How to Work At A Startup

Some general advice on how to select and work at any startup

Choose carefully

99% of startups out there are ego-driven rides for people who have learnt to code, have some experience, or are able to raise capital. The fact that someone is doing a startup is about as airy as saying someone is dreaming something. You have to dig deeper to understand and assess whether this startup, at this point in life, makes sense for you or not. Only the 1% are worth working for where if you work hard x smart x startup is on the right trajectory, you will come out of it with not just great experience, but wealth earned from stock options. 

A startup is an extremely long job interview until you get fired, quit or get wealthy. There is no stable state prior to that.

Another way to view a startup is: it is an extremely long job interview until the point stock options which were granted to you have materialized, you own them (are vested), are worth something and give you a financial return. If you get fired or leave before that point, then all you have earned is a salary, which means you didn't choose properly or didn't work hard x smart enough.

Why the focus on work hard x smart ? 

Startups by default are dead. It is through the sheer will and actions of its team that it becomes something viable. It's not the proving ground for your skill, or for you to use it to learn to fulfill some other objective in life. 

No, listen carefully, please.

You are on the Titanic. It's been hit by an iceberg. You see water rushing in. This is the default state of your startup. There is no time to be distracted by anything else.

Social media busy-ness ? It will kill the startup. Other activities: going to conferences, meeting and networking with people, being super-active with open source and other social causes. Sure, noble indeed. But it will kill the startup.

If you cannot focus, the startup dies. Or if it doesn't, and you are distracted, you lose the job sooner or later. Or even if you don't - you are not given stock option grants at which point why even work for the startup then ? Instead if you focus, the startup wins, then you have more time and wealth to then be actively helping others. But here, now, focus please.

There is fluff and busy work which one might do to appear useful: write some code, tweak some design, and so on. But that is like counting the stars while being on the Titanic. You need to survive. Figure out where the lifeboat is, where the life jackets are, help those who need it the most, keep morale high. If you find yourself "appearing busy", you are doing a great dis-service to your team mates - in which case the right thing for you to do is to quit or to be fired. Startups are not for you in that case and you should consider an alternate career path, like working for a big company and being told exactly what to be done or something else.

Founder 101

Founders are the crazy, obsessed people who bet everything they have on the germ of an idea. They go through an extended period of ridicule from their peers, friends and family on how ridiculous their idea is, but they believe in it. They are so obsessed thinking about it, that they pass on valuable opportunity costs like working for other startups and foregoing generating wealth for themselves'. By the time you are meeting a founder of an emerging startup, that founder has already spent a large amount of time and effort thinking through various permutations of how to correctly position the venture.

Your idea #10 might have been the idea number #147 which the founder already thought through and is now living in a different time-line. A "no" might mean not that the founder is dismissive of you, but that there isn't time to explain everything.

Key is to not take idea rejections personally, and to disconnect ideas from egos. 

Yes, founders are time-travelers. It's their job to project into the future and weave a path of success for the company, which benefits you as well. It's not about ego - but doing what is right and necessary, which is all that matters. If the startup fails, the founder loses psychologically, financially and in many other ways.

For even early employees - that risk is not the same. You earned money for the time you spent and can leverage that work experience into a job at another startup. Although you lose in terms of opportunity costs, long hours spent working and loss of value or wealth potential, but that is standard operating procedure at any competitive workplace, without the benefit of potentially lucrative stock options. Working at an early-stage startup, you are an integral part of it's success. Cut the founder some slack sometimes ? He or she is a human and will have ideas, opinions, good days, bad days.

Do you then do everything which is asked ? 

No. Think independently. 

Founders inherently want you to think and operate like founders even though that is not in your title.

Some might scoff at it and think "well if this venture does well then this person makes far more than I do, so why should I give it my best, let the founder give his or her best ideas and work hard. I will take it easy..". Firstly, if you don't give it your best, it is easily observable, you will crash the startup and thus deserve to lose your job to one of the millions of eager folks in the world who do want it. Second, is to be mindful of the journey the founders have been traveling, what their opportunity cost and their risk profile has been. Third, based on your performance, you are an owner in the company. The level of it is discretionary and subjective, but would you rather be employee #100 at say, Google or own even 10% at most startups out there ?

Startups align incentives in the form of stock options. Also, in other words, if you don't have a grant or a promise for these in the startup you are working for, quit it immediately for one where that path is available. 

