How to survive working at a startup

An entrepreneur is someone who will jump off a cliff and assemble an airplane on the way down. - Reid Hoffman

Startups are chaotic shit shows. Nothing makes sense. Ever. Even if sometimes it seems it does. And for a short period of time, the anxiety fades away. But the next morning everything changes. Again. And our brain starts trying to solve the puzzle of uncertainty. Again.

Putting too much energy into lowering the entropy of your startup is guaranteed to end up in burnout. And you'll leave or you'll get fired. Instead you should invest in what will give you compound returns. This is a list of behaviours, attitudes, tips and activities you should focus on while working at a startup. Your position doesn't matter. This list is generic enough that anyone working at a startup can apply it in their day to day.

Don't be a jerk

Almost every social conflict can ultimately be traced back to a lack of humility, respect and trust.

So be humble. You don't know what the f*** you're doing. Nobody does. You are not special. You are not unique. You will never do anything remarkable. Probably. So treat everybody with respect and trust your team. If you're ever going to do anything remarkable, you're not going to do it alone.

Degubbing Teams by Fitzpatrick and Collins-Sussman talks in depth about this topic.

Understand the stage of your team early on

Ried Hoffman talks in his book Blitzscaling about the 5 stages of a startup: family (1 to 9 employees), tribe (10s of employees), village (100s of employees), city (1,000s of employees) and nation (more than 10000). But at each stage some teams are pirates while others are marines. Some act like early stage startups and others like specialized consultants. Some teams embrace chaos while others fight entropy at all cost. Some adapt and improvise while others have strict and well defined processes. Some are product teams while others are feature factories.

Understand this early. You will know how to behave and what to spend your energy on. It will tell you what kind of people to hire, if you should be a generalist or a specialist, if you must focus or multi thread. If you should let fires burn or take care of every little thing.

Get shit done

Done is better than perfect. Deliver something small in weeks instead of spending months trying to polish the edges. Do your job as if something will drastically change in the next month. In early stage startups that window is even smaller. So never commit to long term projects. There is a high probability they'll get canceled. Or you'll be transferred to a different team. Or you'll get bored and tired.

Ambitious and long term projects can succeed. If they are done iteratively. With small feedback loops. So set expectations for the short term and deliver every iteration as if it were a new product or feature.

For any product or feature you must make it simple, make it valuable and build it piece by piece. Ron Jeffries talks a lot about how to do this in The Nature of Software Development.

Understand how business works

Working at a startup is all about using your skills to create a profitable and sustainable business focused on growth. It doesn't matter if you are a Software Engineer, a Product Designer or a Growth Marketer. Don't get obsessed over code, design, processes or management. Your skills are means to an end.

Learn the core business concepts for your context. Create a basic dictionary that everyone can consult. Understand how your work impacts the numbers. Read a book about the market you're targeting. Figure out how the Venture Capital landscape expects from startups like yours. If you don't understand the business, you won't be able to make the right questions. And you'll take poor decisions. And you're not going to be able to focus your energy on the right actions. Understand HOW business works. Probably you familiar with the business but you need to understand how business is made in your context.

Care about the customer

Make customer's life easier. Add value through your work. Don't do amazing. Do useful. Create something with purpose. Listen to your customers. Call them. Literally. Like, pick up the phone and freaking call them. Understand their needs and what they care about.

Master communication

Adapt communication depending on the audience. Don't talk to everyone in the same way; not everybody understands ideas in the same way. Nor everybody will put in the effort to understand what you are really trying to say. As a rule of thumb:

1. C levels have a cluttered schedule. Be brief and concrete. Ask for specific actions or advice.
2. Business and sales people understand numbers. Use them.
3. Engineers won't read long texts. Use bullet points. Start with why instead of what.
4. Designers like a good story. Pay attention to structure.
5. Product managers like journeys with steps. Use numbers instead of bullet points.
6. Managers are probably the only ones who will try to understand what you are trying to say.

Mine information

Any startup has an official organizational chart. But there is always an unofficial one. Information travels through the latter. Learn how information flows through your organization. Top to bottom, bottom to top, side to side and hidden paths. Relevant information will never come to you. You must go and search for it. Most people will assume you already know what you are supposed to know. And they will tell you what they think you may be interested in. So ask questions to find out what really matters. Basically, mine information.

Ask just the right amount of questions

Not asking questions looks as if you didn't care. Too many questions looks as if you are a negative person, a trouble maker and you have no clue. With time you'll figure out what questions have a higher return.

Get your numbers right

People will ask "why" as much as five times. So do your homework. Have data at hand to back up your answers. Otherwise it's just your opinion. And it's worthless. Unless you are a C level and you use your power to back up your opinions. But without data you'll lose credibility. Check your numbers twice and make sure your conclusions tell a cohesive and unified story.

