How to be an elite startup employee
The "social contract" for rockstar employees at many early-stage startups of <100 people, distilled from my imperfect and incomplete experience serving as an early employee & COO, then a founder.
Practice the subtle art of giving a damn
Your company owes you nothing. You owe your company nothing. Work like hell anyway, because work ethic is a habit.
The interview process is the one of the few places where there's no such thing as coming on too strong. Early-stage companies want people who want to be there. Hedging or playing hard to get — especially if you are seriously considering much later stage (or worse, FAANG) companies — can actually be a cause for concern.
There are two definitions of ownership: owning outputs vs. owning outcomes. When a manager and direct report disagree on whether the employee is “exhibiting ownership”, this is why… the employee is doing a good job at specific tasks / deliverables / outputs, but the manager sees a lack of ownership over outcomes.
Ownership over larger and larger outcomes is how you progress in a (well-run) organization.
High horses have no place at a startup, so don’t get on one.
Almost everything worth doing is hard.
There are two kinds of people: those who live to work, and those who work to live. If you are joining a startup, it should probably be the former — your work should be a meaningful source of value in your life.
The one non-optional capability to make it in a startup is emotional resilience. If you need a day off to "process" news at work, you probably shouldn't be working at a startup.
Try to understand what the CEO, founders, and execs are obsessed with and staying up at night thinking about. Sometimes it’s as simple as just asking in a 1:1.
Be
high authenticity = say what you think
high integrity = mean what you say
high reliability = do what you mean
high agency = do without being told
low ego = do even if you disagree
Find others that operate the same way, and appreciate you for doing all of these things.
If you truly have low ego, you’ll find it easy to “disagree and commit.” All too often, people take this to mean “disagree and obey,” which isn’t good enough. The “commit” part is essential. E.g., if a VP of Revenue disagreed with their CEO and then truly committed… then their Sales Director shouldn’t even be able to tell that they VP had disagreed. There should be that much solidarity and trust.
Find a crew of amazing people. Make the most of it.
Find a company where you can trust leadership. It frees you up to focus on actual work without cognitive load.
The Maslow's Pyramid of amazing people is Integrity → Competence → Authenticity → Good Taste.
If you are working on problems that have meaning for you, with people you have affection for, the rest is gravy.
Write a “user manual” for people you work with. It will save a lot of heartache and misunderstanding in the future. (h/t Claire Hughes Johnson)
Deeply understand behavioral styles. Frameworks like DISC make this easy. Internalizing these styles can really open your eyes to how differently people communicate.
Not everyone has to like you, but you probably can’t thoroughly piss off your manager, manager’s manager, CEO, or multiple immediate peers.
In a high autonomy culture, the best managers want you to manage them. They won’t tell you what to do (except in rare cases), but instead will give you a goal to run at… and expect you to pull them in when you need help.
An employee’s job is to execute on their mandates and create leverage for their manager, in that order.
A manager’s job is to unblock, enable, and accelerate their employees, in that order.
An early stage startup does not have an obligation to proactively “develop its people”. At a good startup, you are wearing so many hats and solving so many problems that you are growing and developing without even trying… and others around you are trying to do the exact same thing. No one has the time to think about “developing” you. If you need help, you need to identify that and ask for it.
Don’t expect that every company welcomes politics or "bringing your whole self” to the workplace, or work-life balance. There’s nothing wrong with wanting these things in your workplace, but there’s also nothing wrong with your company not wanting those things in the workplace. This is the culture-fit assessment: the company decides what its culture is, you decide what your values are, and both parties assess during the interview and employment relationship whether those things are a match for each other.
Teammates come and go. The customer and the problem persists.
Life is long and a multi-turn game. If you went through highs and lows with a group of people you respect, it’s a waste to not keep in touch with the ones you cared about.
A (healthy) dose of anxiety and urgency is essential
At an early stage startup, speed is more important than velocity. This is because your advantage is agility. When you can change direction on a dime, the direction matters less than the pace.
The only thing that works for cracking GTM in the early days is throwing shit at the wall, seeing what sticks, and doubling down on that. The “best practice” stuff really only matters post-PMF. (While there are no obviously “right” answers, there are definitely obviously “wrong” answers that you should quickly reject for your product / market / segment.)
Building a startup means feeling bad constantly. When you don’t have PMF, you feel bad. When you do have PMF, everything breaks and your customers might get angry at you and you feel bad. There is no feeling good. (h/t Michael Seibel).
The best definition of PMF is that people want to buy your thing faster than you can make it. (h/t Michael Seibel / Y Combinator).
The essential differentiator of a startup (as opposed to a small business) is growth (h/t Paul Graham).
(The right kind of) experience matters
Spend your 20s trying to discover the things you’re amazing at, that you can harvest the rest of your life.
Spend your 30s trying to find the people you respect and vibe with, that you can work with the rest of your life. (h/t Eric Bahn)
The definition of “being strategic” is the ability to optimize across multiple dimensions to achieve a global rather than a local maximum. The more dimensions you can optimize across, the more strategic you are.
A salesperson who considers product strategy in their process is one notch more strategic than one who doesn’t.
If that person also takes into account gross margin and LTV calculations when comparing two deals, they’re one notch higher up.
If they can consider mandates from the exec team and board in evaluating opportunities, that’s yet another notch.
An MBA has no relevance to building a startup. Being successful at a large company (>1,000 people) has no relevance to building a startup. This doesn’t mean these are adverse signals, but they aren’t obviously helpful signals either.
A banking or consulting background has one relevant skillset for building a startup: the willingness and ability to work long hours, under pressure. That’s it.
All things equal, a person who has 2-3 years of work experience at a quality company is an order of magnitude better than that person as a fresh graduate.
All things equal, a startup hire who has been early at another startup for 1-2+ years before is an order of magnitude better than someone who hasn’t.
All things equal, a founder who has founded and run another startup for a meaningful period of time before is an order of magnitude better than someone who hasn’t.
All things equal, a founder who has been early at another startup for 1-2+ years before is 2-3x better than someone who hasn’t.
All things equal, a team that has worked together before for a meaningful period of time will operate 2-3x faster than one that hasn’t.
Ask and you shall receive (help)
"Mentors" outside the company who are several steps ahead of you in their career almost never make sense (h/t Alexis Ohanian). Instead find either a mentor within your company (ideally but not always your manager); or find a near-peer to meet regularly with that you can jointly problem-solve with; or find someone who's one step ahead in their career.
Even better -- find a support group. Especially if you're going through a hard time, but ideally always. Build vulnerability based trust.
If you find that you still have a lot of unresolved stress or emotional trauma, consider doing a mushroom journey.
Cognitive load and context-switching are the mind-killer. Pay to alleviate these things at work and — if you can swing it or afford it — in your personal life too.
Learning to give, get, and solicit feedback is a skill worth it's weight in gold.
The Maslow’s Pyramid of scaling yourself and your organization is learning how to Do it yourself → Hire people to do it → Outsource it → Automate it → Not do it at all. It turns out that most things don't need to be done.