start anything new, delaying my entrepreneurial experimentation by at least four years.
In both cases, should have run towards the pain. In the first case, there’s no alternative: if I don’t start out as a beginner, I’ll never become an expert. And in the second case, I never put myself in a position where utter failure was a real possibility, and didn’t test my drive in college.
In short, you need to do things that others won’t to succeed in the startup world.
Learn new skills. Build things from scratch. If you stay coast in the wide, well-defined path of social conformity, you’ll never test your drive to learn, to build, and to succeed. So venture out — and start now.
Part Two: Don’t Quit
Sadly, venturing into the unknown is the easy part: anyone can set ambitious New Years Resolutions, but few actually follow them.
The daily challenge that awaits you at an early-stage startup is to live to fight another day.
As legendary angel investor Naval Ravikant said:
If you’re a normal employee, you can quit and the startup will probably survive. But if you want to participate in the startup world to the fullest, your job as an employee is simple: be an energy-giver, not an energy-taker. You should leave every day knowing that your presence helped build the team’s collective perseverance and left you with enough gas in the tank to do it all again the next day.
I realize that, again, that’s way easier said than done. It’s something that I personally struggle with — I’ll often burn way too hot, hit my limit, and spend a couple of days feeling angry or sad before I’m actually the happy, productive, gregarious Christian that gives his team energy. That guy is never going to quit, and he can even help others stick with it through the hard times.
There’s not much more to say here: just don’t quit.
If you need help, as everyone does, find activities outside of work that bring you energy, surround yourself with energy-givers, discover an accountability system that works for you (e.g., Silicon Valley peeps love Mastermind groups) and — no joke — read a self-help book. The latter helps me: if David Goggins can finish an ultramarathon on two fractured legs, I can definitely finish writing this newsletter every week.
Part Three: Prove to an interviewer that you can do hard things and cannot quit
As all but my most recent readers will know, this is the first post in a new series, the Operator Skill Tree.
That means I’m here to help you get a job at a startup.
Unfortunately for us recruiters and you applicants, drive is hard to assess in an interview and even harder to assess in a resume review. How do I know that you won’t quit just by reading a few (inflated) bullet points?
Alexandr Wang, co-founder of ScaleAI (a startup building artificial intelligence infrastructure that was recently valued at $8.7 billion), has a simple framework: hire people who give a shit.
If someone is applying to Scale and has never been deeply obsessed about something before, then it’s a bad bet to think Scale will be the first. I have a particular line of questioning around this:
What’s the hardest you’ve ever worked on something?
How many hours were you working a week?
Why did you work so hard? Why did you care?
When were you the most unmotivated in your life?
What’s the thing you’re the most proud of?
Do you think it was worth it?
For an obsessed person, it’s always worth it.
So, for a first practical piece of advice, get obsessed about something!
That’s admittedly a longer-term project, however, so here are three things you can do right now to prove you have drive in an interview.
Focus less on the projects you’ve been a part of, and more on your individual contributions. What have you done? Why did your presence on the team make a difference? If you really care about your job, you’ll think about this kind of thing all the time.
Crush your interview prep. Go all out. A useful exercise is to ask yourself what most people would do to prepare, and then to do more than that — remember, you have to be ready to do things that others won’t!
Flex your understanding of exactly how hard startup life is. Startup folks tend to be skeptical of people that come from big businesses. While you can use the Big Business Card to your advantage (e.g., I love when candidates express frustration with how slowly their previous companies moved), the null hypothesis is that people don’t really know what it’ll be like working in a resource-constrained environment unless they’ve done it before. Have a great answer prepared to the question, “What would you have done if [X project] had half of the budget and needed to be done twice as fast?”
The commonly-cited stat says that 90% of startups fail, but I’d put it differently: 100% of startups fail, but only 10% have enough drive to recover.
There’s no better predictor of startup success than having a team full of ridiculously driven people — so if you want to excel in the startup world, you could do much worse than by improving your willpower.
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Disclaimer: There are two reasons people write: to teach, and to learn. This piece is the latter for me. I love using this newsletter to put structure to my thoughts on hairy topics, and this one — exhorting people to try harder and not give up — is particularly hairy. I’m eager to hear what you liked and what you disliked from the above. Please reach out and let me know!