Treat your processes as a product

Just because a process makes sense on paper, doesn't mean it works in real life. Some processes emerge naturally. Others are defense mechanisms against chaos. Either way, set up a basic process. Treat it like an MVP and iterate over it. Measure its impact and ask for feedback. Don't try to fix problems all at once. Don't try to do perfect from the first day. Don't copy other people's processes. Use scrum, kanban, agile and lean as mere anecdotes and inspiration.

Ask for forgiveness instead of permission

What's written in your job description is not really the job you're actually supposed to do. Instead, you need to do what everybody expects from you. So figure it out soon. And if you don't like it, do what's expected but also do what you can't.

Avoid bureaucracy at all costs. Take ownership. Don't ask for permission. Act first. Accept the rules but ignore them when you want to change them. No change has ever happened by following the rules. Be wise and push it just the right amount. Don't expect somebody to say you can be a leader. It will never happen. You need to become a leader.

Don't wait for the status quo to change. Hack your way through it. Worst case scenario, you'll get fired and you'll find a better job. Best case scenario, you'll learn and you'll transform your organization.

Avoid meetings

Most meetings are useless. Every successful human on the freaking plant agrees on this. Time is the only valuable resource you have. Meetings are the death of productivity. David Heinemeier even says meetings are toxic.

As a rule of thumb, don't attend meetings without an agenda. Meetings with more than 4 people are definitely a waste of time. Replace meetings with emails or Slack messages. Don't accept meetings just because it pops in your calendar app. Don't let other people block your calendar, they're just trying to capitalize on your time. That's unacceptable.

Make the pie bigger

Peter Thiel talks about how competition is for losers. Naval insists that status is a zero sum game. So don't try to take the place of your CTO. Don't lose your time with internal games. You're fighting for a piece of a small pie. Instead spend your energy trying to make the business bigger and more successful. Challenges, responsibilities and opportunities are going to get bigger and bigger. There is going to be more pie that you could ever handle.

Seek collaboration instead of competition. Make the people you lead become as good as you. You won't be able to grow and do other stuff if there is nobody that can replace you.

Be optimistic. Always

Startups are a chaotic. Uncertainty is the norm and failure is almost guaranteed. 90% of new startups fail completely. Around 20% fail in the first year. 34% of startups close within their first two years.

And yes. You need a vision for the long term. A strategy for the medium term. And tactics to fight short term battles. However, the truth is nobody really knows what's going to happen in the following 3 months.

But your only option is to be optimistic. Even in the darkest times. Even if the startup is about to shut down tomorrow, remain optimistic. Especially if you are a leader. Nobody wants to work with pessimists that see doom in every move. And nobody will follow pessimistic leaders.

Ask for and give feedback

Direct and brutally honest feedback pays off. Don't keep anything from other people. If something needs to be said it should be said.

It’s so rare to have real and honest conversations nowadays. We all put on so many layers and play these corporate and professional predefined cliché roles. That’s why feedback is usually so shallow. Giving and receiving feedback only works if the people know you. And I mean, really know you. The real you. If they don’t, their feedback is going to be shallow, empty, and useless.

Find a mentor

Invest in yourself. You can and should read books and articles, take courses and listen to podcasts. Beware because most tech content is bullshit. I personally hate the word consuming. Especially consuming content. But it portrays today’s society where the pattern is consuming — instead of learning or creating. Consuming — without questioning. Consuming and hiding behind an authority.

But if you really want to grow, apprenticeship is the way to learn how to make the most out of your skills and theoretical knowledge. So find a mentor. Ideally your mentor would be inside your organization. Ideally someone at the same level of your manager or above.

Meet people from the local ecosystem

Take time to talk to people in your industry. Don't limit yourself by their role. Interesting people are scarce. If you're a designer, don't meet only with designers. Get to know Tech Leads, Product Managers and CEOs. Staying only in your little square limits you a lot. And that applies to other parts of life too. Surround yourself with restless and incredible people.

Don't wait for other people to reach you. Go and deliberately search for the people you want to meet. Most people won't say no to a coffee. It works better if you already have a specific topic that interests you. That will be the catalyst for a good relationship. Reach and talk to other people in an honest way. We are all tired of having cliche conversations.

Go watch TV

Working a crazy amount of hours doens't mean you're doing a great job. You should work smart instead of hard, because hard work is for idiots and losers. Being successful is not a matter of how much time you put in. It's a matter of the quality of your decisions.

Don't fall into the trap of meritocracy because it's just bullshit. Erik Dietrich talks a lot about this topic in Developer Hegemony: The Future of Labor.

Take care of yourself, sleep a decent amount of hours, exercise, meditate, learn something you like and dedicate time to your loved ones. As Morty says: Nobody belongs anywhere, nobody exists on purpose, everybody's going to die. Come watch TV.