Founders are also humans, and have to balance between having an outsized ego (which is good to attract attention which helps the company), with being practical and humble listeners, doing what is right for the venture, whether the idea came from an early junior intern or from whoever. The best founders will seek to reward no matter who at what level is contributing to the idea and practical growth and momentum of the venture. 

This is hard to grasp for experienced hires. You might have 5 years of top-class relevant work experience, but it might happen, that a junior intern is more engaged and driven and is consistently driving the startup forward. Who gets a bigger stock reward ? The intern.

Poor performing, soon-to-be-dead startups will have incentive schemes where people are rewarded based on archaic concepts like tenure, experience, position. This is massaging egos territory. Nobody wins if you own 90% of something worth $0 eventually, vs if you own 0.1% of something which is an enormous success.

In other words, everyone is aligned to the stock of the company.

If what you are saying and doing helps the product and the startup improve and grow, and the founder and management team are able to observe that, then you get rewarded with stock. 

This means it's in your personal economic interest to not be afraid to challenge founders on ideas. Don't do everything you are asked to do precisely - question it, see if it fits, be an independent thinker, present your feedback not with intuition but make a compelling case. If it is still not taken up, don't consider it as your idea being rejected, but an idea being rejected. Going back to the previous section, the founder might have time-traveled through that idea maze earlier already and concluded to travel a slightly different path. Small iterative bets compound in the long term.

Don't give up

If you give up, then here's what that looks like. You do exactly what is asked. You ask for specs. You don't do things beyond the hours you are paid ("9 to 5-ers"). Startups can't operate well with such folks on board. For whatever reason, they have lost the will and the drive and are here to just collect a paycheck. They will inadvertently cause lasting damage, and soon move on, having earned work experience while taking up the opportunity which could have gone to someone else more eager and driven for the idea at hand. If you feel you are missing the passion in the venture, talk to the relevant people. Try taking a vacation to clear up the mind. If you still feel that way, the right and the noble thing is to quit instead of lingering on. 

Founder-drive time is very limited

An early stage startup exists as long as the founder is motivated and inspired by what he or she is working on. But this drive time in life is limited. It needs fuel to sustain - and that is in the form of various things in life, such as being able to pay a salary to herself and the employees, being able to attract customers, build a compelling product and so on.

For whatever reason, if the founder is checked out, you should bail as well. The startup will crash, and you will have lost out on your opportunity cost in life. Remember, by choosing to work at this startup, you are not working elsewhere where you could have also owned stock in the venture.

By the same token, when you do work, give it your 100%. And then a bit more. That’s the only right strategy assuming you chose the right startup work at. Imagine the flip scenario: giving it less than your best, getting fired eventually or not being integral to the firm down the line, while the startup goes on to do very well. You will spend every day of the rest of your life thinking about the what-ifs. Don’t be in that situation, and prevent it from happening now. The ask is only to work hard and smart.

Be a snowball: choose your own role

At early stage startups, based on your drive and motivation, you could put yourself in a position where you are getting the role you want, over and beyond what you were even hired for. Once you are in the company, and have access to the founder and management team - that's your golden ticket. If this startup gets on a good trajectory and you are driven, working hard and smart, you will likely go on to earn a lot of wealth. That will come from direct stock ownership in the company, but you will also get known in the industry, which would open up further opportunities. Like a snowball, which keeps growing further it rolls downhill.

Startups can be thought of as carefully calibrated rocket ships. One small miscalculation, and they miss the mark. Spend too much time thinking, and the weather changes. There is peril every single day, success is not guaranteed.

All you have is your own judgment, where if you choose the right startup, the next best thing for you to do is to be fully engaged. Work hard. Work Smart. Question everything but be respectful when decisions are made. It's an opportunity of a lifetime and you don't want to be reflecting back upon it at a later point in time with a "what if".

Above all, have fun and take care of yourself

Start-ups can get stressful. There are crunch times and deadlines. You need to think of your own well-being, sleep and rest patterns, meditation, exercise, diet and nutrition. Spend time with family and friends where you can. Quit startups which drive you too hard consistently - for there the founder is not aligned with your incentives then.

It's not just economic, but overall well-being. If you chose correctly, gave it your best, then you ought to be winning in all dimensions, not just one.

Finally, choose the people. Ideas, code, strategies and positioning etc all change. High integrity folks are the ones you wanted to be working with.

Good luck. And please pass it around if you found it useful.