Why you should not work at a startup

The Aha! team never hides behind screens. (Unless it is for a photo-op.) | Photo by Jodi B Photography

March 4, 2024

Why you should not work at a startup

by Brian de Haaff

The myth is rooted in reality. When you think of a startup, you probably visualize a few folks building a technology product from a garage in Silicon Valley. It all began about 85 years ago in Palo Alto, California, with the world’s “first” startup, and a company you probably are familiar with: Hewlett-Packard. Will one of the startups launching today become a similar tech giant? Maybe. But good luck figuring out which one.

Tech startups are more volatile than ever. So is it still the right move to build your career at one?

I ran a poll on LinkedIn to see what others think. The results were pretty evenly split. In my opinion, the answer is definitely “no” for some. Years ago, I wrote about why startups are typically not a good place for recent college graduates. I stand by that today — jumping into a fledgling company when you do not have much experience yourself is generally a recipe for chaos. And the risk is even greater if you work remotely and do not have a chance to interact with many cross-functional teammates.

Startups can be incredible places for highly motivated people with a tolerance for uncertainty. But there are plenty of folks who might not thrive at a very young and unstable company. It all depends upon what you are seeking from your next professional venture.

Do you mainly want to "get rich quick"? Look elsewhere. Remember that of the many hundreds of tech startups that emerge each year, very few lead to meaningful growth or value creation for those who join. Even those that sparkle during boom times wobble towards disaster when market conditions turn bleak.

Career growth happens when you are clear about your goals and what type of work environment will enable you to make the most progress towards your objectives.

Personal development also hinges on the values of the company you join. When a company embraces its responsibility to serve customers, colleagues, and communities, teammates will have a good chance to find different ways to improve and advance. Lasting companies thrive during both go-go and go-slow times because they take a broad view of the value they create.

Chris and I waited to hire at Aha! until we had more than 100 paying customers. It was important to be sure that the business was viable before risking the livelihood of others. We were fortunate to find accomplished teammates who were passionate about our mission and able to contribute immediately — many of them are still with us in senior leadership positions today.

We also focused on creating sustainable career development programs. Within the first few years, we pioneered frameworks, an onboarding curriculum, and training resources so the company could support new hires and help the team grow in meaningful ways.

Our principled approach is unfortunately not common. You need more than enthusiasm for an awesome idea to succeed at a startup.

At Aha! we had the benefit of past experiences — good and bad — to inform how we built and scaled the company. Both Chris and I have worked at early-stage companies and founded a few as well (with varied levels of success).

The adventure of building a company is something I continue to relish. And I think if you can find the right opportunity, embarking on that adventure at the company's onset is often a terrific way to grow your skills at an accelerated pace. But it is not for everyone.

Of course, there are not that many open roles at startups right now. Many are experiencing layoffs or prudently pausing hiring. The fervor (and funding) for startups will eventually return, though. So if you are thinking about whether now is the right time to join a tech startup as an early employee, consider the following:

Decision makers are limited

You do not choose the direction. At an early-stage startup, only a handful of people will be responsible for setting the company's direction. Those folks might have different priorities and make different choices than you would. Although that is true of any organization, the impact is more deeply felt in a startup environment. Is that something you can tolerate?

Work is exposed

You will have nowhere to hide. That means that all of the work and any accomplishments or failures will be easy to see. The initial team will be small and the deliverables numerous. Folks will be learning as they go. Are you ready for context-switching, close collaboration, working beyond your area of expertise, and rapid feedback cycles?

Personal growth is undefined

Your career growth will mostly be your own to manage. You will be doing work that people in the company have probably not done before. And you will likely have the opportunity to quickly learn new skills and contribute in new ways. But startups do not usually have specific advancement paths or robust training programs in place at the beginning. Are you interested in balancing that level of autonomy and responsibility?

Uncertainty is guaranteed

The future will not be obvious. It is a challenge to solve problems that have not been solved before. And what will make it more difficult is that you need people to pay you for something that has not existed before. A startup can also be dramatically pushed by larger economic forces — impacting potential customers and funding (if you are trying to raise it). Most startups fail. Are you comfortable confronting the unknown on most days?

There is nothing like the energy and excitement of building something new with a like-minded group. But there is little that is worse than when your effort has created no value.

If you have read this far, then you are likely someone who is thoughtful about your career path. Maybe you have worked at a startup before and are craving the adventure once again. Maybe you are working at one now and layoffs loom ahead. Or maybe you have always worked at larger companies and are curious about a leap to startup life.

Build your career at a tech startup. Build your career at an established tech company. Build your career at a massive tech conglomerate. I cannot tell you which one to choose — all three hold promise and different rewards.

What I suggest is that you dig deep into your own heart and mind. Where do you do your best work? How do you want to grow? What value do you want to create? The answers will reveal which one is right for you, right now.

Aha! continues to build sustainably for the future. We are bootstrapped, profitable, and hiring for key roles.

Brian de Haaff

Brian de Haaff

Brian seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 product development software — and the author of the bestseller Lovability and The Startup Adventure newsletter. Brian writes and speaks about product and company growth and the journey of pursuing a meaningful life.

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