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9 Things I Learned Working for Startups

And how it rocketed my career

Apr 8, 2019 · 9 min read

Contrary to what many want to believe, you aren’t likely to get rich joining a startup. But it could be a massive boost to your career.

It was to mine.

Because of my experiences at startups, I was able to land the best role of my career. Launching my growth from entry-level intern to principal engineer in less than ten years.

If you are thinking about joining a startup, or perhaps already there, consider some of the lessons I learned below. I hope that you can use them to maximize your time there and use it to leapfrog to your next career move.

That is, until you retire with all those stock options, of course.

Somewhere the myth perpetuated that startups are grownup frat parties. True, the perks that some go through to pull recruits in can be fantastical.

Beer fridges at every desk.
Ping ping and video games in every meeting room.
Parties and travel.

The truth is, most of the time, those perks go unused. They are for looks and feel goods. And perhaps the occasional Friday night cheers. The one time I tried to play ping-pong, I got glares and told it was too loud.

An early startup usually has no customers, no products, and no revenue. It will be a long time before profits materialize. If they ever do.

They hired you to help change that.

Which brings in the flip fallacy, startups are all grind. Say goodbye to your friends. Kiss your family goodbye.

Yes, there can be some long hours. Again, they need you to bring in the first revenue. But any company that drives its employees 80 hours a week will soon lose those employees to another company offering a fancier lunch and fewer hours.

Key Takeaway: all jobs have their perks and their long days. Don’t base joining a company by those alone. Be ready for some long days at crunch time and don’t assume it is all fun and games.

Observe the culture already there. See how many employees are taking advantage of the perks, or look way too stressed.

In a startup, there was never a sense of “that’s not my job.” There aren’t enough employees to fill every role or need.

When I joined the startups, I was given a title and had a specific work scope. But that didn’t explicitly call out furniture assembler, random test subject, or courier. My job description didn’t include QA or business development.

And yet, every day brought things that needed to get done. Things that would bring the company forward or boost my coworkers.

They weren’t always fun or glamorous, but they gave me opportunities to shine and to learn. It opened doors for additional responsibilities and increased work scope.

Even as something as mundane as taking out the garbage shows your leadership that you can do whatever it takes to help the company succeed. It highlights that you care about the details.

Key Takeaway: do not assume that if something needs doing, it is someone else’s job. Just get it done and back to your “real” job.

And while you shouldn’t do it expecting a reward, you will be surprised at what can come about by just being helpful.

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Photo by Ilyass SEDDOUG on Unsplash

At a small company such as a startup, they hire every person with care. You aren’t just another body to fill a chair and bloat out an org chart.

They hired your skills, brains, and perhaps good looks.

So if you have an idea for something that needs improving, speak up. A good startup will not care about the chain of command or fight over little fiefdoms.

But be prepared to defend your idea. Your idea may require a significant change to the product or company. So back it up with data or specific customer feedback.

A good leader will vet all ideas out before making such a change. And a great leader will listen to everyone in the company, no matter the role.

Key takeaway: never hesitate to share your ideas and make yourself heard. Speak up and defend what you think is a good idea.

This isn’t limited to your area of expertise, use the incredible visibility you get in a startup to suggest improvements in sales, software, or strategy.

As a reverse to the previous point, do not get stuck in your opinions. One of the incredible things about working at a startup is the team can bring a wealth of diverse experiences.

Some of those experiences may have taught them a different way. Maybe even a better way.

I had thought myself a fairly decent embedded programmer. But when one of my coworkers reviewed my code, his first reaction was:

“This shit actually works? Who wrote this crap!”

And so for the next six months, I learned better techniques from him, and my programming skills became even stronger.

Many times I disagreed with him on what was the right way, defending it with reason and facts. He did the same.

Some instances I agreed with what he presented and changed my mind. Other times, he learned something from me.

In the end, it was a better product than either of us could have created on our own.

Key Takeaway: if someone else suggests an idea, be open to accepting it. Take advantage of the diverse background of your coworkers and learn something new.

Many startups, especially in the hardware space, are created because of a novel technology. The founders believe it is the greatest thing since the internet.

Sometimes this works out, but more often the product fails to be a critical success. The technology got into the way of what the customer wants.

I was a part of this first hand. The technology my product used was remarkable and novel. It was incredibly low power (10 years on a single battery).

And it was cool.

But the technology was not cheap and had severe limitations. About 10% of our customers had issues where it wouldn’t work as intended — and there was nothing the technology could do to overcome it.

With a later change in leadership, our team refocused direction. Our new leaders made us step back and think about what was best for the customer.

What does the customer care about?

We dropped the cool tech and impressive looks. We used mundane gadgets and simplified the design. This lowered the cost by 75% and overcame all of the previous iteration’s limitations.

And our customers loved it.

Key Takeaway: never put the technology before the customer. Yes, the next big thing may need something new. But make sure it is best for your customer.

If not, set aside the technology and look at something else. Or find a different customer. One that would benefit from the technology.

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Photo by Franck V. on Unsplash

I have had the privilege of working with incredible people. Some of the best at what they do or junior talent that will be sought after for years to come.

But even with impressive skills, those without good interpersonal skills quickly suffered.

They may have got the job done. But with only five of you on the project, interacting with a challenging person became a drag. And quickly the whole company was effected.

It is easy to stand out on such small teams. If you do not take into account the personalities around you, it will turn for the worst.

With each playing a critical role at the company, you cannot afford to be rude or impatient with anyone. This alone may deter you away from startups if you would rather sit in a desk and ignore everyone all day.

Key Takeaway: be friendly with your coworkers and work to improve your social skills. They will be critical to your success with such a small, intimate team.

Practice your communication skills. Watch videos on networking. Practice small talk. Becoming skilled at interacting with your coworkers will take you a long way in your career.

When a large, established company launches something new, it may hardly make a headline or bump the stock price. Same if the product fails. There are exceptions, but a company massive enough to run multiple product lines rides the bumps fairly smoothly.

This will not be the case for startups. It may have zero products and zero customers when you join. Launch day will be stressful. Hopefully followed by a joyous party.

A big customer win changes the entire focus of the company — just to make them happy. But the loss of a big sale or the flop of a product could be a disaster for the company.

With so little mass to the company, revenue changes either direction make huge impacts. And those impacts affect everyone at the company.

This directly connects with #6 above, how well you are liked by your coworkers, and especially your leadership, will make a big difference in how your role changes.

Big wins lead to growth, and you are precisely in the position to be a leader in that growth, such as managerial or project lead responsibilities.

Big loses instead lead to layoffs and cut expenses. While not a guarantee that you will make it through the layoff just by being liked, being disliked will put you towards the front of the line.

Key Takeaway: a startup will have wild fluctuations as it grows and matures. Be ready for either outcome and ride the waves. Getting overly excited or worried will not bring a good result.

A startup requires intelligence and flexibility to succeed. Both at the individual level as well as the corporate.

This provides a great learning opportunity for you. I talked about personal flexibility above, but pay attention to your teammates’ work and the direction of the company as a whole. Nowhere else would you get this level of cross-company visibility.

When a coworker announces a change, strive to understand why they made that decision. What caused them to change their mind. Learn from their adaptations.

Same goes for when a leader makes sudden changes to the company direction. Depending on the company, you may get a transparent view of how a board of directors operates. At the least, you should be able to learn why and see how a company adjusts to meet changing demand or pivots to a new customer proposition.

So when it comes time for you to make a decision, you can take the combined experience of your peers and align it with where the company is going.

Key Takeaway: learn why things change at your startup. Whether it is a coworker making a shift in their design or the CEO declaring a completely different product will be released.

There is always a reason, and you can learn from it.

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Photo by Carl Heyerdahl on Unsplash

This is a culmination of the above steps, but one of the most significant benefits to working for a startup is the opportunity to step forward when the need arises.

You can expand your experience, highlighting your leadership ability, or even change careers. With so many things that need to get done at a startup, and never enough time or resources, you have a ton of openings to grow.

But do not let your team down.

Not that mistakes aren’t expected, any quality team will always expect and tolerant mistakes. But if you are so busy chasing after the “hot” work, and can’t keep up with your core responsibilities, it will not end well.

Unless there has been a clear change in what is expected of you, if you promised to do something, make sure you follow up and complete it. Missed expectations can end your career at a startup faster than anything else.

So look at any added opportunities as an added risk. The reward can be great, but so can the cost. Understand your limits.

Key Takeaway: startups are full of new, exciting things to learn and experience. But never let your team down by dropping what was already expected of you.

So if you are currently at a startup or evaluating joining one, set aside the potential for riches (I do hope they come true for you) and think about how it could move your career forward.

Use the visibility to stand out. Cross-coordinate with a completely different function. Learn new skills. And hone experienced ones.

A startup may not make you a millionaire, but it may launch your career forwards.

The Ascent

A community of storytellers documenting the journey to happiness and fulfillment.


Written by


Husband, father, tinkerer. Writing about hardware product design, life, mental illness, art, and overall being a good person and making cool stuff.

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment. Join thousands of others making the climb on Medium.


Written by


Husband, father, tinkerer. Writing about hardware product design, life, mental illness, art, and overall being a good person and making cool stuff.

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment. Join thousands of others making the climb on Medium.

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